CN106467549B - A kind of compound containing benzimidazole and its application on organic electroluminescence device - Google Patents
A kind of compound containing benzimidazole and its application on organic electroluminescence device Download PDFInfo
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- CN106467549B CN106467549B CN201610630297.9A CN201610630297A CN106467549B CN 106467549 B CN106467549 B CN 106467549B CN 201610630297 A CN201610630297 A CN 201610630297A CN 106467549 B CN106467549 B CN 106467549B
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- benzimidazole
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 59
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000005401 electroluminescence Methods 0.000 title abstract description 5
- 239000000463 material Substances 0.000 claims abstract description 53
- -1 benzimidazoles compound Chemical class 0.000 claims abstract description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 45
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 24
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 16
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 claims description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 15
- 239000012298 atmosphere Substances 0.000 claims description 15
- 239000000706 filtrate Substances 0.000 claims description 15
- 239000000741 silica gel Substances 0.000 claims description 15
- 229910002027 silica gel Inorganic materials 0.000 claims description 15
- 229960001866 silicon dioxide Drugs 0.000 claims description 15
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 14
- 238000001914 filtration Methods 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 7
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 235000019441 ethanol Nutrition 0.000 claims description 5
- NVUJWPQINQUNNM-UHFFFAOYSA-N 1h-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1.C1=CC=C2NC=NC2=C1 NVUJWPQINQUNNM-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 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 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 152
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 63
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 230000005540 biological transmission Effects 0.000 description 17
- 238000002347 injection Methods 0.000 description 17
- 239000007924 injection Substances 0.000 description 17
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 16
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 16
- 230000027756 respiratory electron transport chain Effects 0.000 description 16
- 238000002156 mixing Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 4
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 4
- 150000003851 azoles Chemical class 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125773 compound 10 Drugs 0.000 description 3
- 229940125758 compound 15 Drugs 0.000 description 3
- 229940126086 compound 21 Drugs 0.000 description 3
- 229940126540 compound 41 Drugs 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 2
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 2
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 2
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 2
- KJUCEHPDQYFPPY-UHFFFAOYSA-N 3-phenyl-2,5-dihydrobenzimidazole Chemical compound C1(=CC=CC=C1)N1CN=C2C1=CCC=C2 KJUCEHPDQYFPPY-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 229940125851 compound 27 Drugs 0.000 description 2
- 229940125878 compound 36 Drugs 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- JLFRMMLHHOZVRI-UHFFFAOYSA-N (3-phenylphenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC(C=2C=CC=CC=2)=C1 JLFRMMLHHOZVRI-UHFFFAOYSA-N 0.000 description 1
- AELBZZMQJAJEJW-UHFFFAOYSA-N 1-bromo-9-phenylcarbazole Chemical compound BrC1=CC=CC(C2=CC=CC=C22)=C1N2C1=CC=CC=C1 AELBZZMQJAJEJW-UHFFFAOYSA-N 0.000 description 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- HNACKJNPFWWEKI-UHFFFAOYSA-N 3,6-dimethyl-9h-carbazole Chemical compound C1=C(C)C=C2C3=CC(C)=CC=C3NC2=C1 HNACKJNPFWWEKI-UHFFFAOYSA-N 0.000 description 1
- GDKWMINSMJKPRT-UHFFFAOYSA-N 3-n,3-n,6-n,6-n-tetraphenyl-9h-carbazole-3,6-diamine Chemical class C1=CC=CC=C1N(C=1C=C2C3=CC(=CC=C3NC2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 GDKWMINSMJKPRT-UHFFFAOYSA-N 0.000 description 1
- TYXSZNGDCCGIBO-UHFFFAOYSA-N 3-tert-butyl-9h-carbazole Chemical compound C1=CC=C2C3=CC(C(C)(C)C)=CC=C3NC2=C1 TYXSZNGDCCGIBO-UHFFFAOYSA-N 0.000 description 1
- WFQQOWDFMDPMQL-UHFFFAOYSA-N 5h-benzimidazole Chemical compound C1C=CC2=NC=NC2=C1 WFQQOWDFMDPMQL-UHFFFAOYSA-N 0.000 description 1
- CVGQJSXRWNPYNE-UHFFFAOYSA-N 6-N-benzo[a]anthracen-1-yl-9H-carbazole-3,6-diamine Chemical class C1(=CC=CC2=CC=C3C=C4C=CC=CC4=CC3=C12)NC=1C=C2C=3C=C(C=CC=3NC2=CC=1)N CVGQJSXRWNPYNE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HJCUTNIGJHJGCF-UHFFFAOYSA-N acridan acid Natural products C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940035422 diphenylamine Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000003752 improving hair Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
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- 238000011056 performance test Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
A kind of application the invention discloses benzimidazoles compound and its on organic electroluminescence device, the compound is using benzimidazole and ring is core, has the characteristics that intermolecular be not easy to crystallize, be not easy to assemble, with good filming.The compounds of this invention as OLED luminescent device luminescent layer material of main part in use, device current efficiency, power efficiency and external quantum efficiency are greatly improved；Meanwhile device lifetime is promoted clearly.
