KR102721427B1 - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents
Organic light-emitting compound and organic electroluminescent device using the same Download PDFInfo
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- KR102721427B1 KR102721427B1 KR1020160044337A KR20160044337A KR102721427B1 KR 102721427 B1 KR102721427 B1 KR 102721427B1 KR 1020160044337 A KR1020160044337 A KR 1020160044337A KR 20160044337 A KR20160044337 A KR 20160044337A KR 102721427 B1 KR102721427 B1 KR 102721427B1
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- South Korea
- Prior art keywords
- synthetic example
- biphenyl
- group
- hrms
- synthesis
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 170
- 239000012044 organic layer Substances 0.000 claims abstract description 25
- 239000010410 layer Substances 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 239000000126 substance Substances 0.000 claims description 26
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 238000002347 injection Methods 0.000 claims description 17
- 239000007924 injection Substances 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- 230000005525 hole transport Effects 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 238000004020 luminiscence type Methods 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 description 142
- 238000003786 synthesis reaction Methods 0.000 description 142
- 238000000034 method Methods 0.000 description 141
- 239000000376 reactant Substances 0.000 description 138
- -1 pyrimidine derivative compound Chemical class 0.000 description 45
- 239000000463 material Substances 0.000 description 33
- 125000004429 atom Chemical group 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 19
- PGKFQLBZPVLWRQ-UHFFFAOYSA-N 4-(3-bromo-5-pyridin-4-ylphenyl)-2-phenyl-6-(4-phenylphenyl)pyrimidine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=C1)C1=CC(=CC(=C1)C1=CC=NC=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 PGKFQLBZPVLWRQ-UHFFFAOYSA-N 0.000 description 18
- ZGTRMRKOLAKBOP-UHFFFAOYSA-N 2-[3-bromo-5-[2-phenyl-6-(4-phenylphenyl)pyrimidin-4-yl]phenyl]-1,10-phenanthroline Chemical compound C1(=CC=C(C=C1)C1=CC(=NC(=N1)C1=CC=CC=C1)C=1C=C(C=C(C=1)Br)C1=NC2=C3N=CC=CC3=CC=C2C=C1)C1=CC=CC=C1 ZGTRMRKOLAKBOP-UHFFFAOYSA-N 0.000 description 17
- JWUHOISKLKWKRE-UHFFFAOYSA-N 4-[3-bromo-5-(4-pyridin-3-ylphenyl)phenyl]-2-phenyl-6-(4-phenylphenyl)pyrimidine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=C1)C=1C=C(C=C(C=1)Br)C1=CC=C(C=C1)C=1C=NC=CC=1)C1=CC=CC=C1)C1=CC=CC=C1 JWUHOISKLKWKRE-UHFFFAOYSA-N 0.000 description 17
- NTFKWGNCFKHMBY-UHFFFAOYSA-N 8-[3-bromo-5-[2-phenyl-6-(4-phenylphenyl)pyrimidin-4-yl]phenyl]quinoline Chemical compound C1(=CC=C(C=C1)C1=CC(=NC(=N1)C1=CC=CC=C1)C=1C=C(C=C(C=1)Br)C=1C=CC=C2C=CC=NC=12)C1=CC=CC=C1 NTFKWGNCFKHMBY-UHFFFAOYSA-N 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 125000004104 aryloxy group Chemical group 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 9
- GNYOWFWNLZUKAQ-UHFFFAOYSA-N 8-[3-bromo-5-[4-phenyl-6-(4-phenylphenyl)-1,3,5-triazin-2-yl]phenyl]quinoline Chemical compound Brc1cc(cc(c1)-c1cccc2cccnc12)-c1nc(nc(n1)-c1ccc(cc1)-c1ccccc1)-c1ccccc1 GNYOWFWNLZUKAQ-UHFFFAOYSA-N 0.000 description 8
- 125000005103 alkyl silyl group Chemical group 0.000 description 8
- 125000005104 aryl silyl group Chemical group 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000000304 alkynyl group Chemical group 0.000 description 7
- 125000005264 aryl amine group Chemical group 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- MAFLVMPBOPVUJN-UHFFFAOYSA-N 2-(3,5-dibromophenyl)-4-phenyl-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC(=CC(=C1)Br)Br)C1=CC=CC=C1)C1=CC=CC=C1 MAFLVMPBOPVUJN-UHFFFAOYSA-N 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000005549 heteroarylene group Chemical group 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WNFYOJAPKFOQFW-UHFFFAOYSA-N 4-(3-bromo-5-pyridin-3-ylphenyl)-2-phenyl-6-(4-phenylphenyl)pyrimidine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=C1)C1=CC(=CC(=C1)C=1C=NC=CC=1)Br)C1=CC=CC=C1)C1=CC=CC=C1 WNFYOJAPKFOQFW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052805 deuterium Inorganic materials 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- HYZNIURBDZXTGX-UHFFFAOYSA-N (4-pyridin-3-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CN=C1 HYZNIURBDZXTGX-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- JMCTYYUBZSQNLN-UHFFFAOYSA-N 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=CC=2C3=NC=CC=2)C3=N1 JMCTYYUBZSQNLN-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
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- 125000005842 heteroatom Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- KXJJSKYICDAICD-UHFFFAOYSA-N quinolin-8-ylboronic acid Chemical compound C1=CN=C2C(B(O)O)=CC=CC2=C1 KXJJSKYICDAICD-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- RVPCPPWNSMAZKR-UHFFFAOYSA-N (10-phenylanthracen-9-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C2C=CC=CC2=C1C1=CC=CC=C1 RVPCPPWNSMAZKR-UHFFFAOYSA-N 0.000 description 1
- JTRWBBPLLGECJS-UHFFFAOYSA-N (9,9-dimethylfluoren-3-yl)boronic acid Chemical compound OB(O)C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 JTRWBBPLLGECJS-UHFFFAOYSA-N 0.000 description 1
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- VPSXHKGJZJCWLV-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(1-ethylpiperidin-4-yl)oxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OC1CCN(CC1)CC VPSXHKGJZJCWLV-UHFFFAOYSA-N 0.000 description 1
- DXCXWVLIDGPHEA-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-[(4-ethylpiperazin-1-yl)methyl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCN(CC1)CC DXCXWVLIDGPHEA-UHFFFAOYSA-N 0.000 description 1
- APLNAFMUEHKRLM-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)N=CN2 APLNAFMUEHKRLM-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- MCNFSXSJNZPTGE-UHFFFAOYSA-N 2-dibenzo-p-dioxin-2-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(OC=2C(=CC=CC=2)O2)C2=C1 MCNFSXSJNZPTGE-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- IAWRFMPNMXEJCK-UHFFFAOYSA-N 3-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=C(NC=2C3=CC=CC=2)C3=C1 IAWRFMPNMXEJCK-UHFFFAOYSA-N 0.000 description 1
- UHCYUVNJVPRFGF-UHFFFAOYSA-N 4-(3,5-dibromophenyl)-2-phenyl-6-(4-phenylphenyl)pyrimidine Chemical compound BrC1=CC(Br)=CC(C=2N=C(N=C(C=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 UHCYUVNJVPRFGF-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
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- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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Abstract
본 발명은 발광능이 우수한 신규의 화합물 및 이를 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel compound having excellent luminescence ability and an organic electroluminescent device having improved characteristics such as luminescence efficiency, driving voltage, and lifespan by including the same in one or more organic layers.
Description
본 발명은 신규한 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 전자 주입 및 수송능 등이 우수한 신규한 피리미딘 유도체 화합물 및 이를 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic luminescent compound and an organic electroluminescent device using the same, and more specifically, to a novel pyrimidine derivative compound having excellent electron injection and transport capabilities, and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the same in one or more organic layers.
1950년대 Bernanose의 유기 박막 발광 관측을 시점으로 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광 (electroluminescent, EL) 소자(이하, 간단히 '유기 EL 소자'로 칭함)에 대한 연구는 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 EL 소자가 제시되었다. 이후 고효율, 고수명의 유기 EL 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물 층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다. Starting with Bernanose's observation of organic thin film luminescence in the 1950s, research on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') led to the blue electroluminescence using anthracene single crystals in 1965, and in 1987, Tang proposed an organic EL device with a laminated structure divided into functional layers, a hole layer and a light-emitting layer. Since then, in order to create high-efficiency, long-life organic EL devices, the research has developed into the form of introducing each characteristic organic layer within the device, which has led to the development of specialized materials used for this.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때 유기물층으로 사용되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다. In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. At this time, the materials used in the organic layer can be classified into luminescent materials, hole injection materials, hole transport materials, electron transport materials, and electron injection materials according to their functions.
유기 EL 소자의 발광층 형성재료는 발광색에 따라 청색, 녹색, 적색 발광 재료로 구분될 수 있다. 그밖에, 보다 나은 천연색을 구현하기 위한 발광재료로 노란색 및 주황색 발광재료도 사용된다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도펀트 계를 사용할 수 있다. 도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 이러한 인광 재료의 개발은 이론적으로 형광에 비해 4배까지의 발광 효율을 향상시킬 수 있어 인광 도판트 뿐만 아니라 인광 호스트 재료들에 대해 관심이 집중되고 있다. The light-emitting layer forming materials of organic EL devices can be classified into blue, green, and red light-emitting materials according to the light-emitting color. In addition, yellow and orange light-emitting materials are also used as light-emitting materials to implement better natural colors. In addition, a host/dopant system can be used as a light-emitting material to increase color purity and light-emitting efficiency through energy transfer. The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of such phosphorescent materials can theoretically improve light-emitting efficiency by up to four times compared to fluorescence, so interest is focused on not only phosphorescent dopants but also phosphorescent host materials.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층으로는, 하기 화학식으로 표현된 NPB, BCP, Alq3 등이 널리 알려져 고, 발광 재료는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히 발광재료 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 재료로서는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색, 녹색, 적색 도판트 재료로 사용되고 있다. 현재까지는 CBP가 인광 호스트 재료로 우수한 특성을 나타내고 있다. Up to now, NPB, BCP, Alq 3 , etc. expressed by the following chemical formulas have been widely known as the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, and anthracene derivatives have been reported as fluorescent dopant/host materials as luminescent materials. In particular, among luminescent materials, metal complex compounds containing Ir, such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2 , etc., have been used as blue, green, and red dopant materials as phosphorescent materials that have a great advantage in terms of improving efficiency. Up to now, CBP has shown excellent properties as a phosphorescent host material.
그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아 유기 EL 소자에서의 수명 측면에서 만족할만한 수준이 되지 못하고 있다. However, although existing materials have advantages in terms of luminescence characteristics, they have low glass transition temperatures and very poor thermal stability, so they are not satisfactory in terms of lifespan in organic EL devices.
본 발명은 유기 전계 발광 소자에 적용할 수 있으며, 전자 주입 및 수송능 등이 모두 우수한 신규 유기 화합물을 제공하는 것을 목적으로 한다. The present invention can be applied to organic electroluminescent devices, and aims to provide a novel organic compound having excellent electron injection and transport capabilities.
