JP5284880B2 - 光硬化性組成物およびそれを用いた絶縁性薄膜および薄膜トランジスタ - Google Patents
光硬化性組成物およびそれを用いた絶縁性薄膜および薄膜トランジスタ Download PDFInfo
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- JP5284880B2 JP5284880B2 JP2009139628A JP2009139628A JP5284880B2 JP 5284880 B2 JP5284880 B2 JP 5284880B2 JP 2009139628 A JP2009139628 A JP 2009139628A JP 2009139628 A JP2009139628 A JP 2009139628A JP 5284880 B2 JP5284880 B2 JP 5284880B2
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- Compositions Of Macromolecular Compounds (AREA)
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- Silicon Polymers (AREA)
- Formation Of Insulating Films (AREA)
- Thin Film Transistor (AREA)
Description
本発明の成分(A)について説明する。
オキシムエステル系化合物の具体例としては、1,2−オクタンジオン1−[4−(フェニルチオ)−2−(O−ベンゾイルオキシム)]、エタノン1−[9−エチル−6−(2−メチルベンゾイル)−9H−カルバゾール−3−イル]−1−(O−アセチルオキシム)等が挙げられる。
で表される、1分子中に少なくとも2個のSiH基を有する鎖状オルガノポリシロキサンが好ましい。またR13、R14は入手性、耐熱性の観点より特にメチル基であるものが好ましく、硬化物の強度が高くなるという観点より、特にフェニル基であるものが好ましい。
で表される、1分子中に少なくとも2個のSiH基を有するものをあげることができる。また中でも分子中にTまたはQ構造を有するオルガノポリシロキサンが好ましい。
上記した各種化合物(β)は単独もしくは2種以上のものを混合して用いることが可能である。
次に、本発明の成分(B)について説明する。
ここで言う変性ポリオルガノシロキサン化合物とは、シロキサン単位(Si−O−Si)および、構成元素としてC、H、N、O、Sからなる有機基Xとから構成される化合物、重合体が好ましい。
(α)1分子中にSiH基との反応性を有する炭素−炭素二重結合を1個以上有し、かつ、下記式(X1)〜(X3)で表される各構造と、フェノール性水酸基と、カルボキシル基とからなる群から選ばれる少なくとも一種を同一分子内に有する有機化合物。
化合物(α)について説明する。
化合物(β)については1分子中に少なくとも2個のSiH基を有するオルガノポリシロキサン化合物であれば特に限定されず使用することができ、例として上記にあるSiH基を有する化合物が挙げられる。
化合物(α)、(β)をヒドロシリル化反応させる場合の触媒としては、公知のヒドロシリル化触媒を用いればよい。
各化合物の反応させる割合は特に限定されないが、反応させる化合物の総アルケニル基量をA、反応させる化合物の総SiH基量をBとした場合、1≦B/A≦30であることが好ましく、更に1≦B/A≦15であることが好ましい。この値が小さい場合は、組成物中に未反応アルケニル基が残るため着色の原因となり、また大きい場合には、未反応のSiH基が多く残るため、組成物の硬化時における発泡、クラックの原因となる場合がある。
(貯蔵安定性改良剤)
本発明の硬化性組成物の保存安定性を改良する目的で、貯蔵安定性改良剤を使用することができる。貯蔵安定性改良剤としては、脂肪族不飽和結合を含有する化合物、有機リン化合物、有機イオウ化合物、窒素含有化合物、スズ系化合物、有機過酸化物等が使用でき、これらを併用してもかまわない。
