CN106467549A - 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
- Publication number
- CN106467549A CN106467549A CN201610630297.9A CN201610630297A CN106467549A CN 106467549 A CN106467549 A CN 106467549A CN 201610630297 A CN201610630297 A CN 201610630297A CN 106467549 A CN106467549 A CN 106467549A
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- China
- Prior art keywords
- formula
- compound
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- benzimidazole
- bromo
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 56
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 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 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 238000002156 mixing Methods 0.000 claims description 16
- 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
- 238000001816 cooling Methods 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 12
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 8
- 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 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 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 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 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
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 229910052711 selenium 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 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
- 239000011734 sodium Substances 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
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 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 18
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- 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
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000000523 sample Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 0 Ic(ccc(-[n]1c(C=CC(N(c2ccccc2)c2ccccc2)=CC2)c2c2c1ccc(C*(c1ccccc1)C1=CCCCC=C1)c2)c1)c1N(c(cccc1)c1S1)C1=I Chemical compound Ic(ccc(-[n]1c(C=CC(N(c2ccccc2)c2ccccc2)=CC2)c2c2c1ccc(C*(c1ccccc1)C1=CCCCC=C1)c2)c1)c1N(c(cccc1)c1S1)C1=I 0.000 description 6
- 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
- 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
- 125000005605 benzo group Chemical group 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
- 238000004519 manufacturing process Methods 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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 230000008859 change Effects 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
- 238000005516 engineering process Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000007738 vacuum evaporation 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
- 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
- KUBSCXXKQGDPPD-UHFFFAOYSA-N 3-bromo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 KUBSCXXKQGDPPD-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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-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 compound [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
- 230000009471 action Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 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
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 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
- 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
- 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
- 238000005286 illumination Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 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
- 238000005457 optimization Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012488 sample solution Substances 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
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
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
- C07D—HETEROCYCLIC COMPOUNDS
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Abstract
The invention discloses a kind of benzimidazoles compound and its application on organic electroluminescence device, with benzimidazole and ring is as core for this compound, have the characteristics that intermolecular be difficult crystallization, be difficult assemble, there is good filming.When the compounds of this invention uses as the luminescent layer material of main part of OLED luminescent device, the current efficiency of device, power efficiency and external quantum efficiency are all greatly improved；Lifted clearly simultaneously for device lifetime.
Description
Technical field
The present invention relates to technical field of semiconductors, especially relate to a kind of compound containing benzimidazole, and its work
For application on Organic Light Emitting Diode for the emitting layer material.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be used to make
Make new display product it is also possible to be used for making novel illumination product, be expected to substitute existing liquid crystal display and fluorescent lighting,
Application prospect is quite varied.
OLED luminescent device just as the structure of sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it
Between organic functional material, various difference in functionality materials are overlapped mutually according to purposes and collectively constitute OLED luminescent device together.
As current device, when the two end electrodes applied 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 compound in luminescent layer further, that is, produce OLED electroluminescent.
In order to obtain the organic electroluminescence device of excellent combination property, need to design suitable Subjective and Objective material and optimization
Device architecture, luminescent layer material of main part generally comprises hole and/or electric transmission unit, has suitable carrier transport
Can, and requiring its triplet energy level to be higher than luminous body, such guarantee triplet exciton is confined to luminescent layer.Additionally, being
Realize carrier efficiently injection to drop low start voltage, material of main part also should have suitable with respect to neighbouring organic layer
Energy level.
In recent years, bipolar host material, because having hole and the electronic carrier stream of balance, is led in electroluminescent device
Domain attract attention, and the production that progressively moving towards the industrialization.
For the actual demand that current OLED shows Lighting Industry, the development of current OLED material is also far from enough, falls
After the requirement of panel manufacturing enterprise, the organic functional material as material enterprise development higher performance is particularly important.
Content of the invention
For prior art exist the problems referred to above, the applicant provide a kind of compound containing benzimidazole and its
Application on organic electroluminescence device.With benzimidazole and ring is as core for the compounds of this invention, 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, disclosure satisfy that panel manufacture is looked forward to
The requirement of industry.