또한, 본 발명은 상기 신규 유기 화합물을 포함하여 낮은 구동전압과 높은 발광효율을 나타내며 수명이 향상되는 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.In addition, another object of the present invention is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan, including the novel organic compound.
상기 목적을 달성하기 위하여 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.To achieve the above purpose, the present invention provides a compound represented by the following chemical formula 1.
[화학식 1][Chemical Formula 1]
여기서,Here,
L1 및 L2는 서로 동일하거나 상이하며, 단일결합, C6~C18의 아릴렌기 또는 핵원자수 5 내지 18의 헤테로아릴렌기이며,L 1 and L 2 are the same or different and are a single bond, an arylene group having C 6 to C 18 or a heteroarylene group having 5 to 18 nuclear atoms,
R1 및 R2는 서로 동일하거나 상이하며, 각각 독립적으로 C6~C60의 아릴기 또는 핵원자수 5 내지 60의 헤테로아릴기이며;R 1 and R 2 are the same or different, and each independently represents an aryl group having C 6 to C 60 or a heteroaryl group having 5 to 60 nuclear atoms;
Ar1 및 Ar2는 서로 상이하며, 각각 독립적으로 C6~C60의 아릴기 또는 핵원자수 5 내지 60의 헤테로아릴기이며, Ar 1 and Ar 2 are different from each other and are each independently an aryl group having C 6 to C 60 or a heteroaryl group having 5 to 60 nuclear atoms.
X1, X2 및 X3는 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 C(R3)이며, 적어도 2개 이상은 N이며;X 1 , X 2 and X 3 are the same or different, and each is independently N or C(R 3 ), and at least two are N;
R3는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택되고, R 3 are the same or different and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkylboron group, C 6 to C 60 arylborone group, C 6 to C Selected from the group consisting of an arylphosphine group of 60 , an arylphosphine oxide group of C 6 to C 60 , and an arylamine group of C 6 to C 60 ,
L1, L2의 아릴렌기 및 헤테로아릴렌기와 R1 내지 R3 및 Ar1 내지 Ar2의 아릴기 및 헤테로아릴기는 각각 독립적으로, 중주소, 시아노기, 할로겐, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기,C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상으로 치환될 수 있으며, 복수개의 치환기로 치환될 경우 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 , L 2 and the aryl group and heteroaryl group of R 1 to R 3 and Ar 1 to Ar 2 are each independently a deuterated group, a cyano group, a halogen, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 3 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C It may be substituted with at least one selected from the group consisting of an alkylboron group of 40 , an arylborone group of C 6 to C 60 , an arylphosphine group of C 6 to C 60 , an arylphosphine oxide group of C 6 to C 60 , and an arylamine group of C 6 to C 60 , and when substituted with multiple substituents, they may be the same as or different from each other.
또한, 본 발명은 (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자를 제공한다. In addition, the present invention provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the chemical formula 1.
본 발명에서 "알킬"은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkyl" means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
본 발명에서 "알케닐(alken일)"은 탄소-탄소 이중 결합을 1개 이상 가진탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vin일), 알릴(all일), 이소프로펜일(isopropen일), 2-부텐일(2-buten일) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkenyl" means a monovalent substituent derived from an unsaturated hydrocarbon having 2 to 40 carbon atoms and a straight or branched chain having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.
본 발명에서"알키닐(alkyn일)"은 탄소-탄소 삼중 결합을 1개 이상 가진탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethyn일), 2-프로파닐(2-propyn일) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkynyl" means a monovalent substituent derived from an unsaturated hydrocarbon having 2 to 40 carbon atoms and a straight or branched chain having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl and 2-propanyl.
본 발명에서 "아릴"은 단독 고리 또는 2이상의 고리가 조합된탄소수 6 내지 40의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms, which is a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.
본 발명에서 "헤테로아릴"은 핵원자수 5 내지 40의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함될 수 있다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리, 페녹사티에닐(phenoxathien일), 인돌리지닐(indolizin일), 인돌릴(indol일), 퓨리닐(purin일), 퀴놀릴(quinol일), 벤조티아졸(benzothiazole), 카바졸릴(carbazol일)과 같은 폴리사이클릭 고리 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included, and further, a form condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl.
본 발명에서 "아릴옥시"는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 40의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.
본 발명에서 "알킬옥시"는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.
본 발명에서 "아릴아민"은 탄소수 6 내지 40의 아릴로 치환된 아민을 의미한다.In the present invention, “arylamine” means an amine substituted with an aryl having 6 to 40 carbon atoms.
본 발명에서 "시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norborn일), 아다만틴(adamantine) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.
본 발명에서 "헤테로시클로알킬"은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.
본 발명에서 "알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, "아릴실릴"은 탄소수 5 내지 40의 아릴로 치환된 실릴을 의미한다.In the present invention, “alkylsilyl” means silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” means silyl substituted with aryl having 5 to 40 carbon atoms.
본 발명에서 "축합고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, “fused ring” means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.
본 발명의 화합물은 열적 안정성 및 발광 특성이 우수하기 때문에 유기 전계 발광 소자의 유기물층의 재료로 사용될 수 있다. Since the compound of the present invention has excellent thermal stability and luminescence characteristics, it can be used as a material for an organic layer of an organic electroluminescent device.
특히, 본 발명의 화합물을 전자 수송 재료로 사용할 경우, 종래의 호스트 재료에 비해 우수한 발광 성능, 낮은 구동전압, 높은 효율 및 장수명을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능 및 수명이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.In particular, when the compound of the present invention is used as an electron transport material, an organic electroluminescent device having superior luminescence performance, low driving voltage, high efficiency, and long lifespan compared to conventional host materials can be manufactured, and further, a full-color display panel with improved performance and lifespan can also be manufactured.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
1. 신규 유기 화합물1. New organic compounds
본 발명의 화합물 피리미딘계의 유기발광 화합물은 기존 전자 주입 및 수송 재료에 비해 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동 수명이 매우 우수할 뿐만 아니라 전력 효율의 상승을 유도하여 소비전력이 개선된 OLED소자를 제조할 수 있는 장점이 있다.The organic light-emitting compound of the pyrimidine series of compounds of the present invention has a high luminescence efficiency and excellent material life characteristics compared to existing electron injection and transport materials, so that not only is the operating life of the device very excellent, but also it induces an increase in power efficiency, so that an OLED device with improved power consumption can be manufactured.
구체적으로, 본 발명에서 제공하는 신규 유기 화합물은 하기 화학식 1로 표시되는 것을 특징으로 한다:Specifically, the novel organic compound provided in the present invention is characterized by being represented by the following chemical formula 1:
[화학식 1][Chemical Formula 1]
여기서,Here,
L1 및 L2는 서로 동일하거나 상이하며, 단일결합, C6~C18의 아릴렌기 또는 핵원자수 5 내지 18의 헤테로아릴렌기이며,L 1 and L 2 are the same or different and are a single bond, an arylene group having C 6 to C 18 or a heteroarylene group having 5 to 18 nuclear atoms,
R1 및 R2는 서로 동일하거나 상이하며, 각각 독립적으로 C6~C60의 아릴기 또는 핵원자수 5 내지 60의 헤테로아릴기이며;R 1 and R 2 are the same or different, and each independently represents an aryl group having C 6 to C 60 or a heteroaryl group having 5 to 60 nuclear atoms;
Ar1 및 Ar2는 서로 상이하며, 각각 독립적으로 C6~C60의 아릴기 또는 핵원자수 5 내지 60의 헤테로아릴기이며, Ar 1 and Ar 2 are different from each other and are each independently an aryl group having C 6 to C 60 or a heteroaryl group having 5 to 60 nuclear atoms.
X1, X2 및 X3는 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 C(R3)이며, 적어도 2개 이상은 N이며;X 1 , X 2 and X 3 are the same or different, and each is independently N or C(R 3 ), and at least two are N;
R3는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택되고, R 3 are the same or different and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkylboron group, C 6 to C 60 arylborone group, C 6 to C Selected from the group consisting of an arylphosphine group of 60 , an arylphosphine oxide group of C 6 to C 60 , and an arylamine group of C 6 to C 60 ,
L1, L2의 아릴렌기 및 헤테로아릴렌기와 R1 내지 R3 및 Ar1 내지 Ar2의 아릴기 및 헤테로아릴기는 각각 독립적으로, 중주소, 시아노기, 할로겐, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기,C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상으로 치환될 수 있으며, 복수개의 치환기로 치환될 경우 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 , L 2 and the aryl group and heteroaryl group of R 1 to R 3 and Ar 1 to Ar 2 are each independently a deuterated group, a cyano group, a halogen, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 3 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C It may be substituted with at least one selected from the group consisting of an alkylboron group of 40 , an arylborone group of C 6 to C 60 , an arylphosphine group of C 6 to C 60 , an arylphosphine oxide group of C 6 to C 60 , and an arylamine group of C 6 to C 60 , and when substituted with multiple substituents, they may be the same as or different from each other.
