CN112442023A - 一种杂环衍生物及其有机电致发光器件 - Google Patents
一种杂环衍生物及其有机电致发光器件 Download PDFInfo
- Publication number
- CN112442023A CN112442023A CN202011377608.8A CN202011377608A CN112442023A CN 112442023 A CN112442023 A CN 112442023A CN 202011377608 A CN202011377608 A CN 202011377608A CN 112442023 A CN112442023 A CN 112442023A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- group
- compound
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 31
- -1 triarylamine compound Chemical class 0.000 claims abstract description 62
- 230000005525 hole transport Effects 0.000 claims abstract description 23
- 239000012044 organic layer Substances 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 24
- 229910052805 deuterium Inorganic materials 0.000 claims description 24
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 125000005549 heteroarylene group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 19
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 19
- 125000000732 arylene group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000003944 tolyl group Chemical group 0.000 claims description 8
- 125000005580 triphenylene group Chemical group 0.000 claims description 8
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 7
- 125000005567 fluorenylene group Chemical group 0.000 claims description 7
- 125000006836 terphenylene group Chemical group 0.000 claims description 7
- 125000004957 naphthylene group Chemical group 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 125000001725 pyrenyl group Chemical group 0.000 claims description 5
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 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 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 3
- 125000005428 anthryl 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 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000005628 tolylene group Chemical group 0.000 claims description 2
- 125000001294 (C1-C30) cycloalkyl group Chemical group 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- 125000005593 norbornanyl group Chemical group 0.000 claims 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 66
- 230000000903 blocking effect Effects 0.000 abstract description 35
- 239000000969 carrier Substances 0.000 abstract description 10
- 238000010791 quenching Methods 0.000 abstract description 3
- 230000000171 quenching effect Effects 0.000 abstract description 3
- 230000006798 recombination Effects 0.000 abstract description 3
- 238000005215 recombination Methods 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 94
- 150000001875 compounds Chemical class 0.000 description 84
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 238000004128 high performance liquid chromatography Methods 0.000 description 34
- 239000007787 solid Substances 0.000 description 34
- 238000001819 mass spectrum Methods 0.000 description 31
- 238000002360 preparation method Methods 0.000 description 31
- 238000002347 injection Methods 0.000 description 27
- 239000007924 injection Substances 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 26
- 238000001704 evaporation Methods 0.000 description 25
- 238000001514 detection method Methods 0.000 description 24
- 238000000034 method Methods 0.000 description 23
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 16
- 239000002346 layers by function Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 14
- BBVQDWDBTWSGHQ-UHFFFAOYSA-N 2-chloro-1,3-benzoxazole Chemical compound C1=CC=C2OC(Cl)=NC2=C1 BBVQDWDBTWSGHQ-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- 229940125904 compound 1 Drugs 0.000 description 12
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 11
- MNBDZJINQUZDFP-UHFFFAOYSA-N 2-bromospiro[fluorene-9,9'-xanthene] Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11C2=CC=CC=C2C2=CC=C(Br)C=C21 MNBDZJINQUZDFP-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N deuterated chloroform Substances [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 239000011368 organic material Substances 0.000 description 7
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 5
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 4
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 4
- DGLBXGSXRRICJF-UHFFFAOYSA-N 3-bromospiro[fluorene-9,9'-xanthene] Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C21C1=CC=CC=C1C1=CC(Br)=CC=C21 DGLBXGSXRRICJF-UHFFFAOYSA-N 0.000 description 4
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 229940126208 compound 22 Drugs 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 3
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 3
- VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 description 3
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 3
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 3
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 3
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 3
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 229940127204 compound 29 Drugs 0.000 description 3
- 229940125807 compound 37 Drugs 0.000 description 3
- 229940125936 compound 42 Drugs 0.000 description 3
- 229940127113 compound 57 Drugs 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- DYGBNAYFDZEYBA-UHFFFAOYSA-N n-(cyclopropylmethyl)-2-[4-(4-methoxybenzoyl)piperidin-1-yl]-n-[(4-oxo-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-2-yl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(CC(=O)N(CC2CC2)CC=2NC(=O)C=3COCCC=3N=2)CC1 DYGBNAYFDZEYBA-UHFFFAOYSA-N 0.000 description 3
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical group OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 2
- AIJBNWBZEZTIOX-UHFFFAOYSA-N (7-chloro-9,9-dimethylfluoren-2-yl)boronic acid Chemical compound C1=C(B(O)O)C=C2C(C)(C)C3=CC(Cl)=CC=C3C2=C1 AIJBNWBZEZTIOX-UHFFFAOYSA-N 0.000 description 2
- MQRCTQVBZYBPQE-UHFFFAOYSA-N 189363-47-1 Chemical compound C1=CC=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC(=CC=C1C1=CC=C(C=C13)N(C=1C=CC=CC=1)C=1C=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MQRCTQVBZYBPQE-UHFFFAOYSA-N 0.000 description 2
