KR20190020514A - Compound for organic electroluminescent device and organic electroluminescent device comprising the same - Google Patents
Compound for organic electroluminescent device and organic electroluminescent device comprising the same Download PDFInfo
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- KR20190020514A KR20190020514A KR1020170105568A KR20170105568A KR20190020514A KR 20190020514 A KR20190020514 A KR 20190020514A KR 1020170105568 A KR1020170105568 A KR 1020170105568A KR 20170105568 A KR20170105568 A KR 20170105568A KR 20190020514 A KR20190020514 A KR 20190020514A
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- South Korea
- Prior art keywords
- substituted
- unsubstituted
- group
- compound
- organic electroluminescent
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 70
- 238000005401 electroluminescence Methods 0.000 claims abstract description 9
- 239000010410 layer Substances 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
- 239000012044 organic layer Substances 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 229910052717 sulfur Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims description 9
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 230000000903 blocking effect Effects 0.000 claims description 6
- 239000002019 doping agent Substances 0.000 claims description 4
- 125000004431 deuterium atom Chemical group 0.000 claims 4
- 239000000463 material Substances 0.000 abstract description 25
- 230000005525 hole transport Effects 0.000 abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- 239000000243 solution Substances 0.000 description 37
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- -1 aryl substituted alkyl radical Chemical class 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- 239000012046 mixed solvent Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 239000010409 thin film Substances 0.000 description 11
- 125000000524 functional group Chemical group 0.000 description 10
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 150000001975 deuterium Chemical group 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000000335 thiazolyl group Chemical group 0.000 description 4
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 3
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 3
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- BEBLXYZXQGRFKD-UHFFFAOYSA-N [4-(4-phenyl-n-(4-phenylphenyl)anilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=C(C=2C=CC=CC=2)C=C1 BEBLXYZXQGRFKD-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940126142 compound 16 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940125810 compound 20 Drugs 0.000 description 3
- 229940126208 compound 22 Drugs 0.000 description 3
- 229940125877 compound 31 Drugs 0.000 description 3
- 229940125936 compound 42 Drugs 0.000 description 3
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- VQSRKMNBWMHJKY-YTEVENLXSA-N n-[3-[(4ar,7as)-2-amino-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)NC1=CC=C(F)C([C@@]23[C@@H](CN(C2)C=2N=CC(F)=CN=2)CSC(N)=N3)=C1 VQSRKMNBWMHJKY-YTEVENLXSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000004419 alkynylene group Chemical group 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
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 230000014509 gene expression Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- BCASZEAAHJEDAL-PHEQNACWSA-N 1,4-bis[(e)-2-(4-methylphenyl)ethenyl]benzene Chemical compound C1=CC(C)=CC=C1\C=C\C(C=C1)=CC=C1\C=C\C1=CC=C(C)C=C1 BCASZEAAHJEDAL-PHEQNACWSA-N 0.000 description 1
- MOFZWXIXTVLLAC-UHFFFAOYSA-N 1-bromo-4-phenyldibenzofuran Chemical compound BrC1=CC=C(C2=C1C1=C(O2)C=CC=C1)C1=CC=CC=C1 MOFZWXIXTVLLAC-UHFFFAOYSA-N 0.000 description 1
- WUYYVOWEBMOELQ-UHFFFAOYSA-N 1-bromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2Br WUYYVOWEBMOELQ-UHFFFAOYSA-N 0.000 description 1
- HJQPXHGOYBUDPE-UHFFFAOYSA-N 1-bromodibenzofuran-4-amine Chemical compound C12=CC=CC=C2OC2=C1C(Br)=CC=C2N HJQPXHGOYBUDPE-UHFFFAOYSA-N 0.000 description 1
- NVKKHESARUWWRX-UHFFFAOYSA-N 1-bromodibenzothiophen-4-amine Chemical compound BrC1=CC=C(C=2SC3=C(C21)C=CC=C3)N NVKKHESARUWWRX-UHFFFAOYSA-N 0.000 description 1
- JESBGFNZNSEZMR-UHFFFAOYSA-N 1-bromodibenzothiophene Chemical compound S1C2=CC=CC=C2C2=C1C=CC=C2Br JESBGFNZNSEZMR-UHFFFAOYSA-N 0.000 description 1
- BIEFDNUEROKZRA-UHFFFAOYSA-N 2-(2-phenylethenyl)aniline Chemical class NC1=CC=CC=C1C=CC1=CC=CC=C1 BIEFDNUEROKZRA-UHFFFAOYSA-N 0.000 description 1
- POXIZPBFFUKMEQ-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical group [N-]=C=[C+]C#N POXIZPBFFUKMEQ-UHFFFAOYSA-N 0.000 description 1
- KYGSXEYUWRFVNY-UHFFFAOYSA-N 2-pyran-2-ylidenepropanedinitrile Chemical compound N#CC(C#N)=C1OC=CC=C1 KYGSXEYUWRFVNY-UHFFFAOYSA-N 0.000 description 1
- XKEFGMGLUNIEPW-UHFFFAOYSA-N 3-(1-bromodibenzofuran-4-yl)-9-phenylcarbazole Chemical compound BrC1=C2C(OC3=C2C=CC=C3)=C(C=C1)C1=CC=C2N(C3=C(C=CC=C3)C2=C1)C1=CC=CC=C1 XKEFGMGLUNIEPW-UHFFFAOYSA-N 0.000 description 1
- PJUAIXDOXUXBDR-UHFFFAOYSA-N 3-iodo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(I)=CC=C2N1C1=CC=CC=C1 PJUAIXDOXUXBDR-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- DSNQPNGWFBNTQE-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3,5,6-tetraphenylaniline Chemical group C1=CC(N)=CC=C1C(C(=C(C=1C=CC=CC=1)C(N)=C1C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C1=CC=CC=C1 DSNQPNGWFBNTQE-UHFFFAOYSA-N 0.000 description 1
- DYTYBRPMNQQFFL-UHFFFAOYSA-N 4-bromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(Br)=CC=C2 DYTYBRPMNQQFFL-UHFFFAOYSA-N 0.000 description 1
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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Abstract
Description
본 발명은 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자에 관한 것으로, 보다 상세하게는 발광 효율 및 수명이 우수한 아민계 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자에 관한 것이다.BACKGROUND OF THE
유기전계발광소자는 기존 액정 표시 장치(LCD), 플라즈마 디스플레이 패널(PDP) 그리고 전계 방출 디스플레이 (FED)등의 타 평판 표시 소자에 비해 구조가 간단하고, 제조 공정상 다양한 장점이 있으며 높은 휘도 및 시야각 특성이 우수하며, 응답속도가 빠르고 구동전압이 낮아 벽걸이 TV등의 평판 디스플레이 또는 디스플레이의 배면광, 조명, 광고판 등의 광원으로서 사용되도록 활발하게 개발이 진행되고 있다.The organic electroluminescent device has a simpler structure than other flat panel display devices such as a liquid crystal display (LCD), a plasma display panel (PDP) and a field emission display (FED) And has a high response speed and a low driving voltage, so that it is being actively developed to be used as a light source for a flat panel display such as a wall-mounted TV or a backlight of a display, a lighting, and a billboard.
유기전계발광소자는 일반적으로 직류 전압을 인가하였을 때 양극으로부터 주입된 정공과 음극으로부터 주입된 전자가 재결합하여 전자-정공 쌍인 엑시톤을 형성하며 이 엑시톤이 안정한 바닥 상태로 돌아오면서 그에 해당하는 에너지를 발광 재료에 전달함에 의해 빛으로 변환된다. In general, when a direct current voltage is applied to an organic electroluminescent device, holes injected from the anode recombine with electrons injected from the cathode to form an electron-hole pair exciton, and the exciton returns to a stable ground state, It is converted into light by transmission to the material.
유기전계발광소자의 효율과 안정성을 높이기 위해 이스트만 코닥사의 탕(C. W. Tang) 등에 의해 두 개의 반대 전극 사이에 적층형 유기물 박막을 구성하여 저전압 구동 유기전계발광소자가 보고(C. W. Tang, S. A. Vanslyke, Applied Physics Letters, 51권 913페이지, 1987년)된 이래, 다층 박막 구조형 유기전계발광소자용 유기 재료에 대한 연구가 활발히 진행되고 있다. 이러한 적층형 유기전계발광소자의 효율과 수명은 박막을 구성하는 재료의 분자구조와 관련이 깊다. 예컨대, 박막을 구성하는 재료 중 발광재료, 정공수송층 물질, 또는 전자수송층 물질 등의 구조에 따라 양자효율이 크게 영향을 받으며, 열안정성이 떨어질 경우 고온 또는 구동온도에서 재료의 결정화가 이루어져 소자의 수명을 단축시키는 원인이 되고 있다.In order to improve the efficiency and stability of the organic electroluminescent device, a laminated organic thin film is formed between two opposing electrodes by CW Tang et al. Of Eastman Kodak Company, and a low voltage driven organic electroluminescent device is reported (CW Tang, SA Vanslyke, Applied Physics Letters, vol. 51, p. 913, 1987), studies on organic materials for multilayer thin film structure organic electroluminescent devices have been actively conducted. The efficiency and lifetime of such a stacked organic electroluminescent device are closely related to the molecular structure of the material constituting the thin film. For example, the quantum efficiency is greatly influenced by the structures of the light emitting material, the hole transporting layer material, and the electron transporting layer material among the materials constituting the thin film, and when the thermal stability is deteriorated, the crystallization of the material occurs at a high temperature or a driving temperature, Is shortened.
지금까지 알려져 있는 유기전계발광소자의 정공 수송 물질은 진공 증착에 의해 형성된 박막이 열 및 전기적으로 충분히 안정하지 않기 때문에, 소자 구동시의 발열에 의해 상기 박막의 결정화가 촉진되고 막질이 변화되어 궁극적으로 소자의 발광 효율의 저하된다. 또한, 다크 스팟이라고 하는 비발광부가 발생 및 증가하고, 정전류 구동시의 전압의 상승 등을 초래하여, 결국은 소자의 파괴에 이를 수 있는 문제점이 있다.The hole transporting material of the organic electroluminescence device which has been hitherto known is not sufficiently stable in terms of heat and electric charge because the thin film formed by the vacuum deposition is not sufficiently stable. Therefore, the crystallization of the thin film is promoted by the heat generated when the device is driven, The luminous efficiency of the device is lowered. Furthermore, there is a problem that a non-light emitting portion called a dark spot is generated and increased, and a voltage is increased at the time of constant current driving, and eventually the device is broken.
또한 낮은 삼중항 에너지로 인해 인광성 발광 재료를 사용한 유기전계발광소자는 발광층의 발광 재료에서 생성된 삼중항 엑시톤을 구속하지 못하는 단점이 있어, 결국 소자의 발광 효율이 저하되는 문제가 있다.Further, the organic electroluminescent device using the phosphorescent light emitting material due to low triplet energy has a disadvantage in that it can not confine the triplet excitons generated in the light emitting material of the light emitting layer, resulting in a problem that the luminous efficiency of the device is deteriorated.
본 발명의 목적은 상기 문제점을 해결하기 위한 것으로, 열 안정성이 높으며, 발광 효율 및 수명이 개선된 정공 수송성을 갖는 유기전계발광소자용 화합물을 제공하는 데 있다. SUMMARY OF THE INVENTION An object of the present invention is to provide a compound for an organic electroluminescent device having a high thermal stability and a hole transporting property with improved luminescence efficiency and service life.
또한, 본 발명의 유기전계발광소자용 화합물을 발광층과 접촉하는 정공 수송층 물질로 적용하였을 경우, 삼중항 에너지를 높여 유기전계발광소자의 효율을 향상시킬 수 있으며 수명을 개선할 수 있다.In addition, when the compound for an organic electroluminescence device of the present invention is applied to a hole transporting layer material in contact with a light emitting layer, the efficiency of the organic light emitting device can be improved by raising triplet energy, and the lifetime can be improved.
그러나, 본원이 해결하고자 하는 과제는 이상에서 언급한 과제로 제한되지 않으며, 언급되지 않은 또 다른 과제들은 아래의 기재로부터 당업자에게 명확하게 이해될 수 있을 것이다.However, the problems to be solved by the present invention are not limited to the above-mentioned problems, and other problems not mentioned can be clearly understood by those skilled in the art from the following description.