피리미딘계 화합물에 페난트렌이나 카바졸이 도입된 유도체는 삼중항 에너지가 높고 안정한 구조를 기본으로 하는 코어(Core)로써 특히 페난트렌 또는 카바졸의 작용기를 치환하였을 전자 수송 능력이 향상되어 전력 효율의 상승을 유도하는 구조로 효율 특성을 극대화 할 수 있는 전자 주입 및 수송 재료로써의 장점이 있다. 특히 R1, R2, Ar1 및 Ar2위치에 방향족 고리 및 헤테로 방향족 고리가 각각 독립적으로 치환되었을 때 평면구조를 개선하여 열적 안정도를 높일 뿐만 아니라 전자 이동을 좋게 하여 전자 수송층 재료로 적합하다.Derivatives in which phenanthrene or carbazole is introduced into pyrimidine compounds have a core based on a high triplet energy and a stable structure, and especially when the functional group of phenanthrene or carbazole is substituted, the electron transport ability is improved, leading to an increase in power efficiency, and thus there is an advantage as an electron injection and transport material that can maximize efficiency characteristics. In particular, when an aromatic ring and a heteroaromatic ring are independently substituted at the R 1 , R 2 , Ar 1 , and Ar 2 positions, not only does it improve the planar structure, thereby increasing thermal stability, but it also improves electron movement, making it suitable as an electron transport layer material.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1 및 Ar2는 서로 상이하며, 각각 독립적으로 C6~C60의 아릴기인 것을 특징으로 할 수 있다.According to a preferred embodiment of the present invention, Ar 1 and Ar 2 are different from each other and can be characterized in that they are each independently a C 6 to C 60 aryl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 X1 및 X2는 각각 독립적으로 N이고, X3는 N 또는 C(R3)에서 선택되고, 상기 Ar1 및 Ar2는 서로 상이하며, 각각 독립적으로 페닐 또는 바이페닐에서 선택될 수 있다.According to a preferred embodiment of the present invention, X 1 and X 2 are each independently N, X 3 is selected from N or C(R 3 ), and Ar 1 and Ar 2 are different from each other and can each be independently selected from phenyl or biphenyl.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R1 및 R2는 서로 동일하거나 상이하며, 각각 독립적으로 C6~C60의 아릴기 또는 핵원자수 5 내지 60의 헤테로아릴기에서 선택될 수 있으며, 바람직하게는 R1 또는 R2 중 적어도 하나는 하기 화학식 2 내지 5의 치환기로 이루어진 군으로부터 선택되는 것일 수 있다:According to a preferred embodiment of the present invention, R 1 and R 2 are the same as or different from each other, and may each be independently selected from an aryl group having C 6 to C 60 or a heteroaryl group having 5 to 60 nuclear atoms, and preferably, at least one of R 1 or R 2 may be selected from the group consisting of substituents of the following chemical formulas 2 to 5:
[화학식 2][Chemical formula 2]
[화학식 3][Chemical Formula 3]
[화학식 4][Chemical Formula 4]
[화학식 5][Chemical Formula 5]
여기서,Here,
*는 상기 화학식 1에 결합되는 부분을 의미하고;* indicates a part that is bonded to the chemical formula 1;
X4 내지 X26은 서로 동일하고 상이하며, 각각 독립적으로 N 또는 C(R5)이며,X 4 to X 26 are identical and different from each other, and each is independently N or C(R 5 ),
R5는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택되고, R 5 are the same or different and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkylboron group, C 6 to C 60 arylborone group, C 6 to C 60 Selected from the group consisting of an arylphosphine group of 60 , an arylphosphine oxide group of C 6 to C 60 , and an arylamine group of C 6 to C 60 ,
R5의 알킬기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기,C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택된 1종 이상으로 치환될 수 있으며, 복수개의 치환기로 치환될 경우 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of R 5 are each independently, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 3 to C 40 It may be substituted with at least one selected from the group consisting of an alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylamine group , and when substituted with multiple substituents, they may be the same as or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 본 발명의 화학식1로 표시되는 화합물은 보다 구체적으로 아래의 화합물로 이루어진 군에서 선택될 수 있으나, 이에 한정되는 것은 아니다.According to a preferred embodiment of the present invention, the compound represented by the chemical formula 1 of the present invention may be more specifically selected from the group consisting of the compounds below, but is not limited thereto.
2. 유기 전계 발광 소자2. Organic electroluminescent devices
한편, 본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(유기 EL 소자)에 관한 것이다.Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising a compound represented by chemical formula 1 according to the present invention.
보다 구체적으로, 본 발명에 따른 유기 전계 발광 소자는 양극(anode), 음극(cathode) 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.More specifically, the organic electroluminescent device according to the present invention comprises an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, and at least one of the one or more organic layers comprises a compound represented by the chemical formula 1. At this time, the compound may be used alone, or two or more may be mixed and used.
상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층 및 전자주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 바람직하게는 상기 화학식 1의 화합물을 포함하는 유기물층은 전자수송층일 수 있다.The organic layer of one or more layers may be at least one of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and an electron injection layer, and at least one of the organic layers may include a compound represented by the chemical formula 1. Preferably, the organic layer including the compound of the chemical formula 1 may be an electron transport layer.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 기판, 양극, 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층 및 전자주입층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 정공수송층, 전자저지층, 발광보조층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 한편 상기 전자수송층 위에는 전자주입층이 추가로 적층될 수 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, but may have a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially laminated. At this time, at least one of the hole injection layer, the hole transport layer, the light-emitting auxiliary layer, the light-emitting layer, the electron transport layer, and the electron injection layer may include a compound represented by the chemical formula 1, and preferably, the hole transport layer, the electron blocking layer, and the light-emitting auxiliary layer may include a compound represented by the chemical formula 1. Meanwhile, an electron injection layer may be additionally laminated on the electron transport layer.
본 발명의 유기 전계 발광 소자의 구조는 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.
본 발명의 유기 전계 발광 소자는 상기 유기물층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는, 당업계에 공지된 재료 및 방법으로 유기물층 및 전극을 형성하여 제조할 수 있다.The organic electroluminescent device of the present invention can be manufactured by forming organic layers and electrodes using materials and methods known in the art, except that at least one of the organic layers includes a compound represented by the chemical formula 1.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지는 않는다.The above organic layer can be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명의 유기 전계 발광 소자 제조 시 사용되는 기판은 특별히 한정되지 않으나, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등을 사용할 수 있다.The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, but a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and sheet, etc. can be used.
또, 양극 물질로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등을 들 수 있으나, 이에 한정되지는 않는다.In addition, the anode material may include, but is not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black.
또, 음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등을 들 수 있으나, 이에 한정되지는 않는다.In addition, cathode materials may include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayered materials such as LiF/Al or LiO 2 /Al.
또한, 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질을 사용할 수 있다.In addition, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and conventional materials known in the art can be used.
이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail through examples. However, the following examples are only intended to illustrate the present invention, and the present invention is not limited to the following examples.
[[ 준비예Preparation 1]1]
4-([1,1'-4-([1,1'- 바이페닐Biphenyl ]-4-일)-6-(3-]-4-day)-6-(3- 브로모Bromo -5-(피리딘-3-일)페닐)-2--5-(pyridin-3-yl)phenyl)-2- 페닐피리미딘의Phenylpyrimidine 합성Synthesis
4-([1,1'-바이페닐]-4-일)-6-(3,5-디브로모페닐)-2-페닐피리미딘 4-([1,1'-biphenyl]-4-yl)-6-(3,5-dibromophenyl)-2-phenylpyrimidine
50g(92.2mmol)과 피리딘-3-일보로닉 산 11.3g(92.2mmol)에 1,4-디옥산 250 mL를 가하였다. Pd(PPh3)4 5.32g(4.61mmol), K2CO3 31.85g(230mol)을 첨가 후 120에서 24시간 가열 환류하였다. 상온으로 온도를 냉각하고 반응액에 염화암모늄 수용액 500 mL로 반응을 종결시켰다. 혼합액을 M.C 500 mL로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 30g(수율 61%)을 얻었다. 1H-NMR: 9.24(s, 1H), 8.70(d, 1H), 8.42~8.30(m, 5H), 8.24(s, 1H), 7.85~7.77(m, 3H), 7.75(m, 2H); 7.55~7.41(m, 9H), HRMS [M]+: 540.4650 g (92.2 mmol) of pyridin-3-ylboronic acid and 11.3 g (92.2 mmol) of 1,4-dioxane were added to 250 mL. After 5.32 g (4.61 mmol) of Pd(PPh 3 ) 4 and 31.85 g (230 mol) of K 2 CO 3 were added, the mixture was heated and refluxed at 120 °C for 24 hours. The temperature was cooled to room temperature, and the reaction solution was quenched with 500 mL of ammonium chloride aqueous solution. The mixture was extracted with 500 mL of MC, and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 30 g (yield 61%) of the target compound. 1H-NMR: 9.24(s, 1H), 8.70(d, 1H), 8.42~8.30(m, 5H), 8.24(s, 1H), 7.85~7.77(m, 3H), 7.75(m, 2H); 7.55~7.41(m, 9H), HRMS [M] + : 540.46
[[ 준비예Preparation 2]2]
4-([1,1'-4-([1,1'- 바이페닐Biphenyl ]-4-일)-6-(3-]-4-day)-6-(3- 브로모Bromo -5-(피리딘-4-일)페닐)-2--5-(pyridin-4-yl)phenyl)-2- 페닐피리미딘의Phenylpyrimidine 합성Synthesis
반응물로 피리딘-4-일보로닉 산을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 26g을 얻었다; HRMS [M]+: 540.46The same procedure as in [Preparation Example 1] was followed, except that pyridin-4-ylboronic acid was used as a reactant, to obtain 26 g of the target compound; HRMS [M]+: 540.46
[[ 준비예Preparation 3]3]
8-(3-(6-([1,1'-8-(3-(6-([1,1'- 바이페닐Biphenyl ]-4-일)-2-]-4-day)-2- 페닐피리미딘Phenylpyrimidine -4-일)-5--4-day)-5- 브로모페닐Bromophenyl )퀴놀린의 합성)Synthesis of quinoline
반응물로 퀴놀린-8-일보로닉 산을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 31g을 얻었다; HRMS [M]+: 590.52The same procedure as in [Preparation Example 1] was followed, except that quinolin-8-ylboronic acid was used as a reactant, to obtain 31 g of the target compound; HRMS [M]+: 590.52
[[ 준비예Preparation 4]4]
4-([1,1'-4-([1,1'- 바이페닐Biphenyl ]-4-일)-6-(5-]-4-day)-6-(5- 브로모Bromo -4'-(피리딘-3-일)-[1,1'--4'-(pyridin-3-yl)-[1,1'- 바이페닐Biphenyl ]-3-일)-2-페닐피리미딘의 합성]-3-yl)-2-phenylpyrimidine synthesis
반응물로 (4-(피리딘-3-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 35g을 얻었다; HRMS [M]+: 616.56The same procedure as in [Preparation Example 1] was followed, except that (4-(pyridin-3-yl)phenyl)boronic acid was used as a reactant, to obtain 35 g of the target compound; HRMS [M]+: 616.56
[[ 준비예Preparation 5]5]
2-(3-(6-([1,1'-2-(3-(6-([1,1'- 바이페닐Biphenyl ]-4-일)-2-]-4-day)-2- 페닐피리미딘Phenylpyrimidine -4-일)-5--4-day)-5- 브로모페닐Bromophenyl )-1,10-페난트롤린의 합성)-1,10-phenanthroline synthesis
반응물로 2-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-1,10-페난트롤린을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 31g을 얻었다; HRMS [M]+: 641.57The same procedure as in [Preparation Example 1] was followed, except that 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline was used as a reactant, to obtain 31 g of the target compound; HRMS [M]+: 641.57