本発明の硬化性組成物には、光エネルギーで硬化させる場合には、光の感度向上のおよびg線(436nm)、h線(405nm)、i線(365nm)と言われるような高波長の光に感度を持たせるために、適宜、増感剤を添加する事ができる。これら増感剤は、上記カチオン重合開始剤及び/またはラジカル重合開始剤等と併用して使用し、硬化性の調整を行うことができる。
本発明の硬化性組成物には、接着性改良剤を添加することもできる。接着性改良剤としては一般に用いられている接着剤の他、例えば種々のカップリング剤、エポキシ化合物、オキセタン化合物、フェノール樹脂、クマロン−インデン樹脂、ロジンエステル樹脂、テルペン−フェノール樹脂、α−メチルスチレン−ビニルトルエン共重合体、ポリエチルメチルスチレン、芳香族ポリイソシアネート等を挙げることができる。
硬化性組成物には特性を改質する等の目的で、種々の熱可塑性樹脂を添加することも可能である。熱可塑性樹脂としては種々のものを用いることができるが、例えば、メチルメタクリレートの単独重合体あるいはメチルメタクリレートと他モノマーとのランダム、ブロック、あるいはグラフト重合体等のポリメチルメタクリレート系樹脂(例えば日立化成社製オプトレッツ等)、ブチルアクリレートの単独重合体あるいはブチルアクリレートと他モノマーとのランダム、ブロック、あるいはグラフト重合体等のポリブチルアクリレート系樹脂等に代表されるアクリル系樹脂、ビスフェノールA、3,3,5−トリメチルシクロヘキシリデンビスフェノール等をモノマー構造として含有するポリカーボネート樹脂等のポリカーボネート系樹脂(例えば帝人社製APEC等)、ノルボルネン誘導体、ビニルモノマー等を単独あるいは共重合した樹脂、ノルボルネン誘導体を開環メタセシス重合させた樹脂、あるいはその水素添加物等のシクロオレフィン系樹脂(例えば、三井化学社製APEL、日本ゼオン社製ZEONOR、ZEONEX、JSR社製ARTON等)、エチレンとマレイミドの共重合体等のオレフィン−マレイミド系樹脂(例えば東ソー社製TI−PAS等)、ビスフェノールA、ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレン等のビスフェノール類やジエチレングリコール等のジオール類とテレフタル酸、イソフタル酸、等のフタル酸類や脂肪族ジカルボン酸類を重縮合させたポリエステル等のポリエステル系樹脂(例えば鐘紡社製O−PET等)、ポリエーテルスルホン樹脂、ポリアリレート樹脂、ポリビニルアセタール樹脂、ポリエチレン樹脂、ポリプロピレン樹脂、ポリスチレン樹脂、ポリアミド樹脂、シリコーン樹脂、フッ素樹脂等の他、天然ゴム、EPDMといったゴム状樹脂が例示されるがこれに限定されるものではない。
硬化性組成物には必要に応じて充填材を添加してもよい。充填材としては各種のものが用いられるが、例えば、石英、ヒュームシリカ、沈降性シリカ、無水ケイ酸、溶融シリカ、結晶性シリカ、超微粉無定型シリカ等のシリカ系充填材、窒化ケイ素、銀粉、アルミナ、水酸化アルミニウム、酸化チタン、ガラス繊維、炭素繊維、マイカ、カーボンブラック、グラファイト、ケイソウ土、白土、クレー、タルク、炭酸カルシウム、炭酸マグネシウム、硫酸バリウム、無機バルーン等の無機充填材をはじめとして、エポキシ系等の従来の封止材の充填材として一般に使用或いは/及び提案されている充填材等を挙げることができる。
本発明の硬化性組成物には老化防止剤を添加してもよい。老化防止剤としては、ヒンダートフェノール系等一般に用いられている老化防止剤の他、クエン酸やリン酸、硫黄系老化防止剤等が挙げられる。ヒンダートフェノール系老化防止剤としては、チバスペシャリティーケミカルズ社から入手できるイルガノックス1010をはじめとして、各種のものが用いられる。
本発明の硬化性組成物にはラジカル禁止剤を添加してもよい。ラジカル禁止剤としては、例えば、2,6−ジ−t−ブチル−3−メチルフェノール(BHT)、2,2’−メチレン−ビス(4−メチル−6−t−ブチルフェノール)、テトラキス(メチレン−3(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート)メタン等のフェノール系ラジカル禁止剤や、フェニル−β−ナフチルアミン、α−ナフチルアミン、N,N’−第二ブチル−p−フェニレンジアミン、フェノチアジン、N,N’−ジフェニル−p−フェニレンジアミン等のアミン系ラジカル禁止剤等が挙げられる。また、これらのラジカル禁止剤は単独で使用してもよく、2種以上併用してもよい。
