JP2022550781A - カラーフィルタを調製するための組成物 - Google Patents
カラーフィルタを調製するための組成物 Download PDFInfo
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- JP2022550781A JP2022550781A JP2022519807A JP2022519807A JP2022550781A JP 2022550781 A JP2022550781 A JP 2022550781A JP 2022519807 A JP2022519807 A JP 2022519807A JP 2022519807 A JP2022519807 A JP 2022519807A JP 2022550781 A JP2022550781 A JP 2022550781A
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- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 230000005669 field effect Effects 0.000 description 1
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
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- 239000001257 hydrogen Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
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- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001062 red colorant Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000542 sulfonic acid 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
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Abstract
Description
i)着色剤と、
ii)ラジカル発生光開始剤と、
iii)繰り返し単位の少なくとも40mol%が下記式(I)に従う単位である、ポリマーと:
R1は、各々存在に対して独立して、H又はCH3であり、
R2は、下記式(II)で示される基であり:
Lは、連結基であり、nは、0又は1であり、Xは各々存在に対して独立して、O又はCH2である)、
R3は、各々存在に対して独立して、H、COOH、及び式(II)で示される基である)、
iv)ポリマーiii)の重量に基づいて計算されて0.0~10.0重量%の、1500g/mol未満の分子量を有する1種又は複数のエチレン性不飽和重合性モノマーと、
を含む、組成物を提供する。
R1は、各々存在に対して独立して、H又はCH3であり、
R2は、下記式(II)で示される基であり:
Lは、連結基であり、nは、0又は1であり、Xは各々存在に対して独立して、O又はCH2である)、
R3は、各々存在に対して独立して、H、COOH、及び式(II)で示される基である)。
i)20.0~60.0重量%の着色剤と、
ii)1.0~10.0重量%の光開始剤と、
iii)20.0~70.0重量%の、繰り返し単位の40.0~80.0mol%が下記式(I)に従う単位であり、65~170mg-KOH/gの範囲内の酸価を有するポリマーと:
R1は、各々存在に対して独立して、H又はCH3であり、
R2は、下記式(II)で示される基であり:
Lは、連結基であり、nは、0であり、Xは、CH2である)、
R3は、Hである)、
iv)0.0~1.5重量%の、1500g/mol未満の分子量を有する1種又は複数のエチレン性不飽和重合性モノマーと、
v)5.0~20.0重量%の、着色剤のための分散剤と、
vi)0.0~4.0重量%の1種又は複数のアルコキシシラン基を有する化合物と、
を含み、
重量%は、組成物の非揮発分に基づいて計算されている。
a)本発明による組成物を基材に塗布するステップと、
b)塗布された組成物の選択エリアを化学線への暴露により硬化して、塗布された組成物の硬化エリアと未硬化エリアのパターンを作製するステップと、
を含む。
ポリマーP1~P8の調製のための基本手順
溶媒PGMEAは、窒素雰囲気下で反応容器に入れられ、100°に加熱された。
ポリマー溶液が、30分間、撹拌されながら光開始剤及びPGMEAと混合された。溶液は、予め洗浄された1’’ガラス基材上に1000rpmで回転塗布された。ホットプレート上でのプリベーク(90℃、2分)の後、基材がUV光に暴露された(100mJ/cm2、i線)。基材はその後、0.2%ドデシル硫酸ナトリウムと共に0.5%NaOH溶液を含有するビーカに60秒間入れられて、脱イオン水で洗浄された。薄膜保持率(film retention)は、顕色浴への浸漬前と後の乾燥薄膜の層厚の比率から決定された。層厚は、表面形状測定装置(Surface Profiler 150 Veeco)の助力を得て、薄膜をスクラッチすること、及びステップ高さを決定すること、により測定された。30mol%DCPD繰り返し単位を含有する比較用ポリマーP8の光架橋層は、極わずかの被膜保持率を呈し、ポリマーの不充分な架橋を示した。
組成物1
ミルベースMB1の調製
Irgaphor Red BT-CF 7.5g、ポリマー溶液P2 10.0g、LPN21169 5.6g、PGMEA 24.4g及びn-ブタノール2.5gが、一緒にガラス瓶に入れられた。Zirconoxビーズ 100gが添加され、分散工程がLAU分散機DA S200により40℃で4時間の期間にわたり実施された。
ミルベースMB2の調製
Irgaphor Red BT-CF 7.5g、ポリマー溶液P5 12.5g、LPN21169 5.6g、PGMEA 21.9g及びn-ブタノール2.5gが、一緒にガラス瓶に入れられた。Zirconoxビーズ 100gが添加され、分散工程がLAU分散機DA S200により40℃で4時間の期間にわたり実施された。
