CN101414661B - Organic electron transport and/or hole blocking material, and synthesis method and application thereof - Google Patents
Organic electron transport and/or hole blocking material, and synthesis method and application thereof Download PDFInfo
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- CN101414661B CN101414661B CN200710176008.3A CN200710176008A CN101414661B CN 101414661 B CN101414661 B CN 101414661B CN 200710176008 A CN200710176008 A CN 200710176008A CN 101414661 B CN101414661 B CN 101414661B
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- phenanthrene
- coughed
- quinolyl
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- 239000000463 material Substances 0.000 title claims abstract description 48
- 230000000903 blocking effect Effects 0.000 title abstract description 7
- 238000001308 synthesis method Methods 0.000 title 1
- 230000005540 biological transmission Effects 0.000 claims abstract description 28
- 150000003222 pyridines Chemical class 0.000 claims abstract description 20
- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000010189 synthetic method Methods 0.000 claims abstract description 6
- -1 isobutyl- Chemical group 0.000 claims description 271
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 89
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 52
- 238000003756 stirring Methods 0.000 claims description 50
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 44
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 26
- 239000005695 Ammonium acetate Substances 0.000 claims description 26
- 229960000583 acetic acid Drugs 0.000 claims description 26
- 229940043376 ammonium acetate Drugs 0.000 claims description 26
- 235000019257 ammonium acetate Nutrition 0.000 claims description 26
- 230000004888 barrier function Effects 0.000 claims description 26
- 238000004440 column chromatography Methods 0.000 claims description 26
- 238000005401 electroluminescence Methods 0.000 claims description 26
- 239000012362 glacial acetic acid Substances 0.000 claims description 26
- 239000002994 raw material Substances 0.000 claims description 26
- 238000001953 recrystallisation Methods 0.000 claims description 26
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 24
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 5
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- GIEFFCXIJRRYFW-UHFFFAOYSA-N Br[BrH]Br.c1ccncc1 Chemical compound Br[BrH]Br.c1ccncc1 GIEFFCXIJRRYFW-UHFFFAOYSA-N 0.000 claims description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 230000010354 integration Effects 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000005594 diketone group Chemical group 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000008569 process Effects 0.000 abstract description 3
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000006378 damage Effects 0.000 abstract description 2
- 238000013461 design Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 52
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 48
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 48
- 238000002360 preparation method Methods 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 29
- 229910052757 nitrogen Inorganic materials 0.000 description 28
- UHNOAGDNODCLKN-UHFFFAOYSA-N bromine;pyridine Chemical compound [Br].C1=CC=NC=C1 UHNOAGDNODCLKN-UHFFFAOYSA-N 0.000 description 24
- 238000004900 laundering Methods 0.000 description 24
- GJSJZQZEDAUFBH-UHFFFAOYSA-N benzene;pentan-3-one Chemical compound CCC(=O)CC.C1=CC=CC=C1 GJSJZQZEDAUFBH-UHFFFAOYSA-N 0.000 description 23
- 238000001704 evaporation Methods 0.000 description 17
- 230000008020 evaporation Effects 0.000 description 17
- 229910052740 iodine Inorganic materials 0.000 description 12
- 239000011630 iodine Substances 0.000 description 12
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- LJANCPRIUMHGJE-UHFFFAOYSA-N 4-(2-bromoacetyl)benzonitrile Chemical compound BrCC(=O)C1=CC=C(C#N)C=C1 LJANCPRIUMHGJE-UHFFFAOYSA-N 0.000 description 6
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 5
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 5
- OTXINXDGSUFPNU-UHFFFAOYSA-N 4-tert-butylbenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C=C1 OTXINXDGSUFPNU-UHFFFAOYSA-N 0.000 description 4
- RJCQBQGAPKAMLL-UHFFFAOYSA-N bromotrifluoromethane Chemical compound FC(F)(F)Br RJCQBQGAPKAMLL-UHFFFAOYSA-N 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 3
- 229910001316 Ag alloy Inorganic materials 0.000 description 3
- 235000014493 Crataegus Nutrition 0.000 description 3
- 241001092040 Crataegus Species 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 125000006278 bromobenzyl group Chemical group 0.000 description 3
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 3
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
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- QCUQMQNAGDAQKB-UHFFFAOYSA-N Cc(cc1)ccc1-c1c(C(F)(F)F)c(-c2ccccc2)nc(-c2cc(-c3nc(-c4ccccc4)c(C(F)(F)F)c(-c4ccc(C)cc4)c3)ccc2)c1 Chemical compound Cc(cc1)ccc1-c1c(C(F)(F)F)c(-c2ccccc2)nc(-c2cc(-c3nc(-c4ccccc4)c(C(F)(F)F)c(-c4ccc(C)cc4)c3)ccc2)c1 QCUQMQNAGDAQKB-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 0 FC(c(cccc1)c1-c1nc(-c2ccccc2-c2nc(-c3*(C4(F)F)cccc3)c4c(-c3c[o]cc3)c2)c2)(c1c2-c1c[o]cc1)F Chemical compound FC(c(cccc1)c1-c1nc(-c2ccccc2-c2nc(-c3*(C4(F)F)cccc3)c4c(-c3c[o]cc3)c2)c2)(c1c2-c1c[o]cc1)F 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 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 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OAAQPYUFAOHUMT-UHFFFAOYSA-N N-butyl-N-(3-carboxypropyl)nitrosamine Chemical compound CCCCN(N=O)CCCC(O)=O OAAQPYUFAOHUMT-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000005685 electric field effect Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000008863 intramolecular interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- KYKLWYKWCAYAJY-UHFFFAOYSA-N oxotin;zinc Chemical compound [Zn].[Sn]=O KYKLWYKWCAYAJY-UHFFFAOYSA-N 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 125000005543 phthalimide group Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 230000004304 visual acuity Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention belongs to the field of organic electron transport/hole blocking materials in organic electroluminescent devices, and particularly relates to an organic electron transport and/or hole blocking materialA polyaryl substituted pyridine derivative, a synthetic method thereof and application of the polyaryl substituted pyridine derivative material in preparing organic electroluminescent devices. According to the invention, through molecular design, a plurality of large substituent groups with rigid structures are introduced, so that exciplex is not easy to form, the crystallization process is inhibited, the film forming property is improved, and the charge transmission performance is improved; meanwhile, the damage of molecular coplanarity can make the emission peak blue shift, thereby achieving the purpose of improving the performance of the device. The polyaryl substituted pyridine derivative disclosed by the invention comprises the following structure.
Description
Technical field
The invention belongs to the organic electronic transmission/hole barrier materials field in the organic electroluminescence device, be particularly related to a class polyaryl substituted pyridine derivative and a synthetic method thereof that is used for organic electronic transmission and/or hole barrier materials, and with the purposes of such polyaryl substituted pyridine derivative material preparation organic electroluminescence device aspect.
Along with the arriving of Development of Multimedia Technology and information society, more and more higher to the flat-panel monitor performance demands.In recent years emerging three kinds of technique of display: plasma display, Field Emission Display and display of organic electroluminescence (OLED) have all remedied the deficiency of cathode ray tube (CRT) and liquid-crystal display (LCD) to a certain extent.Wherein, a series of advantages such as OLED has from main light emission, low voltage direct drive, solidifies entirely, the visual angle is wide, color is abundant, compare with liquid-crystal display, OLED does not need backlight, the visual angle is big, low in energy consumption, its response speed reaches 1000 times of liquid-crystal display, its manufacturing cost but is lower than the liquid-crystal display of equal resolving power, therefore, organic electroluminescent LED (OLEDs) is owing to its potential application in indicating meter of new generation and lighting engineering causes extensive attention, and its application prospect is very wide.Organic electroluminescence device is spontaneous luminescent device, and the luminous mechanism of OLED is under the extra electric field effect, and electronics and hole are injected the back from positive and negative polarities respectively and produced luminous in organic materials migration, compound and decay.The typical structure of OLED comprises cathode layer, anode layer, and the organic thin film layer between this is two-layer, can comprise one or more functional layers in electron injecting layer, electron transfer layer, hole blocking layer, hole transmission layer, hole injection layer and the organic luminous layer in the organic thin film layer.Since the C.W.Tang of Eastman Kodak Company (C.W.Tang and S.A.Vans lyke, Applied Physics Letters, Volume 51, P913,1987) reported since the laminated type organic electroluminescent device of low voltage drive, people have carried out a lot of researchs (U.S.Pat.Nos.5,141,671 to utilizing organic materials as the organic electroluminescence device of composition material; 4,539,507; 6,020,078; 5,935,720; 5,972,247; 5,593,788; 4,885,211; 5,059,862; 5,104,740; 5,069,975; 5,126,214; 5,389,444; 6,165,383; 6,245,449; 6,861,162B2; 6,833,202B2; Chen, Shi and Tang, Macromol.Symp., 1997,125,1; Segura, Acta.Polym., 1998,49,319; Mitschke and Bauerle, J.Mater.Chem.2000,10,1471).Yet, although have
Pyridine ring is because its electron deficiency characteristic has certain electronegativity, and its reduction potential is about 2.6eV (vsSCE).Its polymkeric substance, at 2.9～3.5eV, and therefore Ip can be used as the electron transport material in the polymer electroluminescent device at 5.7～6.3eV as the EA value of polypyridine.Yet,, its luminosity is changed because its strong intramolecular interaction (overlapping as ∏-∏) easily forms exciplex in film.Therefore, device performance is not good enough.So far seldom in organic electroluminescence device, use.
Summary of the invention
The objective of the invention is to overcome the problem that exists in the above-mentioned organic electronic transmission/hole barrier materials, the organic electronic transmission and/or the hole barrier materials of a class polyaryl substituted pyridine derivative is provided; By molecular designing, introduce some large-substituents and make it be difficult for forming exciplex, and suppress its crystallisation process with rigid structure, improve its film-forming properties, improve its charge transport properties; Simultaneously, the destruction of molecule coplanarity will make its emission peak blue shift, and then reach the purpose of improving device performance.