본 발명의 하나의 측면에 따르면, 하기 구조식 1로 표시되는 유기전계발광소자용 화합물이 제공될 수 있다.According to one aspect of the present invention, a compound for an organic electroluminescence device represented by the following
[구조식 1][Structural formula 1]
구조식 1에서,In
R1 내지 R6은 서로 같거나 다르고, R1 내지 R6은 각각 독립적으로 수소원자, 중수소원자, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이고,R 1 to R 6 are the same as or different from each other and each of R 1 to R 6 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
L은 원자가결합, 치환 또는 비치환된 C1 내지 C30 알킬렌기, 치환 또는 비치환된 C3 내지 C30 시클로알킬렌기, 치환 또는 비치환된 C2 내지 C30 헤테로시클로알킬렌기, 치환 또는 비치환된 C6 내지 C30 아릴렌기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로아릴렌기이고,L is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C2 to C30 heterocycloalkylene group, a substituted or unsubstituted C6 to C30 aryl Or a substituted or unsubstituted C2 to C30 heteroarylene group,
X는 산소원자 또는 황원자이고,X is an oxygen atom or a sulfur atom,
Ar1 내지 Ar3은 서로 같거나 다르고, Ar1 내지 Ar3은 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기일 수 있다.Ar 1 to Ar 3 are the same or different from each other and Ar 1 to Ar 3 each independently represent a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group.
바람직하게는, 상기 구조식 1로 표시되는 화합물은 하기 구조식 2로 표시되는 화합물일 수 있다. Preferably, the compound represented by the structural formula (1) may be a compound represented by the following structural formula (2).
[구조식 2][Structural formula 2]
구조식 2에서,In formula 2,
R1 내지 R6은 서로 같거나 다르고, R1 내지 R6은 각각 독립적으로 수소원자, 중수소원자, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이고,R 1 to R 6 are the same as or different from each other and each of R 1 to R 6 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
L은 원자가결합, 치환 또는 비치환된 C1 내지 C30 알킬렌기, 치환 또는 비치환된 C3 내지 C30 시클로알킬렌기, 치환 또는 비치환된 C2 내지 C30 헤테로시클로알킬렌기, 치환 또는 비치환된 C6 내지 C30 아릴렌기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로아릴렌기이고,L is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C2 to C30 heterocycloalkylene group, a substituted or unsubstituted C6 to C30 aryl Or a substituted or unsubstituted C2 to C30 heteroarylene group,
X는 산소원자 또는 황원자이고,X is an oxygen atom or a sulfur atom,
Ar1 내지 Ar3은 서로 같거나 다르고, Ar1 내지 Ar3은 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기일 수 있다.Ar 1 to Ar 3 are the same or different from each other and Ar 1 to Ar 3 each independently represent a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group.
바람직하게는, 상기 구조식 1로 표시되는 화합물은 하기 구조식 3으로 표시되는 화합물일 수 있다. Preferably, the compound represented by Formula 1 may be a compound represented by Formula 3 below.
[구조식 3][Structural Formula 3]
구조식 3에서,In Structure 3,
R1 내지 R6은 서로 같거나 다르고, R1 내지 R6은 각각 독립적으로 수소원자, 중수소원자, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이고,R 1 to R 6 are the same as or different from each other and each of R 1 to R 6 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
L은 원자가결합, 치환 또는 비치환된 C1 내지 C30 알킬렌기, 치환 또는 비치환된 C3 내지 C30 시클로알킬렌기, 치환 또는 비치환된 C2 내지 C30 헤테로시클로알킬렌기, 치환 또는 비치환된 C6 내지 C30 아릴렌기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로아릴렌기이고,L is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C2 to C30 heterocycloalkylene group, a substituted or unsubstituted C6 to C30 aryl Or a substituted or unsubstituted C2 to C30 heteroarylene group,
X는 산소원자 또는 황원자이고,X is an oxygen atom or a sulfur atom,
Ar1 내지 Ar3은 서로 같거나 다르고, Ar1 내지 Ar3은 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기일 수 있다. Ar 1 to Ar 3 are the same or different from each other and Ar 1 to Ar 3 each independently represent a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group.
또한 바람직하게는, Ar1 내지 Ar3은 서로 같거나 다르고, Ar1 내지 Ar3은 각각 독립적으로 
R7 내지 R38은 서로 같거나 다르고, R7 내지 R38은 각각 독립적으로 수소원자, 중수소원자, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기일 수 있다. R 7 to R 38 are the same or different from each other and each of R 7 to R 38 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
상기 유기전계발광소자용 화합물은 하기 화학식으로 표시되는 화합물 1 내지 70 중에서 선택된 어느 하나일 수 있으나, 여기에 한정되지 않는다.The organic electroluminescent device compound may be any one selected from
본 발명의 다른 측면에 따르면, 상기 유기전계발광소자용 화합물을 포함하는 유기전계발광소자가 제공될 수 있다.According to another aspect of the present invention, there is provided an organic electroluminescent device comprising the compound for an organic electroluminescent device.
본 발명의 또 다른 측면에 따르면, 제1전극, 제2전극 및 상기 제1전극과 제2전극 사이에 단수 또는 복수의 유기물층을 포함하는 유기전계발광소자에 있어서, 상기 단수 또는 복수의 유기물층 중에서 선택된 1종 이상의 유기물층은 상기 유기전계발광소자용 화합물을 포함하는 것을 특징으로 하는 유기전계발광소자가 제공될 수 있다.According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and a single or a plurality of organic layers between the first electrode and the second electrode, The organic electroluminescent device may further include at least one organic compound layer including the organic electroluminescent compound.
상기 단수 또는 복수의 유기물층은 발광층을 포함할 수 있다.The singular or plural organic layers may include a light emitting layer.
상기 복수의 유기물층은 발광층을 포함하고, 상기 복수의 유기물층은 전자주입층, 전자수송층, 정공차단층, 전자차단층, 정공수송층 및 정공주입층 중에서 선택된 1종 이상을 추가로 포함할 수 있다.The plurality of organic layers may include a light emitting layer, and the plurality of organic layers may further include at least one selected from an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, a hole transporting layer, and a hole injecting layer.
상기 발광층은 호스트와 도펀트를 포함할 수 있다.The light emitting layer may include a host and a dopant.
본 발명은 열 안정성이 높으며, 발광 효율 및 수명이 개선된 정공 수송성을 갖는 유기전계발광소자용 화합물을 제공할 수 있다. The present invention can provide a compound for an organic electroluminescent device having a high thermal stability and a hole transporting property with improved luminescent efficiency and service life.
또한, 본 발명의 유기전계발광소자용 화합물을 발광층과 접촉하는 정공 수송층 물질로 적용하였을 경우, 삼중항 에너지를 높여 유기전계발광소자의 효율을 향상시킬 수 있으며 수명을 개선할 수 있다.In addition, when the compound for an organic electroluminescence device of the present invention is applied to a hole transporting layer material in contact with a light emitting layer, the efficiency of the organic light emitting device can be improved by raising triplet energy, and the lifetime can be improved.
도 1은 본 발명의 일 실시예에 따른 유기전계발광소자의 단면을 나타낸 단면도이다.
도 2는 본 발명의 다른 일 실시예에 따른 유기전계발광소자의 단면을 나타낸 단면도이다.1 is a cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention.
2 is a cross-sectional view illustrating an organic electroluminescent device according to another embodiment of the present invention.
본 발명은 다양한 변환을 가할 수 있고 여러 가지 실시예를 가질 수 있는 바, 특정 실시예들을 예시하고 상세한 설명에 상세하게 설명하고자 한다. 그러나, 이는 본 발명을 특정한 실시 형태에 대해 한정하려는 것이 아니며, 본 발명의 사상 및 기술 범위에 포함되는 모든 변환, 균등물 내지 대체물을 포함하는 것으로 이해되어야 한다. 본 발명을 설명함에 있어서 관련된 공지 기술에 대한 구체적인 설명이 본 발명의 요지를 흐릴 수 있다고 판단되는 경우 그 상세한 설명을 생략한다.The invention is capable of various modifications and may have various embodiments, and particular embodiments are exemplified and will be described in detail in the detailed description. It is to be understood, however, that the invention is not to be limited to the specific embodiments, but includes all modifications, equivalents, and alternatives falling within the spirit and scope of the invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described in detail with reference to the accompanying drawings.
또한, 이하에서 사용될 제1, 제2 등과 같이 서수를 포함하는 용어는 다양한 구성요소들을 설명하는데 사용될 수 있지만, 상기 구성요소들은 상기 용어들에 의해 한정되지는 않는다. 상기 용어들은 하나의 구성요소를 다른 구성요소로부터 구별하는 목적으로만 사용된다. 예를 들어, 본 발명의 권리 범위를 벗어나지 않으면서 제1 구성요소는 제2 구성요소로 명명될 수 있고, 유사하게 제2 구성요소도 제1 구성요소로 명명될 수 있다. Furthermore, terms including an ordinal number such as first, second, etc. to be used below can be used to describe various elements, but the constituent elements are not limited by the terms. The terms are used only for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, the first component may be referred to as a second component, and similarly, the second component may also be referred to as a first component.
또한, 어떤 구성요소가 다른 구성요소 상에 "형성되어" 있다거나 "적층되어" 있다고 언급된 때에는, 그 다른 구성요소의 표면 상의 전면 또는 일면에 직접 부착되어 형성되어 있거나 적층되어 있을 수도 있지만, 중간에 다른 구성요소가 더 존재할 수도 있다고 이해되어야 할 것이다.Also, when an element is referred to as being "formed" or "laminated" on another element, it may be directly attached or laminated to the front surface or one surface of the other element, It will be appreciated that other components may be present in the < / RTI >
단수의 표현은 문맥상 명백하게 다르게 뜻하지 않는 한, 복수의 표현을 포함한다. 본 출원에서, "포함하다" 또는 "가지다" 등의 용어는 명세서상에 기재된 특징, 숫자, 단계, 동작, 구성요소, 부품 또는 이들을 조합한 것이 존재함을 지정하려는 것이지, 하나 또는 그 이상의 다른 특징들이나 숫자, 단계, 동작, 구성요소, 부품 또는 이들을 조합한 것들의 존재 또는 부가 가능성을 미리 배제하지 않는 것으로 이해되어야 한다.The singular expressions include plural expressions unless the context clearly dictates otherwise. In the present application, the terms "comprises" or "having" and the like are used to specify that there is a feature, a number, a step, an operation, an element, a component or a combination thereof described in the specification, But do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.
본 명세서에서 "원자가결합"이란 별도의 정의가 없는 한, 단일결합, 이중결합 또는 삼중결합을 의미한다.As used herein, "atomic bond" means a single bond, a double bond or a triple bond, unless otherwise defined.
상기 "치환된"이란 적어도 하나의 수소원자가 중수소, C1 내지 C30 알킬기, C3 내지 C30 시클로알킬기, C2 내지 C30 헤테로시클로알킬기, C1 내지 C30 할로겐화알킬기, C6 내지 C30 아릴기, C1 내지 C30 헤테로아릴기, C1 내지 C30 알콕시기, C2 내지 C30 알케닐기, C2 내지 C30 알키닐기, C6 내지 C30 아릴옥시기, 실릴옥시기(-OSiR1R2R3: R1, R2, 및 R3는 각각 독립적으로 수소원자, C1 내지 C30 알킬기 또는 C6 내지 C30 아릴기), C1 내지 C30 아실기, C2 내지 C30 아실옥시기, C2 내지 C30 헤테로아릴옥시기, C1 내지 C30 술포닐기, C1 내지 C30 알킬티올기, C6 내지 C30 아릴티올기, C1 내지 C30 헤테로시클로티올기, C1 내지 C30 인산아마이드기, 실릴기(-SiR1R2R3: R1, R2, 및 R3는 각각 독립적으로 수소원자, C1 내지 C30 알킬기 또는 C6 내지 C30 아릴기), 아민기-NRR'(여기에서, R 및 R'은 각각 독립적으로, 수소 원자, C1 내지 C30 알킬기, 및 C6 내지 C30 아릴기로 이루어진 군에서 선택되는 치환기임), 카르복실기, 할로겐기, 시아노기, 니트로기, 아조기, 및 하이드록시기로 이루어진 군에서 선택되는 치환기로 치환된 것을 의미한다.The term "substituted" as used herein means that at least one hydrogen atom is replaced by a substituent selected from the group consisting of deuterium, C1 to C30 alkyl groups, C3 to C30 cycloalkyl groups, C2 to C30 heterocycloalkyl groups, C1 to C30 halogenated alkyl groups, C6 to C30 aryl groups, C1 to C30 heteroaryl groups, C1 to C30 alkoxy groups, C2 to C30 alkenyl groups, C2 to C30 alkynyl group, C6 to C30 aryloxy group, a silyloxy (-OSiR 1 R 2 R 3: R 1, R 2, and R 3 are each independently A C1 to C30 aryl group, a C1 to C30 acyl group, a C2 to C30 acyloxy group, a C2 to C30 hetero aryloxy group, a C1 to C30 sulfonyl group, a C1 to C30 alkylthiol group, a C6 to C30 aryl group, to C30 aryl thiol groups, C1 to C30 heterocycloalkyl thiol group, C1 to C30 phosphoric acid amide group, a silyl group (-SiR 1 R 2 R 3: R 1, R 2, and R 3 are each independently a hydrogen atom, C1 to C30 alkyl group or a C6 to C30 aryl group), an amine group -NRR '(wherein R and R' Is a substituent selected from the group consisting of a hydrogen atom, a C1 to C30 alkyl group, and a C6 to C30 aryl group, a carboxyl group, a halogen group, a cyano group, a nitro group, an azo group and a hydroxy group Substituted "
또한 상기 치환기 중 인접한 두 개의 치환기가 융합되어 포화 또는 불포화 고리를 형성할 수도 있다.Further, two adjacent substituents among the substituents may be fused to form a saturated or unsaturated ring.