Description
Technical field
The present invention relates to technical field of semiconductors, more particularly, to a kind of containing the compound of benzimidazole and its work
The application for being emitting layer material on Organic Light Emitting Diode.
Background technique
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology can both be used to make
New display product is made, production novel illumination product is can be used for, is expected to substitute existing liquid crystal display and fluorescent lighting,
Application prospect is very extensive.
Structure of the OLED luminescent device like sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it
Between organic functional material, various different function materials are overlapped mutually depending on the application collectively constitutes OLED luminescent device together.
As current device, when the two end electrodes application voltage to OLED luminescent device, and pass through electric field action organic layer functional material
Positive and negative charge in film layer, positive and negative charge is further compound in luminescent layer, i.e. generation OLED electroluminescent.
The organic electroluminescence device of excellent combination property in order to obtain needs to design suitable Subjective and Objective material and optimization
Device architecture, luminescent layer material of main part generally comprise hole and/or electron-transport unit, have suitable carrier transport
Can, and its triplet energy level is required to be higher than illuminator, it just can guarantee that triplet exciton is confined to luminescent layer in this way.In addition, being
Realization carrier is efficiently injected to drop low start voltage, and material of main part should also have relative to the suitable of neighbouring organic layer
Energy level.
In recent years, bipolar host material is led because having the hole of balance and electronic carrier stream in electroluminescent device
Domain is attract attention, and the production that gradually moves towards the industrialization.
For current OLED shows the actual demand of Lighting Industry, the development of OLED material is also far from enough at present, falls
Afterwards in the requirement of panel manufacturing enterprise, the organic functional material as material enterprise development higher performance is particularly important.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, the applicant provide a kind of compound containing benzimidazole and its
Application on organic electroluminescence device.The compounds of this invention is using benzimidazole and ring is core, as luminous layer main body material
Material is applied to Organic Light Emitting Diode, and the device that the present invention makes has good photoelectric properties, can satisfy panel manufacture enterprise
The requirement of industry.
Technical scheme is as follows:
The applicant provides a kind of using benzimidazole and ring is the compound of core, the compound structure such as general formula (1)
It is shown:
In general formula (1), X indicate oxygen atom, sulphur atom or
Ar1、Ar2、Ar3Expression independentlyOr-R；
Wherein, Ar indicates phenyl, C1-10Phenyl, the dibiphenylyl, terphenyl, naphthalene of linear or branched alkyl group substitution；
N takes 1 or 2；
Structure shown in R selection hydrogen atom, general formula (2) or general formula (3), and Ar1、Ar2、Ar3In R at least one selection
Structure shown in general formula (2) or general formula (3):
Wherein, Ar4Indicate phenyl, C1-10Phenyl, dibiphenylyl, terphenyl or the naphthalene that linear or branched alkyl group replaces
Base；
R1、R2、R3Alkyl, phenyl, the C that selection carbon atom independently is 1-101-10What linear or branched alkyl group replaced
Structure shown in phenyl, dibiphenylyl, terphenyl, naphthalene, general formula (4), general formula (5), general formula (6) or general formula (7)；And R2、R3No
Simultaneously it is hydrogen:
Wherein, Ar5、Ar6、Ar7Expression phenyl, C independently1-10Phenyl, the biphenyl of linear or branched alkyl group substitution
Base, terphenyl, naphthalene, C1-10Benzofuranyl, the C of linear or branched alkyl group substitution1-10The benzene that linear or branched alkyl group replaces
Bithiophene base, C1-10The fluorenyl or C that linear or branched alkyl group replaces1-10The carbazyl that linear or branched alkyl group replaces；
X1It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Alkylidene, the aryl of linear or branched alkyl group substitution replace
One of the tertiary amine groups that alkylidene, alkyl or aryl replace.
