JP2005315984A - レジスト組成物及びその塗膜 - Google Patents
レジスト組成物及びその塗膜 Download PDFInfo
- Publication number
- JP2005315984A JP2005315984A JP2004131488A JP2004131488A JP2005315984A JP 2005315984 A JP2005315984 A JP 2005315984A JP 2004131488 A JP2004131488 A JP 2004131488A JP 2004131488 A JP2004131488 A JP 2004131488A JP 2005315984 A JP2005315984 A JP 2005315984A
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- JP
- Japan
- Prior art keywords
- group
- composition
- fluororesin
- alkali
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229920005989 resin Polymers 0.000 claims abstract description 106
- 239000011347 resin Substances 0.000 claims abstract description 106
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 49
- 239000007787 solid Substances 0.000 claims abstract description 23
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 21
- 239000000178 monomer Substances 0.000 claims description 99
- 238000000576 coating method Methods 0.000 claims description 83
- 239000011248 coating agent Substances 0.000 claims description 82
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 76
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 51
- -1 perfluoro group Chemical group 0.000 claims description 49
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 13
- 230000009471 action Effects 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
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- 230000036211 photosensitivity Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 39
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- 229920003180 amino resin Polymers 0.000 description 4
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- 239000005056 polyisocyanate Chemical class 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
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- BFQFFNWLTHFJOZ-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=2C=C3OCOC3=CC=2)=N1 BFQFFNWLTHFJOZ-UHFFFAOYSA-N 0.000 description 3
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Abstract
【解決手段】炭素数4〜6のパーフルオロアルキル基を有し、フッ素原子含有率が7〜35質量%である含フッ素樹脂(A)及び波長100〜600nmの光に反応する感光性成分を含むレジスト組成物であって、組成物の全固形分に対する含フッ素樹脂(A)の割合は0.1〜30質量%であることを特徴とするレジスト組成物及びその塗膜。