또한, 상기 "치환 또는 비치환된 C1 내지 C30 알킬기" 또는 "치환 또는 비치환된 C6 내지 C30 아릴기" 등에서의 상기 알킬기 또는 아릴기의 탄소수 범위는 상기 치환기가 치환된 부분을 고려하지 않고 비치환된 것으로 보았을 때의 알킬 부분 또는 아릴 부분을 구성하는 전체 탄소수를 의미하는 것이다. 예컨대, 파라 위치에 부틸기가 치환된 페닐기는 탄소수 4의 부틸기로 치환된 탄소수 6의 아릴기에 해당하는 것을 의미한다.The carbon number range of the alkyl group or aryl group in the above "substituted or unsubstituted C1 to C30 alkyl group" or "substituted or unsubstituted C6 to C30 aryl group" Quot; means the total number of carbon atoms constituting the alkyl moiety or the aryl moiety when it is considered to be " substituted ". For example, a phenyl group substituted with a butyl group at the para position means an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.
또한, 상기 "치환 또는 비치환된 C6 내지 C30 융합된 아릴기" 등에서 상기 융합된 아릴기의 탄소수 범위는 상기 치환기가 치환된 부분을 고려하지 않고 비치환된 것으로 보았을 때 융합되어 부가적으로 새롭게 형성된 아릴 부분을 구성하는 전체 탄소수를 의미하는 것이다.In addition, the carbon number range of the fused aryl group in the "substituted or unsubstituted C6 to C30 fused aryl group" or the like is fused when it is considered that the substituent is not substituted without considering the substituted portion, Quot; means the total number of carbon atoms constituting the aryl moiety.
본 명세서에서 "헤테로"란 별도의 정의가 없는 한, 하나의 작용기 내에 N, O, S 및 P로 이루어진 군에서 선택되는 헤테로 원자를 1 내지 4개 함유하고, 나머지는 탄소인 것을 의미한다.As used herein, unless otherwise defined, it is meant that one functional group contains 1 to 4 heteroatoms selected from the group consisting of N, O, S, and P, and the remainder is carbon.
본 명세서에서 "이들의 조합"이란 별도의 정의가 없는 한, 둘 이상의 치환기가 연결기로 결합되어 있거나, 둘 이상의 치환기가 축합하여 결합되어 있는 것을 의미한다.In the present specification, the term "combination thereof" means that two or more substituents are bonded to each other via a linking group or two or more substituents are condensed and bonded.
본 명세서에서 "수소"란 별도의 정의가 없는 한, 일중수소, 이중수소, 또는 삼중수소를 의미한다. As used herein, "hydrogen" means monohydrogen, double hydrogen, or tritium, unless otherwise defined.
본 명세서에서 "알킬(alkyl)기", "알케닐(alkenyl)기" 또는 "알키닐(alkynyl)기" 란 별도의 정의가 없는 한, 지방족 탄화수소기를 의미한다. The term "alkyl group", "alkenyl group" or "alkynyl group" as used herein means an aliphatic hydrocarbon group unless otherwise defined.
알킬기는 어떠한 이중결합이나 삼중결합을 포함하고 있지 않은 "포화 알킬(saturated alkyl)기" 일 수 있다. The alkyl group may be a "saturated alkyl group" which does not contain any double or triple bonds.
"알케닐(alkenyl)기"는 적어도 두 개의 탄소원자가 적어도 하나의 탄소-탄소 이중 결합으로 이루어진 작용기를 의미하며, "알키닐(alkynyl)기" 는 적어도 두 개의 탄소원자가 적어도 하나의 탄소-탄소 삼중 결합으로 이루어진 작용기를 의미한다."Alkenyl group" means a functional group in which at least two carbon atoms are composed of at least one carbon-carbon double bond, and "alkynyl group" means that at least two carbon atoms have at least one carbon- Quot; means a functional group formed by bonding.
"알케닐렌(alkenylene)기"는 상기 알케닐기의 말단 탄소에 결합된 수소 중 어느 하나가 원자가 결합으로 치환된 작용기를 의미하고, "알키닐렌(alkynylene)기" 는 상기 알키닐기의 말단 탄소에 결합된 수소 중 어느 하나가 원자가 결합으로 치환된 작용기를 의미한다.The term "alkenylene group" means a functional group in which any one of hydrogen bonded to the terminal carbon of the alkenyl group is substituted with a valence bond, and "alkynylene group" means a functional group in which an alkynylene group is bonded to the terminal carbon of the alkynyl group Means a functional group in which any one of the hydrogen atoms is replaced by a valence bond.
포화이든 불포화이든 간에 알킬기, 알케닐기, 또는 알키닐기는 분지형, 직쇄형 또는 환형일 수 있다. The alkyl group, alkenyl group, or alkynyl group, whether saturated or unsaturated, may be branched, straight-chain or cyclic.
알킬기는 C1 내지 C30 알킬기일 수 있다. 보다 구체적으로 C1 내지 C20 알킬기, C1 내지 C10 알킬기 또는 C1 내지 C6 알킬기일 수도 있다.The alkyl group may be a C1 to C30 alkyl group. More specifically, a C1 to C20 alkyl group, a C1 to C10 alkyl group, or a C1 to C6 alkyl group.
예를 들어, C1 내지 C4 알킬기는 알킬쇄에 1 내지 4 개의 탄소원자, 즉, 알킬쇄는 메틸, 에틸, 프로필, 이소-프로필, n-부틸, 이소-부틸, sec-부틸 및 t-부틸로 이루어진 군에서 선택됨을 나타낸다.For example, the C1 to C4 alkyl groups may have 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, Indicating that they are selected from the group.
구체적인 예를 들어 상기 알킬기는 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기, 이소부틸기, t-부틸기, 펜틸기, 헥실기, 에테닐기, 프로페닐기, 부테닐기, 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기 등을 의미한다.Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, ethenyl group, Butyl group, cyclopentyl group, cyclohexyl group, and the like.
“아민기”는 아미노기, 아릴아민기, 알킬아민기, 아릴알킬아민기, 또는 알킬아릴아민기를 포함하고, -NRR'로 표현될 수 있고, 여기에서 R 및 R'은 각각 독립적으로, 수소 원자, C1 내지 C30 알킬기, 및 C6 내지 C30 아릴기로 이루어진 군에서 선택되는 치환기이다.An "amine group" includes an amino group, an arylamine group, an alkylamine group, an arylalkylamine group, or an alkylarylamine group, and may be represented by -NRR ', wherein R and R' , A C1 to C30 alkyl group, and a C6 to C30 aryl group.
"시클로알킬(cycloalkyl)기"는 모노시클릭 또는 융합고리 폴리시클릭(즉, 탄소원자들의 인접한 쌍들을 나눠 가지는 고리) 작용기를 포함한다."Cycloalkyl group" includes monocyclic or fused-ring polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups.
"헤테로시클로알킬(heterocycloalkyl)기"는 시클로알킬기 내에 N, O, S 및 P로 이루어진 군에서 선택되는 헤테로원자를 1 내지 4개 함유하고, 나머지는 탄소인 것을 의미한다. 상기 헤테로시클로알킬기가 융합된 고리(fused ring)인 경우, 융합된 고리 중 적어도 하나의 고리가 상기 헤테로 원자를 1 내지 4개 포함할 수 있다."Heterocycloalkyl group" means that the cycloalkyl group contains 1 to 4 hetero atoms selected from the group consisting of N, O, S and P in the cycloalkyl group, and the remainder is carbon. When the heterocycloalkyl group is a fused ring, at least one ring of the fused rings may contain from 1 to 4 heteroatoms.
"방향족(aromatic)기"는 고리 형태인 작용기의 모든 원소가 p-오비탈을 가지고 있으며, 이들 p-오비탈이 공액(conjugation)을 형성하고 있는 작용기를 의미한다. 구체적인 예로 아릴기와 헤테로아릴기가 있다. "An aromatic group" means a functional group in which all elements of a functional group in the form of a ring have a p-orbital, and these p-orbital forms a conjugation. Specific examples thereof include an aryl group and a heteroaryl group.
"아릴(aryl)기"는 모노시클릭 또는 융합 고리 폴리시클릭(즉, 탄소원자들의 인접한 쌍들을 나눠 가지는 고리) 작용기를 포함한다. An "aryl group" includes a monocyclic or fused ring polycyclic (i. E., A ring that divides adjacent pairs of carbon atoms) functional groups.
"헤테로아릴(heteroaryl)기"는 아릴기 내에 N, O, S 및 P로 이루어진 군에서 선택되는 헤테로원자를 1 내지 4개 함유하고, 나머지는 탄소인 것을 의미한다. 상기 헤테로아릴기가 융합된 고리(fused ring)인 경우, 융합된 고리 중 적어도 하나의 고리가 상기 헤테로 원자를 1 내지 4개 포함할 수 있다. "Heteroaryl group" means that the aryl group contains 1 to 4 hetero atoms selected from the group consisting of N, O, S and P, and the remainder is carbon. When the heteroaryl group is a fused ring, at least one ring of the fused rings may contain from 1 to 4 heteroatoms.
아릴기 및 헤테로아릴기에서 고리의 원자수는 탄소수 및 비탄소원자수의 합이다.In the aryl group and the heteroaryl group, the number of atoms in the ring is the sum of carbon number and non-carbon atom number.
"알킬아릴기" 또는 "아릴알킬기"와 같이 조합하여 사용할 때, 상기에 든 각각의 알킬 및 아릴의 용어는 상기 나타낸 의미와 내용을 가진다.When used in combination, such as "alkylaryl" or "arylalkyl group ", the terms alkyl and aryl of each of the above have the meanings and contents indicated above.
"아릴알킬기"이란 용어는 벤질과 같은 아릴 치환된 알킬 라디칼을 의미하며 알킬기에 포함된다.The term "arylalkyl group " means an aryl substituted alkyl radical, such as benzyl, and is included in the alkyl group.
"알킬아릴기"이란 용어는 알킬 치환된 아릴 라디칼을 의미하며 아릴기에 포함된다.The term "alkylaryl group " means an alkyl substituted aryl radical and is included in the aryl group.
이하, 본 발명의 실시예를 첨부도면을 참조하여 설명하기로 하며, 첨부 도면을 참조하여 설명함에 있어, 동일하거나 대응하는 구성 요소는 동일한 도면번호를 부여하고 이에 대한 중복되는 설명은 생략하기로 한다.DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT Hereinafter, embodiments of the present invention will be described with reference to the accompanying drawings. Referring to the accompanying drawings, the same or corresponding components are denoted by the same reference numerals, .
본 발명의 하나의 측면에 따르면, 하기 구조식 1로 표시되는 유기전계발광소자용 화합물이 제공될 수 있다.According to one aspect of the present invention, a compound for an organic electroluminescence device represented by the following
[구조식 1][Structural formula 1]
구조식 1에서,In
R1 내지 R6은 서로 같거나 다르고, R1 내지 R6은 각각 독립적으로 수소원자, 중수소원자, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이고,R 1 to R 6 are the same as or different from each other and each of R 1 to R 6 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
L은 원자가결합, 치환 또는 비치환된 C1 내지 C30 알킬렌기, 치환 또는 비치환된 C3 내지 C30 시클로알킬렌기, 치환 또는 비치환된 C2 내지 C30 헤테로시클로알킬렌기, 치환 또는 비치환된 C6 내지 C30 아릴렌기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로아릴렌기이고,L is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C2 to C30 heterocycloalkylene group, a substituted or unsubstituted C6 to C30 aryl Or a substituted or unsubstituted C2 to C30 heteroarylene group,
X는 산소원자 또는 황원자이고,X is an oxygen atom or a sulfur atom,
Ar1 내지 Ar3은 서로 같거나 다르고, Ar1 내지 Ar3은 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기일 수 있다.Ar 1 to Ar 3 are the same or different from each other and Ar 1 to Ar 3 each independently represent a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group.
