JP2020121976A - 金属錯体およびそれを用いた電子輸送材料 - Google Patents
金属錯体およびそれを用いた電子輸送材料 Download PDFInfo
- Publication number
- JP2020121976A JP2020121976A JP2020055580A JP2020055580A JP2020121976A JP 2020121976 A JP2020121976 A JP 2020121976A JP 2020055580 A JP2020055580 A JP 2020055580A JP 2020055580 A JP2020055580 A JP 2020055580A JP 2020121976 A JP2020121976 A JP 2020121976A
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- Prior art keywords
- mmol
- synthesis
- group
- complex
- pyridin
- Prior art date
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- Granted
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- 150000004696 coordination complex Chemical class 0.000 title claims abstract description 158
- 239000000463 material Substances 0.000 title claims abstract description 115
- 238000000034 method Methods 0.000 claims abstract description 68
- 238000004519 manufacturing process Methods 0.000 claims abstract description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 16
- 239000003446 ligand Substances 0.000 claims description 175
- 239000002904 solvent Substances 0.000 claims description 86
- -1 halogen salt Chemical class 0.000 claims description 81
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 71
- 229910052792 caesium Inorganic materials 0.000 claims description 46
- 229910052751 metal Inorganic materials 0.000 claims description 45
- 239000002184 metal Substances 0.000 claims description 45
- 229910052783 alkali metal Inorganic materials 0.000 claims description 41
- 150000001340 alkali metals Chemical class 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 39
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 37
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 37
- 239000011344 liquid material Substances 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000001624 naphthyl group Chemical group 0.000 claims description 24
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 20
- 238000005401 electroluminescence Methods 0.000 claims description 20
- 125000006267 biphenyl group Chemical group 0.000 claims description 19
- 229910052701 rubidium Inorganic materials 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 13
- 125000005561 phenanthryl group Chemical group 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910021645 metal ion Inorganic materials 0.000 claims description 8
- 239000003586 protic polar solvent Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 5
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 5
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 5
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 401
- 125000002837 carbocyclic group Chemical group 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 405
- 238000003786 synthesis reaction Methods 0.000 description 395
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 237
- 239000000203 mixture Substances 0.000 description 189
- 239000010410 layer Substances 0.000 description 170
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 168
- 238000006243 chemical reaction Methods 0.000 description 139
- 239000000243 solution Substances 0.000 description 139
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 134
- 239000002244 precipitate Substances 0.000 description 114
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 90
- 239000007864 aqueous solution Substances 0.000 description 83
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 76
- 239000012044 organic layer Substances 0.000 description 75
- 230000032258 transport Effects 0.000 description 74
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 67
- 235000019341 magnesium sulphate Nutrition 0.000 description 67