Preferably, the R3When being expressed as structure shown in general formula (4), general formula (6) or general formula (7), R2It is also denoted as hydrogen
Atom.
Preferably, the R are as follows:
Any one of.
Preferably, the concrete structure formula of the compound are as follows:
Any one of.
The applicant additionally provides a kind of luminescent device comprising the compound, master of the compound as luminescent layer
Body material, for making OLED device.
The applicant additionally provides a kind of method for preparing the compound, the reaction equation in preparation process are as follows:
N in reaction equation 1~3, m independently be expressed as 0 or 1；
Wherein reaction equation 1 the preparation method comprises the following steps:
Weigh bromo-derivative, the Ar of benzimidazole and ring1-H、Ar2- H is dissolved with toluene；Add Pd2(dba)3, three tertiary fourths
Base phosphine, sodium tert-butoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in 95~110 DEG C of reaction temperature, reaction 10~
24 hours, cooling and filtering reacting solution, filtrate revolving crossed silicagel column, obtains target product；The bromine of the benzimidazole and ring
For object and Ar1-H、Ar2The molar ratio of-H is 1:0.8~2.0:0.8~2.0, Pd2(dba)3Molar ratio with bromo-derivative is
The molar ratio of 0.006~0.02:1, tri-tert-butylphosphine and bromo-derivative is 0.006~0.02:1, and sodium tert-butoxide and bromo-derivative rub
You are than being 1.0~3.0:1；
Reaction equation 2 the preparation method comprises the following steps:
Weigh benzimidazole benzimidazole and Ar3- Br is dissolved with toluene；Add Pd2(dba)3, tri-tert-butylphosphine, uncle
Sodium butoxide；Under an inert atmosphere, it by the mixed solution of above-mentioned reactant in 95~110 DEG C of reaction temperature, reacts 10~24 hours,
Cooling and filtering reacting solution, filtrate revolving, crosses silicagel column, obtains target product；The benzimidazole benzimidazole and Ar3-
The molar ratio of Br is 0.8~2.0:1, Pd2(dba)3With Ar3The molar ratio of-Br be 0.006~0.02:1, tri-tert-butylphosphine with
Ar3The molar ratio of-Br is 0.006~0.02:1, sodium tert-butoxide and Ar3The molar ratio of-Br is 1.0~3.0:1；
Reaction equation 3 the preparation method comprises the following steps:
Weigh bromo-derivative, the Ar of benzimidazole and ring1-B(OH)2、Ar2-B(OH)2, the toluene ethyl alcohol for being 2:1 with volume ratio
Mixed solvent dissolution；Under an inert atmosphere, Na is added2CO3Aqueous solution, Pd (PPh3)4；By the mixed solution of above-mentioned reactant
It in 95~110 DEG C of reaction temperature, reacts 10~24 hours, cooling and filtering reacting solution, filtrate revolving is crossed silicagel column, obtained
Target product；The bromo compound and Ar1-B(OH)2、Ar2-B(OH)2Molar ratio be 1:1.0~2.0:1.0~2.0；
Na2CO3Molar ratio with bromo-derivative is 1.0~3.0:1；Pd(PPh3)4Molar ratio with bromo-derivative is 0.006~0.02:1.
The present invention is beneficial to be had the technical effect that
The compounds of this invention is using benzimidazole and ring is parent nucleus, reconnects aromatic heterocycle group, destroys molecular symmetry,
To destroy the crystallinity of molecule, intermolecular aggtegation is avoided, the compound structure intramolecular includes electron donor
The mobility of electrons and holes, drop low start voltage can be improved in the combination of (donor, D) and electron acceptor (acceptor, A),
Parent nucleus benzimidazole and ring triplet energy level with higher, are confined to compound triplet exciton in luminescent layer, improve hair
Light efficiency, the compounds of this invention are suitable as the use of luminescent layer material of main part.
Compound of the present invention can be used as emitting layer material and make applied to OLED luminescent device, as luminous layer main body
Material can obtain good device performance, and the current efficiency of device, power efficiency and external quantum efficiency are greatly improved；
Meanwhile device lifetime is promoted clearly.
Compound-material of the present invention has good application effect in OLED luminescent device, has good industry
Change prospect.