Technical scheme is as follows：
The applicant provide a kind of with benzimidazole and the compound as core for the ring, this compound structure such as formula (1)
Shown：
In formula (1), X represent oxygen atom, sulphur atom or
Ar1、Ar2、Ar3Expression independentlyOr-R；
Wherein, Ar represents phenyl, C1-10The phenyl of straight or branched alkyl replacement, dibiphenylyl, terphenyl, naphthyl；
N takes 1 or 2；
R chooses hydrogen atom, formula (2) or structure shown in formula (3), and Ar1、Ar2、Ar3In R at least selection
Formula (2) or structure shown in formula (3)：
Wherein, Ar4Represent phenyl, C1-10Phenyl, dibiphenylyl, terphenyl or naphthalene that straight or branched alkyl replaces
Base；
R1、R2、R3Carbon atom of choosing independently is the alkyl of 1-10, phenyl, C1-10Straight or branched alkyl replaces
Phenyl, dibiphenylyl, terphenyl, naphthyl, formula (4), formula (5), formula (6) or structure shown in formula (7)；And R2、R3No
It is hydrogen simultaneously：
Wherein, Ar5、Ar6、Ar7Expression phenyl independently, C1-10The phenyl of straight or branched alkyl replacement, biphenyl
Base, terphenyl, naphthyl, C1-10The benzofuranyl of straight or branched alkyl replacement, C1-10The benzene that straight or branched alkyl replaces
Bithiophene base, C1-10Fluorenyl or C that straight or branched alkyl replaces1-10The carbazyl that straight or branched alkyl replaces；
X1It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10The alkylidene that straight or branched alkyl replaces, aryl replace
One of tertiary amine groups that alkylidene, alkyl or aryl replace.
Preferably, described R3It is expressed as formula (4), formula (6) or shown in formula (7) during structure, R2It is also denoted as hydrogen
Atom.
Preferably, described R is：
In any one.
Preferably, the concrete structure formula of described compound is：
In any one.
The applicant additionally provides a kind of luminescent device comprising described compound, and described compound is as the master of luminescent layer
Body material, for making OLED.
The applicant additionally provides a kind of method preparing described compound, and the reaction equation in preparation process is：
N in reaction equation 1～3, m independently be expressed as 0 or 1；
The preparation method of wherein reaction equation 1 is：
Weigh benzimidazole the bromo-derivative of ring, Ar1-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 simultaneously filtering reacting solution, filtrate revolving, cross silicagel column, obtain target product；Described benzimidazole the bromine of ring
For thing and Ar1-H、Ar2The mol ratio of-H is 1:0.8～2.0:0.8～2.0, Pd2(dba)3Mol ratio with bromo-derivative is
0.006～0.02:1, tri-butyl phosphine is 0.006～0.02 with the mol ratio of bromo-derivative:1, sodium tert-butoxide is rubbed with bromo-derivative
That ratio is 1.0～3.0:1；
The preparation method of reaction equation 2 is：
Weigh benzimidazole benzimidazole and Ar3- Br, is dissolved with toluene；Add Pd2(dba)3, tri-butyl phosphine, uncle
Sodium butoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in 95～110 DEG C of reaction temperature, react 10～24 hours,
Cooling filtering reacting solution, filtrate revolving, cross silicagel column, obtain target product；Described benzimidazole benzimidazole and Ar3-
The mol ratio of Br is 0.8～2.0:1, Pd2(dba)3With Ar3The mol ratio of-Br is 0.006～0.02:1, tri-butyl phosphine with
Ar3The mol ratio of-Br is 0.006～0.02:1, sodium tert-butoxide and Ar3The mol ratio of-Br is 1.0～3.0:1；
The preparation method of reaction equation 3 is：
Weigh benzimidazole the bromo-derivative of ring, Ar1-B(OH)2、Ar2-B(OH)2, it is 2 with volume ratio:1 toluene ethanol
Mixed solvent dissolves；Under an inert atmosphere, add Na2CO3Aqueous solution, Pd (PPh3)4；Mixed solution by above-mentioned reactant
In 95～110 DEG C of reaction temperature, react 10～24 hours, cooling filtering reacting solution, filtrate revolving, cross silicagel column, obtain
Target product；Described bromo compound and Ar1-B(OH)2、Ar2-B(OH)2Mol ratio be 1:1.0～2.0:1.0～2.0；
Na2CO3Mol ratio with bromo-derivative is 1.0～3.0:1；Pd(PPh3)4Mol ratio with bromo-derivative is 0.006～0.02:1.
