JPS61166544A - Photosolubilizable composition - Google Patents

Abstract

PURPOSE:To form a photosolubilizable compsn. high in photosensitivity and wide in development latitude at the time of development by incorporating a compd. increasable in solubility in a developing soln. by the action of acid, and a compd. capable of producing acid upon the irradiation of actinic rays. CONSTITUTION:The photosolubilizable compsn. contains a compd. (a) having a silyl ether group decomposable with acid and increasable in solubility in a developing soln. by the action of acid, represented by formula 1, such as 1-1, preferably, having the repeating units of formula 4, and a compd. (b) represented by formula 2 or 3, such as formulae 2-1, 3-1, capable of producing acid upon the irradiation of the actinic rays, and a preferable mixing weight ratio of a/b is 0.02:1-0.8:1.

Description

DETAILED DESCRIPTION OF THE INVENTION "Industrial Application Field" The present invention relates to a pre-solubilized composition suitable for the production of lithographic printing plates, multicolor printing proofs, drawings for overhead projectors, IC circuits, and photomasks. For more details, see (
a) a compound having at least one silyl ether group that can be decomposed by an acid, and (b) by irradiation with actinic rays,
Novel presolubilization compositions containing compounds capable of generating acids.

"Conventional technology" Solubilize with actinic rays. Orthoquinonediazide compounds have been known as photosensitive substances that act on so-called positive chips, and have been widely used in lithographic printing plates, photoresists, and the like. Such orthoquinone diazide compounds include, for example, U.S. Pat.
No. 2゜747.091, No. 77, ri 7
No. 2, same No. λ, rr de, // Ko No., same No. Ko, f07
, No. 4zz, No. 3,0444,110, No. 3,0
4At, No. 111, No. J, 17μt, //j No. 3,04A4,111, No. 3.0μt, No. ii,
Same No. J, 04A&, /20, Same No. 3,0414, /Co No. 1, Same No. 3,0 da 4,722, Same No. i, out, i
Ko No. 3, No. 3.04/, 4AJO No. J, io
x, toy No. J, 104.

4Atj No. J, tJj No. 702, Atj No. 3゜44
It is described in numerous publications, including the specifications of No. A7.4CACJ.

These orthoquinone diazide compounds undergo cylysis when irradiated with actinic rays! There are nine methods that take advantage of the fact that they produce ring-membered carboxylic acids and are soluble in alkali, but all of them have the drawback of insufficient photosensitivity. This is because, in the case of orthoquinonediazide compounds, the quantum yield essentially does not exceed lt-.

Various attempts have been made to increase the photosensitivity of photosensitive compositions containing orthoquinone diazide compounds, but it has been extremely difficult to maintain development tolerance during development and increase photosensitivity without changing the composition. Ta. For example, examples of such attempts include Japanese Patent Publication No. 4 Ar-/λ Co., Ltd., Japanese Unexamined Patent Publication No. Sho J λ-410/Co-j, U.S. Patent No. 1A, JO7,17
The contents described in the specification such as No. 3 can be mentioned.

Also, recently, several proposals have been made regarding photosensitive compositions that act on positive chips without using an orthoquinone diazide compound. As one of them, for example,
Polymer compounds having an orthonitrocarbinol ester group as described in the specification of No. 2≦2 can be mentioned. However, in this case too, the photosensitivity cannot be said to be sufficient for the same reason as in the case of orthoquinone diazide. In addition, as a method of increasing photosensitivity using a photosensitive system that is activated by contact action, there is a known method of causing a second reaction with the acid generated by photolysis, thereby solubilizing the exposed area. The principle of is applied.

An example of such a combination is, for example, a combination of a compound that generates silicic acid by photolysis and an acetal or 0,N-acetal compound (Japanese Patent Application Laid-Open No. 4-1999 At-ryo).

