TWI811213B - 電荷輸送性塗料及使用其的電荷輸送性薄膜之製造方法 - Google Patents
電荷輸送性塗料及使用其的電荷輸送性薄膜之製造方法 Download PDFInfo
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- TWI811213B TWI811213B TW107111837A TW107111837A TWI811213B TW I811213 B TWI811213 B TW I811213B TW 107111837 A TW107111837 A TW 107111837A TW 107111837 A TW107111837 A TW 107111837A TW I811213 B TWI811213 B TW I811213B
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- 239000003973 paint Substances 0.000 title claims description 33
- 238000004519 manufacturing process Methods 0.000 title claims description 20
- -1 fluorinated alkyl phosphate Chemical compound 0.000 claims abstract description 216
- 238000000576 coating method Methods 0.000 claims abstract description 46
- 239000011248 coating agent Substances 0.000 claims abstract description 41
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 21
- 239000010452 phosphate Substances 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 20
- 239000000126 substance Substances 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 236
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000005843 halogen group Chemical group 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 45
- 239000000463 material Substances 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 35
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 125000000304 alkynyl group Chemical group 0.000 claims description 29
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 26
- 239000000758 substrate Substances 0.000 claims description 26
- 150000001448 anilines Chemical class 0.000 claims description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 8
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 5
- 125000005264 aryl amine group Chemical group 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 3
- JCBJVAJGLKENNC-UHFFFAOYSA-N potassium;ethoxymethanedithioic acid Chemical compound [K+].CCOC(S)=S JCBJVAJGLKENNC-UHFFFAOYSA-N 0.000 claims description 3
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 claims description 2
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- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 159
- 238000002347 injection Methods 0.000 description 58
- 239000007924 injection Substances 0.000 description 58
- 229910052757 nitrogen Inorganic materials 0.000 description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 34
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
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- 239000010409 thin film Substances 0.000 description 24
- 229910052741 iridium Inorganic materials 0.000 description 21
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 21
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- 230000005525 hole transport Effects 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 241000208340 Araliaceae Species 0.000 description 13
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 13
- 235000003140 Panax quinquefolius Nutrition 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 13
- 235000008434 ginseng Nutrition 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 12
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 9
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 8
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
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- 238000007789 sealing Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000010405 anode material Substances 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 5
- QZHXKQKKEBXYRG-UHFFFAOYSA-N 4-n-(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=CC=C(N)C=C1 QZHXKQKKEBXYRG-UHFFFAOYSA-N 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 238000010304 firing Methods 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 5
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 4
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
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- 238000009835 boiling Methods 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000010406 cathode material Substances 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
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- 229910052733 gallium Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
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- 238000004528 spin coating Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 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 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MOGTVLAYAVGOJK-UHFFFAOYSA-N 2-[5-(trifluoromethyl)-1h-1,2,4-triazol-3-yl]pyridine Chemical compound FC(F)(F)C1=NNC(C=2N=CC=CC=2)=N1 MOGTVLAYAVGOJK-UHFFFAOYSA-N 0.000 description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
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- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
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- 125000002252 acyl group Chemical group 0.000 description 3
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 239000011261 inert gas Substances 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 3
- 150000004010 onium ions Chemical class 0.000 description 3
- MQZFZDIZKWNWFX-UHFFFAOYSA-N osmium(2+) Chemical compound [Os+2] MQZFZDIZKWNWFX-UHFFFAOYSA-N 0.000 description 3
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- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- HVVRUQBMAZRKPJ-UHFFFAOYSA-N 1,3-dimethylimidazolium Chemical compound CN1C=C[N+](C)=C1 HVVRUQBMAZRKPJ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SXNILPAPBUZTIM-UHFFFAOYSA-N 1-benzylacridine Chemical compound C=1C=CC2=NC3=CC=CC=C3C=C2C=1CC1=CC=CC=C1 SXNILPAPBUZTIM-UHFFFAOYSA-N 0.000 description 2
- AOQAYBCERCSGDQ-UHFFFAOYSA-N 1-benzylthiolan-1-ium Chemical compound C=1C=CC=CC=1C[S+]1CCCC1 AOQAYBCERCSGDQ-UHFFFAOYSA-N 0.000 description 2
- DUXRDJNQKDYVNE-UHFFFAOYSA-N 2-[5-(trifluoromethyl)-1h-pyrazol-3-yl]pyridine Chemical compound N1C(C(F)(F)F)=CC(C=2N=CC=CC=2)=N1 DUXRDJNQKDYVNE-UHFFFAOYSA-N 0.000 description 2
- FPHXYKLKNOEKTQ-UHFFFAOYSA-N 4,4-diphenylbutan-2-one Chemical compound C=1C=CC=CC=1C(CC(=O)C)C1=CC=CC=C1 FPHXYKLKNOEKTQ-UHFFFAOYSA-N 0.000 description 2
- BGGDZDRRHQTSPV-UHFFFAOYSA-N 4-ethenyl-n,n-diphenylaniline Chemical compound C1=CC(C=C)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 BGGDZDRRHQTSPV-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- AGWJLDNNUJKAHP-UHFFFAOYSA-N tetrahexylphosphanium Chemical compound CCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC AGWJLDNNUJKAHP-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QQFYJXKKHBDLQV-UHFFFAOYSA-N tetrakis(2-methoxyphenyl)phosphanium Chemical compound COC1=CC=CC=C1[P+](C=1C(=CC=CC=1)OC)(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC QQFYJXKKHBDLQV-UHFFFAOYSA-N 0.000 description 1
- XLZOKVSFMDOMTL-UHFFFAOYSA-N tetrakis(3-methoxyphenyl)phosphanium Chemical compound COC1=CC=CC([P+](C=2C=C(OC)C=CC=2)(C=2C=C(OC)C=CC=2)C=2C=C(OC)C=CC=2)=C1 XLZOKVSFMDOMTL-UHFFFAOYSA-N 0.000 description 1
- KOFMFKMQSQTMTM-UHFFFAOYSA-N tetrakis(4-methylphenyl)phosphanium Chemical compound C1=CC(C)=CC=C1[P+](C=1C=CC(C)=CC=1)(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 KOFMFKMQSQTMTM-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane 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-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical group CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical group COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- QDNCLIPKBNMUPP-UHFFFAOYSA-N trimethyloxidanium Chemical compound C[O+](C)C QDNCLIPKBNMUPP-UHFFFAOYSA-N 0.000 description 1
- MGACORKJUSACCA-UHFFFAOYSA-N trinaphthalen-1-ylsulfanium Chemical compound C1=CC=C2C([S+](C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 MGACORKJUSACCA-UHFFFAOYSA-N 0.000 description 1
- HKDYXDHJQBAOAC-UHFFFAOYSA-N trinaphthalen-2-ylsulfanium Chemical compound C1=CC=CC2=CC([S+](C=3C=C4C=CC=CC4=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=C21 HKDYXDHJQBAOAC-UHFFFAOYSA-N 0.000 description 1
- XSVXWCZFSFKRDO-UHFFFAOYSA-N triphenyl-(3-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=C(C=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XSVXWCZFSFKRDO-UHFFFAOYSA-N 0.000 description 1
- DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 0.000 description 1
- LNQMQGXHWZCRFZ-UHFFFAOYSA-N triphenyl-[4-(4-triphenylsilylphenyl)phenyl]silane Chemical group C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LNQMQGXHWZCRFZ-UHFFFAOYSA-N 0.000 description 1
- HITRWHKLCHWBNZ-UHFFFAOYSA-N triphenyl-[4-(9-phenylfluoren-9-yl)phenyl]silane Chemical compound C1=CC=CC=C1C1(C=2C=CC(=CC=2)[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 HITRWHKLCHWBNZ-UHFFFAOYSA-N 0.000 description 1
- KIGXXTRUJYDDKP-UHFFFAOYSA-N triphenyl-[4-[4-(4-triphenylsilylphenyl)phenyl]phenyl]silane Chemical group C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 KIGXXTRUJYDDKP-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- AXYQQAVHPAUFQX-UHFFFAOYSA-N tris(2-methylphenyl)sulfanium Chemical compound CC1=CC=CC=C1[S+](C=1C(=CC=CC=1)C)C1=CC=CC=C1C AXYQQAVHPAUFQX-UHFFFAOYSA-N 0.000 description 1
- QKFJVDSYTSWPII-UHFFFAOYSA-N tris(4-methylphenyl)sulfanium Chemical compound C1=CC(C)=CC=C1[S+](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 QKFJVDSYTSWPII-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000007738 vacuum evaporation 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
- 238000007740 vapor deposition Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Abstract
本發明係關於提供一種含有苯胺衍生物或噻吩衍生物等電荷輸送性物質、如下述式所示之氟化烷基磷酸鎓鹽與有機溶劑之電荷輸送性塗料。
Description
本發明係關於一種電荷輸送性塗料。
於有機電致發光(以下稱為有機EL)元件中,作為發光層或電荷注入層,使用由有機化合物所成的電荷輸送性薄膜。特別為電洞注入層為擔任陽極與電洞輸送層,或者與發光層的電荷之賦予與接受角色,作為在欲達成有機EL元件之低電壓驅動及高亮度時的重要功能。
電洞注入層之形成方法大致分為代表性蒸鍍法之乾式製程,與代表性旋轉塗布法之溼式製程,若比較各這些製程時,溼式製程較能在大面積下有效率地製造出平坦性高之薄膜。因此,有機EL顯示的大面積化正進行的現今,可在溼式製程形成的電洞注入層被期待著。
有鑑於如此情事,本發明者開發出可適用於各種溼式製程的同時,亦可適用於有機EL元件之電洞注入層時可實現優良EL元件特性之薄膜的電荷輸送性材料,或使用於此的對於有機溶劑具有良好溶解性之化合物(例如參照專利文獻1~4)。
然而,有關電洞注入層用之溼式製程材料,已常被要
求著,改善特別期待對電荷輸送性賦予優良薄膜之溼式製程材料。
[專利文獻1]國際公開第2008/032616號
[專利文獻2]國際公開第2008/129947號
[專利文獻3]國際公開第2006/025342號
[專利文獻4]國際公開第2010/058777號
[專利文獻5]特開2014-205624號公報
本發明有鑑於上述情事者,以提供一種賦予具有優良電荷輸送性、平坦性及均勻性之電荷輸送性薄膜的再現性之電荷輸送性塗料為目的。
本發明者欲達到上述目的重複詳細檢討結果,發現由將電荷輸送性物質與所定氟化烷基磷酸鎓鹽溶解於有機溶劑而得之塗料,可再現性良好下得到具有優良電荷輸送性、平坦性及均勻性之電荷輸送性薄膜,以及藉由將該薄膜作為電洞注入層使用時,可得到具有優良亮度特性之有機EL元件,而完成本發明。
即,本發明為提供以下者。 1. 一種電荷輸送性塗料,其特徵為含有電荷輸送性物質、氟化烷基磷酸鎓鹽與有機溶劑,前述氟化烷基磷酸鎓鹽為含有由式(a1)所示負離子與對陽離子所成的氟化烷基磷酸鎓鹽者,(式中,R表示碳數1~10的烷基、碳數1~10的氟烷基、碳數7~10的芳烷基或碳數7~10的氟芳烷基)。 2. 如1.之電荷輸送性塗料,其中前述電荷輸送性物質為選自苯胺衍生物及噻吩衍生物的至少1種者。 3. 如2.之電荷輸送性塗料,其中前述電荷輸送性物質為苯胺衍生物。 4. 一種電荷輸送性薄膜,其特徵為由1.~3.中任一項之電荷輸送性塗料所得者。 5. 一種有機電致發光元件,其特徵為具有如4.之電荷輸送性薄膜。 6. 一種電荷輸送性薄膜之製造方法,其特徵為將如1.~3.中任一項之電荷輸送性塗料塗布於基材上,使溶劑蒸發者。
藉由使用本發明之電荷輸送性塗料,可得到具有優良的電荷輸送性、平坦性及均勻性之電荷輸送性薄膜。 又,具有如此特性之電荷輸送性薄膜,可作為以有機EL元件為主的電子裝置用薄膜適用。特別將該薄膜適用於有機EL元件的電洞注入層時,可得到低驅動電壓之有機EL元件。 且,本發明之電荷輸送性塗料為即使使用在旋轉塗布法或狹縫塗布法等可於大面積成膜之各種溼式製程時,亦可再現性良好下製造出優良電荷輸送性之薄膜,亦可充分地對應近年來的有機EL元件領域中的進展。 因此,由本發明之電荷輸送性塗料所得之薄膜因具有優良的電荷輸送性,期待可作為有機薄膜太陽電池之陽極緩衝層、帶電防止膜等使用。
[實施發明的形態]
以下對於本發明做更詳細的說明。 有關本發明之電荷輸送性塗料為含有電荷輸送性物質、氟化烷基磷酸鎓鹽與有機溶劑,氟化烷基磷酸鎓鹽為含有由式(a1)所示負離子與對陽離子所成之氟化烷基磷酸鎓鹽者。 且,所謂電荷輸送性與導電性同義,亦與電洞輸送性同義。又,本發明之電荷輸送性塗料可為其本身具有電荷輸送性者,亦可為於使用塗料而得之固體膜上具有電荷輸送性者。
對於式(a1),R表示碳數1~10的烷基、碳數1~10的氟烷基、碳數7~10的芳烷基或碳數7~10的氟芳烷基。 作為碳數1~10的烷基,可為直鏈狀、分支鏈狀、環狀中任一種,例如可舉出甲基、乙基、n-丙基、異丙基、n-丁基、異丁基、s-丁基、t-丁基、n-戊基、n-己基、n-庚基、n-辛基、n-壬基、n-癸基等碳數1~10的直鏈或分支鏈狀烷基;環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基、聯環丁基、聯環戊基、聯環己基、聯環庚基、聯環辛基、聯環壬基、聯環癸基等碳數3~10的環狀烷基等,以碳數1~8的烷基為佳,以碳數1~6的烷基為較佳。
作為碳數7~10的芳烷基,可舉出將烷基的至少1個氫原子由芳基所取代之基,例如可舉出苯甲基、1-萘伸甲基、2-萘伸甲基、苯基伸乙基、1-萘伸乙基、2-萘伸甲基等,以碳數7~9的芳烷基為佳。
作為碳數1~10的氟烷基之具體例子,可舉出將碳數1~10的烷基的至少1個氫原子由氟原子所取代之基。 作為該具體例子,可舉出氟甲基、二氟甲基、三氟甲基、五氟乙基、2,2,2-三氟乙基、七氟丙基、2,2,3,3,3-五氟丙基、2,2,3,3-四氟丙基、2,2,2-三氟-1-(三氟甲基)乙基、九氟丁基、4,4,4-三氟丁基、十一氟戊基、2,2,3,3,4,4,5,5,5-九氟戊基、2,2,3,3,4,4,5,5-八氟戊基、十三氟己基、2,2,3,3,4,4,5,5,6,6,6-十一氟己基、2,2,3,3,4,4,5,5,6,6-十氟己基、3,3,4,4,5,5,6,6,6-九氟己基等。
作為碳數7~10的氟芳烷基之具體例子,可舉出將碳數7~10的芳烷基之至少1個氫原子由氟原子所取代的基。 作為該具體例子,可舉出全氟苯甲基、五氟苯基伸甲基、七氟-1-萘伸甲基、七氟-2-萘伸甲基、七氟-1-萘伸乙基、七氟-2-萘伸乙基等。
作為在本發明中可較適合使用的上述式(a1)之負離子,可舉出下述式所示者,但並未限定於此等。
另一方面,對陽離子並無特別限定,以式(c1)所示陽離子為佳。
式(c1)中之E表示15~17族的原子價n之元素,因此n表示對應E之原子價的1~3的整數。 上述R’表示n+1個鍵結於E,此等彼此獨立表示一價有機基,但2個以上的R’彼此直接或介著-O-、-S-、-SO-、 -SO2
-、-NH-、-CO-、-COO-、-CONH-、伸烷基或者伸苯基鍵結與元素E共同可形成環結構。 作為一價有機基,雖無特別限定,以碳數1~20的烷基、碳數2~20的烯基、碳數2~20的炔基,或可由Z所取代的碳數6~20的芳基為佳,以可由Z所取代之碳數6~14的芳基為較佳。
作為碳數1~20的烷基,可為直鏈狀、分支鏈狀、環狀中任一種,除在上述碳數1~10的烷基所例示的基以外,例如可舉出n-十一烷基、n-十二烷基、n-十三烷基、n-十四烷基、n-十五烷基、n-十六烷基、n-十七烷基、n-十八烷基、n-十九烷基、n-二十烷基等,以碳數1~18的烷基為佳,以碳數1~8的烷基為較佳。
作為碳數2~20的烯基之具體例子,可舉出乙烯基、n-1-丙烯基、n-2-丙烯基、1-甲基乙烯基、n-1-丁烯基、n-2-丁烯基、n-3-丁烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1-乙基乙烯基、1-甲基-1-丙烯基、1-甲基-2-丙烯基、n-1-戊烯基、n-1-癸烯基、n-1-二十碳烯基等。 作為碳數2~20的炔基之具體例子,可舉出乙炔基、n-1-丙炔基、n-2-丙炔基、n-1-丁炔基、n-2-丁炔基、n-3-丁炔基、1-甲基-2-丙炔基、n-1-戊炔基、n-2-戊炔基、n-3-戊炔基、n-4-戊炔基、1-甲基-n-丁炔基、2-甲基-n-丁炔基、3-甲基-n-丁炔基、1,1-二甲基-n-丙炔基、n-1-己炔基、n-1-癸炔基、n-1-十五炔基、n-1-二十炔基等。
作為碳數6~20的芳基之具體例子,可舉出苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基等,以碳數6~14的芳基為佳。
Z表示碳數1~20的烷基、碳數1~8的鹵烷基、碳數2~20的烯基、碳數2~20的炔基、碳數6~20的芳基、碳數2~20的雜芳基、硝基、羥基、氰基、碳數1~8的烷氧基、碳數6~20的芳基氧基、碳數1~20的醯基、碳數1~20的醯氧基、碳數1~8的烷基硫基、碳數6~20的芳基硫基、二碳數1~8烷基胺基、二碳數6~20芳基胺基、胺基或鹵素原子。 作為這些烷基、烯基、炔基、芳基,可舉出與上述相同者。
作為鹵素原子,可舉出氟原子、氯原子、溴原子、碘原子等,以氟原子為佳。
作為碳數2~20的雜芳基之具體例子,可舉出2-噻吩基、3-噻吩基、2-呋喃基、3-呋喃基、2-噁唑基、4-噁唑基、5-噁唑基、3-異噁唑基、4-異噁唑基、5-異噁唑基等含氧雜芳基、2-噻唑基、4-噻唑基、5-噻唑基、3-異噻唑基、4-異噻唑基、5-異噻唑基等含硫雜芳基、2-咪唑基、4-咪唑基、2-吡啶基、3-吡啶基、4-吡啶基、2-吡嗪基、3-吡嗪基、5-吡嗪基、6-吡嗪基、2-嘧啶基、4-嘧啶基、5-嘧啶基、6-嘧啶基、3-噠嗪基、4-噠嗪基、5-噠嗪基、6-噠嗪基、1,2,3-三嗪-4-基、1,2,3-三嗪-5-基、1,2,4-三嗪-3-基、1,2,4-三嗪-5-基、1,2,4-三嗪-6-基、1,3,5-三嗪-2-基、1,2,4,5-四嗪-3-基、1,2,3,4-四嗪-5-基、2-喹啉基、3-喹啉基、4-喹啉基、5-喹啉基、6-喹啉基、7-喹啉基、8-喹啉基、1-異喹啉基、3-異喹啉基、4-異喹啉基、5-異喹啉基、6-異喹啉基、7-異喹啉基、8-異喹啉基、2-喹喔啉基、5-喹喔啉基、6-喹喔啉基、2-喹唑啉基、4-喹唑啉基、5-喹唑啉基、6-喹唑啉基、7-喹唑啉基、8-喹唑啉基、3-噌啉基、4-噌啉基、5-噌啉基、6-噌啉基、7-噌啉基、8-噌啉基等含氮雜芳基等。
作為碳數1~8的鹵烷基之具體例子,在上述所例示的烷基中,可舉出將碳數1~8的烷基之至少1個氫原子由鹵素原子所取代的基等。且鹵素原子可為氯、溴、碘、氟原子中任一種。其中亦以氟烷基為佳,以全氟烷基為較佳。 作為氟烷基的具體例子,可舉出與上述相同者。
作為碳數1~8的烷氧基之具體例子,可舉出甲氧基、乙氧基、n-丙氧基、i-丙氧基、c-丙氧基、n-丁氧基、i-丁氧基、s-丁氧基、t-丁氧基、n-戊氧基、n-己氧基、n-庚基氧基、n-辛基氧基等。 作為碳數6~20的芳基氧基之具體例子,可舉出苯氧基、1-萘氧基、2-萘氧基、1-蒽基氧基、2-蒽基氧基、9-蒽基氧基、1-菲基氧基、2-菲基氧基、3-菲基氧基、4-菲基氧基、9-菲基氧基等。
作為碳數1~20之醯基的具體例子,可舉出甲醯基、乙醯基、丙醯基、丁醯基、異丁醯基、香草基、異香草基、苯甲醯基等。 作為碳數1~20的醯氧基之具體例子,可舉出甲醯基氧基、乙醯氧基、丙醯基氧基、丁醯基氧基、異丁醯基氧基、香草基氧基、異香草基氧基、苯甲醯基氧基等。
作為碳數1~8的烷基硫基之具體例子,可舉出甲基硫基、乙基硫基、n-丙基硫基、異丙基硫基、n-丁基硫基、異丁基硫基、s-丁基硫基、t-丁基硫基、n-戊基硫代基、n-己基硫基、n-庚基硫基、n-辛基硫基等。 作為碳數6~20的芳基硫基之具體例子,可舉出苯基硫基、1-萘硫代基、2-萘硫代基、1-蒽基硫代基、2-蒽基硫代基、9-蒽基硫代基、1-菲基硫代基、2-菲基硫代基、3-菲基硫代基、4-菲基硫代基、9-菲基硫代基等。
作為二碳數1~8烷基胺基之具體例子,可舉出二甲基胺基、二乙基胺基、二n-丙基胺基、二i-丙基胺基、二n-丁基胺基、二i-丁基胺基、二n-戊基胺基、二n-己基胺基、二n-庚基胺基、二n-辛基胺基、甲基乙基胺基等。 作為二碳數6~20芳基胺基之具體例子,可舉出二苯基胺基、1-萘苯基胺基、二(1-萘)胺基、1-萘-2-萘胺基、二(2-萘)胺基等。
作為上述E,在15~17族的元素之中,特別以O(氧)、N(氮)、P(磷)、S(硫)或I(碘)為佳,特別以可賦予安定下容易處理的鎓離子之S、I、N、P為較佳,S、I為更較佳。作為對應之鎓離子為氧鎓、銨、鏻、硫鎓、碘鎓。
作為上述(R’)n+1
-E+
所示鎓離子之具體例子,可舉出下述者,但並未限定於此等。 作為氧鎓離子的具體例子,可舉出三甲基氧鎓、二乙基甲基氧鎓、三乙基氧鎓、四伸甲基甲基氧鎓等氧鎓;4-甲基吡喃鎓、2,4,6-三甲基吡喃鎓、2,6-二-t-丁基吡喃鎓、2,6-二苯基吡喃鎓等吡喃鎓;2,4-二甲基苯並吡喃鎓、1,3-二甲基異苯並吡喃鎓等苯並吡喃鎓及異苯並吡喃鎓等。
作為銨離子的具體例子,可舉出四甲基銨、乙基三甲基銨、二乙基二甲基銨、三乙基甲基銨、四乙基銨等四烷基銨;N,N-二甲基吡咯烷鎓、N-乙基-N-甲基吡咯烷鎓、N,N-二乙基吡咯烷鎓等吡咯烷鎓;N,N'-二甲基咪唑鎓、N,N'-二乙基咪唑鎓、N-乙基-N'-甲基咪唑鎓、1,3,4-三甲基咪唑鎓、1,2,3,4-四甲基咪唑鎓等咪唑鎓;N,N'-二甲基四氫嘧啶鎓等四氫嘧啶鎓;N,N'-二甲基嗎啉鎓等嗎啉鎓;N,N'-二乙基哌啶鎓等哌啶鎓;N-甲基吡啶鎓、N-苯甲基吡啶鎓、N-苯甲醯基吡啶鎓等吡啶鎓;N,N'-二甲基咪唑鎓等咪唑鎓;N-甲基喹啉鎓、N-苯甲基喹啉鎓、N-苯甲醯基喹啉鎓等喹啉鎓;N-甲基異喹啉鎓等異喹啉鎓;苯甲基苯並噻唑鎓、苯甲醯基苯並噻唑鎓等噻唑鎓;苯甲基吖啶鎓、苯甲醯基吖啶鎓等吖啶鎓等。
作為鏻離子的具體例子,可舉出四苯基鏻、四-p-甲苯基鏻、肆(2-甲氧基苯基)鏻、肆(3-甲氧基苯基)鏻、肆(4-甲氧基苯基)鏻等四芳基鏻;三苯基苯甲基鏻、三苯基苯甲醯基鏻、三苯基甲基鏻、三苯基丁基鏻等三芳基鏻;三乙基苯甲基鏻、三丁基苯甲基鏻、四乙基鏻、四丁基鏻、四己基鏻、三乙基苯甲醯基鏻、三丁基苯甲醯基鏻等四烷基鏻等。
作為硫鎓離子之具體例子,可舉出三苯基硫鎓、三-p-甲苯基硫鎓、三-o-甲苯基硫鎓、參(4-甲氧基苯基)硫鎓、1-萘二苯基硫鎓、2-萘二苯基硫鎓、參(4-氟苯基)硫鎓、三-1-萘硫鎓、三-2-萘硫鎓、參(4-羥基苯基)硫鎓、4-(苯基硫基)苯基二苯基硫鎓、4-(p-甲苯基硫代基)苯基二-p-甲苯基硫鎓、4-(4-甲氧基苯基硫基)苯基雙(4-甲氧基苯基)硫鎓、4-(苯基硫基)苯基雙(4-氟苯基)硫鎓、4-(苯基硫基)苯基雙(4-甲氧基苯基)硫鎓、4-(苯基硫基)苯基二-p-甲苯基硫鎓、[4-(4-聯苯基硫代基)苯基]-4-聯苯基苯基硫鎓、[4-(2-噻噸酮基硫代基)苯基]二苯基硫鎓、雙[4-(二苯基鎏)苯基]硫化物、雙[4-{雙[4-(2-羥基乙氧基)苯基]鎏}苯基]硫化物、雙{4-[雙(4-氟苯基)鎏]苯基}硫化物、雙{4-[雙(4-甲基苯基)鎏]苯基}硫化物、雙{4-[雙(4-甲氧基苯基)鎏]苯基}硫化物、4-(4-苯甲醯基-2-氯苯基硫基)苯基雙(4-氟苯基)硫鎓、4-(4-苯甲醯基-2-氯苯基硫基)苯基二苯基硫鎓、4-(4-苯甲醯基苯基硫基)苯基雙(4-氟苯基)硫鎓、4-(4-苯甲醯基苯基硫基)苯基二苯基硫鎓、7-異丙基-9-氧代-10-硫雜-9,10-二氫蒽-2-基二-p-甲苯基硫鎓、7-異丙基-9-氧代-10-硫雜-9,10-二氫蒽-2-基二苯基硫鎓、2-[(二-p-甲苯基)鎏]噻噸酮、2-[(二苯基)鎏]噻噸酮、4-(9-氧代-9H-噻噸-2-基)噻吩基-9-氧代-9H-噻噸-2-基苯基硫鎓、4-[4-(4-t-丁基苯甲醯基)苯基硫基]苯基二-p-甲苯基硫鎓、4-[4-(4-t-丁基苯甲醯基)苯基硫基]苯基二苯基硫鎓、4-[4-(苯甲醯基苯基硫基)]苯基二-p-甲苯基硫鎓、4-[4-(苯甲醯基苯基硫基)]苯基二苯基硫鎓、5-(4-甲氧基苯基)噻蒽鎓、5-苯基噻蒽鎓、5-甲苯基噻蒽鎓、5-(4-乙氧基苯基)噻蒽鎓、5-(2,4,6-三甲基苯基)噻蒽鎓等三芳基硫鎓;二苯基苯甲醯基硫鎓、二苯基4-硝基苯甲醯基硫鎓、二苯基苯甲基硫鎓、二苯基甲基硫鎓等二芳基硫鎓;苯基甲基苯甲基硫鎓、4-羥基苯基甲基苯甲基硫鎓、4-甲氧基苯基甲基苯甲基硫鎓、4-乙醯羰基氧基苯基甲基苯甲基硫鎓、4-羥基苯基(2-萘甲基)甲基硫鎓、2-萘甲基苯甲基硫鎓、2-萘甲基(1-乙氧基羰基)乙基硫鎓、苯基甲基苯甲醯基硫鎓、4-羥基苯基甲基苯甲醯基硫鎓、4-甲氧基苯基甲基苯甲醯基硫鎓、4-乙醯羰基氧基苯基甲基苯甲醯基硫鎓、2-萘甲基苯甲醯基硫鎓、2-萘十八烷基苯甲醯基硫鎓、9-蒽甲基苯甲醯基硫鎓等單芳基硫鎓;二甲基苯甲醯基硫鎓、苯甲醯基四氫噻吩鎓、二甲基苯甲基硫鎓、苯甲基四氫噻吩鎓、十八烷基甲基苯甲醯基硫鎓等三烷基硫鎓等。
作為碘鎓離子之具體例子,可舉出二苯基碘鎓、二-p-甲苯基碘鎓、雙(4-十二烷基苯基)碘鎓、雙(4-甲氧基苯基)碘鎓、(4-辛基氧基苯基)苯基碘鎓、雙(4-癸基氧基)苯基碘鎓、4-(2-羥基十四烷基氧基)苯基苯基碘鎓、4-異丙基苯基(p-甲苯基)碘鎓、4-異丁基苯基(p-甲苯基)碘鎓等。
對於本發明,上述氟化烷基磷酸鎓鹽可單獨使用1種,亦可使用2種以上之組合。 又,視必要可併用公知之其他氟化烷基磷酸鎓鹽。 且,上述氟化烷基磷酸鎓鹽,例如可由如特開2012-246456號公報等所記載的公知方法而合成。
上述氟化烷基磷酸鎓鹽在欲可容易地溶解於電荷輸送性塗料,可預先溶解於有機溶劑。 作為如此有機溶劑,可舉出伸丙基碳酸酯、伸乙基碳酸酯、1,2-伸丙基碳酸酯、二甲基碳酸酯、二乙基碳酸酯等碳酸酯類;丙酮、甲基乙基酮、環己酮、甲基異戊基酮、2-庚酮等酮類;乙二醇、乙二醇單乙酸酯、二乙二醇、二乙二醇單乙酸酯、丙二醇、丙二醇單乙酸酯、二丙二醇、二丙二醇單乙酸酯之單甲基醚、單乙基醚、單丙基醚、單丁基醚或單苯基醚等多元醇及其衍生物類;二噁烷等環式醚類;甲酸乙酯、乳酸甲酯、乳酸乙酯、乙酸甲酯、乙酸乙酯、乙酸丁酯、丙酮酸甲酯、乙醯乙酸甲酯、乙醯乙酸乙酯、丙酮酸乙酯、乙氧基乙酸乙酯、甲氧基丙酸甲酯、乙氧基丙酸乙酯、2-羥基丙酸甲酯、2-羥基丙酸乙酯、2-羥基-2-甲基丙酸乙酯、2-羥基-3-甲基丁烷酸甲酯、3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯等酯類;甲苯、二甲苯、3-苯氧基甲苯、4-甲氧基甲苯等的芳香族烴類等,這些可單獨使用,亦可使用2種以上之組合。 使用有機溶劑時,該使用比例對於上述氟化烷基磷酸鎓鹽100質量份而言,以15~1,000質量份為佳,以30~500質量份為較佳。
作為在本發明使用的電荷輸送性物質,並未特別限定,可適宜地選自過去有機EL之領域等中之公知者使用。 作為該具體例子,可舉出寡苯胺衍生物、N,N'-二芳基聯苯胺衍生物、N,N,N',N'-四芳基聯苯胺衍生物等的芳基胺衍生物、寡聚噻吩衍生物、噻吩並噻吩衍生物、噻吩並噻吩衍生物等噻吩衍生物、寡聚吡咯等吡咯衍生物等之各種電洞輸送性物質,但其中亦以芳基胺衍生物、噻吩衍生物為佳,以芳基胺衍生物為較佳,以式(1)或(2)所示苯胺衍生物為更佳。
又,電荷輸送性物質之分子量亦無特別限定,但由調整出賦予平坦性高之薄膜的均勻塗料之觀點來看,以200~9,000為佳,由得到耐溶劑性高之電荷輸送性之觀點來看,以300以上為較佳,以400以上為更佳,由調製出賦予再現性良好的平坦性高之薄膜的均勻塗料之觀點來看,以8,000以下為佳,以7,000以下為較佳,以6,000以下為更佳,以5,000以下最佳。 且,由欲防止進行薄膜化時電荷輸送性物質的分離之觀點來看,以電荷輸送性物質無分子量分布者(分散度為1)為佳(即,單一分子量者為佳)。
式(2)中,R1
及R2
為彼此獨立表示可由氫原子、鹵素原子、硝基、氰基或鹵素原子所取代之碳數1~20的烷基、碳數2~20的烯基、碳數2~20的炔基、碳數6~20的芳基或者碳數2~20的雜芳基,作為這些具體例子,可舉出與在上述式(c1)所說明之基相同者。
其中R1
及R2
亦以可由氫原子、氟原子、氰基、鹵素原子所取代之碳數1~20的烷基、可由鹵素原子所取代之碳數6~20的芳基、可由鹵素原子所取代之碳數2~20的雜芳基為佳,以可由氫原子、氟原子、氰基、鹵素原子所取代的碳數1~10的烷基、可由鹵素原子所取代之苯基為較佳,以氫原子、氟原子、甲基、三氟甲基為更佳,以氫原子為最佳。
上述式(1)及(2)中之Ph1
表示式(P1)所示基。
其中,R3
~R6
為彼此獨立表示可由氫原子、鹵素原子、硝基、氰基或鹵素原子所取代之碳數1~20的烷基、碳數2~20的烯基、碳數2~20的炔基、碳數6~20的芳基或者碳數2~20的雜芳基,作為這些具體例子,可舉出與上述式(c1)所說明之基相同者。 特別作為R3
~R6
,以可由氫原子、氟原子、氰基、鹵素原子所取代之碳數1~20的烷基、可由鹵素原子所取代之碳數6~20的芳基、可由鹵素原子所取代之碳數2~20的雜芳基為佳,以可由氫原子、氟原子、氰基、鹵素原子所取代之碳數1~10的烷基、可由鹵素原子所取代之苯基為較佳,可由氫原子、氟原子、甲基、三氟甲基者為更佳,以氫原子為最佳。
以下,雖舉出作為Ph1
的較佳基之具體例子,但並未限定於此等。
上述式(1)中之Ar1
為彼此獨立表示式(B1)~(B11)中任一所示基,但特佳為式(B1’)~(B11’)中任一所示基。
其中,R7
~R27
、R30
~R51
及R53
~R154
為彼此獨立表示可由氫原子、鹵素原子、硝基、氰基或鹵素原子所取代之二苯基胺基、碳數1~20的烷基、碳數2~20的烯基、碳數2~20的炔基、碳數6~20的芳基或者碳數2~20的雜芳基,R28
及R29
為彼此獨立表示可由Z1
所取代之碳數6~20的芳基或碳數2~20的雜芳基,R52
表示可由氫原子、Z4
所取代之碳數1~20的烷基、碳數2~20的烯基或者碳數2~20的炔基,或可由Z1
所取代之碳數6~20的芳基或者碳數2~20的雜芳基,Z1
表示可由鹵素原子、硝基、氰基或Z2
所取代之碳數1~20的烷基、碳數2~20的烯基或者碳數2~20的炔基,Z2
表示可由鹵素原子、硝基、氰基或Z3
所取代之碳數6~20的芳基或者碳數2~20的雜芳基,Z3
表示鹵素原子、硝基或氰基,Z4
表示可由鹵素原子、硝基、氰基或Z5
所取代之碳數6~20的芳基或者碳數2~20的雜芳基,Z5
表示可由鹵素原子、硝基、氰基或Z3
所取代之碳數1~20的烷基、碳數2~20的烯基或者碳數2~20的炔基,作為這些鹵素原子、碳數1~20的烷基、碳數2~20的烯基、碳數2~20的炔基、碳數6~20的芳基及碳數2~20的雜芳基之具體例子,可舉出與上述式(c1)所說明之基相同者。
特別作為R7
~R27
、R30
~R51
及R53
~R154
,以可由氫原子、氟原子、氰基、鹵素原子所取代之二苯基胺基、可由鹵素原子所取代之碳數1~20的烷基、可由鹵素原子所取代之碳數6~20的芳基、可由鹵素原子所取代之碳數2~20的雜芳基為佳,以可由氫原子、氟原子、氰基、鹵素原子所取代之碳數1~10的烷基、可由鹵素原子所取代之苯基為較佳,以氫原子、氟原子、甲基、三氟甲基為更佳,以氫原子為最佳。 又,作為R28
及R29
,以可由Z1
所取代之碳數6~14的芳基、可由Z1
所取代之碳數2~14的雜芳基為佳,以可由Z1
所取代之碳數6~14的芳基為較佳,以可由Z1
所取代之苯基、可由Z1
所取代之1-萘基、可由Z1
所取代之2-萘基為更佳。 而作為R52
可為氫原子,可由Z1
所取代之碳數6~20的芳基、可由Z1
所取代之碳數2~20的雜芳基、以可由Z4
所取代之碳數1~20的烷基為佳,以氫原子、可由Z1
所取代之碳數6~14的芳基、可由Z1
所取代之碳數2~14的雜芳基、可由Z4
所取代之碳數1~10的烷基為佳,以氫原子、可由Z1
所取代之碳數6~14的芳基、可由Z1
所取代之碳數2~14的含氮雜芳基、可由Z4
所取代之碳數1~10的烷基為較佳,以氫原子、可由Z1
所取代之苯基、可由Z1
所取代之1-萘基、可由Z1
所取代之2-萘基、可由Z1
所取代之2-吡啶基、可由Z1
所取代之3-吡啶基、可由Z1
所取代之4-吡啶基、可由Z4
所取代之甲基為更佳。
又,Ar4
為彼此獨立表示二碳數6~20的芳基胺基所取代之碳數6~20的芳基。 作為碳數6~20的芳基、二碳數6~20的芳基胺基之具體例子,可舉出與式(c1)所說明的基之相同者。 作為Ar4
以苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基、p-(二苯基胺基)苯基、p-(1-萘苯基胺基)苯基、p-(二(1-萘)胺基)苯基、p-(1-萘-2-萘胺基)苯基、p-(二(2-萘)胺基)苯基為佳,以p-(二苯基胺基)苯基為較佳。
以下雖舉出作為Ar1
之較佳基的具體例子,但並未限定於此等。
(式中,R52
表示與上述相同意思)
上述式(1)中之Ar2
為彼此獨立表示式(A1)~(A18)中任一所示基。
其中,式中,R155
表示、氫原子、可由Z4
所取代之碳數1~20的烷基、碳數2~20的烯基或者碳數2~20的炔基,或可由Z1
所取代之碳數6~20的芳基或者碳數2~20的雜芳基,R156
及R157
為彼此獨立表示可由Z1
所取代之碳數6~20的芳基或碳數2~20的雜芳基,DPA表示二苯基胺基,Ar4
、Z1
、Z3
~Z5
表示與上述相同意思。作為這些鹵素原子、碳數1~20的烷基、碳數2~20的烯基、碳數2~20的炔基、碳數6~20的芳基及碳數2~20的雜芳基之具體例子可舉出作為這些具體例子與在上述式(c1)所說明的相同基。
特別作為R155
以氫原子、可由Z1
所取代之碳數6~20的芳基、可由Z1
所取代之碳數2~20的雜芳基、可由Z4
所取代之碳數1~20的烷基為佳,以氫原子、可由Z1
所取代之碳數6~14的芳基、可由Z1
所取代之碳數2~14的雜芳基、可由Z4
所取代之碳數1~10的烷基為較佳,以氫原子、可由Z1
所取代之碳數6~14的芳基、可由Z1
所取代之碳數2~14的含氮雜芳基、可由Z4
所取代之碳數1~10的烷基為更佳,以氫原子、可由Z1
所取代之苯基、可由Z1
所取代之1-萘基、可由Z1
所取代之2-萘基、可由Z1
所取代之2-吡啶基、可由Z1
所取代之3-吡啶基、可由Z1
所取代之4-吡啶基、可由Z4
所取代之甲基為更較佳。 又,作為R156
及R157
,以可由Z1
所取代之碳數6~14的芳基、可由Z1
所取代之碳數2~14的雜芳基為佳,以可由Z1
所取代之碳數6~14的芳基為較佳,以可由Z1
所取代之苯基、可由Z1
所取代之1-萘基、可由Z1
所取代之2-萘基為更佳。
以下,舉出作為Ar2
的較佳基之具體例子,但並未限定於此等。
(式中,R155
表示與上述相同意思。)
且,對於式(1),若考慮到所得之苯胺衍生物的合成之容易性,以Ar1
全為相同基、Ar2
全為相同基者為佳,以Ar1
及Ar2
全為相同基者為較佳。即,式(1)所示苯胺衍生物以式(1-1)所示苯胺衍生物為較佳。 又,作為如後述之原料化合物,由可使用比較便宜的雙(4-胺基苯基)胺而比較簡便地合成,同時對有機溶劑具有優良溶解性來看,式(1)所示苯胺衍生物以式(1-1)所示苯胺衍生物為佳。
式(1-1)中,Ph1
及k表示與上述相同意思,Ar5
同時表示各式(D1)~(D13)中任一所示基,但特佳為式(D1’)~(D13’)中任一所示基者。 且,作為Ar5
的具體例子,作為Ar1
的較佳基之具體例子,可舉出與上述同様者。
(式中,R28
、R29
、R52
、Ar4
及DPA表示與上述相同意思。)
(式中,R28
、R29
、R52
、Ar4
及DPA表示與上述相同意思。)
又,由如後述作為原料化合物使用比較便宜的價錢的雙(4-胺基苯基)胺,以比較簡便而合成之同時,所得之苯胺衍生物對於有機溶劑具有優良的溶解性來看,式(1)所示苯胺衍生物以式(1-2)所示苯胺衍生物為佳。
上述Ar6
同時表示式(E1)~(E14)中任一所示基。
(式中、R52
表示與上述相同意思。)
上述式(2)中之Ar3
表示式(C1)~(C8)中任一所示基,特佳為(C1’)~(C8’)中任一所示基。
上述式(1)中之k表示1~10的整數,但由提高化合物對於有機溶劑之溶解性之觀點來看,以1~5為佳,以1~3為較佳,以1或2為更佳,以1為最佳。 上述式(2)中之l表示1或2。
且對於R28
、R29
、R52
及R155
~R157
,Z1
以鹵素原子、硝基、氰基、可由Z2
所取代之碳數1~10的烷基、可由Z2
所取代之碳數2~10的烯基、可由Z2
所取代之碳數2~10的炔基為佳,以鹵素原子、硝基、氰基、可由Z2
所取代之碳數1~3的烷基、可由Z2
所取代之碳數2~3的烯基、可由Z2
所取代之碳數2~3的炔基為較佳,以氟原子、可由Z2
所取代之碳數1~3的烷基、可由Z2
所取代之碳數2~3的烯基、可由Z2
所取代之碳數2~3的炔基為更佳。
對於R28
、R29
、R52
及R155
~R157
,Z4
以鹵素原子、硝基、氰基、可由Z5
所取代之碳數6~14的芳基為佳,以鹵素原子、硝基、氰基、可由Z5
所取代之碳數6~10的芳基為較佳,以氟原子、可由Z5
所取代之碳數6~10的芳基為更佳,以氟原子、可由Z5
所取代之苯基為特佳。
對於R28
、R29
、R52
及R155
~R157
,Z2
以鹵素原子、硝基、氰基、可由Z3
所取代之碳數6~14的芳基為佳,以鹵素原子、硝基、氰基、可由Z3
所取代之碳數6~10的芳基為較佳,以氟原子、可由Z3
所取代之碳數6~10的芳基為更佳,以氟原子、可由Z3
所取代之苯基為特佳。
對於R28
、R29
、R52
及R155
~R157
,Z5
以鹵素原子、硝基、氰基、可由Z3
所取代之碳數1~10的烷基、可由Z3
所取代之碳數2~10的烯基、可由Z3
所取代之碳數2~10的炔基為佳,以鹵素原子、硝基、氰基、可由Z3
所取代之碳數1~3的烷基、可由Z3
所取代之碳數2~3的烯基、可由Z3
所取代之碳數2~3的炔基為較佳,以氟原子、可由Z3
所取代之碳數1~3的烷基、可由Z3
所取代之碳數2~3的烯基、可由Z3
所取代之碳數2~3的炔基為更佳。
對於R28
、R29
、R52
及R155
~R157
,Z3
以鹵素原子為佳,以氟原子為較佳。
另一方面,對於R7
~R27
、R30
~R51
及R53
~R154
,Z1
以鹵素原子、硝基、氰基、可由Z2
所取代之碳數1~3的烷基、可由Z2
所取代之碳數2~3的烯基、可由Z2
所取代之碳數2~3的炔基為佳,以鹵素原子、可由Z2
所取代之碳數1~3的烷基為較佳,以氟原子、可由Z2
所取代之甲基為更佳。
對於R7
~R27
、R30
~R51
及R53
~R154
,Z4
以鹵素原子、硝基、氰基、可由Z5
所取代之碳數6~10的芳基為佳,以鹵素原子、可由Z5
所取代之碳數6~10的芳基為較佳,以氟原子、可由Z5
所取代之苯基為更佳。
對於R7
~R27
、R30
~R51
及R53
~R154
,Z2
以鹵素原子、硝基、氰基、可由Z3
所取代之碳數6~10的芳基為佳,以鹵素原子、可由Z3
所取代之碳數6~10的芳基為較佳,以氟原子、Z3
所取代之苯基為更佳。
對於R7
~R27
、R30
~R51
及R53
~R154
,Z5
以鹵素原子、硝基、氰基、可由Z3
所取代之碳數1~3的烷基、可由Z3
所取代之碳數2~3的烯基、可由Z3
所取代之碳數2~3的炔基為佳,以鹵素原子、可由Z3
所取代之碳數1~3的烷基為較佳,以氟原子、可由Z3
所取代之甲基為更佳。
對於R7
~R27
、R30
~R51
及R53
~R154
,Z3
以鹵素原子為佳,以氟原子為較佳。
作為上述R52
及R155
之較佳基的具體例子,可舉出以下基,但並未限定於此等。
上述烷基、烯基及炔基的碳數以10以下為佳,較佳為6以下,更佳為4以下。 又,上述芳基及雜芳基的碳數以14以下為佳,較佳為10以下,更佳為6以下。
上述式(1)所示苯胺衍生物可將式(3)所示胺化合物與式(4)所示芳基化合物在觸媒存在下進行反應而製造。
(式中,X表示鹵素原子或擬鹵素基,Ar1
、Ar2
、Ph1
及k表示與上述相同意思。)
特別為式(1-1)所示苯胺衍生物可由將式(5)所示胺化合物與式(6)所示芳基化合物在觸媒存在下進行反應而製造。
(式中,X、Ar5
、Ph1
及k表示與上述相同意思。)
又,式(1-2)所示苯胺衍生物可由將雙(4-胺基苯基)胺式(7)所示芳基化合物在觸媒存在下進行反應而製造。
(式中,X及Ar6
表示與上述相同意思。)
另一方面,上述式(2)所示苯胺衍生物可由將式(8)所示胺化合物與式(9)所示芳基化合物在觸媒存在下進行反應而製造。
(式中,X、R1
、R2
、Ar3
、Ph1
及l表示與上述相同意思。)
作為鹵素原子,可舉出與上述相同者。 作為擬鹵素基,可舉出甲烷磺醯基氧基、三氟甲烷磺醯基氧基、九氟丁烷磺醯基氧基等(氟)烷基磺醯基氧基;苯磺醯基氧基、甲苯磺醯基氧基等芳香族磺醯基氧基等。
式(3)、(5)或者(8)所示胺化合物或雙(4-胺基苯基)胺與式(4)、(6)、(7)或(9)所示芳基化合物之裝入比,對於胺化合物或雙(4-胺基苯基)胺之全NH基的物質量而言,可將芳基化合物設定在當量以上,以1~1.2當量程度為佳。
作為使用於上述反應的觸媒,例如可舉出氯化銅、溴化銅、碘化銅等銅觸媒;Pd(PPh3
)4
(肆(三苯基膦)鈀)、Pd(PPh3
)2
Cl2
(雙(三苯基膦)二氯鈀)、Pd(dba)2
(雙(二苯亞甲基丙酮)鈀)、Pd2
(dba)3
(參(二苯亞甲基丙酮)二鈀)、Pd(P-t-Bu3
)2
(雙(三(t-丁基膦))鈀)、Pd(OAc)2
(乙酸鈀)等鈀觸媒等。這些觸媒可單獨使用,亦可組合2種以上使用。又,這些觸媒亦可與公知的適當配位一起使用。 作為如此配位子,可舉出三苯基膦、三-o-甲苯基膦、二苯基甲基膦、苯基二甲基膦、三甲基膦、三乙基膦、三丁基膦、三-tert-丁基膦、二-t-丁基(苯基)膦、二-tert-丁基(4-二甲基胺基苯基)膦、1,2-雙(二苯基膦)乙烷、1,3-雙(二苯基膦)丙烷、1,4-雙(二苯基膦)丁烷、1,1'-雙(二苯基膦)二茂鐵等3級膦、三甲基亞磷酸酯、三乙基亞磷酸酯、三苯基亞磷酸酯等3級亞磷酸酯等。
觸媒之使用量對於式(4)、(6)、(7)或(9)所示芳基化合物1mol而言,可設定為0.2mol程度,以0.15mol程度為佳。 又,使用配位子時,該使用量對於所使用的金屬錯體而言為0.1~5當量,以1~2當量為佳。
由原料化合物皆為固體之情況或者可有效率地得到目的之苯胺衍生物之觀點來看,上述各反應在溶劑中進行。使用溶劑時,該種類若對反應不會造成壞影響即可,並無特別限制。作為具體例子,可舉出脂肪族烴類(戊烷、n-己烷、n-辛烷、n-癸烷、十氫萘等)、鹵素化脂肪族烴類(氯仿、二氯甲烷、二氯乙烷、四氯化碳素等)、芳香族烴類(苯、硝基苯、甲苯、o-二甲苯、m-二甲苯、p-二甲苯、三甲苯等)、鹵素化芳香族烴類(氯苯、溴苯、o-二氯苯、m-二氯苯、p-二氯苯等)、醚類(二乙基醚、二異丙基醚、t-丁基甲基醚、四氫呋喃、二噁烷、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷等)、酮類(丙酮、甲基乙基酮、甲基異丁基酮、二-n-丁基酮、環己酮等)、醯胺類(N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等)、內醯胺及內酯類(N-甲基吡咯啶酮、γ-丁內酯等)、尿素類(N,N-二甲基咪唑啉酮、四甲基脲等)、亞碸類(二甲基亞碸、環丁碸等)、腈類(乙腈、丙腈、丁腈等)等,這些溶劑可單獨使用,亦可混合2種以上使用。
反應溫度可適宜地設定為自使用的溶劑之熔點至沸點的範圍即可,特佳為0~200℃程度,以20~150℃為較佳。 反應終了後,依據常法進行後處理,可得到作為目的之苯胺衍生物。
對於上述式(1)所示苯胺衍生物之製造方法,作為原料使用的式(3')所示胺化合物可藉由將式(10)所示胺化合物與式(11)所示芳基化合物在觸媒存在下進行反應而有效率地製造。
(式中,X、Ar1
、Ph1
及k表示與上述相同意思。但,2個Ar1
不會同時成為式(B1)所示基。)
式(3')所示胺化合物之上述製造方法雖為將式(10)所示胺化合物與式(11)所示芳基化合物進行偶合反應者,但式(10)所示胺化合物與式(11)所示芳基化合物之裝入量以物質量比表示時,對於胺化合物1,以芳基化合物2~2.4程度為佳。 其他,有關於該偶合反應中之觸媒、配位子、溶劑、反應溫度等各條件,與對於式(1)所示苯胺衍生物之製造方法所說明的上述條件相同。
且,製造式(1)中,Ar1
為R52
表示氫原子之式(B4)所示基或式(B10)所示基,或者Ar2
表示式(A12)所示基或R155
(含有式(1-1)中之R52
)表示氫原子之式(A16)所示基的苯胺衍生物時,對於上述反應,可使用於胺基上具有公知保護基之芳基化合物。
以下,可舉出式(1)或(2)所示苯胺衍生物之具體例子,但並未限定於此等。且,式及表中,「Me」表示甲基,「Et」表示乙基,「Prn
」表示n-丙基,「Pri
」表示異丙基,「Bun
」表示正丁基,「Bui
」表示異丁基,「Bus
」表示第二丁基,「But
」表示第三丁基,「DPA」表示二苯基胺基,「SBF」表示9,9'-螺雙[9H-芴]-2-基。
本發明中,上述氟化烷基磷酸鎓鹽與電荷輸送性物質之比率在物質量(莫耳)比時為電荷輸送性物質:氟化烷基磷酸鎓鹽=1:0.1~10程度。
作為使用於調製電荷輸送性塗料時的有機溶劑,可使用可良好地溶解電荷輸送性物質及氟化烷基磷酸鎓鹽之高溶解性溶劑。 作為如此高溶解性溶劑,例如可舉出環己酮、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、1,3-二甲基-2-咪唑啉酮、二乙二醇單甲基醚、3-苯氧基甲苯、4-甲氧基甲苯、甲苯、苯甲醚、環己基苯、安息香酸甲基、四氫萘、異佛爾酮等有機溶劑,但並未限定於此等。這些溶劑可單獨使用1種,或混合2種以上使用,該使用量對於使用在塗料的溶劑全體而言可使用5~100質量%。
又,對於本發明,對於塗料具有在25℃之10~200mPa・s,特別為35~150mPa・s之黏度,藉由含有在常壓(大氣壓)沸点為50~300℃,特別為150~250℃之高黏度有機溶劑的至少1種類時,可容易調整塗料之黏度,其結果可賦予優良再現性的平坦性高之薄膜,可配合塗布方法而調製塗料。 作為高黏度有機溶劑,例如可舉出環己醇、乙二醇、乙二醇二縮水甘油基醚、1,3-辛二醇、二乙二醇、二丙二醇、三乙二醇、三丙二醇、1,3-丁二醇、2,3-丁二醇、1,4-丁二醇、丙二醇、己二醇等,但並未限定於此等。這些溶劑可單獨使用,亦可混合2種以上使用。 對於使用於本發明之塗料的溶劑全體而言,高黏度有機溶劑之添加比例若為不會析出固體的範圍內者即可,對於不析出固體的範圍下,添加比例以5~90質量%為佳。
且,對於基板之濕潤性的提高,以溶劑之表面張力的調整、極性的調整及沸點的調整等目的下,可將其他溶劑以對於使用於塗料之溶劑全體而言的1~90質量%,較佳為1~50質量%的比例下混合。 作為如此溶劑,例如可舉出丙二醇單甲基醚、乙二醇單丁基醚、二乙二醇二乙基醚、二乙二醇二甲基醚、二乙二醇單乙基醚乙酸酯、二乙二醇單丁基醚乙酸酯、二丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、二乙二醇單乙基醚、二丙酮醇、γ-丁內酯、乙基乳酸酯、n-己基乙酸酯等,但並未限定於此等。這些溶劑可單獨使用1種,或混合2種以上後使用。
本發明之塗料之黏度為配合所製作的薄膜之厚度等或固體成分濃度而適宜設定者,通常為在25℃為1~50mPa・s,該表面張力通常為20~50mN/m。 又,電荷輸送性塗料之固體成分濃度雖為勘查塗料之黏度及表面張力等或所製作之薄膜厚度等而適宜設定者,通常為0.1~10.0質量%程度,若考慮到提高塗料之塗布性時,以0.5~5.0質量%程度為佳,較佳為1.0~3.0質量%程度。
作為塗料之調製法,雖無特別限定,例如先將上述氟化烷基磷酸鎓鹽溶解於溶劑中,於此依序加入電荷輸送性物質之方法,或將上述氟化烷基磷酸鎓鹽與電荷輸送性物質之混合物溶解於溶劑之方法可舉出。 又,若有機溶劑為複數時,例如於均勻溶解上述氟化烷基磷酸鎓鹽與電荷輸送性物質之溶劑中,首先溶解此等,於此可再加入其他溶劑,於複數有機溶劑之混合溶劑中,亦可依序溶解上述氟化烷基磷酸鎓鹽、電荷輸送性物質,或者同時溶解這些。
對於本發明,電荷輸送性塗料由可再現性優良地得到高平坦性薄膜之觀點來看,將上述氟化烷基磷酸鎓鹽、電荷輸送性化合物等溶解於有機溶劑後,使用亞微米級之濾器等進行過濾為佳。
本發明之電荷輸送性薄膜為,藉由將上述說明的電荷輸送性塗料塗布於基材上並燒成後可形成基材上。 作為塗料之塗布方法,並無特別限定,可舉出浸漬法、旋轉塗布法、轉印印刷法、輥塗布法、刷毛塗布、噴墨法、噴霧法、狹縫塗布法等,配合塗布方法可調節塗料之黏度及表面張力者為佳。
又,使用本發明之塗料時,燒成環境亦無特別限定,不僅可在大氣環境下,亦可在氮等惰性氣體或真空中得到具有均勻成膜面及高電荷輸送性之薄膜,藉由電荷輸送性化合物等種類,將塗料在大氣環境下燒成時,可得到再現性更佳的具有高電荷輸送性之薄膜。
燒成溫度可勘查所得之薄膜的用途、賦予所得之薄膜的電荷輸送性之程度、溶劑種類或沸點等,適宜地設定在100~260℃程度之範圍內者,將所得之薄膜作為有機EL元件之電洞注入層使用時,以140~250℃程度為佳,以145~240℃程度為較佳。 且,燒成時,在以表現較高均勻成膜性,或在基材上進行反應之目的下,可設定2段階以上之溫度變化,加熱則可使用例如加熱板或烤箱等適當機器進行。
電荷輸送性薄膜之膜厚並無特別限定,作為有機EL元件的電洞注入層、電洞輸送層或者電洞注入輸送層使用時,以5~200nm為佳。作為使膜厚產生變化的方法,有使塗料中之固體成分濃度產生變化,或改變塗布時之基板上的溶液量等方法。
本發明之有機EL元件為具有一對電極,於這些電極之間,具有上述本發明之電荷輸送性薄膜者。 作為有機EL元件之代表性構成,可舉出以下(a)~(f),但並未限定於此等。且,對於下述構成,視必要可於發光層與陽極之間設置電子阻擋層等,於發光層與陰極之間設定孔(電洞)阻擋層等。又,電洞注入層、電洞輸送層或者電洞注入輸送層亦可兼備作為電子阻擋層等功能,電子注入層、電子輸送層或者電子注入輸送層可兼備孔(電洞)阻擋層等功能。 (a)陽極/電洞注入層/電洞輸送層/發光層/電子輸送層/電子注入層/陰極 (b)陽極/電洞注入層/電洞輸送層/發光層/電子注入輸送層/陰極 (c)陽極/電洞注入輸送層/發光層/電子輸送層/電子注入層/陰極 (d)陽極/電洞注入輸送層/發光層/電子注入輸送層/陰極 (e)陽極/電洞注入層/電洞輸送層/發光層/陰極 (f)陽極/電洞注入輸送層/發光層/陰極
所謂「電洞注入層」、「電洞輸送層」及「電洞注入輸送層」為,形成於發光層與陽極之間的層,其為具有將電洞自陽極輸送至發光層之功能者,於發光層與陽極之間,僅設1層的置電洞輸送性材料之層時,此為「電洞注入輸送層」,於發光層與陽極之間,設置2層以上的電洞輸送性材料之層時,接近陽極之層為「電洞注入層」,此以外的層為「電洞輸送層」。特別為電洞注入(輸送)層不僅具有自陽極之電洞受容性,亦使用具有優良對電洞輸送(發光)層之電洞注入性的薄膜。 所謂「電子注入層」、「電子輸送層」及「電子注入輸送層」表示於發光層與陰極之間所形成的層,其為具有將電子自陰極輸送至發光層的功能者,於發光層與陰極之間,僅設置1層的電子輸送性材料之層時,此為「電子注入輸送層」,於發光層與陰極之間設置2層以上的電子輸送性材料之層時,接近陰極之層為「電子注入層」,此以外的層為「電子輸送層」。 所謂「發光層」為具有發光功能之有機層,採用摻合系統時,含有主材料與摻合物材料。此時,主材料為主要具有促進電子與電洞之再鍵結,具有將激起子封閉於發光層內之功能,摻合物材料為具有將在再鍵結所得之激起子可有效率地發光之功能。燐光元件之情況,主材料為主要具有將在摻合時所生成的激起子封閉於發光層內之功能。
本發明之電荷輸送性薄膜中有機EL元件,可作為電洞注入層、電洞輸送層、電洞注入輸送層適用時,可適用於作為電洞注入層。
使用本發明之電荷輸送性塗料而製造有機EL元件時的使用材料或作為製作方法,可舉出下述所示者,但並未限定於此等。 所使用的電極基板以預先藉由洗劑、醇、純水等進行液體洗淨的淨化為佳,例如在陽極基板可於使用前進行UV臭氧處理、氧-電漿處理等表面處理為佳。但,陽極材料係以有機物作為主成分時,無需進行表面處理。
具有由本發明之電荷輸送性塗料所得之薄膜所成的電洞注入層之有機EL元件的製作方法之例子如以下所示。 藉由上述方法,於陽極基板上塗布本發明之電荷輸送性塗料並燒成後,於電極上製作出電洞注入層。 於該電洞注入層之上,以電洞輸送層、發光層、電子輸送層、電子注入層、陰極的順序設置。電洞輸送層、發光層、電子輸送層及電子注入層可配合所使用的材料之特性等,可藉由蒸鍍法、塗布法(溼式製程)中任一方法形成即可。 作為陽極材料,可舉以銦錫酸化物(ITO)、銦鋅酸化物(IZO)作為代表的透明電極,或以鋁作為代表之金屬或由這些合金等所構成之金屬陽極,以進行平坦化處理者為佳。亦可使用具有高電荷輸送性之聚噻吩衍生物或聚苯胺衍生物。 且,作為構成金屬陽極之其他金屬,可舉出鈧、鈦、釩、鉻、錳、鐵、鈷、鎳、銅、鋅、鎵、釔、鋯、鈮、鉬、釕、銠、鈀、鎘、銦、鈧、鑭、鈰、鐠、釹、鉤、釤、銪、釓、鋱、鏑、鈥、鉺、銩、鐿、鉿、鉈、鎢、錸、鋨、銥、鉑、金、鈦、鉛、鉍或這些合金等,但並未限定於此等。
作為形成電洞輸送層之材料,可舉出(三苯基胺)二聚物衍生物、[(三苯基胺)二聚物]螺二聚物、N,N'-雙(萘-1-基)-N,N'-雙(苯基)-聯苯胺(α-NPD)、N,N'-雙(萘-2-基)-N,N'-雙(苯基)-聯苯胺、N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-聯苯胺、N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-9,9-螺聯芴、N,N'-雙(萘-1-基)-N,N'-雙(苯基)-9,9-螺聯芴、N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-9,9-二甲基-芴、N,N'-雙(萘-1-基)-N,N'-雙(苯基)-9,9-二甲基-芴、N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-9,9-二苯基-芴、N,N'-雙(萘-1-基)-N,N'-雙(苯基)-9,9-二苯基-芴、N,N'-雙(萘-1-基)-N,N'-雙(苯基)-2,2'-二甲基聯苯胺、2,2',7,7'-肆(N,N-二苯基胺基)-9,9-螺聯芴、9,9-雙[4-(N,N-雙-聯苯基-4-基-胺基)苯基]-9H-芴、9,9-雙[4-(N,N-雙-萘-2-基-胺基)苯基]-9H-芴、9,9-雙[4-(N-萘-1-基-N-苯基胺基)-苯基]-9H-芴、2,2',7,7'-肆[N-萘基(苯基)-胺基]-9,9-螺聯芴、N,N'-雙(菲-9-基)-N,N'-雙(苯基)-聯苯胺、2,2'-雙[N,N-雙(聯苯基-4-基)胺基]-9,9-螺聯芴、2,2'-雙(N,N-二苯基胺基)-9,9-螺聯芴、二-[4-(N,N-二(p-甲苯基)胺基)-苯基]環己烷、2,2',7,7'-四(N,N-二(p-甲苯基))胺基-9,9-螺聯芴、N,N,N',N'-四-萘-2-基-聯苯胺、N,N,N',N'-四-(3-甲基苯基)-3,3'-二甲基聯苯胺、N,N'-二(萘基)-N,N'-二(萘-2-基)-聯苯胺、N,N,N',N'-四(萘基)-聯苯胺、N,N'-二(萘-2-基)-N,N'-二苯基聯苯胺-1,4-二胺、N1
,N4
-二苯基-N1
,N4
-二(m-甲苯基)苯-1,4-二胺、N2
,N2
,N6
,N6
-四苯基萘-2,6-二胺、參(4-(喹啉-8-基)苯基)胺、2,2'-雙(3-(N,N-二(p-甲苯基)胺基)苯基)聯苯基、4,4',4”-參[3-甲基苯基(苯基)胺基]三苯基胺(m-MTDATA)、4,4',4”-參[1-萘(苯基)胺基]三苯基胺(1-TNATA)等三芳基胺類、5,5”-雙-{4-[雙(4-甲基苯基)胺基]苯基}-2,2':5',2”-三噻吩(BMA-3T)等寡聚噻吩類等電洞輸送性低分子材料等。
作為形成發光層之材料,可舉出參(8-羥基喹啉)鋁(III)(Alq3
)、雙(8-羥基喹啉)鋅(II)(Znq2
)、雙(2-甲基-8-羥基喹啉)-4-(p-苯基苯酚)鋁(III)(BAlq)、4,4'-雙(2,2-二苯基乙烯基)聯苯基、9,10-二(萘-2-基)蒽、2-t-丁基-9,10-二(萘-2-基)蒽、2,7-雙[9,9-二(4-甲基苯基)-芴-2-基]-9,9-二(4-甲基苯基)芴、2-甲基-9,10-雙(萘-2-基)蒽、2-(9,9-螺聯芴-2-基)-9,9-螺聯芴、2,7-雙(9,9-螺聯芴-2-基)-9,9-螺聯芴、2-[9,9-二(4-甲基苯基)-芴-2-基]-9,9-二(4-甲基苯基)芴、2,2'-二芘基-9,9-螺聯芴、1,3,5-參(芘-1-基)苯、9,9-雙[4-(芘基)苯基]-9H-芴、2,2'-雙(9,10-二苯基蒽)、2,7-二芘基-9,9-螺聯芴、1,4-二(芘-1-基)苯、1,3-二(芘-1-基)苯、6,13-二(聯苯基-4-基)五苯、3,9-二(萘-2-基)苝、3,10-二(萘-2-基)苝、參[4-(芘基)-苯基]胺、10,10'-二(聯苯基-4-基)-9,9'-聯蒽、N,N'-二(萘-1-基)-N,N'-二苯基-[1,1':4',1'':4'',1'''-季苯基]-4,4'''-二胺、4,4'-二[10-(萘-1-基)蒽-9-基]聯苯基、二苯並{[f,f']-4,4',7,7'-四苯基}二茚並[1,2,3-cd:1',2',3'-lm]苝、1-(7-(9,9'-聯蒽-10-基)-9,9-二甲基-9H-芴-2-基)芘、1-(7-(9,9'-聯蒽-10-基)-9,9-二己基-9H-芴-2-基)芘、1,3-雙(咔唑-9-基)苯、1,3,5-參(咔唑-9-基)苯、4,4',4”-參(咔唑-9-基)三苯基胺、4,4'-雙(咔唑-9-基)聯苯基(CBP)、4,4'-雙(咔唑-9-基)-2,2'-二甲基聯苯基、2,7-雙(咔唑-9-基)-9,9-二甲基芴、2,2',7,7'-肆(咔唑-9-基)-9,9-螺聯芴、2,7-雙(咔唑-9-基)-9,9-二(p-甲苯基)芴、9,9-雙[4-(咔唑-9-基)-苯基]芴、2,7-雙(咔唑-9-基)-9,9-螺聯芴、1,4-雙(三苯基矽基)苯、1,3-雙(三苯基矽基)苯、雙(4-N,N-二乙基胺基-2-甲基苯基)-4-甲基苯基甲烷、2,7-雙(咔唑-9-基)-9,9-二辛基芴、4,4”-二(三苯基矽基)-p-三聯苯、4,4'-二(三苯基矽基)聯苯基、9-(4-t-丁基苯基)-3,6-雙(三苯基矽基)-9H-咔唑、9-(4-t-丁基苯基)-3,6-雙三苯甲基-9H-咔唑、9-(4-t-丁基苯基)-3,6-雙(9-(4-甲氧基苯基)-9H-芴-9-基)-9H-咔唑、2,6-雙(3-(9H-咔唑-9-基)苯基)吡啶、三苯基(4-(9-苯基-9H-芴-9-基)苯基)矽烷、9,9-二甲基-N,N-二苯基-7-(4-(1-苯基-1H-苯並[d]咪唑-2-基)苯基)-9H-芴-2-胺、3,5-雙(3-(9H-咔唑-9-基)苯基)吡啶、9,9-螺聯芴-2-基-二苯基-膦氧化物、9,9'-(5-(三苯基矽基)-1,3-伸苯基)雙(9H-咔唑)、3-(2,7-雙(二苯基磷醯基)-9-苯基-9H-芴-9-基)-9-苯基-9H-咔唑、4,4,8,8,12,12-六(p-甲苯基)-4H-8H-12H-12C-氮雜二苯並[cd,mn]芘、4,7-二(9H-咔唑-9-基)-1,10-菲咯啉、2,2'-雙(4-(咔唑-9-基)苯基)聯苯基、2,8-雙(二苯基磷醯基)二苯並[b,d]噻吩、雙(2-甲基苯基)二苯基矽烷、雙[3,5-二(9H-咔唑-9-基)苯基]二苯基矽烷、3,6-雙(咔唑-9-基)-9-(2-乙基-己基)-9H-咔唑、3-(二苯基磷醯基)-9-(4-(二苯基磷醯基)苯基)-9H-咔唑、3,6-雙[(3,5-二苯基)苯基]-9-苯基咔唑等,藉由與發光性摻合物之共蒸鍍,可形成發光層。
作為發光性摻合物,可舉出3-(2-苯並噻唑基)-7-(二乙基胺基)香豆素、2,3,6,7-四氫-1,1,7,7-四甲基-1H,5H,11H-10-(2-苯並噻唑基)喹嗪並[9,9a,1gh]香豆素、喹吖啶酮、N,N'-二甲基-喹吖啶酮、參(2-苯基吡啶)銥(III)(Ir(ppy)3
)、雙(2-苯基吡啶)(乙醯丙酮酸鹽)銥(III)(Ir(ppy)2
(acac))、參[2-(p-甲苯基)吡啶]銥(III)(Ir(mppy)3
)、9,10-雙[N,N-二(p-甲苯基)胺基]蒽、9,10-雙[苯基(m-甲苯基)胺基]蒽、雙[2-(2-羥基苯基)苯並噻唑根]鋅(II)、N10
,N10
,N10'
,N10'
-四(p-甲苯基)-9,9'-聯蒽-10,10'-二胺、N10
,N10
,N10'
,N10'
-四苯基-9,9'-聯蒽-10,10'-二胺、N10
,N10'
-二苯基-N10
,N10'
-二萘基-9,9'-聯蒽-10,10'-二胺、4,4'-雙(9-乙基-3-咔唑並乙烯基)-1,1'-聯苯基、苝、2,5,8,11-四-t-丁基苝、1,4-雙[2-(3-N-乙基咔唑基)乙烯基]苯、4,4'-雙[4-(二-p-甲苯基胺基)苯乙烯]聯苯基、4-(二-p-甲苯基胺基)-4'-[(二-p-甲苯基胺基)苯乙烯]芪、雙[3,5-二氟-2-(2-吡啶基)苯基-(2-羧基吡啶基)]銥(III)、4,4'-雙[4-(二苯基胺基)苯乙烯]聯苯基、雙(2,4-二氟苯基Imidazorato)肆(1-吡唑基)硼酸鹽銥(III)、N,N'-雙(萘-2-基)-N,N'-雙(苯基)-參(9,9-二甲基芴)、2,7-雙{2-[苯基(m-甲苯基)胺基]-9,9-二甲基-芴-7-基}-9,9-二甲基-芴、N-(4-((E)-2-(6((E)-4-(二苯基胺基)苯乙烯)萘-2-基)乙烯基)苯基)-N-苯基苯胺、fac-銥(III)參(1-苯基-3-甲基苯並咪唑啉-2-亞基-C,C2'
)、mer-銥(III)參(1-苯基-3-甲基苯並咪唑啉-2-亞基-C,C2'
)、2,7-雙[4-(二苯基胺基)苯乙烯]-9,9-螺聯芴、6-甲基-2-(4-(9-(4-(6-甲基苯並[d]噻唑-2-基)苯基)蒽-10-基)苯基)苯並[d]噻唑、1,4-二[4-(N,N-二苯基)胺基]苯乙烯苯、1,4-雙(4-(9H-咔唑-9-基)苯乙烯)苯、(E)-6-(4-(二苯基胺基)苯乙烯)-N,N-二苯基萘-2-胺、雙(2,4-二氟苯基Imidazorato)(5-(吡啶-2-基)-1H-四唑)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑)((2,4-二氟苯甲基)二苯基膦酸鹽(Phosphinate))銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑鹽)(苯甲基二苯基膦酸鹽(Phosphinate))銥(III)、雙(1-(2,4-二氟苯甲基)-3-甲基苯並咪唑鎓)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑鹽)(4',6'-二氟苯基吡啶鹽)銥(III)、雙(4',6'-二氟苯基Imidazorato)(3,5-雙(三氟甲基)-2-(2'-吡啶基)吡咯鹽)銥(III)、雙(4',6'-二氟苯基Imidazorato)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)銥(III)、(Z)-6-三甲苯基-N-(6-三甲苯基喹啉-2(1H)-亞基)喹啉-2-胺-BF2
、(E)-2-(2-(4-(二甲基胺基)苯乙烯)-6-甲基-4H-吡喃-4-亞基)丙二腈、4-(二氰基伸甲基)-2-甲基-6-久洛尼定基(Julolidyl)-9-烯基-4H-吡喃、4-(二氰基伸甲基)-2-甲基-6-(1,1,7,7-四甲基久洛尼定基(Julolidyl)-9-烯基)-4H-吡喃、4-(二氰基伸甲基)-2-t-丁基-6-(1,1,7,7-四甲基久洛尼定(Julolidine)-4-基-乙烯基)-4H-吡喃、參(二苯甲醯基甲烷)菲咯啉銪(III)、5,6,11,12-四苯基萘並萘、雙(2-苯並[b]噻吩-2-基-吡啶)(乙醯丙酮酸鹽)銥(III)、參(1-苯基異喹啉)銥(III)、雙(1-苯基異喹啉)(乙醯丙酮酸鹽)銥(III)、雙[1-(9,9-二甲基-9H-芴-2-基)-異喹啉](乙醯丙酮酸鹽)銥(III)、雙[2-(9,9-二甲基-9H-芴-2-基)喹啉](乙醯丙酮酸鹽)銥(III)、參[4,4'-二-t-丁基-(2,2')-聯吡啶]釕(III)・雙(六氟磷酸酯)、參(2-苯基喹啉)銥(III)、雙(2-苯基喹啉)(乙醯丙酮酸鹽)銥(III)、2,8-二-t-丁基-5,11-雙(4-t-丁基苯基)-6,12-二苯基四苯、雙(2-苯基苯並噻唑根)(乙醯丙酮酸鹽)銥(III)、5,10,15,20-四苯基四苯並卟啉鉑、鋨(II)雙(3-三氟甲基-5-(2-吡啶)-吡唑鹽)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-三唑)二苯基甲基膦、鋨(II)雙(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-三唑)二甲基苯基膦、雙[2-(4-n-己基苯基)喹啉](乙醯丙酮酸鹽)銥(III)、參[2-(4-n-己基苯基)喹啉]銥(III)、參[2-苯基-4-甲基喹啉]銥(III)、雙(2-苯基喹啉)(2-(3-甲基苯基)吡啶鹽)銥(III)、雙(2-(9,9-二乙基-芴-2-基)-1-苯基-1H-苯並[d]咪唑根(imidazolato))(乙醯丙酮酸鹽)銥(III)、雙(2-苯基吡啶)(3-(吡啶-2-基)-2H-色烯-2-酮酸)銥(III)、雙(2-苯基喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮酸)銥(III)、雙(苯基異喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮酸)銥(III)、銥(III)雙(4-苯基噻吩並[3,2-c]Imidazorato-N,C2'
)乙醯丙酮酸鹽、(E)-2-(2-t-丁基-6-(2-(2,6,6-三甲基-2,4,5,6-四氫-1H-吡咯並[3,2,1-ij]喹啉-8-基)乙烯基)-4H-吡喃-4-亞基)丙二腈、雙(3-三氟甲基-5-(1-異喹啉基)吡唑鹽)(甲基二苯基膦)釕、雙[(4-n-己基苯基)異喹啉](乙醯丙酮酸鹽)銥(III)、鉑(II)八乙基卟吩(Porphin)、雙(2-甲基二苯並[f,h]喹喔啉)(乙醯丙酮酸鹽)銥(III)、參[(4-n-己基苯基)Quisoquinoline]銥(III)等。
作為形成電子輸送層之材料,可舉出8-羥基羥基喹啉根(quinolinolato)-鋰、2,2',2”-(1,3,5-石油醚(Benzine)甲苯基)-參(1-苯基-1-H-苯並咪唑)、2-(4-聯苯基)5-(4-t-丁基苯基)-1,3,4-噁二唑、2,9-二甲基-4,7-二苯基-1,10-菲咯啉、4,7-二苯基-1,10-菲咯啉、雙(2-甲基-8-羥基喹啉根(quinolinolato))-4-(苯基苯酚根)鋁、1,3-雙[2-(2,2'-聯吡啶-6-基)-1,3,4-噁二唑-5-基]苯、6,6'-雙[5-(聯苯基-4-基)-1,3,4-噁二唑-2-基]-2,2'-聯吡啶、3-(4-聯苯基)-4-苯基-5-t-丁基苯基-1,2,4-三唑、4-(萘-1-基)-3,5-二苯基-4H-1,2,4-三唑、2,9-雙(萘-2-基)-4,7-二苯基-1,10-菲咯啉、2,7-雙[2-(2,2'-聯吡啶-6-基)-1,3,4-噁二唑-5-基]-9,9-二甲基芴、1,3-雙[2-(4-t-丁基苯基)-1,3,4-噁二唑-5-基]苯、參(2,4,6-三甲基-3-(吡啶-3-基)苯基)硼烷、1-甲基-2-(4-(萘-2-基)苯基)-1H-咪唑並[4,5f][1,10]菲咯啉、2-(萘-2-基)-4,7-二苯基-1,10-菲咯啉、苯基-二芘基氧化膦、3,3',5,5'-四[(m-吡啶基)-苯-3-基]聯苯基、1,3,5-參[(3-吡啶基)-苯-3-基]苯、4,4'-雙(4,6-二苯基-1,3,5-三嗪-2-基)聯苯基、1,3-雙[3,5-二(吡啶-3-基)苯基]苯、雙(10-羥基苯並[h]喹啉根)鈹、二苯基雙(4-(吡啶-3-基)苯基)矽烷、3,5-二(芘-1-基)吡啶等。
作為形成電子注入層之材料,可舉出氧化鋰(Li2
O)、氧化鎂(MgO)、氧化鋁(Al2
O3
)、氟化鋰(LiF)、氟化鈉(NaF)、氟化鎂(MgF2
)、氟化銫(CsF)、氟化鍶(SrF2
)、三酸化鉬(MoO3
)、鋁、Li(acac)、乙酸鋰、安息香酸鋰等。 作為陰極材料,可舉出鋁、鎂-銀合金、鋁-鋰合金、鋰、鈉、鉀、銫等。
又,具有經由本發明之電荷輸送性塗料所得之薄膜所成的電洞注入層之有機EL元件的製作方法以外的其他例子,如以下所示。 對於上述EL元件製作,取代進行電洞輸送層、發光層、電子輸送層、電子注入層之真空蒸鍍操作,藉由依序形成電洞輸送層(以下為電洞輸送性高分子層)、發光層(以下為發光性高分子層),可製造出具有藉由本發明之電荷輸送性塗料所形成的電荷輸送性薄膜之有機EL元件。 具體而言,於陽極基板上塗布本發明之電荷輸送性塗料而藉由上述方法製作出電洞注入層,於該上面依序形成電洞輸送性高分子層、發光性高分子層,再蒸鍍陰極電極成為有機EL元件。
作為使用的陰極及陽極材料,可使用與上述相同者,亦可進行相同洗淨處理、表面處理。 作為電洞輸送性高分子層及發光性高分子層之形成法,於電洞輸送性高分子材料或者發光性高分子材料,或於此等加入摻合物之材料中加入溶劑並溶解,或均勻地分散,塗布於電洞注入層或電洞輸送性高分子層上面後,經過各燒成而成膜之方法可舉出。
作為電洞輸送性高分子材料,可舉出聚[(9,9-二己基芴基-2,7-二基)-co-(N,N'-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[(9,9-二辛基芴基-2,7-二基)-co-(N,N'-雙{p-丁基苯基}-1,1'-亞聯苯-4,4-二胺)]、聚[(9,9-雙{1'-戊烯-5'-基}芴基-2,7-二基)-co-(N,N'-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[N,N'-雙(4-丁基苯基)-N,N'-雙(苯基)-聯苯胺]-倍半矽氧烷封端、聚[(9,9-二辛基芴基-2,7-二基)-co-(4,4'-(N-(p-丁基苯基))二苯基胺)]等。
作為發光性高分子材料,可舉出聚(9,9-二烷基芴)(PDAF)等聚芴衍生物、聚(2-甲氧基-5-(2'-乙基己氧基)-1,4-伸苯基伸乙烯)(MEH-PPV)等聚伸苯基伸乙烯衍生物、聚(3-烷基噻吩)(PAT)等聚噻吩衍生物、聚乙烯咔唑(PVCz)等。
作為溶劑,可舉出甲苯、二甲苯、氯仿等,作為溶解或均勻分散法,可舉出攪拌、加熱攪拌、超音波分散等方法。 作為塗布方法,並無特別限定,可舉出噴墨法、噴霧法、浸漬法、旋轉塗布法、轉印印刷法、輥塗布法、刷毛塗布等。且,塗布可在氮、氬等惰性氣體下進行為佳。 作為燒成方法,可舉出在惰性氣體下或真空中、烤箱或加熱板進行加熱之方法。
具有經由本發明之電荷輸送性塗料所得之薄膜所成的電洞輸送層之EL元件的製作方法之例子,如以下所示。 於陽極基板上形成電洞注入層。於該層上面,藉由上述方法塗布本發明之電荷輸送性塗料後燒成,製作出電洞輸送層。 於該電洞輸送層上面,將發光層、電子輸送層、電子注入層、陰極以此順序設置。發光層、電子輸送層及電子注入層之形成方法及具體例子可舉出與上述相同者。又,電洞注入層可配合所使用的材料之特性等,以蒸鍍法、塗布法(溼式製程)中任一種方式形成即可。
作為形成電洞注入層之材料,可舉出銅酞菁、氧化鈦酞菁、鉑酞菁、吡嗪並[2,3-f][1,10]菲咯啉-2,3-二甲腈、N,N,N',N'-肆(4-甲氧基苯基)聯苯胺、2,7-雙[N,N-雙(4-甲氧基-苯基)胺基]-9,9-螺聯芴、2,2'-雙[N,N-雙(4-甲氧基-苯基)胺基]-9,9-螺聯芴、N,N'-二苯基-N,N'-二[4-(N,N-二甲苯基胺基)苯基]聯苯胺、N,N'-二苯基-N,N'-二[4-(N,N-二苯基胺基)苯基]聯苯胺、N4
,N4'
-(聯苯基-4,4'-二基)雙(N4
,N4'
,N4'
-三苯基聯苯基-4,4'-二胺)N1
,N1'
-(聯苯基-4,4'-二基)雙(N1
-苯基-N4
,N4'
-二-m-甲苯基苯-1,4-二胺)、國際公開第2004/043117號、國際公開第2004/105446號、國際公開第2005/000832號、國際公開第2005/043962號、國際公開第2005/042621號、國際公開第2005/107335號、國際公開第2006/006459號、國際公開第2006/025342號、國際公開第2006/137473號、國際公開第2007/049631號、國際公開第2007/099808號、國際公開第2008/010474號、國際公開第2008/032617號、國際公開第2008/032616號、國際公開第2008/129947號、國際公開第2009/096352號、國際公開第2010/041701號、國際公開第2010/058777號、國際公開第2010/058776號、國際公開第2013/042623號、國際公開第2013/129249號、國際公開第2014/115865號、國際公開第2014/132917號、國際公開第2014/141998號及國際公開2014/132834號所記載的電荷輸送材料等。
作為形成陽極材料、發光層、發光性摻合物、電子輸送層及電子阻擋層之材料、陰極材料,可舉出與上述相同者。
具有經由本發明之電荷輸送性塗料所得之薄膜所成的電洞注入輸送層之有機EL元件的製作方法之例子如以下所示。 於陽極基板上形成電洞注入輸送層,於該電洞注入輸送層上面,依序設置發光層、電子輸送層、電子注入層、陰極。發光層、電子輸送層及電子注入層之形成方法及具體例子可舉出與上述相同者。
作為形成陽極材料、發光層、發光性摻合物、電子輸送層及電子阻擋層之材料、陰極材料,可舉出與上述相同者。
且,於電極及上述各層之間的任意間,視必要可設置孔阻擋層、電子阻擋層等。例如作為形成電子阻擋層之材料,可舉出參(苯基吡唑)銥等。
構成於陽極與陰極及這些間所形成之層的材料,會取決於是否製造具備底部發射結構、頂部發射結構中任一元件而相異,考慮此點下做適宜材料選擇。 通常在底部發射結構之元件中,於基板側使用透明陽極,對於自基板側取出光線而言,在頂部發射結構之元件,使用由金屬所成的反射陽極,自與基板為反方向的透明電極(陰極)側取出光線,例如對於陽極材料而言,在製造底部發射結構之元件時使用ITO等透明陽極,在製造頂部發射結構之元件時使用Al/Nd等反射陽極。
本發明之有機EL元件欲防止特性惡化,依據一定方法,視必要與捕水劑等同時密封即可。 [實施例]
以下舉出實施例及比較例,對本發明做更具體說明,但本發明並未限定於下述實施例者。且,使用的裝置如以下所示。 (1)1
H,19
F-NMR:JEOL(股)製 核磁共振裝置 AL-300 (2)基板洗淨:長州產業(股)製 基板洗淨裝置(減壓電漿方式) (3)塗料之塗布:三笠(股)製 旋轉塗布機MS-A100 (4)膜厚測定:(股)小坂研究所製 微細形狀測定機SurfcoderET-4000 (5)膜之表面觀察:Lasertec公司製 共焦點雷射顯微鏡 real time掃描型雷射顯微鏡 1LM21D (6)EL元件之製作:長州產業(股)製 多功能蒸鍍裝置系統C-E2L1G1-N (7)EL元件之亮度等測定:(股)EHC製 多頻道IVL測定裝置 (8)EL元件之壽命測定(亮度半衰期測定):(股)EHC製 有機EL亮度壽命評估系統PEL-105S
[1]氟化烷基磷酸鎓鹽之合成 [合成例1](4-苯基硫基苯基)二苯基硫鎓 參(五氟乙基)三氟磷酸鹽(P-1)之合成
上述式所示P-1為依據專利第5828679號公報之製造例9記載的方法合成。
[2]電荷輸送性塗料之調製 [實施例1-1] 依據國際公開第2015/050253號之製造例12記載的方法所合成之下述式所示T-1 343mg,與在合成例1所得之P-1 183mg之混合物中,加入3-苯氧基甲苯5g及4-甲氧基甲苯5g,在室溫下經攪拌使其溶解,將所得之溶液以孔徑0.2μm的注射器濾器進行過濾後得到電荷輸送性塗料。
[實施例1-2] 依據國際公開第2015/050253號之製造例23記載的方法所合成的下述式所示T-2 291mg與在合成例1所得之P-1 130mg之混合物中,加入3-苯氧基甲苯4g及4-甲氧基甲苯4g,在室溫下攪拌並使其溶解,將所得之溶液以孔徑0.2μm的注射器濾器進行過濾後得到電荷輸送性塗料。
[實施例1-3] 於上述T-1 129mg、上述T-2 154mg與在合成例1所合成之P-1 138mg之混合物中,加入3-苯氧基甲苯4g及4-甲氧基甲苯4g,在室溫下攪拌並使其溶解,將所得之溶液以孔徑0.2μm的注射器濾器進行過濾後得到電荷輸送性塗料。
[3]有機EL元件之製作及特性評估 [實施例2-1] 將在實施例1-1所得之塗料,使用旋轉塗布機塗布於ITO基板後,在大氣環境下於200℃進行10分鐘燒成,於ITO基板上形成50nm之均勻薄膜。作為ITO基板,使用銦錫酸化物(ITO)於表面上以膜厚150nm製圖之25mm×25mm×0.7t的玻璃基板,於使用前藉由O2
電漿洗淨裝置(150W,30秒)除去表面上之雜質。 其次,對於形成薄膜之ITO基板,使用蒸鍍裝置(真空度1.0×10-5
Pa),將α-NPD(N,N’-二(1-萘)-N,N’-二苯基聯苯胺)以0.2nm/秒成形為30nm膜。其次,將CBP與Ir(PPy)3
共蒸鍍。共蒸鍍為控制其蒸鍍速度至Ir(PPy)3
的濃度成為6%,層合40nm。其次,依據層合BAlq、氟化鋰及鋁之薄膜,得到有機EL元件。此時,蒸鍍速度在對於BAlq及鋁為0.2nm/秒,對於氟化鋰各以0.02nm/秒的條件下進行,膜厚各為20nm、0.5nm及80nm。 且,欲防止空氣中之氧氣、水等影響所造成的特性劣化,有機EL元件藉由密封基板進行密封後,評估該特性。密封以以下程序進行。在氧濃度2ppm以下,露點-85℃以下的氮氣環境中,將有機EL元件收納於密封基板之間,將密封基板藉由接著劑((股)MORESCO製、Moresco Moisture Cut WB90US(P))貼合。此時,將捕水劑(Dynic(股)製、HD-071010W-40)與有機EL元件共同收納於密封基板內。對於貼合的密封基板,經UV光照射(波長:365nm、照射量:6,000mJ/cm2
)後,在80℃進行1小時的熱處理(annealing)後使接著材硬化。
[實施例2-2] 取代在實施例1-1所得之電荷輸送性塗料,使用在實施例1-2所得之電荷輸送性塗料以外,與實施例2-1同様方法下製作出有機EL元件。
[實施例2-3] 取代在實施例1-1所得之電荷輸送性塗料,使用在實施例1-3所得之電荷輸送性塗料以外,與實施例2-1同様方法下製作出有機EL元件。
評估實施例2-1~2-3之元件的特性。將元件在5,000cd/m2
發光時的驅動電壓、電流密度、電流效率、發光效率、外部發光量子產率(EQE)如表19所示。元件的亮度之半衰期(初期亮度5,000cd/m2
)如表20所示。
如表19及20所示,具備本發明之電荷輸送性薄膜的EL元件具有較佳驅動性。又壽命特性亦優良。
Claims (6)
- 一種電荷輸送性塗料,其特徵為含有電荷輸送性物質、氟化烷基磷酸鎓鹽與有機溶劑,其中前述氟化烷基磷酸鎓鹽為含有由式(a1)所示負離子與對陽離子所成的氟化烷基磷酸鎓鹽,前述電荷輸送性物質為含有式(1)或(2)所示苯胺衍生物;
- 如請求項1或2之電荷輸送性塗料,其中上述R3~R6、R7~R27、R30~R51及R53~R154為氫原子。
- 一種電荷輸送性薄膜,其特徵係由如請求項1~3中任1項之電荷輸送性塗料所得者。
- 一種有機電致發光元件,其特徵為具有如請求項4之電荷輸送性薄膜。
- 一種電荷輸送性薄膜之製造方法,其特徵為將如請求項1~3中任1項之電荷輸送性塗料塗布於基材上,使溶劑蒸發者。
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Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW201141991A (en) * | 2010-04-22 | 2011-12-01 | Hitachi Chemical Co Ltd | Organic electrical material, polymerization initiazor, ink composition, organic film and fabricating method thereof, organic electrical device, orgainc electroluminescence device, illuminating device and illuminating apparatus |
Family Cites Families (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5828679B2 (ja) | 1979-04-25 | 1983-06-17 | 富士通株式会社 | 半導体記憶装置の書込み回路 |
US9172048B2 (en) | 2002-11-07 | 2015-10-27 | Nissan Chemical Industries, Ltd. | Charge-transporting varnish |
TW200502277A (en) | 2003-05-20 | 2005-01-16 | Nissan Chemical Ind Ltd | Charge-transporting varnish |
WO2005000832A1 (ja) | 2003-06-25 | 2005-01-06 | Nissan Chemical Industries, Ltd. | 1,4-ベンゾジオキサンスルホン酸化合物及び電子受容性物質としての利用 |
TW200517469A (en) | 2003-10-30 | 2005-06-01 | Nissan Chemical Ind Ltd | Charge-transporting compound, charge-transporting material, charge-transporting varnish, charge-transporting thin film, and organic electroluminescent device |
US7795452B2 (en) | 2003-10-31 | 2010-09-14 | Nissan Chemical Industries, Ltd. | Charge-transporting organic material containing compound having 1,4-dithiin ring |
KR100611226B1 (ko) * | 2003-11-25 | 2006-08-09 | 삼성에스디아이 주식회사 | 유기 전계 발광 표시 장치 |
JP4662073B2 (ja) | 2004-04-30 | 2011-03-30 | 日産化学工業株式会社 | 良溶媒及び貧溶媒を含有するワニス |
WO2006006459A1 (ja) | 2004-07-09 | 2006-01-19 | Nissan Chemical Industries, Ltd. | オリゴアニリン化合物の精製方法およびオリゴアニリン化合物 |
EP1785413B1 (en) | 2004-08-31 | 2014-01-22 | Nissan Chemical Industries, Ltd. | Arylsulfonic acid compound and use thereof as electron-acceptor material |
JPWO2006137473A1 (ja) | 2005-06-24 | 2009-01-22 | 日産化学工業株式会社 | 芳香族スルホン酸化合物の製造法 |
US9172043B2 (en) | 2005-10-28 | 2015-10-27 | Nissan Chemical Industries, Ltd. | Charge-transporting varnish for spray or ink jet application |
JP5136795B2 (ja) | 2006-02-23 | 2013-02-06 | 日産化学工業株式会社 | スルホン酸エステル化合物からなる電子受容性物質前駆体およびその利用 |
WO2008010474A1 (fr) | 2006-07-18 | 2008-01-24 | Nissan Chemical Industries, Ltd. | Vernis contenant des charges |
KR101473294B1 (ko) | 2006-09-13 | 2014-12-16 | 닛산 가가쿠 고교 가부시키 가이샤 | 올리고아닐린 화합물 및 그 이용 |
KR101493435B1 (ko) | 2006-09-13 | 2015-02-13 | 닛산 가가쿠 고교 가부시키 가이샤 | 올리고아닐린 화합물 |
WO2008129947A1 (ja) | 2007-04-12 | 2008-10-30 | Nissan Chemical Industries, Ltd. | オリゴアニリン化合物 |
TWI447099B (zh) | 2008-01-29 | 2014-08-01 | Nissan Chemical Ind Ltd | Aryl sulfonic acid compounds and the use of electron acceptables |
KR101609595B1 (ko) | 2008-10-09 | 2016-04-06 | 닛산 가가쿠 고교 가부시키 가이샤 | 전하수송성 바니시 |
KR20170090515A (ko) | 2008-11-19 | 2017-08-07 | 닛산 가가쿠 고교 가부시키 가이샤 | 전하수송성 재료 및 전하수송성 바니시 |
JP5488473B2 (ja) | 2008-11-19 | 2014-05-14 | 日産化学工業株式会社 | 電荷輸送性ワニス |
TWI498350B (zh) * | 2009-10-01 | 2015-09-01 | Hitachi Chemical Co Ltd | 有機電子用材料、有機電子元件、有機電激發光元件、及使用其之顯示元件、照明裝置、顯示裝置 |
JP5828679B2 (ja) | 2011-05-31 | 2015-12-09 | サンアプロ株式会社 | フッ素化アルキルリン酸オニウム塩系酸発生剤 |
JP5879795B2 (ja) | 2011-07-26 | 2016-03-08 | 日立化成株式会社 | 有機エレクトロニクス材料、インク組成物、有機薄膜及びその製造方法、有機エレクトロニクス素子、有機エレクトロルミネセンス素子、表示素子、照明装置、並びに表示装置 |
US9444052B2 (en) | 2011-09-21 | 2016-09-13 | Nissan Chemical Industries, Ltd. | Charge-transporting varnish |
JP6426468B2 (ja) | 2012-03-02 | 2018-11-21 | 日産化学株式会社 | 電荷輸送性ワニス |
JP6221230B2 (ja) * | 2012-12-26 | 2017-11-01 | 日立化成株式会社 | 有機エレクトロニクス素子及びその製造方法 |
WO2014115865A1 (ja) | 2013-01-28 | 2014-07-31 | 日産化学工業株式会社 | 電荷輸送性ワニス |
EP2963699A4 (en) | 2013-02-26 | 2016-08-10 | Nissan Chemical Ind Ltd | CARGO TRANSPORT PAINT |
JP6015844B2 (ja) | 2013-02-28 | 2016-10-26 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2014141998A1 (ja) | 2013-03-11 | 2014-09-18 | 日産化学工業株式会社 | 電荷輸送性ワニス |
JP6181958B2 (ja) * | 2013-03-28 | 2017-08-16 | 日東電工株式会社 | 帯電防止性粘着シート、及び、光学フィルム |
JP2014205624A (ja) | 2013-04-11 | 2014-10-30 | サンアプロ株式会社 | オニウムボレート塩系酸発生剤 |
KR20160021181A (ko) * | 2013-06-18 | 2016-02-24 | 닛산 가가쿠 고교 가부시키 가이샤 | 싸이오펜 유도체와 그 이용 및 싸이오펜 유도체의 제조 방법 |
WO2015050253A1 (ja) | 2013-10-04 | 2015-04-09 | 日産化学工業株式会社 | アニリン誘導体およびその利用 |
CN105431424B (zh) * | 2013-12-18 | 2019-09-06 | 出光兴产株式会社 | 化合物、有机电致发光元件用材料、油墨组合物、有机电致发光元件、电子机器及制造方法 |
WO2017033771A1 (ja) * | 2015-08-21 | 2017-03-02 | シャープ株式会社 | 発光デバイス、表示装置、照明装置、電子機器 |
-
2018
- 2018-04-02 CN CN201880021842.1A patent/CN110476265A/zh active Pending
- 2018-04-02 EP EP18781940.4A patent/EP3608983A4/en not_active Withdrawn
- 2018-04-02 JP JP2019511226A patent/JP7163907B2/ja active Active
- 2018-04-02 KR KR1020197032442A patent/KR102579661B1/ko active IP Right Grant
- 2018-04-02 US US16/500,980 patent/US20200032140A1/en not_active Abandoned
- 2018-04-02 WO PCT/JP2018/014084 patent/WO2018186340A1/ja unknown
- 2018-04-03 TW TW107111837A patent/TWI811213B/zh active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW201141991A (en) * | 2010-04-22 | 2011-12-01 | Hitachi Chemical Co Ltd | Organic electrical material, polymerization initiazor, ink composition, organic film and fabricating method thereof, organic electrical device, orgainc electroluminescence device, illuminating device and illuminating apparatus |
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