CN106542956A - 有机化合物及使用其的有机电激发光元件 - Google Patents
有机化合物及使用其的有机电激发光元件 Download PDFInfo
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- CN106542956A CN106542956A CN201610751176.XA CN201610751176A CN106542956A CN 106542956 A CN106542956 A CN 106542956A CN 201610751176 A CN201610751176 A CN 201610751176A CN 106542956 A CN106542956 A CN 106542956A
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- electroluminescent element
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- 150000002894 organic compounds Chemical class 0.000 title abstract description 27
- 239000000463 material Substances 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000010409 thin film Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000010408 film Substances 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 67
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 17
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 125000005580 triphenylene group Chemical group 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- 230000004888 barrier function Effects 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 238000007872 degassing Methods 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
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- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- -1 pinacol borates Chemical class 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000027756 respiratory electron transport chain Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- 235000010290 biphenyl Nutrition 0.000 description 5
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 5
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- HYCYKHYFIWHGEX-UHFFFAOYSA-N (2-phenylphenyl)boronic acid Chemical class OB(O)C1=CC=CC=C1C1=CC=CC=C1 HYCYKHYFIWHGEX-UHFFFAOYSA-N 0.000 description 3
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- 239000010453 quartz Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- MNKJQJJUQKPGDJ-UHFFFAOYSA-N 1,2-dibromo-9,9-dimethylfluorene Chemical class C1=C(Br)C(Br)=C2C(C)(C)C3=CC=CC=C3C2=C1 MNKJQJJUQKPGDJ-UHFFFAOYSA-N 0.000 description 2
- KMZUUSFWPQLMQE-UHFFFAOYSA-N 1-bromo-9,9-dimethylfluorene Chemical class C1=CC(Br)=C2C(C)(C)C3=CC=CC=C3C2=C1 KMZUUSFWPQLMQE-UHFFFAOYSA-N 0.000 description 2
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 2
- 229920001621 AMOLED Polymers 0.000 description 2
- FRYRJNHMRVINIZ-UHFFFAOYSA-N B1CCOO1 Chemical class B1CCOO1 FRYRJNHMRVINIZ-UHFFFAOYSA-N 0.000 description 2