바람직하게는, 상기 구조식 1로 표시되는 화합물은 하기 구조식 2로 표시되는 화합물일 수 있다. Preferably, the compound represented by the structural formula (1) may be a compound represented by the following structural formula (2).
[구조식 2][Structural formula 2]
구조식 2에서,In formula 2,
R1 내지 R6은 서로 같거나 다르고, R1 내지 R6은 각각 독립적으로 수소원자, 중수소원자, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이고,R 1 to R 6 are the same as or different from each other and each of R 1 to R 6 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
L은 원자가결합, 치환 또는 비치환된 C1 내지 C30 알킬렌기, 치환 또는 비치환된 C3 내지 C30 시클로알킬렌기, 치환 또는 비치환된 C2 내지 C30 헤테로시클로알킬렌기, 치환 또는 비치환된 C6 내지 C30 아릴렌기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로아릴렌기이고,L is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C2 to C30 heterocycloalkylene group, a substituted or unsubstituted C6 to C30 aryl Or a substituted or unsubstituted C2 to C30 heteroarylene group,
X는 산소원자 또는 황원자이고,X is an oxygen atom or a sulfur atom,
Ar1 내지 Ar3은 서로 같거나 다르고, Ar1 내지 Ar3은 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기일 수 있다.Ar 1 to Ar 3 are the same or different from each other and Ar 1 to Ar 3 each independently represent a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group.
바람직하게는, 상기 구조식 1로 표시되는 화합물은 하기 구조식 3으로 표시되는 화합물일 수 있다. Preferably, the compound represented by
[구조식 3][Structural Formula 3]
구조식 3에서,In Structure 3,
R1 내지 R6은 서로 같거나 다르고, R1 내지 R6은 각각 독립적으로 수소원자, 중수소원자, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이고,R 1 to R 6 are the same as or different from each other and each of R 1 to R 6 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
L은 원자가결합, 치환 또는 비치환된 C1 내지 C30 알킬렌기, 치환 또는 비치환된 C3 내지 C30 시클로알킬렌기, 치환 또는 비치환된 C2 내지 C30 헤테로시클로알킬렌기, 치환 또는 비치환된 C6 내지 C30 아릴렌기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로아릴렌기이고,L is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C2 to C30 heterocycloalkylene group, a substituted or unsubstituted C6 to C30 aryl Or a substituted or unsubstituted C2 to C30 heteroarylene group,
X는 산소원자 또는 황원자이고,X is an oxygen atom or a sulfur atom,
Ar1 내지 Ar3은 서로 같거나 다르고, Ar1 내지 Ar3은 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기일 수 있다. Ar 1 to Ar 3 are the same or different from each other and Ar 1 to Ar 3 each independently represent a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group.
또한 바람직하게는, Ar1 내지 Ar3은 서로 같거나 다르고, Ar1 내지 Ar3은 각각 독립적으로 
R7 내지 R38은 서로 같거나 다르고, R7 내지 R38은 각각 독립적으로 수소원자, 중수소원자, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기일 수 있다. R 7 to R 38 are the same or different from each other and each of R 7 to R 38 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
상기 치환 또는 비치환된 C1 내지 C30 헤테로아릴기의 예는 치환 또는 비치환된 피리디닐기, 치환 또는 비치환된 피리미디닐기, 치환 또는 비치환된 트리아지닐기, 치환 또는 비치환된 싸이오페닐기, 치환 또는 비치환된 피롤릴기, 치환 또는 비치환된 벤조싸이오페닐기, 치환 또는 비치환된 인돌릴기, 치환 또는 비치환된 이미다조[1,2-a]피리디닐기, 치환 또는 비치환된 벤지이미다졸릴기, 치환 또는 비치환된 인다졸릴기, 치환 또는 비치환된 페노티아지닐기, 치환 또는 비치환된 페나지닐기, 치환 또는 비치환된 카바졸릴기, 치환 또는 비치환된 디벤조싸이오페닐기, 치환 또는 비치환된 이미다졸릴기, 치환 또는 비치환된 트리아졸릴기, 치환 또는 비치환된 테트라졸릴기, 치환 또는 비치환된 옥사다이아졸릴기, 치환 또는 비치환된 옥사트리아졸릴기, 치환 또는 비치환된 싸이아트리아졸릴기, 치환 또는 비치환된 벤조트리아졸릴기, 치환 또는 비치환된 피라지닐기, 치환 또는 비치환된 피리다지닐기, 치환 또는 비치환된 퓨리닐기, 치환 또는 비치환된 퀴놀리닐기, 치환 또는 비치환된 이소퀴놀리닐기, 치환 또는 비치환된 프탈라지닐기, 치환 또는 비치환된 나프피리디닐기, 치환 또는 비치환된 퀴녹살리닐기, 치환 또는 비치환된 퀴나졸리닐기, 치환 또는 비치환된 아크리디닐기, 또는 치환 또는 비치환된 페난트롤리닐기, 바람직하게는 치환 또는 비치환된 피리디닐기, 치환 또는 비치환된 피리미디닐기, 치환 또는 비치환된 트리아지닐기, 치환 또는 비치환된 싸이오페닐기, 치환 또는 비치환된 피롤릴기, 치환 또는 비치환된 벤조싸이오페닐기, 치환 또는 비치환된 인돌릴기, 치환 또는 비치환된 이미다조[1,2-a]피리디닐기, 치환 또는 비치환된 벤지이미다졸릴기, 치환 또는 비치환된 인다졸릴기, 치환 또는 비치환된 페노티아지닐기, 치환 또는 비치환된 페나지닐기, 치환 또는 비치환된 카바졸릴기, 또는 치환 또는 비치환된 디벤조싸이오페닐기일 수 있다.Examples of the substituted or unsubstituted C1 to C30 heteroaryl group include a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted thiophenyl group , A substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted imidazo [1,2-a] pyridinyl group, a substituted or unsubstituted A substituted or unsubstituted indazolyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzoyl group, Substituted or unsubstituted imidazolyl groups, substituted or unsubstituted thiazolyl groups, substituted or unsubstituted tetrazolyl groups, substituted or unsubstituted oxadiazolyl groups, substituted or unsubstituted oxatriazolyl groups, However, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thiazolyl group, A substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted naphthyridinyl group, Or a substituted or unsubstituted phenanthrolinyl group, preferably a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted aryidinyl group, a substituted or unsubstituted pyrazolinyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, A substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted phenothiazyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted benzothiazolyl group, , A substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzothiophenyl group.
상기 유기전계발광소자용 화합물은 하기 화학식으로 표시되는 화합물 1 내지 70 중에서 선택된 어느 하나일 수 있으나, 여기에 한정되지 않는다.The organic electroluminescent device compound may be any one selected from
도 1 및 2를 참고하면, 본 발명의 실시예에 따른 유기전계발광소자용 화합물을 포함하는 유기전계발광소자(1)가 제공될 수 있다.Referring to FIGS. 1 and 2, an
본 발명의 다른 실시예에 따르면, 상기 유기전계발광소자는 제1전극(110); 제2전극(150); 및 상기 제1전극과 제2전극 사이에 단수 또는 복수의 유기물층(130)을 포함하며, 상기 단수 또는 복수의 유기물층(130) 중에서 선택된 1종 이상의 유기물층은 본 발명에 따른 유기발광소자용 화합물을 포함할 수 있다.According to another embodiment of the present invention, the organic electroluminescent device includes a
여기서, 상기 단수 또는 복수의 유기물층(130)은 발광층(134)을 포함할 수 있다. Here, the single or plural
또한 상기 복수의 유기물층(130)은 발광층(134)을 포함하고, 상기 복수의 유기물층은 전자주입층(131), 전자수송층(132), 정공차단층(133), 전자차단층(135), 정공수송층(136) 및 정공주입층(137) 중에서 선택된 1종 이상을 추가로 포함할 수 있다.The plurality of
상기 발광층(134)은 호스트와 도펀트를 포함할 수 있다.The
상기 유기전계발광소자는 바람직하게는 투명기판에 의하여 지지된다. 투명기판의 재료로는 양호한 기계적 강도, 열안정성 및 투명성을 갖는 한 특별한 제한은 없다. 구체적인 예를 들면, 유리, 투명 플라스틱 필름 등을 사용할 수 있다.The organic electroluminescent device is preferably supported by a transparent substrate. The material of the transparent substrate is not particularly limited as long as it has good mechanical strength, thermal stability and transparency. Specific examples thereof include glass, transparent plastic film, and the like.
본 발명의 유기전계발광소자의 양극재료로서는 4eV 이상의 일함수를 갖는 금속, 합금, 전기전도성 화합물 또는 이의 혼합물을 사용할 수 있다. 구체적으로는 금속인 Au 또는 CuI, ITO(인듐 주석 산화물), SnO2 및 ZnO와 같은 투명 전도성 재료를 들 수 있다. 양극 필름의 두께는 10 내지 200nm 가 바람직하다.As the cathode material of the organic electroluminescent device of the present invention, a metal, an alloy, an electroconductive compound or a mixture thereof having a work function of 4 eV or more can be used. Specifically, transparent conductive materials such as Au or CuI, ITO (indium tin oxide), SnO 2 and ZnO, which are metals, can be mentioned. The thickness of the positive electrode film is preferably 10 to 200 nm.
본 발명의 유기전계발광소자의 음극 재료로서는 4eV 미만의 일함수를 갖는 금속, 합금, 전기 전도성 화합물 또는 이의 혼합물을 사용할 수 있다. 구체적으로는, Na, Na-K 합금, 칼슘, 마그네슘, 리튬, 리튬 합금, 인듐, 알루미늄, 마그네슘 합금, 알루미늄 합금을 들 수 있다. 이외에, 알루미늄/AlO2, 알루미늄/리튬, 마그네슘/은 또는 마그네슘/인듐 등도 사용될 수 있다. 음극필름의 두께는 10 내지 200nm 가 바람직하다.As the anode material of the organic electroluminescent device of the present invention, a metal, an alloy, an electrically conductive compound or a mixture thereof having a work function of less than 4 eV may be used. Specifically, Na, Na-K alloy, calcium, magnesium, lithium, lithium alloy, indium, aluminum, magnesium alloy and aluminum alloy can be mentioned. In addition, aluminum / AlO 2 , aluminum / lithium, magnesium / silver or magnesium / indium may be used. The thickness of the negative electrode film is preferably 10 to 200 nm.
유기 EL 소자의 발광효율을 높이기 위해서는 하나 이상의 전극은 바람직하게는 10% 이상의 광투과율을 가지는 것이 바람직하다. 전극의 쉬트저항은 바람직하게는 수백 Ω/mm 이하이다. 전극의 두께는 10nm 내지 1㎛, 보다 바람직하게는 10 내지 400nm 이다. 이러한 전극은 화학적 기상증착(CVD), 물리적 기상증착(PVD) 등의 기상증착법 또는 스퍼터링법을 통하여 상기한 전극 재료를 박막으로 형성하여 제조할 수 있다.In order to increase the luminous efficiency of the organic EL device, at least one electrode preferably has a light transmittance of 10% or more. The sheet resistance of the electrode is preferably several hundreds? / Mm or less. The thickness of the electrode is 10 nm to 1 탆, more preferably 10 to 400 nm. Such an electrode can be manufactured by forming the electrode material into a thin film by a vapor deposition method such as chemical vapor deposition (CVD) or physical vapor deposition (PVD) or a sputtering method.
또한 본 발명의 목적에 적합하게 본 발명의 유기전계발광소자용 화합물이 사용될 때, 공지된 정공수송 물질, 정공주입 물질, 발광층 물질, 발광층의 호스트 물질, 전자수송 물질, 및 전자주입 물질이 상기 각각의 유기물층에서 단독으로 사용되거나 또는 본 발명의 유기전계발광소자용 화합물과 선택적으로 병행하여 사용될 수 있다.When the compound for an organic electroluminescence device of the present invention is used for the purpose of the present invention, the known hole transporting material, hole injecting material, light emitting layer material, host material of the light emitting layer, electron transporting material, Or may be used in combination with the organic electroluminescent device compound of the present invention selectively.