- 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 63
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 60
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 58
- 238000001914 filtration Methods 0.000 description 56
- 238000002347 injection Methods 0.000 description 52
- 239000007924 injection Substances 0.000 description 52
- 239000000725 suspension Substances 0.000 description 51
- 239000000706 filtrate Substances 0.000 description 46
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 46
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 43
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 42
- 238000004440 column chromatography Methods 0.000 description 39
- 235000019441 ethanol Nutrition 0.000 description 39
- 230000005525 hole transport Effects 0.000 description 39
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 34
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 33
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 33
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 33
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 33
- 229940031826 phenolate Drugs 0.000 description 33
- 239000007789 gas Substances 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 31
- 229910052739 hydrogen Inorganic materials 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000012298 atmosphere Substances 0.000 description 25
- 239000002198 insoluble material Substances 0.000 description 25
- 239000002994 raw material Substances 0.000 description 25
- 239000000758 substrate Substances 0.000 description 24
- 229910000027 potassium carbonate Inorganic materials 0.000 description 23
- 235000011181 potassium carbonates Nutrition 0.000 description 23
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 229910052744 lithium Inorganic materials 0.000 description 18
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 18
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 18
- 239000000470 constituent Substances 0.000 description 17
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 16
- 229910000029 sodium carbonate Inorganic materials 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 14
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
- 101150003085 Pdcl gene Proteins 0.000 description 13
- 150000004703 alkoxides Chemical class 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 13
- 239000010408 film Substances 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 230000006870 function Effects 0.000 description 11
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 150000002391 heterocyclic compounds Chemical group 0.000 description 10
- GRJRKPMIRMSBNK-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctan-1-ol Chemical compound OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F GRJRKPMIRMSBNK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- 238000007789 sealing Methods 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- GUQPJMIGMSLCQE-UHFFFAOYSA-N 2-[2-phenylmethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine Chemical compound C1=CC=CC=C1COC1=C(C2=NC=CC=C2)C=C(C=C1)B1OC(C)(C)C(C)(C)O1 GUQPJMIGMSLCQE-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910045601 alloy Inorganic materials 0.000 description 8
- 239000000956 alloy Substances 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- 235000011056 potassium acetate Nutrition 0.000 description 8
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 7
- JCMNMOBHVPONLD-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,6-nonafluorohexan-1-ol Chemical compound OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F JCMNMOBHVPONLD-UHFFFAOYSA-N 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- 229910052788 barium Inorganic materials 0.000 description 7