Beneficial the having technical effect that of the present invention：
With benzimidazole and ring is as parent nucleus for the compounds of this invention, reconnects aromatic heterocycle group, destroys molecular symmetry,
Thus the crystallinity of saboteur, it is to avoid intermolecular aggregation, described compound structure intramolecular comprises electron donor
The combination of (donor, D) and electron acceptor (acceptor, A) can improve the mobility in electronics and hole, fall low start voltage,
Parent nucleus benzimidazole ring has higher triplet energy level, makes compound triplet exciton be confined in luminescent layer, improves and sends out
Light efficiency, the compounds of this invention is suitable as luminescent layer material of main part and uses.
Compound of the present invention can be applied to OLED luminescent device as emitting layer material and make, as luminous layer main body
Material can obtain good device and show, the current efficiency of device, and power efficiency and external quantum efficiency are all greatly improved；
Lifted clearly simultaneously for device lifetime.
Compound-material of the present invention has good application effect in OLED luminescent device, has good industry
Change prospect.
Brief description
Fig. 1 is the device architecture schematic diagram using the compounds of this invention；
Wherein, 1 is transparent substrate layer, and 2 is ito anode layer, and 3 is hole injection layer, and 4 is hole transmission layer, and 5 is luminous
Layer, 6 is electron transfer layer, and 7 is electron injecting layer, and 8 is negative electrode reflection electrode layer.
Specific embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
The synthesis of embodiment 1 compound 1
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, adds 0.01mol 9- bromo- benzo [d] benzo [4,5] miaow
Azoles [2,1-b] thiazole, 0.015molN, N, N', N'- tetraphenyl -9H- carbazole -3,6- diamidogen, 0.03mol sodium tert-butoxide, 1 ×
10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reacted
Entirely, natural cooling, filters, filtrate revolving, crosses silicagel column, obtains target product, purity 99.26%, yield 46.32%.
HPLC-MS：Material molecule amount is 723.25, surveys molecular weight 723.43.
The synthesis of embodiment 2 compound 7
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, addition 0.01mol3- bromine 5- phenyl -5H- benzimidazole [1,
2-a] benzimidazole, 0.015mol (the 6- tert-butyl group -9H- carbazole -3- base)-diphenyl-amine, 0.03mol sodium tert-butoxide, 1 × 10- 4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reaction is complete,
Natural cooling, filters, filtrate revolving, crosses silicagel column, obtains target product, purity 97.81%, yield 63.20%.
HPLC-MS：Material molecule amount is 671.30, surveys molecular weight 671.62.
The synthesis of embodiment 3 compound 10
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, adds 0.01mol 3- bromo- benzo [d] benzo [4,5] miaow
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-butyl phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reaction is completely, naturally cold
But, filter, filtrate revolving, cross silicagel column, obtain target product, purity 99.25, yield 73.00%.
HPLC-MS：Material molecule amount is 614.21, surveys molecular weight 614.59.
The synthesis of embodiment 4 compound 15
The concrete synthetic route of this compound is now provided：
With embodiment 3, difference is raw material 2- bromo- benzo [d] benzo [4,5] imidazoles to the preparation method of compound 15
[2,1-b] oxazole replaces 3- bromo- benzo [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 is 614.21, surveys molecular weight 614.29.
The synthesis of embodiment 5 compound 21
The concrete synthetic route of this compound is now provided：
With embodiment 1, difference is raw material 3 to the preparation method of compound 21, and 6- bis- phenoxazines-carbazole replaces N, N,
N', N'- tetraphenyl -9H- carbazole -3,6- diamidogen.