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- IVDFJHOHABJVEH-UHFFFAOYSA-N HOCMe2CMe2OH Natural products CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical class [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000007769 metal material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- UBHOJJRMAHJLMR-UHFFFAOYSA-N 1-n,1-n,6-n,6-n-tetrakis(3-methylphenyl)pyrene-1,6-diamine Chemical compound CC1=CC=CC(N(C=2C=C(C)C=CC=2)C=2C3=CC=C4C=CC(=C5C=CC(C3=C54)=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 UBHOJJRMAHJLMR-UHFFFAOYSA-N 0.000 description 1
- OZZBPFWQVSIKNW-UHFFFAOYSA-N 10,10-dimethyl-(10h-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC(C)(C)C2=C(C=C3C(C4=CC=CC=C4C4=CC=CC=C43)=C3)C3=CC2=C1 OZZBPFWQVSIKNW-UHFFFAOYSA-N 0.000 description 1
- ITRVPNWYQDFJGA-UHFFFAOYSA-N 2-(18,18-dimethyl-20-hexacyclo[12.11.0.02,7.08,13.016,24.017,22]pentacosa-1(25),2,4,6,8,10,12,14,16,19,21,23-dodecaenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound CC1(C=C(C=C2C=C3C=C4C=5C=CC=CC5C=5C=CC=CC5C4=CC3=C12)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1)C ITRVPNWYQDFJGA-UHFFFAOYSA-N 0.000 description 1
- OSOOKMFTQZQPHA-UHFFFAOYSA-N 2-(18,18-dimethyl-21-hexacyclo[12.11.0.02,7.08,13.016,24.017,22]pentacosa-1(25),2,4,6,8,10,12,14,16,19,21,23-dodecaenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C=CC(=C2C=C3C=C4C=5C=CC=CC=5C=5C=CC=CC=5C4=CC3=C12)B1OC(C(O1)(C)C)(C)C)C OSOOKMFTQZQPHA-UHFFFAOYSA-N 0.000 description 1
- CMAAMONCFHBJSP-UHFFFAOYSA-N 2-(18,18-dimethyl-21-hexacyclo[12.11.0.02,7.08,13.016,24.017,22]pentacosa-1(25),2,4,6,8,10,12,14,16,19,21,23-dodecaenyl)-9-phenyl-1,10-phenanthroline Chemical compound CC1(C=CC(=C2C=C3C=C4C=5C=CC=CC5C=5C=CC=CC5C4=CC3=C12)C1=NC2=C3N=C(C=CC3=CC=C2C=C1)C1=CC=CC=C1)C CMAAMONCFHBJSP-UHFFFAOYSA-N 0.000 description 1
- HSTYNNOCIACBOP-UHFFFAOYSA-N 2-bromo-9,9-dimethyl-7-(2-phenylphenyl)fluorene Chemical compound C1=C2C(C)(C)C3=CC(Br)=CC=C3C2=CC=C1C1=CC=CC=C1C1=CC=CC=C1 HSTYNNOCIACBOP-UHFFFAOYSA-N 0.000 description 1
- RLPAWKJLZUFLCR-UHFFFAOYSA-N 4-(4-aminophenyl)-3-naphthalen-1-yl-n,n-diphenylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1C1=CC=CC2=CC=CC=C12 RLPAWKJLZUFLCR-UHFFFAOYSA-N 0.000 description 1
- LOIBXBUXWRVJCF-UHFFFAOYSA-N 4-(4-aminophenyl)-3-phenylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1C1=CC=CC=C1 LOIBXBUXWRVJCF-UHFFFAOYSA-N 0.000 description 1
- FJJAUFLPJSWZRV-UHFFFAOYSA-N 6-bromo-9,9-dimethyl-2-(2-phenylphenyl)fluorene Chemical compound C1(=C(C=CC=C1)C1=CC=2C(C3=CC=C(C=C3C=2C=C1)Br)(C)C)C1=CC=CC=C1 FJJAUFLPJSWZRV-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
- MATLAXFLOYGEOI-UHFFFAOYSA-N 9,9-dimethyl-N-(4-phenylphenyl)-N-[4-(4-phenylphenyl)phenyl]fluoren-2-amine Chemical compound C1(=CC=C(C=C1)N(C1=CC=2C(C3=CC=CC=C3C=2C=C1)(C)C)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC=CC=C1 MATLAXFLOYGEOI-UHFFFAOYSA-N 0.000 description 1