- KFRPZFMLHKXSKI-UHFFFAOYSA-N 2'-bromo-10-phenylspiro[acridine-9,9'-fluorene] Chemical compound BrC1=CC=2C3(C4=CC=CC=C4C=2C=C1)C1=CC=CC=C1N(C=1C=CC=CC=13)C1=CC=CC=C1 KFRPZFMLHKXSKI-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 2
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 2
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 2
- YWKKLBATUCJUHI-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C1=CC=CC=C1 YWKKLBATUCJUHI-UHFFFAOYSA-N 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- SCZWJXTUYYSKGF-UHFFFAOYSA-N 5,12-dimethylquinolino[2,3-b]acridine-7,14-dione Chemical compound CN1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3N(C)C1=C2 SCZWJXTUYYSKGF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- JMYLBKPHIHRJDY-UHFFFAOYSA-N [3-(3-chlorophenyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=C(Cl)C=CC=2)=C1 JMYLBKPHIHRJDY-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000001555 benzenes Chemical group 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- XLGLMVCAOMQNJT-UHFFFAOYSA-N boric acid;chlorobenzene Chemical compound OB(O)O.ClC1=CC=CC=C1 XLGLMVCAOMQNJT-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical class C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000001924 cycloalkanes Chemical class 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910001092 metal group alloy Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- OKPMSRGLGBBULD-UHFFFAOYSA-N n,n-diphenyl-9,9'-spirobi[fluorene]-1-amine Chemical compound C1=CC=CC=C1N(C=1C=2C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC=CC=C3C=2C=CC=1)C1=CC=CC=C1 OKPMSRGLGBBULD-UHFFFAOYSA-N 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000005041 phenanthrolines Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- DYVJQLYYHMZIIU-UHFFFAOYSA-N (3-chloro-5-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=CC(C#N)=C1 DYVJQLYYHMZIIU-UHFFFAOYSA-N 0.000 description 1
- CAYQIZIAYYNFCS-RHQRLBAQSA-N (4-chloro-2,3,5,6-tetradeuteriophenyl)boronic acid Chemical compound [2H]C1=C([2H])C(B(O)O)=C([2H])C([2H])=C1Cl CAYQIZIAYYNFCS-RHQRLBAQSA-N 0.000 description 1
- ZKSSVXQGTJXFPO-UHFFFAOYSA-N (6-chloronaphthalen-2-yl)boronic acid Chemical compound C1=C(Cl)C=CC2=CC(B(O)O)=CC=C21 ZKSSVXQGTJXFPO-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- DZHFFMWJXJBBRG-UHFFFAOYSA-N 1-bromo-3,5-dichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Br)=C1 DZHFFMWJXJBBRG-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- RABBMOYULJIAFU-UHFFFAOYSA-N 1h-pyrrole;thiophene Chemical class C=1C=CNC=1.C=1C=CSC=1 RABBMOYULJIAFU-UHFFFAOYSA-N 0.000 description 1
- VFMUXPQZKOKPOF-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethyl-21,23-dihydroporphyrin platinum Chemical compound [Pt].CCc1c(CC)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(CC)c5CC)c(CC)c4CC)c(CC)c3CC VFMUXPQZKOKPOF-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 1
- GEYFXQNOTPBYPC-UHFFFAOYSA-N 2-(4-chlorophenyl)-1,3-benzothiazole Chemical compound C1=CC(Cl)=CC=C1C1=NC2=CC=CC=C2S1 GEYFXQNOTPBYPC-UHFFFAOYSA-N 0.000 description 1
- ZHMIODDNZRIENW-UHFFFAOYSA-N 2-Methyl-3-(2-methylpropyl)pyrazine Chemical compound CC(C)CC1=NC=CN=C1C ZHMIODDNZRIENW-UHFFFAOYSA-N 0.000 description 1
- YLYPIBBGWLKELC-RMKNXTFCSA-N 2-[2-[(e)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC(=C(C#N)C#N)C=C(C)O1 YLYPIBBGWLKELC-RMKNXTFCSA-N 0.000 description 1
- YIRRVMGAKFESLR-UHFFFAOYSA-N 2-chloro-6-(trifluoromethyl)-1,3-benzothiazole Chemical compound FC(F)(F)C1=CC=C2N=C(Cl)SC2=C1 YIRRVMGAKFESLR-UHFFFAOYSA-N 0.000 description 1
- CLEOKTJHYLXEKQ-UHFFFAOYSA-N 2-chloro-6-methyl-1,3-benzoxazole Chemical compound CC1=CC=C2N=C(Cl)OC2=C1 CLEOKTJHYLXEKQ-UHFFFAOYSA-N 0.000 description 1
- CVNMRDXBPVOJFI-UHFFFAOYSA-N 2-chloro-[1,3]oxazolo[5,4-c]pyridine Chemical compound C1=NC=C2OC(Cl)=NC2=C1 CVNMRDXBPVOJFI-UHFFFAOYSA-N 0.000 description 1
- POXIZPBFFUKMEQ-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical group [N-]=C=[C+]C#N POXIZPBFFUKMEQ-UHFFFAOYSA-N 0.000 description 1
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 1
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- HXWWMGJBPGRWRS-CMDGGOBGSA-N 4- -2-tert-butyl-6- -4h-pyran Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-CMDGGOBGSA-N 0.000 description 1
- CATUKADCLPCACU-UHFFFAOYSA-N 4-(4-aminophenyl)-3-(4-phenylphenyl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1C1=CC=C(C=2C=CC=CC=2)C=C1 CATUKADCLPCACU-UHFFFAOYSA-N 0.000 description 1
- XAINRWAHQMXKJJ-UHFFFAOYSA-N 5,12-diphenylchrysene Chemical compound C1(=CC=CC=C1)C1=CC2=CC=CC=C2C=2C=C(C=3C=CC=CC3C21)C2=CC=CC=C2 XAINRWAHQMXKJJ-UHFFFAOYSA-N 0.000 description 1
- HASALPWGHPTQBW-UHFFFAOYSA-N 5-bromo-1,2-diphenylbenzimidazole Chemical group N=1C2=CC(Br)=CC=C2N(C=2C=CC=CC=2)C=1C1=CC=CC=C1 HASALPWGHPTQBW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
- NGVPTMGYYAQJMS-UHFFFAOYSA-N 9,9-diethyl-N,N-diphenyl-7-[2-[4-(9-phenylfluoren-9-yl)phenyl]ethenyl]fluoren-2-amine Chemical compound C1(=CC=CC=C1)N(C1=CC=2C(C3=CC(=CC=C3C=2C=C1)C=CC1=CC=C(C=C1)C1(C2=CC=CC=C2C=2C=CC=CC1=2)C1=CC=CC=C1)(CC)CC)C1=CC=CC=C1 NGVPTMGYYAQJMS-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000007125 Buchwald synthesis reaction Methods 0.000 description 1
- JDTWRMODUKFHDU-UHFFFAOYSA-N C1=CNC2=C3C=NN=C3C=CC2=N1 Chemical class C1=CNC2=C3C=NN=C3C=CC2=N1 JDTWRMODUKFHDU-UHFFFAOYSA-N 0.000 description 1
- MSDMPJCOOXURQD-UHFFFAOYSA-N C545T Chemical compound C1=CC=C2SC(C3=CC=4C=C5C6=C(C=4OC3=O)C(C)(C)CCN6CCC5(C)C)=NC2=C1 MSDMPJCOOXURQD-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical class O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- XCHARIIIZLLEBL-UHFFFAOYSA-N Medicagenic acid 3-O-beta-D-glucoside Chemical compound C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C(O)=O)C)(C)C1=CCC2C3(C)CC(O)C4OC1OC(CO)C(O)C(O)C1O XCHARIIIZLLEBL-UHFFFAOYSA-N 0.000 description 1
- CVHBCNYGVVJRGC-UHFFFAOYSA-N N1=C(C=CC=C1)C[Ir] Chemical compound N1=C(C=CC=C1)C[Ir] CVHBCNYGVVJRGC-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol Chemical compound [Al+3].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical class C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- GRADOOOISCPIDG-UHFFFAOYSA-N buta-1,3-diyne Chemical group [C]#CC#C GRADOOOISCPIDG-UHFFFAOYSA-N 0.000 description 1
