JP2525568B2 - Photosolubilizing composition - Google Patents
Photosolubilizing compositionInfo
- Publication number
- JP2525568B2 JP2525568B2 JP60007087A JP708785A JP2525568B2 JP 2525568 B2 JP2525568 B2 JP 2525568B2 JP 60007087 A JP60007087 A JP 60007087A JP 708785 A JP708785 A JP 708785A JP 2525568 B2 JP2525568 B2 JP 2525568B2
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- Japan
- Prior art keywords
- group
- compound
- substituted
- acid
- present
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Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Materials For Photolithography (AREA)
Description
【発明の詳細な説明】 「産業上の利用分野」 本発明は、平版印刷版、多色印刷の校正刷、オーバー
ヘツドプロジエクター用図面、IC回路、ホトマスクの製
造に適する光可溶化組成物に関する。更に詳しくは、
（ａ）酸により分解し得るシリルエーテル基を少なくと
も１個有する化合物、及び（ｂ）活性光線の照射によ
り、酸を発生し得る化合物、を含有する新規な光可溶化
組成物に関する。TECHNICAL FIELD The present invention relates to a photosolubilizing composition suitable for producing lithographic printing plates, proofs for multicolor printing, drawings for overhead projectors, IC circuits, and photomasks. . For more details,
The present invention relates to a novel photosolubilizing composition containing (a) a compound having at least one silyl ether group capable of being decomposed by an acid, and (b) a compound capable of generating an acid upon irradiation with an actinic ray.
「従来の技術」 活性光線により可溶化する。いわゆるポジチブに作用
する感光性物質としては、従来オルトキノンジアジド化
合物が知られており、実際平版印刷版、ホトレジスト等
に広く利用されてきた。このようなオルトキノンジアジ
ド化合物としては、例えば米国特許第2,766,118号、同
第2,767,092号、同第2,772,972号、同第2,859,112号、
同第2,907,665号、同第3,046,110号、同第3,046,111
号、同第3,046,115号、同第3,046,118号、同第3,046,11
9号、同第3,046,120号、同第3,046,121号、同第3,046,1
22号、同第3,046,123号、同第3,061,430号、同第3,102,
809号、同第3,106,465号、同第3,635,709号、同第3,64
7,443号の各明細書をはじめ、多数の刊行物に記されて
いる。"Prior art" Soluble by actinic rays. As a so-called positively acting photosensitive substance, an orthoquinonediazide compound has been conventionally known, and in fact, it has been widely used for lithographic printing plates, photoresists and the like. Such orthoquinone diazide compounds, for example, U.S. Pat.Nos. 2,766,118, 2,767,092, 2,772,972, 2,859,112,
No. 2,907,665, No. 3,046,110, No. 3,046,111
No. 3,046,115, No. 3,046,118, No. 3,046,11
No. 9, No. 3,046,120, No. 3,046,121, No. 3,046,1
No. 22, No. 3,046,123, No. 3,061,430, No. 3,102,
No. 809, No. 3,106,465, No. 3,635,709, No. 3,64
It is described in a number of publications, including the specifications of 7,443.
これらのオルトキノンジアジド化合物は、活性光線の
照射により分解を起こして５員環のカルボン酸を生じ、
アルカリ可溶性となることを利用したものであるが、い
ずれも感光性が不十分であるという欠点を有する。これ
は、オルトキノンジアジド化合物の場合、本質的に量子
収率が１を越えないということに由来するものである。These orthoquinonediazide compounds are decomposed by irradiation with actinic rays to generate 5-membered carboxylic acid,
Although the fact that it becomes alkali-soluble is utilized, both of them have the drawback of insufficient photosensitivity. This is derived from the fact that in the case of an orthoquinonediazide compound, the quantum yield does not essentially exceed 1.
オルトキノンジアジド化合物を含む感光性組成物の感
光性を高める方法については、今までいろいろと試みら
れてきたが、現像時の現像許容性を保持したまま感光性
を高めることは非常に困難であつた。例えば、このよう
な試みの例として、特公昭48−12242号、特開昭52−401
25号、米国特許第4,307,173号などの明細書に記載され
た内容を挙げることができる。Various methods have been tried until now for increasing the photosensitivity of a photosensitive composition containing an orthoquinonediazide compound, but it has been extremely difficult to increase the photosensitivity while maintaining the development acceptability during development. . For example, as an example of such an attempt, Japanese Patent Publication No. 48-12242 and Japanese Unexamined Patent Publication No. 52-401.
25, U.S. Pat. No. 4,307,173, and the like.
また最近、オルトキノンジアジド化合物を用いずにポ
ジチブに作用させる感光性組成物に関して、いくつかの
提案がされている。その１つとして、例えば特公昭56−
2696号の明細書に記載されているオルトニトロカルビノ
ールエステル基を有するポリマー化合物が挙げられる。
しかし、この場合も、オルトキノンジアジドの場合と同
じ理由で感光性が十分とは言えない。また、これとは別
に接触作用により活性化される感光系を使用し、感光性
を高める方法として、光分解で生成する酸によつて第２
の反応を生起させ、それにより露光域を可溶化する公知
の原理が適用されている。Recently, some proposals have been made on photosensitive compositions which act positively without using an orthoquinonediazide compound. As one of them, for example,
Polymer compounds having an orthonitrocarbinol ester group described in the specification of No. 2696 can be mentioned.
However, also in this case, the photosensitivity is not sufficient for the same reason as in the case of orthoquinonediazide. In addition to this, a photosensitive system activated by a contact action is used separately, and as a method for increasing the photosensitivity, the second method is to use an acid generated by photolysis.
A known principle of causing the above reaction to occur and thereby solubilizing the exposed area has been applied.