- LMTXHBDTVAIIQY-UHFFFAOYSA-N 9-n,10-n-bis(3-methylphenyl)-9-n,10-n-diphenylanthracene-9,10-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C(N(C=3C=CC=CC=3)C=3C=C(C)C=CC=3)=C3C=CC=CC3=2)=C1 LMTXHBDTVAIIQY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 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 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical group Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000012806 monitoring device Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/357—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by dehydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- C—CHEMISTRY; METALLURGY
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Abstract
本发明提供一种有机化合物以及使用此有机化合物的有机电激发光(以下称为有机EL)元件。更具体的是,本发明关于一种有机化合物以及应用此有机化合物于荧光发光层的有机EL元件,前述有机EL元件可具有长寿命、高效率,并且发出蓝色荧光及绿色荧光。
Description
技术领域
本发明一般关于一种有机化合物以及关于此化合物的有机电激发光(以下称为“有机EL”)元件。具体而言,本发明关于一种有机化合物以及一种应用前述有机化合物于荧光发光层中的有机电激发光元件及其相关装置、平板等,而可表现长半衰期时间、高效率且可发射蓝光。
背景技术
有机EL元件具有诸如自发射、较宽视角、较快回应速度及高发光的许多优点。其制造方式较简单且能够提供与LCD相当的清晰显示,使得有机EL元件成为工业显示器的一选择。有机EL包含有设置在阳极与阴极之间的发光材料,当对其施加一驱动电压时,电子和电洞会注入发光层中且重组形成激子(exciton)。由电子和电洞的重组而形成的激子具有单重自旋态(singlet spin state)或三重自旋态(triplet spin state)。自单重自旋态发射的光线为荧光(fluorescence),而自三重自旋态发射的光线为磷光(phosphorescence)。
有机EL一般是由功能性区分的数个有机材料层所构成,例如:电洞注入层(holeinjection layer,HIL)、电洞传输层(hole transporting layer,HTL)、发光层(emittinglayer,EML)、电子传输层(electron transporting layer,ETL)以及电子注入层(electroninjection layer,EIL)等等。具有良好的电荷载子移动性(charge carrier mobility)以及优异的操作耐受性(operational durability)的发光材料可以降低有机EL元件的驱动电压、功率消耗,并且增加效率以及半衰期时间。
对于自动矩阵式有机发光二极体(active-matrix organic light-emittingdiode,AMOLED)的全彩式面板显示器(full-colored flat panel display)而言,其半衰期时间及效率方面,效果仍不尽理想。许多化合物可应用于发光层中的蓝色荧光主体。美国专利案第5,935,721号公开9,10-二(萘-2-基)蒽(9,10-di(naphthalen-2-yl)anthracene,AND)用于发光层的蓝光主体。美国专利案7,691,492号公开1,1-(9,9-二甲基-9H-芴-2,7-二基)二芘(1,1-(9,9-dimethyl-9H-fluorene-2,7-diyl)dipyrene,DFDP)用于蓝光有机EL元件的主体。上述这些化合物对于工业实践上仍有缺失。
在本发明的发明人过去的发明中,参见美国专利案第9,048,437号,颜等人(Yenet al.)使用茚并三亚苯骨架连结至经杂芳基取代的萘蒽基团以完成蓝色荧光化合物。在本发明中,为了延长蓝色荧光有机EL元件的半衰期时间且改善效率,采用茚并三亚苯骨架连结至二至四个环的稠环碳氢单元所取代的苯蒽基团可表现比先前发明较高的半衰期时间以及效率。
发明内容
依据本发明,提供一种新颖的有机化合物,此化合物可用于有机EL元件中。前述有机化合物能够克服现有技术的材料的缺失,诸如短半衰期时间、低效率,特别是本发明中所述的蓝色荧光发光化合物。以全彩平面显示器而言,由于短半衰期时间及效率的因素,蓝色发光材料在实际应用上仍然不理想。
本发明的一目的是提供一种有机化合物,其可以用于有机EL元件中的发光材料或其它具有类似功能的材料。
本发明的另一目的是提供一种有机化合物,其可以用作有机EL元件中蓝色荧光发光材料或其它具有类似功能的材料,以便增进元件的半衰期时间及效率。
本发明的又一目的是提供一种有机电激发光元件,其包括如下所述的化合物。本发明的有机电激发光元件可广泛地应用或设置于各种具备有机发光功能的有机发光装置(organic light emitting device),或者应用于发光平板(lighting panel)以及/或背光平板(backlight panel)中。
本发明在工业实践上具有经济优势。据此,提供一种用于有机EL元件的有机化合物,此有机化合物包括如下式(I)所示的结构:
其中A表示具有二至四个环的经取代或未经取代的稠环碳氢单元(fused ringhydrocarbon unit),R1至R3独立地表示选自于由氢原子(hydrogen atom)、卤素(halide)、具有1至30个碳原子的经取代或未经取代的烷基(alkyl group)、具有6至30个碳原子的经取代或未经取代的芳基(aryl group)以及具有6至30个碳原子的经取代或未经取代的芳烷基(aralkyl group)所组成的群组。
本发明另提供一种有机电激发光元件,其包括一对电极、至少一发光层以及一个或多个有机薄膜层,其中对电极由阴极和阳极所组成,发光层及有机薄膜层均设置于对电极的阴极和阳极之间,且在发光层的至少一层包括如前所述的有机化合物。
在发光层中所包含的前述有机化合物亦可用作发光主体材料(host material);或者,亦可用作荧光发射体(fluorescent emitter)。此外,发光层所发出的光可为蓝光或绿光。
本发明再提供一种有机发光装置(organic light emitting device),其包括如前所述的有机电激发光元件。
本发明又提供一种发光平板(lighting panel),其包括如前所述的有机电激发光元件。
本发明又再提供一种背光平板(backlight panel),其包括如前所述的有机电激发光元件。
附图说明
图1显示本发明的有机EL元件的一实施例的示意图;
附图符号说明:
6透明电极,7电洞注入层,8电洞传输层,9电子阻挡层,10发光层,11电洞阻挡层,12电子传输层,13电子注入层,14金属电极。
具体实施方式
本发明欲探究的是一种有机化合物以及一种使用此有机化合物的有机EL元件。在下文中将提供生产、结构以及要素的详细描述以充分理解本发明。明显地是,本发明的应用不限于本领域的普通技术人员所熟悉的特定细节。另一方面,已知的常见要素和程序并未详细描述于本发明中,且不应对本发明产生不必要的限制。现将在下文中更详细地描述本发明的一些较佳实施例。但是,应认识到本发明可以在除了明确描述的实施例之外的多种其它实施例中广泛实践,即,本发明还可以广泛应用于其它实施例,并且除了如所附权利要求书中所指定外,本发明的范围不受明确限制。
本发明提供一种有机化合物,其具有如式(I)所示的结构,此有机化合物可以用于有机EL元件的发光层中的发光材料,在一较佳实施例中,此有机化合物可以用于有机EL元件的发光层中的蓝色荧光材料。式(I)结构如下:
其中A表示具有二至四个环的经取代或未经取代的稠环碳氢单元,R1至R3独立地表示选自于由氢原子、卤素、具有1至30个碳原子的经取代或未经取代的烷基、具有6至30个碳原子的经取代或未经取代的芳基以及具有6至30个碳原子的经取代或未经取代的芳烷基所组成的群组。
在一些较佳实施例中,根据前述式(I)所示的有机化合物,可进一步表示为由选自于下列通式所示结构所组成的群组中的其中一种:
另一方面,本发明述及一种有机电激发光元件,其可包括一对由阴极和阳极所组成的对电极、至少一发光层以及一个或多个有机薄膜层,发光层及有机薄膜层均设置于所述对电极的阴极和阳极之间,且发光层的至少一层包含有本发明的有机化合物。
请参阅图1所示,在一较佳实施例中,此种有机电激发光元件的可包括透明电极6、电洞注入层7、电洞传输层8、电子阻挡层9、发光层10、电洞阻挡层11、电子传输层12、电子注入层13以及金属电极14。在元件中,电洞注入层7设置于透明电极6与金属电极14之间,电洞传输层8设置于电洞注入层7与金属电极14之间,电子阻挡层9设置于电洞传输层8与金属电极14之间,发光层10设置于电子阻挡层9与金属电极14之间,电洞阻挡层11设置于发光层10与金属电极14之间,电子传输层12设置于电洞阻挡层11与金属电极14之间,且电子注入层13设置于电子传输层12与金属电极14之间。此外,前述发光层可发出磷光、荧光,或其它可经有机材料电性激发产生的光线;在一较佳实施例中,自发光层所发出的荧光可以是荧光;在一较佳实施例中,自发光层所发出的荧光可以是蓝色荧光。
本发明所述的有机材料,其详细制备可以通过例示性实施例阐明,但不限于例示性实施例。实例1至4显示本发明中的化合物的一些实例的制备。实例5显示有机EL元件的制造和有机EL元件测试报告的I-V-B、半衰期时间。
实例1:化合物EX2的合成
合成2-(联苯-2-基)-7-溴-9,9-二甲基-9H-芴(2-(biphenyl-2-yl)-7-bromo-9,9-dimethyl-9H-fluorene)
将35.2g(100mmol)2,7-二溴-9,9-二甲基-9H-芴(2,7-dibromo-9,9-dimethyl-9H-fluorene)、21.8g(110mmol)联苯-2-基硼酸(biphenyl-2-ylboronic acid)、2.31g(2mmol)四(三苯基膦)钯(tetrakis(triphenylphosphine)palladium,Pd(PPh3)4)、75mL 2M碳酸钠(Na2CO3)、150mL乙醇(EtOH)以及300mL甲苯(toluene)的混合物经过脱气处理并且放置在氮气下,随后在100℃下加热12小时进行反应。将反应完成后的混合物冷却至室温,再利用乙酸乙酯和水萃取出有机层,将萃取出的有机层用无水硫酸镁进行干燥以去除溶剂,形成残余物。通过以硅胶填充的管柱层析来纯化残余物,得到26.8g(63.0mmol)产物,产率为63%。
合成12-溴-10,10-二甲基-10H-茚并[2,1-b]三亚苯(12-bromo-10,10-dimethyl-10H-indeno[2,1-b]triphenylene)
在经过脱气及填充氮气的3000mL三颈烧瓶中,将26.8g(60mmol)2-(联苯-2-基)-7-溴-9,9-二甲基-9H-芴溶解于无水二氯甲烷(1500mL)中,随后添加97.5g(600mmol)氯化铁(III)(Iron(III)chloride)形成混合物,搅拌混合物一小时,在搅拌后的混合物中添加500mL甲醇并且分离出有机层。在真空中将有机层去除溶剂,形成残余物,通过以硅胶填充的管柱层析(己烷-二氯甲烷)来纯化残余物,得到10.7g(25.3mmol)白色固体产物,产率为40%。1HNMR(CDCl3,400MHz):化学位移(ppm)8.95(s,1H),8.79-8.74(m,2H),8.69-8.68(m,3H),7.84(d,J=8.0Hz,1H),7.72-7.65(m,5H),7.57(d,J=8.0Hz,1H),1.66(s,6H).
