JP2017501263A - アクリル酸エステルおよび/またはメタクリル酸エステル単位を含むポリマーバインダーを含む組成物 - Google Patents
アクリル酸エステルおよび/またはメタクリル酸エステル単位を含むポリマーバインダーを含む組成物 Download PDFInfo
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- JP2017501263A JP2017501263A JP2016536834A JP2016536834A JP2017501263A JP 2017501263 A JP2017501263 A JP 2017501263A JP 2016536834 A JP2016536834 A JP 2016536834A JP 2016536834 A JP2016536834 A JP 2016536834A JP 2017501263 A JP2017501263 A JP 2017501263A
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- 239000000203 mixture Substances 0.000 title claims abstract description 80
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical group CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 title claims abstract description 6
- -1 acrylic ester Chemical class 0.000 title claims description 32
- 229920005596 polymer binder Polymers 0.000 title abstract description 7
- 239000002491 polymer binding agent Substances 0.000 title abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 93
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 48
- 229920000642 polymer Polymers 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 238000007639 printing Methods 0.000 claims description 23
- 239000003960 organic solvent Substances 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 239000003446 ligand Substances 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 150000008378 aryl ethers Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 230000009477 glass transition Effects 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
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- 229910004013 NO 2 Inorganic materials 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
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- 229910052794 bromium Inorganic materials 0.000 claims description 2
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- 125000005396 acrylic acid ester group Chemical group 0.000 claims 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000002635 aromatic organic solvent Substances 0.000 claims 1
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 11
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 10
- 239000004065 semiconductor Substances 0.000 description 10
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 9
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 9
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- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 8
- 150000004982 aromatic amines Chemical class 0.000 description 8
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
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- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
- 239000005020 polyethylene terephthalate Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 5
- 125000005504 styryl group Chemical group 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 150000001345 alkine derivatives Chemical class 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 238000009396 hybridization Methods 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 150000003384 small molecules Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical class C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920001774 Perfluoroether Polymers 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 125000004986 diarylamino group Chemical group 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- IYRWEQXVUNLMAY-UHFFFAOYSA-N fluoroketone group Chemical group FC(=O)F IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 3
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- 230000006872 improvement Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229940095102 methyl benzoate Drugs 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 150000003440 styrenes Chemical group 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- MEBONNVPKOBPEA-UHFFFAOYSA-N 1,1,2-trimethylcyclohexane Chemical compound CC1CCCCC1(C)C MEBONNVPKOBPEA-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- ZCJAYDKWZAWMPR-UHFFFAOYSA-N 1-chloro-2-fluorobenzene Chemical compound FC1=CC=CC=C1Cl ZCJAYDKWZAWMPR-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
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- 230000000996 additive effect Effects 0.000 description 2
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- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical compound C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
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- TUAHORSUHVUKBD-UHFFFAOYSA-N benzo[c]phenanthrene Chemical class C1=CC=CC2=C3C4=CC=CC=C4C=CC3=CC=C21 TUAHORSUHVUKBD-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
-
- 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
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09D11/107—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from unsaturated acids 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
- 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
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
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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
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
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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
- C09D11/50—Sympathetic, colour changing or similar 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
- 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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
-
- 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
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
-
- 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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- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
- H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
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Abstract
Description
本発明は、一以上の有機発光材料および/または5000g/mol以下の分子量を有する電荷輸送材料、一以上の有機溶媒と一以上のポリマーを含む組成物であって、前記ポリマーは、アクリル酸エステルおよび/またはメタクリル酸エステル単位を含むことを特徴とする組成物に関する。
a)上記および下記の組成物を基板上に堆積させて、好ましくは、膜または層を形成する工程と、
b)溶媒を、たとえば、蒸発により除去する工程と
を含む方法に関する。
DCyは、出現毎に、同一または異なって、環状基を金属に結合させる少なくとも1つのドナー原子、好ましくは、窒素、カルベンの形態の炭素、またはリンを含有し、また、1つ以上の置換基R1を順に有していてもよい環状基であり、基DCyおよびCCyは、共有結合を介して相互に結ばれ、
CCyは、出現毎に、同一または異なって、環状基を金属に結合させる炭素原子を含有し、また、1つ以上の置換基R1を順に有してもよい環状基であり、
Aは、出現毎に、同一または異なって、モノアニオン性二座キレート配位子、好ましくはジケトネート配位子であり、
R1は、各場合で、同一または異なっており、F、Cl、Br、I、NO2、CN、1〜20個の炭素原子を有する直鎖状、分岐状、または環状のアルキルまたはアルコキシ基(ここで、1つ以上の隣接しないCH2基は、−O−、−S−、−NR2−、−CONR2−、−CO−O−、−C=O−、−CH=CH−または−C≡C−で置き換えられていてもよく、また、ここで、1個以上の水素原子は、Fで置き換えられていてもよい。)または、4〜14個の炭素原子を有し、1つ以上の非芳香族R1ラジカルで置換されていてもよいアリールまたはヘテロアリール基であって、同じ環上または2つの異なる環上のいずれかの複数の置換基R1はまた、一緒になって、順に単環式または多環式の脂肪族または芳香族環系を形成してもよく、
R2は、各場合で同一または異なっており、1〜20個の炭素原子を有する直鎖状、分岐状、または環状のアルキルまたはアルコキシ基(ここで、1つ以上の隣接しないCH2基は、−O−、−S−、−CO−O−、−C=O−、−CH=CH−または−C≡C−で置き換えられていてもよく、また、ここで、1個以上の水素原子は、Fで置き換えられていてもよい。)、または、4〜14個の炭素原子を有し、1つ以上の非芳香族R1ラジカルで置換されていてもよいアリールまたはヘテロアリール基である)。
さらに、複数のラジカルR1間の環系の形成は、ブリッジが、2または3個の配位子CCy-DCyとの間に、または1または2個の配位子CCy-DCyと配位子Aとの間に存在してもよく、多座配位もしくはポリポダル配位子系をなすことを意味する。
発光層の混合物中のドーパントの割合は、好ましくは、0.1〜50.0重量%の間、より好ましくは、0.5〜20.0重量%の間、最も好ましくは、1.0〜10.0重量%の間である。対応して、ホスト材料の割合は、好ましくは、50.0〜99.9重量%の間、より好ましくは、80.0〜99.5重量%の間、最も好ましくは、90.0〜99.0重量%の間である。
000g/mol以下、より好ましくは、1500g/mol以下、最も好ましくは、1000g/mol以下の分子量を有する。
アクリル酸エステル単位としては、先行技術から知られる全ての単位を使用することができる。好ましいのは、エステル基としてC1−10アルキル基、C3−8シクロアルキル基、C6−14アリール基またはC2−13ヘテロアリール基を有するアクリル酸エステルである。より好ましいのは、エステル基として、メチルまたはエチル基を有するアクリル酸エステルである
アクリル酸エステルおよび/またはメタクリル酸エステル単位に加えて、ポリマーは、さらなる反復単位を含むことができる。ポリマーは、0〜95モル%、好ましくは、0〜75モル%、より好ましくは、0〜50モル%の、さらなる反復単位を含む。
Hpは、極性の寄与を意味し、
Hhは、水素結合の寄与を意味し、
MVolは、モル体積を意味する。
本発明による組成物は、追加的に、たとえば、界面活性化合物、潤滑剤、湿潤剤、分散剤、疎水剤、接着剤、流動性向上剤、消泡剤、脱気剤、希釈剤(反応性であっても非反応性であってもよい)、補助剤、着色剤、染料もしくは顔料、増感剤、安定剤、ナノ粒子または阻害剤のような、1種以上のさらなる構成成分を含むことができる。しかし、これらのさらなる成分は、有機発光材料および/または電荷輸送材料を酸化可能であるべきではなく、そうでなくても、有機発光材料および/または電荷輸送材料と化学的に反応可能であるべきではなく、または有機発光材料および/または電荷輸送材料に電気的ドーピング効果を与えるべきではない。
酸化しないか、またはさもなくば有機発光材料および/または電荷輸送材料と化学的に反応しない適切で好ましい湿潤剤は、シロキサン、アルカン、アミン、アルケン、アルキン、アルコールおよび/またはこれら化合物のハロゲン化誘導体より成る基から選ばれる。さらに、フルオロエーテル、フルオロエステルおよび/またはフルオロケトンを使用することもできる。より好ましくは、これらの化合物は、6〜20個の炭素原子、特に、8〜16個の炭素原子を有するメチルシロキサン、C7−14アルカン、C7−14アルケン、C7−14アルキン、7〜14個の炭素原子を有するアルコール、7〜14個の炭素原子を有するフルオロエーテル、7〜14個の炭素原子を有するフルオロエステル、7〜14個の炭素原子を有するフルオロケトンから選ばれる。最も好ましい湿潤剤は、8〜14個の炭素原子を有するメチルシロキサンである。
比較例1
印刷用インクを、式(A)による燐光化合物と、
基本的に、比較例1を繰り返した。しかし、不活性ポリスチレンバインダーを印刷用インクに添加している。印刷用インクは、2,000,000g/molのMWを有する0.5重量%のポリスチレン(Sigma Aldrich製)と、比較例1で述べたような2.5重量%の半導体化合物とを含んでいる。
基本的に、比較例1を繰り返した。しかし、不活性ポリスチレンバインダーを印刷用インクに添加している。印刷用インクは、2,000,000g/molのMWを有する1.0重量%のポリスチレン(Sigma Aldrich製)と、比較例1で述べたような2.5重量%の半導体化合物とを含んでいる。
基本的に、比較例1を繰り返した。しかし、不活性ポリ(メチルメタクリレート)バインダーを印刷用インクに添加している。印刷用インクは、2,400,000g/molのMWを有する0.25重量%のポリ(メチルメタクリレート)(Sigma Aldrich製)と、比較例3で述べたような2.5重量%の半導体化合物とを含んでいる。
基本的に、比較例1を繰り返した。しかし、不活性ポリ(メチルメタクリレート)バインダーを印刷用インクに添加している。印刷用インクは、2,400,000g/molのMWを有する0.5重量%のポリ(メチルメタクリレート)(Sigma Aldrich製)と、比較例4で述べたような2.5重量%の半導体化合物とを含んでいる。
溶液処理されたOLEDのデバイスの調製
溶液から有機発光ダイオードを調製することについての多くの例が、ほとんどがポリマーデバイスについて、文献に記載されている(“PLED”、たとえばWO 2004/037887 A2)。本発明の調合物が良好な膜を生じるだけでなく、良好に機能することを証明するため、OLEDデバイスは標準的な試験セットアップで作られた。典型的なセットアップを図1に示しており、使用するデバイスのレイアウトが図2に示されている。ITO(インジウム-スズ-酸化物)は透明で、スパッタリングによりPETホイルへ堆積され、グラビア印刷されたリソグラフィを介して、それぞれ4画素からなる、6×4mm寸法の10個の基板を得るように構造化された正孔注入アノードである。本願の場合では、基板を自己調製した。
不活性ポリスチレン(PS)バインダーと、不活性ポリ(メチルメタクリレート)(PMMA)バインダーを有するデバイスの比較
比較例6
化合物(A)、(B)、(C)を25g/lの濃度でアニソール中に溶解し、さらに、ポリスチレン(2,000,000g/モル、Aldrich)を5g/lの濃度で不活性バインダーとして添加し、膜形成を改善し、グラビア印刷した。デバイスの特性決定の結果を表4に示す。
化合物(A)、(B)、(C)を25g/lの濃度でアニソール中に溶解し、さらに、ポリ(メチルメタクリレート)(2,400,000g/モル、Aldrich)を5g/lの濃度で不活性バインダーとして添加し、膜形成を改善し、グラビア印刷した。デバイスの特性決定の結果を表4に示す。
Claims (16)
- 一以上の有機発光材料および/または5000g/mol以下の分子量を有する電荷輸送材料、一以上の有機溶媒と一以上のポリマーを含む組成物であって、前記ポリマーは、アクリル酸エステルおよび/またはメタクリル酸エステル単位を含むことを特徴とする組成物。
- 前記ポリマーはアクリル酸エステルおよび/またはメタクリル酸エステル単位から選ばれる5〜100モル%の反復単位を含むことを特徴とする、請求項1に記載の組成物。
- 前記アクリル酸エステルおよび/またはメタクリル酸エステル単位は、エステル基としてC1−10アルキル基、C3−8シクロアルキル基、C6−14アリール基またはC2−13ヘテロアリール基から選ばれるアクリル酸エステルおよび/またはメタクリル酸エステル単位を有することを特徴とする、請求項1または2に記載の組成物。
- 前記ポリマーは、少なくとも500,000g/molの重量平均分子量MWを有することを特徴とする、請求項1〜3の何れか一項に記載の組成物。
- 前記組成物は、25℃で1〜100mPasの範囲の粘度を有することを特徴とする、請求項1〜4の何れか一項に記載の組成物。
- 前記ポリマーは−70〜160℃の範囲のガラス転移温度を有することを特徴とする、請求項1〜5の何れか一項に記載の組成物。
- 前記組成物は、0.01〜20重量%の範囲の前記ポリマーを含むことを特徴とする、請求項1〜6の何れか一項に記載の組成物。
- 前記有機溶媒は、芳香族有機溶媒であることを特徴とする、請求項1〜7の何れか一項に記載の組成物。
- 前記有機溶媒は、芳香族炭化水素、芳香族エーテル、芳香族エステル、芳香族ケトン、ヘテロ芳香族系溶媒およびアニリン誘導体より成る群から選ばれることを特徴とする、請求項8に記載の組成物。
- 前記有機溶媒は、260℃以下の沸点を有することを特徴とする、請求項1〜9の何れか一項に記載の組成物。
- 前記組成物は、少なくとも80重量%の前記有機溶媒を含むことを特徴とする、請求項1〜6の何れか一項に記載の組成物。
- 5000g/mol以下の分子量を有する一以上の前記発光有機材料は、発光し、さらに、38超の原子番号を有する少なくとも一つの原子を含む有機燐光化合物であることを特徴とする、請求項1〜11の何れか一項に記載の組成物。
- 前記有機燐光化合物は、式(1)〜(4)の化合物から選ばれることを特徴とする、請求項12に記載の組成物:
DCyは、出現毎に、同一または異なって、環状基を金属に結合させる少なくとも1つのドナー原子、好ましくは、窒素、カルベンの形態の炭素、またはリンを含有し、また、1つ以上の置換基R1を順に有していてもよい環状基であり、基DCyおよびCCyは、共有結合を介して相互に結ばれ、
CCyは、出現毎に、同一または異なって、環状基を金属に結合させる炭素原子を含有し、また、1つ以上の置換基R1を順に有してもよい環状基であり、
Aは、出現毎に、同一または異なって、モノアニオン性二座キレート配位子、好ましくはジケトネート配位子であり、
R1は、各場合で、同一または異なっており、F、Cl、Br、I、NO2、CN、1〜20個の炭素原子を有する直鎖状、分岐状、または環状のアルキルまたはアルコキシ基(ここで、1つ以上の隣接しないCH2基は、−O−、−S−、−NR2−、−CONR2−、−CO−O−、−C=O−、−CH=CH−または−C≡C−で置き換えられていてもよく、また、ここで、1個以上の水素原子は、Fで置き換えられていてもよい。)または、4〜14個の炭素原子を有し、1つ以上の非芳香族R1ラジカルで置換されていてもよいアリールまたはヘテロアリール基であって、同じ環上または2つの異なる環上のいずれかの複数の置換基R1はまた、一緒になって、順に単環式または多環式の脂肪族または芳香族環系を形成してもよく、
R2は、各場合で同一または異なっており、1〜20個の炭素原子を有する直鎖状、分岐状、または環状のアルキルまたはアルコキシ基(ここで、1つ以上の隣接しないCH2基は、−O−、−S−、−CO−O−、−C=O−、−CH=CH−または−C≡C−で置き換えられていてもよく、また、ここで、1個以上の水素原子は、Fで置き換えられていてもよい。)、または、4〜14個の炭素原子を有し、1つ以上の非芳香族R1ラジカルで置換されていてもよいアリールまたはヘテロアリール基である)。 - 前記組成物が、0.25〜5重量%の有機発光材料および/または5000g/mol以下の分子量を有する電荷輸送材料を含むことを特徴とする、請求項1〜13の何れか一項に記載の組成物。
- 請求項1〜14の何れか一項に記載の組成物の、有機エレクトロルミッセン(EL)デバイス、好ましくは、OLEDデバイスの製造をするためのコーティングまたは印刷インクとしての使用。
- 請求項1〜14の何れか一項に記載の組成物から製造される、有機エレクトロルミッセンデバイス、好ましくは、OLEDデバイス。
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JP2010525111A (ja) * | 2007-04-17 | 2010-07-22 | ゼネラル・エレクトリック・カンパニイ | ポリカルバゾリル(メタ)アクリレート発光組成物 |
JP2013516053A (ja) * | 2009-12-23 | 2013-05-09 | メルク パテント ゲーエムベーハー | 高分子バインダーを含む組成物 |
WO2012132863A1 (ja) * | 2011-03-29 | 2012-10-04 | 凸版印刷株式会社 | インク組成物とそれを用いた有機el素子及びその製造方法 |
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JP6716457B2 (ja) | 2020-07-01 |
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CN105793387A (zh) | 2016-07-20 |
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US20160301003A1 (en) | 2016-10-13 |
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