정공 수송 물질로서 N,N-dicarbazolyl-3,5-benzene(mCP), poly(3,4-ethylenedioxythiophene):polystyrenesulfonate (PEDOT:PSS), N, N’-di(1-naphthyl)-N,N’-diphenylbenzidine(NPD), N,N'-디페닐-N,N'-디(3-메틸페닐)-4,4'-디아미노비페닐(TPD), N,N'-디페닐-N,N'-디나프틸-4,4'-디아미노비페닐, N,N,N'N'-테트라-p-톨릴-4,4'-디아미노비페닐, N,N,N'N'-테트라페닐-4,4'-디아미노비페닐, 코퍼(II)1,10,15,20-테트라페닐-21H,23H-포피린 등과 같은 포피린(porphyrin)화합물 유도체, 주쇄 또는 측쇄내에 방향족 3차아민을 갖는 중합체, 1,1-비스(4-디-p-톨릴아미노페닐)시클로헥산, N,N,N-트리(p-톨릴)아민, 4, 4', 4'-트리스[N-(3-메틸페닐)-N-페닐아미노]트리페닐아민과 같은 트리아릴아민 유도체, N-페닐카르바졸 및 폴리비닐카르바졸과 같은 카르바졸 유도체, 무금속 프탈로시아닌, 구리프탈로시아닌과 같은 프탈로시아닌 유도체, 스타버스트 아민 유도체, 엔아민스틸벤계 유도체, 방향족 삼급아민과 스티릴 아민 화합물의 유도체, 및 폴리실란 등을 들 수 있다.N-dicarbazolyl-3,5-benzene (mCP), poly (3,4-ethylenedioxythiophene): polystyrenesulfonate (PEDOT: PSS), N, N'- (NPD), N, N'-diphenyl-N, N'-di (3-methylphenyl) -4,4'- diaminobiphenyl (TPD) N, N'N'-tetra-p-tolyl-4,4'-diaminobiphenyl, N, N'N'N'N'- Porphyrin compound derivatives such as tetraphenyl-4,4'-diaminobiphenyl, copper (II) 1,10,15,20-tetraphenyl-21H, 23H-porphyrin and the like, aromatic tertiary (4-di-p-tolylaminophenyl) cyclohexane, N, N, N-tri (3-methylphenyl) -N-phenylamino] triphenylamine, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, phthalocyanine derivatives such as nonmetal phthalocyanine and copper phthalocyanine, An aminostilbene derivative, a derivative of an aromatic tertiary amine and a styrylamine compound, and polysilane.
전자 수송 물질로서 diphenylphosphine oxide-4-(triphenylsilyl)phenyl (TSPO1), Alq3, 2,5-디아릴 실롤 유도체(PyPySPyPy), 퍼플루오리네이티드 화합물(PF-6P), Octasubstituted cyclooctatetraene 화합물(COTs)을 들 수 있다.The diphenylphosphine oxide-4- (triphenylsilyl) phenyl (TSPO1), Alq 3, 2,5- diaryl silole derivatives (PyPySPyPy), perfluoro rineyi suited compound (PF-6P), Octasubstituted cyclooctatetraene compound (COTs) as an electron transport material .
본 발명의 유기전계발광소자에 있어서, 전자 주입층, 전자 수송층, 정공 수송층 및 정공 주입층은 상기한 화합물의 하나 이상의 종류를 함유하는 단일 층으로 형성되거나, 또는 상호 적층된, 상이한 종류의 화합물을 함유하는 복수의 층으로 구성될 수 있다.In the organic electroluminescent device of the present invention, the electron injecting layer, the electron transporting layer, the hole transporting layer, and the hole injecting layer may be formed of a single layer containing at least one kind of the above-mentioned compounds, And the like.
발광재료로서 예를 들면 축광 형광재료, 형광증백제, 레이저 색소, 유기 신틸레이터 및 형광 분석용 시약을 들 수 있다. 구체적으로는, 카바졸계 화합물, 포스핀옥사이드계 화합물, 카바졸계 포스핀옥사이드 화합물, bis((3,5-difluoro-4-cyanophenyl)pyridine) iridium picolinate(FCNIrpic), tris(8-hydroxyquinoline) aluminum(Alq3), 안트라센, 페난트렌, 피렌, 크리센, 페릴렌, 코로넨, 루브렌 및 퀴나크리돈과 같은 폴리아로마틱 화합물, 퀴터페닐과 같은 올리고페닐렌 화합물, 1,4-비스 (2-메틸스티릴)벤젠, 1,4-비스(4-메틸스티릴)벤젠, 1,4-비스(4-메틸-5-페닐-2-옥사졸릴)벤젠, 1,4-비스(5-페닐-2-옥사졸릴)벤젠, 2,5-비스(5-t-부틸-2-벤즈옥사졸릴)사이오펜, 1,4-디페닐-1,3-부타디엔, 1,6-디페닐-1,3,5-헥사트리엔,1,1,4,4-테트라페닐-1,3-부타디엔과 같은 액체신틸레이션용 신틸레이터, 옥신 유도체의 금속착체, 쿠마린 색소, 디시아노메틸렌피란 색소, 디시아노메틸렌사이오피란 색소, 폴리메틴 색소, 옥소벤즈안트라센 색소, 크산텐 색소, 카르보스티릴 색소, 페릴렌 색소, 옥사진 화합물, 스틸벤 유도체, 스피로 화합물, 옥사디아졸 화합물 등을 들 수 있다.Examples of the light emitting material include a phosphorescent fluorescent material, a fluorescent whitening agent, a laser dye, an organic scintillator, and a reagent for fluorescence analysis. Specifically, a carbazole compound, a phosphine oxide compound, a carbazole-based phosphine oxide compound, bis (3,5-difluoro-4-cyanophenyl) pyridine, iridium picolinate (FCNIrpic), tris (8-hydroxyquinoline) aluminum Alq 3 ), polyaromatic compounds such as anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene and quinacridone, oligophenylene compounds such as quaterphenyl, 1,4- Bis (4-methylstyryl) benzene, 1,4-bis (4-methyl- Bis (5-t-butyl-2-benzoxazolyl) thiophene, 1,4-diphenyl-1,3-butadiene, 1,6- Liquid scintillation scintillators such as 3,5-hexatriene and 1,1,4,4-tetraphenyl-1,3-butadiene, metal complexes of oxine derivatives, coumarin dyes, dicyanomethylenepyran dyes, dicyanomethylene Cyopyran pigment, polymethine pigment, oxobenzanthracene There may be mentioned a colorant, a xanthene colorant, a carbostyryl colorant, a perylene colorant, an oxazine compound, a stilbene derivative, a spiro compound, and an oxadiazole compound.
본 발명의 유기 EL 소자를 구성하는 각 층은 진공 증착, 스핀 코팅 또는 캐스팅과 같은 공지된 방법을 통하여 박막으로 형성시키거나, 각 층에서 사용되는 재료를 이용하여 제조할 수 있다. 이들 각층의 막두께에 대해서는 특별한 제한은 없으며, 재료의 특성에 따라 알맞게 선택할 수 있으나, 보통 2nm 내지 5,000nm의 범위에서 결정될 수 있다.Each layer constituting the organic EL device of the present invention can be formed into a thin film through a known method such as vacuum deposition, spin coating or casting, or can be manufactured using a material used in each layer. The thickness of each of these layers is not particularly limited and may be appropriately selected according to the characteristics of the material, but may be determined usually in the range of 2 nm to 5,000 nm.
본 발명의 따른 유기전계발광소자용 화합물은 진공 증착법에 의하여 형성될 수 있으므로, 박막 형성 공정이 간편하고, 핀홀(pin hole)이 거의 없는 균질한 박막으로 용이하게 얻을 수 있는 장점이 있다.The compound for an organic electroluminescence device according to the present invention can be formed by a vacuum deposition method, so that it is advantageous that a thin film forming process is simple and a homogeneous thin film having almost no pinhole can be easily obtained.
[실시예][Example]
이하, 실시예를 통하여 본 발명에 따른 유기전계발광소자용 화합물 및 이를 포함하는 유기전계발광소자의 제조방법을 더욱 구체적으로 설명한다. 그러나 이는 예시를 위한 것으로서 이에 의하여 본 발명의 범위가 한정되는 것이 아니다.Hereinafter, the compound for an organic electroluminescent device according to the present invention and the method for manufacturing the organic electroluminescent device including the same will be described in more detail with reference to the following examples. However, this is for the purpose of illustration only and is not intended to limit the scope of the invention.
제조예Manufacturing example 1: 중간체(1) N-( 1: Intermediate (1) N- ( 디벤조퓨란Dibenzofuran -4-일)Yl) 아세트아마이드의Acetamide 합성 synthesis
질소 분위기 하에서 1L 둥근 바닥 3구 플라스크에 4-브로모디벤조퓨란 25.0g, 아세트아마이드 23.9g, 요오드화 구리(I) 19.3g, 트랜스-1,2-디아미노시클로헥산 11.6g, 탄산 칼륨 56.0g, 톨루엔 300mL를 넣고 환류 하에서 36시간 교반하였다. 반응 완료 후, 반응액을 냉각시키고 필터 및 감압증류 하여 중간체(1) 13.8g을 얻었다. (수율 61%)In a 1 L round-bottomed three-necked flask, 25.0 g of 4-bromodibenzofuran, 23.9 g of acetamide, 19.3 g of copper (I) iodide, 11.6 g of trans-1,2-diaminocyclohexane, 56.0 g of potassium carbonate, 300 mL of toluene was added, and the mixture was stirred under reflux for 36 hours. After completion of the reaction, the reaction solution was cooled, filtered and distilled under reduced pressure to obtain 13.8 g of intermediate (1). (Yield: 61%)
MS (ESI) : [M+H]+ 226MS (ESI): [M + H] < + > 226
제조예 2: 중간체(2) N-(1-브로모디벤조퓨란-4-일)아세트아마이드의 합성Preparation Example 2: Intermediate (2) Synthesis of N- (1-bromodibenzofuran-4-yl) acetamide
500ml 둥근 바닥 3구 플라스크에 중간체(1) 13.8g과 아세트산 220ml의 혼합용액에 브롬 9.8g 및 아세트산 70mL의 혼합용액을 상온에서 서서히 적가한다. 상온에서 24시간 교반 후 반응액을 필터 및 물로 세척하여 중간체(2) 18.2g을 얻었다.(수율 98%) A mixed solution of 9.8 g of bromine and 70 ml of acetic acid is slowly added dropwise to a 500 ml round bottom three-necked flask in a mixed solution of 13.8 g of intermediate (1) and 220 ml of acetic acid at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was washed with a filter and water to obtain 18.2 g of intermediate (2) (yield: 98%).
MS (ESI) : [M+H]+ 304MS (ESI): [M + H] < + > 304
제조예 3: 중간체(3) 1-브로모디벤조퓨란-4-아민의 합성Preparation Example 3: Synthesis of intermediate (3) 1-Bromodibenzofuran-4-amine
1L 둥근 바닥 3구 플라스크에 중간체(2) 20.0g, 수산화 칼륨 18.2g, 테트라하이드로퓨란 200ml, 에탄올 200mL 및 물 200ml를 넣고 환류 하에서 8시간 동안 교반한다. 반응액을 냉각 후 물과 디클로로메탄으로 층분리한 다음 디클로로메탄층을 농축한다. 디클로로메탄과 n-헥산 혼합용매로 컬럼크로마토그래피를 실시하여 중간체(3) 15.7g을 얻었다.(수율 91%)20.0 g of the intermediate (2), 18.2 g of potassium hydroxide, 200 ml of tetrahydrofuran, 200 ml of ethanol and 200 ml of water were placed in a 1 L round bottom three-necked flask and stirred under reflux for 8 hours. After cooling, the reaction solution is separated into water and dichloromethane, and the dichloromethane layer is concentrated. Column chromatography was performed with a mixed solvent of dichloromethane and n-hexane to obtain 15.7 g of intermediate (3) (yield: 91%).
MS (ESI) : [M+H]+ 262MS (ESI): [M + H] < + > 262
제조예Manufacturing example 4: 중간체(4) 2-(1- 4: Intermediate (4) 2- (1- 브로모디벤조퓨란Bromodibenzofuran -4-일)-4,4,5,5-Yl) -4,4,5,5- 테트라메틸Tetramethyl -1,3,2-디옥사보로란-1,3,2-dioxabororane
250mL 둥근 바닥 3구 플라스크에 중간체(4) 15.7g, 비스(피나콜라토)디보론 18.3g, 아세토니트릴 165ml를 넣고 0℃에서 부틸니트라이트 10.3g을 서서히 적가한다. 적가 종료 후 0℃에서 30분 교반한 다음 80℃로 올려 2시간 교반한다. 반응액을 농축 후 에틸아세테이트와 n-헥산 혼합용매로 컬럼크로마토그래피를 실시하여 중간체(4) 8.9g을 얻었다.(수율 39%)15.7 g of the intermediate (4), 18.3 g of bis (pinacolato) diboron and 165 ml of acetonitrile are placed in a 250-mL round-bottomed three-necked flask, and 10.3 g of butyl nitrite is slowly added dropwise at 0 ° C. After completion of dropwise addition, the mixture was stirred at 0 ° C for 30 minutes, then heated to 80 ° C and stirred for 2 hours. The reaction mixture was concentrated and then subjected to column chromatography using a mixed solvent of ethyl acetate and n-hexane to obtain 8.9 g of intermediate (4) (yield: 39%).