Detailed description of the invention
Fig. 1 is the device architecture schematic diagram using the compounds of this invention；
Wherein, 1 is transparent substrate layer, and 2 be ito anode layer, and 3 be hole injection layer, and 4 be hole transmission layer, and 5 be luminous
Layer, 6 be electron transfer layer, and 7 be electron injecting layer, and 8 be cathode reflection electrode layer.
Specific embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
The synthesis of 1 compound 1 of embodiment
The specific synthetic route of the compound is now provided:
The bromo- benzo of 0.01mol 9- [d] benzo [4,5] miaow is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Azoles [2,1-b] thiazole, 0.015molN, N, N', N'- tetraphenyl -9H- carbazole -3,6- diamines, 0.03mol sodium tert-butoxide, 1 ×
10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene are heated to reflux 24 hours, are sampled contact plate, have been reacted
Entirely, natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 99.26%, yield 46.32%.
HPLC-MS: material molecule amount 723.25 surveys molecular weight 723.43.
The synthesis of 2 compound 7 of embodiment
The specific synthetic route of the compound is now provided:
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, addition 0.01mol3- bromine 5- phenyl -5H- benzimidazole [1,
2-a] benzimidazole, 0.015mol (6- tert-butyl -9H- carbazole -3- base)-diphenyl-amine, 0.03mol sodium tert-butoxide, 1 × 10- 4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene are heated to reflux 24 hours, sampling contact plate, fully reacting,
Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 97.81%, yield 63.20%.
HPLC-MS: material molecule amount 671.30 surveys molecular weight 671.62.
The synthesis of 3 compound 10 of embodiment
The specific synthetic route of the compound is now provided:
The bromo- benzo of 0.01mol 3- [d] benzo [4,5] miaow is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Azoles [2,1-b] oxazole, 0.015mol 3- carbazole -6- phenyl -9H- carbazole, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2
(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene are heated to reflux 24 hours, sample contact plate, and fully reacting is naturally cold
But, it filters, filtrate revolving crosses silicagel column, obtains target product, purity 99.25, yield 73.00%.
HPLC-MS: material molecule amount 614.21 surveys molecular weight 614.59.
The synthesis of 4 compound 15 of embodiment
The specific synthetic route of the compound is now provided:
The preparation method of compound 15 is with embodiment 3, the difference is that the bromo- benzo of raw material 2- [d] benzo [4,5] imidazoles
[2,1-b] oxazole replaces the bromo- benzo of 3- [d] benzo [4,5] imidazoles [2,1-b] oxazole, and 9- phenyl -9H, 9'H- [3,3'] join click
Azoles replaces 3- carbazole -6- phenyl -9H- carbazole.
HPLC-MS: material molecule amount 614.21 surveys molecular weight 614.29.
The synthesis of 5 compound 21 of embodiment
The specific synthetic route of the compound is now provided:
The preparation method is the same as that of Example 1 for compound 21, the difference is that raw material 3, bis- phenoxazines of 6--carbazole replaces N, N,
N', N'- tetraphenyl -9H- carbazole -3,6- diamines.
HPLC-MS: material molecule amount 751.20 surveys molecular weight 751.36.
The synthesis of 6 compound 26 of embodiment
The specific synthetic route of the compound is now provided:
The bromo- benzo of 0.01mol9- [d] benzo [4,5] imidazoles is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 500ml
[2,1-b] thiazole, 0.015mol 4- [3,6- bis- (diphenyl amido) -9H- carbazole -9- base] boric acid, is dissolved with mixed solvent
(180ml toluene, 90ml ethyl alcohol), is then added 0.03molNa2CO30.0001mol Pd is then added in aqueous solution (2M)
(PPh3)4, it is heated to reflux 10-24 hours, samples contact plate, fully reacting.Natural cooling, filtering, filtrate revolving are crossed silicagel column, are obtained
To target product, HPLC purity 99.8%, yield 72.00%.
HPLC-MS: material molecule amount 799.28 surveys molecular weight 799.35.
The synthesis of 7 compound 27 of embodiment
The specific synthetic route of the compound is now provided:
Bromo- 1, the 3- bis- (3,6- dimethyl) of 0.01mol 5- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Carbazyl-benzene, 0.015mol 3- phenyl -5H- benzimidazole [1,2-a] benzimidazole, 0.03mol sodium tert-butoxide, 1 × 10-
4mol Pd2(dba)3, 1 × 10-4mol tri-tert-butylphosphine, 150ml toluene is heated to reflux 24 hours, samples contact plate, has reacted
Entirely, natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 98.20, yield 61.00%.