ミルベースMB3の調製
Irgaphor Red BT-CF 7.5g、ポリマー溶液P4 12.5g、LPN21169 5.6g、PGMEA 21.9g及びn-ブタノール2.5gが、二重壁ステンレス鋼コンテナ内で撹拌されながら混合された。Zirconoxビーズ 100gが添加され、分散工程が溶解機Dispermat LC30(VMA-Getzmann)を用いて40℃で10時間の期間にわたり実施された。
カラーフィルタ1
組成物1が、予め洗浄された1’’ガラス基材上に1000rpmで回転塗布された。ホットプレート上でのプリベーク(150℃、2分)の後、基材がシャドウマスクで覆われて(USAF1951分解能ターゲット)、UV光に暴露された(100mJ/cm2、i線)。基材はその後、0.2%ドデシル硫酸ナトリウムと共に0.5%NaOH溶液を含有するビーカに120秒間入れられて、脱イオン水で洗浄された。そして、フォトパターニングされた基材が、120℃で5分間焼成された。膜厚1.3μmで7μmの最小線幅分解能が、得られた。
組成物2が、予め洗浄された1’’ガラス基材上に2000rpmで回転塗布された。ホットプレート上でのプリベーク(120℃、5分)の後、基材がシャドウマスクで覆われて(USAF1951分解能ターゲット)、UV光に暴露された(200mJ/cm2、i線)。基材はその後、0.2%ドデシル硫酸ナトリウムと共に0.5%NaOH溶液を含有するビーカに150秒間入れられて、脱イオン水で洗浄された。そして、フォトパターニングされた基材が、120℃で5分間焼成された。膜厚1.6μmで8μmの最小線幅分解能が、得られた。
組成物3が、予め洗浄された1’’ガラス基材上に1500rpmで回転塗布された。ホットプレート上でのプリベーク(90℃、2分)の後、基材がシャドウマスクで覆われて(USAF1951分解能ターゲット)、UV光に暴露された(200mJ/cm2、i線)。基材はその後、0.2%ドデシル硫酸ナトリウムと共に0.5%NaOH溶液を含有するビーカに100秒間入れられて、脱イオン水で洗浄された。そして、フォトパターニングされた基材が、120℃で5分間焼成された。膜厚1.5μmで10μmの最小線幅分解能が、得られた。
Claims (17)
- i)着色剤と、
ii)ラジカル発生光開始剤と、
iii)繰り返し単位の少なくとも40mol%が下記式(I)に従う単位である、ポリマーと:
R1は、各々存在に対して独立して、H又はCH3であり、
R2は、下記式(II)で示される基であり:
Lは、連結基であり、nは、0又は1であり、Xは各々存在に対して独立して、O又はCH2である)、
R3は、各々存在に対して独立して、H、COOH、及び式(II)で示される基である)、
iv)前記ポリマーiii)の重量に基づいて計算されて0.0~10.0重量%の、1500g/mol未満の分子量を有する1種又は複数のエチレン性不飽和重合性モノマーと、
を含む、組成物。 - 前記ポリマーiii)の重量に基づいて計算されて0.0~5.0重量%の、1500g/mol未満の分子量を有し、アルコキシシラン基を有さない、1種又は複数のエチレン性不飽和重合性モノマーを含む、請求項1に記載の組成物。
- 1500g/mol未満の分子量を有し、アルコキシシラン基を有さない、1種又は複数のエチレン性不飽和重合性モノマーを実質的に不含とする、請求項1又は2に記載の組成物。
- 前記ポリマーiii)が、酸基をさらに含む、請求項1~3のいずれか1項に記載の組成物。
- 前記酸基が、カルボン酸基である、請求項4に記載の組成物。
- 前記ポリマーiii)が、65~170mg-KOH/gの範囲内の酸価を有する、請求項4又は5に記載の組成物。
- 前記酸基が、少なくとも4個の炭素原子を有する連結基を介して前記ポリマーの主鎖に連結される、請求項4~6のいずれかに記載の組成物。
- 前記ポリマーiii)が、15,000~150,000g/molの範囲内の重量平均分子量Mwを有する、請求項1~7のいずれか1項に記載の組成物。
- 前記着色剤が、顔料及び染色剤の少なくとも一方を含む、請求項1~8のいずれか1項に記載の組成物。
- 多官能性チオールを実質的に不含とする、請求項1~9のいずれか1項に記載の組成物。
- 前記着色剤のための分散剤をさらに含む、請求項1~10のいずれか1項に記載の組成物。
- 1つ又は複数のアルコキシシラン基を有する化合物をさらに含む、請求項1~11のいずれか1項に記載の組成物。
- i)20.0~60.0重量%の着色剤と、
ii)1.0~10.0重量%の光開始剤と、
iii)20.0~70.0重量%の、繰り返し単位の40.0~80.0mol%が下記式(I)に従う単位であり、65~170mg-KOH/gの範囲内の酸価を有する、ポリマーと:
R1は、各々存在に対して独立して、H又はCH3であり、
R2は、下記式(II)で示される基であり:
Lは、連結基であり、nは、0であり、Xは、CH2である)、
R3は、Hである)、
iv)0.0~1.5重量%の、1500g/mol未満の分子量を有し、アルコキシシラン基を有さない、1種又は複数のエチレン性不飽和重合性モノマーと、
v)5.0~20.0重量%の、着色剤のための分散剤と、
vi)0.0~4.0重量%の1種又は複数のアルコキシシラン基を有する化合物と、
を含み、
前記重量%が前記組成物の非揮発分に基づいて計算されている、
請求項1~12のいずれか1項に記載の組成物。 - a)請求項1~13のいずれか1項に記載の組成物を基材に塗布するステップと、
b)前記塗布された組成物の選択エリアを化学線への暴露により硬化して、前記塗布された組成物の硬化エリアと未硬化エリアのパターンを作製するステップと、
を含む、カラーフィルタを調製するための工程。 - アルカリ液処理剤での処理により前記塗布された組成物の前記未硬化エリアを溶解するステップc)を含む、請求項14に記載の工程。
- 請求項14又は15に記載の工程により得ることが可能なカラーフィルタ。
- 請求項16に記載のカラーフィルタを含む、液晶ディスプレイ、液晶スクリーン、色解像デバイス、又はセンサ。
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