このような例として、例えば光分解により酸を発生す
る化合物と、アセタール又はＯ、Ｎ−アセタール化合物
との組合せ（特開昭48−89003号）、オルトエステル又
はアミドアセタール化合物との組合せ（特開昭51−1207
14号）、主鎖にアセタール又はケタール基を有するポリ
マーとの組合せ（特開昭53−133429号）、エノールエー
テル化合物との組合せ（特開昭55−12995号）、Ｎ−ア
シルイミノ炭酸化合物との組合せ（特開昭55−126236
号）、及び主鎖にオルトエステル基を有するポリマーと
の組合せ（特開昭56−17345号）を挙げることができ
る。これらは原理的に量子収率が１を越える為、高い感
光性を示す可能性があるが、アセタール又はＯ、Ｎ−ア
セタール化合物の場合、及び主鎖にアセタール又はケタ
ール基を有するポリマーの場合、光分解で生成する酸に
よる第２の反応の速度が遅い為、実際の使用に十分な感
光性を示さない。またオルトエステル又はアミドアセタ
ール化合物の場合及び、エノールエーテル化合物の場
合、更にＮ−アシルイミノ炭酸化合物の場合な確かに高
い感光性を示すが、経時での安定が悪く、長期に保存す
ることができない。主鎖にオルトエステル基を有するポ
リマーの場合も、同じく高感度ではあるが、現像時の現
像許容性が狭いという欠点を有する。Examples of such a combination include, for example, a combination of a compound that generates an acid by photolysis with an acetal or an O, N-acetal compound (Japanese Patent Application Laid-Open No. 48-89003), or a combination of an orthoester or an amide acetal compound (Japanese Patent Application Laid-Open No. 51-1207
No. 14), a combination with a polymer having an acetal or ketal group in the main chain (JP-A-53-133429), a combination with an enol ether compound (JP-A-55-12995), and a combination with an N-acyliminocarbonate compound. Combination (JP-A-55-126236)
No.) and a polymer having an orthoester group in the main chain (JP-A-56-17345). Since they have a quantum yield of more than 1 in principle, they may show high photosensitivity, but in the case of acetal or O, N-acetal compound, and in the case of a polymer having an acetal or ketal group in the main chain, Since the second reaction due to the acid generated by photolysis is slow, it does not exhibit sufficient photosensitivity for actual use. Further, in the case of an orthoester or amide acetal compound, and in the case of an enol ether compound, the photosensitivity is certainly high as in the case of the N-acyliminocarbonic acid compound, but the stability over time is poor and it cannot be stored for a long time. A polymer having an orthoester group in the main chain also has a high sensitivity but has a drawback that the development tolerance at the time of development is narrow.
「発明が解決しようとする問題点」 本研究の目的は、これらの問題点が解決された新規な
光可溶化組成物を提供することである。即ち高い感光性
を有し、現像時の現像許容性が広い新規な光可溶化組成
物を提供することである。"Problems to be Solved by the Invention" The purpose of the present study is to provide a novel photosolubilizing composition in which these problems are solved. That is, it is to provide a novel photosolubilizing composition having high photosensitivity and having a wide development latitude during development.
本研究の別の目的は、経時での安定性が優れ長期に保
存が可能な新規な光可溶化組成物を提供することであ
る。Another object of this study is to provide a novel photosolubilizing composition which has excellent stability over time and can be stored for a long period of time.
本研究の更に別の目的は、製造が簡便で容易に取得で
きる新規な光可溶化組成物を提供することである。Yet another object of the present study is to provide a novel photosolubilizing composition which is easy to manufacture and can be easily obtained.
「問題点を解決するための手段」 本発明者は、上記目的を達成すべく鋭意検討を加えた
結果新規な光可溶化組成物を用いることで前記目的が達
成されることを見い出し本発明に到達した。"Means for Solving Problems" The present inventor found that the above-mentioned object can be achieved by using a novel photosolubilizing composition as a result of earnest studies to achieve the above-mentioned object. Arrived
即ち本発明は、（ａ） 分子中に下記一般式（Ｉ）で
示される酸により分解し得るシリルエーテル基を少なく
とも１個有し現像液中での、その溶解度が酸の作用によ
り増大する化合物、及び Ｃ−Ｏ−Si （Ｉ） （ｂ） 下記一般式（II）あるいは（III）で示される
活性光線の照射により酸を発生し得る化合物 R1−SO2−SO2−R2 （II） 式中、R1およびR2は各々独立してアリール基あるいは
置換アリール基を表わす 式中、Ａはアリーレン基、置換アリーレン基、アルキ
レン基、置換アルキレン基、アルケニレン基、置換アル
ケニレン基を表わす。Ｒはアルキル基、置換アルキル
基、アリール基、置換アリール基を表わす。That is, the present invention provides a compound (a) having in the molecule at least one silyl ether group which can be decomposed by an acid represented by the following general formula (I) and whose solubility in a developing solution is increased by the action of an acid. , And C—O—Si (I) (b) a compound represented by the following general formula (II) or (III) capable of generating an acid upon irradiation with an actinic ray R 1 —SO 2 —SO 2 —R 2 (II ) In the formula, R 1 and R 2 each independently represent an aryl group or a substituted aryl group. In the formula, A represents an arylene group, a substituted arylene group, an alkylene group, a substituted alkylene group, an alkenylene group, or a substituted alkenylene group. R represents an alkyl group, a substituted alkyl group, an aryl group, or a substituted aryl group.
を含有することを特徴とする光可溶化組成物を提供する
ものである。The present invention provides a photosolubilizing composition comprising:
一般式（Ｉ）で示される酸により分解し得るシリルエ
ーテル基を有する化合物としては、好ましくは下記一般
式（IV）の繰返し単位を含有することを特徴とする。The compound having a silyl ether group decomposable by an acid represented by the general formula (I) is preferably characterized by containing a repeating unit represented by the following general formula (IV).
式中、R3は２価の脂肪族又は芳香族炭化水素を示す。
好ましくは親水性基、ウレタン基、ウレイド基、アミド
基、エステル基を有する２価の脂肪族又は芳香族炭化水
素を示す。 In the formula, R 3 represents a divalent aliphatic or aromatic hydrocarbon.
It is preferably a divalent aliphatic or aromatic hydrocarbon having a hydrophilic group, a urethane group, a ureido group, an amide group or an ester group.
なお本発明でいう親水性基としては、具体的には下記
に示されるものがある。Specific examples of the hydrophilic group in the present invention include those shown below.
CH2CH2−Ｏｎ CH2）lOｍCH2CH2−Ｏｎ 式中、ｌは１〜４の整数を示し、ｍ、ｎは２以上の整
数、好ましくは２〜100の整数、更に好ましくは２〜20
の整数を示す。Ｒはアルキル、又は置換基を有していて
もよいフエニル基を示す。特に好ましい親水性基はCH
2CH2−Ｏｎである。 CH 2 CH 2 -O n CH 2 ) l O m CH 2 CH 2 -O n In the formula, l represents an integer of 1 to 4, m and n are integers of 2 or more, preferably 2 to 100, and more preferably 2 to 20.
Indicates an integer. R represents alkyl or a phenyl group which may have a substituent. A particularly preferred hydrophilic group is CH
A 2 CH 2 -O n.