A further object of the present invention provides the organic electronic transmission of purpose one and/or the synthetic method of hole barrier materials.
Organic electronic transmission and/or hole barrier materials that an also purpose of the present invention provides purpose one are used to prepare organic electroluminescence device, especially the purposes of blue organic electroluminescence device aspect.
The present invention relates to the organic electronic transmission and/or the hole barrier materials of the polyaryl substituted pyridine derivative of a class tool electrophilic character, this compounds has very high electron affinity (about 3.5eV) and ionization potential (about 7.0eV), can be used for the electron transport material and/or the hole barrier materials of organic electroluminescence device.The molecular structure of material of the present invention is shown in following general formula.With the prepared organic electroluminescence device of material of the present invention because and have only very little barrier potential (about 0.2eV) between the negative electrode, electronic energy is injected in the organic luminous layer effectively, so its device has a very low bright voltage (2.7eV), simultaneously because high ionization potential (about 7.0eV) is arranged, blocking hole is diffused into negative electrode effectively, thereby the limit that reaches hole and electronics obtains effect.Material of the present invention has very high photoluminescence efficiency (about 100%) and ultraviolet region emission wavelength (370nm), there is not the quencher phenomenon that causes because of energy transformation, can be used for making all organic electroluminescence devices, blue-light device particularly, thus the performance of corresponding electron luminescence device improved effectively.Material of the present invention has high glass-transition temperature and high thermal stability simultaneously, so the life-span of electroluminescent device is effectively improved.
The present invention adopts easy method to synthesize a series of class polyaryl substituted pyridine derivatives with efficent electronic transmission and/or hole barrier materials.Organic electroluminescence device of the present invention comprises negative electrode, anode and organic thin film layer, at least comprise organic luminous layer in the organic thin film layer between negative electrode and anode, and in the organic thin film layer at least one deck comprise following general formula (I), (II) or (III) the polyaryl substituted pyridine derivative of expression.The polyaryl substituted pyridine derivative that preferred organic thin film layer comprises general formula (I), (II) or (III) represents.The molecular structure of a class polyaryl substituted pyridine derivative of the present invention is as follows:
Wherein:
R
1, R
3, R
3', R
4, R
4' substituting group can be identical or different, independently be selected from hydrogen respectively, have the replacement or the unsubstituted alkyl of 1 to 20 carbon atom, replacement or unsubstituted cycloalkyl with 5 to 20 carbon atoms, have 1 to 20 carbon atom alkoxyl group, have 6 to 60 carbon atoms aralkyl, have 6 to 50 ring carbon atoms aryl, have the aryloxy of 6 to 50 annular atomses or have a kind of in the aromatic heterocyclic group of 5 to 50 annular atomses;
R
2, R
2', R
5, R
5' substituting group can be identical or different, independently be selected from hydrogen, carboxyl, fluoro methyl, cyano group, nitro respectively or have a kind of in the ester group etc. of 2 to 20 carbon atoms;
Ar
1, Ar
1', Ar
2, Ar
2' substituting group can be identical or different, a kind of in the aromatic heterocyclic group that independently be selected from aryl with 6 to 50 ring carbon atoms respectively, has 5 to 50 annular atomses.
Described R
1, R
3, R
3', R
4, R
4' in the not substituted alkyl with 1 to 20 carbon atom be methyl, ethyl, propyl group, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl, n-heptyl or n-octyl.
Described R
1, R
3, R
3', R
4, R
4' in the substituted alkyl with 1 to 20 carbon atom be methylol, the 1-hydroxyethyl, the 2-hydroxyethyl, 2-hydroxyl isobutyl-, 1, the 2-dihydroxy ethyl, 1,3-dihydroxyl sec.-propyl, 2, the 3 one dihydroxyl-tertiary butyl, 1,2,3 one trihydroxy-propyl group, chloromethyl, the 1-chloroethyl, the 2-chloroethyl, 2-chlorine isobutyl-, 1, the 2-Dichloroethyl, 1,3-two chloro isopropyls, 2, the 3-two chloro-tertiary butyls, 1,2,3-three chloropropyls, brooethyl, the 1-bromotrifluoromethane, the 2-bromotrifluoromethane, 2-melts isobutyl-, 1,2-two bromotrifluoromethanes, 1,3-dibromo sec.-propyl, 2, the 3-two bromo-tertiary butyls, I, 2,3-three bromopropyls, iodomethyl, 1-iodine ethyl, 2-iodine ethyl, 2-iodine isobutyl-, 1,2-diiodo-ethyl, 1,3-diiodo-sec.-propyl, 2, the 3-two iodo-tertiary butyls, 1,2,3-triiodo propyl group, amino methyl, the 1-amino-ethyl, the 2-amino-ethyl, 2-aminoisobutyric base, 1, the 2-diamino ethyl, 1,3-diamino sec.-propyl, 2,3-diamino-tertiary butyl or 1,2,3-triamino propyl group.
Described R
1, R
3, R
3', R
4, R
4' in the unsubstituted cycloalkyl with 5 to 20 carbon atoms be cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
Described R
1, R
3, R
3', R
4, R
4' in the cycloalkyl of replacement with 5 to 20 carbon atoms be 4-methylcyclohexyl, adamantyl or norborneol alkyl.
Described R
1, R
3, R
3', R
4, R
4' in the alkoxyl group with 1 to 20 carbon atom be by-group that OR represents.Wherein the group represented of R is an alkyl, alkyl comprises methyl, ethyl, propyl group, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, methylol, the 1-hydroxyethyl, the 2-hydroxyethyl, 2-hydroxyl isobutyl-, 1, the 2-dihydroxy ethyl, 1,3-two chloro isopropyls, 2, the 3-two chloro-tertiary butyls, 1,2,3-three chloropropyls, brooethyl, the 1-bromotrifluoromethane, the 2-bromotrifluoromethane, 2-bromine isobutyl-, 1,2-two bromotrifluoromethanes, 1,3-dibromo sec.-propyl, 2, the 3-two bromo-tertiary butyls, 1,2,3-three bromopropyls, iodomethyl, 1-iodine ethyl, 2-iodine ethyl, 2-iodine isobutyl iodide 1,2-diiodo-ethyl, 1,3-diiodo-sec.-propyl, 2, the 3-two iodos-tertiary butyl, 1,2,3-triiodo propyl group, iodomethyl, 1-iodine ethyl, 2-iodine ethyl, 2-iodine isobutyl-, 1,2-diiodo-ethyl, 1,3-diiodo-sec.-propyl, 2, the 3-two iodo-tertiary butyls, 1,2,3-triiodo propyl group, amino methyl, the 1-amino-ethyl, the 2-amino-ethyl, 2-aminoisobutyric base, 1, the 2-diamino ethyl, 1,3-diamino sec.-propyl, 2,3-diamino-tertiary butyl, 1,2,3-triamino propyl group, cyano methyl, the 1-cyano ethyl, the 2-cyano ethyl, 2-cyano group isobutyl-, 1,2-dicyano ethyl, 1,3-dicyano sec.-propyl, 2,3-dicyano-tertiary butyl, 1,2,3-tricyano propyl group, the nitro methyl, the 1-nitro-ethyl, the 2-nitro-ethyl, 2-nitro isobutyl-, 1,2-dinitrobenzene ethyl, 1,3-dinitrobenzene sec.-propyl, 2,3-dinitrobenzene-tertiary butyl or 1,2,3-trinitro-propyl group.
Described R
1, R
3, R
3', R
4, R
4' in have 6 to 60 carbon atoms aralkyl be benzyl, 1-phenylethyl, the 2-phenylethyl, 1-propyloxy phenyl base, 2-propyloxy phenyl base, the phenyl tertiary butyl, the Alpha-Naphthyl methyl, 1-Alpha-Naphthyl ethyl, 2-Alpha-Naphthyl ethyl, 1-Alpha-Naphthyl sec.-propyl, 2-Alpha-Naphthyl sec.-propyl, the betanaphthyl methyl, 1-betanaphthyl ethyl, 2-betanaphthyl ethyl, 1-betanaphthyl sec.-propyl, 2-betanaphthyl sec.-propyl, 1-pyrryl methyl, 2-(1-pyrryl) ethyl, to methyl-benzyl, between methyl-benzyl, adjacent methyl-benzyl, p-chlorobenzyl, the m-chloro benzyl, o-chlorobenzyl, to bromobenzyl, between bromobenzyl, adjacent bromobenzyl, to the iodine benzyl, between the iodine benzyl, adjacent iodine benzyl, PAB, between aminobenzyl, adjacent aminobenzyl, to nitrobenzyl, between nitrobenzyl, adjacent nitrobenzyl, to the cyano group benzyl, between the cyano group benzyl, o-cyanobenzyl, 1-chloro-2-propyloxy phenyl base or trityl.
Described R
1, R
3, R
3', R
4, R
4' in have 6 to 50 ring carbon atoms aryl be phenyl, the 1-naphthyl, the 2-naphthyl, the 1-anthryl, the 2-anthryl, the 9-anthryl, the 1-phenanthryl, the 2-phenanthryl, the 3-phenanthryl, the 4-phenanthryl, the 9-phenanthryl, the 1-naphthacenyl, the 2-naphthacenyl, the 9-naphthacenyl, the 1-pyrenyl, the 2-pyrenyl, the 4-pyrenyl, the 2-xenyl, the 3-xenyl, the 4-xenyl, p-terphenyl-4-base, p-terphenyl-3-base, p-terphenyl-2-base, meta-terphenyl-4-base, meta-terphenyl-3-base, meta-terphenyl-2-base, o-tolyl, between tolyl, p-methylphenyl, to tert-butyl-phenyl, right-(2-phenyl propyl) phenyl, 3-methyl-2-naphthyl, 4-methyl isophthalic acid-naphthyl, 4-methyl isophthalic acid-anthryl, 4 '-methyl biphenyl or 4 "-tertiary butyl-p-terphenyl-4-base.