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 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 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([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
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- CYEFKCRAAGLNHW-UHFFFAOYSA-N furan-3-ylboronic acid Chemical compound OB(O)C=1C=COC=1 CYEFKCRAAGLNHW-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- KEQRPCPOINRCDB-UHFFFAOYSA-N iridium(3+);pentane-2,4-dione;1-phenylisoquinoline Chemical compound [Ir+3].CC(=O)CC(C)=O.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 KEQRPCPOINRCDB-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002847 norbornane derivatives Chemical class 0.000 description 1
- 125000005574 norbornylene group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000005550 pyrazinylene group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005558 triazinylene group Chemical group 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
- H10K50/181—Electron blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
本发明提供了一种杂环衍生物及其有机电致发光器件,涉及有机光电材料技术领域。本发明式I的杂环衍生物具有较高的电子迁移率以及较好的空穴阻挡性能,因此将其作为电子传输区域材料尤其是空穴阻挡材料得到的有机电致发光器件具有较低的驱动电压以及较高的发光效率。本发明的有机电致发光器件还可以包括空穴传输区域,空穴传输区域尤其是发光辅助层中含有式II的三芳胺化合物,由于该器件中电子传输区域和空穴传输区域能够更好地平衡载流子,减少了激子的淬灭,提高了载流子的复合几率,因此表现出更低的驱动电压和更高的发光效率。
Description
技术领域
本发明涉及有机光电材料技术领域,具体涉及一种杂环衍生物及其有机电致发光器件。
背景技术
OLED技术是指有机材料在电场作用下发光的技术,根据驱动方式的不同可将OLED分为被动式OLED(Passive Matrix,PMOLED)与主动式OLED(Active Matrix,AMOLED)。OLED是继CRT以及LCD之后的新一代平板显示技术,具有视角宽、响应速度快、功耗低、固态结构抗震性好、工作温度范围宽、轻薄性、可挠性等特点,被誉为“梦幻般的显示技术”。
有机电致发光器件的电致发光过程就是一个能量转移的过程,它将电能转化为光能,在这个转化的过程中,把有机电致发光器件看成是一个注入型的发光二极管。在有机电致发光器件的两端加上电压,通过这个电压所产生的电场,使得空穴从器件的阳极注入到空穴传输层中,而电子则从器件的阴极被注入到电子传输层中,两种载流子迁移进入发光层中并结合形成激子,激子辐射跃迁就会发光。
有机电致发光器件其结构是简单的“三明治”结构,将有机功能层置于阳极和阴极之间就构成一个基本的器件。其中的有机功能层可以为单层有机功能层、双层有机功能层、三层有机功能层以及多层有机功能层,有机功能层的种类可以为空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层等。
由上可知有机电致发光器件是由多种性能各异的功能层组成的叠层结构,它们的功能不同,又相互配合,形成一个有机的整体。其中的各个功能层又对应相关的功能材料,即空穴注入材料、空穴传输材料、电子阻挡材料、发光材料、空穴阻挡材料、电子传输材料、电子注入材料等。发光材料性能虽然对有机电致发光器件非常重要,但器件的性能要得到综合提高,不仅仅要有高品质的发光材料,还需要许多性质优良的辅助材料,如空穴注入材料、空穴传输材料、电子阻挡材料、空穴阻挡材料、电子传输材料、电子注入材料等。这些辅助材料性能的改进,有助于有机电致发光器件性能的提升,因此,研究开发出新的辅助材料具有重要意义。
发明内容
针对现有技术存在的上述问题,本发明提供了一种杂环衍生物及其有机电致发光器件。
本发明提供一种杂环衍生物,具有如式I所示的结构通式,
所述Ar1、Ar2相同或者不同,选自如下所示基团,
所述R0选自氢、氘、卤素、氰基、硝基、取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种,
所述X0选自O、S、N(Rx)、C(Rx)2中的一种,所述Rx选自取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种,
所述Z选自C(Ry)或N,所述Ry选自氢、氘、卤素、氰基、硝基、取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C2~C30的烯基、取代或未取代的C2~C30的炔基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种,或者相邻两个基团之间连接成环;
所述X选自O、S、N(Ar)、C(Ar)2、Si(Ar)2中的一种,所述Ar选自取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种;
所述m选自0、1、2、3或者4,所述R相同或者不同的选自氘、氰基、硝基、取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C2~C30的烯基、取代或未取代的C2~C30的炔基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种,或者相邻两个基团之间连接成环;
所述Lx、Ly独立的选自单键、取代或未取代的C1~C30的亚烷基、取代或未取代的C3~C30的亚环烷基、取代或未取代的C6~C60的亚芳基、取代或未取代的C3~C60的亚杂芳基中的一种;
所述L1、L2独立的选自单键、取代或未取代的C6~C60的亚芳基、取代或未取代的C3~C60的亚杂芳基中的一种。
本发明还提供了一种有机电致发光器件,包括阳极、有机物层、阴极,所述有机物层位于阳极和阴极之间,所述有机物层包括电子传输区域,所述电子传输区域含有上述本发明的杂环衍生物。
有益效果:本发明式I所示的杂环衍生物具有较高的电子迁移率以及较好的空穴阻挡性能,除了能够较好地平衡载流子之外还能够很好地阻挡空穴使其不进入电子传输区域,因此将其用于空穴阻挡层得到的有机电致发光器件表现出较低的驱动电压以及较高的发光效率。
另外,由于式II的三芳胺化合物具有较高的空穴迁移率,其作为发光辅助层时所在的空穴传输区域与上述空穴阻挡层所在的电子传输区域能够有效的平衡载流子,减少了激子的淬灭,提高了载流子的复合几率,因此器件表现出更好的光电性能。
附图说明
图1为本发明化合物1的1H NMR图;图2为本发明化合物22的1H NMR图;
图3为本发明化合物51的1H NMR图;图4为本发明化合物108的1H NMR图。
具体实施方式
下面结合具体实施例,进一步阐明本发明,应理解这些实施例仅用于说明本发明而不用于限制本发明的范围,在阅读了本发明之后,本领域技术人员对本发明的各种等价形式的修改均落于本申请所要求保护的范围内。
本发明所述的“卤素”包括氟、氯、溴、碘。
本发明中的“取代或未取代”中的“未取代”表示基团上的氢原子未被任何取代基替换。
本发明中的“取代或未取代”中的“取代”表示基团上的至少一个氢原子被取代基所替换。当有多个氢被多个取代基替换时,所述多个取代基可以相同或者不同。上述被取代基所替换的氢的位置可以为任意位置。上述“取代”中所表示的取代基包括但不限于如下基团,氘、卤素、氰基、硝基、C1~C30的烷基、C3~C30的环烷基、C6~C60的芳基、C3~C60的杂芳基、C6~C60的胺基中的至少一种。
本发明所述的连接成环是指两个基团通过化学键彼此连接,本发明中,连接形成的环可以为五元环或六元环或者稠合环,例如苯环、萘环、菲环、蒽环、三亚苯环、芴环、喹啉环、二苯并呋喃环、二苯并噻吩环、咔唑环等,但不限于此。
本发明所述的烷基是指烷烃分子中去掉一个氢原子而成的一价基团。所述烷基包括直链烷基、支链烷基。对烷基的碳原子数没有特别限制,优选为C1~C60,进一步优选为C1~C30,更进一步优选为C1~C15,最优选为C1~C10。所述烷基的实例包括但不限于如下所述的基团,甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基等。本发明三个碳以上的链状烷基包括其异构体,例如丙基包括正丙基、异丙基,叔丁基包括正丁基、叔丁基、异丁基、仲丁基,以此类推。
本发明所述的环烷基是指环烷烃分子中去掉一个氢原子而成的一价基团。对环烷基的碳原子数没有特别限制,优选为C3~C60,进一步优选为C3~C30,更进一步优选为C3~C15,最优选为C3~C10。所述环烷基的实例包括但不限于如下所述的基团,环丙基、环丁基、环戊基、环己基、环辛烷、金刚烷基、莰烷基、降冰片烷基、立方烷基等。
本发明所述的芳基是指芳烃分子的母核上去掉一个氢原子得到的一价基团。所述芳基包括单环芳基、多环芳基和稠环芳基。对芳基的碳原子数没有特别限制,优选为C6~C60,进一步优选为C6~C30,更进一步优选为C6~C18,最优选,进一步优选为C6~C14。所述芳基的实例包括但不限于如下所述的基团,苯基、联苯基、三联苯基、四联苯基、萘基、蒽基、苯并蒽基、菲基、三亚苯基、芘基、苯并芘基、苝基、荧蒽基、茚基、芴基、苯并芴基、二苯并芴基、螺二芴基、苯并螺二芴基、二苯并螺二芴基等。
本发明所述的杂芳基是指杂环芳烃分子的母核上去掉一个氢原子得到的一价基团。所述杂芳基中的杂原子包括但不限于如下所述原子,O、S、N、Si、B、P、Se等。所述杂芳基包括单环杂芳基、多环杂芳基和稠环杂芳基。对杂芳基的碳原子数没有特别限制,优选为C3~C60,进一步优选为C3~C30,更进一步优选为C3~C15,最优选,进一步优选为C3~C8。所述杂芳基实例包括但不限于如下所述的基团,吡啶基、吡嗪基、哒嗪基、嘧啶基、三嗪基、喹啉基、异喹啉基、喹喔啉基、喹唑啉基、菲啰啉基、噁二唑基、噁唑基、苯并噁唑基、萘并噁唑基、菲并噁唑基、噻唑基、苯并噻唑基、萘并噻唑基、菲并噻唑基、咪唑基、苯并咪唑基、萘并咪唑基、菲并咪唑基、呋喃基、苯并呋喃基、二苯并呋喃基、苯并二苯并呋喃基、噻吩基、苯并噻吩基、二苯并噻吩基、苯并二苯并噻吩基、咔唑基、苯并咔唑基、二苯并咔唑基、吖啶基等。
本发明所述的烯基是指烯烃分子中去掉一个氢原子得到的一价基团,所述烯基包括单烯基、二烯基、多烯基等。对烯基的碳原子数没有特别限制,优选为C2~C60,进一步优选为C2~C30,更进一步优选为C2~C15,最优选为C2~C10。所述烯基的实例包括但不限于如下所述的基团,乙烯基、丁二烯基等。
本发明所述的炔基是指炔烃分子中去掉一个氢原子得到的一价基团,所述炔基包括单炔基、二炔基、多炔基等。对炔基的碳原子数没有特别限制,优选为C2~C60,进一步优选为C2~C30,更进一步优选为C2~C15,最优选为C2~C10。所述炔基的实例包括但不限于如下所述的基团,乙炔基、丁二炔基等。
本发明所述的亚烷基是指烷烃分子中去掉两个氢得到的二价基团。对亚烷基的碳原子数没有特别限制,优选为C1~C60,进一步优选为C1~C30,更进一步优选为C1~C15,最优选为C1~C10。所述亚烷基的实例包括但不限于如下所示的基团,亚甲基、亚乙基等。
本发明所述的亚环烷基是指环烷烃分子中去掉两个氢得到的二价基团。对亚烷基的碳原子数没有特别限制,优选为C3~C60,进一步优选为C3~C30,更进一步优选为C3~C15,最优选为C3~C10。所述亚烷基的实例包括但不限于如下所示的基团,亚金刚烷基、亚莰烷基、亚降冰片烷基等。
本发明所述的亚芳基是指芳香烃分子中的母核上去掉两个氢原子得到的二价基团。所述亚芳基包括单环亚芳基、多环亚芳基、稠环亚芳基或者其组合。对亚芳基的碳原子数没有特别限制,优选为C6~C60,进一步优选为C6~C30,更进一步优选为C6~C18,最优选,进一步优选为C6~C14。所述亚芳基实例包括但不限于如下所述的基团,亚苯基、亚联苯基、亚三联苯基、亚四联苯基、亚萘基、亚菲基、亚蒽基、亚三亚苯基、亚芘基、亚芴基、亚苯并芴基、亚螺二芴基、亚苯并螺二芴基等。本发明所述的亚芳基还包括单环芳烃与稠环芳烃通过单键相连得到的二价基团、稠环芳烃与稠环芳烃通过单键相连得到的二价基团,例如为苯与菲通过单键相连得到的二价基团,以此类推。
所述亚杂芳基是指杂环芳烃分子的母核上去掉两个氢原子得到的二价基团。所述杂原子包括但不限于如下所示原子,O、S、N、Si、B、P、Se等。所述亚杂芳基包括单环亚杂芳基、多环亚杂芳基、稠环亚杂芳基或者其组合。所述多环亚杂芳基上可以仅有一个被杂原子取代的苯环也可以有多个被杂原子取代的苯环。对亚杂芳基的碳原子数没有特别限制,优选为C6~C60,进一步优选为C6~C30,更进一步优选为C3~C15,最优选,进一步优选为C3~C8。所述亚杂芳基实例包括但不限于如下所述的基团,亚吡啶基、亚嘧啶基、亚吡嗪基、亚哒嗪基、亚三嗪基、亚呋喃基、亚噻吩基、亚喹啉基、亚异喹啉基、亚喹喔啉基、亚喹唑啉基、亚菲啰啉基、亚苯并呋喃基、亚二苯并呋喃基、亚苯并二苯并呋喃基、亚苯并噻吩基、亚二苯并噻吩基、亚苯并二苯并噻吩基、亚咔唑基、亚苯并咔唑基等。本发明所述的亚杂芳基还包括杂环芳烃与杂环芳烃通过单键相连得到的二价基团、芳烃与杂环芳烃通过单键相连得到的二价基团,例如为吡啶与苯通过单键相连得到的二价基团,以此类推。
