JP2020531643A - バインダー樹脂、感光性樹脂組成物、感光材、カラーフィルタ及びディスプレイ装置 - Google Patents
バインダー樹脂、感光性樹脂組成物、感光材、カラーフィルタ及びディスプレイ装置 Download PDFInfo
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- JP2020531643A JP2020531643A JP2020511188A JP2020511188A JP2020531643A JP 2020531643 A JP2020531643 A JP 2020531643A JP 2020511188 A JP2020511188 A JP 2020511188A JP 2020511188 A JP2020511188 A JP 2020511188A JP 2020531643 A JP2020531643 A JP 2020531643A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- G02—OPTICS
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Abstract
[化学式1]
【化1】
[化学式2]
【化2】
[化学式3]
【化3】
前記化学式1〜3において、
R1〜R5は、互いに同一であるか異なっており、それぞれ独立して、水素;又は置換もしくは非置換のアルキル基であり、
r3は、0〜4の整数であり、r3が2以上の場合、R3は互いに同一であるか異なっており、
r4は、0〜5の整数であり、r4が2以上の場合、R4は同一であるか異なっており、
L1〜L4は、互いに同一であるか異なっており、それぞれ独立して、置換もしくは非置換のアルキレン基であり、
Aは、熱硬化性基である。
Description
[化学式1]
R1〜R5は、互いに同一であるか異なっており、それぞれ独立して、水素;又は置換もしくは非置換のアルキル基であり、
r3は、0〜4の整数であり、r3が2以上の場合、R3は互いに同一であるか異なっており、
r4は、0〜5の整数であり、r4が2以上の場合、R4は同一であるか異なっており、
L1〜L4は、互いに同一であるか異なっており、それぞれ独立して、置換もしくは非置換のアルキレン基であり、
Aは、熱硬化性基である。
[化学式1]
R1〜R5は、互いに同一であるか異なっており、それぞれ独立して、置換もしくは非置換のアルキル基であり、
r3は、0〜4の整数であり、r3が2以上の場合、R3は互いに同一であるか異なっており、
r4は、0〜5の整数であり、r4が2以上の場合、R4は同一であるか異なっており、
L1〜L4は、互いに同一であるか異なっており、それぞれ独立して、置換もしくは非置換のアルキレン基であり、
Aは、熱硬化性基である。
[化学式2−1]
[化学式4]
L5及びL6は、互いに同一であるか異なっており、それぞれ独立して、置換もしくは非置換のアルキレン基であり、
R41、R42、R51及びR52は、互いに同一であるか異なっており、それぞれ独立して、水素;又は置換もしくは非置換のアルキル基であり、
r42は、0〜5の整数であり、r42が2以上の場合、R42は互いに同一であるか異なっており、
r52は、0〜11の整数であり、r52が2以上の場合、R52は互いに同一であるか異なっている。
反応容器に下記化学式2−2の構造で表されるベンゾフェノンメタクリレート/下記化学式4−1で表されるスチレン/下記化学式1−1で表されるグリシジルメタクリレート/下記化学式3−1で表されるメタクリル酸を、バインダー樹脂固形分の総重量を基準に、それぞれ11、31、45、13重量%で投入した後、溶媒(プロピレングリコールモノメチルエーテルアセタート、Cas No. 108−65−6)と混合して、窒素雰囲気で60℃に昇温した。その後、熱重合開始剤v−65(2,2'−Azobis(2,4−dimethylvaleronitrile)を、バインダー樹脂固形分の総重量を基準に10重量部投入して、16時間反応させて、バインダー樹脂を製造した。
反応容器に上記化学式2−2の構造で表されるベンゾフェノンメタクリレート/上記化学式1−1で表されるグリシジルメタクリレート/上記化学式3−1で表されるメタクリル酸を、バインダー樹脂固形分の総重量を基準に、それぞれ17、70、13重量%で投入した後、溶媒と混合して、窒素雰囲気で60℃に昇温した。その後、熱重合開始剤v−65(2,2'−Azobis(2,4−dimethylvaleronitrile)を、バインダー樹脂固形分の総重量を基準に10重量部投入して、16時間反応させて、バインダー樹脂を製造した。
反応容器に上記化学式2−2の構造で表されるベンゾフェノンメタクリレート/下記化学式5−1の構造で表されるシクロヘキシルメタクリレート/上記化学式1−1で表されるグリシジルメタクリレート/上記化学式3−1で表されるメタクリル酸を、バインダー樹脂固形分の総重量を基準に、それぞれ10、41、38、13重量%で投入した後、溶媒と混合して、窒素雰囲気で60℃に昇温した。 その後、熱重合開始剤v−65(2,2'−Azobis(2,4−dimethylvaleronitrile)を、バインダー樹脂固形分の総重量を基準に10重量部投入して、16時間反応させて、バインダー樹脂を製造した。
トリアリールメタン系Blue染料3g及び上記合成例1で製造されたバインダー樹脂6g、多官能性モノマーとしてジペンタエリスリトールヘキサアクリレート6g、光開始剤としてOXE−02 0.8g、溶媒としてプロピレングリコールモノメチルエーテルアセタート84.2gを混合し、上記混合物を3時間撹拌して、感光性樹脂組成物を製造した。