Described R
1, R
3, R
3', R
4, R
4' in have 6 to 50 annular atomses aryloxy be by-group that OAr represents.Wherein the group represented of Ar is an aromatic group, aromatic group comprises phenyl, the 1-naphthyl, the 2-naphthyl, the 1-anthryl, the 2-anthryl, the 9-anthryl, the 1-phenanthryl, the 2-phenanthryl, the 3-phenanthryl, the 4-phenanthryl, the 9-phenanthryl, the 1-naphthacenyl, the 2-naphthacenyl, the 9-naphthacenyl, the 1-pyrenyl, the 2-pyrenyl, the 4-pyrenyl, the 2-xenyl, the 3-xenyl, the 4-xenyl, p-terphenyl-4-base, p-terphenyl-3-base, p-terphenyl-2-base, meta-terphenyl-4-base, meta-terphenyl-3-base, meta-terphenyl-2-base, o-tolyl, between tolyl, p-methylphenyl, to tert-butyl-phenyl, right-(2-phenyl propyl) phenyl, 3-methyl-2-naphthyl, 4-methyl isophthalic acid-naphthyl, 4-methyl isophthalic acid-naphthyl, 4 '-methyl biphenyl; 4 "-the tertiary butyl-p-terphenyl-4-base, the 2-pyrryl, the 3-pyrryl, pyridyl, the 2-pyridyl, the 3-pyridyl, the 4-pyridyl, the 2-indyl, the 3-indyl, the 4-indyl, the 5-indyl, the 6-indyl, the 7-indyl, the 1-pseudoindoyl, the 3-pseudoindoyl, the 4-pseudoindoyl, the 5-pseudoindoyl, the 6-pseudoindoyl, the 7-pseudoindoyl, the 2-furyl, the 3-furyl, the 2-benzofuryl, the 3-benzofuryl, the 4-benzofuryl, the 5-benzofuryl, the 6-benzofuryl, the 7-benzofuryl, the 1-isobenzofuran-base, the 3-isobenzofuran-base, the 4-isobenzofuran-base, the 5-isobenzofuran-base, the 6-isobenzofuran-base, 7-isobenzofuran-base 2-quinolyl, the 3-quinolyl, the 4-quinolyl, the 5-quinolyl, the 6-quinolyl, the 7-quinolyl, the 8-quinolyl, the 1-isoquinolyl, the 3-isoquinolyl, the 4-isoquinolyl, the 5-isoquinolyl, the 6-isoquinolyl, the 7-isoquinolyl, the 8-isoquinolyl, the 2-quinoxalinyl, the 5-quinoxalinyl, the 6-quinoxalinyl, the 1-carbazyl, the 2-carbazyl, the 3-carbazyl, the 4-carbazyl, the 1-phenanthridinyl, the 2-phenanthridinyl, the 3-phenanthridinyl, the 4-phenanthridinyl, the 6-phenanthridinyl, the 7-phenanthridinyl, the 8-phenanthridinyl, the 9-phenanthridinyl, the 10-phenanthridinyl, the 1-acridyl, the 2-acridyl, the 3-acridyl, the 4-acridyl, the 9-acridyl, 1, the 7-phenanthrene is coughed up beautiful jade-2-base, 1, the 7-phenanthrene is coughed up beautiful jade-3-base, 1, the 7-phenanthrene is coughed up beautiful jade-4-base, 1, the 7-phenanthrene is coughed up beautiful jade-5-base, 1, the 7-phenanthrene is coughed up beautiful jade-6-base, 1, the 7-phenanthrene is coughed up beautiful jade-8-base, 1, the 7-phenanthrene is coughed up beautiful jade-9-base, 1, the 7-phenanthrene is coughed up beautiful jade-10-base, 1, the 8-phenanthrene is coughed up beautiful jade-2-base, 1, the 8-phenanthrene is coughed up beautiful jade-3-base, 1, the 8-phenanthrene is coughed up beautiful jade-4-base, 1, the 8-phenanthrene is coughed up beautiful jade-5-base, 1, the 8-phenanthrene is coughed up beautiful jade-6-base, 1, the 8-phenanthrene is coughed up beautiful jade-7-base, 1, the 8-phenanthrene is coughed up beautiful jade-9-base, 1, the 8-phenanthrene is coughed up beautiful jade-10-base, 1, the 9-phenanthrene is coughed up beautiful jade-2-base, 1, the 9-phenanthrene is coughed up beautiful jade-3-base, 1, the 9-phenanthrene is coughed up beautiful jade-4-base, 1, the 9-phenanthrene is coughed up beautiful jade-5-base, 1, the 9-phenanthrene is coughed up beautiful jade-6-base, 1, the 9-phenanthrene is coughed up beautiful jade-7-base, 1, the 9-phenanthrene is coughed up beautiful jade-8-base, 1, the 9-phenanthrene is coughed up beautiful jade-10-base, 1, the 10-phenanthrene is coughed up beautiful jade-2-base, 1, the 10-phenanthrene is coughed up beautiful jade-3-base, 1, the 10-phenanthrene is coughed up beautiful jade-4-base, 1, the 10-phenanthrene is coughed up beautiful jade-5-base, 2, the 9-phenanthrene is coughed up beautiful jade-1-base, 2, the 9-phenanthrene is coughed up beautiful jade-3-base, 2, the 9-phenanthrene is coughed up beautiful jade-4-base, 2, the 9-phenanthrene is coughed up beautiful jade-5-base, 2, the 9-phenanthrene is coughed up beautiful jade-6-base, 2, the 9-phenanthrene is coughed up beautiful jade-7-base, 2, the 9-phenanthrene is coughed up beautiful jade 8-base, 2, the 9-phenanthrene is coughed up beautiful jade-10-base, 2, the 8-phenanthrene is coughed up beautiful jade-1-base, 2, the 8-phenanthrene is coughed up beautiful jade-3-base, 2, the 8-phenanthrene is coughed up beautiful jade-4-base, 2, the 8-phenanthrene is coughed up beautiful jade-5-base, 2, the 8-phenanthrene is coughed up beautiful jade-6-base, 2, the 8-phenanthrene is coughed up beautiful jade-7-base, 2, the 8-phenanthrene is coughed up beautiful jade-9-base, 2, the 8-phenanthrene is coughed up beautiful jade-10-base, 2, the 7-phenanthrene is coughed up beautiful jade-1-base, 2, the 7-phenanthrene is coughed up beautiful jade-3-base, 2, the 7-phenanthrene is coughed up beautiful jade-4-base, 2, the 7-phenanthrene is coughed up beautiful jade-5-base, 2, the 7-phenanthrene is coughed up beautiful jade-6-base, 2, the 7-phenanthrene is coughed up beautiful jade-8-base, 2, the 7-phenanthrene is coughed up beautiful jade-9-base, 2, the 7-phenanthrene is coughed up beautiful jade-10-base, the 1-phenazinyl, the 2-phenazinyl, the 1-phenothiazinyl, the 2-phenothiazinyl, the 3-phenothiazinyl, the 4-phenothiazinyl, the 1-phenoxazinyl, the 2-phenoxazinyl, the 3-phenoxazinyl, the 4-phenoxazinyl, the 2-oxazole. base, the 4-oxazolyl, the 5-oxazolyl, 2-oxadiazole base, 5-oxadiazole base, 3-furazan base, the 2-thienyl, the 3-thienyl, 2-methylpyrrole-1-base, 2-methylpyrrole-3-base, 2-methylpyrrole-4-base, 2-methylpyrrole-5-base, 3-methylpyrrole-1-base, 3-methylpyrrole-2-base, 3-methylpyrrole-4-base, 3-methylpyrrole-5-base, 2-tertiary butyl pyrroles-4-base, 3-(2-phenyl propyl) pyrroles-1-base, 2-methyl isophthalic acid-indyl, 4-methyl isophthalic acid-indyl, 2-methyl-3-indyl, 4-methyl-3-indyl, the 2-tertiary butyl-1-indyl, the 4-tertiary butyl-1-indyl, the 2-tertiary butyl-3-indyl or the 4-tertiary butyl-3-indyl.