所述的“取代或未取代的C1~C30的烷基”中的“C1~C30”表示未取代的“烷基”中的碳原子数,不包含取代基中的碳原子数。所述的“取代或未取代的C6~C60的芳基”中的“C6~C60”表示未取代的“芳基”中的碳原子数,不包含取代基中的碳原子数。所述的“取代或未取代的C3~C60的杂芳基”中的“C3~C60”表示未取代的“杂芳基”中的碳原子数,不包含取代基中的碳原子数。所述的“取代或未取代的C6~C60的亚芳基”中的“C6~C60”表示未取代的“亚芳基”中的碳原子数,不包含取代基中的碳原子数。所述的“取代或未取代的C3~C60的亚杂芳基”中的“C3~C60”表示未取代的“亚杂芳基”中的碳原子数,不包含取代基中的碳原子数。以此类推。
本发明提供了一种杂环衍生物,具有如式I所示的结构通式,
所述Ar1、Ar2相同或者不同,选自如下所示基团,
所述R0选自氢、氘、卤素、氰基、硝基、取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种,
所述X0选自O、S、N(Rx)、C(Rx)2中的一种,所述Rx选自取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种,
所述Z选自C(Ry)或N,所述Ry选自氢、氘、卤素、氰基、硝基、取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C2~C30的烯基、取代或未取代的C2~C30的炔基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种,或者相邻两个基团之间连接成环;
所述X选自O、S、N(Ar)、C(Ar)2、Si(Ar)2中的一种,所述Ar选自取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种;
所述m选自0、1、2、3或者4,所述R相同或者不同的选自氘、氰基、硝基、取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C2~C30的烯基、取代或未取代的C2~C30的炔基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种,或者相邻两个基团之间连接成环;
所述Lx、Ly独立的选自单键、取代或未取代的C1~C30的亚烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C6~C60的亚芳基、取代或未取代的C3~C60的亚杂芳基中的一种;
所述L1、L2独立的选自单键、取代或未取代的C6~C60的亚芳基、取代或未取代的C3~C60的亚杂芳基中的一种。
优选的,所述Lx、Ly独立的选自单键、取代或未取代的亚金刚烷基、取代或未取代的亚莰烷基、取代或未取代的亚降冰片烷基、取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚萘基、取代的或未取代的亚菲基、取代或未取代的亚三亚苯基、取代或未取代的亚芴基、取代或未取代的亚苯并芴基、取代或未取代的亚螺二芴基、取代或未取代的亚苯并螺二芴基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚咔唑基、取代或未取代的亚喹啉基、取代或未取代的亚异喹啉基、取代或未取代的萘啶基、取代或未取代的亚喹喔啉基、取代或未取代的亚喹唑啉基、取代或未取代的亚菲啰啉基中的一种;
所述L1、L2独立的选自单键或者如下所示基团中的一种,
所述T相同或者不同的选自N或者C(Rm),所述Rm选自氢、氘、氰基、硝基、取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种;
所述Y选自O、S、N(Rn)、C(Rn)2中的一种,所述Rn选自氢、氘、取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C2~C30的烯基、取代或未取代的C2~C30的炔基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种,或者相邻两个基团连接成环;
所述L0相同或者不同的选自单键、取代或未取代的C6~C60的亚芳基、取代或未取代的C3~C60的亚杂芳基中的一种。
优选的,所述Ar1、Ar2独立的选自如下所示基团中的一种,
优选的,所述L1、L2独立的选自单键或者如下所示基团中的一种,
优选的,所述杂环衍生物选自如下所示结构中的一种,
以上列举了本发明式I所示的杂环衍生物的一些具体化学结构,但本发明不局限于所列的这些化学结构,凡是以式I所示结构为基础,取代基为如上所限定的基团都应包含在内。
进一步的,本发明还提供了一种有机电致发光器件,包括阳极、有机物层、阴极,所述有机物层位于阳极和阴极之间,所述有机物层包括电子传输区域,所述电子传输区域含有上述本发明的杂环衍生物。
本发明所述的电子传输区域由空穴阻挡层、电子传输层、电子注入层或者具有电子注入/传输性质的功能层中的一层或者多层构成。优选空穴阻挡层和/或电子传输层中含有本发明的杂环衍生物,最优选空穴阻挡层中含有本发明的杂环衍生物。
优选的,所述有机物层还包括空穴传输区域,所述空穴传输区域含有式II所示的三芳胺化合物,本发明所述的空穴传输区域由电子阻挡层、发光辅助层、空穴传输层、空穴注入层或者具有空穴注入/传输性质的功能层中的一层或者多层构成。优选电子阻挡层、发光辅助层和/或空穴传输层中含有本发明式II所示的三芳胺化合物,最优选发光辅助层和/或空穴传输层中含有本发明式II所示的三芳胺化合物。
其中,A、B独立的选自如下取代基中的一种:
其中,所述Ra相同或不同地选自氢、氘、取代或未取代的C1~C15的烷基、取代或未取代的C3~C15的环烷基、取代或未取代的C2~C30的烯基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种,或者相邻的两个基团连接成环;
所述Rb相同或不同地选自氢、氘、取代或未取代的C1~C15的烷基、取代或未取代的C3~C15的环烷基、取代或未取代的C2~C30的烯基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种,或者相邻的两个基团连接成环;
所述La选自单键、取代或未取代的C6~C30的亚芳基、取代或未取代的C3~C30的亚杂芳基中的一种;
所述a选自0、1、2、3或者4,所述b选自0、1、2、3、4或者5;
所述C选自如下基团中的一种:
其中,所述R12选自甲基、乙基、丙基、丁基、苯基、甲苯基、联苯基、萘基中的一种;
所述R13选自氘、甲基、乙基、丙基、丁基、环己基、金刚烷基、苯基、甲苯基、联苯基、三联苯基、萘基、蒽基、菲基、三亚苯基、吖啶基、螺二芴基、9,9-二甲基芴基、9,9-二苯基芴基、9-苯基咔唑基、芘基、吲哚基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基中的一种;
所述Lb选自单键、亚苯基、亚氘代苯基、亚氘代萘基、亚甲苯基、亚联苯基、亚萘基、亚三联苯基、亚二苯并呋喃基、亚芴基、亚二苯并噻吩基中的一种;
所述c选自0、1、2、3、4或者5;d选自0、1、2、3或者4;e选自0、1、2、3、4、5、6或者7;f选自0、1、2、3、4、5、6、7、8或者9。
优选的,所述C选自如下基团中的一种:
优选的,所述Ra独立的选自氢、氘、甲基、乙基、丙基、丁基、金刚烷基、莰烷基、降冰片烷基、苯基、甲苯基、联苯基、三联苯基、萘基、蒽基、菲基、三亚苯基、吖啶基、螺二芴基、9,9-二甲基芴基、9,9-二苯基芴基、9-苯基咔唑基、芘基、吲哚基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基中的一种,或者相邻两个基团之间连接成环;
所述La选自单键、亚苯基、亚甲苯基、亚联苯基、亚萘基、亚三联苯基、亚二苯并呋喃基、亚芴基、亚二苯并噻吩基中的一种;
所述Rb相同或不同地选自氢、氘、甲基、乙基、丙基、丁基、金刚烷基、莰烷基、降冰片烷基、苯基、甲苯基、联苯基、三联苯基中的一种,或者相邻两个基团之间连接成环。
优选的,所述式II所示的三芳胺化合物中,取代基A、B、C中至少一个含有氘。
优选的,所述式II所示的三芳胺化合物中,取代基A、B、C中至少一个含有金刚烷基。
优选的,基团A、B独立的选自如下所示基团中的一种,
优选的,基团C选自如下所示基团中的一种,
优选的,所述式II所示的三芳胺化合物选自如下所示结构中的一种,
以上列举了本发明式II所示的三芳胺化合物的一些具体化学结构,但本发明不局限于所列的这些化学结构,凡是以式II所示结构为基础,取代基为如上所限定的基团都应包含在内。
本发明的有机电致发光器件中的有机物层可以包括如下所述功能层中的一种或者多种,空穴注入层、发光辅助层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层等。每种功能层可以由单层薄膜构成,也可以由多层薄膜构成,每一层薄膜可以包含一种材料也可以包含多种材料。对每个功能层的膜厚没有特别限制,优选为0.01nm~1μm。其中,至少一种功能层中包含式I所示的杂环衍生物,优选电子传输区域,即空穴阻挡层、电子传输层和/或电子注入层中含有式I所示的杂环衍生物。优选空穴传输区域,即电子阻挡层、发光辅助层、空穴传输层和/或空穴注入层中含有本发明式II所示的三芳胺化合物。
本发明对有机电致发光器件中的各层薄膜的材料没有特别的限定,除了上述本发明式I所示的杂环衍生物或本发明式II所示的三芳胺化合物外,还可以使用本领域中已知的物质。下面对上述提到的有机电致发光器件的各有机功能层中的材料以及器件两侧的电极材料分别进行介绍:
阳极材料优选高功函数的材料以便空穴注入有机层。本发明的阳极材料包括金属、金属氧化物、金属合金、金属和氧化物的组合、导电聚合物等。所述阳极材料包括但不限于如下所述的实例,金、钒、铬、铜、钯、镍、氧化铟锡(ITO)、氧化铟锌(IZO)、氧化锌、氧化铟、氧化锡:锑(SnO2:Sb)、聚吡咯等。
空穴注入材料具有将空穴注入到有机层中的作用,包括金属氧化物、酞菁类化合物、芳胺化合物、含多氰基的共轭有机材料、高分子材料等。所述空穴传输材料的实例包括但不限于如下所述的材料,三氧化钼(MoO3)、酞菁铜(CuPc)、4,4',4”-三(N-3-甲基苯基-N-苯基氨基)三苯胺(m-MTDATA)、4,4',4”-三[2-萘基苯基氨基]三苯基胺(2T-NATA)、1,4,5,8,9,11-六氮杂苯甲腈(HAT-CN)、(2E,2'E,2”E)-2,2',2”-(环丙烷-1,2,3-三亚基)三(2-(全氟苯基)-乙腈)、聚(3,4-亚乙二氧基噻吩)/聚(苯乙烯磺酸)(PEDOT/PSS)等。
空穴传输材料具有注入空穴和平衡载流子的作用,包括芳香胺类化合物和咔唑类化合物等。所述空穴传输材料的实例包括但不限于如下所述的材料,N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(NPB)、N4,N4,N4',N4'-四([1,1'-联苯]-4-基)-[1,1'-联苯]-4,4'-二胺、4,4'-环己基二[N,N-二(4-甲基苯基)苯胺](TAPC)、N,N'-二苯基-N,N'-二(3-甲基苯基)-1,1'-联苯-4,4'-二胺(TPD)、2,2,7,7-四(二苯基氨基)-9,9-螺二芴(Spiro-TAD)、4,4',4”-三(咔唑-9-基)三苯胺(TCTA)等。
发光辅助材料具有注入空穴平衡载流子的作用,同时还可能具有阻挡电子的作用。包括芳香胺类化合物和咔唑类化合物等。所述空穴传输材料的实例包括但不限于如下所述的材料,三(4-联苯基)胺(TBA)、4,4',4”-三[N-(3-甲基苯基)-N-苯基氨基]三苯胺(MTDATA)、N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(NPB)、4,4'-环己基二[N,N-二(4-甲基苯基)苯胺](TAPC)、2,2,7,7-四(二苯基氨基)-9,9-螺二芴(Spiro-TAD)、4,4',4”-三(咔唑-9-基)三苯胺(TCTA)等。
电子阻挡材料具有将电子阻挡在发光层内的作用,包括芳香胺类化合物等。所述电子阻挡材料的实例包括但不限于如下所述的材料,4,4',4”-三(咔唑-9-基)三苯胺(TCTA)、N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(NPB)等。
发光材料具有接收空穴和电子并使两者结合发出可见光的功能,按照发光颜色可分为红光材料、绿光材料和蓝光材料。发光材料可以为荧光材料也可以为磷光材料。发光材料可以单独作为发光层,也可以将它们掺杂到主体材料中作为发光层。
蓝光材料包含苝衍生物、苯乙烯基胺衍生物、蒽衍生物、芴衍生物、金属配合物、有机硅、有机硼等。所述蓝光材料的实例包括但不限于如下所述的材料,2,5,8,11-四叔丁基苝(TBPe)、4,4'-二[4-(二苯氨基)苯乙烯基]联苯(BDAVBi)、9-[4-(2-(7-(N,N-二苯基氨基)-9,9-二乙基芴-2-基)乙烯基)苯基]-9-苯基-芴(DPAFVF)、9,10-二-(2-萘基)蒽(AND)、二(4,6-二氟苯基吡啶-C2,N)吡啶甲酰合铱(FIrpic)等。
绿光材料包含香豆素染料、喹吖啶铜类衍生物、多环芳香烃、有机硅化合物、吡唑并喹喔啉类衍生物、胺基蒽类衍生物、六苯并苯、咪唑酮类衍生物、噻吩吡咯、萘酰亚胺、金属配合物等。所述绿光材料的实例包括但不限于如下所述的材料,香豆素545T、N,N'-二甲基喹吖啶酮(DMQA)、5,12-二苯基萘并萘(DPT)、自三(2-苯基吡啶)合铱(Ir(ppy)3)等。