合成2-(10,10-二甲基-10H-茚并[2,1-b]三亚苯-12-基)-4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷(2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
将10.7g(25.3mmol)12-溴-10,10-二甲基-10H-茚并-[1,2-b]三亚苯、7.7g(30.3mmol)双频哪醇硼酸酯(bis(pinacolato)diboron)、0.3g(0.26mmol)四(三苯基膦)钯、7.4g(75.4mmol)醋酸钾(potassium acetate)以及300mL1,4-二恶烷(1,4-dioxane)的混合物经过脱气处理并且放置在氮气下,随后在90℃下加热16小时进行反应。将反应完成后的混合物冷却至室温,再利用乙酸乙酯和水分离洗出有机层,将有机层用无水硫酸镁进行干燥,在真空环境下去除溶剂,形成残余物。通过以硅胶填充的管柱层析(己烷-二氯甲烷)纯化残余物,得到6.4g(13.7mmol)淡黄色固体产物,产率为54%。1HNMR(CDCl3,400MHz):化学位移(ppm)9.03(s,1H),8.81(d,J=7.84Hz,1H),8.77(d,J=7.88Hz,1H),8.70-8.67(m,3H),8.02-7.93(m,3H),7.71-7.67(m,4H),1.69(s,6H),1.42(s,12H).
合成化合物EX2
将4.7g(10mmol)2-(10,10-二甲基-10H-茚并[2,1-b]三亚苯-12-基)-4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷、4.6g(10mmol)9-溴-10-(4-(萘-1-基)苯基)蒽(9-bromo-10-(4-(naphthalen-1-yl)phenyl)anthracene)、0.22g(0.2mmol)四(三苯基膦)钯、20mL 2M碳酸钠、20mL乙醇以及50mL甲苯的混合物经过脱气处理并且放置在氮气下,随后在90℃下加热过夜进行反应。将反应完成后的混合物冷却至室温,接着添加150mL甲醇并且搅拌,再经过抽滤后,形成沉淀物。利用甲苯对沉淀物进行再结晶,以获得4.2g黄色产物,产率为58%。MS(m/z,FAB+):722.4,1HNMR(CDCl3,400MHz):化学位移(ppm)9.13(s,1H),8.89(d,J=7.84Hz,1H),8.83-8.80(m,2H),8.72-8.69(m,2H),8.25(d,J=7.84Hz,1H),7.88-7.66(m,16H),7.58-7.43(m,4H),7.38-7.32(m,5H),1.79(s,6H).
实例2:化合物EX9的合成
合成2-(联苯-2-基)-6-溴-9,9-二甲基-9H-芴(2-(biphenyl-2-yl)-6-bromo-9,9-dimethyl-9H-fluorene)
将35.2g(100mmol)3,6-二溴-9,9-二甲基-9H-芴(3,6-dibromo-9,9-di-methyl-9H-fluorene)、21.8g(110mmol)联苯-2-基硼酸、2.31g(2mmol)四(三苯基膦)钯、75mL2M碳酸钠、150mL乙醇以及300mL甲苯的混合物经过脱气处理并且放置在氮气下,随后在100℃下加热12小时进行反应。将反应完成后的混合物冷却至室温,再利用乙酸乙酯和水分离洗出有机层,将有机层用无水硫酸镁进行干燥以去除溶剂,形成残余物。通过以硅胶填充的管柱层析纯化残余物,得到26.8g(63.0mmol)白色固体产物,产率为63%。
合成13-溴-10,10-二甲基-10H-茚并[2,1-b]三亚苯(13-bromo-10,10-dimethyl-10H-indeno[2,1-b]triphenylene)
在经过脱气及填充氮气的3000mL三颈烧瓶中,将26.8g(60mmol)2-(联苯-2-基)-7-溴-9,9-二甲基-9H-芴溶解于无水二氯甲烷(1500mL)中,随后添加97.5g(600mmol)氯化铁(III)形成混合物,搅拌混合物一小时,在搅拌后的混合物中添加500mL甲醇并且分离出有机层。在真空中将有机层去除溶剂,形成残余物,通过以硅胶填充的管柱层析(己烷-二氯甲烷)来纯化残余物,得到10.7g(25.3mmol)白色固体产物,产率为40%。1HNMR(CDCl3,400MHz):化学位移(ppm)8.95(s,1H),8.79-8.74(m,2H),8.69-8.68(m,3H),7.84(d,J=8.0Hz,1H),7.72-7.65(m,5H),7.57(d,J=8.0Hz,1H),1.66(s,6H).
