JP6432593B2 - 電荷輸送性ワニス - Google Patents
電荷輸送性ワニス Download PDFInfo
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- JP6432593B2 JP6432593B2 JP2016504082A JP2016504082A JP6432593B2 JP 6432593 B2 JP6432593 B2 JP 6432593B2 JP 2016504082 A JP2016504082 A JP 2016504082A JP 2016504082 A JP2016504082 A JP 2016504082A JP 6432593 B2 JP6432593 B2 JP 6432593B2
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- 230000000052 comparative effect Effects 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 13
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- 235000013772 propylene glycol Nutrition 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- 238000000576 coating method Methods 0.000 description 10
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- 239000003446 ligand Substances 0.000 description 9
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
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- 229910052751 metal Inorganic materials 0.000 description 8
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- 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 7
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
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- 238000003786 synthesis reaction Methods 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000010405 anode material Substances 0.000 description 6
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
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- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 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 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- 125000003172 aldehyde group Chemical group 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
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- 125000002843 carboxylic acid group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 5
- 239000010955 niobium Substances 0.000 description 5
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
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- 0 C*(C)c1ccc(C(C)(C)Nc2cccc3c2ccc2ccccc32)cc1 Chemical compound C*(C)c1ccc(C(C)(C)Nc2cccc3c2ccc2ccccc32)cc1 0.000 description 4
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
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- 238000010304 firing Methods 0.000 description 4
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- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 3
- NMNQVRIUUBFICK-UHFFFAOYSA-N 9-benzyl-3-bromocarbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC1=CC=CC=C1 NMNQVRIUUBFICK-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 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
- 238000009835 boiling Methods 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 3
- 235000019437 butane-1,3-diol Nutrition 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
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- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
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- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
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- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000011964 heteropoly acid Substances 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
- C08G73/0266—Polyanilines or derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/52—Electrically conductive inks
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D165/00—Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Coating compositions based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/02—Polyamines
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Description
1.電荷輸送性物質及び有機溶媒を含む電荷輸送性ワニスであって、
上記有機溶媒が、良溶媒としてN,N−ジメチルイソブチルアミドを含むことを特徴とする電荷輸送性ワニス。
2.上記有機溶媒中、N,N−ジメチルイソブチルアミドが35質量%以上含まれる1の電荷輸送性ワニス。
3.電荷輸送性物質が、アニリン誘導体及びチオフェン誘導体から選ばれる少なくとも1種を含む1又は2の電荷輸送性ワニス。
4.更に、ドーパントを含む1〜3のいずれかの電荷輸送性ワニス。
5.1〜4のいずれかの電荷輸送性ワニスを用いて作製される電荷輸送性薄膜。
6.5の電荷輸送性薄膜を有する有機EL素子。
7.1〜4のいずれかの電荷輸送性ワニスを用いることを特徴とする電荷輸送性薄膜の製造方法。
8.5の電荷輸送性薄膜を用いることを特徴とする有機EL素子の製造方法。
9.電荷輸送性物質及び有機溶媒を含む電荷輸送性ワニスから作製される電荷輸送性薄膜の平坦化方法であって、
上記有機溶媒として、N,N−ジメチルイソブチルアミドを用いることを特徴とする平坦化方法。
N−メチルホルムアミド、N,N−ジメチルホルムアミド、N,N−ジエチルホルムアミド、N−メチルアセトアミド、N,N−ジメチルアセトアミド、N−メチルプロピオンアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等のアミド類;
ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、ジプロピレングリコール、1,2−エタンジオール(エチレングリコール)、1,2−プロパンジオール(プロピレングリコール)、1,2−ブタンジオール、2,3−ブタンジオール、1,3−ブタンジオール、1,4−ブタンジオール、1,5−ペンタンジオール、2−メチル−2,4−ペンタンジオール(ヘキシレングリコール)、1,3−オクチレングリコール、3,6−オクチレングリコール等のグリコール類;
グリセリン等のトリオール類;
エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノイソプロピルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールモノイソブチルエーテル、エチレングリコールモノヘキシルエーテル等のエチレングリコールモノアルキルエーテル類、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノイソプロピルエーテル、プロピレングリコールモノブチルエーテル、プロピレングリコールモノイソブチルエーテル、プロピレングリコールモノヘキシルエーテル等のプロピレングリコールモノアルキルエーテル類等のアルキレングリコールモノアルキルエーテル類;
エチレングリコールモノフェニルエーテル等のエチレングリコールモノアリールエーテル類、プロピレングリコールモノフェニルエーテル等のプロピレングリコールモノアリールエーテル類等のアルキレングリコールモノアリールエーテル類;
エチレングリコールモノベンジルエーテル等のエチレングリコールモノアラルキルエーテル類、プロピレングリコールモノベンジルエーテル等のプロピレングリコールモノアラルキルエーテル類等のアルキレングリコールモノアラルキルエーテル類;
エチレングリコールブトキシエチルエーテル等のエチレングリコールアルコキシアルキルエーテル類、プロピレングリコールブトキシエチルエーテル等のプロピレングリコールアルコキシアルキルエーテル類等のアルキレングリコールアルコキシアルキルエーテル類;
エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、エチレングリコールジプロピルエーテル、エチレングリコールジイソプロピルエーテル、エチレングリコールジブチルエーテル等のエチレングリコールジアルキルエーテル類、プロピレングリコールジメチルエーテル、プロピレングリコールジエチルエーテル、プロピレングリコールジプロピルエーテル、プロピレングリコールジイソプロピルエーテル、プロピレングリコールジブチルエーテル等のプロピレングリコールジアルキルエーテル類等のアルキレングリコールジアルキルエーテル類;
エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノプロピルエーテルアセテート、エチレングリコールモノイソプロピルエーテルアセテート、エチレングリコールモノブチルエーテルアセテート等のエチレングリコールモノアルキルエーテルアセテート類、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノプロピルエーテルアセテート、プロピレングリコールモノイソプロピルエーテルアセテート、プロピレングリコールモノブチルエーテルアセテート等のプロピレングリコールモノアルキルエーテルアセテート類等のアルキレングリコールモノアルキルエーテルアセテート類;
エチレングリコールモノアセテート等のエチレングリコールモノアセテート類、プロピレングリコールモノアセテート等のプロピレングリコールモノアセテート類等のアルキレングリコールモノアセテート類;
エチレングリコールジアセテート等のエチレングリコールジアセテート類、プロピレングリコールジアセテート等のプロピレングリコールジアセテート類等のアルキレングリコールジアセテート類;
ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノプロピルエーテル、ジエチレングリコールモノイソプロピルエーテル、ジエチレングリコールモノブチルエーテル、ジエチレングリコールモノイソブチルエーテル、ジエチレングリコールモノヘキシルエーテルのジエチレングリコールモノアルキルエーテル類、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノプロピルエーテル、ジプロピレングリコールモノイソプロピルエーテル、ジプロピレングリコールモノブチルエーテル、ジプロピレングリコールモノイソブチルエーテル、ジプロピレングリコールモノヘキシルエーテル等のジプロピレングリコールモノアルキルエーテル類等のジアルキレングリコールモノアルキルエーテル類;
ジエチレングリコールモノフェニルエーテル等のジエチレングリコールモノアリールエーテル類、ジプロピレングリコールモノフェニルエーテル等のジプロピレングリコールモノアリールエーテル類等のジアルキレングリコールモノアリールエーテル類;
ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールジプロピルエーテル、ジエチレングリコールジイソプロピルエーテル、ジエチレングリコールジブチルエーテル等のジエチレングリコールジアルキルエーテル類、ジプロピレングリコールジメチルエーテル、ジプロピレングリコールジエチルエーテル、ジプロピレングリコールジプロピルエーテル、ジプロピレングリコールジイソプロピルエーテル、ジプロピレングリコールジブチルエーテル等のジプロピレングリコールジアルキルエーテル類等のジアルキレングリコールジアルキルエーテル類;
ジエチレングリコールモノメチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノプロピルエーテルアセテート、ジエチレングリコールモノイソプロピルエーテルアセテート、ジエチレングリコールモノブチルエーテルアセテート、ジエチレングリコールモノイソブチルエーテルアセテート、ジエチレングリコールモノヘキシルエーテルアセテートのジエチレングリコールモノアルキルエーテルアセテート類、ジプロピレングリコールモノメチルエーテルアセテート、ジプロピレングリコールモノエチルエーテルアセテート、ジプロピレングリコールモノプロピルエーテルアセテート、ジプロピレングリコールモノイソプロピルエーテルアセテート、ジプロピレングリコールモノブチルエーテルアセテート、ジプロピレングリコールモノイソブチルエーテルアセテート、ジプロピレングリコールモノヘキシルエーテルアセテート等のジプロピレングリコールモノアルキルエーテルアセテート類等のジアルキレングリコールモノアルキルエーテルアセテート類;
トリエチレングリコールモノメチルエーテル、トリエチレングリコールモノエチルエーテル等のトリエチレングリコールモノアルキルエーテル類、トリプロピレングリコールモノメチルエーテル、トリプロピレングリコールモノエチルエーテル等のトリプロピレングリコールモノアルキルエーテル類等のトリアルキレングリコールモノアルキルエーテル類;
トリエチレングリコールジメチルエーテル、トリエチレングリコールジエチルエーテル等のトリエチレングリコールジアルキルエーテル類、トリプロピレングリコールジメチルエーテル、トリプロピレングリコールジエチルエーテル等のトリプロピレングリコールジアルキルエーテル類等のトリアルキレングリコールジアルキルエーテル類;
1−プロパノール、2−プロパノール、1−ブタノール、2−ブタノール、1−ペンタノール、1−ヘキサノール、1−ヘプタノール、1−ノナノール、1−デカノール、1−ウンデカノール、1−ドデカノール、1−テトラデカノール等の直鎖脂肪族アルコール類、シクロヘキサノール、2−メチルシクロヘキサノール等の環状脂肪族アルコール類等の脂肪族アルコール類;
フェノール等のフェノール類;
ベンジルアルコール等の芳香族アルコール類;
フルフリルアルコール等の複素環含有アルコール類;
テトラヒドロフルフリルアルコール等の水素化複素環含有アルコール類;
ジイソプロピルエーテル、ジ−n−ブチルエーテル、ジ−n−ヘキシルエーテル等のジアルキルエーテル類;
メチルフェニルエーテル、エチルフェニルエーテル、n−ブチルフェニルエーテル、ベンジル(3−メチルブチル)エーテル、(2−メチルフェニル)メチルエーテル、(3−メチルフェニル)メチルエーテル、(4−メチルフェニル)メチルエーテル等のアルキルアリールエーテル類;
エチルベンジルエーテル等のアルキルアラルキルエーテル類;
2−メチルフラン、テトラヒドロフラン、テトラヒドロピラン等の環状アルキルモノエーテル類;
1,4−ジオキサン等の環状アルキルジエーテル類;
トリオキサン等の環状アルキルトリエーテル類;
ジグリシジルエーテル等のジエポキシアルキルエーテル類;
エチルアセテート、n−プロピルアセテート、イソプロピルアセテート、n−ブチルアセテート、イソブチルアセテート、s−ブチルアセテート、t−ブチルアセテート、n−ペンチルアセテート、(3−メチルブチル)アセテート、n−ヘキシルアセテート、(2−エチルブチル)アセテート、(2−エチルヘキシル)アセテート等の直鎖状又は分岐状アルキルアセテート類、シクロヘキシルアセテート、2−メチルシクロヘキシルアセテート等の環状アルキルアセテート類等のアルキルアセテート類;エチルプロピオネート、n−プロピルプロピオネート、イソプロピルプロピオネート、n−ブチルプロピオネート、イソブチルプロピオネート、s−ブチルプロピオネート、t−ブチルプロピオネート、n−ペンチルプロピオネート、(3−メチルブチル)プロピオネート、n−ヘキシルプロピオネート、、(2−エチルブチル)プロピオネート、(2−エチルヘキシル)プロピオネート等の直鎖状又は分岐状アルキルプロピオネート類、シクロヘキシルプロピオネート、2−メチルシクロヘキシルプロピオネート等の環状アルキルプロピオネート類等のアルキルプロピオネート類;エチルブチレート、n−プロピルブチレート、イソプロピルブチレート、n−ブチルブチレート、イソブチルブチレート、s−ブチルブチレート、t−ブチルブチレート、n−ペンチルブチレート、(3−メチルブチル)ブチレート、n−ヘキシルブチレート、(2−エチルブチル)ブチレート、(2−エチルヘキシル)ブチレート等の直鎖状又は分岐状アルキルブチレート類、シクロヘキシルブチレート、2−メチルシクロヘキシルブチレート等の環状アルキルブチレート類等のアルキルブチレート類;エチルラクテート、n−プロピルラクテート、イソプロピルラクテート、n−ブチルラクテート、イソブチルラクテート、s−ブチルラクテート、t−ブチルラクテート、n−ペンチルラクテート、(3−メチルブチル)ラクテート、n−ヘキシルラクテート、(2−エチルブチル)ラクテート、(2−エチルヘキシル)ラクテート等の直鎖状又は分岐状アルキルラクテート類、シクロヘキシルラクテート、2−メチルシクロヘキシルラクテート等の環状アルキルラクテート類等のアルキルラクテート類等のアルキルエステル類;
ベンジルアセテート等のアラルキルアセテート類、ベンジルプロピオネート等のアラルキルプロピオネート類、ベンジルブチレート等のアラルキルブチレート類、ベンジルラクテート等のアラルキルラクテート類等のアラルキルアルキルエステル類;
ジエチルケトン、ジイソブチルケトン、メチルエチルケトン、メチルn−プロピルケトン、メチルn−ブチルケトン、メチルイソブチルケトン、メチルn−プロピルケトン、メチルn−ヘキシルケトン、エチルn−ブチルケトン、ジ−n−プロピルケトン等のジアルキルケトン類;
イソホロン等の環状アルケニルケトン類;
シクロヘキサノン等の環状アルキルケトン類;
4−ヒドロキシ−4−メチル−2−ペンタノン(ジアセトンアルコール)等のヒドロキシジアルキルケトン類;
フルフラール等の複素環含有アルデヒド類;
ヘプタン、オクタン、2,2,3−トリメチルヘキサン、デカン、ドデカン等の直鎖状又は分岐状アルカン類;
トルエン、キシレン、o−キシレン、m−キシレン、p−キシレン、メシチレン、テトラリン、シクロヘキシルベンゼン等のアルキルベンゼン類;
シクロヘキサン、メチルシクロヘキサン、エチルシクロヘキサン等の環状アルカン類
等が挙げられるが、これらに限定されない。これらの溶媒は、1種又は2種以上使用することができる。
本発明において、電荷輸送性物質としては、従来有機ELの分野等で用いられるものを用いることができる。その具体例としては、オリゴアニリン誘導体、N,N'−ジアリールベンジジン誘導体、N,N,N',N'−テトラアリールベンジジン誘導体等のアリールアミン誘導体(アニリン誘導体)、オリゴチオフェン誘導体、チエノチオフェン誘導体、チエノベンゾチオフェン誘導体等のチオフェン誘導体、オリゴピロール等のピロール誘導体等の各種電荷輸送性化合物が挙げられる。これらのうち、アリールアミン誘導体、チオフェン誘導体が好ましい。
銅、パラジウム等の上述の触媒を用いて、式(1−9)〜(1−14)で表されるアニリン誘導体又は式(3'−3)〜(3'−4)で表されるアミン化合物を製造する場合、触媒、配位子、溶媒、反応温度等に関する条件は、式(1)で表されるアニリン誘導体の製造方法について説明した上記条件を採用し得る。
反応終了後は、常法に従って後処理をして、式(14)又は(14')で表されるオリゴチオフェン誘導体を得ることができる。
本発明の電荷輸送性ワニスは、ドーパントを含んでもよい。ドーパントとしては、特に限定されないが、例えば、ヘテロポリ酸やアリールスルホン酸が好適である。
本発明の電荷輸送性ワニスを基材上に塗布して焼成することで、基材上に電荷輸送性薄膜を形成させることができる。
本発明の有機EL素子は、一対の電極を有し、これら電極の間に、上述の本発明の電荷輸送性薄膜を有するものである。
(a)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(b)陽極/正孔注入層/正孔輸送層/発光層/電子注入輸送層/陰極
(c)陽極/正孔注入輸送層/発光層/電子輸送層/電子注入層/陰極
(d)陽極/正孔注入輸送層/発光層/電子注入輸送層/陰極
(e)陽極/正孔注入層/正孔輸送層/発光層/陰極
(f)陽極/正孔注入輸送層/発光層/陰極
(1)1H-NMR:日本電子(株)製、JNM-ECP300 FT NMR SYSTEM
(2)MALDI-TOF-MS:ブルカー社製、autoflex III smartbeam
(3)基板洗浄:長州産業(株)製、基板洗浄装置(減圧プラズマ方式)
(4)ワニスの塗布:ミカサ(株)製、スピンコーターMS-A100
(5)膜厚測定:(株)小坂研究所製、微細形状測定機サーフコーダET-4000
(6)膜の表面観察:レーザーテック社製、リアルタイム走査型レーザー顕微鏡1LM21D
(7)EL素子の作製:長州産業(株)製、多機能蒸着装置システムC-E2L1G1-N
(8)EL素子の発光面の観察及び輝度等の測定:(有)テック・ワールド製、I-V-L測定システム
攪拌終了後、反応混合物を室温まで冷却し、冷却した反応混合物とトルエン200mLと飽和食塩水150mLとを混合して分液処理をした。得られた有機層に活性炭を0.5g加え、室温で1時間攪拌した。
その後、ろ過によって活性炭を取り除き、ろ液を濃縮した。濃縮液をメタノール及び酢酸エチルの混合溶媒(200mL/200mL)に滴下し、得られたスラリーを室温で1時間攪拌し、次いでスラリーをろ過してろ物を回収した。得られたろ物を乾燥し、目的とするN1,N1,N4−トリス(9−ベンジル−9H−カルバゾール−3−イル)−N4−(4−(ビス(9−ベンジル−9H−カルバゾール−3−イル)アミノ)フェニル)ベンゼン−1,4−ジアミンを得た(収量8.46g、収率80%)。1H-NMRの測定結果を以下に示す。
1H-NMR (300MHz, THF-d8) δ[ppm]: 7.91-8.00(m, 10H), 7.52-7.58(m, 10H), 7.34-7.39(m, 6H), 7.17-7.26(m, 29H), 7.03-7.11(m, 5H), 6.83(d, J=9.0Hz, 4H), 6.76(d, J=9.0Hz, 4H), 5.58(s, 10H).
攪拌終了後、反応混合物をイオン交換水120mL中に滴下し、そこへ5mol/L塩酸9mLを滴下し、得られたスラリーを室温で1時間攪拌した。そして、スラリーをろ過してろ物を回収した。得られたろ物とテトラヒドロフラン90mLとをよく混合し、その混合物をシリカゲルでろ過し、得られたろ液を濃縮した。濃縮液をメタノール150mL中に滴下し、得られたスラリーを室温で1時間攪拌した。
最後に、スラリーをろ過してろ物を回収し、得られたろ物を乾燥し、目的とするアニリン誘導体Aを得た(収量2.20g、収率90%)。MALDI-TOF-MSの測定結果を以下に示す。
MALDI-TOF-MS m/Z found: 1024.13 ([m]+calcd: 1024.40).
[2−1]
フラスコ内に、3−ブロモカルバゾール10.0g、水酸化ナトリウム1.75g、及びN,N−ジメチルホルムアミド100mLを入れた後、フラスコ内を窒素置換した。そこへ、ベンジルブロミド7.42gを滴下し、室温で19時間攪拌した後、反応混合物を攪拌したイオン交換水に滴下し、室温で更に攪拌した。得られたスラリーをろ過し、ろ物を乾燥し、目的とする9−ベンジル−3−ブロモカルバゾールを得た(収量13.1g、収率96%)。1H-NMRの測定結果を以下に示す。
1H-NMR (300MHz,CDCl3) δ[ppm]: 8.23(d, J=2.1Hz, 1H), 8.07(d, J=8.0Hz, 1H), 7.49(dd, J=8.6, 2.1Hz, 1H), 7.42-7.45(m, 1H), 7.36(d, J=8.0Hz, 1H), 7.21-7.31(m, 5H), 7.08-7.11(m, 2H), 5.49(s, 2H).
攪拌終了後、反応混合物を室温まで冷却し、冷却した反応混合物とトルエンと飽和食塩水とを混合して分液処理をした。得られた有機層へ活性炭を加えて室温で30分間攪拌し、次いで、ろ過によって活性炭を取り除き、ろ液を濃縮した。得られた濃縮液を、メタノール及び酢酸エチルの混合溶媒に滴下し、得られたスラリーを室温で攪拌した。
最後に、スラリーをろ過し、ろ物を乾燥して、目的とするN1,N4−ビス(9−ベンジル−9H−カルバゾール−3−イル)−N1−(4−((9−ベンジル−9H−カルバゾール−3−イル)(4−(ジフェニルアミノ)フェニル)アミノ)フェニル)−N4−(4−(ジフェニルアミノ)フェニル)ベンゼン−1,4−ジアミンを得た(収量3.92g、収率93%)。MALDI-TOF-MSの測定結果を以下に示す。
MALDI-TOF-MS m/Z found: 1451.52 ([m]+calcd: 1450.63).
攪拌終了後、反応混合物をイオン交換水及びメタノールの混合溶媒に滴下して得られた混合物を攪拌し、そこへ5mol/L塩酸5mLを滴下して更に攪拌した。
最後に、スラリーをろ過し、ろ物を乾燥して、目的とするアニリン誘導体Bを得た(収量1.62g、収率99%)。MALDI-TOF-MSの測定結果を以下に示す。
MALDI-TOF-MS m/Z found: 1180.10 ([m]+calcd: 1180.49).
攪拌終了後、反応混合物をイオン交換水に滴下し、得られたスラリーを室温で30分間攪拌した。次いで、スラリーをろ過し、ろ物を乾燥させ、得られた粉末をトルエンに溶解させて得られた溶液を用いて、シリカゲルカラムクロマトグラフィー(展開溶媒:トルエン)を行い、薄層クロマトグラフィー(TLC)法等により目的物の有無を確認することで目的物を含むフラクションを分取した。分取したフラクションから減圧下で溶媒を留去し、得られた固体を乾燥し、式(H5)で表されるアニリン誘導体を得た(収量0.37g、収率40%)。MALDI-TOF-MSの測定結果を以下に示す。
MALDI-TOF-MS m/Z found: 1890.54 ([m]+calcd:1889.34).
攪拌終了後、反応混合物をろ過し、得られたろ液から減圧下で溶媒を留去し、得られた残渣をトルエン及びn−ヘキサンの混合溶媒(3/2(v/v))に溶解させて得られた溶液を用いてシリカゲルカラムクロマトグラフィー(展開溶媒:トルエン/ヘキサン)を行い、薄層クロマトグラフィー(TLC)法等により目的物の有無を確認することで目的物を含むフラクションを分取した。
分取したフラクションから減圧下で溶媒を留去し、得られた固体を乾燥し、式(H6)で表されるアニリン誘導体を得た(収量1.34g、収率40%)。1H-NMR及びMALDI-TOF-MSの測定結果を以下に示す。
1H-NMR (300MHz,THF-d8) δ[ppm]: 8.02-8.10 (m,6H), 6.90-7.46(m, 51H).
MALDI-TOF-MS m/Z found: 1699.75 ([m]+calcd: 1700.46).
[実施例1−1]
電荷輸送性物質として下記式(H1)で表されるアニリン誘導体(以下、H1)0.067g及びドーパントとして下記式(D1)で表されるアリールスルホン酸化合物(以下、D1)0.137gを、N,N−ジメチルイソブチルアミド(DMIB)10gに溶解させて攪拌し、得られた溶液を孔径0.2μmのPTFE製フィルターを用いて濾過し、電荷輸送性ワニスを得た。
表19にしたがって、電荷輸送性物質、ドーパント及び溶媒の種類並びにこれらの使用量を変更した以外は、実施例1−1と同様の方法で電荷輸送性ワニスを調製した。
なお、表中、H2は、下記式(H2)で表されるアニリン誘導体(式中、Phは、フェニル基を表す。)を、H3は、N,N'−ジフェニルベンジジンを、H4は下記式(H4)で表されるチオフェン誘導体(式中、n−Hexは、n−ヘキシル基を表す。)を、D2はリンタングステン酸二無水物を、DPMはジプロピレングリコールモノメチルエーテルを、2,3−BDは2,3−ブタンジオールを、DMIは1,3−ジメチル−2−イミダゾリジノンを、DMAcはN,N−ジメチルアセトアミドを、それぞれ示す。
[実施例2−1]
実施例1−1で得られたワニスを、スピンコーターを用いてITO基板に塗布した後、大気下で、50℃で5分間仮焼成をし、次いで230℃で15分間本焼成をし、ITO基板上に30nmの薄膜を形成した。なお、ITO基板としては、ITOが表面上に膜厚150nmでパターニングされた25mm×25mm×0.7tのガラス基板を用い、使用前にO2プラズマ洗浄装置(150W、30秒間)によって表面上の不純物を除却した。
実施例1−1で得られたワニスの代わりに、実施例1−2〜1−16、比較例1−1〜1−10で得られたワニスを用いた以外は、実施例2−1と同様の方法で薄膜を形成した。
[実施例3−1]
実施例2−1と同様の方法で、ITO基板上に30nmの薄膜を形成した。
次いで、薄膜を形成したITO基板に対し、蒸着装置(真空度1.0×10-5Pa)を用いてα−NPD、Alq3、フッ化リチウム、及びアルミニウムの薄膜を順次積層し、有機EL素子を得た。この際、蒸着レートは、α−NPD、Alq3及びアルミニウムについては0.2nm/秒、フッ化リチウムについては0.02nm/秒の条件でそれぞれ行い、膜厚は、それぞれ30nm、40nm、0.5nm及び120nmとした。
なお、空気中の酸素、水等の影響による特性劣化を防止するため、有機EL素子は封止基板により封止した後、その特性を評価した。封止は、以下の手順で行った。酸素濃度2ppm以下、露点−85℃以下の窒素雰囲気中で、有機EL素子を封止基板の間に収め、封止基板を接着材(MORESCO(株)製WB90US(P))により貼り合わせた。この際、捕水剤(ダイニック(株)製HD-071010W-40)を有機EL素子と共に封止基板内に収めた。貼り合わせた封止基板に対し、UV光を照射(波長:365nm、照射量:6,000mJ/cm2)した後、80℃で1時間、アニーリング処理して接着材を硬化させた。
実施例1−1で得られたワニスの代わりに、それぞれ、実施例1−2及び比較例1−1〜1−4で得られたワニスを用いた以外は、実施例3−1と同様の方法で有機EL素子を作製した。
実施例1−6で得られたワニスを、スピンコーターを用いてITO基板に塗布した後、80℃で1分間乾燥し、更に、大気雰囲気下、150℃で10分間焼成し、ITO基板上に30nmの均一な薄膜を形成した。なお、ITO基板としては、実施例3−1と同様のものを用いた。
次いで、薄膜を形成したITO基板に対し、蒸着装置(真空度1.0×10-5Pa)を用いてα−NPDを0.2nm/秒にて30nm成膜した。次に、CBPとIr(PPy)3を共蒸着した。共蒸着はIr(PPy)3の濃度が6%になるように蒸着レートをコントロールし、40nm積層させた。次いで、BAlq、フッ化リチウム及びアルミニウムの薄膜を順次積層して有機EL素子を得た。この際、蒸着レートは、BAlq及びアルミニウムについては0.2nm/秒、フッ化リチウムについては0.02nm/秒の条件でそれぞれ行い、膜厚は、それぞれ20nm、0.5nm及び100nmとした。
なお、実施例3−1と同様の方法で素子を封止した後、その特性を評価した。
実施例1−6で得られたワニスの代わりに、実施例1−7で得られたワニスを用いた以外は、実施例3−3と同様の方法で有機EL素子を作製した。
Claims (9)
- 電荷輸送性物質及び有機溶媒を含む電荷輸送性ワニスであって、
上記有機溶媒が、良溶媒としてN,N−ジメチルイソブチルアミドを含むことを特徴とする電荷輸送性ワニス。 - 上記有機溶媒中、N,N−ジメチルイソブチルアミドが35質量%以上含まれる請求項1記載の電荷輸送性ワニス。
- 電荷輸送性物質が、アニリン誘導体及びチオフェン誘導体から選ばれる少なくとも1種を含む請求項1又は2記載の電荷輸送性ワニス。
- 更に、ドーパントを含む請求項1〜3のいずれか1項記載の電荷輸送性ワニス。
- 請求項1〜4のいずれか1項記載の電荷輸送性ワニスを用いて作製される電荷輸送性薄膜。
- 請求項5記載の電荷輸送性薄膜を有する有機エレクトロルミネッセンス素子。
- 請求項1〜4のいずれか1項記載の電荷輸送性ワニスを用いることを特徴とする電荷輸送性薄膜の製造方法。
- 請求項5記載の電荷輸送性薄膜を用いることを特徴とする有機エレクトロルミネッセンス素子の製造方法。
- 電荷輸送性物質及び有機溶媒を含む電荷輸送性ワニスから作製される電荷輸送性薄膜の平坦化方法であって、
上記有機溶媒として、N,N−ジメチルイソブチルアミドを用いることを特徴とする平坦化方法。
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CN106025098B (zh) * | 2011-09-21 | 2018-10-02 | 日产化学工业株式会社 | 电荷传输性清漆 |
JP6426468B2 (ja) * | 2012-03-02 | 2018-11-21 | 日産化学株式会社 | 電荷輸送性ワニス |
JP6311343B2 (ja) * | 2013-05-09 | 2018-04-18 | Jsr株式会社 | 液晶配向剤、液晶配向膜、液晶表示素子、液晶配向膜の製造方法、位相差フィルム及び位相差フィルムの製造方法 |
EP3053910B1 (en) * | 2013-10-04 | 2021-04-28 | Nissan Chemical Corporation | Aniline derivatives and uses thereof |
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WO2015125721A1 (ja) | 2015-08-27 |
KR20160123347A (ko) | 2016-10-25 |
CN106030843B (zh) | 2019-01-18 |
EP3109914A4 (en) | 2017-10-11 |
TW201546211A (zh) | 2015-12-16 |
TWI638869B (zh) | 2018-10-21 |
EP3109914A1 (en) | 2016-12-28 |
EP3109914B1 (en) | 2021-04-28 |
JPWO2015125721A1 (ja) | 2017-03-30 |
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