[[ 준비예Preparation 6]6]
4-([1,1'-4-([1,1'- 바이페닐Biphenyl ]-4-일)-6-(3-]-4-day)-6-(3- 브로모Bromo -5-(피리딘-3-일)페닐)-2--5-(pyridin-3-yl)phenyl)-2- 페닐피리미딘의Phenylpyrimidine 합성Synthesis
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3,5-디브로모페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 23g을 얻었다; HRMS [M]+: 541.45The same procedure as in [Preparation Example 1] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3,5-dibromophenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 23 g of the target compound; HRMS [M]+: 541.45
[[ 준비예Preparation 7]7]
4-([1,1'-4-([1,1'- 바이페닐Biphenyl ]-4-일)-6-(3-]-4-day)-6-(3- 브로모Bromo -5-(피리딘-4-일)페닐)-2--5-(pyridin-4-yl)phenyl)-2- 페닐피리미딘의Phenylpyrimidine 합성Synthesis
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3,5-디브로모페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [준비예 2]과 동일한 과정을 수행하여 목적 화합물 22g을 얻었다; HRMS [M]+: 541.45The same procedure as in [Preparation Example 2] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3,5-dibromophenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 22 g of the target compound; HRMS [M]+: 541.45
[[ 준비예Preparation 8]8]
8-(3-(6-([1,1'-8-(3-(6-([1,1'- 바이페닐Biphenyl ]-4-일)-2-]-4-day)-2- 페닐피리미딘Phenylpyrimidine -4-일)-5--4-day)-5- 브로모페닐Bromophenyl )퀴놀린의 합성)Synthesis of quinoline
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3,5-디브로모페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [준비예 3]과 동일한 과정을 수행하여 목적 화합물 26g을 얻었다; HRMS [M]+: 591.51The same procedure as in [Preparation Example 3] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3,5-dibromophenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 26 g of the target compound; HRMS [M]+: 591.51
[[ 준비예Preparation 9]9]
4-([1,1'-4-([1,1'- 바이페닐Biphenyl ]-4-일)-6-(5-]-4-day)-6-(5- 브로모Bromo -4'-(피리딘-3-일)-[1,1'--4'-(pyridin-3-yl)-[1,1'- 바이페닐Biphenyl ]-3-일)-2-페닐피리미딘의 합성]-3-yl)-2-phenylpyrimidine synthesis
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3,5-디브로모페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [준비예 4]과 동일한 과정을 수행하여 목적 화합물 29g을 얻었다; HRMS [M]+: 615.55The same procedure as in [Preparation Example 4] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3,5-dibromophenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 29 g of the target compound; HRMS [M]+: 615.55
[[ 준비예Preparation 10]10]
2-(3-(6-([1,1'-2-(3-(6-([1,1'- 바이페닐Biphenyl ]-4-일)-2-]-4-day)-2- 페닐피리미딘Phenylpyrimidine -4-일)-5--4-day)-5- 브로모페닐Bromophenyl )-1,10-페난트롤린의 합성)-1,10-phenanthroline synthesis
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3,5-디브로모페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [준비예 5]과 동일한 과정을 수행하여 목적 화합물 28g을 얻었다; HRMS [M]+: 640.56The same procedure as in [Preparation Example 5] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3,5-dibromophenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 28 g of the target compound; HRMS [M]+: 640.56
[[ 합성예Synthetic example 1] Mat 1의 합성1] Synthesis of Mat 1
4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-3-일)페닐)-2-페닐피리미딘 5g(9.25mmol)과 페닐보로닉 산 1.24g(10.17mmol)에 1,4-디옥산 250 mL를 가하였다. Pd(PPh3)4 0.53g(0.46mmol), K2CO3 3.19g(23.1mol)을 첨가 후 120에서 24시간 가열환류하였다. 상온으로 온도를 냉각하고 반응액에 염화암모늄 수용액 500 mL로 반응을 종결시켰다. 혼합액을 M.C 200 mL로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 4.37g(수율 88%)을 얻었다. 1H-NMR: 9.24(s, 1H), 8.70(d, 1H), 8.42~8.30(m, 5H), 8.23(s, 1H), 8.04(s, 3H), 7.85(m, 2H), 7.75(m, 2H); 7.51~7.41(m, 10H), HRMS [M]+: 537.675 g (9.25 mmol) of 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-3-yl)phenyl)-2-phenylpyrimidine and 1.24 g (10.17 mmol) of phenylboronic acid were added to 250 mL of 1,4-dioxane. After adding 0.53 g (0.46 mmol) of Pd(PPh 3 ) 4 and 3.19 g (23.1 mol) of K 2 CO 3 , the mixture was heated and refluxed at 120 °C for 24 hours. The temperature was cooled to room temperature, and the reaction was terminated with 500 mL of ammonium chloride aqueous solution. The mixture was extracted with 200 mL of MC and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 4.37 g (yield 88%) of the target compound. 1H-NMR: 9.24 (s, 1H), 8.70 (d, 1H), 8.42~8.30 (m, 5H), 8.23 (s, 1H), 8.04 (s, 3H), 7.85 (m, 2H), 7.75 (m, 2H); 7.51~7.41 (m, 10H), HRMS [M] + : 537.67
[[ 합성예Synthetic example 2] Mat 2의 합성2] Synthesis of Mat 2
반응물로 나프탈렌-2-일보로닉 산을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다; HRMS [M]+: 587.73The same procedure as in [Synthetic Example 1] was followed, except that naphthalen-2-ylboronic acid was used as a reactant, to obtain 5.1 g of the target compound; HRMS [M]+: 587.73
[[ 합성예Synthetic example 3] Mat 3의 합성3] Synthesis of Mat 3
반응물로 나프탈렌-1-일보로닉 산을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다; HRMS [M]+: 587.73The same procedure as in [Synthetic Example 1] was followed, except that naphthalen-1-ylboronic acid was used as a reactant, to obtain 4.8 g of the target compound; HRMS [M]+: 587.73
[[ 합성예Synthetic example 4] Mat 4의 합성4] Synthesis of Mat 4
반응물로 페난트렌-9-일보로닉 산을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다; HRMS [M]+: 637.79The same procedure as in [Synthetic Example 1] was followed, except that phenanthren-9-ylboronic acid was used as a reactant, to obtain 5.6 g of the target compound; HRMS [M]+: 637.79
[[ 합성예Synthetic example 5] Mat 5의 합성5] Synthesis of Mat 5
반응물로 안트라센-9-일보로닉 산을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다; HRMS [M]+: 637.79The same procedure as in [Synthetic Example 1] was followed, except that anthracene-9-ylboronic acid was used as a reactant, to obtain 5.5 g of the target compound; HRMS [M]+: 637.79
[[ 합성예Synthetic example 6] Mat 6의 합성6] Synthesis of Mat 6
반응물로 (10-페닐안트라센-9-일)보로닉 산을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다; HRMS [M]+: 713.88The same procedure as in [Synthetic Example 1] was followed, except that (10-phenylanthracen-9-yl)boronic acid was used as a reactant, to obtain 6.9 g of the target compound; HRMS [M]+: 713.88
[[ 합성예Synthetic example 7] Mat 7의 합성7] Synthesis of Mat 7
반응물로 트리페닐렌-2-일보로닉 산을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다; HRMS [M]+: 687.85The same procedure as in [Synthetic Example 1] was followed, except that triphenylene-2-ylboronic acid was used as a reactant, to obtain 5.4 g of the target compound; HRMS [M]+: 687.85
[[ 합성예Synthetic example 8] Mat 8의 합성8] Synthesis of Mat 8
반응물로 (3a1,6-디하이드로피렌-1-일)보로닉 산을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.0g을 얻었다; HRMS [M]+: 661.81The same procedure as in [Synthetic Example 1] was followed, except that (3a1,6-dihydropyren-1-yl)boronic acid was used as a reactant, to obtain 6.0 g of the target compound; HRMS [M]+: 661.81
[[ 합성예Synthetic example 9] Mat 9의 합성9] Synthesis of Mat 9
반응물로 (9,9-디메틸-9H-플로우렌-3-일)보로닉 산을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다; HRMS [M]+: 653.83The same procedure as in [Synthetic Example 1] was followed, except that (9,9-dimethyl-9H-fluoren-3-yl)boronic acid was used as a reactant, to obtain 5.8 g of the target compound; HRMS [M]+: 653.83
[[ 합성예Synthetic example 10] Mat 10의 합성10] Synthesis of Mat 10
반응물로 (9-페닐-9H-카바졸-3-일)보로닉 산을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 7g을 얻었다; HRMS [M]+: 702.86The same procedure as in [Synthetic Example 1] was followed, except that (9-phenyl-9H-carbazol-3-yl)boronic acid was used as a reactant, to obtain 7 g of the target compound; HRMS [M]+: 702.86
[[ 합성예Synthetic example 11] Mat 11의 합성11] Synthesis of Mat 11
반응물로 디벤조[b,d]퓨란-2-일보로닉 산을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다; HRMS [M]+: 627.75The same procedure as in [Synthetic Example 1] was followed, except that dibenzo[b,d]furan-2-ylboronic acid was used as a reactant, to obtain 5.6 g of the target compound; HRMS [M]+: 627.75
[[ 합성예Synthetic example 12] Mat 12의 합성12] Synthesis of Mat 12
4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-3-일)페닐)-2-페닐피리미딘 5g(9.25mmol)과 카바졸 1.7g(10.17mmol)에 자일렌 250 mL를 가하였다. Pd2(dba)3 0.42g (0.46mmol), Xphos 0.44g(0.92mmol), NaOtBu 2.2g(23.1mol)을 첨가 후 120에서 24시간 가열환류하였다. 상온으로 온도를 냉각하고 반응액에 염화암모늄 수용액 500 mL로 반응을 종결시켰다. 혼합액을 M.C 500 mL로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 4.46g(수율 77%)을 얻었다. 1H-NMR: 9.24(s, 1H), 8.70(d, 1H), 8.55(d, 1H), 8.42~8.19(m, 9H), 7.9~7.85(m, 4H), 7.50~7.16(m, 12H); HRMS [M]+: 626.765 g (9.25 mmol) of 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-3-yl)phenyl)-2-phenylpyrimidine and 1.7 g (10.17 mmol) of carbazole were added to 250 mL of xylene. After adding 0.42 g (0.46 mmol) of Pd 2 (dba) 3 , 0.44 g (0.92 mmol) of Xphos, and 2.2 g (23.1 mol) of NaOtBu, the mixture was heated and refluxed at 120 °C for 24 hours. The temperature was cooled to room temperature, and the reaction was terminated with 500 mL of ammonium chloride aqueous solution. The mixture was extracted with 500 mL of MC and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 4.46 g (yield 77%) of the target compound. 1H-NMR: 9.24 (s, 1H), 8.70 (d, 1H), 8.55 (d, 1H), 8.42~8.19 (m, 9H), 7.9~7.85 (m, 4H), 7.50~7.16 (m, 12H); HRMS [M] + : 626.76
[[ 합성예Synthetic example 13] Mat 13의 합성13] Synthesis of Mat 13
반응물로 3-페닐-9H-카바졸을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다; HRMS [M]+: 702.86The same procedure as in [Synthetic Example 12] was followed, except that 3-phenyl-9H-carbazole was used as a reactant, to obtain 5.9 g of the target compound; HRMS [M]+: 702.86
[[ 합성예Synthetic example 14] Mat 14의 합성14] Synthesis of Mat 14
반응물로 2-(디벤조[b,e][1,4]디옥신-2-일)-4,4,5,5-테트라메틸-1,3,2-디옥사보로란을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다; HRMS [M]+: 643.75The same procedure as in [Synthetic Example 1] was followed, except that 2-(dibenzo[b,e][1,4]dioxin-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used as a reactant, to obtain 6.1 g of the target compound; HRMS [M]+: 643.75
[[ 합성예Synthetic example 15] Mat 15의 합성15] Synthesis of Mat 15
반응물로 10H-페녹사진을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다; HRMS [M]+: 642.76The same procedure as in [Synthetic Example 12] was followed except that 10H-phenoxazine was used as a reactant, to obtain 5.2 g of the target compound; HRMS [M]+: 642.76
[[ 합성예Synthetic example 16] Mat 16의 합성16] Synthesis of Mat 16
반응물로 2-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.3g을 얻었다; HRMS [M]+: 639.76The same procedure as in [Synthetic Example 1] was followed, except that 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline was used as a reactant, to obtain 4.3 g of the target compound; HRMS [M]+: 639.76
[[ 합성예Synthetic example 17] Mat 17의 합성17] Synthesis of Mat 17
반응물로 퀴놀린-8-일보로닉 산을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다; HRMS [M]+: 588.71The same procedure as in [Synthetic Example 1] was followed, except that quinolin-8-ylboronic acid was used as a reactant, to obtain 5.0 g of the target compound; HRMS [M]+: 588.71
[[ 합성예Synthetic example 18] Mat 18의 합성18] Synthesis of Mat 18
반응물로 (4-(피리딘-3-일)페닐)보로닉 산을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다; HRMS [M]+: 614.75The same procedure as in [Synthetic Example 1] was followed, except that (4-(pyridin-3-yl)phenyl)boronic acid was used as a reactant, to obtain 6.5 g of the target compound; HRMS [M]+: 614.75