【選択図】なし
Description
[1]式1で表される単量体から形成される単量体単位を有し、フッ素原子含有率が7〜35質量%である含フッ素樹脂(A)及び波長100〜600nmの光に反応する感光性成分を含むレジスト組成物であって、組成物の全固形分に対する含フッ素樹脂(A)の割合は0.1〜30質量%であることを特徴とするレジスト組成物。
CH2=CH(R1)COOXRf ・・・式1
式中、R1は、水素原子、メチル基又はトリフルオロメチル基、Xは炭素数1〜6の2価のフッ素原子を含まない有機基を示し、Rfは、炭素数4〜6のパーフルオロアルキル基を示す。
[2]前記感光性成分は光酸発生剤(B)と、カルボキシル基及び/又はフェノール性水酸基を有するアルカリ可溶性樹脂(C)と、酸の作用によりカルボキシル基又はフェノール性水酸基と反応し得る基を2個以上有する化合物である酸架橋剤(D)とを含む[1]記載のレジスト組成物。
[3]含フッ素樹脂(A)がカルボキシル基及び/又は水酸基を有する[2]に記載の組成物。
[4]前記感光性成分は光ラジカル開始剤(E)と、1分子内に酸性基及び2個以上のエチレン性二重結合を有するアルカリ可溶性樹脂(F)とを含む[1]記載の組成物。
[5]前記感光性成分は2個以上のエチレン性二重結合を有し、かつ酸性基を有しないラジカル架橋剤(G)をさらに含む[4]に記載の組成物。
[6]前記含フッ素樹脂(A)はエチレン性二重結合を有する[4]又は[5]に記載の組成物。
[7]前記アルカリ可溶性樹脂(F)はカルボキシル基及び/又は水酸基を有し、前記感光性成分は熱の作用によりカルボキシル基及び/又は水酸基と反応し得る基を2個以上有する化合物である熱架橋剤(H)をさらに含む[4]〜[6]のいずれかに記載のレジスト組成物。
[8][1]〜[7]のいずれかに記載の組成物より得られる塗膜。
まず、含フッ素樹脂(A)と、光酸発生剤(B)と、カルボキシル基及び/又はフェノール性水酸基を有するアルカリ可溶性樹脂(C)と、酸の作用によりカルボキシル基及び/又はフェノール性水酸基と架橋し得る反応性基を2個以上有する化合物である酸架橋剤(D)とを含むネガ型レジスト組成物が好ましい態様のひとつである。以下、本明細書において「第1の組成物」という。
CH2=CH(R1)COOXRf ・・・式1
式中、R1は、水素原子、メチル基又はトリフルオロメチル基、Xは炭素数1〜6の2価の有機基を示し、Rfは、炭素数4〜6のパーフルオロアルキル基を示す。
CH2=CH(R1)COOR2Rf
CH2=CH(R1)COOR2NR3SO2Rf
CH2=CH(R1)COOR2NR3CORf
CH2=CH(R1)COOCH2CH(OH)R4Rf
ここで、R2は炭素数1〜6のアルキレン基を、R3は水素原子又は炭素数1〜4のアルキル基を、R4は単結合又は炭素数1〜4のアルキレン基を示す。
光ラジカル開始剤(E)としては、例えば、ベンジル、ジアセチル、メチルフェニルグリオキシレート、9,10−フェナンスレンキノン等のα−ジケトン類、ベンゾイン等のアシロイン類、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル等のアシロインエーテル類、チオキサントン、2−クロロチオキサントン、2−メチルチオキサントン、2,4−ジメチルチオキサントン、イソプロピルチオキサントン、2,4−ジエチルチオキサントン、2,4−ジクロロチオキサントン、2,4−ジイソプロピルチオキサントン、チオキサントン−4−スルホン酸等のチオキサントン類、ベンゾフェノン、4,4´−ビス(ジメチルアミノ)ベンゾフェノン、4,4´−ビス(ジエチルアミノ)ベンゾフェノン等のベンゾフェノン類、アセトフェノン、2−(4−トルエンスルホニルオキシ)−2−フェニルアセトフェノン、p−ジメチルアミノアセトフェノン、2,2´−ジメトキシ−2−フェニルアセトフェノン、p−メトキシアセトフェノン、2−メチル[4−(メチルチオ)フェニル]−2−モルフォリノ−1−プロパノン、2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタン−1−オン等のアセトフェノン類、アントラキノン、2−エチルアントラキノン、カンファーキノン、1,4−ナフトキノン等のキノン類、2−ジメチルアミノ安息香酸エチル、4−ジメチルアミノ安息香酸エチル、4−ジメチルアミノ安息香酸(n−ブトキシ)エチル、4−ジメチルアミノ安息香酸イソアミル、4−ジメチルアミノ安息香酸2−エチルヘキシル等のアミノ安息香酸類、フェナシルクロライド、トリハロメチルフェニルスルホン等のハロゲン化合物、アシルホスフィンオキシド類、ジ−t−ブチルパーオキサイド等の過酸化物等が挙げられる。