R4、R5は同一でも相異していてもよく、それぞれ水素
原子、アルキル、アルケニル、置換基を有していてもよ
いアリール又はアラルキル、もしくは−OR6を示す。好
ましくは炭素数１〜４個のアルキル、又は−OR6を示
す。R6は置換基を有していてもよりアルキル、アリー
ル、もしくはアラルキル基、好ましくは炭素数１〜８個
のアルキル、又は炭素数６〜15個のアリール基を示す。R 4 and R 5 may be the same or different and each represents a hydrogen atom, alkyl, alkenyl, aryl or aralkyl which may have a substituent, or —OR 6 . Preferably an 1-4 alkyl carbon atoms, or -OR 6. R 6 represents an alkyl, aryl, or aralkyl group, preferably an alkyl group having 1 to 8 carbon atoms, or an aryl group having 6 to 15 carbon atoms, which may have a substituent.
また本発明に用いられる化合物（ａ）は、一般式（I
V）で示される繰り返し単位を２種以上含有していても
よい。The compound (a) used in the present invention has the general formula (I
You may contain 2 or more types of repeating units shown by V).
本発明の（ａ）における化合物の具体例としては次に
示すものが含まれる。Specific examples of the compound in (a) of the present invention include those shown below.
なお具体例中のｎは２以上の整数を示す。またｘ、
ｙ、ｚはモル比を示し、化合物例Ｉ−29、30、33では、
ｘ＝10〜85モル％、ｙ＝５〜80モル％、ｚ＝10〜85モル
％である。また化合物例Ｉ−５〜16、18、27〜28、32、
35、及び39〜40ではｘ＝５〜90モル％、ｙ＝10〜95モル
％を示す。 Note that n in the specific examples represents an integer of 2 or more. Also x,
y and z represent molar ratios, and in compound examples I-29, 30, 33,
x = 10 to 85 mol%, y = 5 to 80 mol%, and z = 10 to 85 mol%. In addition, compound examples I-5 to 16, 18, 27 to 28, 32,
In 35 and 39-40, x = 5-90 mol% and y = 10-95 mol% are shown.
又これら酸により分解し得るシリルエーテル基を有す
る化合物と組み合せて用いる活性光線の照射により酸を
発生し得る化合物としては下記一般式（II）で示される
ジスルホン化合物 R1−SO2−SO2−R2 （II） 式中、R1およびR2は各々独立してアリール基あるいは
置換アリール基を表わす。Further, as a compound capable of generating an acid upon irradiation with an actinic ray used in combination with a compound having a silyl ether group capable of decomposing by an acid, a disulfone compound represented by the following general formula (II) R 1 —SO 2 —SO 2 — R 2 (II) In the formula, R 1 and R 2 each independently represent an aryl group or a substituted aryl group.
あるいは下記一般式（III）で示される化合物が好適
である。Alternatively, a compound represented by the following general formula (III) is preferable.
式中、Ａはアリーレン基、置換アリーレン基、アルキ
レン基、置換アルキレン基、アルケニレン基、置換アル
ケニレン基を表わす。Ｒはアルキル基、置換アルキル
基、アリール基、置換アリール基を表わす。 In the formula, A represents an arylene group, a substituted arylene group, an alkylene group, a substituted alkylene group, an alkenylene group, or a substituted alkenylene group. R represents an alkyl group, a substituted alkyl group, an aryl group, or a substituted aryl group.
一般式（II）で示される化合物におけるR1およびR2は
各々独立してアリール基あるいは置換アリール基を表わ
すが、アリール基としては、単環および２巻のものが好
ましく、例えばフエニル基、α−ナフチル基、β−ナフ
チル基などが含まれる。R1およびR2の置換アリール基
は、上記のようなアリール基に、例えばメチル基、エチ
ル基などの炭素原子数１〜２個のアルキル基、例えばメ
トキシ基、エトキシ基などの炭素原子数１〜２個のアル
コキシ基、例えば塩素原子、臭素原子などのハロゲン原
子、ニトロ基、フエニル基、カルボキシ基、シアノ基な
どが置換したものが含まれ、具体的には４−クロロフエ
ニル基、２−クロロフエニル基、４−ブロモフエニル
基、４−ニトロフエニル基、３−ニトロフエニル基、４
−フエニルフエニル基、４−メチルフエニル基、２−メ
チルフエニル基、４−エチルフエニル基、４−メトキシ
フエニル基、２−メトキシフエニル基、４−エトキシフ
エニル基、２−カルボキシフエニル基、４−シアノフエ
ニル基、４−メチル−１−ナフチル基、４−クロロ−１
−ナフチル基、５−ニトロ−１−ナフチル基、６−クロ
ロ−２−ナフチル基、４−ブロモ−２−ナフチル基、５
−ニトロ−２−ナフチル基などがあげられる。R 1 and R 2 in the compound represented by the general formula (II) each independently represent an aryl group or a substituted aryl group, and the aryl group is preferably a monocyclic ring or a bicyclic group, for example, a phenyl group, α -Naphthyl group, β-naphthyl group and the like are included. The substituted aryl group represented by R 1 and R 2 is the same as the above aryl group having 1 to 2 carbon atoms such as methyl group and ethyl group, and 1 carbon atoms such as methoxy group and ethoxy group. ~ 2 alkoxy groups, for example, those substituted with halogen atoms such as chlorine atom, bromine atom, nitro group, phenyl group, carboxy group, cyano group and the like, specifically, 4-chlorophenyl group, 2-chlorophenyl group Group, 4-bromophenyl group, 4-nitrophenyl group, 3-nitrophenyl group, 4
-Phenylphenyl group, 4-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 4-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 2-carboxyphenyl group, 4-cyanophenyl group Group, 4-methyl-1-naphthyl group, 4-chloro-1
-Naphthyl group, 5-nitro-1-naphthyl group, 6-chloro-2-naphthyl group, 4-bromo-2-naphthyl group, 5
Examples include -nitro-2-naphthyl group.