[[ 합성예Synthetic example 19] Mat 19의 합성19] Synthesis of Mat 19
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 3.2g을 얻었다; HRMS [M]+: 537.67The same procedure as in [Synthetic Example 1] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 3.2 g of the target compound; HRMS [M]+: 537.67
[[ 합성예Synthetic example 20] Mat 20의 합성20] Synthesis of Mat 20
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 2.8g을 얻었다; HRMS [M]+: 587.73The same procedure as in [Synthetic Example 2] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 2.8 g of the target compound; HRMS [M]+: 587.73
[[ 합성예Synthetic example 21] Mat 21의 합성21] Synthesis of Mat 21
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 3.2g을 얻었다; HRMS [M]+: 587.73The same procedure as in [Synthetic Example 3] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 3.2 g of the target compound; HRMS [M]+: 587.73
[[ 합성예Synthetic example 22] Mat 22의 합성22] Synthesis of Mat 22
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 3.0g을 얻었다; HRMS [M]+: 637.79The same procedure as in [Synthetic Example 4] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 3.0 g of the target compound; HRMS [M]+: 637.79
[[ 합성예Synthetic example 23] Mat 23의 합성23] Synthesis of Mat 23
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다; HRMS [M]+: 637.79The same procedure as in [Synthetic Example 5] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 4.2 g of the target compound; HRMS [M]+: 637.79
[[ 합성예Synthetic example 24] Mat 24의 합성24] Synthesis of Mat 24
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다; HRMS [M]+: 713.88The same procedure as in [Synthetic Example 6] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 5.2 g of the target compound; HRMS [M]+: 713.88
[[ 합성예Synthetic example 25] Mat 25의 합성25] Synthesis of Mat 25
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다; HRMS [M]+: 687.85The same procedure as in [Synthetic Example 7] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 4.8 g of the target compound; HRMS [M]+: 687.85
[[ 합성예Synthetic example 26] Mat 26의 합성26] Synthesis of Mat 26
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 3.3g을 얻었다; HRMS [M]+: 661.81The same procedure as in [Synthetic Example 8] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 3.3 g of the target compound; HRMS [M]+: 661.81
[[ 합성예Synthetic example 27] Mat 27의 합성27] Synthesis of Mat 27
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.6g을 얻었다; HRMS [M]+: 653.83The same procedure as in [Synthetic Example 9] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 4.6 g of the target compound; HRMS [M]+: 653.83
[[ 합성예Synthetic example 28] Mat 28의 합성28] Synthesis of Mat 28
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.3g을 얻었다; HRMS [M]+: 702.86The same procedure as in [Synthetic Example 10] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 4.3 g of the target compound; HRMS [M]+: 702.86
[[ 합성예Synthetic example 29] Mat 29의 합성29] Synthesis of Mat 29
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 3.3g을 얻었다; HRMS [M]+: 627.75The same procedure as in [Synthetic Example 11] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 3.3 g of the target compound; HRMS [M]+: 627.75
[[ 합성예Synthetic example 30] Mat 30의 합성30] Synthesis of Mat 30
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 2.5g을 얻었다; HRMS [M]+: 626.76The same procedure as in [Synthetic Example 12] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 2.5 g of the target compound; HRMS [M]+: 626.76
[[ 합성예Synthetic example 31] Mat 31의 합성31] Synthesis of Mat 31
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 13]과 동일한 과정을 수행하여 목적 화합물 2.8g을 얻었다; HRMS [M]+: 702.86The same procedure as in [Synthetic Example 13] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 2.8 g of the target compound; HRMS [M]+: 702.86
[[ 합성예Synthetic example 32] Mat 32의 합성32] Synthesis of Mat 32
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 14]과 동일한 과정을 수행하여 목적 화합물 2.1g을 얻었다; HRMS [M]+: 643.75The same procedure as in [Synthetic Example 14] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 2.1 g of the target compound; HRMS [M]+: 643.75
[[ 합성예Synthetic example 33] Mat 33의 합성33] Synthesis of Mat 33
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 15]과 동일한 과정을 수행하여 목적 화합물 1.6g을 얻었다; HRMS [M]+: 642.76The same procedure as in [Synthetic Example 15] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 1.6 g of the target compound; HRMS [M]+: 642.76
[[ 합성예Synthetic example 34] Mat 34의 합성34] Synthesis of Mat 34
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 16]과 동일한 과정을 수행하여 목적 화합물 3.0g을 얻었다; HRMS [M]+: 639.76The same procedure as in [Synthetic Example 16] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 3.0 g of the target compound; HRMS [M]+: 639.76
[[ 합성예Synthetic example 35] Mat 35의 합성35] Synthesis of Mat 35
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 17]과 동일한 과정을 수행하여 목적 화합물 3.6g을 얻었다; HRMS [M]+: 588.71The same procedure as in [Synthetic Example 17] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 3.6 g of the target compound; HRMS [M]+: 588.71
[[ 합성예Synthetic example 36] Mat 36의 합성36] Synthesis of Mat 36
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-4-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 18]과 동일한 과정을 수행하여 목적 화합물 3.7g을 얻었다; HRMS [M]+: 614.75The same procedure as in [Synthetic Example 18] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-4-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 3.7 g of the target compound; HRMS [M]+: 614.75
[[ 합성예Synthetic example 37] Mat 37의 합성37] Synthesis of Mat 37
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다; HRMS [M]+: 587.73The same procedure as in [Synthetic Example 1] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 4.5 g of the target compound; HRMS [M]+: 587.73
[[ 합성예Synthetic example 38] Mat 38의 합성38] Synthesis of Mat 38
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 4.3g을 얻었다; HRMS [M]+: 637.79The same procedure as in [Synthetic Example 2] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 4.3 g of the target compound; HRMS [M]+: 637.79
[[ 합성예Synthetic example 39] Mat 39의 합성39] Synthesis of Mat 39
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 3.8g을 얻었다; HRMS [M]+: 637.79The same procedure as in [Synthetic Example 3] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 3.8 g of the target compound; HRMS [M]+: 637.79
[[ 합성예Synthetic example 40] Mat 40의 합성40] Synthesis of Mat 40
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다; HRMS [M]+: 687.85The same procedure as in [Synthetic Example 4] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 4.9 g of the target compound; HRMS [M]+: 687.85
[[ 합성예Synthetic example 41] Mat 41의 합성41] Synthesis of Mat 41
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다; HRMS [M]+: 687.85The same procedure as in [Synthetic Example 5] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 4.8 g of the target compound; HRMS [M]+: 687.85
[[ 합성예Synthetic example 42] Mat 42의 합성42] Synthesis of Mat 42
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다; HRMS [M]+: 763.94The same procedure as in [Synthetic Example 6] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 5.1 g of the target compound; HRMS [M]+: 763.94
[[ 합성예Synthetic example 43] Mat 43의 합성43] Synthesis of Mat 43
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다; HRMS [M]+: 737.91The same procedure as in [Synthetic Example 7] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 4.7 g of the target compound; HRMS [M]+: 737.91
[[ 합성예Synthetic example 44] Mat 44의 합성44] Synthesis of Mat 44
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 6.0g을 얻었다; HRMS [M]+: 711.87The same procedure as in [Synthetic Example 8] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 6.0 g of the target compound; HRMS [M]+: 711.87
[[ 합성예Synthetic example 45] Mat 45의 합성45] Synthesis of Mat 45
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다; HRMS [M]+: 703.89The same procedure as in [Synthetic Example 9] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 5.3 g of the target compound; HRMS [M]+: 703.89
[[ 합성예Synthetic example 46] Mat 46의 합성46] Synthesis of Mat 46
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다; HRMS [M]+: 752.92The same procedure as in [Synthetic Example 10] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 4.9 g of the target compound; HRMS [M]+: 752.92
[[ 합성예Synthetic example 47] Mat 47의 합성47] Synthesis of Mat 47
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 3.8g을 얻었다; HRMS [M]+: 677.81The same procedure as in [Synthetic Example 11] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 3.8 g of the target compound; HRMS [M]+: 677.81
[[ 합성예Synthetic example 48] Mat 48의 합성48] Synthesis of Mat 48
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 3.6g을 얻었다; HRMS [M]+: 676.82The same procedure as in [Synthetic Example 12] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 3.6 g of the target compound; HRMS [M]+: 676.82
[[ 합성예Synthetic example 49 Mat 49의 합성49 Mat 49 Synthesis
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 13]과 동일한 과정을 수행하여 목적 화합물 4.0g을 얻었다; HRMS [M]+: 752.92The same procedure as in [Synthetic Example 13] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 4.0 g of the target compound; HRMS [M]+: 752.92
[[ 합성예Synthetic example 50] Mat 50의 합성50] Synthesis of Mat 50
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 14]과 동일한 과정을 수행하여 목적 화합물 3.2g을 얻었다; HRMS [M]+: 693.81The same procedure as in [Synthetic Example 14] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 3.2 g of the target compound; HRMS [M]+: 693.81
[[ 합성예Synthetic example 51] Mat 51의 합성51] Synthesis of Mat 51
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 15]과 동일한 과정을 수행하여 목적 화합물 2.7g을 얻었다; HRMS [M]+: 692.82The same procedure as in [Synthetic Example 15] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 2.7 g of the target compound; HRMS [M]+: 692.82
[[ 합성예Synthetic example 52] Mat 52의 합성52] Synthesis of Mat 52
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 16]과 동일한 과정을 수행하여 목적 화합물 3.0g을 얻었다; HRMS [M]+: 689.82The same procedure as in [Synthetic Example 16] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 3.0 g of the target compound; HRMS [M]+: 689.82
[[ 합성예Synthetic example 53] Mat 53의 합성53] Synthesis of Mat 53
반응물로 8-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 18]과 동일한 과정을 수행하여 목적 화합물 3.1g을 얻었다; HRMS [M]+: 664.81The same procedure as in [Synthetic Example 18] was followed, except that 8-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 3.1 g of the target compound; HRMS [M]+: 664.81
[[ 합성예Synthetic example 54] Mat 54의 합성54] Synthesis of Mat 54
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다; HRMS [M]+: 613.76The same procedure as in [Synthetic Example 1] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 5.5 g of the target compound; HRMS [M]+: 613.76
[[ 합성예Synthetic example 55] Mat 55의 합성55] Synthesis of Mat 55