Described R
1, R
3, R
3', R
4, R
4' in have 5 to 50 annular atomses aromatic heterocyclic group be the 1-pyrryl, the 2-pyrryl, the 3-pyrryl, pyridyl, the 2-pyridyl, the 3-pyridyl, the 4-pyridyl, the 1-indyl, the 2-indyl, the 3-indyl, the 4-indyl, the 5-indyl, the 6-indyl, the 7-indyl, the 1-pseudoindoyl, the 2-pseudoindoyl, the 3-pseudoindoyl, the 4-pseudoindoyl, the 5-pseudoindoyl, the 6-pseudoindoyl, the 7-pseudoindoyl, the 2-furyl, the 3-furyl, the 2-benzofuryl, the 3-benzofuryl, the 4-benzofuryl, the 5-benzofuryl, the 6-benzofuryl, the 7-benzofuryl, the 1-isobenzofuran-base, the 3-isobenzofuran-base, the 4-isobenzofuran-base, the 5-isobenzofuran-base, the 6-isobenzofuran-base, the 7-isobenzofuran-base, the 2-quinolyl, the 3-quinolyl, the 4-quinolyl, the 5-quinolyl, the 6-quinolyl, the 7-quinolyl, the 8-quinolyl, the 1-isoquinolyl, the 3-isoquinolyl, the 4-isoquinolyl, the 5-isoquinolyl, the 6-isoquinolyl, the 7-isoquinolyl, the 8-isoquinolyl, 2-quinoxalinyl (quinoxanyl), 5-quinoxalinyl (quinoxanyl), 6-quinoxalinyl (quinoxanyl), the 1-carbazyl, the 2-carbazyl, the 3-carbazyl, the 4-carbazyl, the 9-carbazyl, 1-coffee pyridine base, 2-coffee pyridine base, 3-coffee pyridine base, 4-coffee pyridine base, 6-coffee pyridine base, 7-coffee pyridine base, 8-coffee pyridine base, 9-coffee pyridine base, 10-coffee pyridine base, the 1-acridyl, the 2-acridyl, the 3-acridyl, the 4-acridyl, the 9-acridyl, 1, the 7-phenanthrene is coughed up beautiful jade-2-base, 1, the 7-phenanthrene is coughed up beautiful jade-3-base, 1, the 7-phenanthrene is coughed up beautiful jade-4-base, 1, the 7-phenanthrene is coughed up beautiful jade-5-base, 1, the 7-phenanthrene is coughed up beautiful jade-6-base, 1, the 7-phenanthrene is coughed up beautiful jade-8-base, 1, the 7-phenanthrene is coughed up beautiful jade-9-base, 1, the 7-phenanthrene is coughed up beautiful jade-10-base, 1, the 8-phenanthrene is coughed up beautiful jade-2-base, 1, the 8-phenanthrene is coughed up beautiful jade-3-base, 1, the 8-phenanthrene is coughed up beautiful jade-4-base, 1, the 8-phenanthrene is coughed up beautiful jade-5-base, 1, the 8-phenanthrene is coughed up beautiful jade-6-base, 1, the 8-phenanthrene is coughed up beautiful jade-7-base, 1, the 8-phenanthrene is coughed up beautiful jade-9-base, 1, the 8-phenanthrene is coughed up beautiful jade-10-base, 1, the 9-phenanthrene is coughed up beautiful jade-2-base, 1, the 9-phenanthrene is coughed up beautiful jade-3-base, 1, the 9-phenanthrene is coughed up beautiful jade-4-base, 1, the 9-phenanthrene is coughed up beautiful jade-5-base, 1, the 9-phenanthrene is coughed up beautiful jade-6-base, 1, the 9-phenanthrene is coughed up beautiful jade-7-base, 1, the 9-phenanthrene is coughed up beautiful jade-8-base, 1, the 9-phenanthrene is coughed up beautiful jade-10-base, 1, the 10-phenanthrene is coughed up beautiful jade-2-base, 1, the 10-phenanthrene is coughed up beautiful jade-3-base, 1, the 10-phenanthrene is coughed up beautiful jade-4-base, 1, the 10-phenanthrene is coughed up beautiful jade-5-base, 2,9-phenanthrolines-1-base, 2, the 9-phenanthrene is coughed up beautiful jade-3-base, 2, the 9-phenanthrene is coughed up beautiful jade-4-base, 2, the 9-phenanthrene is coughed up beautiful jade-5-base, 2, the 9-phenanthrene is coughed up beautiful jade-6-base, 2, the 9-phenanthrene is coughed up beautiful jade-7-base, 2, the 9-phenanthrene is coughed up beautiful jade-8-base, 2, the 9-phenanthrene is coughed up beautiful jade-10-base, 2, the 8-phenanthrene is coughed up beautiful jade-1-base, 2, the 8-phenanthrene is coughed up beautiful jade-3-base, 2, the 8-phenanthrene is coughed up beautiful jade-4-base, 2, the 8-phenanthrene is coughed up beautiful jade-5-base, 2, the 8-phenanthrene is coughed up beautiful jade-6-base, 2, the 8-phenanthrene is coughed up beautiful jade-7-base, 2, the 8-phenanthrene is coughed up beautiful jade-9-base, 2, the 8-phenanthrene is coughed up beautiful jade-10-base, 2, the 7-phenanthrene is coughed up beautiful jade-1-base, 2, the 7-phenanthrene is coughed up beautiful jade-3-base, 2, the 7-phenanthrene is coughed up beautiful jade-4-base, 2, the 7-phenanthrene is coughed up beautiful jade-5-base, 2, the 7-phenanthrene is coughed up beautiful jade-6-base, 2, the 7-phenanthrene is coughed up beautiful jade-8-base, 2, the 7-phenanthrene is coughed up beautiful jade-9-base, 2, the 7-phenanthrene is coughed up beautiful jade-10-base, the 1-phenazinyl, the 2-phenazinyl, the 1-phenothiazinyl, the 2-phenothiazinyl, the 3-phenothiazinyl, the 4-phenothiazinyl, the lysivane base, the 1-phenoxazinyl, the 2-phenoxazinyl, the 3-phenoxazinyl, the 4-phenoxazinyl, the 10-phenoxazinyl, the 2-oxazolyl, the 4-oxazolyl, the 5-oxazolyl, 2-oxadiazole base, 5-oxadiazole base, 3-furazan base (furazanyl), the 2-thienyl, the 3-thienyl, 2-picoline-1-base, 2-methylpyrrole-3-base, 2-methylpyrrole-4-base, 2-methylpyrrole-5-base, 3-methylpyrrole-1-base, 3-methylpyrrole-2-base, 3-methylpyrrole-4-base, 3-methylpyrrole-5-base, 2-tertiary butyl pyrroles-4-base, 3-(2-phenyl propyl) pyrroles one-1-base, 2-methyl isophthalic acid-indyl, 4-methyl isophthalic acid-indyl, 2-methyl-3-indyl, 4-methyl-3-indyl, the 2-tertiary butyl-1-indyl, the 4-tertiary butyl-1-indyl, the 2-tertiary butyl-3-indyl or the 4-tertiary butyl-3-indyl.
Described R
2, R
2', R
5, R
5' in the fluoro methyl be the methyl that a fluorine (as the 1-methyl fluoride), difluoro (as 1, the 1-difluoromethyl) or trifluoro (as 1,1, the 1-trifluoromethyl) replace.
Described R
2, R
2', R
5, R
5' in have 2 to 20 carbon atoms ester group be methoxycarbonyl, ethoxycarbonyl, propyl ester base, isopropyl ester base, positive butyl ester base, Zhong Ding ester group, isobutyl ester group, n-pentyl ester base, just own ester group, positive heptyl ester base or n-octyl base.
Described Ar
1, Ar
1', Ar
2, Ar
2' in have 6 to 50 ring carbon atoms aryl be phenyl, the 1-naphthyl, the 2-naphthyl, the 1-anthryl, the 2-anthryl, the 9-anthryl, the 1-phenanthryl, the 2-phenanthryl, the 3-phenanthryl, the 4-phenanthryl, the 9-phenanthryl, the 1-naphthacenyl, the 2-naphthacenyl, the 9-naphthacenyl, the 1-pyrenyl, the 2-pyrenyl, the 4-pyrenyl, the 2-xenyl, the 3-xenyl, the 4-xenyl, p-terphenyl-4-base, p-terphenyl-3-base, p-terphenyl-2-base, meta-terphenyl-4-base, meta-terphenyl-3-base, meta-terphenyl-2-base, o-tolyl, between tolyl, p-methylphenyl, to tert-butyl-phenyl, right-(2-phenyl propyl) phenyl, 3-methyl-2-naphthyl, 4-methyl isophthalic acid-naphthyl, 4-methyl isophthalic acid-anthryl, 4 '-methyl biphenyl or 4 "-tertiary butyl-p-terphenyl-4-base.