MS (ESI) : [M+H]+ 373MS (ESI): [M + H] < + > 373
제조예 5: 중간체(5) 1-브로모-4-페닐디벤조퓨란의 합성Preparation Example 5: Intermediate (5) Synthesis of 1-bromo-4-phenyldibenzofuran
질소 분위기 하에서 250ml 둥근바닥 3구 플라스크에 중간체(4) 5.3g, 아이오도벤젠 6.0g, 탄산 칼륨 5.9g, 테트라키스트리페닐포스핀팔라듐(0) 0.5g, 테트라하이드로퓨란 150ml 및 물 50ml를 넣고 24시간 동안 환류시켜 주었다. 반응액을 냉각한 후 디클로로메탄과 물로 추출하고, 추출된 용액을 농축하였다. n-헥산으로 컬럼크로마토그래피를 실시한 용액을 농축하여 중간체(5) 2.8g을 얻었다. (수율 62%)Under a nitrogen atmosphere, 5.3 g of intermediate (4), 6.0 g of iodobenzene, 5.9 g of potassium carbonate, 0.5 g of tetrakis (triphenylphosphine) palladium (0), 150 ml of tetrahydrofuran and 50 ml of water were placed in a 250 ml three- And refluxed for 24 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The solution was subjected to column chromatography with n-hexane and then concentrated to obtain 2.8 g of Intermediate (5). (Yield: 62%)
MS (ESI) : [M+H]+ 323MS (ESI): [M + H] < + > 323
제조예 6: 중간체(6) 3-(1-브로모디벤조퓨란-4-일)-9-페닐-9H-카바졸의 합성Preparation 6: Intermediate (6) Synthesis of 3- (1-bromodibenzofuran-4-yl) -9-phenyl-9H-carbazole
질소 분위기 하에서 250ml 둥근바닥 3구 플라스크에 중간체(4) 5.3g, 3-아이오도-9-페닐-9H-카바졸 5.3g, 탄산 칼륨 5.9g, 테트라키스트리페닐포스핀팔라듐(0) 0.5g, 테트라하이드로퓨란 150ml 및 물 50ml를 넣고 24시간 동안 환류시켜 주었다. 반응액을 냉각한 후 디클로로메탄과 물로 추출하고, 추출된 용액을 농축하였다. 디클로로메탄과 n-헥산 혼합용매로 컬럼크로마토그래피를 실시한 용액을 농축하여 중간체(6) 2.1g을 얻었다. (수율 30%)5.3 g of the intermediate (4), 5.3 g of 3-iodo-9-phenyl-9H-carbazole, 5.9 g of potassium carbonate, and 0.5 g of tetrakistriphenylphosphine palladium (0) in a 250 ml three- , 150 ml of tetrahydrofuran and 50 ml of water, and the mixture was refluxed for 24 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The resultant solution was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane and then concentrated to obtain 2.1 g of intermediate (6). (Yield: 30%)
MS (ESI) : [M+H]+ 488MS (ESI): [M + H] < + > 488
제조예Manufacturing example 7: 중간체(7) N-([1,1'-비페닐]-4-일)-N-(4-(1- 7: Intermediate (7) N - ([1,1'-biphenyl] -4-yl) -N- 브로모디벤조퓨란Bromodibenzofuran -4-일)페닐)-[1,1'-비페닐]-4-아민의 합성Yl) phenyl) - [1,1'-biphenyl] -4-amine Synthesis of
질소 분위기 하에서 250ml 둥근바닥 3구 플라스크에 중간체(4) 3.7g, N-([1,1'-바이페닐]-4-일)-N-(4-아이오도페닐)-[1,1'-바이페닐]-4-아민 5.2g, 탄산 칼륨 4.1g, 테트라키스트리페닐포스핀팔라듐(0) 0.3g, 테트라하이드로퓨란 100ml 및 물 33ml를 넣고 18시간 동안 환류시켜 주었다. 반응액을 냉각한 후 디클로로메탄과 물로 추출하고, 추출된 용액을 농축하였다. 디클로로메탄과 n-헥산 혼합용매로 컬럼크로마토그래피를 실시한 용액을 농축하여 중간체(7) 3.9g을 얻었다. (수율 61%)In a 250 ml round-bottomed, three-necked flask, under nitrogen atmosphere, 3.7 g of intermediate (4), 3.7 g of N- (1,1'-biphenyl- -Biphenyl] -4-amine, 4.1 g of potassium carbonate, 0.3 g of tetrakistriphenylphosphine palladium (0), 100 ml of tetrahydrofuran and 33 ml of water were added and the mixture was refluxed for 18 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The resultant solution was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane and then concentrated to obtain 3.9 g of intermediate (7). (Yield: 61%)
MS (ESI) : [M+H]+ 642MS (ESI): [M + H] < + > 642
제조예 8: 중간체(8) N-(디벤조티오펜-4-일)아세트아마이드의 합성 합성Preparation Example 8: Synthesis of intermediate (8) N- (dibenzothiophen-4-yl) acetamide Synthesis
질소 분위기 하에서 1L 둥근 바닥 3구 플라스크에 4-브로모디벤조티오펜 26.6g, 아세트아마이드 23.9g, 요오드화 구리(I) 19.3g, 트랜스-1,2-디아미노시클로헥산 11.6g, 탄산 칼륨 56.0g, 톨루엔 300mL를 넣고 환류 하에서 36시간 교반하였다. 반응 완료 후, 반응액을 냉각시키고 필터 및 감압증류 하여 중간체(8) 13.4g을 얻었다. (수율 55%)In a 1 L round-bottomed three-necked flask, 26.6 g of 4-bromodibenzothiophene, 23.9 g of acetamide, 19.3 g of copper (I) iodide, 11.6 g of trans-1,2-diaminocyclohexane, 56.0 g And 300 mL of toluene, and the mixture was stirred under reflux for 36 hours. After completion of the reaction, the reaction solution was cooled, filtered and distilled under reduced pressure to obtain 13.4 g of intermediate (8). (Yield: 55%)
MS (ESI) : [M+H]+ 241MS (ESI): [M + H] < + > 241
제조예 9: 중간체(9) N-(1-브로모디벤조티오펜-4-일)아세트아마이드의 합성Preparation Example 9: Intermediate (9) Synthesis of N- (1-bromodibenzothiophen-4-yl) acetamide
500ml 둥근 바닥 3구 플라스크에 중간체(8) 13.4g과 아세트산 200ml의 혼합용액에 브롬 8.9g 및 아세트산 60mL의 혼합용액을 상온에서 서서히 적가한다. 상온에서 24시간 교반 후 반응액을 필터 및 물로 세척하여 중간체(9) 17.6g을 얻었다.(수율 99%)A mixed solution of bromine (8.9 g) and acetic acid (60 mL) is slowly added dropwise to a 500 ml round-bottomed three-necked flask with a mixed solution of 13.4 g of intermediate (8) and 200 ml of acetic acid at room temperature. After stirring at room temperature for 24 hours, the reaction solution was washed with a filter and water to obtain 17.6 g of intermediate (9) (yield: 99%).
MS (ESI) : [M+H]+ 320MS (ESI): [M + H] < + > 320
제조예 10: 중간체(10) 1-브로모디벤조티오펜-4-아민의 합성Preparation 10: Intermediate (10) Synthesis of 1-bromodibenzothiophen-4-amine
1L 둥근 바닥 3구 플라스크에 중간체(9) 17.6g, 수산화 칼륨 15.6g, 테트라하이드로퓨란 200ml, 에탄올 200mL 및 물 200ml를 넣고 환류 하에서 8시간 동안 교반한다. 반응액을 냉각 후 물과 디클로로메탄으로 층분리한 다음 디클로로메탄층을 농축한다. 디클로로메탄과 n-헥산 혼합용매로 컬럼크로마토그래피를 실시하여 중간체(10) 14.5g을 얻었다.(수율 95%)17.6 g of intermediate (9), 15.6 g of potassium hydroxide, 200 ml of tetrahydrofuran, 200 ml of ethanol and 200 ml of water were placed in a 1 L round bottom three necked flask and stirred under reflux for 8 hours. After cooling, the reaction solution is separated into water and dichloromethane, and the dichloromethane layer is concentrated. Column chromatography was performed with a mixed solvent of dichloromethane and n-hexane to obtain 14.5 g of intermediate (10) (yield: 95%).
MS (ESI) : [M+H]+ 278MS (ESI): [M + H] < + > 278
제조예Manufacturing example 11: 중간체(11) 2-(1- 11: Intermediate (11) 2- (1- 브로모디벤조티오펜Bromodibenzothiophene -4-일)-4,4,5,5-Yl) -4,4,5,5- 테트라메틸Tetramethyl -1,3,2-디옥사보로란의 합성Synthesis of -1,3,2-dioxaborolane
250mL 둥근 바닥 3구 플라스크에 중간체(10) 14.5g, 비스(피나콜라토)디보론 15.9g, 아세토니트릴 150ml를 넣고 0℃에서 부틸니트라이트 8.1g을 서서히 적가한다. 적가 종료 후 0℃에서 30분 교반한 다음 80℃로 올려 2시간 교반한다. 반응액을 농축 후 에틸아세테이트와 n-헥산 혼합용매로 컬럼크로마토그래피를 실시하여 중간체(11) 10.3g을 얻었다.(수율 53%)14.5 g of the intermediate (10), 15.9 g of bis (pinacolato) diboron and 150 ml of acetonitrile are placed in a 250-mL round bottom three-necked flask, and 8.1 g of butyl nitrite is slowly added dropwise at 0 ° C. After completion of dropwise addition, the mixture was stirred at 0 ° C for 30 minutes, then heated to 80 ° C and stirred for 2 hours. The reaction mixture was concentrated and then subjected to column chromatography using a mixed solvent of ethyl acetate and n-hexane to obtain 10.3 g of intermediate (11) (yield: 53%).
