JPS6024543A - Photosensitive silicone resin composition - Google Patents
Photosensitive silicone resin compositionInfo
- Publication number
- JPS6024543A JPS6024543A JP13217783A JP13217783A JPS6024543A JP S6024543 A JPS6024543 A JP S6024543A JP 13217783 A JP13217783 A JP 13217783A JP 13217783 A JP13217783 A JP 13217783A JP S6024543 A JPS6024543 A JP S6024543A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- photosensitive
- polysiloxane
- resin composition
- aromatic
- 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
Links
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
Abstract
Description
【発明の詳細な説明】 本発明は新規な感光性シリコーン樹脂組成物に関する。[Detailed description of the invention] The present invention relates to a novel photosensitive silicone resin composition.
感光性シリコーン樹脂の製造法としては１）水酸基を有
するポリシロキサ／にメタクリル基を有するアルコキシ
シランを反応させる方法（特開昭４９−３９２００号公
報）
２）水素を有するボリシ日キサンにアリルメタクリレー
ト等の化合物を付加反応させる方法（特開昭５２−３５
７１９号公報）などの他、ポリシロキサンに感光基を導
入する種々の方法が知られている。しかし、これらのポ
リシロキサンに感光基を導入する方法では、その製造法
が非常釦けん雑であるという欠点を有していた。Methods for producing photosensitive silicone resin include 1) a method in which polysiloxane having a hydroxyl group is reacted with an alkoxysilane having a methacrylic group (JP-A-49-39200); 2) a method in which polysiloxane having a hydroxyl group is reacted with an alkoxysilane having a methacrylic group (JP-A-49-39200); Method for addition reaction of compounds (JP-A-52-35
719), and various other methods are known for introducing photosensitive groups into polysiloxanes. However, these methods of introducing photosensitive groups into polysiloxanes have the disadvantage that their production methods are extremely complicated.
本発明者らは、この欠点に鑑み上記のように感光基を導
入した樹脂を用いることなく容易に製造可能な感光性樹
脂組成物を得る目的で検討を重ねた結果１本発明に至っ
た。In view of this drawback, the present inventors have conducted repeated studies with the aim of obtaining a photosensitive resin composition that can be easily produced without using a resin into which a photosensitive group has been introduced as described above, and as a result, they have arrived at the present invention.
すなわち本発明は。That is, the present invention.
一般式 （ａｌ ５ｉＸａ （ｂｌ 几Ｓ ｉＸｓ （
ｃｌ ＆ Ｓ ｉＸｓまたは（ｄ） Ｒ５８ｉＸ （こ
こでＸＦｉ加水分解可能な基を表わし、Ｒは一価の炭化
水素基を表わす。）で示されるシラン化合物のうち少な
くとも１つを加水分解′した後重縮合して得られるポリ
シロキサン（Ａ）と（Ｂ）芳香族アジド化合物および／
または芳香族スルホニルアジド化合物を含有してなる感
光性シリコーン樹脂組成物に関する。General formula (al 5iXa (bl 几S iXs (
After hydrolyzing at least one of the silane compounds represented by cl & Si Polysiloxane (A) obtained by condensation and (B) aromatic azide compound and/or
Or it relates to a photosensitive silicone resin composition containing an aromatic sulfonyl azide compound.
本発明によれば、ベースレジンとなる上記のボリシロキ
サンと、感光性化合物である芳香族アジド化合物および
／ｌたは芳香族スルホニルアジド化合物を混合すること
により容易に感光性シリコーン樹脂組成物を得ることが
できる。According to the present invention, a photosensitive silicone resin composition can be easily obtained by mixing the above-mentioned polysiloxane serving as a base resin with an aromatic azide compound and/or an aromatic sulfonyl azide compound as a photosensitive compound. be able to.
以下１本発明の詳細な説明する。The present invention will be explained in detail below.