Described Ar
1, Ar
1', Ar
2, Ar
2' in have 5 to 50 annular atomses aromatic heterocyclic radical be the 1-pyrryl, the 2-pyrryl, the 3-pyrryl, pyridyl, the 2-pyridyl, the 3-pyridyl, the 4-pyridyl, the 1-indyl, the 2-indyl, the 3-indyl, the 4-indyl, the 5-indyl, the 6-indyl, the 7-indyl, the 1-pseudoindoyl, the 2-pseudoindoyl, the 3-pseudoindoyl, the 4-pseudoindoyl, the 5-pseudoindoyl, the 6-pseudoindoyl, the 7-pseudoindoyl, the 2-furyl, the 3-furyl, the 2-benzofuryl, the 3-benzofuryl, the 4-benzofuryl, the 5-benzofuryl, the 6-benzofuryl, the 7-benzofuryl, the 1-isobenzofuran-base, the 3-isobenzofuran-base, the 4-isobenzofuran-base, the 5-isobenzofuran-base, the 6-isobenzofuran-base, the 7-isobenzofuran-base, the 2-quinolyl, the 3-quinolyl, the 4-quinolyl, the 5-quinolyl, the 6-quinolyl, the 7-quinolyl, the 8-quinolyl, the 1-isoquinolyl, the 3-isoquinolyl, the 4-isoquinolyl, the 5-isoquinolyl, the 6-isoquinolyl, the 7-isoquinolyl, the 8-isoquinolyl, 2-quinoxalinyl (quinoxanyl), 5-quinoxalinyl (quinoxanyl), 6-quinoxalinyl (quinoxanyl), the 1-carbazyl, the 2-carbazyl, the 3-carbazyl, the 4-carbazyl, the 9-carbazyl, 1-coffee pyridine base, 2-coffee pyridine base, 3-coffee pyridine base, 4-coffee pyridine base, 6-coffee pyridine base, 7-coffee pyridine base, 8-coffee pyridine base, 9-coffee pyridine base, 10-coffee pyridine base, the 1-acridyl, the 2-acridyl, the 3-acridyl, the 4-acridyl, the 9-acridyl, 1, the 7-phenanthrene is coughed up beautiful jade-2-base, 1, the 7-phenanthrene is coughed up beautiful jade-3-base, 1, the 7-phenanthrene is coughed up beautiful jade-4-base, 1, the 7-phenanthrene is coughed up beautiful jade-5-base, 1, the 7-phenanthrene is coughed up beautiful jade-6-base, 1, the 7-phenanthrene is coughed up beautiful jade-8-base, 1, the 7-phenanthrene is coughed up beautiful jade-9-base, 1, the 7-phenanthrene is coughed up beautiful jade-10-base, 1, the 8-phenanthrene is coughed up beautiful jade-2-base, 1, the 8-phenanthrene is coughed up beautiful jade-3-base, 1, the 8-phenanthrene is coughed up beautiful jade-4-base, 1, the 8-phenanthrene is coughed up beautiful jade-5-base, 1, the 8-phenanthrene is coughed up beautiful jade-6-base, 1, the 8-phenanthrene is coughed up beautiful jade-7-base, 1, the 8-phenanthrene is coughed up beautiful jade-9-base, 1, the 8-phenanthrene is coughed up beautiful jade-10-base, 1, the 9-phenanthrene is coughed up beautiful jade-2-base, 1, the 9-phenanthrene is coughed up beautiful jade-3-base, 1, the 9-phenanthrene is coughed up beautiful jade-4-base, 1, the 9-phenanthrene is coughed up beautiful jade-5-base, 1, the 9-phenanthrene is coughed up beautiful jade-6-base, 1, the 9-phenanthrene is coughed up beautiful jade-7-base, 1, the 9-phenanthrene is coughed up beautiful jade-8-base, 1, the 9-phenanthrene is coughed up beautiful jade-10-base, 1, the 10-phenanthrene is coughed up beautiful jade-2-base, 1, the 10-phenanthrene is coughed up beautiful jade-3-base, 1, the 10-phenanthrene is coughed up beautiful jade-4-base, 1, the 10-phenanthrene is coughed up beautiful jade-5-base, 2,9-phenanthrolines-1-base, 2, the 9-phenanthrene is coughed up beautiful jade-3-base, 2, the 9-phenanthrene is coughed up beautiful jade-4-base, 2, the 9-phenanthrene is coughed up beautiful jade-5-base, 2, the 9-phenanthrene is coughed up beautiful jade-6-base, 2, the 9-phenanthrene is coughed up beautiful jade-7-base, 2, the 9-phenanthrene is coughed up beautiful jade-8-base, 2, the 9-phenanthrene is coughed up beautiful jade-10-base, 2, the 8-phenanthrene is coughed up beautiful jade-1-base, 2, the 8-phenanthrene is coughed up beautiful jade-3-base, 2, the 8-phenanthrene is coughed up beautiful jade-4-base, 2, the 8-phenanthrene is coughed up beautiful jade-5-base, 2, the 8-phenanthrene is coughed up beautiful jade-6-base, 2, the 8-phenanthrene is coughed up beautiful jade-7-base, 2, the 8-phenanthrene is coughed up beautiful jade-9-base, 2, the 8-phenanthrene is coughed up beautiful jade-10-base, 2, the 7-phenanthrene is coughed up beautiful jade-1-base, 2, the 7-phenanthrene is coughed up beautiful jade-3-base, 2, the 7-phenanthrene is coughed up beautiful jade-4-base, 2, the 7-phenanthrene is coughed up beautiful jade-5-base, 2, the 7-phenanthrene is coughed up beautiful jade-6-base, 2, the 7-phenanthrene is coughed up beautiful jade-8-base, 2, the 7-phenanthrene is coughed up beautiful jade-9-base, 2, the 7-phenanthrene is coughed up beautiful jade-10-base, the 1-phenazinyl, the 2-phenazinyl, the 1-phenothiazinyl, the 2-phenothiazinyl, the 3-phenothiazinyl, the 4-phenothiazinyl, the lysivane base, the 1-phenoxazinyl, the 2-phenoxazinyl, the 3-phenoxazinyl, the 4-phenoxazinyl, the 10-phenoxazinyl, the 2-oxazolyl, the 4-oxazolyl, the 5-oxazolyl, 2-oxadiazole base, 5-oxadiazole base, 3-furazan base (furazanyl), the 2-thienyl, the 3-thienyl, 2-picoline-1-base, 2-methylpyrrole-3-base, 2-methylpyrrole-4-base, 2-methylpyrrole-5-base, 3-methylpyrrole-1-base, 3-methylpyrrole-2-base, 3-methylpyrrole-4-base, 3-methylpyrrole-5-base, 2-tertiary butyl pyrroles-4-base, 3-(2-phenyl propyl) pyrroles one-1-base, 2-methyl isophthalic acid-indyl, 4-methyl isophthalic acid-indyl, 2-methyl-3-indyl, 4-methyl-3-indyl, the 2-tertiary butyl-1-indyl, the 4-tertiary butyl-1-indyl, the 2-tertiary butyl-3-indyl or the 4-tertiary butyl-3-indyl.
The synthetic method of organic electronic transmission of the present invention and/or hole barrier materials may further comprise the steps:
(1). under the room temperature, will have substituent R
2, R
3, R
2', R
3' 2-bromo-1-methyl phenyl ketone, have substituent R
2, Ar
1, R
2', Ar
1' the bromo aryl or have substituent R
2, Ar
1, R
2', Ar
1' bromo aromatic heterocycle ethyl ketone and pyridine raw material, be that 1: 1 ratio is dissolved in the organic solvent with mol ratio, stir, filter and obtain pyridinium tribromide salt product;
(2). under protection of inert gas, the pyridinium tribromide salt product that step (1) is obtained and has substituent R
1, R
5, R
5' diketone and have a substituent R
4, R
4' phenyl aldehyde, have substituent A r
2, Ar
2' aryl formaldehyde or have substituent A r
2, Ar
2' aryl-heterocyclic formaldehyde, be 2: 1: 2 mixed with mol ratio, and be mixed with the ammonium acetate of catalytic amount, mixture is dissolved in the Glacial acetic acid refluxes then, filter out product, through column chromatography chromatogram or recrystallization, obtain the polyaryl substituted pyridine derivative;
Wherein: R
1, R
2, R
2', R
3, R
3', R
4, R
4', R
5, R
5', Ar
1, Ar
1', Ar
2, Ar
2' definition with the definition one class polyaryl substituted pyridine derivative molecular structure in R
1, R
2, R
2', R
3, R
3', R
4, R
4', R
5, R
5', Ar
1, Ar
1', Ar
2, Ar
2'.
Described organic solvent can be methyl alcohol, ethanol, tetrahydrofuran (THF), methylene dichloride or dioxane etc.
Organic electronic transmission of the present invention and/or hole barrier materials can be used as the electron transfer layer and/or the hole barrier layer material of organic electroluminescence device, be used to prepare organic electroluminescence device, be a kind of extraordinary royal purple light, blue light, green glow, fluorescence, gold-tinted, orange light, ruddiness, near-infrared fluorescent and phosphorescence device, especially blue organic electroluminescence device, and have good stability and long lifetime.The thickness of described electron transfer layer only is 35nm.
Organic electronic transmission of the present invention and/or hole barrier materials also can be used as the organic light emission layer material of organic electroluminescence device.
Described organic electroluminescence device all has very big purposes in organic transistor, organic integration circuit, organic solar batteries, organic laser or organic sensor.
The electron transfer layer of described organic electroluminescence device and/or hole blocking layer can be with being coated with or the method for vacuum steaming degree makes, and the structure of device is: anode/hole transmission layer/organic luminous layer/electron transfer layer/negative electrode.
The preferred implementation of fabricate devices:
The typical structure of OLED device is: substrate/anode/hole transmission layer (HTL)/organic luminous layer/electron transfer layer (ETL)/negative electrode.
Substrate is transparent, can be glass or flexible substrate, and flexible substrate adopts a kind of material in polyester, the poly-phthalimide compounds; Anode layer can adopt inorganic materials or organic conductive polymkeric substance, and inorganic materials is generally tin indium oxide (hereinafter to be referred as ITO).The higher metals of work function such as metal oxide such as zinc oxide, zinc tin oxide or gold, copper, silver, the optimized ITO that is chosen as, organic conductive polymkeric substance are preferably a kind of material in poly-saliva fen/polyvinylbenzenesulfonic acid sodium (hereinafter to be referred as PEDOT:PSS), the polyaniline (hereinafter to be referred as PANI).Cathode layer generally adopts lower metal or a kind of and copper in them, gold or the silver-colored alloys of work function such as lithium, magnesium, calcium, strontium, aluminium or indium, or the electrode layer that alternately forms of above-mentioned metal or alloy and metal fluoride, the present invention is preferably LiF layer and Mg:Ag alloy layer successively; Hole transmission layer generally adopts the tri-arylamine group material, and the present invention is preferably N, N '-two-(1-naphthyl)-N, N '-phenylbenzene-1,1-xenyl-4,4-diamines (NPB); Electron transfer layer is generally a metal-organic complex, close gallium (III) (the following Alq3 that is called for short respectively as three (oxine) aluminium, three (oxine) gallium, (the adjacent amine phenol of salicylidene)-(oxine), Gaq3, Ga (Saph-q)), also can be adjacent phenanthrene and cough up the beautiful jade class, as 4,7-phenylbenzene-1, the adjacent phenanthrene of 10-is coughed up beautiful jade (hereinafter to be referred as Bphen) etc., the polyaryl substituted pyridine derivative of the preferred the present invention's preparation of the present invention has been obtained than the better device effect of foregoing several classical electron transport materials as electron transfer layer; Organic luminous layer generally can adopt small molecule material, can doping fluorescent material or phosphorescent coloring, and the preferred material of main part of the present invention is ADN, TBP, Alq3, Gaq3, Ga (Saph-q).
Can prepare a series of organic electroluminescence device of the present invention in accordance with the following methods:
(1) divides several steps to clean with clean-out system, deionized water and organic solution and have the anodic glass substrate;
(2) hole transmission layer of the method evaporation device by vacuum-evaporation;
(3) continue the luminescent layer of evaporation device again;
(4) electron transfer layer of continuation evaporation device;
(5) method by evaporation or sputter prepares metallic cathode again.
OLED prepares enforcement:
Sheet glass supersound process in commercial clean-out system of ITO transparency conducting layer will be coated with, in deionized water, wash, at acetone: ultrasonic oil removing in the alcohol mixed solvent, under clean environment, be baked to and remove moisture content fully, with UV-light cleaning machine irradiation 10 minutes, and with low energy positively charged ion bundle bombarded surface.