本発明の硬化性組成物には紫外線吸収剤を添加してもよい。紫外線吸収剤としては、例えば2(2’−ヒドロキシ−3’,5’−ジ−t−ブチルフェニル)ベンゾトリアゾール、ビス(2,2,6,6−テトラメチル−4−ピペリジン)セバケート等が挙げられる。また、これらの紫外線吸収剤は単独で使用してもよく、2種以上併用してもよい。
本発明の硬化性組成物に使用される、変性ポリオルガノシロキサン化合物が高粘度である場合、溶剤に溶解して用いることも可能である。使用できる溶剤は特に限定されるものではなく、具体的に例示すれば、ベンゼン、トルエン、ヘキサン、ヘプタン等の炭化水素系溶媒、テトラヒドロフラン、1,4−ジオキサン、1,3−ジオキソラン、ジエチルエーテル等のエーテル系溶媒、アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等のケトン系溶媒、プロピレングリコール−1−モノメチルエーテル−2−アセテート(PGMEA)、エチレングリコールジエチルエーテル等のグリコール系溶剤、クロロホルム、塩化メチレン、1,2−ジクロロエタン等のハロゲン系溶媒を好適に用いることができる。
本発明の硬化性組成物には、その他、着色剤、離型剤、難燃剤、難燃助剤、界面活性剤、消泡剤、乳化剤、レベリング剤、はじき防止剤、アンチモン−ビスマス等のイオントラップ剤、チクソ性付与剤、粘着性付与剤、保存安定改良剤、オゾン劣化防止剤、光安定剤、増粘剤、可塑剤、反応性希釈剤、酸化防止剤、熱安定化剤、導電性付与剤、帯電防止剤、放射線遮断剤、核剤、リン系過酸化物分解剤、滑剤、顔料、金属不活性化剤、熱伝導性付与剤、物性調整剤等を本発明の目的および効果を損なわない範囲において添加することができる。
本発明の組成物を用いた薄膜でコンタクトホール形成などの目的よりパターン形成する場合には、通常のレジスト材料の現像方法と同様の方法で行うことができ特に限定されるものではない。感光させるための光源としては、使用する重合開始剤や増感剤の吸収波長を発光する光源を使用すればよく、通常200〜450nmの範囲の波長を含む光源、例えば、高圧水銀ランプ、超高圧水銀ランプ、メタルハライドランプ、ハイパワーメタルハライドランプ、キセノンランプ、カーボンアークランプ、発光ダイオードなどを使用できる。
本発明の硬化性組成物は、フォトリソグラフィーにより微細なコンタクトホール等の形成も簡便に形成でき、かつ得られる硬化物は薄膜での絶縁性にも優れていることより、高い絶縁性が要求される電子部品、例えば薄膜トランジスタのパッシベーション膜、ゲート絶縁膜に適用することができる。
実施例および比較例で得られた硬化性組成物をガラス板に厚み約50μmとなるようコートしたものを、ポストベイクとして150℃30分間循環型熱風オーブンで加熱したガラス基板上サンプルについて、上記と同様の循環型熱風オーブン200℃24時間保存し、耐熱試験を実施した。耐熱性試験前後の組成物塗膜外観および光線透過率を測定し耐熱透明性を評価した。ここでの光線透過率は、(株)日立製作所製U−3300を用いて、スキャンスピード300nm/minの条件で測定した。
実施例および比較例で得られた硬化性組成物を得られた組成物をガラス板(50×100×0.7mm)にスピンコートにより塗布し、塗面を部分的に簡易マスクを設けてコンベア型露光装置(高圧水銀ランプ、フュージョン製LH6)にて積算光量200mJ/cm2露光した。
500mL四つ口フラスコにトルエン100g、1,3,5,7−テトラメチルシクロテトラシロキサン57.49gを入れ、気相部を窒素置換した後、内温105℃で加熱、攪拌した。ジアリルイソシアヌル酸10.0g、1,4−ジオキサン70.0g及び白金ビニルシロキサン錯体のキシレン溶液(白金として3wt%含有)0.0186gの混合液を30分かけて滴下した。