本発明の感光性シリコ−ｙ樹脂組成物に用いられるポリ
シロキサンは、前記のシラン化合物を加水分解した後重
縮合することにより、得られるもので、すで忙公知の化
合物であり、公知の方法によって製造される。前記した
シラン化合物の一般式において加水分解可能な基である
Ｘは１例えば塩素、アルコキシ基などであシ、−価の炭
化水素基テするＲは９例えばメチル基、エチル基環ノー
価のアルキル基、フェニル基、置換フェニル基等の一価
のアリール基などであシ、これらはすべて同一であって
も相違して−もよい。The polysiloxane used in the photosensitive silico-y resin composition of the present invention is a well-known compound obtained by hydrolyzing the above-mentioned silane compound and then polycondensing it. Manufactured by. In the general formula of the silane compound described above, X, which is a hydrolyzable group, is 1, such as chlorine or an alkoxy group, and R, which is a -valent hydrocarbon group, is 9, such as methyl group, ethyl group, or a non-valent alkyl group. A phenyl group, a monovalent aryl group such as a substituted phenyl group, etc., and these may all be the same or different.
一般式（ａｌで示されるシラン化合物の例としては。Examples of silane compounds represented by the general formula (al) are:
５ｉＣ１４＋ ８４（ＯＣＨｓ）４． Ｓｊ（ＯＣｇＨ
ｓ）４等があシ。5iC14+ 84 (OCHs)4. Sj(OCgH
s) 4th prize.
ｔｂ３で示されるシラン化合物の例としては、（：Ｈｇ
８ ｔ Ｃｌｓ ＋ＣＨｓ８ｉ （ＯＣＨｓ ）ｓ
、 ＣＨａＳｉ（ＱＣ鵞Ｈｓ ）ｓ 、◇）−８ｊＣ／
ｊ。Examples of the silane compound represented by tb3 include (:Hg
8t Cls +CHs8i (OCHs)s
, CHaSi(QC鵞Hs )s , ◇)-8jC/
j.
一般式（Ｃ１または（ｄｌで示されるシラン化合物は一
般式（ｂ）で示される基の数を変え−たものがあげられ
る。Silane compounds represented by the general formula (C1 or (dl) include those represented by the general formula (b) with a different number of groups.
これらのシラン化合物を二種以上用いる場合には、加水
分解をする際の混合比および置換基凡の種類を変えると
とＫよシ、得られるポリシロキサンおよび感光性樹脂組
成物の特性を調整することが可能である。すなわち、加
水分解において上記の一般式（ａ）ｆたＪｄｌｂ）で示
される４官能酸分または３官能酸分を多く用いると、ポ
リシロキサンおよび感光性樹脂組成物は、耐熱性忙すぐ
れ、剛直なものとなる。When two or more of these silane compounds are used, the properties of the resulting polysiloxane and photosensitive resin composition can be adjusted by changing the mixing ratio and types of substituents during hydrolysis. Is possible. That is, when a large amount of the tetrafunctional acid or trifunctional acid represented by the above general formula (a) f or Jdlb) is used in hydrolysis, the polysiloxane and photosensitive resin composition have excellent heat resistance and rigidity. Become something.
また、上記の一般式（Ｃ）ｔたは（ｄｌで示される２官
能酸分またＦｉ１官能成分を多く用いると可とう性にす
ぐれたポリシロキサンおよび感光性樹脂組成物が得られ
る。Further, when a large amount of the bifunctional acid component represented by the above general formula (C) t or (dl) or the Fi1 functional component is used, a polysiloxane and a photosensitive resin composition with excellent flexibility can be obtained.
また９本発明の感光性シリコーン樹脂組成物に用いられ
る感光性化合物である芳香族アジド化合物および／また
は芳香族スルホニルアジド化合物は光照射によシ活性種
ナイトレンを生成し、この活性種は二量化、二重結合へ
の付加、水素引き抜き反応などを起こすことが知られて
いる。従ってポリシロキサン中忙添加されたこれらの感
光性化合物は上記反応を経由して、その光照射部と光非
照射部に現像液に対する溶解性の差異をもたらし。Furthermore, the aromatic azide compound and/or the aromatic sulfonyl azide compound, which are the photosensitive compounds used in the photosensitive silicone resin composition of the present invention, generate an active species nitrene upon irradiation with light, and this active species dimerizes. , addition to double bonds, and hydrogen abstraction reactions. Therefore, these photosensitive compounds added to the polysiloxane undergo the above-mentioned reaction to cause a difference in solubility in the developer between the light-irradiated area and the non-light-irradiated area.
パターン形成が可能となる。Pattern formation becomes possible.
本発明釦用すられる芳香族アジド化合物としては例えば ＨＨＨＨＨＨ 等のモノアジド化合物。Examples of the aromatic azide compounds used in the button of the present invention include: HHHHHH Monoazide compounds such as.