合成2-(10,10-二甲基-10H-茚并[2,1-b]三亚苯-13-基)-4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷(2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-13-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
将10.7g(25.3mmol)13-溴-10,10-二甲基-10H-茚并[2,1-b]三亚苯13-溴-10,10-二甲基-10H-茚并[2,1-b]三亚苯、7.7g(30.3mmol)双频哪醇硼酸酯、0.3g(0.26mmol)四(三苯基膦)钯、7.4g(75.4mmol)醋酸钾以及500mL1,4-二恶烷的混合物经过脱气处理并且放置在氮气下,随后在90℃下加热16小时进行反应。将反应完成后的混合物冷却至室温,再利用乙酸乙酯和水分离洗出有机相(organic phase),将有机相用无水硫酸镁进行干燥以去除溶剂,形成残余物。通过以硅胶填充的管柱层析来纯化残余物,得到9.5g(20.2mmol)淡黄色固体产物,产率为80%。1HNMR(CDCl3,500MHz):化学位移(ppm)8.93(s,1H),8.77-8.71(m,2H),8.67-8.65(m,3H),7.88(d,J=1.5Hz,1H),7.71-7.64(m,4H),7.29(dd,J1=8.5Hz,J2=1.5Hz,1H),7.42(d,J=8.5Hz,1H),1.62(s,6H),1.42(s,12H).
合成10,10-二甲基-13-(10-(3-(萘-2-基)苯基)蒽-9-基)-10H-茚并[1,2-b]三亚苯(10,10-dimethyl-13-(10-(3-(naphthalen-2-yl)phenyl)anthracen-9-yl)-10H-indeno[1,2-b]trip henylene)
将9.5g(20.2mmol)2-(10,10-二甲基-10H-茚并[2,1-b]三亚苯-13-基)-4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷、9.6g(21mmol)9-溴-10-(3-(萘-2-基)苯基)蒽、0.44g(0.4mmol)四(三苯基膦)钯、30mL2M碳酸钠、40mL乙醇以及100mL甲苯的混合物经过脱气处理并且放置于氮气环境下,再于90℃下加热过夜进行反应。将反应后的混合物冷却至室温,添加300mL甲醇并且搅拌,再经过抽滤后,形成沉淀物。利用甲苯对沉淀物进行再结晶,得到4g黄色产物,产率为53%。MS(m/z,FAB+):722.1,1HNMR(CDCl3,400MHz):化学位移(ppm)8.99(s,1H),8.83-8.82(m,2H),8.68-8.65(m,3H),8.21-8.18(dd,1H),8.14(s,1H),7.99-7.47(m,20H),7.41-7.36(m,4H),1.83(s,6H).
实例3:化合物EX10的合成
合成10,10-二甲基-13-(10-(4-(萘-1-基)苯基)蒽-9-基)-10H-茚并[1,2-b]三亚苯(10,10-dimethyl-13-(10-(4-(naphthalen-1-yl)phenyl)anthracen-9-yl)-10H-indeno[1,2-b]trip henylene)
将9.5g(20.2mmol)2-(10,10-二甲基-10H-茚并[2,1-b]三亚苯-13-基)-4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷、9.6g(21mmol)9-溴-10-(4-(萘-1-基)苯基)蒽、0.44g(0.4mmol)四(三苯基膦)钯、30mL2M碳酸钠、40mL乙醇以及100mL甲苯的混合物经过脱气处理并且放置在氮气下,随后在90℃下加热过夜进行反应。将反应完成后的混合物冷却至室温,添加300mL甲醇并且搅拌,再经过抽滤后,形成沉淀物。利用甲苯对沉淀物进行再结晶,得到9.2g黄色产物,产率为63%。MS(m/z,FAB+):722.4,1HNMR(CDCl3,400MHz):化学位移(ppm)8.99(s,1H),8.83-8.80(m,2H),8.70-8.66(m,3H),8.21-8.13(m,2H),7.99-7.51(m,20H),7.45-7.36(m,4H),1.79(s,6H).