No. 3), a combination with an orthoester or amide acetal compound (JP-A-Sho! I-/Co No. 0714c), a combination with a polymer having an acetal or ketal group in the main chain (
JP-A Sho, tJ-1334422), combination with enol ether compound (JP-A Sho!!-/, 222!), N
- Combination with acylimino carbonate compound (JP-A-11-7
No. 26236), and a combination with a polymer having an orthoester group in the main chain (Japanese Unexamined Patent Publication No. 17344/1989). In principle, these have quantum yields exceeding 1, so they may exhibit high photosensitivity, but in the case of acetals or O,N-acetal compounds, and in the case of polymers with acetal or ketal groups in the main chain. , because the rate of the second reaction by the acid generated by photolysis is slow, it does not exhibit sufficient photosensitivity for actual use. In addition, orthoester or amido-heptal compounds, enol ether compounds, and KN-acyliminocarbonate compounds certainly exhibit high photosensitivity, but they are not stable over time and cannot be stored for long periods of time. . Polymers having orthoester groups in their main chains also have high sensitivity, but have the disadvantage of narrow development tolerance during development.

"Problems to be Solved by the Invention" The purpose of this research is to provide a novel pre-solubilized composition in which these problems are solved. That is, the object is to provide a novel pre-solubilized composition that has high photosensitivity and wide development latitude during development.

Another purpose of this research is to provide a novel photo-solubilized composition that has excellent stability over time and can be stored for a long period of time.

Yet another objective of this research is to provide a novel photo-solubilized composition that is simple to manufacture and easily obtainable.

"Means for Solving the Problems" As a result of intensive studies to achieve the above object, the present inventor discovered that the above object could be achieved by using a novel photo-solubilizing composition, and the present invention Reached.

That is, the present invention provides (a) a compound having at least one acid-decomposable silyl ether group represented by the following general formula (I) in the molecule, whose solubility in a developer increases by the action of the acid. and 7cmo Si:5
(I) (b) General formula (II) below
Alternatively, a compound R1-802-8ox-Rz that can generate an acid upon irradiation with actinic rays represented by (III)
(II) In the formula, R1 and R2 each independently represent an aryl group or a substituted aryl group; Represents an alkenylene group. R represents an alkyl group, a substituted alkyl group, an aryl group, or a substituted aryl group.

The present invention provides a photo-solubilizable composition characterized in that it contains the following.
, .1 The compound having a silyl ether group that can be silyzed by an acid represented by the general formula (I) is preferably characterized by containing a repeating unit of the following general formula (IV).

÷R3-0-8i-0+(N) R.

In the formula, R3 represents a divalent aliphatic or aromatic hydrocarbon.

Preferably, it represents a divalent aliphatic or aromatic hydrocarbon having a hydrophilic group, urethane group, ureido group, amide group, or ester group.

Note that the hydrophilic group referred to in the present invention specifically includes those shown below.

+CH2CH2-0+.

÷÷CHI), o±i+CH2CH, -0+.

+ CHCH2-0+FiV+CHz CHz -0÷
.

■H During the ceremony! represents an integer from 1 to 2, m% n represents an integer of 2 or more, preferably an integer from 0 to 0, and more preferably an integer from 0 to 0. R represents an alkyl group or a phenyl group which may have a substituent.

A particularly preferred hydrophilic group is ÷CH2CH2-0+.

It is.

R4 and R5 may be the same or different, and each represents a hydrogen atom, alkyl, alkenyl, aryl or aralkyl which may have a substituent, or -OR. Preferably alkyl having l-≠ carbon atoms, or -ORg
i represents aR8 which may have a substituent, such as dialkyl, aryl, mosi or aralkyl group, preferably carbon number/~
represents an alkyl group having 4 −/Jr carbon atoms or an aryl group having 4−/Jr carbon atoms.

Further, the compound (a) used in the present invention has the general formula (M)
It may contain two or more types of repeating units represented by.

Specific examples of the compound (a)K of the present invention include those shown below.

(I-/) (knee λ) H3 (I-J) (I-1 (I-1> (i-A) (I-7) (1-t) (I-2) (I-10) ( I-//) In the specific examples, n represents an integer greater than or equal to
xZ indicates the molar ratio, and in Compound Example I-Kota, 30.33, X: 10~ftmol%, y=j~rOmolti, z=
6 which is io, rz morti and compound examples 1-t to 16,
it, 27-21.3, 3j1 and 32-4AO, x==r~riO morchi, y=10~rij morchi.