まず、基材に本発明の組成物を塗布する。基材としては、その材質は特に限定されるものではないが、例えば、各種ガラス板、ポリエチレンテレフタレート等のポリエステル、ポリプロピレン、ポリエチレン等のポリオレフィン、ポリカーボネート、ポリメチルメタクリレート、ポリスルホン、ポリイミド等の熱可塑性プラスチックシート、エポキシ樹脂、ポリエステル樹脂、ポリ(メタ)アクリル樹脂等の熱硬化性プラスチックシート等を挙げることができる。特に、耐熱性の点からガラス板、ポリイミド等の耐熱性プラスチックが好ましく用いられる。
重量平均分子量はゲルパーミエーションクロマトグラフィー法によりポリスチレンを標準物質として測定した値である。
含フッ素樹脂に含まれるフッ素原子の含有率は、以下の手法で測定した。得られた含フッ素樹脂を1200℃で完全に燃焼分解させ、発生したガスを50gの水に吸収させた。得られた水溶液のフッ化物イオン量を定量し、含フッ素樹脂に含まれるフッ素原子の含有率を算出した。
酸価(mgKOH/g)、水酸基価(mgKOH/g)、1分子中のエチレン性二重結合の数は、単量体成分の配合割合から算出した理論値である。
C4FMA:CH2=C(CH3)COOCH2CH2(CF2)4F
C6FMA:CH2=C(CH3)COOCH2CH2(CF2)6F
C8FA:CH2=CHCOOCH2CH2(CF2)8F
MAA:メタクリル酸、2−HEMA:2−ヒドロキシエチルメタクリレート、MMA:メタクリル酸メチル、CHMA:シクロヘキシルメタクリレート、IBMA:イソボルニルメタクリレート、
V−70:2,2’−アゾビス(4−メトキシ−2,4−ジメチルバレロニトリル)(和光純薬社製、商品名V−70)、2−ME:2−メルカプトエタノール、
MOI:2−メタクリロイルオキシエチルイソシアネート、DBTDL:ジブチル錫ジラウレート、BHT:2,6−ジ−t−ブチル−p−クレゾール、
MPトリアジン:2−(4−メトキシフェニル)−4,6−ビス(トリクロロメチル)−1,3,5トリアジン
TAZ−107:2−(1,3ベンゾジオキソール−5−イル)−4,6−ビス(トリクロロメチル)−1,3,5トリアジン(みどり化学社製、商品名TAZ−107)
WPAG199:ビス(p−トルエンスルホニル)ジアゾメタン(和光純薬社製、商品名WPAG−199)
NW−100LM:メチルエーテル化メラミン共重合体(三和ケミカル社製、商品名ニカラックNW−100LM)
IR907:ラジカル開始剤(チバ−ガイギー社製、商品名IRGACURE−907)
IR369:ラジカル開始剤(チバ−ガイギー社製、商品名IRGACURE−369)
DEAB:4,4’−ビス(ジエチルアミノ)ベンゾフェノン
DETX−S:イソプロピルチオキサンソン(日本化薬社製、商品名DETX−S)
CCR1115:クレゾールホルムアルデヒド型共重合体(日本化薬社製、商品名CCR−1115:固形分60質量%、1分子あたりのエチレン性二重結合数は平均10個。)
D310:ジペンタエリスリトールペンタアクリレート:(日本化薬社製、商品名KAYARAD D−310)
157S65:ビスフェノールAノボラック型(ジャパンエポキシレジン社製、商品名エピコート157S65)
KBM403:3−グリシドキシプロピルトリメトキシシラン(信越化学工業社製、商品名KBM−403)
DEGDM:ジエチレングリコールジメチルエーテル
CB:カーボンブラック(平均粒径=120nm、プロピレングリコールモノメチルエーテルアセテート溶液、固形分20質量%)。
<含フッ素樹脂(A−1)の合成>
撹拌機を備えた内容積1Lの反応槽に、アセトン(556.0g)、C6FMA(96.0g)、2−HEMA(96.0g)、MMA(48.0g)、連鎖移動剤2−ME(6.2g)及び重合開始剤V−70(4.5g)を仕込み、窒素雰囲気下に撹拌しながら、40℃で18時間重合させ、含フッ素樹脂(A−1)の溶液を得た。得られた含フッ素樹脂(A−1)のアセトン溶液に水を加え再沈精製し、次いで石油エーテルにて再沈精製し、真空乾燥し、含フッ素樹脂(A−1)の238gを得た。重量平均分子量は5600であった。
<含フッ素樹脂(A−2)〜(A−9)、(R−1)〜(R−3)の合成>
含フッ素樹脂(A−1)の合成において、原料の配合を表1のように変更した他は同様の重合反応により、含フッ素樹脂(A−2)〜(A−9)、含フッ素樹脂(R−1)〜(R−3)を得た。
<含フッ素樹脂(A−10)の合成>
温度計、撹拌機、加熱装置を備えた内容量300mLのガラス製フラスコに、含フッ素樹脂(A−1)(100g)、MOI(47.7g)、DBTDL(0.19g)、BHT(2.4g)及びアセトン(100g)を仕込み、撹拌しながら、30℃で18時間重合させ、含フッ素樹脂(A−10)の溶液を得た。得られた含フッ素樹脂(A−10)のアセトン溶液に水を加え再沈精製し、次いで石油エーテルにて再沈精製し、真空乾燥し、含フッ素樹脂(A−10)の145gを得た。重量平均分子量は8700であった。