The above-mentioned anodic glass substrate that has is placed in the vacuum chamber, be evacuated to 1 * 10
-5～9 * 10
-3Pa, first evaporation CuPc15nm on above-mentioned anode tunic continues evaporation NPB as hole transmission layer, and evaporation speed is that 0.1nm/s. evaporation thickness is 75nm;
On hole transmission layer, continue evaporation one deck and be doped with the luminescent layer of the TBP of compd A DN as device, the evaporation speed ratio of ADN and TBP is 1: 100, and the doping content of ADN in TBP is 1wt%, the total speed of its evaporation is 0.1nm/s, and the evaporation total film thickness is 30nm;
Continue the electron transfer layer of the prepared material of evaporation one deck the present invention as device again, its evaporation speed is 0.1nm/s, and the evaporation total film thickness is 35nm.
At last, evaporation LiF layer and Mg:Ag alloy layer are as the cathode layer of device successively on above-mentioned electron transfer layer, and wherein the thickness of LiF layer is 0.5nm, and the evaporation speed of Mg:Ag alloy layer is 2.0～3.0nm/s, and thickness is 100nm.
The present invention adopts easy method to synthesize a class polyaryl substituted pyridine derivative, and makes electric transmission and/or hole barrier materials has been made blue-light device with this polyaryl substituted pyridine derivative.This type of polyaryl substituted pyridine derivative has high IP/EA value, and has high quantum yield, has high brightness, is electron transport material and/or hole barrier materials that a class has the high hole blocking capability; Have high Tg temperature, can effectively suppress the crystalline condition of material, improve film-forming properties, improve the performance of device.With respect to PBD, the material conjugate length that contains among the present invention increases, and fusing point greatly improves; The most important thing is that electron transport ability significantly strengthens, thereby improved the over-all properties of electroluminescent device.When being used for organic electroluminescence device, obtained gratifying result aspect the efficient of the device of making under brightness, current density and high current density, wherein a kind of over-all properties obviously is better than the BCP of present widespread use, thereby has obtained a kind of electric transmission of excellent property and/or the organic electroluminescence device of hole barrier materials.
In order to understand the content of patent of the present invention better, will further specify technical scheme of the present invention by specific embodiment below, but be not limited thereto.
Embodiment
Embodiment 1.1, the preparation of two (2-(4,6-phenylbenzene-5-the 5-flumethiazine)) benzene (BDTPB) of 4-
The first step: getting mol ratio and be 1 2-bromo-1-(4-trifluoromethyl) ethyl ketone and pyridine is raw material, at room temperature stirs 10 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 90%;
Second step: under the condition of nitrogen protection; with the first step product; benzene diethyl ketone and phenyl aldehyde (mol ratio is 2: 1: 2) are added in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 50%.
m/z：672.20(100.0％)，673.20(46.2％)，674.21(10.2％)，675.21(1.5％)。
The OLED device preparation of compd B DTPB
Device architecture:
ITO/CuPc(15nm)/NPB(75nm)/ADN:TBP(30nm)/
BDTPB(35nm)/LiF(0.5nm)/MgAg(10∶1?100nm)
The device performance index is as follows:
Tristimulus coordinates: (X=0.15, Y=0.22);
Play bright voltage: 4.2V;
High-high brightness: 19800cd/m
2(12V);
Luminous efficiency: 4.5cd/A.
Embodiment 2.1, the preparation of two (2-(6-phenyl-4-p-methylphenyl-5-5-flumethiazine)) benzene (BPTTPB) of 4-
The first step: getting mol ratio and be 1 2-bromo-1-(4-trifluoromethyl) ethyl ketone and pyridine is raw material, at room temperature stirs 8 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 90%;
Second step: under the condition of nitrogen protection; with the first step product; benzene diethyl ketone and p-tolyl aldehyde (mol ratio is 2: 1: 2) are added in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 55%.
m/z：700.23(100.0％)，701.23(48.3％)，702.24(11.2％)，703.24(1.8％)。
Embodiment 3.6,6 '-(1, the 4-phenylene) two (2,4-phenylbenzene pyridine nitrile) preparation (PBDNN)
The first step: getting mol ratio and be 1 4-(2-bromo ethanoyl) benzene nitrile and pyridine is raw material, at room temperature stirs 7 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 85%;
Second step: under the condition of nitrogen protection; with the first step product; benzene diethyl ketone and phenyl aldehyde (mol ratio is 2: 1: 2) are added in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 60%.
m/z：586.22(100.0％)，587.22(45.7％)，588.22(10.7％)，589.23(1.5％)，587.21(1.5％)。
The OLED device preparation of Compound P BDNN
Device architecture:
ITO/CuPc(15nm)/NPB(75nm)/ADN:TBP(30nm)/
PBDNN(35nm)/LiF(0.5nm)/MgAg(10∶1?100nm)
The device performance index is as follows:
Tristimulus coordinates: (X=0.15, Y=0.22);
Play bright voltage: 4.0V;
High-high brightness: 19500cd/m
2(12V);
Luminous efficiency: 4.2cd/A.
Embodiment 4.6,6 '-(1, the 4-phenylene) two (4-(4-tert.-butylbenzene)-2-phenylpyridine nitrile) preparation (PBBPNN)
The first step: getting mol ratio and be 1 4-(2-bromo ethanoyl) benzene nitrile and pyridine is raw material, at room temperature stirs 6 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 85%;
Second step: under the condition of nitrogen protection; with the first step product; benzene diethyl ketone and p-t-Butylbenzaldehyde (mol ratio is 2: 1: 2) are added in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 50%.
m/z：698.34(100.0％)，699.34(55.6％)，700.35(14.6％)，701.35(2.6％)。
Embodiment 5.6,6 '-(1, the 4-phenylene) two (2-phenyl-4-p-methylphenyl pyridine diethyl ester) preparation (PBPTNN)
The first step: getting mol ratio and be 1 4-(2-bromo ethanoyl) ethyl benzoate and pyridine is raw material, at room temperature stirs 8 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 95%;
Second step: under the condition of nitrogen protection; with the first step product; benzene diethyl ketone and p-tolyl aldehyde (mol ratio is 2: 1: 2) are added in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 55%.
m/z：708.30(100.0％)，709.30(52.8％)，710.31(13.5％)，711.31(2.7％)，710.30(1.2％)。
Embodiment 6.6,6 '-(1, the 4-phenylene) two (2,4-phenylbenzene pyridine-3,5-dintrile) preparation (PBDPD)
The first step: getting mol ratio and be 1 4-(2-acetyl bromide) benzene nitrile and pyridine is raw material, at room temperature stirs 11 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 90%;
Second step: under the condition of nitrogen protection; with the first step product, ω, ω '-dicyano adds in the three-necked bottle benzene diethyl ketone and phenyl aldehyde (mol ratio is 2: 1: 2); add an amount of Glacial acetic acid and ammonium acetate then; the powerful stirring, keeping temperature is 120 ℃～140 ℃, refluxes 24 hours; filter out product; through column chromatography chromatogram or recrystallization, obtain target product with high purity, productive rate about 45%.
m/z：636.21(100.0％)，637.21(47.9％)，638.21(12.1％)，637.20(2.2％)，639.22(1.7％)。
The OLED device preparation of Compound P BDPD
Device architecture:
ITO/CuPc(15nm)/NPB(75nm)/ADN:TBP(30nm)/
PBDPD(35nm)/LiF(0.5nm)/MgAg(10∶1?100nm)
The device performance index is as follows:
Tristimulus coordinates: (X=0.15, Y=0.22);
Play bright voltage: 3.8V;
High-high brightness: 19000cd/m
2(12V);
Luminous efficiency: 4.6cd/A.
Embodiment 7.6,6 '-(1, the 4-phenylene) two (4-(4-tert.-butylbenzene)-2-phenylpyridine-3,5-dintrile) preparation (PBBPD)
The first step: getting mol ratio and be 1 4-(2-acetyl bromide) benzene nitrile and pyridine is raw material, at room temperature stirs 12 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 90%;
Second step: under the condition of nitrogen protection; with the first step product, ω, ω '-dicyano adds in the three-necked bottle benzene diethyl ketone p-t-Butylbenzaldehyde (mol ratio is 2: 1: 2); add an amount of Glacial acetic acid and ammonium acetate then; the powerful stirring, keeping temperature is 120 ℃～140 ℃, refluxes 24 hours; filter out product; through column chromatography chromatogram or recrystallization, obtain target product with high purity, productive rate about 50%.
m/z：748.33(100.0％)，749.33(58.5％)，750.34(15.8％)，751.34(3.2％)，750.33(1.3％)。
Embodiment 8.1, the preparation of two (2-(4-(2-furyl)-6-phenyl-5-5-flumethiazine)) benzene (BFPTPB) of 4-
The first step: getting mol ratio and be 1 2-bromo-1-(4-trifluoromethyl) ethyl ketone and pyridine is raw material, at room temperature stirs 12 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 90%;
Second step: under the condition of nitrogen protection; with the first step product; benzene diethyl ketone and 4-(2-furyl) phenyl aldehyde (mol ratio is 2: 1: 2) are added in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 48%.
m/z：652.16(100.0％)，653.16(42.2％)，654.17(8.4％)，655.17(1.3％)。
The OLED device preparation of compd B FPTPB
Device architecture:
ITO/CuPc(15nm)/NPB(75nm)/ADN:TBP(30nm)/
BFPTPB(35nm)/LiF(0.5nm)/MgAg(10∶1?100nm)
The device performance index is as follows:
Tristimulus coordinates: (X=0.15, Y=0.22);
Play bright voltage: 3.9V;
High-high brightness: 19000cd/m
2(12V);
Luminous efficiency: 4.0cd/A.