500mL四つ口フラスコにトルエン175g、1,3,5,7−テトラメチルシクロテトラシロキサン86.23gを入れ、気相部を窒素置換した後、内温105℃で加熱、攪拌した。ジアリルイソシアヌル酸7.5g、トリアリルイソシアヌレート5.95g、1,4−ジオキサン70.0g及び白金ビニルシロキサン錯体のキシレン溶液(白金として3wt%含有)0.0280gの混合液を30分かけて滴下した。
合成実施例1得られたポリシロキサン系化合物A1gに、光硬化性エポキシ化合物(ダイセル化学、製品名:セロキサイド2021P)1gにカチオン重合開始剤(ローディア、製品名:RHODORSIL PI2074)0.01g、プロピレングリコールモノメチルエーテルアセテート(溶剤、PGMEA)8gを加え樹脂組成物とした。
合成実施例2得られたポリシロキサン系化合物A1gに、光硬化性エポキシ化合物(ダイセル化学、製品名:セロキサイド2021P)1gにカチオン重合開始剤(ローディア、製品名:RHODORSIL PI2074)0.01g、プロピレングリコールモノメチルエーテルアセテート(溶剤、PGMEA)8gを加え樹脂組成物とした。
合成実施例1得られたポリシロキサン系化合物A1gに、ジトリメチロールプロパンテトラアクリレート(新中村化学工業製、製品名:AD−TMP)1gにラジカル重合開始剤(チバスペシャリティケミカルズ、製品名:DAROCURE1173)0.04g、プロピレングリコールモノメチルエーテルアセテート(溶剤、PGMEA)8gを加え樹脂組成物とした。
合成実施例1得られたポリシロキサン系化合物A1gに、ビニルトリメトキシシラン(信越化学製、製品名:LS−815)1gにカチオン重合開始剤(ローディア、製品名:RHODORSIL PI2074)0.02g、プロピレングリコールモノメチルエーテルアセテート(溶剤、PGMEA)8gを加え樹脂組成物とした。
光硬化性エポキシ化合物(ダイセル化学、製品名:セロキサイド2021P)1gにカチオン重合開始剤(ローディア、製品名:RHODORSIL PI2074)0.01g、PGMEA4.0gを加え樹脂組成物とした。
ビニルトリメトキシシラン(信越化学製、製品名:LS−815)1gにカチオン重合開始剤(ローディア、製品名:RHODORSIL PI2074)0.02g、プロピレングリコールモノメチルエーテルアセテート(溶剤、PGMEA)8gを加え樹脂組成物とした。
Claims (5)
- (A)感光性樹脂、(B)下記式(X1)〜(X3)
感光性樹脂(A)が、脂環式エポキシ基を有する化合物またはオキセタン化合物を含有する硬化性樹脂、
脂環式エポキシ基を有する化合物と光カチオン重合開始剤からなる光硬化性樹脂、
アクリレート化合物を含有する感光性樹脂、
メタクリロイル基および/またはアクリロイル基を有する化合物と光ラジカル重合開始剤からなる光硬化性樹脂、
アルコキシシラン化合物を含有する感光性樹脂、
アルコキシシリル基を有する化合物と光カチオン重合開始剤からなる感光性樹脂、
SiH基を有する化合物と光カチオン重合開始剤からなる光硬化性樹脂、または、
光硬化性マレイミド樹脂
である硬化性組成物。 - (A)感光性樹脂、(B)(α)アルケニル基を有しかつ下記式(X1)〜(X3)
感光性樹脂(A)が、脂環式エポキシ基を有する化合物またはオキセタン化合物を含有する硬化性樹脂、
脂環式エポキシ基を有する化合物と光カチオン重合開始剤からなる光硬化性樹脂、
アクリレート化合物を含有する感光性樹脂、
メタクリロイル基および/またはアクリロイル基を有する化合物と光ラジカル重合開始剤からなる光硬化性樹脂、
アルコキシシラン化合物を含有する感光性樹脂、
アルコキシシリル基を有する化合物と光カチオン重合開始剤からなる感光性樹脂、
SiH基を有する化合物と光カチオン重合開始剤からなる光硬化性樹脂、または、
光硬化性マレイミド樹脂
である硬化性組成物。 - 請求項1または2に記載の硬化性組成物を用いて得られる絶縁膜。
- 請求項3に記載の絶縁膜を半導体層のパッシベーション膜とすることを特徴とする薄膜トランジスタ。
- 請求項3に記載の絶縁膜をゲート絶縁膜とすることを特徴とする薄膜トランジスタ。
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