- 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 7
- 238000000576 coating method Methods 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 6
- FHQZCNRCUOMDFY-UHFFFAOYSA-N 8-phenylmethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline Chemical compound O1C(C)(C)C(C)(C)OB1C(C1=CC=CN=C11)=CC=C1OCC1=CC=CC=C1 FHQZCNRCUOMDFY-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
- RXZYKAJOMALBCW-UHFFFAOYSA-N 2-(5-bromo-2-phenylmethoxyphenyl)pyridine Chemical compound C(C1=CC=CC=C1)OC1=C(C=C(C=C1)Br)C1=NC=CC=C1 RXZYKAJOMALBCW-UHFFFAOYSA-N 0.000 description 5
- JHRMQHFRVPVGHL-UHFFFAOYSA-N 2-chloro-1,10-phenanthroline Chemical compound C1=CN=C2C3=NC(Cl)=CC=C3C=CC2=C1 JHRMQHFRVPVGHL-UHFFFAOYSA-N 0.000 description 5
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 5
- ZMIJLGQPKCWYSS-UHFFFAOYSA-N 2-pyridin-2-yl-4,6-bis(4-pyridin-3-ylphenyl)phenol Chemical compound C1=CC(=CN=C1)C1=CC=C(C2=CC(C3=CC=C(C4=CC=CN=C4)C=C3)=CC(C3=CC=CC=N3)=C2O)C=C1 ZMIJLGQPKCWYSS-UHFFFAOYSA-N 0.000 description 5
- RPJJOOCYRZQOOQ-UHFFFAOYSA-N 4,6-diphenyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrimidine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC(C=2N=C(C=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 RPJJOOCYRZQOOQ-UHFFFAOYSA-N 0.000 description 5
- UNQZXBFKKCFONW-UHFFFAOYSA-N 4-bromo-2,6-dipyridin-3-ylpyrimidine Chemical compound C1(C=2N=C(Br)C=C(C3=CC=CN=C3)N=2)=CC=CN=C1 UNQZXBFKKCFONW-UHFFFAOYSA-N 0.000 description 5
- UQVJGZLRAVUKEU-UHFFFAOYSA-N C1=CC2=C(C3=C(C=C2)C=CC(=N3)C4=C5C=CC=NC5=C(C=C4)C(=O)O)N=C1 Chemical compound C1=CC2=C(C3=C(C=C2)C=CC(=N3)C4=C5C=CC=NC5=C(C=C4)C(=O)O)N=C1 UQVJGZLRAVUKEU-UHFFFAOYSA-N 0.000 description 5
- JKNWXLQQQXANCM-UHFFFAOYSA-N OC(C(C(C(C=C1)=CC=C1C1=CC=CN=C1)=C1)=C2N=CC=CC2=C1C(C=C1)=CC=C1C1=CC=CN=C1)=O Chemical compound OC(C(C(C(C=C1)=CC=C1C1=CC=CN=C1)=C1)=C2N=CC=CC2=C1C(C=C1)=CC=C1C1=CC=CN=C1)=O JKNWXLQQQXANCM-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 229920001940 conductive polymer Polymers 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 238000007747 plating Methods 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 229960003975 potassium Drugs 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- MCAIDINWZOCYQK-UHFFFAOYSA-N (2-phenylmethoxyphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1OCC1=CC=CC=C1 MCAIDINWZOCYQK-UHFFFAOYSA-N 0.000 description 4
- FYTQDADUVFGKHG-UHFFFAOYSA-N 1,3-dibromo-2-phenylmethoxybenzene Chemical compound BrC1=CC=CC(Br)=C1OCC1=CC=CC=C1 FYTQDADUVFGKHG-UHFFFAOYSA-N 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- JKBRIIBMUJCJQJ-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)-4,6-bis(4-pyridin-3-ylphenyl)phenol Chemical compound C1=CN=CC(=C1)C1=CC=C(C2=C(C(=CC(C3=CC=C(C4=CN=CC=C4)C=C3)=C2)C2=NC3=C(O2)C=CC=C3)O)C=C1 JKBRIIBMUJCJQJ-UHFFFAOYSA-N 0.000 description 4
- CROBJCWPAIHRTI-UHFFFAOYSA-N 2-(2-phenylmethoxyphenyl)-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine Chemical compound CC1(OB(OC1(C)C)C1=CC(C2=NC(=CC=C2)C2=C(OCC3=CC=CC=C3)C=CC=C2)=CC=C1)C CROBJCWPAIHRTI-UHFFFAOYSA-N 0.000 description 4
- HQHMGXAITXSPME-UHFFFAOYSA-N 2-(3-bromophenyl)-1,10-phenanthroline Chemical compound BrC1=CC=CC(C=2N=C3C4=NC=CC=C4C=CC3=CC=2)=C1 HQHMGXAITXSPME-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- WXRCBHMZGFEIJN-UHFFFAOYSA-N 2-[2-phenylmethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzothiazole Chemical compound O1C(C)(C)C(C)(C)OB1C(C=C1C=2SC3=CC=CC=C3N=2)=CC=C1OCC1=CC=CC=C1 WXRCBHMZGFEIJN-UHFFFAOYSA-N 0.000 description 4