实例4:化合物EX22的合成
合成10,10-二甲基-12-(10-(3-(菲-9-基)苯基)蒽-9-基)-10H-茚并[2,1-b]三亚苯(10,10-dimethyl-12-(10-(3-(phenanthren-9-yl)phenyl)anthracen-9-yl)-10H-indeno[2,1-b]tri phenylene)
将4.7g(10mmol)2-(10,10-二甲基-10H-茚并[2,1-b]三亚苯-12-基)-4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷、5.1g(10mmol)9-溴-10-(3-(菲-9-基)苯基)蒽、0.22g(0.2mmol)四(三苯基膦)钯、20mL2M碳酸钠、20mL乙醇以及50mL甲苯的混合物经过脱气处理并且放置在氮气下,随后在90℃下加热过夜进行反应。将反应完成后的混合物冷却至室温,添加150mL甲醇并且搅拌,再经过抽滤后,形成沉淀物。利用甲苯对沉淀物进行再结晶,得到3.0g黄色产物,产率为69%。MS(m/z,FAB+):772.6,1HNMR(CDCl3,400MHz):化学位移(ppm)9.11(s,1H),8.89(d,J=7.84Hz,1H),8.84-8.78(m,4H),8.71-8.69(m,2H),8.25-8.11(m,3H),7.91-7.64(m,15H),7.58-7.43(m,4H),7.41-7.36(m,4H),1.79(s,6H).
产生有机EL元件的一般方法
依据本发明,提供一种经铟锡氧化物(indium tin oxide,ITO)涂布的玻璃(下文ITO基材),其电阻为9欧姆/平方(ohm/square)至12欧姆/平方且厚度为120nm到160nm,并且在超声波浴中利用多个清洁步骤(例如:清洁剂、去离子水)进行清洁。在进行有机层的气相沉积过程之前,通过UV和臭氧进一步处理经清洁后的ITO基材。用于ITO基材的所有前处理过程均于洁净室(100级)环境中进行。
在诸如电阻加热石英舟(resistively heated quartz boats)等的高真空单元(10-7托(torr))中,通过气相沉积将这些有机层依序涂布于ITO基材上。通过石英晶体监控器(quartz-crystal monitor)精确监控或设定对应层的厚度以及气相沉积速率(0.1nm/sec至0.3nm/sec)。如上所述,个别层还可能由一种以上化合物所组成,意即一般来说掺杂有掺杂剂材料的主体材料。这类型材料可透过从两种或两种以上来源进行共气化(co-vaporization)而达成。
更具体的是,于一较佳实施例中,在本发明所述的有机EL元件中,二吡嗪并[2,3-f:2,3-]喹喔啉-2,3,6,7,10,11-六甲腈(Dipyrazino[2,3-f:2,3-]quinoxaline-2,3,6,7,10,11-hexacarbonitrile,HAT-CN)可用于电洞注入层,N,N-双(萘-1-基)-N,N-双(苯基)-联苯胺(N,N-bis(naphthalene-1-yl)-N,N-bis(phenyl)-benzidine,NPB)最常用于电洞传输层,N-(联苯-4-基)-9,9-二甲基-N-(4'-苯基联苯-4-基)-9H-芴-2-胺(N-(biphenyl-4-yl)-9,9-dimethyl-N-(4'-phenylbiphenyl-4-yl)-9H-fluoren-2-amine)(以下称为EB2)可用于电子阻挡层,10,10-二甲基-12-(10-(萘-2-基)蒽-9-基)-10H-茚并[2,1-b]三亚苯(10,10-dimethyl-12-(10-(naphthalen-2-yl)anthracen-9-yl)-10H-indeno[2,1-b]triphenylene)(以下称为H1)可用于蓝色发光主体,N1,N1,N6,N6-四甲苯基芘-1,6-二胺(N1,N1,N6,N6-tetram-tolylpyrene-1,6-diamine)(以下称为D1)可用于蓝色发光客体;N9,N10-二苯基-N9,N10-二间甲苯基蒽-9,10-二胺(N9,N10-diphenyl-N9,N10-dim-tolylanthracene-9,10-diamine)(以下称为D2)可用于绿色发光客体;2-(10,10-二甲基-10H-茚并[2,1-b]三亚苯-13-基)-9-苯基-1,10-啡啉(2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-13-yl)-9-phenyl-1,10-phenanthroline)(以下称为ET1)可用于电子传输材料并且可与5%锂金属(Li)共沉积,2-(10,10-二甲基-10H-茚并[2,1-b]三亚苯-12-基)-4,6-二苯基-1,3,5-三嗪(2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)-4,6-di-phenyl-1,3,5-triazine)(以下称为ET2)可用于电洞阻挡材料。上述可用于产生标准有机EL元件控制组的现有技术的OLED材料和本发明中的比较性材料,如以下化学结构所示:
典型的有机EL元件由诸如含有Al、Mg、Ca、Li及K的低功函数金属材料所构成,并通过热蒸镀作为阴极,低功函数金属材料可辅助电子从阴极注入至电子传输层。此外,为了减少电子注入的屏障,并且改进有机EL元件性能,在阴极与电子传输层之间引入薄膜电子注入层。电子注入层的常规材料是具有低功函数的金属卤化物或金属氧化物,例如:LiF、LiQ、MgO或Li2O。另一方面,在有机EL元件制造之后,通过使用PR650光谱扫描光谱仪(PR650spectra scan spectrometer)测量EL光谱(EL spectra)和CIE座标(CIEcoordination)。此外,用吉时利2400可程式设计电压-电流源(Keithley2400programmable voltage-current source)获得电流/电压、发光/电压以及良率/电压的特性资料。上述设备是于室温(约25℃)及大气压力环境中操作。
实例5
使用类似于上述一般方法的程序,产生具有以下元件结构I的蓝色荧光有机EL元件,元件结构I:ITO/HAT-CN(10nm)/NPB(800nm)/EB2(5nm)/掺杂D1或D2的主体(30nm)/ET2(15nm)/与5%Li共沉积的ET1(35nm)/Al(160nm)。荧光有机EL元件测试报告的I-V-B(1000尼特(nit)下)和半衰期时间如表1所示。半衰期时间被定义为1000cd/m2的初始亮度降到一半的时间。
表1
请参见表1所示,在以上有机EL元件测试报告的较佳实施例中,显示使用本发明具有式(I)结构的有机化合物应用于有机EL元件的发光主体中,与现有技术的OLED材料相较之下,可使元件达到较为良好的性能,尤其与美国专利案第9,048,437号的先前技术相较之下,在效能及半衰期时间方面均增加约30%。
总而言之,本发明提供一种有机化合物,其可以用于有机EL元件中。本发明亦提供一种有机EL元件,可采用前述有机化合物应用于荧光发光主体材料或其他具有替代性功能的材料。所述及的有机化合物具有由式(I)所示的化学结构:
其中A表示具有二至四个环的经取代或未经取代的稠环碳氢单元,R1至R3独立地表示选自于由氢原子、卤素、具有1至30个碳原子的经取代或未经取代的烷基、具有6至30个碳原子的经取代或未经取代的芳基以及具有6至30个碳原子的经取代或未经取代的芳烷基所组成的群组。
以上所述仅是本发明的较佳实施例而已,并非对本发明有任何形式上的限制,虽然本发明已以较佳实施例提供如上,然而并非用以限定本发明,任何所属技术领域的技术人员,在不脱离本发明技术方案的范围内,当可利用上述公开的技术内容做出些许更动或修饰等同变化的等效实施例,但凡是未脱离本发明技术方案的内容,依据本发明的技术实质对以上实施例所作的任何简单修改、等同变化与修饰,均仍属于本发明技术方案的范围内。
Claims (9)
1.一种化合物,其具有下列式(I)所示的结构:
其中A表示具有二至四个环的经取代或未经取代的稠环碳氢单元,R1至R3独立地表示选自于由氢原子、卤素、具有1至30个碳原子的经取代或未经取代的烷基、具有6至30个碳原子的经取代或未经取代的芳基以及具有6至30个碳原子的经取代或未经取代的芳烷基所组成的群组。
2.根据权利要求1所述的化合物,其进一步具有选自于由下列通式所示结构所组成的群组中的其中一种:
以及
3.一种有机电激发光元件,其包括一对电极、至少一发光层以及一个或多个有机薄膜层,其中所述对电极由阴极和阳极所组成,所述至少一发光层以及所述一个或多个有机薄膜层设置于所述对电极的阴极和阳极之间,且所述至少一发光层包括一种如权利要求1或2所述的化合物。
4.根据权利要求3所述的有机电激发光元件,其中所述至少一发光层中的所述化合物为主体材料。
5.根据权利要求3所述的有机电激发光元件,其中所述至少一发光层中的所述化合物为荧光发射体。
6.根据权利要求3所述的有机电激发光元件,其中所述至少一发光层所发出的光包括蓝色或绿色的荧光。
7.一种有机发光装置,其包括如权利要求1-6任一项所述的有机电激发光元件。
8.一种发光平板,其包括如权利要求1-6任一项所述的有机电激发光元件。
9.一种背光平板,其包括如权利要求1-6任一项所述的有机电激发光元件。
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