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다; HRMS [M]+: 663.82The same procedure as in [Synthetic Example 2] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 5.8 g of the target compound; HRMS [M]+: 663.82
[[ 합성예Synthetic example 56] Mat 56의 합성56] Synthesis of Mat 56
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다; HRMS [M]+: 663.82The same procedure as in [Synthetic Example 3] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 5.1 g of the target compound; HRMS [M]+: 663.82
[[ 합성예Synthetic example 57] Mat 57의 합성57] Synthesis of Mat 57
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다; HRMS [M]+: 713.88The same procedure as in [Synthetic Example 4] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 6.7 g of the target compound; HRMS [M]+: 713.88
[[ 합성예Synthetic example 58] Mat 58의 합성58] Synthesis of Mat 58
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다; HRMS [M]+: 713.88The same procedure as in [Synthetic Example 5] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 6.1 g of the target compound; HRMS [M]+: 713.88
[[ 합성예Synthetic example 59] Mat 59의 합성59] Synthesis of Mat 59
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다; HRMS [M]+: 789.98The same procedure as in [Synthetic Example 6] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 6.6 g of the target compound; HRMS [M]+: 789.98
[[ 합성예Synthetic example 60] Mat 60의 합성60] Synthesis of Mat 60
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 6.0g을 얻었다; HRMS [M]+: 763.94The same procedure as in [Synthetic Example 7] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 6.0 g of the target compound; HRMS [M]+: 763.94
[[ 합성예Synthetic example 61] Mat 61의 합성61] Synthesis of Mat 61
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다; HRMS [M]+: 737.91The same procedure as in [Synthetic Example 8] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 5.7 g of the target compound; HRMS [M]+: 737.91
[[ 합성예Synthetic example 62] Mat 62의 합성62] Synthesis of Mat 62
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.6g을 얻었다; HRMS [M]+: 729.93The same procedure as in [Synthetic Example 9] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 4.6 g of the target compound; HRMS [M]+: 729.93
[[ 합성예Synthetic example 63] Mat 63의 합성63] Synthesis of Mat 63
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다; HRMS [M]+: 778.96The same procedure as in [Synthetic Example 10] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 4.7 g of the target compound; HRMS [M]+: 778.96
[[ 합성예Synthetic example 64] Mat 64의 합성64] Synthesis of Mat 64
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘 을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다; HRMS [M]+: 703.85The same procedure as in [Synthetic Example 11] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 5.1 g of the target compound; HRMS [M]+: 703.85
[[ 합성예Synthetic example 65] Mat 65의 합성65] Synthesis of Mat 65
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다; HRMS [M]+: 702.86The same procedure as in [Synthetic Example 12] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 4.2 g of the target compound; HRMS [M]+: 702.86
[[ 합성예Synthetic example 66] Mat 66의 합성66] Synthesis of Mat 66
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 13]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다; HRMS [M]+: 778.96The same procedure as in [Synthetic Example 13] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 4.7 g of the target compound; HRMS [M]+: 778.96
[[ 합성예Synthetic example 67] Mat 67의 합성67] Synthesis of Mat 67
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 14]과 동일한 과정을 수행하여 목적 화합물 3.8g을 얻었다; HRMS [M]+: 719.84The same procedure as in [Synthetic Example 14] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 3.8 g of the target compound; HRMS [M]+: 719.84
[[ 합성예Synthetic example 68] Mat 68의 합성68] Synthesis of Mat 68
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 15]과 동일한 과정을 수행하여 목적 화합물 4.5 g을 얻었다; HRMS [M]+: 718.86The same procedure as in [Synthetic Example 15] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 4.5 g of the target compound; HRMS [M]+: 718.86
[[ 합성예Synthetic example 69] Mat 69의 합성69] Synthesis of Mat 69
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 16]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다; HRMS [M]+: 715.86The same procedure as in [Synthetic Example 16] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 5.5 g of the target compound; HRMS [M]+: 715.86
[[ 합성예Synthetic example 70] Mat 70의 합성70] Synthesis of Mat 70
반응물로 4-([1,1'-바이페닐]-4-일)-6-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 17]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다; HRMS [M]+: 664.81The same procedure as in [Synthetic Example 17] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used as a reactant, to obtain 4.9 g of the target compound; HRMS [M]+: 664.81
[[ 합성예Synthetic example 71] Mat 71의 합성71] Synthesis of Mat 71
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다; HRMS [M]+: 637.77The same procedure as in [Synthetic Example 1] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 6.4 g of the target compound; HRMS [M]+: 637.77
[[ 합성예Synthetic example 72] Mat 72의 합성72] Synthesis of Mat 72
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다; HRMS [M]+: 688.26The same procedure as in [Synthetic Example 2] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 5.9 g of the target compound; HRMS [M]+: 688.26
[[ 합성예Synthetic example 73] Mat 73의 합성73] Synthesis of Mat 73
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다; HRMS [M]+: 688.83The same procedure as in [Synthetic Example 3] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 5.2 g of the target compound; HRMS [M]+: 688.83
[[ 합성예Synthetic example 74] Mat 74의 합성74] Synthesis of Mat 74
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다; HRMS [M]+: 738.89The same procedure as in [Synthetic Example 4] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 6.8 g of the target compound; HRMS [M]+: 738.89
[[ 합성예Synthetic example 75] Mat 75의 합성75] Synthesis of Mat 75
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 7.6g을 얻었다; HRMS [M]+: 738.89The same procedure as in [Synthetic Example 5] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 7.6 g of the target compound; HRMS [M]+: 738.89
[[ 합성예Synthetic example 76] Mat 76의 합성76] Synthesis of Mat 76
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 7.9g을 얻었다; HRMS [M]+: 814.99The same procedure as in [Synthetic Example 6] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 7.9 g of the target compound; HRMS [M]+: 814.99
[[ 합성예Synthetic example 77] Mat 77의 합성77] Synthesis of Mat 77
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 8.3g을 얻었다; HRMS [M]+: 788.95The same procedure as in [Synthetic Example 7] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 8.3 g of the target compound; HRMS [M]+: 788.95
[[ 합성예Synthetic example 78] Mat 78의 합성78] Synthesis of Mat 78
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 4.3g을 얻었다; HRMS [M]+: 762.92The same procedure as in [Synthetic Example 8] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 4.3 g of the target compound; HRMS [M]+: 762.92
[[ 합성예Synthetic example 79] Mat 79의 합성79] Synthesis of Mat 79
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 3.6g을 얻었다; HRMS [M]+: 754.94The same procedure as in [Synthetic Example 9] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 3.6 g of the target compound; HRMS [M]+: 754.94
[[ 합성예Synthetic example 80] Mat 80의 합성80] Synthesis of Mat 80
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다; HRMS [M]+: 803.97The same procedure as in [Synthetic Example 10] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 4.1 g of the target compound; HRMS [M]+: 803.97
[[ 합성예Synthetic example 81] Mat 81의 합성81] Synthesis of Mat 81
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 3.5g을 얻었다; HRMS [M]+: 728.26The same procedure as in [Synthetic Example 11] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 3.5 g of the target compound; HRMS [M]+: 728.26
[[ 합성예Synthetic example 82] Mat 82의 합성82] Synthesis of Mat 82
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 2.9g을 얻었다; HRMS [M]+: 727.87The same procedure as in [Synthetic Example 12] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 2.9 g of the target compound; HRMS [M]+: 727.87
[[ 합성예Synthetic example 83] Mat 83의 합성83] Synthesis of Mat 83
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 13]과 동일한 과정을 수행하여 목적 화합물 3.1g을 얻었다; HRMS [M]+: 803.97The same procedure as in [Synthetic Example 13] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 3.1 g of the target compound; HRMS [M]+: 803.97
[[ 합성예Synthetic example 84] Mat 84의 합성84] Synthesis of Mat 84
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 14]과 동일한 과정을 수행하여 목적 화합물 3.3g을 얻었다; HRMS [M]+: 744.85The same procedure as in [Synthetic Example 14] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 3.3 g of the target compound; HRMS [M]+: 744.85
[[ 합성예Synthetic example 85] Mat 85의 합성85] Synthesis of Mat 85
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 15]과 동일한 과정을 수행하여 목적 화합물 2.4g을 얻었다; HRMS [M]+: 743.87The same procedure as in [Synthetic Example 15] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 2.4 g of the target compound; HRMS [M]+: 743.87
[[ 합성예Synthetic example 86] Mat 86의 합성86] Synthesis of Mat 86
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 17]과 동일한 과정을 수행하여 목적 화합물 4.6g을 얻었다; HRMS [M]+: 689.82The same procedure as in [Synthetic Example 17] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 4.6 g of the target compound; HRMS [M]+: 689.82
[[ 합성예Synthetic example 87] Mat 87의 합성87] Synthesis of Mat 87
반응물로 2-(3-(6-([1,1'-바이페닐]-4-일)-2-페닐피리미딘-4-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 18]과 동일한 과정을 수행하여 목적 화합물 3.9g을 얻었다; HRMS [M]+: 715.86The same procedure as in [Synthetic Example 18] was followed, except that 2-(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 3.9 g of the target compound; HRMS [M]+: 715.86
[[ 합성예Synthetic example 88] Mat 88의 합성88] Synthesis of Mat 88
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-3-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다; HRMS [M]+: 538.65The same procedure as in [Synthetic Example 1] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-3-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 4.1 g of the target compound; HRMS [M]+: 538.65
[[ 합성예Synthetic example 89] Mat 89의 합성89] Synthesis of Mat 89
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-3-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 3.8g을 얻었다; HRMS [M]+: 638.78The same procedure as in [Synthetic Example 4] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-3-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 3.8 g of the target compound; HRMS [M]+: 638.78
[[ 합성예Synthetic example 90] Mat 90의 합성90] Synthesis of Mat 90
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-3-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 2.9g을 얻었다; HRMS [M]+: 638.77The same procedure as in [Synthetic Example 5] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-3-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 2.9 g of the target compound; HRMS [M]+: 638.77