本発明で用いられる一般式（II）で表わされる化合物
は、ジー．シー．デンサー，ゼーラー．ら著「ジヤーナ
ル オブ オルガニツク ケミストリー」（G.C.Dense
r,Jr.ら著、「Journal of Organic Chemistry」）31,34
18〜3419（1966）記載の方法、テー．ピー．ヒルドイツ
チ著「ジヤーナル オブ ザ ケミカル ソサイアテ
イ」（T.P.Hilditch著，「Journal of the Chemical So
ciety」）93,1524〜1527（1908）記載の方法、あるいは
オー．ヒンズベルク著「ベリヒテ デア ドイチエン
ヘミシエ ゲゼルシヤフト」（O.Hinsberg著，「Berich
te der Deutschen Chemischen Gesellschaft」）49,259
3〜2594（1916）記載の方法等にしたがい合成できる。
すなわち、硫酸水溶液中において、硫酸コバルト（II
I）を用い、一般式（IV）で示されるスルフイン酸より
合成する方法、キサントゲン酸エチルを用い、一般式
（Ｖ）で示されるスルホン酸クロリドより合成する方
法、あるいは塩基性条件下、一般式（II）で示されるス
ルフイン酸と一般式（III）で示されるスルホン酸クロ
リド反応させ合成する方法等があげられる。The compound represented by the general formula (II) used in the present invention is a diene compound. C. Denser, Seeler. Et al. "The Journal of Organic Chemistry" (GCDense
r, Jr. et al., "Journal of Organic Chemistry") 31,34
18-3419 (1966), the method. Pee. Hildeerchi, "Journal of the Chemical Society" (TP Hilditch, "Journal of the Chemical Societies"
ciety ”) 93, 1524-1527 (1908), or Oh. Hinsberg "Berichte Der Deutschen"
Hemisie Gezershyaft "(O. Hinsberg," Berich
te der Deutschen Chemischen Gesellschaft ") 49,259
It can be synthesized according to the method described in 3 to 2594 (1916).
That is, in a sulfuric acid aqueous solution, cobalt sulfate (II
I) is used to synthesize from sulfinic acid represented by the general formula (IV), ethyl xanthate is used to synthesize from sulfonic acid chloride represented by the general formula (V), or under basic conditions. Examples thereof include a method of synthesizing a sulfinic acid represented by (II) with a sulfonic acid chloride represented by the general formula (III).
Ｒ−SO2H （IV） Ｒ′−SO2Cl （Ｖ） （ここで、ＲおよびＲ′は一般式（II）で定義されたR1
およびR2と同一の意味である。） 以下に本発明に使用される一般式（II）で示される具
体的な化合物を例示する。R—SO 2 H (IV) R′—SO 2 Cl (V) (wherein R and R ′ are R 1 defined in the general formula (II).
And R 2 have the same meaning. ) Specific examples of the compound represented by the general formula (II) used in the present invention are shown below.
又一般式（III）で表わされる光重合開始剤は、G.F.J
aubert著、Ber.,28,360（1895）の方法、D.E.Amesら
著、J.Chem.Soc.,3518（1955）の方法、あるいはM.A.St
olbergら著、J.Amer.Chem.Soc.,79,2615（1957）の方法
等に従い合成される一般式（VI） （ここで、Ａは一般式（III）の場合と同義） で表わされる化合物とＲ−SO2Cl（ここで、Ｒは一般式
（III）の場合と同義。）で表わされる有機スルホン酸
クロリドとを塩基性条件下、たとえば、L.Bauerら著、
J.Org.Chem.,24,1293（1959）の方法にしたがい合成す
ることが可能である。 The photopolymerization initiator represented by the general formula (III) is GFJ
Aubert, Ber., 28 , 360 (1895), DE Ames et al., J. Chem. Soc., 3518 (1955), or MASt.
General formula (VI) synthesized according to the method of J. Amer. Chem. Soc., 79 , 2615 (1957) by olberg et al. (Here, A has the same meaning as in the case of the general formula (III)) and an organic sulfonic acid chloride represented by R-SO 2 Cl (wherein R has the same meaning as in the case of the general formula (III)). Under basic conditions, for example, by L. Bauer et al.,
It can be synthesized according to the method of J. Org. Chem., 24 , 1293 (1959).
一般式（III）において、Ａのアリーレン基は、好ま
しくは単環および２巻のものであり、例えばフエニレン
基、ナフチレン基など、より具体的にはｏ−フエニレン
基、1,8−ナフチレン基、2,3−ナフチレン基などが含ま
れる。Ａの置換アリーレン基は、上記の如きアリーレン
基に、例えば塩素原子、臭素原子などのハロゲン原子、
ニトロ基、アセチルアミノ基などの置換基を有するもの
であつて、例えばブロモフエニレン基、クロロフエニレ
ン基、ニトロフエニレン基、アセチルアミノフエニレン
基、ブロモナフチレン基、クロロナフチレン基、ニトロ
ナフチレン基などが含まれる。また、Ａのアルキレン基
は、直鎖、分枝および環状のものであつて、好ましくは
炭素原子数が１〜約６のものであり、例えば、メチレン
基、エチレン基、プロピレン基、シクロブチレン基、シ
クロヘキシレン基などが含まれる。また、Ａの置換アル
キレン基は、上記の如きアルキレン基に、例えばフエニ
ル基などのアリール基が置換したもの、例えばフエニル
エチレン基、ジフエニルエチレン基などが含まれる。ま
たＡのアルケニレン基は、好ましくは炭素原子数が２〜
４のものであり、例えばビニリデン基、ブテニレン基な
どが含まれる。更にＡの置換アルケニレン基は、上記の
ようなアルケニレン基に、例えばフエニル基などのアリ
ール基が置換したものであつて、例えばフエニルビニリ
デン基、ジフエニルビニリデン基などが含まれる。In the general formula (III), the arylene group represented by A is preferably a monocyclic ring or a bicyclic group, for example, a phenylene group, a naphthylene group, and the like, more specifically, an o-phenylene group, a 1,8-naphthylene group, A 2,3-naphthylene group and the like are included. The substituted arylene group of A is the same as the above arylene group, for example, a halogen atom such as a chlorine atom or a bromine atom,
Those having a substituent such as nitro group and acetylamino group include, for example, bromophenylene group, chlorophenylene group, nitrophenylene group, acetylaminophenylene group, bromonaphthylene group, chloronaphthylene group, nitronaphthylene group and the like. The alkylene group represented by A is linear, branched or cyclic and preferably has 1 to about 6 carbon atoms, and examples thereof include a methylene group, an ethylene group, a propylene group and a cyclobutylene group. , A cyclohexylene group and the like. Further, the substituted alkylene group of A includes, for example, an alkylene group as described above substituted with an aryl group such as a phenyl group, for example, a phenylethylene group, a diphenylethylene group and the like. The alkenylene group of A preferably has 2 to 10 carbon atoms.
No. 4, and includes, for example, vinylidene group, butenylene group and the like. Further, the substituted alkenylene group of A is the above-mentioned alkenylene group substituted with an aryl group such as a phenyl group, and includes, for example, a phenylvinylidene group and a diphenylvinylidene group.