Ｃ山
等のビスアジド化合物などがある。また、芳香族スルホ
ニルアジド化合物としては９例えば等のモノスルホニル
アジド化合物
しＥ リ
等のビススルホニルアジド化合物などがある。これらの
感光性化合物は、単独でまたは二種以上を併用して用い
ることができる。There are bisazide compounds such as C mountain. Examples of aromatic sulfonyl azide compounds include monosulfonyl azide compounds such as 9 and bissulfonyl azide compounds such as E. These photosensitive compounds can be used alone or in combination of two or more.
本発明の感光性シリコーン樹脂組成物は１通常ポリシロ
キサンと感光性化合物を適当な有機溶媒に溶解した状態
で使用されるが、この場合に用いる溶媒としては、ポリ
シロキサンおよび感光性化合物のいずれをも溶解する溶
媒が用いられる。The photosensitive silicone resin composition of the present invention is usually used in a state in which polysiloxane and a photosensitive compound are dissolved in a suitable organic solvent. A solvent that also dissolves is used.
まだ１本発明の感光性シリコーン樹脂組成物には種々の
増感剤を併用することも可能である。It is also possible to use various sensitizers in combination with the photosensitive silicone resin composition of the present invention.
増感剤は感光性化合物の感光波長域をひろげたり、感光
性化合物圧光エネルギーを効率よく与えるなどして感光
感度の向上をはかるものであシ１本発明においては９例
えばぺ／ジインまたはその誘導体、ベンゾインメチルエ
ーテル等ノペンゾインエーテル類、ベンジルとその誘導
体、アリールジアゾニウム塩、アントラキノンとその誘
導体、アセトフェノンまだはその誘導体、ジフェニルジ
スルフィド等のイオウ化合物、ベンゾフェノン又はその
誘導体などが使用可能であシ、これらは一種または二種
以上が用いられる。The sensitizer is used to improve the photosensitivity by expanding the sensitive wavelength range of the photosensitive compound or efficiently imparting pressure energy to the photosensitive compound. Derivatives, nopenzoin ethers such as benzoin methyl ether, benzyl and its derivatives, aryl diazonium salts, anthraquinone and its derivatives, acetophenone and its derivatives, sulfur compounds such as diphenyl disulfide, benzophenone or its derivatives, etc. can be used. One or more of these may be used.
また、必要に応じてシランカップリン剤などの接着助剤
を用いてもよい。Further, an adhesion aid such as a silane coupling agent may be used as necessary.
本発明における感光性シリコーン樹脂組成物の組成とし
ては、ポリシロキサン１００重量部に対して、感光性化
合物は、好ましくは１〜５０重量部、よシ好ましくけ５
〜３０重量部の範囲で用いられる。感光性化合物が多す
ぎると保存中に感光性化合物が析出したり、感光性化合
物が少なすぎると光反応後、光照射部と光非照射部との
現像液に対する溶解性の差が小さくなりパターン形成能
が低下する傾向がある。In the composition of the photosensitive silicone resin composition in the present invention, the photosensitive compound is preferably 1 to 50 parts by weight, preferably 5 to 50 parts by weight, based on 100 parts by weight of polysiloxane.
It is used in a range of 30 parts by weight. If there is too much photosensitive compound, the photosensitive compound will precipitate during storage, and if there is too little photosensitive compound, after the photoreaction, the difference in solubility in the developing solution between the light-irradiated area and the non-light-irradiated area will become smaller, resulting in a pattern failure. Formation ability tends to decrease.
本発明になる感光性シリコーン樹脂組成物は上記した様
な組成で有機溶媒溶液とし、適当な方法で基材に塗布し
た後、溶媒を乾燥し光照射を行ない、ついで有機溶媒、
希アルカリ溶液等の現像液を用いてパターンを形成する
ことができる。The photosensitive silicone resin composition of the present invention is made into an organic solvent solution with the above-mentioned composition, applied to a substrate by an appropriate method, dried the solvent, and irradiated with light.
A pattern can be formed using a developer such as a dilute alkaline solution.
本発明を実施例より説明する。The present invention will be explained by examples.