[[ 합성예Synthetic example 91] Mat 91의 합성91] Synthesis of Mat 91
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-3-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.0g을 얻었다; HRMS [M]+: 688.83The same procedure as in [Synthetic Example 7] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-3-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 4.0 g of the target compound; HRMS [M]+: 688.83
[[ 합성예Synthetic example 92] Mat 92의 합성92] Synthesis of Mat 92
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-3-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 3.1g을 얻었다; HRMS [M]+: 654.82The same procedure as in [Synthetic Example 9] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-3-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 3.1 g of the target compound; HRMS [M]+: 654.82
[[ 합성예Synthetic example 93] Mat 93의 합성93] Synthesis of Mat 93
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-3-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다; HRMS [M]+: 703.85The same procedure as in [Synthetic Example 10] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-3-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 4.4 g of the target compound; HRMS [M]+: 703.85
[[ 합성예Synthetic example 94] Mat 94의 합성94] Synthesis of Mat 94
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-3-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 2.5g을 얻었다; HRMS [M]+: 627.75The same procedure as in [Synthetic Example 12] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-3-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 2.5 g of the target compound; HRMS [M]+: 627.75
[[ 합성예Synthetic example 95] Mat 95의 합성95] Synthesis of Mat 95
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-3-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 15]과 동일한 과정을 수행하여 목적 화합물 2.1g을 얻었다; HRMS [M]+: 643.75The same procedure as in [Synthetic Example 15] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-3-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 2.1 g of the target compound; HRMS [M]+: 643.75
[[ 합성예Synthetic example 96] Mat 96의 합성96] Synthesis of Mat 96
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-3-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 16]과 동일한 과정을 수행하여 목적 화합물 2.6g을 얻었다; HRMS [M]+: 640.75The same procedure as in [Synthetic Example 16] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-3-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 2.6 g of the target compound; HRMS [M]+: 640.75
[[ 합성예Synthetic example 97] Mat 97의 합성97] Synthesis of Mat 97
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-3-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 17]과 동일한 과정을 수행하여 목적 화합물 2.9g을 얻었다; HRMS [M]+: 589.70The same procedure as in [Synthetic Example 17] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-3-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 2.9 g of the target compound; HRMS [M]+: 589.70
[[ 합성예Synthetic example 98] Mat 98의 합성98] Synthesis of Mat 98
반응물로 4-([1,1'-바이페닐]-4-일)-6-(3-브로모-5-(피리딘-3-일)페닐)-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 18]과 동일한 과정을 수행하여 목적 화합물 3.8g을 얻었다; HRMS [M]+: 614.72The same procedure as in [Synthetic Example 18] was followed, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-(pyridin-3-yl)phenyl)-2-phenylpyrimidine was used as a reactant, to obtain 3.8 g of the target compound; HRMS [M]+: 614.72
[[ 합성예Synthetic example 99] Mat 99의 합성99] Synthesis of Mat 99
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-4-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 22]과 동일한 과정을 수행하여 목적 화합물 3.6g을 얻었다; HRMS [M]+: 638.77The same procedure as in [Synthetic Example 22] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-4-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 3.6 g of the target compound; HRMS [M]+: 638.77
[[ 합성예Synthetic example 100] Mat 100의 합성100] Synthesis of Mat 100
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-4-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 3.0g을 얻었다; HRMS [M]+: 638.77The same procedure as in [Synthetic Example 23] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-4-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 3.0 g of the target compound; HRMS [M]+: 638.77
[[ 합성예Synthetic example 101] Mat 101의 합성101] Synthesis of Mat 101
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-4-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 25]과 동일한 과정을 수행하여 목적 화합물 3.2g을 얻었다; HRMS [M]+: 688.83The same procedure as in [Synthetic Example 25] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-4-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 3.2 g of the target compound; HRMS [M]+: 688.83
[[ 합성예Synthetic example 102] Mat 102의 합성102] Synthesis of Mat 102
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-4-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 27]과 동일한 과정을 수행하여 목적 화합물 2.9g을 얻었다; HRMS [M]+: 654.82The same procedure as in [Synthetic Example 27] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-4-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 2.9 g of the target compound; HRMS [M]+: 654.82
[[ 합성예Synthetic example 103] Mat 103의 합성103] Synthesis of Mat 103
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-4-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 30]과 동일한 과정을 수행하여 목적 화합물 2.1g을 얻었다; HRMS [M]+: 627.75The same procedure as in [Synthetic Example 30] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-4-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 2.1 g of the target compound; HRMS [M]+: 627.75
[[ 합성예Synthetic example 104] Mat 104의 합성104] Synthesis of Mat 104
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-4-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 34]과 동일한 과정을 수행하여 목적 화합물 2.8g을 얻었다; HRMS [M]+: 640.75The same procedure as in [Synthetic Example 34] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-4-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 2.8 g of the target compound; HRMS [M]+: 640.75
[[ 합성예Synthetic example 105] Mat 105의 합성105] Synthesis of Mat 105
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-4-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 35]과 동일한 과정을 수행하여 목적 화합물 2.3g을 얻었다; HRMS [M]+: 589.70The same procedure as in [Synthetic Example 35] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-4-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 2.3 g of the target compound; HRMS [M]+: 589.70
[[ 합성예Synthetic example 106] Mat 106의 합성106] Synthesis of Mat 106
반응물로 2-([1,1'-바이페닐]-4-일)-4-(3-브로모-5-(피리딘-4-일)페닐)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 36]과 동일한 과정을 수행하여 목적 화합물 2.8g을 얻었다; HRMS [M]+: 615.74The same procedure as in [Synthetic Example 36] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromo-5-(pyridin-4-yl)phenyl)-6-phenyl-1,3,5-triazine was used as a reactant, to obtain 2.8 g of the target compound; HRMS [M]+: 615.74
[[ 합성예Synthetic example 107] Mat 107의 합성107] Synthesis of Mat 107
반응물로 8-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 2.0g을 얻었다; HRMS [M]+: 588.71The same procedure as in [Synthetic Example 1] was followed, except that 8-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 2.0 g of the target compound; HRMS [M]+: 588.71
[[ 합성예Synthetic example 108] Mat 108의 합성108] Synthesis of Mat 108
반응물로 8-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 2.9g을 얻었다; HRMS [M]+: 638.77The same procedure as in [Synthetic Example 3] was followed, except that 8-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 2.9 g of the target compound; HRMS [M]+: 638.77
[[ 합성예Synthetic example 109] Mat 109의 합성109] Synthesis of Mat 109
반응물로 8-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 3.3g을 얻었다; HRMS [M]+: 688.83The same procedure as in [Synthetic Example 4] was followed, except that 8-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 3.3 g of the target compound; HRMS [M]+: 688.83
[[ 합성예Synthetic example 110] Mat 110의 합성110] Synthesis of Mat 110
반응물로 8-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 3.7g을 얻었다; HRMS [M]+: 738.89The same procedure as in [Synthetic Example 7] was followed, except that 8-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 3.7 g of the target compound; HRMS [M]+: 738.89
[[ 합성예Synthetic example 111] Mat 111의 합성111] Synthesis of Mat 111
반응물로 8-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 2.6g을 얻었다; HRMS [M]+: 704.88The same procedure as in [Synthetic Example 9] was followed, except that 8-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 2.6 g of the target compound; HRMS [M]+: 704.88
[[ 합성예Synthetic example 112] Mat 112의 합성112] Synthesis of Mat 112
반응물로 8-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 2.0g을 얻었다; HRMS [M]+: 677.81The same procedure as in [Synthetic Example 12] was followed, except that 8-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 2.0 g of the target compound; HRMS [M]+: 677.81
[[ 합성예Synthetic example 113] Mat 113의 합성113] Synthesis of Mat 113
반응물로 8-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 3.4g을 얻었다; HRMS [M]+: 677.81The same procedure as in [Synthetic Example 12] was followed, except that 8-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)quinoline was used as a reactant, to obtain 3.4 g of the target compound; HRMS [M]+: 677.81
[[ 합성예Synthetic example 114] Mat 114의 합성114] Synthesis of Mat 114
반응물로 8-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)퀴놀린을 사용한 것을 제외하고는 [합성예 53]동일한 과정을 수행하여 목적 화합물 2.9g을 얻었다; HRMS [M]+: 665.80The same procedure as in [Synthetic Example 53] was followed, except that 8-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)quinoline was used as the reactant, to obtain 2.9 g of the target compound; HRMS [M]+: 665.80
[[ 합성예Synthetic example 115] Mat 115의 합성115] Synthesis of Mat 115
반응물로 2-([1,1'-바이페닐]-4-일)-4-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 54]과 동일한 과정을 수행하여 목적 화합물 2.8g을 얻었다; HRMS [M]+: 614.75The same procedure as in [Synthetic Example 54] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine was used as the reactant, to obtain 2.8 g of the target compound; HRMS [M]+: 614.75
[[ 합성예Synthetic example 116] Mat 116의 합성116] Synthesis of Mat 116
반응물로 2-([1,1'-바이페닐]-4-일)-4-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 55]과 동일한 과정을 수행하여 목적 화합물 2.5g을 얻었다; HRMS [M]+: 664.81The same procedure as in [Synthetic Example 55] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine was used as the reactant, to obtain 2.5 g of the target compound; HRMS [M]+: 664.81
[[ 합성예Synthetic example 117] Mat 117의 합성117] Synthesis of Mat 117
반응물로 2-([1,1'-바이페닐]-4-일)-4-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 57]과 동일한 과정을 수행하여 목적 화합물 3.3g을 얻었다; HRMS [M]+: 714.87The same procedure as in [Synthetic Example 57] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine was used as the reactant, to obtain 3.3 g of the target compound; HRMS [M]+: 714.87
[[ 합성예Synthetic example 118] Mat 118의 합성118] Synthesis of Mat 118
반응물로 2-([1,1'-바이페닐]-4-일)-4-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 58]과 동일한 과정을 수행하여 목적 화합물 3.0g을 얻었다; HRMS [M]+: 714.87The same procedure as in [Synthetic Example 58] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine was used as the reactant, to obtain 3.0 g of the target compound; HRMS [M]+: 714.87