MS (ESI) : [M+H]+ 373MS (ESI): [M + H] < + > 373
제조예 12: 중간체(12) 1-브로모-4-페닐디벤조티오펜의 합성Preparation Example 12: Intermediate (12) Synthesis of 1-bromo-4-phenyldibenzothiophene
질소 분위기 하에서 250ml 둥근바닥 3구 플라스크에 중간체(12) 3.2g, 아이오도벤젠 3.5g, 탄산 칼륨 3.4g, 테트라키스트리페닐포스핀팔라듐(0) 0.3g, 테트라하이드로퓨란 90ml 및 물 30ml를 넣고 24시간 동안 환류시켜 주었다. 반응액을 냉각한 후 디클로로메탄과 물로 추출하고, 추출된 용액을 농축하였다. n-헥산으로 컬럼크로마토그래피를 실시한 용액을 농축하여 중간체(12) 2.1g을 얻었다. (수율 71%)Under a nitrogen atmosphere, 3.2 g of intermediate (12), 3.5 g of iodobenzene, 3.4 g of potassium carbonate, 0.3 g of tetrakistriphenylphosphine palladium (0), 90 ml of tetrahydrofuran and 30 ml of water were placed in a 250 ml three- And refluxed for 24 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The solution was subjected to column chromatography with n-hexane and then concentrated to obtain 2.1 g of intermediate (12). (Yield: 71%)
MS (ESI) : [M+H]+ 339MS (ESI): [M + H] < + > 339
실시예 1: 화합물(1)의 합성Example 1: Synthesis of Compound (1)
질소 분위기 하에서 100ml 둥근바닥 3구 플라스크에 중간체(5) 1.3g, (4-(디([1,1'-비페닐]-4-일)아미노)페닐)보론산 1.8g, 탄산 칼륨 1.6g, 테트라키스트리페닐포스핀팔라듐(0) 0.1g, 테트라하이드로퓨란 36ml 및 물 12ml를 넣고 12시간 동안 환류시켜 주었다. 반응액을 냉각한 후 디클로로메탄과 물로 추출하고, 추출된 용액을 농축하였다. 디클로로메탄과 n-헥산 혼합용매로 컬럼크로마토그래피를 실시한 용액을 농축하여 화합물(1) 2.2g을 얻었다. (수율 86%)1.3 g of Intermediate (5), 1.8 g of (4- (di ([1,1'-biphenyl] -4-yl) amino) phenylboronic acid and 1.6 g of potassium carbonate in a 100 ml round bottom three- , 0.1 g of tetrakistriphenylphosphine palladium (0), 36 ml of tetrahydrofuran and 12 ml of water, and the mixture was refluxed for 12 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The resulting solution was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane, and then concentrated to obtain 2.2 g of the compound (1). (Yield: 86%)
MS (ESI) : [M+H]+ 640MS (ESI): [M + H] < + > 640
1H NMR(600MHz, CDCl3): δ 7.95 (d, 2H), 7.77 (d, 1H), 7.65-7.55 (m, 14H), 7.45-7.42 (m, 6H), 7.38-7.32 (m, 9H), 7.22 (t, 1H) 1 H NMR (600MHz, CDCl 3 ): δ 7.95 (d, 2H), 7.77 (d, 1H), 7.65-7.55 (m, 14H), 7.45-7.42 (m, 6H), 7.38-7.32 (m, 9H ), 7.22 (t, 1 H)
실시예 2: 화합물(2)의 합성Example 2: Synthesis of compound (2)
질소 분위기 하에서 100ml 둥근바닥 3구 플라스크에 중간체(6) 1.3g, (4-(디([1,1'-비페닐]-4-일)아미노)페닐)보론산 1.4g, 탄산 칼륨 1.1g, 테트라키스트리페닐포스핀팔라듐(0) 0.1g, 테트라하이드로퓨란 30ml 및 물 10ml를 넣고 12시간 동안 환류시켜 주었다. 반응액을 냉각한 후 디클로로메탄과 물로 추출하고, 추출된 용액을 농축하였다. 디클로로메탄과 n-헥산 혼합용매로 컬럼크로마토그래피를 실시한 용액을 농축하여 화합물(2) 1.5g을 얻었다. (수율 71%)1.3 g of Intermediate (6), 1.4 g of (4- (di ([1,1'-biphenyl] -4-yl) amino) phenylboronic acid and 1.1 g of potassium carbonate in a 100 ml round bottom three- , 0.1 g of tetrakistriphenylphosphine palladium (0), 30 ml of tetrahydrofuran and 10 ml of water were added and the mixture was refluxed for 12 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The resulting solution was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane, and then concentrated to obtain 1.5 g of the compound (2). (Yield: 71%)
MS (ESI) : [M+H]+ 805MS (ESI): [M + H] < + > 805
1H NMR(600MHz, CDCl3): δ 8.70 (s, 1H), 8.26 (d, 1H), 8.12 (s, 1H), 8.06-8.02 (m, 2H), 7.95 (s, 1H), 7.71 (d, 2H) 7.65-7.58 (m, 10H), 7.55 (d, 4H), 7.52-7.42 (m, 8H), 7.39 (t, 1H), 7.35-7.31 (m, 5H), 7.28 (d, 4H) 1 H NMR (600MHz, CDCl 3 ): δ 8.70 (s, 1H), 8.26 (d, 1H), 8.12 (s, 1H), 8.06-8.02 (m, 2H), 7.95 (s, 1H), 7.71 ( (d, 2H), 7.65-7.58 (m, 10H), 7.55 (d, 4H), 7.52-7.42 (m, 8H), 7.39 )
실시예 3: 화합물(16)의 합성Example 3: Synthesis of compound (16)
질소 분위기 하에서 100ml 둥근바닥 3구 플라스크에 중간체(5) 1.3g, N-([1,1'-바이페닐]-4-일)-9,9-디메틸-N-(4-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)페닐)-9H-플루오렌-2-아민 2.7g, 탄산 칼륨 1.6g, 테트라키스트리페닐포스핀팔라듐(0) 0.1g 및 테트라하이드로퓨란 30ml, 물 10ml를 넣고 12시간 동안 환류시켜 주었다. 반응액을 냉각한 후 디클로로메탄과 물로 추출하고, 추출된 용액을 농축하였다. 디클로로메탄과 n-헥산 혼합용매로 컬럼크로마토그래피를 실시한 용액을 농축하여 화합물(16) 2.5g을 얻었다. (수율 89%)In a 100 ml round-bottomed three-necked flask under a nitrogen atmosphere, 1.3 g of Intermediate (5), 1.3 g of N - ([1,1'-biphenyl] -4,9-dimethyl- Phenyl) -9H-fluorene-2-amine (2.7 g), potassium carbonate (1.6 g), tetrakis (0), 30 ml of tetrahydrofuran and 10 ml of water, and the mixture was refluxed for 12 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The resulting solution was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane, and the resulting solution was concentrated to obtain 2.5 g of Compound (16). (Yield: 89%)
MS (ESI) : [M+H]+ 680MS (ESI): [M + H] < + > 680
1H NMR(600MHz, CDCl3): δ 7.95 (d, 2H), 7.77 (d, 1H), 7.65-7.54 (m, 12H), 7.45-7.33 (m, 15H), 7.20 (t, 1H), 1.51 (s, 6H) 1 H NMR (600 MHz, CDCl 3 ):? 7.95 (d, 2H), 7.77 (d, 1H), 7.65-7.54 (m, 12H), 7.45-7.33 1.51 (s, 6H)
실시예 4: 화합물(20)의 합성Example 4: Synthesis of Compound (20)
질소 분위기 하에서 100mL 둥근 바닥 3구 플라스크에 중간체(5) 1.3g, 디([1,1'-비페닐-4-일)아민 1.6g, 트리스(디벤질리딘아세톤)디팔라듐(0) 0.1g, 15% 트리스(t-부틸)포스핀 0.1g, t-부톡시 나트륨 0.8g, 톨루엔 25ml를 넣고, 100℃로 12시간 교반한다. 반응액을 냉각 후 실리카겔 여과, 농축한 다음 디클로로메탄과 n-헥산 혼합용매로 컬럼크로마토그래피 실시하여 화합물(20) 1.7g을 얻었다. (수율 75%)In a 100 mL round-bottomed three-necked flask, 1.3 g of Intermediate (5), 1.6 g of di [(1,1'-biphenyl-4-yl) amine and 0.1 g of tris (dibenzylidineacetone) dipalladium , 0.1 g of 15% tris (t-butyl) phosphine, 0.8 g of t-butoxysodium and 25 ml of toluene, and the mixture was stirred at 100 ° C for 12 hours. The reaction solution was cooled, filtered through silica gel, concentrated, and then subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane to obtain 1.7 g of compound (20). (Yield: 75%)
MS (ESI) : [M+H]+ 564MS (ESI): [M + H] < + > 564
1H NMR(600MHz, CDCl3): δ 7.95 (d, 2H), 7.61 (d, 1H), 7.58-7.54 (m, 7H), 7.51 (d, 4H), 7.45-7.41 (m, 6H), 7.36 (t, 1H), 7.30 (t, 2H), 7.25 (d, 4H), 7.20 (d, 1H), 7.06 (t, 1H) 1 H NMR (600MHz, CDCl 3 ): δ 7.95 (d, 2H), 7.61 (d, 1H), 7.58-7.54 (m, 7H), 7.51 (d, 4H), 7.45-7.41 (m, 6H), 2H), 7.25 (d, 4H), 7.20 (d, IH), 7.06 (t,
실시예 5: 화합물(22)의 합성Example 5: Synthesis of compound (22)
질소 분위기 하에서 100mL 둥근 바닥 3구 플라스크에 중간체(6) 1.5g, 디([1,1'-비페닐-4-일)아민 1.4g, 트리스(디벤질리딘아세톤)디팔라듐(0) 0.1g, 15% 트리스(t-부틸)포스핀 0.1g, t-부톡시 나트륨 0.8g, 톨루엔 25ml를 넣고, 100℃로 12시간 교반한다. 반응액을 냉각 후 실리카겔 여과, 농축한 다음 디클로로메탄과 n-헥산 혼합용매로 컬럼크로마토그래피 실시하여 화합물(22) 1.8g을 얻었다. (수율 82%)1.5 g of Intermediate (6), 1.4 g of di [(1,1'-biphenyl-4-yl) amine and 0.1 g of tris (dibenzylidineacetone) dipalladium (0) in a 100 mL round bottom three- , 0.1 g of 15% tris (t-butyl) phosphine, 0.8 g of t-butoxysodium and 25 ml of toluene, and the mixture was stirred at 100 ° C for 12 hours. The reaction solution was cooled, filtered through silica gel, concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane to obtain 1.8 g of compound (22). (Yield: 82%)
MS (ESI) : [M+H]+ 729MS (ESI): [M + H] < + > 729
1H NMR(600MHz, CDCl3): δ 8.68 (s, 1H), 8.25 (d, 1H), 7.00 (d, 1H), 7.72 (d, 1H), 7.63-7.61 (m, 4H), 7.60-7.57 (m, 6H), 7.55-7.28 (m, 21H), 7.08 (t, 1H) 1 H NMR (600 MHz, CDCl 3 ):? 8.68 (s, IH), 8.25 (d, IH), 7.00 7.57 (m, 6H), 7.55-7.28 (m, 21H), 7.08 (t, 1H)
실시예 6: 화합물(31)의 합성Example 6: Synthesis of compound (31)
질소 분위기 하에서 100ml 둥근바닥 3구 플라스크에 중간체(7) 1.4g, 페닐보론산 0.3g, 탄산 칼륨 0.9g, 테트라키스트리페닐포스핀팔라듐(0) 0.1g, 테트라하이드로퓨란 30ml 및 물 10ml를 넣고 12시간 동안 환류시켜 주었다. 반응액을 냉각한 후 디클로로메탄과 물로 추출하고, 추출된 용액을 농축하였다. 디클로로메탄과 n-헥산 혼합용매로 컬럼크로마토그래피를 실시한 용액을 농축하여 화합물(31) 1.1g을 얻었다. (수율 82%)In a 100 ml round-bottomed three-necked flask under nitrogen, 1.4 g of intermediate (7), 0.3 g of phenylboronic acid, 0.9 g of potassium carbonate, 0.1 g of tetrakistriphenylphosphine palladium (0), 30 ml of tetrahydrofuran and 10 ml of water And refluxed for 12 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The solution was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane, and then the solution was concentrated to obtain 1.1 g of the compound (31). (Yield: 82%)
1H NMR(600MHz, CDCl3): δ 7.87 (dd, 2H), 7.77 (s, 1H), 7.61-7.59 (m, 5H), 7.53-7.49 (m, 8H), 7.47-7.39 (m, 7H), 7.32 (dd, 2H), 7.26 (d, 4H) 1 H NMR (600 MHz, CDCl 3 ):? 7.87 (dd, 2H), 7.77 (s, 1H), 7.61-7.59 (m, 5H), 7.53-7.49 (m, 8H), 7.47-7.39 ), 7.32 (dd, 2H), 7.26 (d, 4H)
MS (ESI) : [M+H]+ 640MS (ESI): [M + H] < + > 640
실시예 7: 화합물(42)의 합성Example 7: Synthesis of compound (42)
질소 분위기 하에서 100ml 둥근바닥 3구 플라스크에 중간체(12) 1.5g, (4-(디([1,1'-비페닐]-4-일)아미노)페닐)보론산 2.0g, 탄산 칼륨 1.8g, 테트라키스트리페닐포스핀팔라듐(0) 0.2g, 테트라하이드로퓨란 45ml 및 물 15ml를 넣고 12시간 동안 환류시켜 주었다. 반응액을 냉각한 후 디클로로메탄과 물로 추출하고, 추출된 용액을 농축하였다. 디클로로메탄과 n-헥산 혼합용매로 컬럼크로마토그래피를 실시한 용액을 농축하여 화합물(42) 2.4g을 얻었다. (수율 84%)1.5 g of the intermediate (12), 2.0 g of (4- (di ([1,1'-biphenyl] -4-yl) amino) phenyl) boronic acid and 1.8 g of potassium carbonate in a 100 ml round bottom three- , 0.2 g of tetrakistriphenylphosphine palladium (0), 45 ml of tetrahydrofuran and 15 ml of water, and the mixture was refluxed for 12 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The resulting solution was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane, and the resulting solution was concentrated to obtain 2.4 g of Compound (42). (Yield: 84%)
MS (ESI) : [M+H]+ 656MS (ESI): [M + H] < + > 656
1H NMR(600MHz, CDCl3): δ 7.92 (d, 2H), 7.75-7.51 (m, 15H), 7.48-7.39 (m, 6H), 7.39-7.22 (m, 10H) 1 H NMR (600 MHz, CDCl 3 ):? 7.92 (d, 2H), 7.75-7.51 (m, 15H), 7.48-7.39 (m, 6H), 7.39-7.22
소자실시예Device Example
1. 화합물 1을 2차 정공 1.
ITO (Indium tin oxide)가 100nm 두께로 박막 코팅된 유리 기판을 이소프로필 알코올 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송 시켜 산소 플라즈마를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다. The glass substrate coated with ITO (Indium Tin Oxide) thin film with a thickness of 100 nm was ultrasonically cleaned with isopropyl alcohol solvent, dried and transferred to a plasma cleaner, the substrate was cleaned using oxygen plasma for 5 minutes, and the substrate was vacuum- Respectively.