HPLC-MS：Material molecule amount is 751.20, surveys molecular weight 751.36.
The synthesis of embodiment 6 compound 26
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 500ml, under the atmosphere being passed through nitrogen, adds 0.01mol9- bromo- benzo [d] benzo [4,5] imidazoles
[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 ethanol), is subsequently adding 0.03molNa2CO3Aqueous solution (2M), is subsequently adding 0.0001mol Pd
(PPh3)4, it is heated to reflux 10-24 hour, sample point plate, reaction is completely.Natural cooling, filters, filtrate revolving, crosses silicagel column, obtains
To target product, HPLC purity 99.8%, yield 72.00%.
HPLC-MS：Material molecule amount is 799.28, surveys molecular weight 799.35.
The synthesis of embodiment 7 compound 27
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, adds bromo- 1, the 3- of 0.01mol 5- bis- (3,6- dimethyl)
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-butyl phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reacted
Entirely, natural cooling, filters, filtrate revolving, crosses silicagel column, obtains target product, purity 98.20, yield 61.00%.
HPLC-MS：Material molecule amount is 745.32, surveys molecular weight 745.39.
The synthesis of embodiment 8 compound 36
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 500ml, under the atmosphere being passed through nitrogen, adds 0.01mo 8- bromo- benzo [d] benzo [4,5] imidazoles
[2,1-b] thiazole, the 0.015mol 9- biphenyl -3- base -6- tert-butyl group -9H- carbazole -3- boric acid, dissolves (180ml with mixed solvent
Toluene, 90ml ethanol), it is subsequently adding 0.03molNa2CO3Aqueous solution (2M), is subsequently adding 0.0001mol Pd (PPh3)4, plus
Hot reflux 10-24 hour, sample point plate, reaction is completely.Natural cooling, filters, filtrate revolving, crosses silicagel column, obtains target and produces
Thing, HPLC purity 99.12%, yield 59.00%.
HPLC-MS：Material molecule amount is 597.22, surveys molecular weight 597.33.
The synthesis of embodiment 9 compound 41
The concrete synthetic route of this compound is now provided：
The preparation method of compound 41 with embodiment 7, difference be raw material 10- (6- bromo- 9- phenyl -9H- carbazole -
3- yl) -9,9- dimethyl -9,10- dihydro-acridine replacement bromo- 1, the 3- of 5- bis- (3,6- dimethyl) carbazyl-benzene, raw material 5H- benzene
And imidazoles [1,2-a] benzimidazole replaces 3- phenyl -5H- benzimidazole [1,2-a] benzimidazole.
HPLC-MS：Material molecule amount is 655.27, surveys molecular weight 655.65.
The synthesis of embodiment 10 compound 44
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 500ml, under the atmosphere 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, it is heated to reflux 24 hours, sample point plate, reaction is complete, natural cooling, filters, filtrate revolving, cross silica gel
Post, obtains target product, purity 95.90, yield 28.00%.
HPLC-MS：Material molecule amount is 773.32, surveys molecular weight 773.49.
The synthesis of embodiment 11 compound 45
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 500ml, under the atmosphere being passed through nitrogen, adds 0.01mo 2,8- bis- bromo- benzo [d] benzo [4,5]
Imidazoles [2,1-b] thiazole, 0.015mol 3- phenyl phenylboric acid, 0.015mol 10- [9- (4- phenylboric acid) -9H- carbazole -3-
Base] -10H- azophenlyene, dissolves (180ml toluene, 90ml ethanol) with mixed solvent, is subsequently adding 0.03mol Na2CO3Aqueous solution
(2M), it is subsequently adding 0.0001mol Pd (PPh3)4, it is heated to reflux 10-24 hour, sample point plate, reaction is completely.Natural cooling,
Filter, filtrate revolving, cross silicagel column, obtain target product, HPLC purity 98.90%, yield 31.00%.
HPLC-MS：Material molecule amount is 798.25, surveys molecular weight 798.36.