HPLC-MS: material molecule amount 745.32 surveys molecular weight 745.39.
The synthesis of 8 compound 36 of embodiment
The specific synthetic route of the compound is now provided:
The bromo- benzo of 0.01mo 8- [d] benzo [4,5] imidazoles is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 500ml
[2,1-b] thiazole, 0.015mol 9- biphenyl -3- base -6- tert-butyl -9H- carbazole -3- boric acid dissolve (180ml with mixed solvent
Toluene, 90ml ethyl alcohol), 0.03molNa is then added2CO30.0001mol Pd (PPh is then added in aqueous solution (2M)3)4, add
Heat reflux 10-24 hours, samples contact plate, fully reacting.Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target production
Object, HPLC purity 99.12%, yield 59.00%.
HPLC-MS: material molecule amount 597.22 surveys molecular weight 597.33.
The synthesis of 9 compound 41 of embodiment
The specific synthetic route of the compound is now provided:
The preparation method of compound 41 is with embodiment 7, the difference is that raw material 10- (the bromo- 9- phenyl -9H- carbazole-of 6-
3- yl) -9,9- dimethyl -9,10- dihydro-acridine replacement bromo- 1,3- bis- (3,6- dimethyl) carbazyl-benzene of 5-, raw material 5H- benzene
And imidazoles [1,2-a] benzimidazole replaces 3- phenyl -5H- benzimidazole [1,2-a] benzimidazole.
HPLC-MS: material molecule amount 655.27 surveys molecular weight 655.65.
The synthesis of 10 compound 44 of embodiment
The specific synthetic route of the compound is now provided:
The four-hole bottle of 500ml, under the atmosphere for being passed through nitrogen, addition 0.01mol 2,8- bis- bromo- benzo [d] benzo [4,
5] imidazoles [2,1-b] oxazole, 0.015mol 3,6- dimethyl -9H- carbazole, 0.015mol 10- (9H- carbazole -3- base) -9,9-
Dimethyl -9,10- acridan, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert
Phosphine, 250ml toluene are heated to reflux 24 hours, sample contact plate, fully reacting, and natural cooling filters, and filtrate revolving crosses silica gel
Column obtains target product, purity 95.90, yield 28.00%.
HPLC-MS: material molecule amount 773.32 surveys molecular weight 773.49.
The synthesis of 11 compound 45 of embodiment
The specific synthetic route of the compound is now provided:
0.01mo 2,8- bis- bromo- benzo [d] benzo [4,5] is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 500ml
Imidazoles [2,1-b] thiazole, 0.015mol 3- phenyl phenyl boric acid, 0.015mol 10- [9- (4- phenyl boric acid) -9H- carbazole -3-
Base] -10H- azophenlyene, dissolves (180ml toluene, 90ml ethyl alcohol) with mixed solvent, 0.03mol Na is then added2CO3Aqueous solution
0.0001mol Pd (PPh is then added in (2M)3)4, it is heated to reflux 10-24 hours, samples contact plate, fully reacting.Natural cooling,
Filtering, filtrate revolving, crosses silicagel column, obtains target product, HPLC purity 98.90%, yield 31.00%.
HPLC-MS: material molecule amount 798.25 surveys molecular weight 798.36.
The synthesis of 12 compound 52 of embodiment
The specific synthetic route of the compound is now provided:
0.01mol 5H- benzimidazole [1,2-a] benzo miaow is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 500ml
Azoles,-two-dibenzofurans -4- base of 0.015mol (the bromo- 9- phenyl -9H- carbazole -3- base of 6-)-amine, 0.03mol sodium tert-butoxide, 1
×10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert-butylphosphine, 250ml toluene is heated to reflux 24 hours, samples contact plate, instead
Should completely, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity 99.10, yield 36.00%.
HPLC-MS: material molecule amount 795.88 surveys molecular weight 795.96.
The compounds of this invention can be used as emitting layer material use, to the compounds of this invention 10, compound 45 and existing material
Material CBP carries out the measurement of hot property, luminescent spectrum, T1 energy level and cyclic voltammetric stability, testing result such as 1 institute of table respectively
Show.