이와 같이 준비된 ITO 투명 전극을 양극으로 사용하여 ITO 기판 상에 화합물HIL 및 화합물 IL을 각각 50nm 및 5nm의 두께로 진공증착하여 정공 주입층을 형성하였다. 이어서 1차 정공 수송층으로서 화합물 HTL을 20nm 두께로 진공 증착하고, 1차 정공 수송층 상부에 2차 정공 수송층으로서 화합물 1을 20nm 두께로 형성하였다. 상기 2차 정공 수송층 상부에 1:1의 비율로 화합물 GH-1과 GH-2를 호스트로 사용하고 도판트로 화합물 GD를 10 부피%로 도핑하여 진공증착하여 발광층을 형성하였다.Compound HIL and compound IL were vacuum-deposited on the ITO substrate to a thickness of 50 nm and 5 nm, respectively, using the thus-prepared ITO transparent electrode as an anode to form a hole injection layer. Subsequently, Compound HTL as a first hole transporting layer was vacuum deposited to a thickness of 20 nm, and
그 후, 상기 발광층 상부에 전자수송층으로서 화합물 ETL을 30nm 두께로 형성하였다. 상기 전자수송층 상부에 Liq [lithium quinolate] 1.5nm와 Al 100nm를 순차적으로 진공 증착하여 음극을 형성함으로써 유기전계발광소자를 제조하였다.Thereafter, a compound ETL as an electron transporting layer was formed to a thickness of 30 nm on the light emitting layer. Liq [lithium quinolate] 1.5 nm and Al 100 nm were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby fabricating an organic electroluminescent device.
소자실시예Device Example 2. 화합물 2를 2차 정공 2. Compound 2 was dissolved in a second hole 수송층으로To the transport layer 포함하는 Included 유기전계발광소자Organic electroluminescent device 제조 Produce
화합물 1 대신에 화합물 2를 사용한 점을 제외하고는 소자실시예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was manufactured in the same manner as in the device example 1 except that the compound 2 was used instead of the
소자실시예Device Example 3. 화합물 16을 2차 정공 3. Compound 16 was reacted with a second hole 수송층으로To the transport layer 포함하는 Included 유기전계발광소자Organic electroluminescent device 제조 Produce
화합물 1 대신에 화합물 16을 사용한 점을 제외하고는 소자실시예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was manufactured in the same manner as in the device example 1 except that the compound 16 was used instead of the
소자실시예Device Example 4. 화합물 20을 2차 정공 4. Compound 20 was dissolved in a second hole 수송층으로To the transport layer 포함하는 Included 유기전계발광소자Organic electroluminescent device 제조 Produce
화합물 1 대신에 화합물 20을 사용한 점을 제외하고는 소자실시예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was manufactured in the same manner as in the device example 1 except that the compound 20 was used instead of the
소자실시예Device Example 5. 화합물 22를 2차 정공 5. Compound 22 was dissolved in a second hole 수송층으로To the transport layer 포함하는 Included 유기전계발광소자Organic electroluminescent device 제조 Produce
화합물 1 대신에 화합물 22를 사용한 점을 제외하고는 소자실시예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was prepared in the same manner as in the device example 1, except that the compound 22 was used instead of the
소자실시예Device Example 6. 화합물 31을 2차 정공 6. Compound 31 was reacted with a second hole 수송층으로To the transport layer 포함하는 Included 유기전계발광소자Organic electroluminescent device 제조 Produce
화합물 1 대신에 화합물 31을 사용한 점을 제외하고는 소자실시예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was prepared in the same manner as in Example 1 except that the compound 31 was used instead of the
소자실시예Device Example 7. 화합물 42를 2차 정공 7. Compound 42 was coupled to a second hole 수송층으로To the transport layer 포함하는 Included 유기전계발광소자Organic electroluminescent device 제조 Produce
화합물 1 대신에 화합물 42를 사용한 점을 제외하고는 소자실시예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was manufactured in the same manner as in the device example 1 except that the compound 42 was used instead of the
소자비교예 1. NPB를 2차 정공 수송층으로 포함하는 유기전계발광소자 제조Comparative Example 1. Fabrication of organic electroluminescent device including NPB as a second hole transport layer
화합물 1 대신에 NPB를 사용한 점을 제외하고는 소자실시예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was prepared in the same manner as in Example 1 except that NPB was used instead of
상기 소자실시예 및 소자비교예에서 사용한 화합물 HIL, IL, HTL, NPB, GH-1, GH-2, GD 및 ETL의 구조식은 아래와 같다.The structural formulas of the compounds HIL, IL, HTL, NPB, GH-1, GH-2, GD and ETL used in the device examples and device comparative examples are as follows.
유기전계발광소자의 특성 분석Characterization of organic electroluminescent device
이하, 소자실시예 1 내지 7 및 소자비교예 1에 따라 제조된 유기전계발광소자를 전류밀도 10 mA/cm2 기준의 발광효율과 초기 휘도 4500cd/m2의 정전류로 구동시켜휘도가 3% 감소되는 수명 시간의 결과를 하기 표1에 나타내었다.Hereinafter, the elements of Examples 1 to 7 and the element compared to driving with a constant current intensity is 3% reduction in Example 1, the organic light emitting device produced a current density according to 10 mA / cm 2 based on the luminous efficiency of the initial luminance of 4500cd / m 2 The results of the life time are shown in Table 1 below.
(cd/A)Luminance efficiency
(cd / A)
(hr)Life time
(hr)
표 1에 따르면, 본 발명에 의한 화합물 1, 2, 16, 20, 22, 31 및 42를 정공수송층으로 유기전계발광소자에 사용한 결과, 모두가 종래의 물질인 NPB 대비 우수한 휘도 효율과 수명 특성을 보이는 것을 확인할 수 있었다.As shown in Table 1, when compounds 1, 2, 16, 20, 22, 31 and 42 according to the present invention were used as a hole transport layer in an organic electroluminescent device, all exhibited excellent luminance efficiency and lifetime characteristics I could see what was visible.
Claims (10)
[구조식 1]
구조식 1에서,
R1 내지 R6은 서로 같거나 다르고, R1 내지 R6은 각각 독립적으로 수소원자, 중수소원자, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이고,
L은 원자가결합, 치환 또는 비치환된 C1 내지 C30 알킬렌기, 치환 또는 비치환된 C3 내지 C30 시클로알킬렌기, 치환 또는 비치환된 C2 내지 C30 헤테로시클로알킬렌기, 치환 또는 비치환된 C6 내지 C30 아릴렌기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로아릴렌기이고,
X는 산소원자 또는 황원자이고,
Ar1 내지 Ar3은 서로 같거나 다르고, Ar1 내지 Ar3은 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이다.A compound for an organic electroluminescence device represented by Structural Formula (1) below.
[Structural formula 1]
In formula 1,
R 1 to R 6 are the same as or different from each other and each of R 1 to R 6 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
L is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C2 to C30 heterocycloalkylene group, a substituted or unsubstituted C6 to C30 aryl Or a substituted or unsubstituted C2 to C30 heteroarylene group,
X is an oxygen atom or a sulfur atom,
Ar 1 to Ar 3 are the same or different from each other, and Ar 1 to Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group.
상기 구조식 1로 표시되는 화합물은 하기 구조식 2로 표시되는 화합물인 것을 특징으로 하는 유기전계발광소자용 화합물.
[구조식 2]
구조식 2에서,
R1 내지 R6은 서로 같거나 다르고, R1 내지 R6은 각각 독립적으로 수소원자, 중수소원자, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이고,
L은 원자가결합, 치환 또는 비치환된 C1 내지 C30 알킬렌기, 치환 또는 비치환된 C3 내지 C30 시클로알킬렌기, 치환 또는 비치환된 C2 내지 C30 헤테로시클로알킬렌기, 치환 또는 비치환된 C6 내지 C30 아릴렌기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로아릴렌기이고,
X는 산소원자 또는 황원자이고,
Ar1 내지 Ar3은 서로 같거나 다르고, Ar1 내지 Ar3은 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이다.The method according to claim 1,
Wherein the compound represented by the structural formula (1) is a compound represented by the following structural formula (2).
[Structural formula 2]
In formula 2,
R 1 to R 6 are the same as or different from each other and each of R 1 to R 6 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
L is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C2 to C30 heterocycloalkylene group, a substituted or unsubstituted C6 to C30 aryl Or a substituted or unsubstituted C2 to C30 heteroarylene group,
X is an oxygen atom or a sulfur atom,
Ar 1 to Ar 3 are the same or different from each other, and Ar 1 to Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group.
상기 구조식 1로 표시되는 화합물은 하기 구조식 3으로 표시되는 화합물인 것을 특징으로 하는 유기전계발광소자용 화합물.
[구조식 3]
구조식 3에서,
R1 내지 R6은 서로 같거나 다르고, R1 내지 R6은 각각 독립적으로 수소원자, 중수소원자, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이고,
L은 원자가결합, 치환 또는 비치환된 C1 내지 C30 알킬렌기, 치환 또는 비치환된 C3 내지 C30 시클로알킬렌기, 치환 또는 비치환된 C2 내지 C30 헤테로시클로알킬렌기, 치환 또는 비치환된 C6 내지 C30 아릴렌기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로아릴렌기이고,
X는 산소원자 또는 황원자이고,
Ar1 내지 Ar3은 서로 같거나 다르고, Ar1 내지 Ar3은 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기인 것을 특징으로 하는 유기전계발광소자용 화합물.The method according to claim 1,
Wherein the compound represented by the structural formula (1) is a compound represented by the following structural formula (3).
[Structural Formula 3]
In Structure 3,
R 1 to R 6 are the same as or different from each other and each of R 1 to R 6 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
L is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C2 to C30 heterocycloalkylene group, a substituted or unsubstituted C6 to C30 aryl Or a substituted or unsubstituted C2 to C30 heteroarylene group,
X is an oxygen atom or a sulfur atom,
Ar 1 to Ar 3 are the same or different from each other and each of Ar 1 to Ar 3 is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group. Compound for device.
Ar1 내지 Ar3은 서로 같거나 다르고, Ar1 내지 Ar3은 각각 독립적으로
R7 내지 R38은 서로 같거나 다르고, R7 내지 R38은 각각 독립적으로 수소원자, 중수소원자, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기인 것을 특징으로 하는 유기전계발광소자용 화합물.3. The method according to claim 2 or 3,
Ar 1 to Ar 3 are the same or different from each other, Ar 1 to Ar 3 are each independently
R 7 to R 38 are the same or different from each other and each of R 7 to R 38 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
상기 유기전계발광소자용 화합물은 하기 화학식으로 표시되는 화합물 1 내지 62 중에서 선택된 어느 하나인 것을 특징으로 하는 유기전계발광소자용 화합물.
Wherein the organic electroluminescent device compound is any one selected from compounds 1 to 62 represented by the following formulas.
상기 단수 또는 복수의 유기물층 중에서 선택된 1종 이상의 유기물층은 제1항에 따른 유기전계발광소자용 화합물을 포함하는 것을 특징으로 하는 유기전계발광소자.1. An organic electroluminescent device comprising a first electrode, a second electrode, and a single or a plurality of organic layers between the first electrode and the second electrode,
The organic electroluminescent device according to claim 1, wherein the at least one organic layer selected from the group consisting of the single or plural organic layers includes the compound for an organic electroluminescent device according to claim 1.
상기 단수 또는 복수의 유기물층은 발광층을 포함하는 것을 특징으로 하는 유기전계발광소자.8. The method of claim 7,
Wherein the single or plural organic layers include a light emitting layer.
상기 복수의 유기물층은 발광층을 포함하고, 상기 복수의 유기물층은 전자주입층, 전자수송층, 정공차단층, 전자차단층, 정공수송층 및 정공주입층 중에서 선택된 1종 이상을 추가로 포함하는 것을 특징으로 하는 유기전계발광소자.8. The method of claim 7,
Wherein the plurality of organic layers include a light emitting layer and the plurality of organic layers further include at least one selected from an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, a hole transporting layer and a hole injecting layer Organic electroluminescent device.
상기 발광층은 호스트와 도펀트를 포함하는 것을 특징으로 하는 유기전계발광소자.
9. The method of claim 8,
Wherein the light emitting layer comprises a host and a dopant.
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| CN110669040A (en) * | 2019-09-26 | 2020-01-10 | 上海天马有机发光显示技术有限公司 | Compound, display panel and display device |
| CN111732578A (en) * | 2020-08-07 | 2020-10-02 | 南京高光半导体材料有限公司 | Organic electroluminescent compound and organic electroluminescent device |
| WO2020241826A1 (en) * | 2019-05-31 | 2020-12-03 | 出光興産株式会社 | Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device |
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