上記合成例1で製造されたバインダー樹脂の代わりに、上記合成例2で製造されたバインダー樹脂6gを使用したこと以外には、上記実施例1と同様の方法で感光性樹脂組成物を製造した。
上記合成例1で製造されたバインダー樹脂の代わりに、上記合成例3で製造されたバインダー樹脂6gを使用したこと以外には、実施例1と同様の方法で感光性樹脂組成物を製造した。
反応容器に上記化学式4−1で表されるスチレン/上記化学式1−1で表されるグリシジルメタクリレート/上記化学式3−1で表されるメタクリル酸を、バインダー樹脂固形分の総重量を基準に、それぞれ42、45、13重量%で投入した後、溶媒と混合して、窒素雰囲気で60℃に昇温した。その後、熱重合開始剤v−65(2,2'−Azobis(2,4−dimethylvaleronitrile)を、バインダー樹脂固形分の総重量を基準に10重量部投入して、16時間反応させて、バインダー樹脂を製造した。
反応容器に上記化学式2のR3がヒドロキシ基(−OH)であり、r3が1であり、R4が水素であり、r4が0であり、L3がメチレン基であり、R2がメチル基である構造を含むベンゾフェノンモノマー/上記化学式4−1で表されるスチレン/上記化学式1−1で表されるグリシジルメタクリレート/上記化学式3−1で表されるメタクリル酸を、バインダー樹脂固形分の総重量を基準に、それぞれ11.31、45、13重量%で投入した後、溶媒と混合して、窒素雰囲気で60℃に昇温した。その後、熱重合開始剤v−65(2,2'−Azobis(2,4−dimethylvaleronitrile)を、バインダー樹脂固形分の総重量を基準に10重量部投入して、16時間反応させて、バインダー樹脂を製造した。製造されたバインダー樹脂の酸価は85KOH mg/g、重量平均分子量は9,000g/molである。
上記合成例1で製造されたバインダー樹脂の代わりに、上記比較合成例1で製造されたバインダー樹脂6gを使用したこと以外には、上記実施例1と同様の方法で感光性樹脂組成物を製造した。
上記合成例1で製造されたバインダー樹脂の代わりに、上記比較合成例2で製造されたバインダー樹脂6gを使用したこと以外には、上記実施例1と同様の方法で感光性樹脂組成物を製造した。
上記実施例1〜3及び比較例1及び2で得られた感光性樹脂組成物の染料溶出程度を測定するために、上記感光性樹脂組成物をガラスにスピンコート(spin coating)し、約100℃で2分プリベーク(prebake)して、フィルムを形成させた。
○:全然染み出ない。
△:現像工程初期には染み出るが、一定時間後それ以上染み出ない。
×:現像の全工程にかけてずっと染み出る。
○:全然染み出ない。
△:少し染み出る。
×:濃く染み出るか、パターンがガラス基板から剥離される。
感光性樹脂組成物の耐熱性を確認するために、下記のような順序で実験した。
(1)240℃ 20min ポストベーク(Post−baking)後、輝度測定
(2)240℃ 60min 追加ベーク後、輝度測定
(3)(1)−(2)間の輝度変化幅を測定
(4)輝度変化率(%)=(3)*100/(1)で耐熱性を確認
実施例1〜3及び比較例1及び2による感光性樹脂組成物を用いて、現像工程後に残っている最小パターンの大きさを測定した。その結果を下記表3に記載した。
Claims (10)
- 前記バインダー樹脂は、下記化学式4又は5で表される構造のうち少なくとも一つをさらに含むものである、請求項1または2に記載のバインダー樹脂:
[化学式4]
R41、R42、R51及びR52は、互いに同一であるか異なっており、それぞれ独立して、水素;又は置換もしくは非置換のアルキル基であり、
r42は、0〜5の整数であり、r42が2以上の場合、R42は互いに同一であるか異なっており、
r52は、0〜11の整数であり、r52が2以上の場合、R52は互いに同一であるか異なっている。 - 前記化学式1で表される構造10mol%〜90mol%;前記化学式2で表される構造1mol%〜20mol%;及び前記化学式3で表される構造5mol%〜40mol%を含むものである、請求項1から3のいずれか一項に記載のバインダー樹脂。
- 前記バインダー樹脂の重量平均分子量は、3,000g/mol〜50,000g/molである、請求項1から4のいずれか一項に記載のバインダー樹脂。
- 請求項1〜5のいずれか一項に記載のバインダー樹脂;染料化合物;多官能性モノマー;光開始剤;及び溶媒を含む感光性樹脂組成物。
- 前記感光性樹脂組成物中の固形分の総重量を基準に、前記染料化合物の含量は4重量%〜20重量%であり、前記バインダー樹脂の含量は20重量%〜50重量%であり、前記多官能性モノマーの含量は20重量%〜50重量%であり、前記光開始剤の含量は1重量%〜5重量%である、請求項6に記載の感光性樹脂組成物。
- 請求項6または7に記載の感光性樹脂組成物を用いて製造された感光材。
- 請求項8に記載の感光材を含むカラーフィルタ。
- 請求項9に記載のカラーフィルタを含むディスプレイ装置。
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CN111032713A (zh) | 2020-04-17 |
KR102247290B1 (ko) | 2021-04-30 |
KR20200012523A (ko) | 2020-02-05 |
JP6996050B2 (ja) | 2022-01-17 |
TW202010814A (zh) | 2020-03-16 |
CN111032713B (zh) | 2021-12-10 |
WO2020022670A1 (ko) | 2020-01-30 |
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