The synthesis of embodiment 12 compound 52
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 500ml, under the atmosphere being passed through nitrogen, adds 0.01mol 5H- benzimidazole [1,2-a] benzo miaow
Azoles, 0.015mol (6- bromo- 9- phenyl -9H- carbazole -3- base)-two-dibenzofurans -4- base-amine, 0.03mol sodium tert-butoxide, 1
×10-4mol Pd2(dba)3, 1 × 10-4mol tri-butyl phosphine, 250ml toluene, it is heated to reflux 24 hours, sample point plate, instead
Should completely, natural cooling, filters, filtrate revolving, crosses silicagel column, obtain target product, purity 99.10, yield 36.00%.
HPLC-MS：Material molecule amount is 795.88, surveys molecular weight 795.96.
The compounds of this invention can use as emitting layer material, to the compounds of this invention 10, compound 45 and existing material
Material CBP carries out hot property, the mensure of luminescent spectrum, T1 energy level and cyclic voltammetric stability respectively, testing result such as table 1 institute
Show.
Table 1
| Compound | Td(℃) | λPL(nm) | Cyclic voltammetric stability | T1 energy level (eV) |
| Compound 10 | 396 | 386 | Excellent | 3.1 |
| Compound 45 | 423 | 379 | Excellent | 3.0 |
| Material C BP | 353 | 369 | Difference | 2.7 |
Note：Thermal weight loss temperature Td is in nitrogen atmosphere weightless 1% temperature, in the TGA-50H heat of Japanese Shimadzu Corporation
It is measured on weight analysis instrument, nitrogen flow is 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, open up Pu Kang using Japan
SR-3 spectroradiometer measures；Cyclic voltammetric stability is to be entered by the redox characteristic that cyclic voltammetry observes material
Row identification；Test condition：It is 2 that test sample is dissolved in volume ratio:1 dichloromethane and acetonitrile mixed solvent, concentration 1mg/mL, electricity
Solution 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 of first test compound
Spectrum, and (test equipment is calculated by phosphorescent emissions peak：FLS980 fluorescence spectrum using Edinburgh Instruments
Instrument, the Optistat DN-V2 cryogenic assembly of Oxford Instruments).
From upper table data, the compounds of this invention has a preferable oxidation-reduction stability, higher heat stability, relatively
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), so that the OLED electronics of application the compounds of this invention and hole reach poised state, makes
Obtain device efficiency and the life-span gets a promotion.
13-22 and comparative example 1～3 describe the compound conduct in the devices that the present invention synthesizes in detail by the following examples
The application effect of luminescent layer material of main part.Embodiment 14-22 compared with embodiment 13, the complete phase of processing technology of described device
With, and employed identical baseplate material and electrode material, the thickness of electrode material is also consistent, except that device
In part, emitting layer material there occurs change.Embodiment 13-22 compared with comparative example 1～3, the luminescent layer of device described in comparative example 1
Material uses existing conventional raw material, and the device emitting layer material of embodiment 13-22 uses 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
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
(compound 1 and GD-19 are according to 100 for 80nm)/luminescent layer 5：5 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI,
Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/Al
Concrete preparation process is as follows：
Transparent substrate layer 1 adopts transparent material.Ito anode layer 2 (thickness is 150nm) is washed, carries out successively
Neutralizing treatment, pure water, be dried after carry out again ultraviolet-ozone wash to remove the organic residue on transparent ITO surface.
On the ito anode layer 2 having carried out after above-mentioned washing, using vacuum deposition apparatus, being deposited with thickness is 10nm's
Molybdenum trioxide MoO3Use as hole injection layer 3.And then the TAPC of evaporation 80nm thickness is as hole transmission layer 4.
After above-mentioned hole mobile material evaporation terminates, make the luminescent layer 5 of OLED luminescent device, its structure includes OLED and sends out
As material of main part, as dopant material, dopant material doping ratio is 5% weight to GD-19 to the used material compound 1 of photosphere 5
Amount ratio, luminescent layer thickness is 30nm.