一方、一般式（III）におけるＲのアルキル基は、直
鎖、分枝、環状のもの、より好ましくは直鎖のものであ
り、好ましくは炭素原子数が１〜18個のものであつて、
例えばメチル、エチル、ブチル、ヘキシル、オクチル、
ドデシル、ヘキサデシルなどの各基が含まれる。また、
Ｒの置換アルキル基は、上記のようなアルキル基に、例
えば塩素原子のようなハロゲン原子、例えばメトキシ基
のような炭素原子数１〜２個のアルコキシ基などが置換
されたものであつて、具体的には２−クロロエチル基、
２−メトキシエチル基などが含まれる。また、Ｒのアリ
ール基には、好ましくは単環および２環のものであつ
て、例えばフエニル基、ナフチル基などが含まれる。ま
た、Ｒの置換アルキル基は、上記のようなアリール基
に、例えばメチル基、エチル基などの炭素原子数１〜２
個のアルキル基、例えばメトキシ基、エトキシ基などの
炭素原子数１〜２個のアルコキシ基、例えば塩素原子な
どのハロゲン原子などが置換したものが含まれ、具体的
にはメチルフエニル基、ジメチルフエニル基、メトキシ
フエニル基、クロロフエニル基、メトキシナフチル基な
どがあげられる。On the other hand, the alkyl group represented by R in the general formula (III) is a straight chain, branched chain, or cyclic group, more preferably a straight chain group, preferably having 1 to 18 carbon atoms,
For example, methyl, ethyl, butyl, hexyl, octyl,
Included are groups such as dodecyl and hexadecyl. Also,
The substituted alkyl group for R is the above alkyl group substituted with a halogen atom such as a chlorine atom, an alkoxy group having 1 to 2 carbon atoms such as a methoxy group, and the like. Specifically, a 2-chloroethyl group,
A 2-methoxyethyl group and the like are included. The aryl group of R is preferably monocyclic or bicyclic, and includes, for example, a phenyl group and a naphthyl group. Further, the substituted alkyl group of R is the above aryl group, for example, having 1 to 2 carbon atoms such as methyl group and ethyl group.
Alkyl groups, for example, methoxy groups, ethoxy groups, and other alkoxy groups having 1 to 2 carbon atoms, for example, those substituted with halogen atoms, such as chlorine atoms, and the like, specifically, methylphenyl group, dimethylphenyl group Group, methoxyphenyl group, chlorophenyl group, methoxynaphthyl group and the like.
以下に本発明に使用される一般式（III）で示される
具体的な化合物を例示する。The specific compounds represented by the general formula (III) used in the present invention are exemplified below.
これらの活性光線の照射により酸を発生し得る化合物
と前記酸により分解し得るシリルエーテル基を少なくと
も１個有する化合物との割合は、重量比で0.001:1〜2:1
であり、好ましくは0.02:1〜0.8:1で使用される。 The proportion of the compound capable of generating an acid upon irradiation with actinic rays and the compound having at least one silyl ether group decomposable by the acid is 0.001: 1 to 2: 1 by weight.
And is preferably used at 0.02: 1 to 0.8: 1.
本発明の光可溶化組成物は、上記活性光線の照射によ
り酸を発生し得る化合物と、酸により分解し得るシリル
エーテル基を少なくとも１個有する化合物の組合せのみ
で使用することができるが、アルカリ可溶性樹脂と混合
して用いた方が好ましい。好適なアルカリ可溶性樹脂に
は、ノボラツク型フエノール樹脂が含まれ、具体的に
は、フエノールホルムアルデヒド樹脂、ｏ−クレゾール
ホルムアルデヒド樹脂、ｍ−クレゾールホルムアルデヒ
ド樹脂などが含まれる。更に特開昭50−125806号公報に
記されている様に上記のようなフエノール樹脂と共に、
ｔ−ブチルフエノールホルムアルデヒド樹脂のような炭
素数３〜８のアルキル基で置換されたフエノールまたは
クレゾールとホルムアルデヒドとの縮合物とを併用する
と、一層好ましい。アルカリ可溶性樹脂は、感光性レジ
スト形成性組成物の全重量を基準として約40〜約90重量
％、より好ましくは60〜80重量％含有させられる。The photo-solubilizing composition of the present invention can be used only as a combination of a compound capable of generating an acid upon irradiation with actinic rays and a compound having at least one silyl ether group decomposable by an acid. It is preferable to use it as a mixture with a soluble resin. Suitable alkali-soluble resins include novolak type phenolic resins, and specifically, phenol formaldehyde resin, o-cresol formaldehyde resin, m-cresol formaldehyde resin and the like. Further, together with the above-mentioned phenol resin as described in JP-A-50-125806,
It is more preferable to use a condensate of formaldehyde and phenol or cresol substituted with an alkyl group having 3 to 8 carbon atoms such as t-butylphenol formaldehyde resin in combination. The alkali-soluble resin is contained in an amount of about 40 to about 90% by weight, more preferably 60 to 80% by weight, based on the total weight of the photosensitive resist-forming composition.
本発明の光可溶化組成物には必要に応じて、更に染
料、顔料、可塑剤及び前記酸を発生し得る化合物の酸発
生効率を増大させる化合物（所謂増感剤）などを含有さ
せることができる。好適な染料としては油溶性染料及び
塩基性染料がある。具体的には、オイルイエロー＃10
1、オイルイエロー＃130、オイルピンク＃312、オイル
グリーンBG、オイルブルーBOS、オイルブルー＃603、オ
イルブラツクBY、オイルブラツクBS、オイルブラツクＴ
−505（以上、オリエント化学工業株式会社製）クリス
タルバイオレツト（CI42555）、メチルバイオレツト（C
I42535）、ローダミンＢ（CI45170B）、マラカイトグリ
ーン（CI42000）、メチレンブルー（CI52015）などをあ
げることができる。If necessary, the photosolubilizing composition of the present invention may further contain a dye, a pigment, a plasticizer and a compound (a so-called sensitizer) that increases the acid generation efficiency of the compound capable of generating the acid. it can. Suitable dyes include oil-soluble dyes and basic dyes. Specifically, Oil Yellow # 10
1, oil yellow # 130, oil pink # 312, oil green BG, oil blue BOS, oil blue # 603, oil black BY, oil black BS, oil black T
-505 (above, manufactured by Orient Chemical Industry Co., Ltd.) Crystal Violet (CI42555), Methyl Violet (C
I42535), Rhodamine B (CI45170B), Malachite Green (CI42000), Methylene Blue (CI52015) and the like.