红光材料材料包含DCM系列材料、金属配合物等。所述红光材料的实例包括但不限于如下所述的材料,4-(二氰基亚甲基)-2-甲基-6-(4-二甲基氨基苯乙烯基)-4H-吡喃(DCM)、4-(二氰基甲撑)-2-叔丁基-6-(1,1,7,7-四甲基久洛尼啶-9-烯基)-4H-吡喃(DCJTB)、二(1-苯基异喹啉)(乙酰丙酮)铱(III)(Ir(piq)2(acac))、八乙基卟啉铂(PtOEP)等。
空穴阻挡材料具有将空穴阻挡在发光层内的作用,包括咪唑类化合物、菲啰啉类化合物等杂环类化合物。所述空穴阻挡材料的实例包括但不限于如下所述的材料,1,3,5-三(N-苯基-2-苯并咪唑)苯(TPBi)、4,7-二苯基-1,10-菲罗啉(Bphen)等。优选本发明式I所示的杂环衍生物。
电子传输材料具有注入电子和平衡载流子的作用,包括吡啶衍生物、咪唑衍生物、噁二唑衍生物、三氮唑类衍生物、菲啰啉衍生物等杂环化合物、金属配合物等。所述电子传输材料的实例包括但不限于如下所述的材料,三(8-羟基喹啉)合铝(III)(Alq3)、3,3'-[5'-[3-(3-吡啶基)苯基](TmPyPB)、1,3,5-三(N-苯基-2-苯并咪唑)苯(TPBi)、2-(4-联苯基)-5-(4-叔丁基苯基)-1,3,4-噁二唑(PBD)、3-(联苯-4-基)-4-苯基-5-(4-叔丁基苯基)-1,2,4-三唑(TAZ)、4,7-二苯基-1,10-菲罗啉(Bphen)等。
电子注入材料具有将电子注入到有机层的作用,包括碱金属的无机盐、碱金属氧化物、碱金属的有机盐、碱金属氟化物、碱金属配合物等。所述电子注入材料的实例包括但不限于如下所述的材料,碳酸铯(Cs2CO3)、氧化锂(Li2O)、醋酸钾(CH3COOK)、氟化锂(LiF)、8-羟基喹啉锂(Liq)等。
阴极材料优选低功函数的材料以便电子注入有机层。本发明的阴极材料包括金属、金属合金等。所述阴极包括但不限于如下所述的实例,铝、银、镁、钙、镁银合金等。
对本发明有机电致发光器件中各层薄膜的制备方法没有特别限制,可以采用真空蒸镀法、溅射法、旋涂法、喷涂法、丝网印刷法、激光转印法等,但不限于此。
本发明的有机电致发光器件主要应用于信息显示技术领域,在信息显示方面被广泛应用于各种信息显示,如平板电脑、平板电视、手机、智能手表、数码照相机、VR、车载系统、可穿戴设备等。
合成实施例
对本发明式I所示的杂环衍生物的制备方法没有特别限制,可以采用本领域的技术人员所熟知的常规方法。例如,碳碳偶联反应等,更具体的可以采用铃木反应等,本发明式I的杂环衍生物可以采用如下所示的几种合成路线进行制备。
路线一:Lx、Ly不同同时为单键
路线二:Lx、Ly同时为单键
对本发明式II所示的三芳胺化合物的制备方法没有特别限制,可以采用本领域的技术人员所熟知的常规方法。例如,碳氮偶联反应等,更具体的可以采用布赫瓦尔德反应、乌尔曼反应等。
原料与试剂:本发明所用的原料及试剂均为试剂纯。本发明对以下合成实施例中所采用的原料或试剂没有特别的限制,可以为市售产品或采用本领域技术人员所熟知的制备方法制备得到。
仪器:(1)G2-Si四极杆串联飞行时间高分辨率质谱仪(沃特斯公司,英国);(2)Vario EL cube型有机元素分析仪(Elementar公司,德国);(3)Bruker-510型核磁共振谱仪(Bruker公司,德国)。
合成实施例1:化合物1的制备
(1)在N2气氛下,将三环己基膦(0.280g,1.0mmol)、三(二亚苄基丙酮)二钯(0.458g,0.5mmol)加入到2-溴螺[芴-9,9'-氧杂蒽](12.3g,30mmol)、4-氯苯硼酸(3.91g,25mmol)、二氧六环(80ml)、碳酸钠溶液(1.25M,40ml)的混合溶液中,回流过夜。将反应液冷却至室温,用乙酸乙酯萃取,有机层用无水硫酸镁干燥,过滤,减压蒸馏除去溶剂后用硅胶柱分离,洗脱剂为二氯甲烷和正己烷(2:1),得到8.42g的化合物D1,产率76%。
(2)在N2气氛下,将双(三苯基膦)二氯化钯(0.245g,0.35mmol)加入到双联频哪醇基二硼烷(5.33g,21.0mmol)、化合物D1(7.79g,17.5mmol)、醋酸钾(5.15g,52.5mmol)与四氢呋喃(230ml)的混合液中,回流反应4小时。将反应液冷却至室温,减压蒸馏出去四氢呋喃溶液,加入氯仿和蒸馏水并分离有机层,再用氯仿萃取水层,有机层用无水硫酸镁干燥,过滤,减压蒸馏除去溶剂后用硅胶柱分离,洗脱剂为二氯甲烷和石油醚(3:1),得到7.76g的化合物E1,产率83%。
(3)在N2气氛下,将(0.162g,0.14mmol)四(三苯基膦)合钯加入到1-溴-3,5-二氯苯(3.16g,14mmol)、化合物E1(7.48g,14mmol)、碳酸钠溶液(2M,24.5ml)、乙醇(25ml)和甲苯(250ml)的混合溶液中,回流搅拌过夜。将反应液冷却至室温,用氯仿萃取,有机层用无水硫酸镁干燥,过滤,减压蒸馏除去溶剂后用硅胶柱分离,洗脱剂为乙酸乙酯和正己烷(2:1),得到6.28g的化合物F1,产率81%。
(4)在N2气氛下,将三(二亚苄基丙酮)二钯(0.366g,0.4mmol)、三环己基膦(0.224g,0.8mmol)加入到化合物F1(5.54g,10mmol)、双联频哪醇基二硼烷(5.08g,20mmol)、碳酸钠溶液(1.25M,32ml)、二氧六环(65ml)的混合溶液中,回流过夜。将反应液冷却至室温,用二氯甲烷萃取,有机层用无水硫酸镁干燥,过滤,减压蒸馏除去溶剂后用硅胶柱分离,洗脱剂为二氯甲烷和正己烷(5:2),得到5.38g的化合物G1,产率73%。
(5)在N2气氛下,将1,1'-双二苯基膦二茂铁二氯化钯(0.732g,0.1mmol)加入到化合物G1(3.68g,5mmol)、2-氯苯并噁唑(1.84g,12mmol)、磷酸钾溶液(2M,10ml)、甲苯(50ml)的混合溶液中,回流反应一天。将反应液冷却至室温,用二氯甲烷萃取,有机层用无水硫酸镁干燥,过滤,减压蒸馏除去溶剂后用硅胶柱分离,洗脱剂为二氯甲烷和乙醇(3:1),得到2.84g的化合物1,产率79%。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:718.2256,实测值:718.2267。理论元素含量(%)C51H30N2O3:C,85.22;H,4.21;N,3.90,实测元素含量(%):C,85.20;H,4.27;N,3.94。1H NMR(600MHz,CDCl3,ppm)δ:8.28(s,1H),8.22–8.19(m,2H),8.07(d,1H),8.02(s,1H),7.95–7.90(m,3H),7.89–7.83(m,3H),7.66–7.62(m,5H),7.60–7.57(m,1H),7.46–7.42(m,1H),7.40–7.33(m,6H),7.31–7.24(m,2H),7.11–7.06(m,2H),7.02–6.95(m,2H)。上述结果证实获得产物为目标产品。
合成实施例2:化合物6的制备
将合成实施例1中的2-氯苯并噁唑换成等摩尔的2-氯-6-甲基-苯并噁唑,其他步骤相同,得到2.58g的化合物6。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:746.2569,实测值:746.2593。理论元素含量(%)C53H34N2O3:C,85.23;H,4.59;N,3.75,实测元素含量(%):C,85.12;H,4.76;N,3.83。
合成实施例3:化合物19的制备
将合成实施例1中的2-氯苯并噁唑换成等摩尔的6-溴-2-苯基苯并[D]噁唑,其他步骤相同,得到3.05g的化合物19。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:870.2882,实测值:870.2894。理论元素含量(%)C63H38N2O3:C,86.88;H,4.40;N,3.22,实测元素含量(%):C,86.97;H,4.30;N,3.21。
合成实施例4:化合物22的制备
将合成实施例1中的4-氯苯硼酸换成等摩尔的3-氯苯硼酸,2-氯苯并噁唑换成等摩尔的2-氯噁唑并[5,4-C]吡啶,其它步骤相同,得到2.59g的化合物22。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:720.2161,实测值:720.2180。理论元素含量(%)C49H28N4O3:C,81.65;H,3.92;N,7.77,实测元素含量(%):C,81.74;H,3.98;N,7.63。1H NMR(600MHz,CDCl3,ppm)δ:8.70(s,1H),8.67(s,1H),8.42(d,1H),8.39(d,1H),8.27(t,1H),8.20(d,2H),8.09–8.04(m,2H),8.02(t,1H),7.93(d,1H),7.88–7.85(m,1H),7.78–7.70(m,4H),7.67–7.63(m,2H),7.61–7.56(m,1H),7.47–7.41(m,1H),7.37–7.33(m,2H),7.30–7.25(m,2H),7.14–7.10(m,2H),7.01–6.95(m,2H)。
合成实施例5:化合物29的制备
将合成实施例1中的4-氯苯硼酸换成等摩尔的4-氯-4-联苯硼酸,其它步骤相同,得到3.26g的化合物29。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:794.2569,实测值:794.2585。理论元素含量(%)C57H34N2O3:C,86.13;H,4.31;N,3.52,实测元素含量(%):C,86.09;H,4.25;N,3.60。
合成实施例6:化合物37的制备
将合成实施例1中的4-氯苯硼酸换成等摩尔的7-氯二苯并[B,D]呋喃-3-基硼酸,其它步骤相同,得到3.03g的化合物37。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:808.2362,实测值:808.2382。理论元素含量(%)C57H32N2O4:C,84.64;H,3.99;N,3.46,实测元素含量(%):C,84.70;H,3.92;N,3.43。
合成实施例7:化合物42的制备
将合成实施例1中的4-氯苯硼酸换成等摩尔的3-氯-5-氰基苯硼酸,其它步骤相同,得到2.53g的化合物42。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:743.2209,实测值:743.2237。理论元素含量(%)C52H29N3O3:C,83.97;H,3.93;N,5.65,实测元素含量(%):C,83.94;H,3.98;N,5.70。
合成实施例8:化合物43的制备
将合成实施例1中的4-氯苯硼酸换成等摩尔的(4-氯苯基-2,3,5,6-d4)硼酸,其它步骤相同,得到2.64g的化合物43。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:722.2507,实测值:722.2533。理论元素含量(%)C51H26D4N2O3:C,84.74;H,4.74;N,3.88,实测元素含量(%):C,84.69;H,4.77;N,3.85。
合成实施例9:化合物51的制备
在N2气氛下,将双(三苯基膦)二氯化钯(0.123g,0.175mmol)加入到2-溴螺[芴-9,9'-氧杂蒽](7.20g,17.5mmol)、双联频哪醇基二硼烷(5.33g,21.0mmol)、醋酸钾(4.29g,43.75mmol)与四氢呋喃(200ml)的混合液中,回流反应3小时。将反应液冷却至室温,减压蒸馏出去四氢呋喃溶液,加入二氯甲烷和蒸馏水并分离有机层,再用二氯甲烷萃取水层,有机层用无水硫酸镁干燥,过滤,减压蒸馏除去溶剂后用硅胶柱分离,洗脱剂为二氯甲烷和石油醚(3:1),得到6.98g的化合物E5,产率87%。
合成实施例1中从步骤(3)开始,将步骤(3)中的化合物E1换成等摩尔的化合物E5,步骤(5)中的2-氯苯并噁唑换成等摩尔的6-溴-2-苯基苯并[D]噁唑,其它步骤相同,得到3.50g的化合物51。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:794.2569,实测值:794.2597。理论元素含量(%)C57H34N2O3:C,86.13;H,4.31;N,3.52,实测元素含量(%):C,86.02;H,4.39;N,3.48。1H NMR(600MHz,CDCl3,ppm)δ:8.16(s,2H),8.11–8.05(m,7H),7.94(d,1H),7.90(dd,1H),7.80–7.74(m,4H),7.69–7.63(m,3H),7.61–7.57(m,1H),7.46–7.39(m,7H),7.38–7.34(m,2H),7.30–7.26(m,2H),7.12–7.07(m,2H),7.03–6.96(m,2H)。
合成实施例10:化合物57的制备
将合成实施例1中的2-溴螺[芴-9,9'-氧杂蒽]换成等摩尔的3-溴螺[芴-9,9'-氧杂蒽],4-氯苯硼酸换成等摩尔的3'-氯-3-联苯硼酸,其它步骤相同,得到3.38g的化合物57。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:794.2569,实测值:794.2634。理论元素含量(%)C57H34N2O3:C,86.13;H,4.31;N,3.52,实测元素含量(%):C,86.16;H,4.27;N,3.50。
合成实施例11:化合物65的制备
将合成实施例9中的2-溴螺[芴-9,9'-氧杂蒽]换成等摩尔的3-溴螺[芴-9,9'-氧杂蒽],6-溴-2-苯基苯并[D]噁唑换成等摩尔的2-氯苯并噁唑,其它步骤相同,得到2.41g的化合物65。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:642.1943,实测值:642.1964。理论元素含量(%)C45H26N2O3:C,84.10;H,4.08;N,4.36,实测元素含量(%):C,84.21;H,4.19;N,4.28。
合成实施例12:化合物71的制备