In addition, as a compound capable of generating an acid upon irradiation with actinic rays, which is used in combination with a compound having a silyl ether group that can be decomposed by an acid, the disulfone compound R1-802302-R2 (IF ) represented by the following general formula (IN) is used. , R1 and R2 each independently represent an aryl group or a substituted aryl group.

A certain b is preferably a compound represented by the following general formula (II[).

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.

R1 and R2 in the compound represented by general formula (n)
each independently represents an aryl group or a substituted aryl group, and the aryl group is preferably monocyclic or cocyclic, and includes, for example, a phenyl group, an α-naphthyl group, a β-naphthyl group, and the like. Replacement of R1 and R2 completed -
The group is an aryl group as described above, for example, a methyl group,
Alkyl groups having 1-2 carbon atoms such as ethyl groups, 1 to 2 carbon atoms such as methoxy and ethoxy groups;
・;"'s descendant (change in content L) 2 alkoxy groups,
For example, it includes those substituted with a halogen atom such as a chlorine atom or a bromine atom, a nitro group, a phenyl group, a carboxy group, a cyano group, etc. In terms of n and L forms, μm chlorophenyl group, cochlorophenyl group, ll-1 romophenyl group, μm nitrophenyl group, 3-nitrophenyl group, Hiro-phenylphenyl group, μm methylphenyl group, co-methylphenyl group, μm methylphenyl group, ≠-methoxyphenyl group, co-methoxyphenyl group, Hiro-ethoxyphenyl group,
λ-carboxyphenyl group, Hiro-cyanophenyl group, ≠
-methyl-/-f methyl group, ≠-chloro! -Naphthyl group,! -nitro l-naphthyl group, 6-chloro-2-
Naphthyl group, ≠-promo λ-naphthyl group,! Examples include -nitro-2-naphthyl group.

The compound represented by the general formula (I[) used in the present invention is described in "Journal of Organic Chemistry J (G, C
, Denser, Jr., et al. - rJournal
of Organic Chemistry (/?1.A) Method described by Chi, P, Hildeutsch [Journal of the Chemical Society J (T, P.

Hilditch, rJourna 1 of
theChemical 5ocietyJ)? J
, /j2u~tjJ7 (/rior) method, or O.

By Hinsberg [O, by Hinsberg*
rBerichte der DeutschenCb
emischen Ge5ellschaftJ) Hiro?
It can be synthesized according to the methods described in , -2j ri 3 to koji rihiro (t?im). That is, in a sulfuric acid aqueous solution,
Cobalt(III) sulfate? A method of synthesizing from sulfinic acid represented by the general formula (]V) using ethyl xanthate? Using the method of synthesizing sulfonic acid chloride represented by the general formula (V), under basic conditions, the general formula (
Examples include a synthesis method in which a sulfinic acid represented by It) is reacted with a sulfonic acid chloride represented by the general formula (I[r).

R-8O2H (V) Noj, detailed lp drink (there is no wise brother in the content lR' -8O2
α (V) (Here, R and R' have the same meanings as R1 and R2 defined in the general formula (If).) Below, represented by the general formula (II) used in the present invention Specific compounds are illustrated below.

+I[-/) (■-ko) (II-3) (II-1) :“ (II-j) (■-bu) (If-7) (TI-4) (■-ta) (If- 10) N(h (It-//) (II-/co) (It-/r) (IF-/ri) (II-20) In addition, the photopolymerization initiator represented by the general formula (III) is G ,
F. Jaubert, Ber, 21.3AO(/I
P! r) (D method, D, E, Ames et al., J, C
hem, Soc,, J! /l (IPll) method, a ItsFiM, A., Stolberg et al., J.A.
mer.

Chem, Soc, , 7 F, Ko4/Evening (/1
17) f) A compound represented by the general formula (M) (where A is the same as the general formula (synonymous with IIN)) and R-8OxcJ (here, R is the compound represented by the general formula (IIN)) synthesized according to the method etc.
Same meaning as in case II). ) under basic conditions, for example, L , Bauer
et al., J. Org. Chem.