本発明の光可溶化組成物は、上記各成分を溶解する溶
媒に溶かして支持体上に塗布する。ここで使用する溶媒
としては、エチレンジクロライド、シクロヘキサノン、
メチルエチルケトン、エチレングリコールモノメチルエ
ーテル、エチレングリコールモノメチルエーテル、２−
メトキシエチルアセテート、トルエン、酢酸エチルなど
があり、これらの溶媒を単独あるいは混合して使用す
る。そして上記成分中の濃度（添加物を含む全固形分）
は、２〜50重量％である。このうち、本発明の組成の好
ましい濃度（固形分）は0.1〜25重量％である。また、
塗布量は用途により異なるが、例えば感光性平板印刷版
についていえば一般的に固形分として0.5〜3.0g/m2が好
ましい。塗布量が少くなるにつれ感光性は大になるが、
感光膜の物性は低下する。The photosolubilizing composition of the present invention is dissolved in a solvent that dissolves each of the above components and applied onto a support. As the solvent used here, ethylene dichloride, cyclohexanone,
Methyl ethyl ketone, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether, 2-
There are methoxyethyl acetate, toluene, ethyl acetate and the like, and these solvents are used alone or as a mixture. And the concentration in the above components (total solid content including additives)
Is 2 to 50% by weight. Among these, the preferred concentration (solid content) of the composition of the present invention is 0.1 to 25% by weight. Also,
The coating amount varies depending on the use, but for a photosensitive lithographic printing plate, for example, a solid content of 0.5 to 3.0 g / m 2 is generally preferable. As the coating amount decreases, the photosensitivity increases,
The physical properties of the photosensitive film deteriorate.
本発明の光可溶化組成物を用いて平版印刷版を製造す
る場合、その支持体としては、親水化処理したアルミニ
ウム板、たとえばシリケート処理アルミニウム板、陽極
酸化アルミニウム板、砂目立てしたアルミニウム板、シ
リケート電着したアルミニウム板があり、その他亜鉛
板、ステンレス板、クローム処理鋼板、親水化処理した
プラスチツクフイルムや紙を上げることができる。In the case of producing a lithographic printing plate using the photosolubilizing composition of the present invention, the support thereof is a hydrophilized aluminum plate, for example, a silicate-treated aluminum plate, an anodized aluminum plate, a grained aluminum plate, or a silicate. There are aluminum plates that have been electrodeposited, and other examples include zinc plates, stainless plates, chrome-treated steel plates, hydrophilicized plastic films and paper.
また印刷用校正版、オーバーヘツドプロジエクター用
フイルム第２原図用フイルムの製造に適する支持体とし
てはポリエチレンテレフタレートフイルム、トリアセテ
ートフイルム等の透明フイルムや、これらのプラスチツ
クフイルムの表面を化学的あるいは物理的にマツト化し
たものをあげることが出来る。ホトマスク用フイルムの
製造に適する支持体としてはアルミニウム、アルミニウ
ム合金やクロムを蒸着させたポリエチレンテレフタレー
トフイルムや着色層をもうけたポリエチレンテレフタレ
ートフイルムをあげることが出来る。またホトレジスト
として上記以外の種々の支持体、例えば銅板、銅メツキ
板、ガラス板上に本発明の光可溶化組成物を塗布して使
用される。Further, as a support suitable for producing a proof plate for printing, a film for an overhead projector, a film for the second original drawing, a transparent film such as polyethylene terephthalate film and triacetate film, and the surface of these plastic films is chemically or physically I can give you a matt thing. As a support suitable for producing a photomask film, a polyethylene terephthalate film having aluminum, an aluminum alloy or chromium vapor deposited thereon, or a polyethylene terephthalate film having a colored layer can be mentioned. Further, as a photoresist, various supports other than the above, for example, a copper plate, a copper plating plate, and a glass plate are coated with the photosolubilizing composition of the present invention and used.
本発明に用いられる活性光線の光源としては例えば、
水銀灯、メタルハライドランプ、キセノンランプ、ケミ
カルランプ、カーボンアーク灯などがある。また高密度
エネルギービーム（レーザービーム又は電子線）による
走査露光も本発明に使用することができる。このような
レーザービームとしてはヘリウム・ネオンレーザー、ア
ルゴンレーザー、クリプトンイオンレーザー、ヘリウム
・カドミウムレーザーなどが挙げられる。Examples of the actinic light source used in the present invention include:
There are mercury lamps, metal halide lamps, xenon lamps, chemical lamps, and carbon arc lamps. Scanning exposure with a high-density energy beam (laser beam or electron beam) can also be used in the present invention. Examples of such a laser beam include a helium / neon laser, an argon laser, a krypton ion laser, and a helium / cadmium laser.
本発明の光可溶化組成物に対する現像液としては、珪
酸ナトリウム、珪酸カリウム、水酸化ナトリウム、水酸
化カリウム、水酸化リチウム、第三リン酸ナトリウム、
第二リン酸ナトリウム、第三リン酸アンモニウム、第二
リン酸アンモニウム、メタ珪酸ナトリウム、重炭酸ナト
リウム、アンモニア水などのような無機アルカリ剤の水
溶液が適当であり、それらの濃度が0.1〜10重量％、好
ましくは0.5〜５重量％になるように添加される。The developer for the photosolubilizing composition of the present invention, sodium silicate, potassium silicate, sodium hydroxide, potassium hydroxide, lithium hydroxide, tribasic sodium phosphate,
Aqueous solutions of inorganic alkaline agents such as dibasic sodium phosphate, tribasic ammonium phosphate, dibasic ammonium phosphate, sodium metasilicate, sodium bicarbonate, aqueous ammonia and the like are suitable, and their concentration is 0.1 to 10% by weight. %, Preferably 0.5 to 5% by weight.
また、該アルカリ性水溶液には、必要に応じ界面活性
剤やアルコールなどのような有機溶媒を加えることもで
きる。If necessary, an organic solvent such as a surfactant or alcohol can be added to the alkaline aqueous solution.
「実施例」 以下、本発明を実施例により更に詳細に説明するが、
本発明の内容がこれにより限定さるものではない。Hereinafter, the present invention will be described in more detail with reference to examples.
The contents of the present invention are not limited thereby.