Table 1
| Compound | Td(℃) | λPL(nm) | Cyclic voltammetric stability | T1 energy level (eV) |
| Compound 10 | 396 | 386 | It is excellent | 3.1 |
| Compound 45 | 423 | 379 | It is excellent | 3.0 |
| Material C BP | 353 | 369 | Difference | 2.7 |
Note: thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in the TGA-50H heat of Japanese Shimadzu Corporation
It is measured on weight analysis instrument, nitrogen flow 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, opens up Pu Kang using Japan
The measurement of SR-3 spectroradiometer；Cyclic voltammetric stability be by cyclic voltammetry observe material redox characteristic come into
Row identification；Test condition: test sample is dissolved in the methylene chloride and acetonitrile mixed solvent that volume ratio is 2:1, concentration 1mg/mL, electricity
Solving liquid is the tetrabutyl ammonium tetrafluoroborate of 0.1M or the organic solution of hexafluorophosphate.Reference electrode is Ag/Ag+ electricity
Pole is titanium plate to electrode, and working electrode is ITO electrode, and cycle-index is 20 times.T1 is the phosphorescent emissions light for first testing compound
Spectrum, and be calculated by phosphorescent emissions peak and (test equipment: utilize the FLS980 fluorescence spectrum of Edinburgh Instruments
Instrument, the Optistat DN-V2 cryogenic assembly of Oxford Instruments).
By upper table data it is found that the compounds of this invention have preferable oxidation-reduction stability, higher thermal stability, compared with
High T1 energy level, is suitable as the material of main part of luminescent layer；Meanwhile the compounds of this invention contain electron donor (donor, D) with
Electron acceptor (acceptor, A) makes so that the OLED device electrons and holes using the compounds of this invention reach equilibrium state
It obtains device efficiency and the service life gets a promotion.
13-22 and comparative example 1~3 the compound conduct in the devices that the present invention will be described in detail synthesizes by the following examples
The application effect of luminescent layer material of main part.Embodiment 14-22 is compared with embodiment 13, the complete phase of the manufacture craft of the device
Together, and identical baseplate material and electrode material are used, the film thickness of electrode material is also consistent, except that device
Emitting layer material is changed in part.Embodiment 13-22 is compared with comparative example 1~3, the luminescent layer of device described in comparative example 1
Material is using existing common raw material, and the device emitting layer material of embodiment 13-22 is using the compounds of this invention.Respectively
The structure composition of embodiment obtained device is as shown in table 2.The performance test results of each device are as shown in table 3.
Embodiment 13
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 1 and GD-19 according to 100:5, thickness 30nm)/electron transfer layer 6 (TPBI,
Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/Al
Specific preparation process is as follows:
Transparent substrate layer 1 uses transparent material.Ito anode layer 2 (film thickness 150nm) is washed, i.e., is successively carried out
Ultraviolet-ozone washing is carried out after neutralizing treatment, pure water, drying again to remove the organic residue on the transparent surface ITO.
On having carried out the ito anode layer 2 after above-mentioned washing, using vacuum deposition apparatus, it is 10nm's that film thickness, which is deposited,
Molybdenum trioxide MoO3It is used as hole injection layer 3.And then the TAPC of 80nm thickness is deposited as hole transmission layer 4.
After above-mentioned hole mobile material vapor deposition, the luminescent layer 5 of OLED luminescent device is made, structure includes OLED hair
The used material compound 1 of photosphere 5 is used as material of main part, and for GD-19 as dopant material, dopant material doping ratio is 5% weight
Ratio is measured, luminescent layer film thickness is 30nm.
After above-mentioned luminescent layer 5, continuation vacuum evaporation electron transport layer materials are TPBI.The vacuum evaporation coating of the material
Thickness is 40nm, this layer is electron transfer layer 6.
On electron transfer layer 6, by vacuum deposition apparatus, lithium fluoride (LiF) layer that film thickness is 1nm is made, this layer is
Electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, aluminium (Al) layer that film thickness is 80nm is made, this layer is cathode
Reflection electrode layer 8 uses.
After completing OLED luminescent device as described above, anode and cathode is connected with well known driving circuit, is surveyed
The I-E characteristic of the luminous efficiency of metering device, luminescent spectrum and device.