It is possible to synthesize nine pairs using the method of /λP3(/WO?>).

In the general formula (m), the arylene group h of A is preferably a monocyclic or cocyclic group, such as a phenylene group, a naphthylene group, etc.
Included are phenylene group, /, t-naphthylene group, co-, 3-naphthylene group, and the like. A human substituted arylene group is one having a substituent such as a halogen atom such as a chlorine atom or a bromine atom, a nitro group, or an acetylamino group on the above-mentioned arylene group, such as a bromophenylene group or a chlorophenylene group. , nitrophenylene group, acetylaminophenylene group, bromonaphthylene group, chloronaphthylene group, nitronaphthylene group, etc. It was,
The alkylene group of A is linear, branched and cyclic, preferably having from 7 to about 6 carbon atoms;
Examples include a methylene group, an ethylene group, a propylene group, a cyclobutylene group, a cyclohexylene group, and the like. The substituted alkylene group represented by A includes the above-mentioned alkylene group substituted with an aryl group such as phenyl group, such as phenylethylene group and diphenylethylene group. Further, the alkenylene group of A preferably has a carbon atom number of λ to μ, and includes, for example, a vinylidene group and a butenylene group. Further, the substituted alkenylene group of KA is an alkenylene group as described above substituted with an aryl group such as a phenyl group,
Examples include phenylvinylidene group, diphenylvinylizo7 group, and the like.

On the other hand, the alkyl group of R in general formula (III) is a straight chain, branched, or cyclic one, more preferably a straight chain, and preferably has /-11 carbon atoms, Examples include methyl, ethyl, butyl, hexyl, octyl, dodecyl, hexadecyl and other groups. In addition, the substituted alkyl group of R is the same as the above alkyl group.
For example, a halogen atom such as a chlorine atom, an alkoxy group having 7 to 1 carbon atoms such as a methoxy group, etc. can be substituted, and examples thereof include a cochloroethyl group, a -methoxyethyl group, etc. is included. Further, the aryl group of R is preferably a monocyclic or cocyclic group, and includes, for example, a 2-enyl group, a naphthyl group, and the like. In addition, the substituted alkyl group for R is an aryl group as described above, an alkyl group having 7 to 2 carbon atoms such as a methyl group or an ethyl group, or an alkyl group having 1 to 2 carbon atoms such as a methoxy group or an ethoxy group. Flukoxy groups, such as those substituted with halogen atoms such as chlorine atoms, are included, and specific V
Examples include ciPi methylphenyl group, dimethylphenyl group, methoxyphenyl group, chlorophenyl group, methoxynaphthyl group, and the like.

Specific examples of compounds represented by the general formula (m) used in the present invention are illustrated below.

(III-/) (III-J) (III-J) <m-1A) (l[-j) 111.5・ j −〇 (■～6) (]l[-10) (m-//) (III-/, 2).

(■-/J) (III-74') (III-/l) I (DI-/A) (l[-/r) (Il[-/P) (■-koO) /) (■-Coco) (■-Co3) The ratio of the compound that can generate silicic acid upon irradiation with actinic rays and the compound that has at least one silyl ether group that can be silyolyzed by the acid is , weight ratio 0.00/:/
-,2:/demeshi, preferably 0.0-22l~0.1
Used with :/.

The photo-soluble composition of the present invention can be used only in combination with a compound capable of generating silicic acid upon irradiation with actinic rays and a compound having at least one silyl ether group capable of being oxidised by an acid. However, it is preferable to use it in combination with an alkali-soluble resin. Suitable alkali-soluble resins include novolak-type phenolic resins, specifically:
Included are phenol formaldehyde resin, o-cresol formaldehyde resin, m-cresol formaldehyde resin, and the like. Furthermore, as described in Japanese Unexamined Patent Application Publication No. 1983/1983, in addition to the above-mentioned phenol resins, phenol or cresol substituted with an alkyl group having a carbon number of 3 to t, such as t-butylphenol formaldehyde resin, can be used. It is more preferable to use a condensate with formaldehyde in combination. The alkali-soluble resin is present in an amount of about μO to about 0% by weight, preferably to-, r-o% by weight, based on the total weight of the photosensitive resist-forming composition.
Contained.