実施例１ 厚さ0.24mmの2Sアルミニウム板を80℃に保つた第３燐
酸ナトリウムの10％水溶液に３分間浸漬して脱脂し、ナ
イロンブラシで砂目立てした後アルミン酸ナトリウムで
約10秒間エツチングして、硫酸水素ナトリウム３％水溶
液でデスマツト処理を行つた。このアルミニウム板を20
％硫酸中で電流密度2A/dm2において２分間陽極酸化を行
いアルミニウム板を作製した。Example 1 A 2S aluminum plate having a thickness of 0.24 mm was immersed in a 10% aqueous solution of sodium triphosphate kept at 80 ° C. for 3 minutes to be degreased, grained with a nylon brush, and then etched with sodium aluminate for about 10 seconds. Then, desmut treatment was performed with a 3% aqueous solution of sodium hydrogen sulfate. 20 pieces of this aluminum plate
Anodizing was performed for 2 minutes at a current density of 2 A / dm 2 in% sulfuric acid to produce an aluminum plate.
次に下記感光液〔Ａ〕の本発明の化合物（ａ）の種類
を変えて５種類の感光液〔Ａ〕−１〜〔Ａ〕−５を調整
し、この感光液を陽極酸化させたアルミニウム板の上に
塗布し、100℃で２分間乾燥して、それぞれの感光性平
版印刷版〔Ａ〕−１〜〔Ａ〕−５を作製した。このとき
の塗布量は全て乾燥重量で1.5g/m2であつた。Next, five kinds of photosensitive solutions [A] -1 to [A] -5 were prepared by changing the kind of the compound (a) of the present invention in the following photosensitive solution [A], and the anodized aluminum of this photosensitive solution was prepared. The solution was applied onto a plate and dried at 100 ° C. for 2 minutes to prepare each photosensitive lithographic printing plate [A] -1 to [A] -5. The coating amount at this time was 1.5 g / m 2 in dry weight.
また、感光液〔Ａ〕−１〜〔Ａ〕−５に用いた本発明
の化合物（ａ）は第１表に示す。Further, Table 1 shows the compound (a) of the present invention used in the photosensitive liquids [A] -1 to [A] -5.
感光液〔Ａ〕 本発明化合物（ａ） 0.40g クレゾール−ホルムアルデヒドノボラツク樹脂 1.0 g 本発明の化合物（ｂ） （III−22） 0.05g オイルブルー＃603 （オリエント化学工業（株）製） 0.01g エチレンジクロリド 10 g メチルセロソルブ 10 g 次に比較例として下記の感光液〔Ｂ〕を感光液〔Ａ〕
と同様に塗布し、感光性平版印刷版〔Ｂ〕を作製した。Photosensitive solution [A] Compound of the present invention (a) 0.40 g Cresol-formaldehyde novolak resin 1.0 g Compound of the present invention (b) (III-22) 0.05 g Oil blue # 603 (manufactured by Orient Chemical Industry Co., Ltd.) 0.01 g Ethylene dichloride 10 g Methyl cellosolve 10 g Next, as a comparative example, the following photosensitive solution [B] was used.
And a photosensitive lithographic printing plate [B] was prepared.
感光液〔Ｂ〕 クレゾール−ホルムアルデヒドノボラツク樹脂と1,2−
ナフトキノン−２−ジアジド−５−スルホニルクロリド
その縮合生成物 0.45g クレゾール−ホルムアルデヒドノボラツク樹脂 1.1 g 1,2−ナフトキノン−２−ジアジド−４−スルホニルク
ロリドオイルブルー＃603 0.02g （オリエント化学工業（株）製） 0.01g エチレンジクロリド 10 g メチルセロソルブ 10 g 乾燥後の塗布重量は1.5g/m2であつた。感光性平版印
刷版〔Ａ〕−１〜〔Ａ〕−５及び〔Ｂ〕の感光層上に濃
度差0.15のグレースケールを密着させ、30アンペアのカ
ーボンアーク灯で70cmの距離から露光を行つた。Photosensitive solution [B] Cresol-formaldehyde novolac resin and 1,2-
Naphthoquinone-2-diazide-5-sulfonyl chloride its condensation product 0.45 g Cresol-formaldehyde novolac resin 1.1 g 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride oil blue # 603 0.02 g (Orient Chemical Industries Ltd. ) 0.01 g Ethylene dichloride 10 g Methyl cellosolve 10 g The coating weight after drying was 1.5 g / m 2 . A gray scale with a density difference of 0.15 was brought into close contact with the photosensitive layers of the photosensitive lithographic printing plates [A] -1 to [A] -5 and [B], and exposure was performed from a distance of 70 cm with a carbon amp lamp of 30 amperes. .
本発明の優れた感光性を示す為に露光された感光性平
版印刷版〔Ａ〕−１〜〔Ａ〕−５及び〔Ｂ〕をDP−４
（商品名：富士写真フイルム（株）製）の８倍希釈水溶
液で25℃において60秒間浸漬現像し、濃度差0.15のグレ
ースケールで５段目が完全にクリアーとなる露光時間を
求めたところ第１表に示すとおりとなつた。The photosensitive lithographic printing plates [A] -1 to [A] -5 and [B] exposed to show the excellent photosensitivity of the present invention are used as DP-4.
After dipping and developing in 8 times diluted aqueous solution (trade name: Fuji Photo Film Co., Ltd.) at 25 ° C. for 60 seconds, the exposure time required to completely clear the 5th step on a gray scale with a density difference of 0.15 was obtained. The results are shown in Table 1.
なお第１表における本発明の化合物（ａ）、Ｉ−５、
11、14、28、40では、ｎ＝４、x/y＝40/60（モル比）の
ものを使用した。分子量はいずれもGPC（Gel Permeatio
n Chromatography）ポリスチレン標準で2500〜5000のも
のであつた。 In addition, the compound (a) of the present invention in Table 1 and I-5,
In 11, 14, 28 and 40, n = 4 and x / y = 40/60 (molar ratio) were used. The molecular weights of all are GPC (Gel Permeatio
n Chromatography) The polystyrene standard was 2500-5000.
第１表からわかるように本発明の化合物を用いた感光
性平版印刷版〔Ａ〕−１〜〔Ａ〕−５はいずれも〔Ｂ〕
より露光時間が少なく、感度が高い。As can be seen from Table 1, all of the photosensitive lithographic printing plates [A] -1 to [A] -5 using the compound of the present invention [B]
Shorter exposure time and higher sensitivity.