- QVUCIYZFZLPUOZ-UHFFFAOYSA-N 2-[5-(1,10-phenanthrolin-2-yl)-8-phenylmethoxyquinolin-7-yl]-1,10-phenanthroline Chemical compound C1=CC=CC=C1COC1=C(C2=NC3=C4C(=CC=C3C=C2)C=CC=N4)C=C(C2=CC=C3C=CC4=CC=CN=C4C3=N2)C2=CC=CN=C12 QVUCIYZFZLPUOZ-UHFFFAOYSA-N 0.000 description 4
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- 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
- 125000005842 heteroatom Chemical group 0.000 description 1
- KEDRKJFXBSLXSI-UHFFFAOYSA-M hydron;rubidium(1+);carbonate Chemical compound [Rb+].OC([O-])=O KEDRKJFXBSLXSI-UHFFFAOYSA-M 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- HJZPJSFRSAHQNT-UHFFFAOYSA-N indium(3+) oxygen(2-) zirconium(4+) Chemical compound [O-2].[Zr+4].[In+3] HJZPJSFRSAHQNT-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 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 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 238000001182 laser chemical vapour deposition Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229910000032 lithium hydrogen carbonate Inorganic materials 0.000 description 1
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 description 1
- XKPJKVVZOOEMPK-UHFFFAOYSA-M lithium;formate Chemical compound [Li+].[O-]C=O XKPJKVVZOOEMPK-UHFFFAOYSA-M 0.000 description 1
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- XBECFEJUQZXMFE-UHFFFAOYSA-N n-(4-aminobutyl)acetamide;hydrochloride Chemical compound Cl.CC(=O)NCCCCN XBECFEJUQZXMFE-UHFFFAOYSA-N 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- FZJCXIDLUFPGPP-UHFFFAOYSA-N propan-2-ol;toluene Chemical compound CC(C)O.CC1=CC=CC=C1 FZJCXIDLUFPGPP-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- RCYFOPUXRMOLQM-UHFFFAOYSA-N pyrene-1-carbaldehyde Chemical compound C1=C2C(C=O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 RCYFOPUXRMOLQM-UHFFFAOYSA-N 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 description 1
- WPFGFHJALYCVMO-UHFFFAOYSA-L rubidium carbonate Chemical compound [Rb+].[Rb+].[O-]C([O-])=O WPFGFHJALYCVMO-UHFFFAOYSA-L 0.000 description 1
- 229910000026 rubidium carbonate Inorganic materials 0.000 description 1
- 229940102127 rubidium chloride Drugs 0.000 description 1
- FOGKDYADEBOSPL-UHFFFAOYSA-M rubidium(1+);acetate Chemical compound [Rb+].CC([O-])=O FOGKDYADEBOSPL-UHFFFAOYSA-M 0.000 description 1
- ZIMBPNXOLRMVGV-UHFFFAOYSA-M rubidium(1+);formate Chemical compound [Rb+].[O-]C=O ZIMBPNXOLRMVGV-UHFFFAOYSA-M 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- YJPVTCSBVRMESK-UHFFFAOYSA-L strontium bromide Chemical compound [Br-].[Br-].[Sr+2] YJPVTCSBVRMESK-UHFFFAOYSA-L 0.000 description 1
- 229910001625 strontium bromide Inorganic materials 0.000 description 1
- 229940074155 strontium bromide Drugs 0.000 description 1
- 229910001631 strontium chloride Inorganic materials 0.000 description 1
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- KRIJWFBRWPCESA-UHFFFAOYSA-L strontium iodide Chemical compound [Sr+2].[I-].[I-] KRIJWFBRWPCESA-UHFFFAOYSA-L 0.000 description 1
- 229910001643 strontium iodide Inorganic materials 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000005922 tert-pentoxy group Chemical group 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 238000007751 thermal spraying Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- BZHGXQBPJUHVFW-UHFFFAOYSA-N toluene;tritert-butylphosphane Chemical compound CC1=CC=CC=C1.CC(C)(C)P(C(C)(C)C)C(C)(C)C BZHGXQBPJUHVFW-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- ITHPEWAHFNDNIO-UHFFFAOYSA-N triphosphane Chemical compound PPP ITHPEWAHFNDNIO-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
-
- 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
-
- 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
- C07D401/02—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 two hetero rings