Embodiment 9.1, the preparation of two (2-(6-phenyl-4-p-methylphenyl-5-5-flumethiazine)) benzene (BPTPB) of 3-
The first step: get mol ratio and be 1 2-bromo-1-(4-trifluoromethyl) ethyl ketone, pyridine is a raw material, at room temperature stirs 7 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 90%;
Second step: under the condition of nitrogen protection; with the first step product; between benzene diethyl ketone and p-tolyl aldehyde (mol ratio is 2: 1: 2) add in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 60%.
m/z：700.23(100.0％)，701.23(48.3％)，702.24(11.2％)，703.24(1.8％)。
Embodiment 10.1, the preparation of two (2-(4-(4-is to anisole)-6-phenyl-5-5-flumethiazine)) benzene (BMPTPB) of 3-
The first step: getting mol ratio and be 1 2-bromo-1-(4-trifluoromethyl) ethyl ketone and pyridine is raw material, at room temperature stirs 8 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 95%;
Second step: under the condition of nitrogen protection; with the first step product; between benzene diethyl ketone and aubepine (mol ratio is 2: 1: 2) add in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 55%.
m/z：732.22(100.0％)，733.22(48.3％)，734.23(11.7％)，735.23(1.9％)。
Embodiment 11.6,6 '-(1, the 3-phenyl) two (2-phenyl-4-p-methylphenyl pyridine nitrile) preparation (PBTNN)
The first step: getting mol ratio and be 1 4-(2-bromo ethanoyl) benzene nitrile and pyridine is raw material, at room temperature stirs 9 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 90%;
Second step: under the condition of nitrogen protection; with the first step product; between benzene diethyl ketone and p-tolyl aldehyde (mol ratio is 2: 1: 2) add in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 45%.
m/z：614.25(100.0％)，615.25(47.9％)，616.25(11.8％)，617.26(1.7％)，61?5.24(1.5％)。
The OLED device preparation of Compound P BTNN
Device architecture:
ITO/CuPc(15nm)/NPB(75nm)/ADN:TBP(30nm)/
PBTNN(35nm)/LiF(0.5nm)/MgAg(10∶1?100nm)
The device performance index is as follows:
Tristimulus coordinates: (X=0.15, Y=0.22);
Play bright voltage: 4.2V;
High-high brightness: 19800cd/m
2(12V);
Luminous efficiency: 4.5cd/A.
Embodiment 12.6, the two (preparations of 4-(4-is to tert.-butylbenzene)-2 phenylpyridine nitrile (PBTPNN) of 6-(1, the 3-phenylene)
The first step: getting mol ratio and be 1 4-(2-bromo ethanoyl) benzene nitrile and pyridine is raw material, at room temperature stirs 8 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 85%;
Second step: under the condition of nitrogen protection; with the first step product; between benzene diethyl ketone and p-t-Butylbenzaldehyde (mol ratio is 2: 1: 2) add in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 55%.
m/z：698.34(100.0％)，699.34(55.6％)，700.35(14.6％)，701.35(2.6％)。
Embodiment 13.6,6 '-(1, the 3-phenylene) two (4-(4-is to anisole)-2 phenylpyridine diethyl ester) preparation (PBMPNN)
The first step: getting mol ratio and be 1 4-(2-bromo ethanoyl) ethyl benzoate and pyridine is raw material, at room temperature stirs 10 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 95%;
Second step: under the condition of nitrogen protection; with the first step product; between benzene diethyl ketone and aubepine (mol ratio is 2: 1: 2) add in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 60%.
m/z：740.29(100.0％)，741.29(53.3％)，742.30(13.6％)，743.30(2.9％)，742.29(1.6％)。
Embodiment 14.1, two (2-(6-phenylene-4-p-methylphenyl-3,5-bis trifluoromethyl pyridine the benzene)) preparations (PTTPBN) of 3-
The first step: getting mol ratio and be 1 2-bromo-1-(4-trifluoromethyl) ethyl ketone and pyridine is raw material, at room temperature stirs 12 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 90%;
Second step: under the condition of nitrogen protection; with the first step product, ω, benzene diethyl ketone and p-tolyl aldehyde between ω '-two trifluoromethyl (mol ratio is 2: 1: 2) add in the three-necked bottle; add an amount of Glacial acetic acid and ammonium acetate then; the powerful stirring, keeping temperature is 120 ℃～140 ℃, refluxes 24 hours; filter out product; through column chromatography chromatogram or recrystallization, obtain target product with high purity, productive rate about 60%.
m/z：722.19(100.0％)，723.19(49.1％)，724.20(11.2％)，725.20(1.7％)。
The OLED device preparation of Compound P TTPBN
Device architecture:
ITO/CuPc(15nm)/NPB(75nm)/ADN:TBP(30nm)/
PTTPBN(35nm)/LiF(0.5nm)/MgAg(10∶1?100nm)。
The device performance index is as follows:
Tristimulus coordinates: (X=0.15, Y=0.22);
Play bright voltage: 4.4V;
High-high brightness: 20050cd/m
2(12V);
Luminous efficiency: 4.2cd/A.
Embodiment 15.6,6 '-(1, the 3-phenylene) two (4-(4-is to tert.-butylbenzene)-2-phenylpyridine-3,5-dintrile)) (PBPPD) preparation
The first step: getting mol ratio and be 1 4-(2-acetyl bromide) benzene nitrile and pyridine is raw material, at room temperature stirs 12 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 90%;
Second step: under the condition of nitrogen protection; with the first step product, ω, benzene diethyl ketone and p-t-Butylbenzaldehyde between ω '-dicyano (mol ratio is 2: 1: 2) add in the three-necked bottle; add an amount of Glacial acetic acid and ammonium acetate then; the powerful stirring, keeping temperature is 120 ℃～140 ℃, refluxes 24 hours; filter out product; through column chromatography chromatogram or recrystallization, obtain target product with high purity, productive rate about 60%.
m/z：748.33(100.0％)，749.33(58.5％)，750.34(15.8％)，751.34(3.2％)，750.33(1.3％)。
Embodiment 16.1, the preparation of two (2-(4-(3-furyl)-6-phenyl-5-5-flumethiazine)) benzene (BFPTPB) of 3-
The first step: get mol ratio and be 1 2-bromo-1-(4-trifluoromethyl) ethyl ketone, pyridine is a raw material, at room temperature stirs 10 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 85%;
Second step: under the condition of nitrogen protection; with the first step product; between benzene diethyl ketone and 4-(3-furyl) phenyl aldehyde (mol ratio is 2: 1: 2) add in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 50%.
m/z：652.16(100.0％)，653.16(42.2％)，654.17(8.4％)，655.17(1.3％)。
Embodiment 17.1, the preparation of two (2-(4-(4-anisole)-6-phenyl-5-5-flumethiazine)) benzene (PPTPB) of 2-
The first step: getting mol ratio and be 1 2-bromo-1-(4-trifluoromethyl) ethyl ketone and pyridine is raw material, at room temperature stirs 6 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 85%;
Second step: under the condition of nitrogen protection; with the first step product; adjacent benzene diethyl ketone and aubepine (mol ratio is 2: 1: 2) add in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 45%.
m/z：732.22(100.0％)，733.22(48.3％)，734.23(11.7％)，735.23(1.9％)。
Embodiment 18.4, the 4 '-(preparation of 6,6 '-(1, the 2-phenylene)-two (2-phenyl-3-trifluoromethyl-pyridine-6,4-yl) hexichol nitrile (PBTPD)
The first step: get mol ratio and be 1 2-bromo-1-(4-trifluoromethyl) ethyl ketone, pyridine is a raw material, at room temperature stirs 8 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 80%;
Second step: under the condition of nitrogen protection; with the first step product; adjacent benzene diethyl ketone and cyanobenzaldehyde (mol ratio is 2: 1: 2) added in the three-necked bottle adds an amount of Glacial acetic acid and ammonium acetate, the powerful stirring then; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 60%.
m/z：722.19(100.0％)，723.19(49.1％)，724.20(11.2％)，725.20(1.7％)。
Embodiment 19.6,6 '-(1, the 2-phenylene)-two (2,4-phenylbenzene pyridine nitrile) preparation (PBDNT)
The first step: get mol ratio and be 1 4-(2-bromo ethanoyl) benzene nitrile, pyridine is a raw material, at room temperature stirs 10 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 75%;
Second step: under the condition of nitrogen protection; with the first step product; adjacent benzene diethyl ketone and phenyl aldehyde (mol ratio is 2: 1: 2) add in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 65%.
m/z：586.22(100.0％)，587.22(45.7％)，588.22(10.7％)，589.23(1.5％)，587.21(1.5％)。
Embodiment 20.6,6 '-(1, the 2-phenylene)-two (4-(4-cyano group benzene)-2,4-phenylbenzene pyridine nitrile) preparation (PBCPN)
The first step: get mol ratio and be 1 4-(2-bromo ethanoyl) benzene nitrile, pyridine is a raw material, at room temperature stirs 8 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 80%;
Second step: under the condition of nitrogen protection; with the first step product; adjacent benzene diethyl ketone and cyanobenzaldehyde (mol ratio is 2: 1: 2) added in the three-necked bottle adds an amount of Glacial acetic acid and ammonium acetate, the powerful stirring then; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 55%.
m/z：698.34(100.0％)，699.34(55.6％)，700.35(14.6％)，701.35(2.6％)。
The OLED device preparation of Compound P BCPN
Device architecture:
ITO/CuPc(15nm)/NPB(75nm)/ADN:TBP(30nm)/
PBCPN(35nm)/LiF(0.5nm)/MgAg(10∶1?100nm)。
The device performance index is as follows:
Tristimulus coordinates: (X=0.15, Y=0.22);
Play bright voltage: 4.5V;
High-high brightness: 20020cd/m
2(12V);
Luminous efficiency: 4.8cd/A.