実施例２ 下記感光液〔Ｃ〕において活性光線の照射により酸を
発生し得る本発明の化合物（ｂ）の種類を変えて、４種
類の感光液〔Ｃ〕−１〜〔Ｃ〕−４を調整し、実施例１
と同様にして、感光性平版印刷版〔Ｃ〕−１〜〔Ｃ〕−
４を作製した。Example 2 Four types of photosensitive solutions [C] -1 to [C] -4 were prepared by changing the type of the compound (b) of the present invention capable of generating an acid upon irradiation with actinic rays in the following photosensitive solution [C]. Adjust, Example 1
In the same manner as described above, the photosensitive lithographic printing plates [C] -1 to [C]-
4 was produced.
感光液〔Ｃ〕 本発明の化合物（ａ）（Ｉ−12） 0.31g クレゾール−ホルムアルデヒドノボラツク樹脂 1.0 g 本発明の化合物（ｂ） 0.05g オイルブルー（オリエント化学工業（株）製） 0.01g エチレンジクロリド 10 ｇ メチルセロソルブ 10 ｇ 塗布量は全て乾燥重量で1.5g/m2であつた。なお感光
液〔Ｃ〕で使用した本発明の化合物（ａ）（Ｉ−12）は
ｎ＝４、x/y＝40/60（モル比）であり、分子量はGPC、
ポリスチレン標準で3,500であつた。また感光液〔Ｃ〕
−１〜〔Ｃ〕−４に用いた、活性光線の照射により酸を
発生する本発明の化合物（ｂ）は第２表に示す。感光性
平版印刷版〔Ｃ〕−１〜〔Ｃ〕−４及び実施例１で作製
した〔Ｂ〕の感光層上に濃度差0.15のグレースケールを
密着させ、30アンペアのカーボンアーク灯で70cmの距離
から露光を行つた。Photosensitive solution [C] Compound (a) of the present invention (I-12) 0.31 g Cresol-formaldehyde novolak resin 1.0 g Compound of the present invention (b) 0.05 g Oil blue (manufactured by Orient Chemical Industry Co., Ltd.) 0.01 g Ethylene 10 g of dichloride and 10 g of methyl cellosolve were all applied in a dry weight of 1.5 g / m 2 . The compound (a) (I-12) of the present invention used in the photosensitive solution [C] has n = 4, x / y = 40/60 (molar ratio), and has a molecular weight of GPC,
The polystyrene standard was 3,500. In addition, the photosensitive liquid [C]
Table 2 shows the compounds (b) of the present invention which are used for -1 to [C] -4 and generate an acid upon irradiation with actinic rays. A gray scale having a density difference of 0.15 was brought into close contact with the photosensitive lithographic printing plates [C] -1 to [C] -4 and the photosensitive layer of [B] prepared in Example 1 and a 70 cm light intensity was applied with a carbon arc lamp of 30 ampere. Exposure was done from a distance.
露光された感光性平版印刷版〔Ｃ〕−１〜〔Ｃ〕−４
及び〔Ｂ〕をDP−４（商品名：富士写真フイルム（株）
製）の８倍希釈水溶液で25℃において60秒間浸漬現像
し、濃度差0.15のグレースケールで５段目が完全にクリ
アーとなる露光時間を求めたところ、第２表に示すとお
りとなつた。Exposed photosensitive lithographic printing plate [C] -1 to [C] -4
And [B] as DP-4 (trade name: Fuji Photo Film Co., Ltd.)
It was subjected to immersion development for 60 seconds at 25.degree. C. with an 8 times diluted aqueous solution of a product), and the exposure time at which the fifth step was completely clear was obtained on a gray scale with a density difference of 0.15. The results are shown in Table 2.
第２表からわかるように本発明の化合物を用いた感光
性平版印刷版〔Ｃ〕−１〜〔Ｃ〕−４はいずれも〔Ｂ〕
より露光時間が少なく、感度が高い。 As can be seen from Table 2, all of the photosensitive lithographic printing plates [C] -1 to [C] -4 using the compound of the present invention [B]
Shorter exposure time and higher sensitivity.
Claims (1)
れる酸により分解し得るシリルエーテル基を少なくとも
１個有し現像液中での、その溶解度が酸の作用により増
大する化合物、及び Ｃ−Ｏ−Si （Ｉ） （ｂ） 下記一般式（II）あるいは（III）で示される
活性光線の照射により酸を発生し得る化合物 R1−SO2−SO2−R2 （II） 式中、R1およびR2は各々独立してアリール基あるいは置
換アリール基を表わす 式中、Ａはアリーレン基、置換アリーレン基、アルキレ
ン基、置換アルキレン基、アルケニレン基、置換アルケ
ニレン基を表わす。Ｒはアルキル基、置換アルキル基、
アリール基、置換アリール基を表わす を含有することを特徴とする光可溶化組成物。(A) A compound having at least one silyl ether group represented by the following general formula (I) which can be decomposed by an acid in the molecule and whose solubility in a developer is increased by the action of an acid. , And C—O—Si (I) (b) a compound represented by the following general formula (II) or (III) capable of generating an acid upon irradiation with an actinic ray R 1 —SO 2 —SO 2 —R 2 (II ) In the formula, R 1 and R 2 each independently represent an aryl group or a substituted aryl group. In the formula, A represents an arylene group, a substituted arylene group, an alkylene group, a substituted alkylene group, an alkenylene group, or a substituted alkenylene group. R is an alkyl group, a substituted alkyl group,
A photosolubilizing composition comprising an aryl group and a substituted aryl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60007087A JP2525568B2 (en) | 1985-01-18 | 1985-01-18 | Photosolubilizing composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60007087A JP2525568B2 (en) | 1985-01-18 | 1985-01-18 | Photosolubilizing composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61166544A JPS61166544A (en) | 1986-07-28 |
| JP2525568B2 true JP2525568B2 (en) | 1996-08-21 |
Family
ID=11656302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60007087A Expired - Lifetime JP2525568B2 (en) | 1985-01-18 | 1985-01-18 | Photosolubilizing composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2525568B2 (en) |
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Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60121446A (en) * | 1983-12-06 | 1985-06-28 | Fuji Photo Film Co Ltd | Photosolubilizable composition |
| JPS6037549A (en) * | 1983-08-10 | 1985-02-26 | Fuji Photo Film Co Ltd | Photosolubilizable composition |
| JPS61141442A (en) * | 1984-12-14 | 1986-06-28 | Fuji Photo Film Co Ltd | Photosoluble composition |
| JPS61151643A (en) * | 1984-12-26 | 1986-07-10 | Fuji Photo Film Co Ltd | Photosoluble composition |
-
1985
- 1985-01-18 JP JP60007087A patent/JP2525568B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61166544A (en) | 1986-07-28 |
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