- C07D401/10—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 two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- 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
- 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
- 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
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- 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
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
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- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
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- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/04—Sodium compounds
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- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/06—Potassium compounds
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Abstract
Description
例えば、特許文献1では、電子輸送性の有機化合物と、仕事関数(電気陰性度)の低い金属であるアルカリ金属を含む金属化合物とを共蒸着することにより電子注入層中に金属化合物を混入させ、電子注入層の特性の改善を図る構成が提案されている。
また、特許文献2では、ホスフィンオキサイド化合物を電子輸送材料として用いることが提案されている。更に、特許文献3では、電子輸送層の構成として、配位部位を有する有機化合物にアルカリ金属をドーピングする方法が提案されている。
しかしながら、ホスフィンオキシド誘導体は有機EL素子に用いた際に良好な電子輸送性を示すものの、非特許文献2に記載のようにアニオン状態のP−C結合解離エネルギーが低く耐久性に課題を残していた。
本発明の新規な配位子を有する金属錯体は、ホスフィンオキシド誘導体のように電子輸送性とアルコール可溶性の両方を有するが、ホスフィンオキシド誘導体のようにアニオン状態で不安定なP−C結合を有しておらず、耐久性と高い電子輸送性を両立でき、有機電界発光素子用の電子輸送材料として好適に使用できる。
<1> 少なくとも4個以上の炭素環および/または複素環を含む下記一般式(1)から(7)で表されることを特徴とする金属錯体。
式(1)から(7)において、R1、R3、R5およびR7はそれぞれ独立に2価のフェニル基、ナフチル基、ピリジル基またはピリミジン基から選ばれる接続基であり、R2、R4、R6およびR8はそれぞれ独立に水素原子または複素環式化合物残基を表す。また、Mはアルカリ金属またはアルカリ土類金属を表し、n1からn4はそれぞれ独立に0〜2の整数であり、lは1または2の整数である。
<3> 前記R2、R4、R6およびR8が、次の一般式(8a)から(8c)で表される含窒素環式化合物残基である前記<2>に記載の金属錯体。
式(8a)から(8c)において、R10は炭素数1〜4のアルキル基、フェニル基、ビフェニル基、ナフチル基、ピリジル基、ビピリジル基またはフェナントロリル基を表し、m1は0〜4の整数である。
<4> 前記R2、R4、R6およびR8が、次の一般式(9a)から(9d)で表される含窒素環式化合物残基である前記<2>に記載の金属錯体。
式(9a)から(9d)において、R10は炭素数1〜4のアルキル基、フェニル基、ビフェニル基、ナフチル基、ピリジル基、ビピリジル基またはフェナントロリル基を表し、m1は0〜3の整数である。
<5> 前記R2、R4、R6およびR8が、次の一般式(10a)から(10d)で表される含窒素環式化合物残基である前記<2>に記載の金属錯体。
式(10a)から(10d)において、R10からR12は、それぞれ独立に炭素数1〜4のアルキル基、フェニル基、ビフェニル基、ナフチル基、ピリジル基、ビピリジル基またはフェナントロリル基を表し、m1からm3はそれぞれ独立に0〜3の整数である。
<6> 前記R2、R4、R6およびR8が、次の一般式(11a)から(11d)で表される含窒素環式化合物残基である前記<2>に記載の金属錯体。
式(11a)から(11d)において、R10、R11はそれぞれ独立に炭素数1〜4のアルキル基、フェニル基、ビフェニル基、ナフチル基、ピリジル基、ビピリジル基またはフェナントロリル基を表し、m1は0〜3の整数であり、m2は0〜4の整数である。
<8> 前記アルカリ金属が、RbまたはCsである前記<7>に記載の金属錯体。
<9> 前記<1>から<8>のいずれか1項に記載の金属錯体に用いる配位性化合物。
<10> 前記<1>から<8>のいずれかに記載のアルカリ金属錯体からなることを特徴とする有機電界発光素子用の電子輸送材料。
<11> 前記電子輸送材料が、さらに金属アルコシドを含有する前記<10>に記載の電子輸送材料。
<12> 前記金属アルコシドが、下記一般式(A)または(B)で表される前記<11>に記載の電子輸送材料。
R20- M (A)
R20- M - R21 (B)
式(A)又は(B)において、R20、R21はそれぞれ独立に任意のアルキルアルコキシ基を表し、また、Mはアルカリ金属またはアルカリ土類金属を表す。
<13> 前記電子輸送材料が、さらにアルカリ金属イオンおよびアルカリ土類金属イオンのうちの少なくとも1種の金属イオンのハロゲン塩、炭酸塩、炭酸水素塩、水酸化物、または、炭素数1から9の有機酸塩を含有する前記<10>から<12>のいずれかに記載の電子輸送材料。
<14> 前記<10>から<13>のいずれかに記載の電子輸送材料をプロトン性極性溶媒に溶解してなる有機電界発光素子の電子輸送層を構築するための液状材料。
<15> 前記プロトン性極性溶媒が炭素数1〜10のアルコール系溶媒である前記<14>に記載の液状材料。
<16> 前記炭素数1〜10のアルコール系溶媒が、1価または2価のアルコールである前記<15>に記載の液状材料。
<17> 前記液状材料が、前記<1>から<8>のいずれかに記載のアルカリ金属錯体を0.01から10重量%含有する前記<14>に記載の液状材料。
<18> 前記<10>から<13>のいずれかに記載の電子輸送材料を使用してなることを特徴とする有機電界発光素子。
<19> 前記<14>から<17>のいずれかに記載の液状材料を使用し、有機電界発光素子の電子輸送層を湿式で構築することを特徴とする有機電界発光素子の製造方法。
本発明の金属錯体からなる電子輸送材料は、高い電子輸送性と高い耐久性を両立でき、有機電界発光素子用の電子輸送材料として好適に使用できる。
本発明を適用することにより、高い生産性かつ低コストで製造でき、発光効率に優れ、高い耐久性を有する有機電界発光素子が提供される。
2 基板
3 陽極
4 正孔注入層
5 正孔輸送層
6 発光層
7 電子輸送層
8 陰極
9 封止部材
本発明の第1の実施の形態に係る金属錯体は、少なくとも4個以上の炭素環および/または複素環を含む下記一般式(1)から(7)で表される金属錯体である。
後述する電子輸送材料用の金属錯体としては、アルカリ金属がより好ましく、その中でも電子注入性およびアルコール溶解性の両方の観点から、Li<Na<K<Rb<Csの順で、RbまたはCsが好適に使用される。また、アルカリ土類金属としては、Baが好適に使用される。
即ち、含窒素環式化合物残基のR2等が、ピリジン骨格からなるものであり、置換基R10を有していてもよい。R10としては、メチル基、エチル基、n-プロピル基、iso-プロピル基、n-ブチル基、tert-ブチル基等の炭素数1〜4の直鎖または分岐アルキル基、フェニル基、ビフェニル基、ナフチル基、ピリジル基、ビピリジル基またはフェナントロリル基が挙げられる。また、置換基R10の数を示すm1は、0〜4の整数である。