<含フッ素樹脂(A−11)〜(A−17)、含フッ素樹脂(R−4)〜(R−6)の合成>
含フッ素樹脂(A−10)の合成において、原料の配合を表2のように変更した他は同様の重合反応により含フッ素樹脂(A−11)〜(A−17)、(R−4)〜(R−6)を得た。
<アルカリ可溶性樹脂(C−1)の合成>
撹拌機を備えた内容積1Lの反応槽に、アセトン(555.0g)、MAA(33.6g)、2−HEMA(134.4g)、IBMA(72.0g)、連鎖移動剤2−ME(3.7g)及び重合開始剤V−70(5.4g)を仕込み、窒素雰囲気下に撹拌しながら、40℃で18時間重合させ、アルカリ可溶性樹脂(C−1)の溶液を得た。得られたアルカリ可溶性樹脂(C−1)のアセトン溶液に水を加え再沈精製し、次いで石油エーテルにて再沈精製し、真空乾燥し、アルカリ可溶性樹脂(C−1)(239g)を得た。重量平均分子量は10000であり、酸価は91mgKOH/gであった。
<アルカリ可溶性樹脂(F−1)の合成>
温度計、撹拌機、加熱装置を備えた内容量300mLのガラス製フラスコに、アルカリ可溶性樹脂(C−1)(100g)、MOI(66.8g)、DBTDL(0.27g)、BHT(3.3g)及びアセトン(100g)を仕込み、撹拌しながら、30℃で18時間重合させ、アルカリ可溶性樹脂(F−1)の溶液を得た。アルカリ可溶性樹脂(F−1)の重量平均分子量は17100であった。得られたアルカリ可溶性樹脂(F−1)のアセトン溶液に水を加え再沈精製し、次いで石油エーテルにて再沈精製し、真空乾燥し、アルカリ可溶性樹脂(F−1)の163gを得た。酸価は55mgKOH/g、1分子中のエチレン性二重結合の数は22個である。
<レジスト組成物の評価>
表3に示す割合(質量部)で、含フッ素樹脂(A)、含フッ素樹脂(R)、光酸発生剤(B)、アルカリ可溶性樹脂(C)、酸架橋剤(D)、シランカップリング剤(I)、希釈剤(J)を配合してネガ型レジスト組成物を得た。
完全に現像できたものを○、現像されない部分があったものを×と記載した。
塗膜外観が良好なものを○、塗膜が白く濁る、塗膜に気泡跡が残る、塗膜に放射状の筋が残る、膜厚が均一でない等の塗膜外観が損なわれているものを×と記載した。
JIS K 5400記載の碁盤目テープ法により評価した。塗膜をカッターにて、2mm間隔でます目の数が25個となるように、碁盤目状に傷を付けた。次に粘着テープを貼り、剥がした後の塗膜の付着状態を目視により、ます目が剥がれなかったものを○、ます目が殆ど剥がれたものを×として評価した。
撥水撥油性は、ガラス基材に形成された塗膜表面の水及びキシレンの接触角(度)により評価した。接触角とは、固体と液体が接触する点における液体表面に対する接線と固体表面がなす角で、液体を含む方の角度で定義した。この角度が大きいほど塗膜の撥水撥油性が優れることを意味する。水の接触角80度以上を○、80度未満を×と表記した。キシレンの接触角30度以上を○、30度未満を×と表記した。
Claims (8)
- 式1で表される単量体から形成される単量体単位を有し、フッ素原子含有率が7〜35質量%である含フッ素樹脂(A)及び波長100〜600nmの光に反応する感光性成分を含むレジスト組成物であって、組成物の全固形分に対する含フッ素樹脂(A)の割合は0.1〜30質量%であることを特徴とするレジスト組成物。
CH2=CH(R1)COOXRf ・・・式1
式中、R1は、水素原子、メチル基又はトリフルオロメチル基、Xは炭素数1〜6の2価のフッ素原子を含まない有機基を示し、Rfは、炭素数4〜6のパーフルオロアルキル基を示す。 - 前記感光性成分は光酸発生剤(B)と、カルボキシル基及び/又はフェノール性水酸基を有するアルカリ可溶性樹脂(C)と、酸の作用によりカルボキシル基又はフェノール性水酸基と反応し得る基を2個以上有する化合物である酸架橋剤(D)とを含む請求項1記載のレジスト組成物。
- 前記含フッ素樹脂(A)はカルボキシル基及び/又は水酸基を有する請求項2に記載の組成物。
- 前記感光性成分は光ラジカル開始剤(E)と、1分子内に酸性基及び2個以上のエチレン性二重結合を有するアルカリ可溶性樹脂(F)とを含む請求項1記載の組成物。
- 前記感光性成分は2個以上のエチレン性二重結合を有し、かつ酸性基を有しないラジカル架橋剤(G)をさらに含む請求項4に記載の組成物。
- 前記含フッ素樹脂(A)はエチレン性二重結合を有する請求項4又は5に記載の組成物。
- 前記アルカリ可溶性樹脂(F)はカルボキシル基及び/又は水酸基を有し、前記感光性成分は熱の作用によりカルボキシル基及び/又は水酸基と反応し得る基を2個以上有する化合物である熱架橋剤(H)をさらに含む請求項4〜6のいずれかに記載のレジスト組成物。
- 請求項1〜7のいずれかに記載の組成物より得られる塗膜。
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