Embodiment 21.6,6 '-(1, the 2-phenylene) two (2,4-phenylbenzene-2-phenylpyridine diethyl ester) preparation (PBNN)
The first step: getting mol ratio and be 1 4-(2-bromo ethanoyl) ethyl benzoate and pyridine is raw material, at room temperature stirs 10 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 75%;
Second step: under the condition of nitrogen protection; with the first step product; adjacent benzene diethyl ketone and phenyl aldehyde (mol ratio is 2: 1: 2) add in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 60%.
m/z：680.27(100.0％)，681.27(50.3％)，682.27(13.3％)，683.28(2.4％)。
Embodiment 22.6,6 '-(1, the 2-phenylene) two (2,4-phenylbenzene pyridine-3,5-dintrile) preparation (PBDDN)
The first step: getting mol ratio and be 1 4-(2-acetyl bromide) benzene nitrile and pyridine is raw material, at room temperature stirs 11 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 90%;
Second step: under the condition of nitrogen protection; with the first step product, ω, adjacent benzene diethyl ketone of ω '-dicyano and phenyl aldehyde (mol ratio is 2: 1: 2) add in the three-necked bottle; add an amount of Glacial acetic acid and ammonium acetate then; the powerful stirring, keeping temperature is 120 ℃～140 ℃, refluxes 24 hours; filter out product; through column chromatography chromatogram or recrystallization, obtain target product with high purity, productive rate about 45%.
m/z：636.21(100.0％)，637.21(47.9％)，638.21(12.1％)，637.20(2.2％)，639.22(1.7％)。
Embodiment 23.6,6 '-(1, the 2-phenylene) two (4-(4-tert.-butylbenzene)-2-phenylpyridine-3,5-dintrile) preparation (PTPPD)
The first step: getting mol ratio and be 1 4-(2-acetyl bromide) benzene nitrile and pyridine is raw material, at room temperature stirs 12 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 90%;
Second step: under the condition of nitrogen protection; with the first step product, ω, adjacent benzene diethyl ketone of ω '-dicyano and p-t-Butylbenzaldehyde (mol ratio is 2: 1: 2) add in the three-necked bottle; add an amount of Glacial acetic acid and ammonium acetate then; the powerful stirring, keeping temperature is 120 ℃～140 ℃, refluxes 24 hours; filter out product; through column chromatography chromatogram or recrystallization, obtain target product with high purity, productive rate about 55%.
m/z：748.33(100.0％)，749.33(58.5％)，750.34(15.8％)，751.34?(3.2％)，750.33(1.3％)。
The OLED device preparation of Compound P TPPD
Device architecture:
ITO/CuPc(15nm)/NPB(75nm)/ADN:TBP(30nm)/
PTPPD(35nm)/LiF(0.5nm)/MgAg(10∶1?100nm)
The device performance index is as follows:
Tristimulus coordinates: (X=0.15, Y=0.22);
Play bright voltage: 3.8V;
High-high brightness: 20000cd/m
2(12V);
Luminous efficiency: 4.8cd/A.
Embodiment 24.1, the preparation of two (2-(4-(3-furyl)-6-phenyl-5-5-flumethiazine)) benzene (BFTPB) of 2-
The first step: getting mol ratio and be 1 2-bromo-1-(4-trifluoromethyl) ethyl ketone and pyridine is raw material, at room temperature stirs 12 hours, filters, and massive laundering promptly gets corresponding pyridine bromine salt, productive rate about 85%;
Second step: under the condition of nitrogen protection; with the first step product; adjacent benzene diethyl ketone and 4-(3-furyl) phenyl aldehyde (mol ratio is 2: 1: 2) add in the three-necked bottle, add an amount of Glacial acetic acid and ammonium acetate then, the powerful stirring; keeping temperature is 120 ℃～140 ℃; refluxed 24 hours, and filtered out product, through column chromatography chromatogram or recrystallization; obtain target product with high purity, productive rate about 65%.
m/z：652.16(100.0％)，653.16(42.2％)，654.17(8.4％)，655.17(1.3％)。
The OLED device preparation of compd B FTPB
Device architecture:
ITO/CuPc(15nm)/NPB(75nm)/ADN:TBP(30nm)/
BFTPB(35nm)/LiF(0.5nm)/MgAg(10∶1?100nm)。
The device performance index is as follows:
Tristimulus coordinates: (X=0.15, Y=0.22);
Play bright voltage: 4.5V;
High-high brightness: 20020cd/m
2(12V);
Luminous efficiency: 4.8cd/A.
More than listed embodiment all can be used in organic transistor, organic integration circuit, organic solar batteries, organic laser or the organic sensor.
Although describe the present invention in conjunction with the preferred embodiments, but the present invention is not limited to the foregoing description, should be appreciated that under the guiding of the present invention's design, those skilled in the art can carry out various modifications and improvement, and claims have been summarized scope of the present invention.
Claims (8)
1. an organic electronic transmits and/or hole barrier materials, it is characterized in that, this organic electronic transmission and/or hole barrier materials are the polyaryl substituted pyridine derivatives, and it has following molecular structure:
Wherein:
R
1, R
3, R
3', R
4, R
4' substituting group can be identical or different, independently is selected from hydrogen respectively, methyl, ethyl, propyl group, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, cyclopentyl, cyclohexyl, alkoxyl group with 1 to 8 carbon atom, phenyl, the 1-naphthyl, the 2-naphthyl, the 1-anthryl, the 2-anthryl, the 9-anthryl, the 4-xenyl, p-methylphenyl, to tert-butyl-phenyl, aryloxy with 6 to 14 annular atomses, the 1-pyrryl, the 2-pyrryl, the 3-pyrryl, pyridyl, the 2-pyridyl, the 3-pyridyl, the 4-pyridyl, the 2-quinolyl, the 3-quinolyl, the 4-quinolyl, the 5-quinolyl, the 6-quinolyl, the 7-quinolyl, the 8-quinolyl, the 1-carbazyl, the 2-carbazyl, the 3-carbazyl, a kind of in 4-carbazyl or the 9-carbazyl;
Described R
1, R
3, R
3', R
4, R
4' in the alkoxyl group with 1 to 8 carbon atom be by-group that OR represents, wherein the group represented of R is an alkyl, and alkyl is methyl, ethyl, propyl group, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl, n-heptyl or n-octyl;
Described R
1, R
3, R
3', R
4, R
4' in have 6 to 14 annular atomses aryloxy be by-group that OAr represents, wherein the group represented of Ar is an aromatic group, and aromatic group is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 4-xenyl, p-methylphenyl or to tert-butyl-phenyl;
R
2, R
2', R
5, R
5' substituting group can be identical or different, independently is selected from a kind of in fluoro methyl, cyano group, methoxycarbonyl or the ethoxycarbonyl respectively;
Ar
1, Ar
1', Ar
2, Ar
2' substituting group can be identical or different, independently is selected from a kind of in 1-pyrryl, 2-pyrryl, 3-pyrryl, pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, 3-furyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-carbazyl, 2-carbazyl, 3-carbazyl, 4-carbazyl or the 9-carbazyl respectively.
2. organic electronic transmission according to claim 1 and/or hole barrier materials is characterized in that: described R
2, R
2', R
5, R
5' in the fluoro methyl be the methyl that a fluorine, difluoro or trifluoro replace.
3. the synthetic method of organic electronic according to claim 1 and 2 transmission and/or hole barrier materials, it is characterized in that: described synthetic method may further comprise the steps:
(1). will have substituent R
2, R
3, R
2', R
3' 2-bromo-1-methyl phenyl ketone, have substituent R
2, Ar
1, R
2', Ar
1' the bromo aryl or have substituent R
2, Ar
1, R
2', Ar
1' bromo aromatic heterocycle ethyl ketone and pyridine raw material, be that 1: 1 ratio is dissolved in the organic solvent with mol ratio, stir, filter and obtain pyridinium tribromide salt product;
(2). under protection of inert gas, the pyridinium tribromide salt product that step (1) is obtained and has substituent R
1, R
5, R
5' diketone and have a substituent R
4, R
4' phenyl aldehyde, have substituent A r
2, Ar
2' aryl formaldehyde or have substituent A r
2, Ar
2' aryl-heterocyclic formaldehyde, be 2: 1: 2 mixed with mol ratio, and be mixed with the ammonium acetate of catalytic amount, mixture is dissolved in the Glacial acetic acid refluxes then, filter out product, through column chromatography chromatogram or recrystallization, obtain the polyaryl substituted pyridine derivative;
Wherein: R
1, R
2, R
2', R
3, R
3', R
4, R
4', R
5, R
5', Ar
1, Ar
1', Ar
2, Ar
2' definition described with claim 1 or 2.
4. method according to claim 3 is characterized in that: described organic solvent is methyl alcohol, ethanol, tetrahydrofuran (THF), methylene dichloride or dioxane.
5. the purposes of organic electronic according to claim 1 and 2 transmission and/or hole barrier materials, it is characterized in that: described organic electronic transmission and/or hole barrier materials are used to prepare organic electroluminescence device as the electron transfer layer and/or the hole barrier layer material of organic electroluminescence device.
6. purposes according to claim 5 is characterized in that: described organic electronic transmission and/or hole barrier materials are as the organic light emission layer material of organic electroluminescence device.
7. purposes according to claim 5, it is characterized in that: described organic electroluminescence device comprises negative electrode, anode and organic thin film layer, at least comprise organic luminous layer in the organic thin film layer between negative electrode and anode, and in the organic thin film layer at least one deck comprise the described polyaryl substituted pyridine derivative of claim 1.
8. according to claim 5,6 or 7 described purposes, it is characterized in that: described organic electroluminescence device can be used in organic transistor, organic integration circuit, organic solar batteries, organic laser or the organic sensor.
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| CN1833470A (en) * | 2003-07-31 | 2006-09-13 | 三菱化学株式会社 | Compound, charge transporting material and organic electroluminescent element |
| CN1947466A (en) * | 2004-04-28 | 2007-04-11 | 株式会社半导体能源研究所 | Light emitting device, its manufacturing method, and light emitting device using it |
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