即ち、含窒素環式化合物残基のR2等が、ピリミジン骨格またはトリアジン骨格からなるものであり、置換基R10を有していてもよい。R10としては、メチル基、エチル基、n-プロピル基、iso-プロピル基、n-ブチル基、tert-ブチル基等の炭素数1〜4の直鎖または分岐アルキル基、フェニル基、ビフェニル基、ナフチル基、ピリジル基、ビピリジル基またはフェナントロリル基が挙げられる。これらの中でも、フェニル基、ビフェニル基、ナフチル基、ピリジル基、ビピリジル基またはフェナントロリル基が好ましい。また、置換基R10の数を示すm1は、0〜3の整数である。
即ち、含窒素環式化合物残基のR2等が、フェナントロリン骨格からなるものであり、置換基を有していてもよい。R10等としては、メチル基、エチル基、n-プロピル基、iso-プロピル基、n-ブチル基、tert-ブチル基等の炭素数1〜4の直鎖または分岐アルキル基、フェニル基、ビフェニル基、ナフチル基、ピリジル基、ビピリジル基またはフェナントロリル基が挙げられる。これらの中でも、フェニル基、ビフェニル基、ナフチル基、ピリジル基、ビピリジル基またはフェナントロリル基が好ましい。また、置換基R10等の数を示すm1からm3はそれぞれ独立に0〜3の整数である。
即ち、含窒素環式化合物残基のR2が、カルボリン骨格からなるものであり、置換基R10等を有していてもよい。R10等としては、メチル基、エチル基、n-プロピル基、iso-プロピル基、n-ブチル基、tert-ブチル基等の炭素数1〜4の直鎖または分岐アルキル基、フェニル基、ビフェニル基、ナフチル基、ピリジル基、ビピリジル基またはフェナントロリル基が挙げられる。これらの中でも、フェニル基、ビフェニル基、ナフチル基、ピリジル基、ビピリジル基またはフェナントロリル基が好ましい。また、置換基R10等の数を示すm1は0〜3の整数であり、m2は0〜4の整数である。
本発明の一般式(1)で表される金属錯体としては、次の化合物が例示される。なお、Mは、アルカリ金属またはアルカリ土類金属を表わす。但し、Mがアルカリ土類金属の場合は、各配位子がMに2個配位した構造となる。
本発明の一般式(2)で表される金属錯体としては、次の化合物が例示される。なお、Mは、アルカリ金属またはアルカリ土類金属を表わす。但し、Mがアルカリ土類金属の場合は、各配位子がMに2個配位した構造となる。
本発明の一般式(3)で表される金属錯体としては、次の化合物が例示される。なお、Mは、アルカリ金属またはアルカリ土類金属を表わす。但し、Mがアルカリ土類金属の場合は、各配位子がMに2個配位した構造となる。
本発明の一般式(4)で表される金属錯体としては、次の化合物が例示される。なお、Mは、アルカリ金属またはアルカリ土類金属を表わす。但し、Mがアルカリ土類金属の場合は、各配位子がMに2個配位した構造となる。
本発明の一般式(5)で表される金属錯体としては、次の化合物が例示される。なお、Mは、アルカリ金属またはアルカリ土類金属を表わす。但し、Mがアルカリ土類金属の場合は、各配位子がMに2個配位した構造となる。
本発明の一般式(6)で表される金属錯体としては、次の化合物が挙げられる。なお、Mは、アルカリ金属またはアルカリ土類金属を表わす。但し、Mがアルカリ土類金属の場合は、各配位子がMに2個配位した構造となる。
本発明の一般式(7)で表される金属錯体としては、次の化合物が挙げられる。なお、Mは、アルカリ金属またはアルカリ土類金属を表わす。但し、Mがアルカリ土類金属の場合は、各配位子がMに2個配位した構造となる。
1)一般式(1)の構造を有する配位子は、次のようにして合成することができる。
なお、式中、Xは、フッ素原子、塩素原子、臭素原子、ヨウ素原子、トリフラート基、トシラート基、メシラート基、ジアゾニオ基等の脱離基を表す。
1)一般式(2)の構造を有する配位子は、次のようにして合成することができる。
なお、式中、Xは、フッ素原子、塩素原子、臭素原子、ヨウ素原子、トリフラート基、トシラート基、メシラート基、ジアゾニオ基等の脱離基を表す。
1)一般式(3)の構造を有する配位子は、次のようにして合成することができる。
なお、式中、Xは、フッ素原子、塩素原子、臭素原子、ヨウ素原子、トリフラート基、トシラート基、メシラート基、ジアゾニオ基等の脱離基を表す。
1)一般式(4)の構造を有する配位子は次のようにして合成することができる。
なお、式中、Xは、フッ素原子、塩素原子、臭素原子、ヨウ素原子、トリフラート基、トシラート基、メシラート基、ジアゾニオ基等の脱離基を表す。
1)一般式(5)の構造を有する配位子は、次のようにして合成することができる。
1)一般式(6)の構造を有する配位子は、次のようにして合成することができる。
1)一般式(7)の構造を有する配位子は、次のようにして合成することができる。
本発明の第2の実施の形態に係る配位性化合物は、前記金属錯体を構成する配位子である。即ち、本発明の第1の実施の形態に係る、少なくとも4個以上の炭素環および/または複素環を含む一般式(1)から(7)で表される金属錯体を構成する化合物である。
本発明の第3の実施の形態に係る電子輸送材料は、上記第1の実施の形態で詳述した一般式(1)から(7)で表される金属錯体、特に、アルカリ金属錯体またはアルカリ土類金属錯体からなるものである。
本発明の金属錯体は、いずれも基本骨格に「−O−M…N≡」のキレート結合をもつ環を有しており、また2価のフェニル基、ナフチル基、ピリジル基またはピリミジン基から選ばれる接続基R1等、および、水素原子または複素環式化合物残基R2等を構成要素とするものである。
電子輸送材料用の金属錯体としては、アルカリ金属がより好ましく、その中でも電子注入性およびアルコール溶解性の両方の観点から、Li<Na<K<Rb<Csの順で、Rb又はCsが好適に使用される。また、アルカリ土類金属としては、Baが好適に使用される。
金属アルコキシドは、調整したものを用いることも可能であるが、任意のアルコールにアルカリ金属またはアルカリ土類金属を添加し、溶媒と反応させることにより金属アルコキシドを調整することも可能である。
R20− M (A)
R20− M − R21 (B)
式(A)又は(B)において、R20、R21はそれぞれ独立に任意のアルキルアルコキシ基を表し、また、Mはアルカリ金属またはアルカリ土類金属を表す。
下記反応式(C)又は(D)において、Rは対応する溶媒の置換基に対応し、また、Mはアルカリ金属またはアルカリ土類金属を表す。なお、反応に使用する溶媒としては、後述する液状材料で使用される溶媒が同様に使用できる。その中でも、1価のアルコールが好ましい。
これらは、アルカリ金属錯体またはアルカリ土類金属錯体に対し0.1重量%から50重量%、より好ましくは1重量%から40重量%の範囲で適宜使用される。
これらの無機または有機酸塩を含むことにより、電子輸送性を向上させ、耐久性を向上させることができる。
これらは、アルカリ金属錯体またはアルカリ土類金属錯体に対し0.1から50重量%、よりこのましくは1重量%から40重量%の範囲で適宜使用される。
本発明の第4の実施の形態に係る発明は、上記一般式(1)から(7)で表される構造を有する金属錯体からなる電子輸送材料を溶媒に溶解した液状材料に係るものである。
本発明の液状材料では、溶媒は有機発光層を膨潤または溶解し難いものであることが好ましい。これにより、有機電界発光素子に用いる場合に、有機発光層薄膜の変質・劣化や膜厚が極端に薄くなることを防止することができ、その結果、より一層高い効率および耐久性に優れ、またより一層生産性に優れる有機電界発光素子製造用の液状材料が得られる。
このような炭素数のアルコールは、金属化合物の溶解性が高く、その結果、より一層高い効率および耐久性に優れ、またより一層生産性に優れる有機電界発光素子製造用の液状材料が得られる。
次に、本願発明の電子輸送材料(第3の実施形態)を使用してなる、第5の実施の形態である有機電界発光素子について説明する。
図1に示すように、本発明の有機電界発光素子1は、陽極3と陰極8との間に挟まれるように積層された複数の有機化合物層(陽極3側から順に、正孔注入層4、正孔輸送層5、発光層6、電子輸送層7)を有する有機電界発光素子である。陽極3は透明な基板2上に設けられており、全体が封止部材9で封止されている。正孔輸送層5、発光層6はアルコール系溶媒に不溶な有機化合物からなっている。発光層6が陰極8と対向している側の面で発光層6に接するように湿式法で形成された電子輸送層7は、アルコール系溶媒に可溶な1又は複数の上記電子輸送材料を含んでいる。
例えば、正孔注入層4には、正孔伝導準位(Ev)と陽極3に用いられる材料の仕事関数との差が小さく、放射光の再吸収を防ぐために可視光領域に吸収帯のない材料が好ましく用いられる。また、正孔輸送層5には、発光層6の構成材料との間で励起錯体(エキサイプレックス)や電荷移動錯体を形成せず、発光層6において生成した励起子のエネルギーの移動や発光層6からの電子注入を防ぐために、発光層6の励起子エネルギーよりも一重項励起エネルギーが大きく、バンドギャップエネルギーが大きく、電子伝導電位(Ec)が浅い材料が好ましく用いられる。陽極3にITOが用いられる場合、正孔注入層4及び正孔輸送層5に好適に用いられる材料の例としては、それぞれ、ポリ(3,4−エチレンジオキシチオフェン/スチレンスルホン酸)(PEDOT/PSS)及びポリ(N−ビニルカルバゾール)(PVK)が挙げられる。
まず、基板2を用意し、この基板2上に陽極3を形成する。陽極3は、例えば、プラズマCVD、熱CVD、レーザーCVDのような化学蒸着法(CVD)、真空蒸着、スパッタリング、イオンプレーティング等の乾式メッキ法、電界メッキ、浸漬メッキ、無電界メッキ等の湿式メッキ法、溶射法、ゾル・ゲル法、MOD法、金属箔の接合等を用いて形成することができる。
正孔注入層4及び正孔輸送層5は、例えば、正孔注入材料を溶媒に溶解又は分散媒に分散してなる正孔注入層形成用材料を陽極3上に供給した後、乾燥(脱溶媒又は脱分散媒)し、次いで正孔輸送材料を溶媒に溶解又は分散媒に分散してなる正孔輸送層形成用材料を正孔注入層4上に供給した後、乾燥することにより形成することができる。正孔注入層形成用材料及び正孔輸送層形成用材料の供給方法としては、例えば、スピンコート法、キャスティング法、マイクログラビアコート法、グラビアコート法、バーコート法、ロールコート法、ワイヤーバーコート法、ディップコート法、スプレーコート法、スクリーン印刷法、フレキソ印刷法、オフセット印刷法、インクジェット印刷法等の各種塗布法を用いることができる。このような塗布法を用いることにより、正孔注入層4及び正孔輸送層5を比較的容易に形成することができる。
なお、乾燥は、例えば、大気圧又は減圧雰囲気中での放置、加熱処理、不活性ガスの吹付け等により行うことができる。
ここで、酸素プラズマ処理の条件としては、例えば、プラズマパワー100〜800W程度、酸素ガス流量50〜100mL/min程度、被処理部材(陽極3)の搬送速度0.5〜10mm/sec程度、基板2の温度70〜90℃程度とするのが好ましい。
発光層6は、例えば、発光材料を溶媒に溶解又は分散媒に分散してなる発光層形成用材料を正孔輸送層5上に供給した後、乾燥(脱溶媒又は脱分散媒)することにより形成することができる。発光層形成用材料の供給方法及び乾燥の方法は、正孔注入層4の形成で説明したのと同様である。
(a)第1の工程
まず、前述した一般式(1)から(7)で表される金属錯体、および必要に応じ金属アルコシド等のドーパントを含む液状材料を調製する。
液状材料の調製に用いる溶媒としては、発光層6が有機発光層の場合、膨潤または溶解し難いものが好ましい。これにより、発光材料の変質・劣化や、有機発光層6が溶解し、膜厚が極端に減少することを防止することができる。その結果、有機電界発光素子1の発光効率の低下を防止することができる。溶媒には、前述したアルコール系溶媒、好ましくは炭素数1〜10のアルコールを用いるのが好適である。これにより、発光効率の低下を防止することができ、有機電界発光素子1を生産性よく製造することができる。
次に、調製した液状材料を発光層6上に供給した後、乾燥(脱溶媒)する。これにより、一般式(1)から(7)で表される金属錯体を含有する電子輸送層7が得られる。液状材料の供給方法および乾燥の方法は、前記正孔注入層4及び正孔輸送層5の形成で説明したのと同様である。
陰極8は、例えば、真空蒸着法、スパッタリング法、金属箔の接合、金属微粒子インクの塗布および焼成等を用いて形成することができる。
最後に、得られた有機電界発光素子1を覆うように封止部材9を被せ、基板2に接合する。以上のような工程を経て、有機電界発光素子1が得られる。
なお、ディスプレイ装置の駆動方式としては、特に限定されず、アクティブマトリックス方式、パッシブマトリックス方式のいずれであってもよい。
化合物の確認は、薄層クロマトグラフィーとAPCI MSにより行った。また錯体は、NMR[(60MHz)は日本電子製JNM−MY60FT、高分解能NMR(500MHz)は日本電子社製JNM−ECX−500を用いて測定した。APCI MSは、Waters社製LCTPremire XEを用いて測定した。
また、カラムクロマトグラフィーに用いたシリカゲルC300、NH、PEIは、それぞれ和光純薬社製ワコーシルC300、富士シリシア化学社製Chromatorex NH2、Chromatorex PEIを用いた。
[A]一般式(1)で表される金属錯体
1)2−(2−アセトキシ−5−ブロモフェニル)ピリジンの合成
2−(2−アセトキシ−5−ブロモフェニル)ピリジン(CAS No. 862742−97−0, M008)は、Kalyaniらの方法(Org. Lett. ,7(19), 4149 − 4152, 2015)を用いて合成した。
ルビジウム2−(ピリジン−2−イル)−4−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)フェノラート錯体(L104−Rb)の合成
2,4,6−トリブロモフェニルベンジルエーテル(M006) 4.21g(10mmol)をジエチルエーテル 50mLに加え−60℃に冷却した。そこへ2.5Mn−ブチルリチウム−ヘキサン溶液 4.8mL(12mmol)を加え、60分間撹拌した。続いて−60℃でトリイソプロポキシボラン 3.46mL(ca.2.82g、15mmol)を加え、−60℃で30分間、室温で15時間撹拌した。反応終了後、1N塩酸50mLを加え、室温で1時間撹拌した。NaHCO3で中和後、ジクロロメタンで抽出した。有機層は硫酸マグネシウムで乾燥後、減圧下で濃縮し、2−ベンジロキシ−3,5−ジブロモフェニルボロン酸(M025)を得た。得られた化合物はさらに精製せず次のブロモピリジンとのカップリング反応に用いた。
前の反応で得られた残渣(10 mmolと判断)、2−ブロモピリジン 1.43mL(ca.2.37g、15mmol)、テトラキス(トリフェにルホスフィン)パラジウム 347mg(0.3mmol)、2M炭酸ナトリム水溶液 10mL(20 mmol)をジオキサン 60mLに加え、80℃で22時間撹拌した。反応終了後、水を加え、ジクロロメタンで抽出した。有機層は硫酸マグネシウムで乾燥後、減圧下で濃縮した。得られた残渣はカラムクロマトグラフィー(NH、ジクロロメタン:MeOH)で精製し2−(2−ベンジロキシ−3,5−ジブロモフェニル)ピリジン(M026) 1.67g(トリブロモフェニルベンジルエーテルより40%)を得た。
2−(ジベンジチオフェン−4−イル)−2−(2−ヒドロキシ−3−ジベンゾチオフェン−4−イル)フェニルピリジン(L110)の合成
1H NMR(CDCl3)δ 6.96−8.22 (m, 20H, ArH)、14.15(s, 1H, OH)
2−(3−(6−(2−ヒドロキシフェニル)ピリジン−3−イル)フェニル)−4,6−ジフェニルピリミジン (L113)の合成
1H NMR (CDCl3) δ 6.83−8.87 (m, 21H, ArH)、14.71(s, 1H, OH)
1H NMR(CDCl3) δ 6.93−9.37 (21H, ArH)、14.71(s, 1H, OH)
[B]一般式(2)で表される金属錯体
1)5−ブロモ−8−ベンジロキシキノリン (CAS No. 202259−06−1, M017)はOmarらの方法(J. Chem. Sci., 127(11), 1937−1943, 2015)を用いて合成した。
(4−1−2)配位子の合成:2−(2−ヒドロキシ−5−(4−(4,6−ジフェニルピリミジン−2−イル)フェニル)フェニル)ベンゾオキサゾール(L401)の合成
上記で得られた金属錯体を、プロトン性極性溶媒に溶解させて有機電界発光素子の電子輸送層を構築するための液状材料を製造した。
例えば、金属錯体L101−Rb[ルビジウム2−(ピリジン−2−イル)−4−(4−(4,6−ジフェニルピリミジン−2−イル)フェニル)フェノラート錯体](後述の実施例1の錯体)を1−ヘプタノールに溶解し、5g/L〜15g/Lのアルコール溶液を調整した。
上記で得られたその他の金属錯体についても、同様にアルコール溶液を調整した。使用した溶媒は表1に記載する。これらはいずれも成膜性に優れていた。
(1)有機電界発光素子の製造
ITO基板はテクノプリント製(膜厚150nm)を使用した。基板洗浄に用いる2−プロパノールは和光純薬製の電子工業用を用い、電子輸送層の成膜に用いるアルコール類、および正孔輸送層、発光層に用いるトルエンは和光純薬製のものを用いた。正孔注入層としてはPEDOT:PSS(Heraeus製のAI4083)を原液のまま用いた。正孔輸送層としてはトリフェニルアミンポリマーにジクミルパーオキサイドを1phr添加したトルエン溶液(5g/L)を用いた。発光層にはF8BTのトルエン溶液(10g/L)を用いた。電子輸送層には下記表1中の化合物を用い、濃度が7.5g/Lの1−ヘプタノール溶液を調整した。
正孔注入層および正孔輸送層、発光層、電子輸送層はIDEN製のスピンコーターを用いて形成後、N2雰囲気下で乾燥した。
陽極:ITO(150nm)
正孔注入層:PEDOT:PSS (35nm)
正孔輸送層:トリフェニルアミンポリマー(20nm)
発光層:F8BT(アルドリッチ製 CAS:210347−52−7)(60nm)
電子輸送層:20nm
陰極:LiF(0.5nm)/Al(100nm)またはAl(100nm)
また、作製した有機EL素子の寿命は寿命評価測定装置(九州計測器製)を用いて測定した。素子を25℃一定の恒温槽内に設置し、定電流駆動に伴う輝度電圧の変化を測定した。ただし、素子評価の加速係数には1.758を使用した。100cd/m2に換算した駆動時間により、初期輝度の1/2に達した半減時間により比較した。
T=(L0/L)1.758×T1
(式中L0:初期輝度[cd/m2]、L:換算輝度[cd/m2]、T1:実測の輝度半減時間、T:換算した輝度半減時間)
1)トリフェニルアミンポリマー(CAS:472960−35−3)
1)実施例1
上記(1)の有機電界発光素子の製造において、下記表1の実施例1の電子輸送層材料としてL101−Rbを、ドーパントとしてLiOBuを使用した。また、電子注入層有・無の場合を併せて実施した。得られた素子の駆動電圧(V)、電流効率(ηc)および相対寿命の各物性値を併せて表1に示した。
実施例1において、電子輸送層材料を表1、2に示す化合物に代えた以外は実施例1と同様に素子を製造した。なお、実施例2においては、ドーパントとしてCsOnHepを使用した。得られた素子の駆動電圧(V)、電流効率(ηc)および相対寿命の各物性値を併せて表1、2に示した。
まず、比較例1の類似化合物LiBPP(3個の炭素環および/または複素環を有する)よりも本実施例化合物を使用した素子(実施例1から23)の方が、低駆動電圧、長寿命化していることが分かる。この理由は、定かではないが比較例化合物に対し4個以上の炭素環および/または複素環を有することにより成膜性および電子輸送性が向上していることに起因すると考えられる。
また、実施例11、12と比較例2、3との比較では、本実施例化合物を使用した素子の大幅な長寿命化が達成されていることが分かる。この理由は、定かではないが比較例のホスフィンオキシド化合物のP−C結合の結合解離エネルギーが低く、低寿命化につながっていると考えられる。一方、本実施例化合物では、P−C結合を有している化合物はなく長寿命化が実現できている。
また、実施例1、2と実施例3、あるいは実施例11と実施例12との比較により、金属アルコキシドの添加により更なる低駆動電圧、長寿命化が達成されることがわかる。
因みに、比較例3は、比較例2に対し金属アルコキシドを添加したものである。これによりホスフィンオキシド化合物でも長寿命化、低駆動電圧化が実現されているが、本実施例化合物においては、金属アルコキシド、特にLiOBuの添加により、大幅に長寿命、低駆動電圧化を示しており、本実施例化合物の有用性を示している。
Claims (14)
- 少なくとも1つの配位子中に5個以上の炭素環および/または複素環を含む下記一般式(2)、(4)、(5)および(7)で表されることを特徴とする金属錯体。
式(2)、(4)、(5)および(7)において、R1、R3およびR5はそれぞれ独立に2価のフェニル基、ナフチル基、ピリジル基またはピリミジン基から選ばれる接続基であり、R2、R4およびR6はそれぞれ独立に水素原子または下記(I)〜(IV)から選ばれた含窒素環式化合物残基を表し、R2、R4およびR6の少なくともいずれか一つは下記(I)〜(IV)から選ばれた含窒素環式化合物残基である。また、Mはアルカリ金属またはアルカリ土類金属を表し、n1からn3はそれぞれ独立に0〜2の整数であり、lは1または2の整数である。
(I)次の一般式(8a)から(8c)で表される含窒素環式化合物残基
式(8a)から(8c)において、R10は炭素数1〜4のアルキル基、フェニル基、ビフェニル基、ナフチル基、ピリジル基、ビピリジル基またはフェナントロリル基を表し、m1は0〜4の整数である。
(II)次の一般式(9a)から(9d)で表される含窒素環式化合物残基
式(9a)から(9d)において、R10は炭素数1〜4のアルキル基、フェニル基、ビフェニル基、ナフチル基、ピリジル基、ビピリジル基またはフェナントロリル基を表し、m1は0〜3の整数である。
(III)次の一般式(10a)から(10d)で表される含窒素環式化合物残基
式(10a)から(10d)において、R10からR12はそれぞれ独立に炭素数1〜4のアルキル基、フェニル基、ビフェニル基、ナフチル基、ピリジル基、ビピリジル基またはフェナントロリル基を表し、m1からm3はそれぞれ独立に0〜3の整数である。
(IV)次の一般式(11a)から(11d)で表される含窒素環式化合物残基
式(11a)から(11d)において、R10、R11はそれぞれ独立に炭素数1〜4のアルキル基、フェニル基、ビフェニル基、ナフチル基、ピリジル基、ビピリジル基またはフェナントロリル基を表し、m1は0〜3の整数であり、m2は0〜4の整数である。
- 前記Mが、アルカリ金属である請求項1に記載の金属錯体。
- 前記アルカリ金属が、RbまたはCsである請求項2に記載の金属錯体。
- 前記請求項1から3のいずれか1項に記載の金属錯体に用いる配位性化合物。
- 前記請求項1から3のいずれか1項に記載の金属錯体からなることを特徴とする有機電界発光素子用の電子輸送材料。
- 前記電子輸送材料が、さらに金属アルコシドを含有する請求項5に記載の電子輸送材料。
- 前記金属アルコシドが、下記一般式(A)または(B)で表される請求項6に記載の電子輸送材料。
R20− M (A)
R20− M − R21 (B)
式(A)又は(B)において、R20、R21はそれぞれ独立に任意のアルキルアルコキシ基を表し、また、Mはアルカリ金属またはアルカリ土類金属を表す。
- 前記電子輸送材料が、さらにアルカリ金属イオンおよびアルカリ土類金属イオンのうちの少なくとも1種の金属イオンのハロゲン塩、炭酸塩、炭酸水素塩、水酸化物、または、炭素数1から9の有機酸塩を含有する請求項5から7のいずれか1項に記載の電子輸送材料。
- 前記請求項5から8のいずれか1項に記載の電子輸送材料をプロトン性極性溶媒に溶解してなる有機電界発光素子の電子輸送層を構築するための液状材料。
- 前記プロトン性極性溶媒が炭素数1〜10のアルコール系溶媒である請求項9に記載の液状材料。
- 前記炭素数1〜10のアルコール系溶媒が、1価または2価のアルコールである請求項10に記載の液状材料。
- 前記液状材料が、請求項1から3のいずれか1項に記載の金属錯体を0.01から10重量%含有する請求項9に記載の液状材料。
- 前記請求項5から8のいずれか1項に記載の電子輸送材料を使用してなることを特徴とする有機電界発光素子。
- 前記請求項9から12のいずれか1項に記載の液状材料を使用し、有機電界発光素子の電子輸送層を湿式で構築することを特徴とする有機電界発光素子の製造方法。
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