[[ 합성예Synthetic example 119] Mat 119의 합성119] Synthesis of Mat 119
반응물로 2-([1,1'-바이페닐]-4-일)-4-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 60]과 동일한 과정을 수행하여 목적 화합물 3.8g을 얻었다; HRMS [M]+: 764.93The same procedure as in [Synthetic Example 60] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine was used as the reactant, to obtain 3.8 g of the target compound; HRMS [M]+: 764.93
[[ 합성예Synthetic example 120] Mat 120의 합성120] Synthesis of Mat 120
반응물로 2-([1,1'-바이페닐]-4-일)-4-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 62]과 동일한 과정을 수행하여 목적 화합물 2.7g을 얻었다; HRMS [M]+: 730.92The same procedure as in [Synthetic Example 62] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine was used as the reactant, to obtain 2.7 g of the target compound; HRMS [M]+: 730.92
[[ 합성예Synthetic example 121] Mat 121의 합성121] Synthesis of Mat 121
반응물로 2-([1,1'-바이페닐]-4-일)-4-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 65]과 동일한 과정을 수행하여 목적 화합물 2.0g을 얻었다; HRMS [M]+: 703.85The same procedure as in [Synthetic Example 65] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine was used as the reactant, to obtain 2.0 g of the target compound; HRMS [M]+: 703.85
[[ 합성예Synthetic example 122] Mat 122의 합성122] Synthesis of Mat 122
반응물로 2-([1,1'-바이페닐]-4-일)-4-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 69]과 동일한 과정을 수행하여 목적 화합물 3.1g을 얻었다; HRMS [M]+: 716.85The same procedure as in [Synthetic Example 69] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine was used as the reactant, to obtain 3.1 g of the target compound; HRMS [M]+: 716.85
[[ 합성예Synthetic example 123] Mat 123의 합성123] Synthesis of Mat 123
반응물로 2-([1,1'-바이페닐]-4-일)-4-(5-브로모-4'-(피리딘-3-일)-[1,1'-바이페닐]-3-일)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 70]과 동일한 과정을 수행하여 목적 화합물 3.8g을 얻었다; HRMS [M]+: 664.81The same procedure as in [Synthetic Example 70] was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-(5-bromo-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine was used as the reactant, to obtain 3.8 g of the target compound; HRMS [M]+: 664.81
[[ 합성예Synthetic example 124] Mat 124의 합성124] Synthesis of Mat 124
반응물로 2-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 71]과 동일한 과정을 수행하여 목적 화합물 3.0g을 얻었다; HRMS [M]+: 639.76The same procedure as in [Synthetic Example 71] was followed, except that 2-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 3.0 g of the target compound; HRMS [M]+: 639.76
[[ 합성예Synthetic example 125] Mat 125의 합성125] Synthesis of Mat 125
반응물로 2-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 72]과 동일한 과정을 수행하여 목적 화합물 3.4g을 얻었다; HRMS [M]+: 689.82The same procedure as in [Synthetic Example 72] was followed, except that 2-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 3.4 g of the target compound; HRMS [M]+: 689.82
[[ 합성예Synthetic example 126] Mat 126의 합성126] Synthesis of Mat 126
반응물로 2-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 74]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다; HRMS [M]+: 739.88The same procedure as in [Synthetic Example 74] was followed, except that 2-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 4.1 g of the target compound; HRMS [M]+: 739.88
[[ 합성예Synthetic example 127] Mat 127의 합성127] Synthesis of Mat 127
반응물로 2-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 77]과 동일한 과정을 수행하여 목적 화합물 4.6g을 얻었다; HRMS [M]+: 789.94The same procedure as in [Synthetic Example 77] was followed, except that 2-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 4.6 g of the target compound; HRMS [M]+: 789.94
[[ 합성예Synthetic example 128] Mat 128의 합성128] Synthesis of Mat 128
반응물로 2-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 79]과 동일한 과정을 수행하여 목적 화합물 3.8g을 얻었다; HRMS [M]+: 755.93The same procedure as in [Synthetic Example 79] was followed, except that 2-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 3.8 g of the target compound; HRMS [M]+: 755.93
[[ 합성예Synthetic example 129] Mat 129의 합성129] Synthesis of Mat 129
반응물로 2-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 82]과 동일한 과정을 수행하여 목적 화합물 2.6g을 얻었다; HRMS [M]+: 728.86The same procedure as in [Synthetic Example 82] was followed, except that 2-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 2.6 g of the target compound; HRMS [M]+: 728.86
[[ 합성예Synthetic example 130] Mat 130의 합성130] Synthesis of Mat 130
반응물로 2-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 85]과 동일한 과정을 수행하여 목적 화합물 2.0g을 얻었다; HRMS [M]+: 744.86The same procedure as in [Synthetic Example 85] was followed, except that 2-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 2.0 g of the target compound; HRMS [M]+: 744.86
[[ 합성예Synthetic example 131] Mat 131의 합성131] Synthesis of Mat 131
반응물로 2-(3-(4-([1,1'-바이페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-5-브로모페닐)-1,10-페난트롤린을 사용한 것을 제외하고는 [합성예 87]과 동일한 과정을 수행하여 목적 화합물 4.0g을 얻었다; HRMS [M]+: 716.85The same procedure as in [Synthetic Example 87] was followed, except that 2-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-5-bromophenyl)-1,10-phenanthroline was used as a reactant, to obtain 4.0 g of the target compound; HRMS [M]+: 716.85
[[ 실시예Example 1] 청색 유기 1] Blue organic 전계Electric field 발광 소자의 제조Manufacturing of light-emitting devices
합성예에서 합성된 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 청색 유기 전계 발광 소자를 제조하였다.After the compound synthesized in the synthetic example was purified by high purity sublimation using a commonly known method, a blue organic electroluminescent device was manufactured as follows.
ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고, 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.A glass substrate coated with a 1500 Å thick ITO (Indium tin oxide) film was ultrasonically washed in distilled water. After the distilled water washing, the substrate was ultrasonically washed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (80 nm)/NPB (15 nm)/ADN + 5 % DS-405 (30nm)/합성예 1의 합성예의 화합물(30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다.On the ITO transparent electrode prepared as described above, an organic electroluminescent device was manufactured by stacking DS-205 (80 nm)/NPB (15 nm)/ADN + 5% DS-405 (30 nm)/compound of Synthesis Example 1 (30 nm)/LiF (1 nm)/Al (200 nm) in that order.
이때 사용된 NPB, ADN 및 Alq3의 구조는 다음과 같다.The structures of NPB, ADN and Alq 3 used at this time are as follows.
[[ 비교예Comparative example 1] 청색1] Blue 유기 Organic 전계Electric field 발광 소자의 제조Manufacturing of light-emitting devices
수명 개선층을 포함하지 않고, 전자 수송층 물질인 Alq3을 30nm로 증착하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다. A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the lifetime improvement layer was not included and Alq 3 , an electron transport layer material, was deposited at a thickness of 30 nm.
[[ 평가예Evaluation example 1]1]
실시예 1 내지 62 및 비교예 1에서 각각 제조된 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율, 발광파장을 측정하였고, 그 결과를 하기 표 1에 나타내었다.For the organic electroluminescent devices manufactured in Examples 1 to 62 and Comparative Example 1, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA/cm2 were measured, and the results are shown in Table 1 below.
(V)Driving voltage
(V)
(cd/A)Current efficiency
(cd/A)
(nm)Luminescence peak
(nm)
상기 표 1을 살펴보면, 본 발명의 화학식 1로 표시되는 화합물을 전자수송층에 사용하는 실시예 1~62의 유기 EL 소자는 종래 Alq3를 전자수송층에 사용하는 비교예 1의 유기 EL 소자보다 전류효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 확인할 수 있었다.Looking at Table 1 above, it was confirmed that the organic EL devices of Examples 1 to 62 using the compound represented by Chemical Formula 1 of the present invention in the electron transport layer exhibited superior performance in terms of current efficiency and driving voltage than the organic EL device of Comparative Example 1 using Alq 3 in the electron transport layer.
Claims (10)
[화학식 6]
[화학식 7]
[화학식 8]
상기 화학식 6 내지 8에서,
L1 및 L2는 서로 동일하거나 상이하며, 단일결합 또는 페닐기이며,
R12 및 R22는 서로 동일하거나 상이하며, 각각 독립적으로 C6~C60의 아릴기 또는 핵원자수 5 내지 60의 헤테로아릴기이나,
R12 및 R22 중 적어도 어느 하나는 하기 치환기로 이루어진 군으로부터 선택되고,
단, R12 및 R22 모두 퀴놀린기인 것은 제외하며,
R11 및 R21은 서로 동일하거나 상이하며, 각각 독립적으로 C6~C60의 아릴기 또는 핵원자수 5 내지 60의 헤테로아릴기이나, R11 및 R21 중 적어도 어느 하나는 하기 치환기로 이루어진 군으로부터 선택되고,
단, R11 및 R2 모두 퀴놀린기인 것은 제외하며,
L1 및 L2가 서로 동일한 경우, R11 및 R21은 서로 상이하며,
L1 및 L2가 서로 동일한 경우, R12 및 R22은 서로 상이하며,
Ar1 및 Ar2는 서로 상이하며, 각각 독립적으로 C6~C60의 아릴기 또는 핵원자수 5 내지 60의 헤테로아릴기이다.Compounds represented by the following chemical formulas 6 to 8:
[Chemical formula 6]
[Chemical formula 7]
[Chemical formula 8]
In the above chemical formulas 6 to 8,
L 1 and L 2 are the same or different and are a single bond or a phenyl group,
R 12 and R 22 are the same or different and each independently represents an aryl group having C 6 to C 60 or a heteroaryl group having 5 to 60 nuclear atoms.
At least one of R 12 and R 22 is selected from the group consisting of the following substituents,
However, excluding those in which both R 12 and R 22 are quinoline groups.
R 11 and R 21 are the same or different, and each independently represents an aryl group having C 6 to C 60 or a heteroaryl group having 5 to 60 nuclear atoms, but at least one of R 11 and R 21 is selected from the group consisting of the following substituents,
However, excluding those in which both R 11 and R 2 are quinoline groups.
If L 1 and L 2 are identical, R 11 and R 21 are different,
If L 1 and L 2 are identical, R 12 and R 22 are different,
Ar 1 and Ar 2 are different from each other and each independently represents an aryl group having C 6 to C 60 or a heteroaryl group having 5 to 60 nuclear atoms.
상기 Ar1 및 Ar2는 서로 상이하며, 각각 독립적으로 C6~C60의 아릴기인 화합물.In paragraph 1,
A compound wherein the above Ar 1 and Ar 2 are different from each other and are each independently an aryl group having C 6 to C 60 .
상기 Ar1 및 Ar2는 서로 상이하며, 각각 독립적으로 페닐 또는 바이페닐에서 선택되는 화합물.In paragraph 1,
A compound wherein the above Ar 1 and Ar 2 are different from each other and are each independently selected from phenyl or biphenyl.
상기 화합물은 아래의 화합물로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물:
In paragraph 1,
The compound is characterized in that the compound is selected from the group consisting of the following compounds:
상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항에 따른 화합물을 포함하는 것인 유기 전계 발광 소자.An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode,
An organic electroluminescent device, wherein at least one of the organic layers of one or more layers comprises a compound according to claim 1.
상기 유기물층은 발광층, 발광 보조층, 정공 수송층, 정공 주입층, 전자 수송층 및 전자 주입층으로 이루어진 군으로부터 선택되는 유기 전계 발광 소자.In Article 7,
An organic electroluminescent device, wherein the organic layer is selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer.
상기 유기물층은 발광층, 정공 수송층 및 전자 수송층으로 이루어진 군으로부터 선택되는 유기 전계 발광 소자.In Article 7,
An organic electroluminescent device, wherein the organic layer is selected from the group consisting of a light-emitting layer, a hole transport layer, and an electron transport layer.
상기 유기물층은 전자수송층인 것을 특징으로 하는 유기 전계 발광 소자.In Article 7,
An organic electroluminescent device, characterized in that the organic layer is an electron transport layer.
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