After above-mentioned luminescent layer 5, continuation vacuum evaporation electron transport layer materials are TPBI.The vacuum evaporation coating of this material
Thick is 40nm, and this layer is electron transfer layer 6.
On electron transfer layer 6, by vacuum deposition apparatus, make lithium fluoride (LiF) layer that thickness is 1nm, this layer is
Electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, make aluminum (Al) layer that thickness is 80nm, this layer is negative electrode
Reflection electrode layer 8 uses.
After OLED luminescent device accomplished as described above, with known drive circuit, anode and negative electrode are coupled together, survey
The I-E characteristic of the luminous efficiency of metering device, luminescent spectrum and device.
Embodiment 14
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
(compound 7 and GD-19 are according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI,
Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).
Embodiment 15
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
(compound 10 and GD-19 are according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).
Embodiment 16
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
(compound 15 and GD-19 are according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).
Embodiment 17
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
(compound 21 and GD-19 are according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).
Embodiment 18
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
(compound 26 and GD-19 are according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).
Embodiment 19
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
(compound 27 and Ir (PPy) 3 are according to 100 for 80nm)/luminescent layer 5:10 weight is than blending, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).
Embodiment 20
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
(compound 36 and Ir (PPy) 3 are according to 100 for 80nm)/luminescent layer 5:10 weight is than blending, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).
Embodiment 21
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
(compound 41 and GD-PACTZ are according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).
Embodiment 22
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
(compound 44 and GD-PACTZ are according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).
Embodiment 23
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
(compound 45, GH-204 and Ir (PPy) 3 are according to 70 for 80nm)/luminescent layer 5:30:10 weight is than blending, thickness 30nm)/electricity
Sub- transport layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).
Embodiment 24
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
(compound 52, GH-204 and GD-PACTZ are according to 70 for 80nm)/luminescent layer 5:30:5 weight is than blending, thickness 30nm)/electronics
Transport layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).
Comparative example 1
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
(CBP and GD-19 is according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, thickness
40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).
Comparative example 2
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
(CBP and Ir (PPy) 3 is according to 100 for 80nm)/luminescent layer 5:10 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI,
Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).
Comparative example 3
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
(CBP and GD-PACTZ is according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, 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
Explanation:Using comparative example 1 as reference, comparative example 1 device property indices are set to 1.0 to device detection performance.Than
It is 6.5cd/A (@10mA/cm compared with the current efficiency of example 12)；CIE chromaticity coordinates is (0.32,0.61)；The LT95 life-span under 5000 brightness
Decay to 3.8Hr.Life-span test system is the OLED life test of owner of the present invention and Shanghai University's joint research
Instrument.
The result of table 3 can be seen that compound of the present invention can be applied and OLED luminous organ as luminescent layer material of main part
Part makes, and compared with comparative example 1, either efficiency or life-span all ratio known OLED material larger changes of acquisition, especially
It is the larger lifting of the driving life-span acquisition of device.
From the point of view of data above application, the compounds of this invention has well as emitting layer material in OLED luminescent device
Application effect, there is good industrialization prospect.
Although the present invention has been disclosed by embodiment and preferred implementation it should be appreciated that the invention is not restricted to institute's public affairs
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
The scope of attached claim should arrangement to cover all such modifications and be similar to consistent with explanation the widest.