将合成实施例1中的2-溴螺[芴-9,9'-氧杂蒽]换成等摩尔的3-溴螺[芴-9,9'-氧杂蒽],4-氯苯硼酸换成等摩尔的6-氯-2-萘硼酸,其它步骤相同,得到2.73g的化合物71。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:768.2413,实测值:768.2446。理论元素含量(%)C55H32N2O3:C,85.92;H,4.20;N,3.64,实测元素含量(%):C,85.80;H,4.15;N,3.68。
合成实施例13:化合物77的制备
将合成实施例1中的2-溴螺[芴-9,9'-氧杂蒽]换成等摩尔的2-溴螺[苯并[B]芴-11,9'-氧杂蒽],其它步骤相同,得到2.69g的化合物77。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:768.2413,实测值:768.2448。理论元素含量(%)C55H32N2O3:C,85.92;H,4.20;N,3.64,实测元素含量(%):C,85.96;H,4.27;N,3.73。
合成实施例14:化合物95的制备
将合成实施例1中的2-氯苯并噁唑换成等摩尔的2-氯-6-三氟甲基苯并噻唑,其它步骤相同,得到2.88g的化合物95。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:886.1547,实测值:886.1565。理论元素含量(%)C53H28F6N2OS2:C,71.77;H,3.18;N,3.16,实测元素含量(%):C,71.61;H,3.21;N,3.09。
合成实施例15:化合物102的制备
将合成实施例1中的4-氯苯硼酸换成等摩尔的3'-氯-3-联苯硼酸,2-氯苯并噁唑换成等摩尔的2-氯苯并噻唑,其它步骤相同,得到2.70g的化合物102。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:826.2113,实测值:826.2126。理论元素含量(%)C57H34N2OS2:C,82.78;H,4.14;N,3.39,实测元素含量(%):C,82.91;H,4.18;N,3.30。
合成实施例16:化合物106的制备
将合成实施例1中的2-溴螺[芴-9,9'-氧杂蒽]换成等摩尔的3-溴螺[芴-9,9'-氧杂蒽],4-氯苯硼酸换成等摩尔的(7-氯-9,9-二甲基-9H-芴-2-基)硼酸,2-氯苯并噁唑换成等摩尔的2-氯苯并噻唑,其它步骤相同,得到2.95g的化合物106。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:866.2426,实测值:866.2451。理论元素含量(%)C60H38N2OS2:C,83.11;H,4.42;N,3.23,实测元素含量(%):C,83.10;H,4.45;N,3.28。
合成实施例17:化合物108的制备
在N2气氛下,将四(三苯基膦)钯(0.104g,0.09mmol)加入到化合物G2(13.3g,18mmol)、2-氯苯并噻唑(3.66g,21.6mmol)、碳酸钾(2M,18ml)、二氧六环(60ml)的混合溶液中,回流反应五小时。将反应液冷却至室温,用氯仿萃取,有机层用无水硫酸镁干燥,过滤,减压蒸馏除去溶剂后用硅胶柱分离,洗脱剂为氯仿和正己烷(3:2),得到6.16g的化合物G2-1,产率46%。
在N2气氛下,将双(三苯基膦)二氯化钯(0.104g,0.09mmol)加入到化合物G2-1(13.3g,5mmol)、2-氯苯并噁唑(3.66g,6mmol)、碳酸钠(1.25M,8ml)、二氧六环(25ml)的混合溶液中,回流反应八小时。将反应液冷却至室温,用二氯甲烷萃取,有机层用无水硫酸镁干燥,过滤,减压蒸馏除去溶剂后用硅胶柱分离,洗脱剂为二氯甲烷和正己烷(2:1),得到3.16g的化合物108,产率86%。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:734.2028,实测值:734.2046。理论元素含量(%)C51H30N2O2S:C,83.36;H,4.11;N,3.81,实测元素含量(%):C,83.47;H,4.12;N,3.79。1H NMR(600MHz,CDCl3,ppm)δ:8.33(s,1H),8.29(s,1H),8.23–8.20(m,2H),8.15–8.10(m,2H),8.09–8.05(m,2H),7.93(d,1H),7.87(dd,1H),7.80–7.77(m,1H),7.74–7.70(m,1H),7.68–7.62(m,4H),7.61–7.56(m,2H),7.52–7.48(m,1H),7.46–7.42(m,1H),7.41–7.33(m,4H),7.30–7.25(m,2H),7.22(dd,1H),7.12(dd,1H),7.01–6.95(m,2H)。
合成实施例18:化合物153的制备
将合成实施例1中的2-溴螺[芴-9,9'-氧杂蒽]换成等摩尔的3-溴螺[芴-9,9'-硫杂蒽],4-氯苯硼酸换成等摩尔的3-氯苯硼酸,其它步骤相同,得到2.65g的化合物153。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:734.2028,实测值:734.2032。理论元素含量(%)C51H30N2O2S:C,83.36;H,4.11;N,3.81,实测元素含量(%):C,83.22;H,4.07;N,3.71。
合成实施例19:化合物164的制备
将合成实施例1中的2-溴螺[芴-9,9'-氧杂蒽]换成等摩尔的3-溴螺[芴-9,9'-硫杂蒽],4-氯苯硼酸换成等摩尔的(7-氯-9,9-二甲基-9H-芴-2-基)硼酸,其它步骤相同,得到3.02g的化合物164。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:850.2654,实测值:850.2647。理论元素含量(%)C60H38N2O2S:C,84.68;H,4.50;N,3.29,实测元素含量(%):C,84.59;H,4.45;N,3.26。
合成实施例20:化合物173的制备
将合成实施例1中的2-溴螺[芴-9,9'-氧杂蒽]换成等摩尔的3-溴螺[芴-9,9'-硫杂蒽],2-氯苯并噁唑换成等摩尔的2-氯苯并噻唑,其他步骤相同,得到2.56g的化合物173。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:766.1571,实测值:766.1585。理论元素含量(%)C51H30N2S3:C,79.87;H,3.94;N,3.65,实测元素含量(%):C,79.68;H,3.83;N,3.75。
合成实施例21:化合物201的制备
将合成实施例1中的2-溴螺[芴-9,9'-氧杂蒽]换成等摩尔的2'-溴-10-苯基-10H-螺[吖啶-9,9'-芴],其它步骤相同,得到3.33g的化合物201。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:793.2729,实测值:793.2815。理论元素含量(%)C57H35N3O2:C,86.23;H,4.44;N,5.29,实测元素含量(%):C,86.32;H,4.38;N,5.20。
合成实施例22:化合物219的制备
将合成实施例9中的2-溴螺[芴-9,9'-氧杂蒽]换成等摩尔的2'-溴-10-苯基-10H-螺[吖啶-9,9'-芴],2-氯苯并噁唑换成等摩尔的2-(4-氯苯基)苯并噻唑,其它步骤相同,得到3.14g的化合物219。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:901.2585,实测值:901.2607。理论元素含量(%)C63H39N3S2:C,83.88;H,4.36;N,4.66,实测元素含量(%):C,83.74;H,4.41;N,4.74。
合成实施例23:化合物244的制备
将合成实施例9中的2-溴螺[芴-9,9'-氧杂蒽]换成等摩尔的9'-[9H]芴],3'-溴-10,10-二甲基-螺[9(10H)-蒽],2-氯苯并噁唑换成等摩尔的5-溴-1,2-二苯基-1H-苯并咪唑,其它步骤相同,得到3.11g的化合物244。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:970.4035,实测值:970.4072。理论元素含量(%)C72H50N4:C,89.04;H,5.19;N,5.77,实测元素含量(%):C,89.18;H,5.08;N,5.72。
合成实施例24:化合物250的制备
将合成实施例1中的2-溴螺[芴-9,9'-氧杂蒽]换成等摩尔的2-溴-螺环[9H-芴-9,9'-[9H]氧杂蒽],4-氯苯硼酸换成等摩尔的3-氯苯硼酸,其它步骤相同,得到2.88g的化合物201。HPLC检测固体纯度≧99.9%。质谱m/z,理论值:718.2256,实测值:718.2291。理论元素含量(%)C51H30N2O3:C,85.22;H,4.21;N,3.90,实测元素含量(%):C,85.33;H,4.26;N,3.80。
合成实施例2~24中的目标化合物如下:
合成实施例25:化合物II-1的制备
在氮气保护下,向1L反应瓶中依次加入甲苯(600mL)、a-1(20.00g,0.06mol)、b-1(23.83g,0.06mol)、醋酸钯(0.21g,0.93mmol)、叔丁醇钠(11.3g,0.117mol)和三叔丁基膦(8mL的甲苯溶液)。并在回流的条件下反应2小时。反应停止后,将混合物冷却至室温,用硅藻土过滤,浓缩滤液,用甲醇重结晶,抽滤并用甲醇淋洗得重结晶固体,得到中间体A-1(30.41g,产率78%),HPLC检测固体纯度≧99.7%。
在氮气保护下,向1L反应瓶中依次加入甲苯溶剂(600ml),c-1(5.83g,36mmol)、中间体A-1(23.39g,36mmol)、Pd2(dba)3(330mg,0.36mmol)、BINAP(0.67g,1.08mmol)和叔丁醇钠(3.23g,33.6mmol),搅拌溶解,并在氮气的保护下回流反应24小时,反应完成后,将反应液用二氯甲烷和蒸馏水洗涤,分液萃取。有机层用无水硫酸镁干燥,过滤后,除去溶剂,用环己烷:乙酸乙酯=10:1作为洗脱剂柱层析分离提纯精制,最后得化合物II-1(17.89g,产率68%),HPLC检测固体纯度≧99.1%。
质谱m/z,理论值:730.3396,实测值:730.3425。理论元素含量(%)C56H34D5N:C,92.02;H,6.07;N,1.92,实测元素含量(%):C,92.02;H,6.08;N,1.89。
按照与合成实施例25相同的方法制备如下目标产物:
化合物II-47(17.43g),HPLC检测固体纯度≧99.2%。质谱m/z:782.3693(理论值:782.3678)。理论元素含量(%)C60H34D7N:C,92.03;H,6.18;N,1.79,实测元素含量(%):C,92.05;H,6.18;N,1.78。
化合物II-70(19.18g),HPLC检测固体纯度≧99.2%。质谱m/z:806.3798(理论值:806.3709)。理论元素含量(%)C62H38D5N:C,92.27;H,5.99;N,1.74,实测元素含量(%):C,92.29;H,5.99;N,1.74。
化合物II-78(19.82g),HPLC检测固体纯度≧99.6%。质谱m/z:859.4209(理论值:859.4178)。理论元素含量(%)C66H53N:C,92.16;H,6.21;N,1.63,实测元素含量(%):C,92.16;H,6.28;N,1.60。
化合物II-85(18.19g),HPLC检测固体纯度≧99.7%。质谱m/z:801.3411(理论值:801.3396)。理论元素含量(%)C62H43N:C,92.85;H,5.40;N,1.75,实测元素含量(%):C,92.83;H,5.40;N,1.70。
化合物II-90(20.13g),HPLC检测固体纯度≧98.8%。质谱m/z:859.4197(理论值:859.4178)。理论元素含量(%)C66H53N:C,92.16;H,6.21;N,1.63实测元素含量(%):C,92.10;H,6.20;N,1.62。
化合物1-102(18.92g),HPLC检测固体纯度≧99.3%。质谱m/z:875.3584(理论值:875.3552)。理论元素含量(%)C68H45N:C,93.22;H,5.18;N,1.60,实测元素含量(%):C,93.24;H,5.15;N,1.53。
上述目标化合物如下:
器件实施例
有机材料的说明:有机材料都是经过升华,纯度都在99.99%以上。
基板的说明:玻璃基板由5%的玻璃清洗液超声清洗2次,每次20分钟,再由去离子水超声清洗2次,每次10分钟。依次使用丙酮和异丙酮超声清洗20分钟,120℃烘干。
蒸镀系统的说明:器件的制备采用真空蒸镀系统,在真空不间断条件下连续蒸发制备完成。所用材料分别在不同的蒸发源石英坩埚中,蒸发源的温度可以单独控制。有机材料或掺杂母体有机材料的热蒸发速率一般定在0.1nm/s,掺杂材料蒸发速率调节按掺杂比率进行;电极金属蒸发速率在0.4~0.6nm/s。将处理好的玻璃基板放置到OLED真空镀膜机中,在薄膜制作过程中,系统真空度应该维持在5×10-5Pa以下,通过更换掩膜板分别来蒸镀有机层和金属电极,用Inficon的SQM160石英晶体膜厚检测仪检测蒸镀速度,用石英晶体振荡器检测薄膜厚度。
测试系统的说明:将测试软件、计算机、美国Keithley公司生产的K2400数字源表和美国Photo Research公司的PR788光谱扫描亮度计组成一个联合IVL测试系统来测试有机电致发光器件的驱动电压、发光效率等。
实施例1:有机电致发光器件1的制备
在ITO透明电极上热蒸镀HAT-CN作为空穴注入层,蒸镀厚度为10nm;在空穴注入层中热蒸镀NPB作为空穴传输层,蒸镀厚度为50nm;在空穴传输层上热蒸镀GH-1:GH-2:GD=47.5:47.5:5作为发光层,蒸镀厚度为30nm;在发光层上热蒸镀本发明的化合物1作为空穴阻挡层,蒸镀厚度为5nm;在空穴阻挡层上热蒸镀ET-1:Liq=50:50作为电子传输层,蒸镀厚度为30nm;在电子传输层上热蒸镀Liq作为电子注入层,蒸镀厚度为1nm;在电子注入层上热蒸镀Al作为阴极,蒸镀厚度为150nm。
有机电致发光器件1的器件结构如下:
ITO/HAT-CN(10nm)/NPB(50nm)/GH-1:GH-2:GD=47.5:47.5:5(30nm)/化合物1(5nm)/ET-1:Liq=50:50(30nm)/Liq(1nm)/Al(150nm)。
实施例2~11:有机电致发光器件2~11的制备
将实施例1中空穴阻挡层中的化合物1分别换成化合物6、化合物19、化合物22、化合物29、化合物37、化合物57、化合物77、化合物173、化合物219、化合物244,其它步骤相同,得到有机电致发光器件2~11。
实施例12:有机电致发光器件12的制备
在ITO透明电极上热蒸镀HAT-CN作为空穴注入层,蒸镀厚度为10nm;在空穴注入层中热蒸镀NPB作为空穴传输层,蒸镀厚度为50nm;在空穴传输层上热蒸镀本发明的化合物II-21作为发光辅助层,蒸镀厚度为10nm;在发光辅助层上热蒸镀GH-1:GH-2:GD=47.5:47.5:5作为发光层,蒸镀厚度为30nm;在发光层上热蒸镀本发明的化合物1作为空穴阻挡层,蒸镀厚度为5nm;在空穴阻挡层上热蒸镀ET-1:Liq=50:50作为电子传输层,蒸镀厚度为30nm;在电子传输层上热蒸镀Liq作为电子注入层,蒸镀厚度为1nm;在电子注入层上热蒸镀Al作为阴极,蒸镀厚度为150nm。
有机电致发光器件1的器件结构如下:
ITO/HAT-CN(10nm)/NPB(50nm)/化合物II-21(10nm)/GH-1:GH-2:GD=47.5:47.5:5(30nm)/化合物1(5nm)/ET-1:Liq=50:50(30nm)/Liq(1nm)/Al(150nm)。
实施例13~25:有机电致发光器件13~25的制备
将实施12中空穴阻挡层中的化合物1分别换成化合物42、化合物43、化合物51、化合物65、化合物71、化合物95、化合物102、化合物106、化合物108、化合物153、化合物164、化合物201、化合物250,发光辅助层中的化合物II-21分别换成化合物II-102、化合物II-1、化合物II-47、化合物II-70、化合物II-119、化合物II-85、化合物II-77、化合物II-79、化合物II-76、化合物II-159、化合物II-90、化合物II-73、化合物II-78,其它步骤相同,得到有机电致发光器件13~25。
对比例1~3:对比有机电致发光器件1~3的制备
将实施例1中空穴阻挡层中的化合物1分别换成化合物R-1、化合物R-2、化合物R-3,其它步骤相同,得到对比有机电致发光器件1~3。
对比例4~6:对比有机电致发光器件4~6的制备
将实施例12中空穴阻挡层中的化合物1分别换成化合物1、化合物R-1、化合物R-1,发光辅助层中的化合物II-1分别换成化合物HT-1、化合物HT-2、化合物HT-2,其它步骤相同,得到对比有机电致发光器件4~6。
本发明实施例1~25以及对比例1~6制备的有机电致发光器件的发光特性测试结果如表1所示。
表1有机电致发光器件的发光特性测试数据
从表1中可以看出,器件1~11与对比器件1~3相比,具有较低的驱动电压与较高的发光效率。这说明本发明式I的杂环衍生物具有较好的电子迁移率以及较好的空穴阻挡性能,能将空穴有效的阻挡在发光层内,使电子和空穴能够在发光层内有效形成激子。
相比于对比器件4~6,有机电致发光器件12~25的驱动电压更低、发光效率更高。这说明本发明式II所示的三芳胺化合物的空穴迁移率较高,能够有效的传输空穴,同时还表明含有式I的杂环衍生物的空穴阻挡层所在的电子传输区域与含有式II的三芳胺化合物的发光辅助层所在的空穴传输区域对电子和空穴的注入与传输更加的平衡,减少了激子的淬灭,提高了载流子的复合几率,故器件的驱动电压更低、发光效率更高。
应当指出,本发明用个别实施方案进行了特别描述,但在不脱离本发明原理的前提下,本领域普通技术人可对本发明进行各种形式或细节上的改进,这些改进也落入本发明的保护范围内。
Claims (10)
1.一种杂环衍生物,其特征在于,具有如式I所示的结构通式,
所述Ar1、Ar2相同或者不同,选自如下所示基团,
所述R0选自氢、氘、卤素、氰基、硝基、取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种,
所述X0选自O、S、N(Rx)、C(Rx)2中的一种,所述Rx选自取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种,
所述Z选自C(Ry)或N,所述Ry选自氢、氘、卤素、氰基、硝基、取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C2~C30的烯基、取代或未取代的C2~C30的炔基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种,或者相邻两个基团之间连接成环;
所述X选自O、S、N(Ar)、C(Ar)2、Si(Ar)2中的一种,所述Ar选自取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种;
所述m选自0、1、2、3或者4,所述R相同或者不同的选自氘、氰基、硝基、取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C2~C30的烯基、取代或未取代的C2~C30的炔基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种,或者相邻两个基团之间连接成环;
所述Lx、Ly独立的选自单键、取代或未取代的C1~C30的亚烷基、取代或未取代的C1~C30的亚环烷基、取代或未取代的C6~C60的亚芳基、取代或未取代的C3~C60的亚杂芳基中的一种;
所述L1、L2独立的选自单键、取代或未取代的C6~C60的亚芳基、取代或未取代的C3~C60的亚杂芳基中的一种。
2.根据权利要求1所述的杂环衍生物,其特征在于,所述Lx、Ly独立的选自单键、取代或未取代的亚金刚烷基、取代或未取代的亚莰烷基、亚降冰片烷基、取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚萘基、取代的或未取代的亚菲基、取代或未取代的亚三亚苯基、取代或未取代的亚芴基、取代或未取代的亚苯并芴基、取代或未取代的亚螺二芴基、取代或未取代的亚苯并螺二芴基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚咔唑基、取代或未取代的亚喹啉基、取代或未取代的亚异喹啉基、取代或未取代的萘啶基、取代或未取代的亚喹喔啉基、取代或未取代的亚喹唑啉基、取代或未取代的亚菲啰啉基中的一种;
所述L1、L2独立的选自单键或者如下所示基团中的一种,
所述T相同或者不同的选自N或者C(Rm),所述Rm选自氢、氘、氰基、硝基、取代或未取代的C1~C30的烷基、取代或未取代的C3~C30的环烷基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种;
所述Y选自O、S、N(Rn)、C(Rn)2中的一种,所述Rn选自氢、氘、取代或未取代的C1~C30的烷基、取代或未取代的C1~C30的环烷基、取代或未取代的C2~C30的烯基、取代或未取代的C2~C30的炔基、取代或未取代的C6~C60的芳基、取代或未取代的C3~C60的杂芳基中的一种,或者相邻两个基团连接成环;
所述L0相同或者不同的选自单键、取代或未取代的C6~C60的亚芳基、取代或未取代的C3~C60的亚杂芳基中的一种。
6.一种有机电致发光器件,其特征在于,包括阳极、有机物层、阴极,所述有机物层位于阳极和阴极之间,所述有机物层包括电子传输区域,所述电子传输区域含有权利要求1~5任一项所述的杂环衍生物。
7.根据权利要求6所述的有机电致发光器件,其特征在于,所述有机物层还包括空穴传输区域,所述空穴传输区域含有式II所示的三芳胺化合物,
其中,A、B独立的选自如下取代基中的一种:
其中,所述Ra相同或不同地选自氢、氘、取代或未取代的C1~C15的烷基、取代或未取代的C3~C15的环烷基、取代或未取代的C2~C30的烯基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种,或者相邻的两个基团连接成环;
所述Rb相同或不同地选自氢、氘、取代或未取代的C1~C15的烷基、取代或未取代的C3~C15的环烷基、取代或未取代的C2~C30的烯基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种,或者相邻的两个基团连接成环;
所述La选自单键、取代或未取代的C6~C30的亚芳基、取代或未取代的C3~C30的亚杂芳基中的一种;
所述a选自0、1、2、3或者4,所述b选自0、1、2、3、4或者5;
所述C选自如下基团中的一种:
其中,所述R12选自甲基、乙基、丙基、丁基、苯基、甲苯基、联苯基、萘基中的一种;
所述R13选自氘、甲基、乙基、丙基、丁基、环己基、金刚烷基、苯基、甲苯基、联苯基、三联苯基、萘基、蒽基、菲基、三亚苯基、吖啶基、螺二芴基、9,9-二甲基芴基、9,9-二苯基芴基、9-苯基咔唑基、芘基、吲哚基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基中的一种;
所述Lb选自单键、亚苯基、亚氘代苯基、亚氘代萘基、亚甲苯基、亚联苯基、亚萘基、亚三联苯基、亚二苯并呋喃基、亚芴基、亚二苯并噻吩基中的一种;
所述c选自0、1、2、3、4或者5;d选自0、1、2、3或者4;e选自0、1、2、3、4、5、6或者7;f选自0、1、2、3、4、5、6、7、8或者9。
9.根据权利要求7所述的一种有机电致发光器件,其特征在于,所述Ra独立的选自氢、氘、甲基、乙基、丙基、丁基、金刚烷基、莰烷基、降冰片烷基、苯基、甲苯基、联苯基、三联苯基、萘基、蒽基、菲基、三亚苯基、吖啶基、螺二芴基、9,9-二甲基芴基、9,9-二苯基芴基、9-苯基咔唑基、芘基、吲哚基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基中的一种,或者相邻两个基团之间连接成环;
所述La选自单键、亚苯基、亚甲苯基、亚联苯基、亚萘基、亚三联苯基、亚二苯并呋喃基、亚芴基、亚二苯并噻吩基中的一种;
所述Rb相同或不同地选自氢、氘、甲基、乙基、丙基、丁基、金刚烷基、莰烷基、降冰片烷基、苯基、甲苯基、联苯基、三联苯基中的一种,或者相邻两个基团之间连接成环。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011377608.8A CN112442023B (zh) | 2020-11-30 | 2020-11-30 | 一种杂环衍生物及其有机电致发光器件 |
EP21208948.6A EP4006025A1 (en) | 2020-11-30 | 2021-11-18 | Heterocyclic derivative and organic electroluminescent device thereof |
US17/535,110 US20220173333A1 (en) | 2020-11-30 | 2021-11-24 | Heterocyclic derivative and organic electroluminescent device thereof |
JP2021192199A JP7262138B2 (ja) | 2020-11-30 | 2021-11-26 | 複素環誘導体及びその有機電界発光素子 |
KR1020210167964A KR20220077093A (ko) | 2020-11-30 | 2021-11-30 | 헤테로고리 유도체 및 이의 유기 전계발광소자 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011377608.8A CN112442023B (zh) | 2020-11-30 | 2020-11-30 | 一种杂环衍生物及其有机电致发光器件 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN112442023A true CN112442023A (zh) | 2021-03-05 |
CN112442023B CN112442023B (zh) | 2021-08-24 |
Family
ID=74739106
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202011377608.8A Active CN112442023B (zh) | 2020-11-30 | 2020-11-30 | 一种杂环衍生物及其有机电致发光器件 |
Country Status (5)
Country | Link |
---|---|
US (1) | US20220173333A1 (zh) |
EP (1) | EP4006025A1 (zh) |
JP (1) | JP7262138B2 (zh) |
KR (1) | KR20220077093A (zh) |
CN (1) | CN112442023B (zh) |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112939788A (zh) * | 2021-03-01 | 2021-06-11 | 浙江虹舞科技有限公司 | 一种金刚烷胺类化合物及其应用以及包含该化合物的有机电致发光器件 |
CN113582854A (zh) * | 2021-07-30 | 2021-11-02 | 上海钥熠电子科技有限公司 | 新型化合物及其在有机电致发光显示器件中的应用 |
CN113683630A (zh) * | 2021-09-24 | 2021-11-23 | 长春海谱润斯科技股份有限公司 | 一种含氮杂环衍生物及其有机电致发光器件 |
CN113717153A (zh) * | 2021-09-18 | 2021-11-30 | 长春海谱润斯科技股份有限公司 | 一种螺环类化合物及其有机发光器件 |
CN113735780A (zh) * | 2021-09-26 | 2021-12-03 | 长春海谱润斯科技股份有限公司 | 一种苯并五元杂环衍生物及其有机电致发光器件 |