実施例１
ポリシロキサンの合成は特開昭５０−１１１１９７号公
報の実施例１０条件に従って行なった。メチルトリクロ
ロ７ラン１モルとジメチルジクロロ７ラン１モルの混合
物を冷水中に添加して加水分解して得られたゲル状物を
水洗した後水酸化カリウム６モルを加えて全体を溶解さ
せ、カリウムシラル−トを４０重量％含む水溶液を得た
。Example 1 Polysiloxane was synthesized according to the conditions of Example 10 of JP-A-50-111197. A mixture of 1 mole of methyltrichloro-7rane and 1 mole of dimethyldichloro-7rane was added to cold water and hydrolyzed. The gel-like substance obtained was washed with water, and then 6 moles of potassium hydroxide was added to dissolve the whole. An aqueous solution containing 40% by weight of syralate was obtained.
このシラル−ト水溶液とメチルイソブチルケトン６００
−とを還流冷却管および滴下ロート付反応器に仕込みシ
ラル−トの水溶液層（下層）とメチルイソブチルケトン
層（上層）の２層を形成させた。This syralate aqueous solution and methyl isobutyl ketone 600
- and were charged into a reactor equipped with a reflux condenser and a dropping funnel to form two layers: a syralate aqueous solution layer (lower layer) and a methyl isobutyl ketone layer (upper layer).
つぎにこの２層がくずれない程度に加熱して還流させな
がら９滴下ロートより無水酢酸３モルを上層に滴下し、
全量滴下後さらに２時間還流させ反応を完結させた。こ
うして得られた上層をメタノール中に注ぎポリシロキサ
ンを得た。Next, while heating and refluxing to an extent that these two layers do not collapse, 3 moles of acetic anhydride are dropped into the upper layer from a 9-dropping funnel.
After dropping the entire amount, the mixture was further refluxed for 2 hours to complete the reaction. The upper layer thus obtained was poured into methanol to obtain polysiloxane.
こうして得られたポリシロキサン（重量平均分子量１０
万）１０？に３，３′−ジアジドジフェニルスルホン１
？を添加し、トルエン１００ Ｆ［溶解して感光性シリ
コーン樹脂組成物を作製した。The polysiloxane thus obtained (weight average molecular weight 10
10,000) 10? 3,3'-diazide diphenyl sulfone 1
? was added and dissolved in toluene at 100 F [to prepare a photosensitive silicone resin composition.
この組成物をシリコーンウェーハ上にスピンナーで膜厚
１μｍに塗布し、塗布後１２０℃で２０分間乾燥し９石
英マスク（大日本印刷株式会社製ＤＮＰファインライン
テストパターン１）を介シてＸｅ−Ｈｇ灯によＪ） ５
０ ｍＷ／ｃｍ’で光照射を行なった。その後希アルカ
リ水溶液（５％のか性カリ溶液）で１０分間現像した結
果３μｍのラインとスペースを有する非常に良好なパタ
ーンが得られた。This composition was applied to a film thickness of 1 μm on a silicone wafer using a spinner, dried at 120°C for 20 minutes after application, and then exposed to Xe-H Light J) 5
Light irradiation was performed at 0 mW/cm'. Thereafter, the film was developed with a dilute aqueous alkaline solution (5% caustic potash solution) for 10 minutes, and as a result, a very good pattern with 3 μm lines and spaces was obtained.
実施例２
米国特許第３．０１７．３８５号明細書の実施例１に従
いジフェニルジェトキシシラン０．１モル、フェニルト
リエトキシシラン０．８９モル、トリフェニルエトキシ
シラン０．０１モルをベンゼン５００ｄＶｃ溶解し、還
流しながら、水酸化テトラメチルアンモニウム水溶液を
滴下して加水分解を行なった。Example 2 According to Example 1 of U.S. Pat. While refluxing, an aqueous tetramethylammonium hydroxide solution was added dropwise to perform hydrolysis.
こうして得られた加水分解物を実施例１と同様にして重
縮合してポリシロキサンを合成し、得られたポリシロキ
サ／（重量平均分子着１万）１０エチル３ｇ−を添加し
、シクロヘキ゛ナノン１０（１に溶解して感光性シリコ
ーン樹脂組成物を作製した。The thus obtained hydrolyzate was polycondensed in the same manner as in Example 1 to synthesize polysiloxane, and 3 g of the obtained polysiloxane/(weight average molecular weight: 10,000) 10 ethyl was added, and cyclohexanone 10 (10,000 ml) was added. A photosensitive silicone resin composition was prepared.