Claims (6)
1. a kind of with benzimidazole and the compound as core for the ring is it is characterised in that shown in this compound structure such as formula (1)：
In formula (1), X represent oxygen atom, sulphur atom or
Ar1、Ar2、Ar3Expression independentlyOr-R；
Wherein, Ar represents phenyl, C1-10The phenyl of straight or branched alkyl replacement, dibiphenylyl, terphenyl, naphthyl；
N takes 1 or 2；
R chooses hydrogen atom, formula (2) or structure shown in formula (3), and Ar1、Ar2、Ar3In R at least selection formula
Or structure shown in formula (3) (2)：
Wherein, Ar4Represent phenyl, C1-10Phenyl, dibiphenylyl, terphenyl or naphthyl that straight or branched alkyl replaces；
R1、R2、R3Carbon atom of choosing independently is the alkyl of 1-10, phenyl, C1-10The phenyl of straight or branched alkyl replacement,
Dibiphenylyl, terphenyl, naphthyl, formula (4), formula (5), formula (6) or structure shown in formula (7)；And R2、R3When different
For hydrogen：
Wherein, Ar5、Ar6、Ar7Expression phenyl independently, C1-10Straight or branched alkyl replace phenyl, dibiphenylyl, three
Xenyl, naphthyl, C1-10The benzofuranyl of straight or branched alkyl replacement, C1-10The benzo thiophene that straight or branched alkyl replaces
Fen base, C1-10Fluorenyl or C that straight or branched alkyl replaces1-10The carbazyl that straight or branched alkyl replaces；
X1It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10The alkylene that the alkylidene of straight or branched alkyl replacement, aryl replace
One of tertiary amine groups that base, alkyl or aryl replace.
2. compound according to claim 1 is it is characterised in that described R3It is expressed as formula (4), formula (6) or formula (7)
During shown structure, R2It is also denoted as hydrogen atom.
3. compound according to claim 1 is it is characterised in that described R is：
In any one.
4. compound according to claim 1 is it is characterised in that the concrete structure formula of described compound is：
In any one.
5. a kind of luminescent device comprising compound described in any one of Claims 1 to 4 is it is characterised in that described compound conduct
The material of main part of luminescent layer, for making OLED.
6. a kind of method preparing compound described in any one of Claims 1 to 4 is it is characterised in that reaction side in preparation process
Formula is：
N in reaction equation 1～3, m independently be expressed as 0 or 1；
The preparation method of wherein reaction equation 1 is：
Weigh benzimidazole the bromo-derivative of ring, Ar1-H、Ar2- H, is dissolved with toluene；Add Pd2(dba)3, tri-butyl 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 is little
When, cooling simultaneously filtering reacting solution, filtrate revolving, cross silicagel column, obtain target product；Described benzimidazole the bromo-derivative of ring
With Ar1-H、Ar2The mol ratio of-H is 1:0.8～2.0:0.8～2.0, Pd2(dba)3With the mol ratio of bromo-derivative be 0.006～
0.02:1, tri-butyl phosphine is 0.006～0.02 with the mol ratio of bromo-derivative:1, sodium tert-butoxide with the mol ratio of bromo-derivative is
1.0～3.0:1；
The preparation method of reaction equation 2 is：
Weigh benzimidazole benzimidazole and Ar3- Br, is dissolved with toluene；Add Pd2(dba)3, tri-butyl phosphine, the tert-butyl alcohol
Sodium；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in 95～110 DEG C of reaction temperature, react 10～24 hours, cooling
And filtering reacting solution, filtrate revolving, cross silicagel column, obtain target product；Described benzimidazole benzimidazole and Ar3- Br's
Mol ratio is 0.8～2.0:1, Pd2(dba)3With Ar3The mol ratio of-Br is 0.006～0.02:1, tri-butyl phosphine and Ar3-Br
Mol ratio be 0.006～0.02:1, sodium tert-butoxide and Ar3The mol ratio of-Br is 1.0～3.0:1；
The preparation method of reaction equation 3 is：
Weigh benzimidazole the bromo-derivative of ring, Ar1-B(OH)2、Ar2-B(OH)2, it is 2 with volume ratio:1 toluene ethanol mixing
Solvent dissolves；Under an inert atmosphere, add Na2CO3Aqueous solution, Pd (PPh3)4；By the mixed solution of above-mentioned reactant in anti-
Answer 95～110 DEG C of temperature, react 10～24 hours, cooling simultaneously filtering reacting solution, filtrate revolving, cross silicagel column, obtain target
Product；Described bromo compound and Ar1-B(OH)2、Ar2-B(OH)2Mol ratio be 1:1.0～2.0:1.0～2.0；Na2CO3
Mol ratio with bromo-derivative is 1.0～3.0:1；Pd(PPh3)4Mol ratio with bromo-derivative is 0.006～0.02:1.
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