Embodiment 14
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 7 and GD-19 according to 100:5, thickness 30nm)/electron transfer layer 6 (TPBI,
Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 15
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 10 and GD-19 according to 100:5, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 16
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 15 and GD-19 according to 100:5, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 17
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 21 and GD-19 according to 100:5, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 18
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 26 and GD-19 according to 100:5, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 19
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 27 and Ir (PPy) 3 according to 100:10, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 20
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 36 and Ir (PPy) 3 according to 100:10, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 21
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 41 and GD-PACTZ according to 100:5, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 22
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 44 and GD-PACTZ according to 100:5, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 23
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 45, GH-204 and Ir (PPy) 3 according to 70:30:10, thickness 30nm)/electricity
Sub- 6 (TPBI, thickness 40nm)/electron injecting layer of transport layer, 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 24
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 52, GH-204 and GD-PACTZ according to 70:30:5, thickness 30nm)/electronics
Transport layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Comparative example 1
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of CBP and GD-19 according to 100:5, thickness 30nm)/electron transfer layer 6 (TPBI, thickness
40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Comparative example 2
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of CBP and Ir (PPy) 3 according to 100:10, thickness 30nm)/electron transfer layer 6 (TPBI,
Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Comparative example 3
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of CBP and GD-PACTZ according to 100:5, thickness 30nm)/electron transfer layer 6 (TPBI,
Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
The test result of made OLED luminescent device is shown in Table 3.
Table 2
Table 3
Illustrate: for device detection performance using comparative example 1 as reference, 1 device performance indexes of comparative example is set as 1.0.Than
Current efficiency compared with example 1 is 6.5cd/A (@10mA/cm2)；CIE chromaticity coordinates is (0.32,0.61)；The LT95 service life under 5000 brightness
Decay to 3.8Hr.Life-span test system is owner of the present invention and the OLED device life test that Shanghai University is studied jointly
Instrument.
The result of table 3 can be seen that compound of the present invention can be applied and OLED photophore as luminescent layer material of main part
Part production, and compared with comparative example 1, either efficiency or service life obtain larger change than known OLED material, especially
It is the driving service life biggish promotion of acquisition of device.
From the point of view of above data application, the compounds of this invention has in OLED luminescent device good as emitting layer material
Application effect, have good industrialization prospect.
Although disclosing the present invention by embodiment and preferred embodiment, it should be appreciated that it is public that the present invention is not limited to institutes
The embodiment opened.On the contrary, it will be understood by those skilled in the art that it is intended to various modifications and similar arrangement.Therefore, institute
Attached the scope of the claims should be consistent with widest explanation to cover all such modifications and similar arrangement.
Claims (8)
1. a kind of using benzimidazole and ring is the compound of core, it is characterised in that shown in the compound structure such as general formula (1):
In general formula (1), X indicate oxygen atom, sulphur atom or
Ar1、Ar2、Ar3Expression independentlyOr-R；
Wherein, Ar indicates phenyl, C1-10Phenyl, the dibiphenylyl, terphenyl, naphthalene of linear or branched alkyl group substitution；
N takes 1 or 2；
Structure shown in R selection hydrogen atom, general formula (2) or general formula (3), and Ar1、Ar2、Ar3In R at least one choose general formula
(2) or structure shown in general formula (3):
Wherein, Ar4Indicate phenyl, C1-10Phenyl, dibiphenylyl, terphenyl or the naphthalene that linear or branched alkyl group replaces；
R1Structure shown in independent selection general formula (4) or general formula (7):
R2Structure shown in independent selection general formula (4), general formula (6) or general formula (7):
R3Structure shown in independent selection general formula (4), general formula (6) or general formula (7):
Wherein, Ar5、Ar6、Ar7Expression phenyl, C independently1-10Phenyl, the dibiphenylyl, three of linear or branched alkyl group substitution
Xenyl, naphthalene, C1-10Benzofuranyl, the C of linear or branched alkyl group substitution1-10The benzo thiophene that linear or branched alkyl group replaces
Pheno base, C1-10The fluorenyl or C that linear or branched alkyl group replaces1-10The carbazyl that linear or branched alkyl group replaces；
X1It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10The alkylene of alkylidene, aryl substitution that linear or branched alkyl group replaces
One of the tertiary amine groups that base, alkyl or aryl replace.
2. a kind of described in claim 1 using benzimidazole and ring is the compound of core, it is characterised in that the R3It is expressed as leading to
When structure shown in formula (4), general formula (6) or general formula (7), R2It is expressed as hydrogen atom.
3. compound according to claim 1, it is characterised in that the R are as follows:
Any one of.
4. compound according to claim 1, it is characterised in that the concrete structure formula of the compound are as follows:
Any one of.
5. compound according to claim 2, it is characterised in that the R are as follows:
Any one of.
6. compound according to claim 2, it is characterised in that the concrete structure formula of the compound are as follows:
Any one of.
7. a kind of luminescent device comprising any one of claim 1~6 compound, it is characterised in that the compound conduct
The material of main part of luminescent layer, for making OLED device.
8. a kind of method for preparing any one of claim 1~6 compound, it is characterised in that the reaction side in preparation process
Formula are as follows:
N in reaction equation 1~3, m independently be expressed as 0 or 1；
Wherein reaction equation 1 the preparation method comprises the following steps:
Weigh bromo-derivative, the Ar of benzimidazole and ring1-H、Ar2- H is dissolved with toluene；Add Pd2(dba)3, tri-tert-butylphosphine,
Sodium tert-butoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in 95~110 DEG C of reaction temperature, reaction 10~24 is small
When, cooling and filtering reacting solution, filtrate revolving crosses silicagel column, obtains target product；The bromo-derivative of the benzimidazole and ring
With Ar1-H、Ar2The molar ratio of-H is 1:0.8~2.0:0.8~2.0, Pd2(dba)3With the molar ratio of bromo-derivative be 0.006~
The molar ratio of 0.02:1, tri-tert-butylphosphine and bromo-derivative is 0.006~0.02:1, and the molar ratio of sodium tert-butoxide and bromo-derivative is
1.0~3.0:1；
Reaction equation 2 the preparation method comprises the following steps:
Weigh benzimidazole benzimidazole and Ar3- Br is dissolved with toluene；Add Pd2(dba)3, tri-tert-butylphosphine, the tert-butyl alcohol
Sodium；Under an inert atmosphere, it by the mixed solution of above-mentioned reactant in 95~110 DEG C of reaction temperature, reacts 10~24 hours, it is cooling
And filtering reacting solution, filtrate revolving cross silicagel column, obtain target product；The benzimidazole benzimidazole and Ar3- Br's
Molar ratio is 0.8~2.0:1, Pd2(dba)3With Ar3The molar ratio of-Br is 0.006~0.02:1, tri-tert-butylphosphine and Ar3-Br
Molar ratio be 0.006~0.02:1, sodium tert-butoxide and Ar3The molar ratio of-Br is 1.0~3.0:1；
Reaction equation 3 the preparation method comprises the following steps:
Weigh bromo-derivative, the Ar of benzimidazole and ring1-B(OH)2、Ar2-B(OH)2, mixed with the toluene ethyl alcohol that volume ratio is 2:1
Solvent dissolution；Under an inert atmosphere, Na is added2CO3Aqueous solution, Pd (PPh3)4；By the mixed solution of above-mentioned reactant in anti-
95~110 DEG C of temperature are answered, is reacted 10~24 hours, cooling and filtering reacting solution, filtrate revolving crosses silicagel column, obtains target
Product；The bromo compound and Ar1-B(OH)2、Ar2-B(OH)2Molar ratio be 1:1.0~2.0:1.0~2.0；Na2CO3
Molar ratio with bromo-derivative is 1.0~3.0:1；Pd(PPh3)4Molar ratio with bromo-derivative is 0.006~0.02:1.
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| US11158820B2 (en) * | 2017-03-29 | 2021-10-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102599414B1 (en) * | 2017-09-21 | 2023-11-08 | 솔루스첨단소재 주식회사 | Organic compounds and organic electro luminescence device comprising the same |
| CN109928965B (en) * | 2017-12-15 | 2024-09-10 | 北京鼎材科技有限公司 | Compound and application thereof in organic electroluminescent field |
| CN111801332A (en) * | 2018-03-09 | 2020-10-20 | 默克专利有限公司 | Compounds for electronic devices |
| EP3762387B1 (en) * | 2018-03-09 | 2023-07-12 | Merck Patent GmbH | Compounds for electronic devices |
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| CN108948007A (en) * | 2018-08-02 | 2018-12-07 | 瑞声科技（南京）有限公司 | A kind of alkyl-substituted compound and its application |
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| CN111362947A (en) * | 2018-12-26 | 2020-07-03 | 江苏三月光电科技有限公司 | Benzimidazole-containing organic compound and application thereof |
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