この組成物を用いて実施例１と同様の処理を１１なった
ところ、３＃ｒ’Ｓラインとスペースを有する良好なパ
ターンが得られた。When this composition was subjected to the same treatment as in Example 1 for 11 times, a good pattern having 3#r'S lines and spaces was obtained.
本発明によれば、ポリクロキサンと感光性化合物を混合
するだけで容易に感光性シ１）コーン樹ｎ旨組成物を作
製することがでへ、ｔだこの感光性／リコーン樹脂組成
物は、実施例にも示したＪｌす３μｍのラインとスペー
スを有する良好なノ（ターンが得られるため、を子部品
の回路形成用レジスト等の用途にも使用することも可能
である。According to the present invention, it is possible to easily prepare a photosensitive resin composition by simply mixing polycloxane and a photosensitive compound. As shown in the example, a good turn with a line and space of 3 μm can be obtained, so it can also be used as a resist for forming circuits of sub-components.
Claims (1)
（ｅ） Ｒ＊８ｉＸ＊また＃′１（ｄｌ几５ｓｉＸ（こ
こでＸは加水分解可能な基を表わし、几は一価の炭化水
素基を表わす。）で示されるシラン化合物のうち少なく
とも１つを加水分解した後重縮合して得られるポリシロ
キサン囚ならびＫ（Ｂ）芳香族アジド化合物および／ｆ
たけ芳香族スルホニルアジド化合物を含有してなる感光
性シリコーン樹脂組成物。1. General formula (al 5iXi (b) R81Xs
(e) At least one silane compound represented by R*8iX* or #'1 (dl几5siX (where X represents a hydrolyzable group, and 几 represents a monovalent hydrocarbon group). polysiloxane compound obtained by hydrolyzing and then polycondensing K(B) aromatic azide compound and /f
A photosensitive silicone resin composition containing an aromatic sulfonyl azide compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58132177A JPH0656491B2 (en) | 1983-07-20 | 1983-07-20 | Photosensitive silicone resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58132177A JPH0656491B2 (en) | 1983-07-20 | 1983-07-20 | Photosensitive silicone resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6024543A true JPS6024543A (en) | 1985-02-07 |
| JPH0656491B2 JPH0656491B2 (en) | 1994-07-27 |
Family
ID=15075173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58132177A Expired - Lifetime JPH0656491B2 (en) | 1983-07-20 | 1983-07-20 | Photosensitive silicone resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0656491B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06240143A (en) * | 1993-02-12 | 1994-08-30 | Fuji Xerox Co Ltd | Inorganic-organic composite material and its production |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51127801A (en) * | 1975-04-24 | 1976-11-08 | Toshiba Silicone | Photoosensitive composition for dry lithographic printing |
| JPS5417015A (en) * | 1977-07-06 | 1979-02-08 | Nec Corp | Radiation sensitive composite |
| JPS5896654A (en) * | 1981-12-02 | 1983-06-08 | Hitachi Chem Co Ltd | Photosensitive silicon resin composition |
| JPS59196446A (en) * | 1983-04-22 | 1984-11-07 | Toshiba Corp | Defect recognizing device |
| JPS59198446A (en) * | 1983-04-26 | 1984-11-10 | Nippon Telegr & Teleph Corp <Ntt> | Photosensitive resin composition and using method thereof |
-
1983
- 1983-07-20 JP JP58132177A patent/JPH0656491B2/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51127801A (en) * | 1975-04-24 | 1976-11-08 | Toshiba Silicone | Photoosensitive composition for dry lithographic printing |
| JPS5417015A (en) * | 1977-07-06 | 1979-02-08 | Nec Corp | Radiation sensitive composite |
| JPS5896654A (en) * | 1981-12-02 | 1983-06-08 | Hitachi Chem Co Ltd | Photosensitive silicon resin composition |
| JPS59196446A (en) * | 1983-04-22 | 1984-11-07 | Toshiba Corp | Defect recognizing device |
| JPS59198446A (en) * | 1983-04-26 | 1984-11-10 | Nippon Telegr & Teleph Corp <Ntt> | Photosensitive resin composition and using method thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06240143A (en) * | 1993-02-12 | 1994-08-30 | Fuji Xerox Co Ltd | Inorganic-organic composite material and its production |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0656491B2 (en) | 1994-07-27 |
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