CN113735793A (zh) * | 2021-09-24 | 2021-12-03 | 长春海谱润斯科技股份有限公司 | 一种包含苯并五元杂环的化合物及其有机电致发光器件 |
CN113845512A (zh) * | 2021-09-18 | 2021-12-28 | 长春海谱润斯科技股份有限公司 | 一种包含杂环的化合物及其有机电致发光器件 |
CN114105891A (zh) * | 2021-12-02 | 2022-03-01 | 长春海谱润斯科技股份有限公司 | 一种芴衍生物及其有机电致发光器件 |
CN114835591A (zh) * | 2022-06-02 | 2022-08-02 | 南京高光半导体材料有限公司 | 一种含有环烷基团的化合物及有机电致发光器件 |
CN115093332A (zh) * | 2021-07-01 | 2022-09-23 | 四川阿格瑞新材料有限公司 | 一种螺环化合物及其应用 |
WO2022230972A1 (ja) * | 2021-04-28 | 2022-11-03 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 |
CN115433198A (zh) * | 2021-06-03 | 2022-12-06 | 宁波卢米蓝新材料有限公司 | 一种杂环化合物及其应用 |
TWI819766B (zh) * | 2021-09-28 | 2023-10-21 | 大陸商四川阿格瑞新材料有限公司 | 一種螺環化合物及其應用 |
TWI843125B (zh) | 2021-07-01 | 2024-05-21 | 大陸商四川阿格瑞新材料有限公司 | 一種螺環化合物及其應用 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112661714B (zh) * | 2020-12-22 | 2022-01-07 | 长春海谱润斯科技股份有限公司 | 一种杂环化合物和包含该杂环化合物的有机电致发光器件 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6171715B1 (en) * | 1997-08-07 | 2001-01-09 | Fuji Photo Film Co., Ltd. | Organic electroluminescent element |
US20150318510A1 (en) * | 2014-05-02 | 2015-11-05 | Samsung Display Co., Ltd. | Organic light-emitting device |
US20150318487A1 (en) * | 2014-05-02 | 2015-11-05 | Samsung Display Co., Ltd. | Organic light-emitting device |
CN106536485A (zh) * | 2014-07-21 | 2017-03-22 | 默克专利有限公司 | 用于电子器件的材料 |
CN109206420A (zh) * | 2017-12-14 | 2019-01-15 | 江苏三月光电科技有限公司 | 一种基于三嗪的有机化合物及其在有机电致发光器件上的应用 |
CN111253332A (zh) * | 2018-11-30 | 2020-06-09 | 江苏三月光电科技有限公司 | 一种有机化合物及其制备方法和在oled上的应用 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4843889B2 (ja) | 2001-09-26 | 2011-12-21 | 東レ株式会社 | 発光素子 |
CN104193738B (zh) * | 2014-08-21 | 2016-05-18 | 上海道亦化工科技有限公司 | 一种基于苯并咪唑的电子传输化合物 |
KR102144173B1 (ko) | 2017-09-19 | 2020-08-12 | 주식회사 엘지화학 | 유기 발광 소자 |
-
2020
- 2020-11-30 CN CN202011377608.8A patent/CN112442023B/zh active Active
-
2021
- 2021-11-18 EP EP21208948.6A patent/EP4006025A1/en active Pending
- 2021-11-24 US US17/535,110 patent/US20220173333A1/en active Pending
- 2021-11-26 JP JP2021192199A patent/JP7262138B2/ja active Active
- 2021-11-30 KR KR1020210167964A patent/KR20220077093A/ko not_active Application Discontinuation
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6171715B1 (en) * | 1997-08-07 | 2001-01-09 | Fuji Photo Film Co., Ltd. | Organic electroluminescent element |
US20150318510A1 (en) * | 2014-05-02 | 2015-11-05 | Samsung Display Co., Ltd. | Organic light-emitting device |
US20150318487A1 (en) * | 2014-05-02 | 2015-11-05 | Samsung Display Co., Ltd. | Organic light-emitting device |
CN106536485A (zh) * | 2014-07-21 | 2017-03-22 | 默克专利有限公司 | 用于电子器件的材料 |
CN109206420A (zh) * | 2017-12-14 | 2019-01-15 | 江苏三月光电科技有限公司 | 一种基于三嗪的有机化合物及其在有机电致发光器件上的应用 |
CN111253332A (zh) * | 2018-11-30 | 2020-06-09 | 江苏三月光电科技有限公司 | 一种有机化合物及其制备方法和在oled上的应用 |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112939788A (zh) * | 2021-03-01 | 2021-06-11 | 浙江虹舞科技有限公司 | 一种金刚烷胺类化合物及其应用以及包含该化合物的有机电致发光器件 |
WO2022230972A1 (ja) * | 2021-04-28 | 2022-11-03 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 |
CN115433198B (zh) * | 2021-06-03 | 2023-12-08 | 宁波卢米蓝新材料有限公司 | 一种杂环化合物及其应用 |
CN115433198A (zh) * | 2021-06-03 | 2022-12-06 | 宁波卢米蓝新材料有限公司 | 一种杂环化合物及其应用 |
CN115093332A (zh) * | 2021-07-01 | 2022-09-23 | 四川阿格瑞新材料有限公司 | 一种螺环化合物及其应用 |
TWI843125B (zh) | 2021-07-01 | 2024-05-21 | 大陸商四川阿格瑞新材料有限公司 | 一種螺環化合物及其應用 |
WO2023273846A1 (zh) * | 2021-07-01 | 2023-01-05 | 四川阿格瑞新材料有限公司 | 一种螺环化合物及其应用 |
CN113582854A (zh) * | 2021-07-30 | 2021-11-02 | 上海钥熠电子科技有限公司 | 新型化合物及其在有机电致发光显示器件中的应用 |
CN113582854B (zh) * | 2021-07-30 | 2024-01-26 | 上海钥熠电子科技有限公司 | 化合物及其在有机电致发光显示器件中的应用 |
CN113845512A (zh) * | 2021-09-18 | 2021-12-28 | 长春海谱润斯科技股份有限公司 | 一种包含杂环的化合物及其有机电致发光器件 |
CN113717153A (zh) * | 2021-09-18 | 2021-11-30 | 长春海谱润斯科技股份有限公司 | 一种螺环类化合物及其有机发光器件 |
CN113683630A (zh) * | 2021-09-24 | 2021-11-23 | 长春海谱润斯科技股份有限公司 | 一种含氮杂环衍生物及其有机电致发光器件 |
CN113735793B (zh) * | 2021-09-24 | 2022-12-13 | 长春海谱润斯科技股份有限公司 | 一种包含苯并五元杂环的化合物及其有机电致发光器件 |
CN113735793A (zh) * | 2021-09-24 | 2021-12-03 | 长春海谱润斯科技股份有限公司 | 一种包含苯并五元杂环的化合物及其有机电致发光器件 |
CN113683630B (zh) * | 2021-09-24 | 2024-01-26 | 长春海谱润斯科技股份有限公司 | 一种含氮杂环衍生物及其有机电致发光器件 |
CN113735780B (zh) * | 2021-09-26 | 2024-04-05 | 长春海谱润斯科技股份有限公司 | 一种苯并五元杂环衍生物及其有机电致发光器件 |
CN113735780A (zh) * | 2021-09-26 | 2021-12-03 | 长春海谱润斯科技股份有限公司 | 一种苯并五元杂环衍生物及其有机电致发光器件 |
TWI819766B (zh) * | 2021-09-28 | 2023-10-21 | 大陸商四川阿格瑞新材料有限公司 | 一種螺環化合物及其應用 |
CN114105891B (zh) * | 2021-12-02 | 2024-01-26 | 长春海谱润斯科技股份有限公司 | 一种芴衍生物及其有机电致发光器件 |
CN114105891A (zh) * | 2021-12-02 | 2022-03-01 | 长春海谱润斯科技股份有限公司 | 一种芴衍生物及其有机电致发光器件 |
CN114835591A (zh) * | 2022-06-02 | 2022-08-02 | 南京高光半导体材料有限公司 | 一种含有环烷基团的化合物及有机电致发光器件 |
Also Published As
Publication number | Publication date |
---|---|
JP7262138B2 (ja) | 2023-04-21 |
US20220173333A1 (en) | 2022-06-02 |
KR20220077093A (ko) | 2022-06-08 |
CN112442023B (zh) | 2021-08-24 |
JP2022087059A (ja) | 2022-06-09 |
EP4006025A1 (en) | 2022-06-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN112442023B (zh) | 一种杂环衍生物及其有机电致发光器件 | |
CN112961147B (zh) | 一种含氮化合物及其有机电致发光器件 | |
CN112341449A (zh) | 一种含螺芴的三芳胺类有机化合物及其有机发光器件 | |
CN112079730B (zh) | 一种含氮化合物以及使用其的电子元件和电子装置 | |
CN111606812B (zh) | 一种三芳胺衍生物及其有机电致发光器件 | |
CN113906582A (zh) | 有机发光器件 | |
CN114989069B (zh) | 含氮化合物和电子元件及电子装置 | |
CN116640126A (zh) | 一种有机电致发光化合物及其有机电致发光器件 | |
CN113735809B (zh) | 一种芳胺衍生物及其有机电致发光器件 | |
CN114456161A (zh) | 一种咪唑衍生物及其有机电致发光器件 | |
CN113735780A (zh) | 一种苯并五元杂环衍生物及其有机电致发光器件 | |
CN107226799B (zh) | 有机化合物及有机光电装置及显示装置 | |
CN117126149A (zh) | 一种杂环化合物及其有机电致发光器件 | |
CN114621181B (zh) | 一种星型四胺衍生物及其有机电致发光器件 | |
CN111004207A (zh) | 有机化合物、电子器件及电子装置 | |
CN113666921B (zh) | 一种杂环类化合物及其有机电致发光器件 | |
CN111785849B (zh) | 一种含有覆盖层的顶发射有机电致发光器件 | |
CN111848493B (zh) | 一种含有螺二芴的衍生物及其有机电致发光器件 | |
CN115521242A (zh) | 有机化合物和电子元件及电子装置 | |
CN113582986B (zh) | 螺环类化合物及其制备方法、发光辅助材料和有机电致发光器件 | |
CN115304615B (zh) | 杂环化合物及有机电致发光器件和电子装置 | |
CN116903561A (zh) | 一种三胺衍生物及其有机电致发光器件 | |
CN117430480A (zh) | 有机化合物及包含其的电子元件和电子装置 | |
CN117143134A (zh) | 一种联咔唑类化合物及其有机电致发光器件 | |
CN116396253A (zh) | 含氮化合物和电子元件及电子装置 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |