JP6908587B2 - 着色剤化合物及びこれを含む着色剤材料 - Google Patents
着色剤化合物及びこれを含む着色剤材料 Download PDFInfo
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- JP6908587B2 JP6908587B2 JP2018502632A JP2018502632A JP6908587B2 JP 6908587 B2 JP6908587 B2 JP 6908587B2 JP 2018502632 A JP2018502632 A JP 2018502632A JP 2018502632 A JP2018502632 A JP 2018502632A JP 6908587 B2 JP6908587 B2 JP 6908587B2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000000049 pigment Substances 0.000 claims description 13
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- 0 Cc1c(*)c(C(C(C(*)=C2*)=I(C)C(*)=C2N(*)*)=O)c(*)c(*)c1N(*)C#C Chemical compound Cc1c(*)c(C(C(C(*)=C2*)=I(C)C(*)=C2N(*)*)=O)c(*)c(*)c1N(*)C#C 0.000 description 2
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 125000003636 chemical group Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical group C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical group C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical group C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 125000002521 alkyl halide group Chemical group 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical group CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
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- 239000004305 biphenyl Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
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- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical group C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical group S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
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Classifications
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Description
n×m=a×b (式1)
α、α’−ジブロモ−ρ−キシレン(5g、18.65mmol)及びo−トルイジン(4.2g、39.18mmol)を250mlのアセトンに溶解し、50℃で攪拌した。反応完了後、100mlのH2O及び100mlのDCMを加えて抽出を行った。有機層をMgSO4で乾燥させ濾過した。減圧下で濃縮後、残渣をSiO2カラム処理(Hex:EA=40:1)に供して化合物1を得た。
チオシアン酸カリウム(3.37g、34.76mmol)を300mlのアセトンに溶解し、温度を0℃に冷却した。塩化ベンゾイル(3.67ml、31.6mmol)を滴下で加えた。混合物を室温で1.5時間撹拌した後、次いで再び0℃まで冷却した。30mlのアセトンに溶解した化合物1(10g、31.6mmol)を滴下で加えた。これを室温で2時間撹拌した。反応完了後、200mlのH2Oを加えた。200mlのEAを加え、抽出を2回行った。有機層をMgSO4で乾燥させ濾過した。減圧下で濃縮後、化合物2を得た。
化合物2(15g、23.33mmol)を150mlの2N NaOHに溶解し、15時間還流した。反応完了後、温度を室温まで冷却した。150mlのDCMを加えた後、抽出を2回行った。有機層をMgSO4で乾燥させ濾過した。減圧下で濃縮後、化合物3を得た。
化合物3(5g、11.5mmol)、2−クロロアセトフェノン(1.78g、11.5mmol)、及び重炭酸ナトリウム(2.41g、28.75mmol)を100mlのACNに溶解し、温度を60℃まで上昇させた。3時間撹拌した後、温度を室温まで冷却した。100mlのDCM及び200mlのH2Oを加えた後、抽出を行った。有機層をMgSO4で乾燥させ濾過した。減圧下で濃縮後、残渣をSiO2カラム処理(Hex:EA=40:1)に供して化合物4を得た。
化合物4(7g、11.02mmol)及び4,4’−ビス(ジエチルアミノ)ベンゾフェノン(3.93g、12.12mmol)を150mlのトルエン(無水)に溶解し、POCl3(5.13ml、55.1mmol)を加えた。温度を100℃まで上昇させ、15時間攪拌した。反応完了後、温度を室温まで冷却した。温度を更に氷浴中で4℃まで冷却し、10mlのlPAをゆっくり滴下で加えてクエンチした。50mlのH2Oをゆっくり加え、100mlのDCMを加え、抽出を3回行った。有機層をMgSO4で乾燥させ濾過した。減圧下で濃縮後、残渣をSiO2カラム(DCM:EA:MeOH=5:5:1)に供して化合物5を得た。
化合物5(5g、3.78mmol)及びビス(トリフルオロメタン)スルホンイミドリチウム塩(2.71g、9.46mmol)を100mlのMeOHに溶解し、室温で2時間撹拌した。500mlのH2Oを撹拌下で混合物にゆっくりと滴加で加えた。生成した固体を濾過し、50mlのH2Oで3回洗浄し、化合物6を得た。
8gの実施例1〜6で得られた化合物6及び92gのプロピレングリコールモノメチルエーテルアセテート(PGMEA)をビーズミルに入れ、ジルコニアビーズ(サイズ:0.05〜2mm)を用いて40℃で4〜6時間粉砕して着色剤ミルベース1を得た。
8gの実施例2で得られた化合物7及び92gのPGMEAをビーズミルに入れ、ジルコニアビーズ(サイズ:0.05〜2mm)を用いて40℃で4〜6時間粉砕して着色剤ミルベース2を得た。
(1)輝度及びコントラスト比の測定のためのフィルムの調製:着色剤ミルベースをスピンコーティング(200〜300rpm、15秒間)によってガラス基板(Corningから入手可能なEAGLE−XG FUSION GLASS)にコーティングして約2ミクロンの厚さのフィルムを形成し、90秒間、90℃でプリベークした。その後、フィルムを20分間、230℃でポストベークに供した。
Claims (11)
- 以下の式(I):
(式中、
Xは、独立して、酸素原子、−NH−、又は硫黄原子であり、
R11は、独立して、水素原子、置換されていてもよいアルキル基、及び置換されていてもよいアリール基からなる群から選択され、
R21は、独立して、水素原子、置換されていてもよいアルキル基、及び置換されていてもよいアリール基からなる群から選択され、
R31、R32、R33、R34、R35、R36、R37、及びR38のそれぞれは、独立して、水素原子、ハロゲン原子、置換されていてもよいアルキル基、置換されていてもよいアルコキシ基、シアノ基、ニトロ基、スルホニル基、及び水酸基からなる群から選択され、
R41、R42、R43、及びR44のそれぞれは、独立して、水素原子、置換されていてもよいアルキル基、及び置換されていてもよいアリール基からなる群から選択され、R41及びR42、又はR43及びR44のそれぞれは、一緒に結合されて環構造を形成することができ、
Lは、少なくとも1つの芳香環を含む「n」価の連結基であり、
Anは、対アニオンであり、及び
以下の式:
n×m=a×b (式1)
が満たされていることを条件として、nは、2以上の整数であり、mは、1以上の整数であり、aは、1以上の整数であり、且つbは、1以上の整数である)を有し、
Ana−は、少なくとも1つのスルホニル基を含むアニオン性化合物である、化合物。 - Lは、ベンゼン基を含む、請求項1に記載の化合物。
- Xは、硫黄原子である、請求項1〜3のいずれか一項に記載の化合物。
- R11は、置換されていてもよいアリール基である、請求項1〜4のいずれか一項に記載の化合物。
- R21は、置換されていてもよいアリール基である、請求項1〜5のいずれか一項に記載の化合物。
- 請求項1〜6のいずれか一項に記載の化合物と、任意選択的に少なくとも別の染料又は顔料とを含む着色剤材料。
- 請求項1〜6のいずれか一項に記載の化合物又は請求項8に記載の着色剤材料と、任意選択的に、顔料、染料、バインダー、分散助剤又は分散剤、重合性モノマー、溶媒、抑制剤、重合開始剤、及びそれらの任意の組合せからなる群から選択される少なくとも1つの成分とを含む、カラーフィルターを形成するための組成物。
- (A)着色剤材料と、(B)溶媒と、(C)バインダーとを含み、着色剤材料(A)は、請求項1〜6のいずれか一項に記載の化合物又は請求項8に記載の着色剤材料を含む、カラーフィルターのためのミルベース組成物。
- ディスプレイデバイスのためのカラーフィルターを調製するための、請求項1〜6のいずれか一項に記載の化合物又は請求項8に記載の着色剤材料の使用。
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