The photosoluble composition of the present invention may further include a dye, if necessary.
Suitable dyes that can contain pigments, plasticizers, and compounds that increase the acid generation efficiency of the acid-generating compound (so-called sensitizers) include oil-soluble dyes and basic dyes. Specifically, oil yellow #10/,
Oil yellow @/30. Oil pink @J /
J, Oil Green BG, Oil Blue BO8, Oil Blue #603, Oil Black BY, Oil Black BS2 Oil Black T-401 (Orient Chemical Industry Co., Ltd. #Crystal Violet (CI4L)
attt), methyl violet (CIu2z3z),
Rhodami YB (CI4CJ/70B), malachite green (CI4C 000), methylene blue (Cat COIZ), etc. can be mentioned.

The photosoluble composition of the present invention is dissolved in a solvent that dissolves each of the above components and applied onto a support. The solvents used here include ethylene dichloride, cyclohexanone, methyl ethyl ketone, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether,
Examples include comethoxyethyl acetate, toluene, and ethyl acetate, and these solvents can be used alone or in combination.

And the concentration in the above ingredients (total solid content including additives) is:
λ~! O weight %. Among these, the preferred concentration (solid content) of the composition of the present invention is 0.1-21% by weight. In addition, the coating amount varies depending on the application, but for example, for photosensitive planographic printing plates, if b5, the solid content is generally θ, j~J,
01/WL2 is preferred.

As the coating amount decreases, the photosensitivity increases, but the physical properties of the photosensitive film deteriorate.

When producing a lithographic printing plate using the photosoluble composition of the present invention, the support may be a hydrophilized aluminum plate, a silicate-treated aluminum plate, an anodized aluminum plate, or a grained aluminum plate. , silicate electrodeposited aluminum plate, other lead plate,
Stainless steel plates, chromium-treated steel plates, hydrophilized plastic films and paper can be used.

Supports suitable for producing printing proof plates, overhead projector films, and 4th original films include transparent films such as polyethylene terephthalate film and triacetate film, and the surfaces of these plastic films are chemically or physically matted. I can give you what I have transformed into. Supports suitable for producing photomask films include polyethylene terephthalate films deposited with aluminum, aluminum alloys, and chromium, and polyethylene terephthalate films provided with colored layers.

The photoresist composition of the present invention can also be used as a photoresist by coating it on various supports other than those mentioned above, such as steel plates, copper-plated plates, and glass plates.

Examples of active light sources used in the present invention include 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) K can also be used in the present invention. Such laser beams include helium neon lasers, argon lasers, krypton ion lasers, and helium neon lasers.
Examples include cadmium lasers.

Examples of developing solutions for the photosoluble composition of the present invention include sodium silicate, potassium silicate, sodium hydroxide, potassium hydroxide, lithium hydroxide, tribasic sodium phosphate, dibasic sodium phosphate, tribasic ammonium phosphate, dibasic diphosphate, Aqueous solutions of inorganic alkaline agents such as ammonium acid, sodium metasilicate, sodium bicarbonate, aqueous ammonia, etc. are suitable, such that their concentration is o, i, io, preferably 0.001 to 1% by weight. added to.

1*. If necessary, a surfactant or an organic solvent such as alcohol can be added to the alkaline aqueous solution.

"Examples" The present invention will be explained in more detail below with reference to Examples, but the content of the present invention is not limited thereto.

Example 1 A λS aluminum plate with a thickness of O04 am (filter phosphoric acid maintained at O'CK) was degreased by immersing it in a 10% aqueous solution of IJum for 3 minutes, grained with a nylon brush, and then etched with sodium aluminate for about io seconds. Then, perform desmut treatment with a 3% aqueous solution of sodium hydrogen sulfate.9. This aluminum plate was heated at a current density of λA/dm in 20% sulfuric acid.
An aluminum plate was produced by performing anodic oxidation between the parts.

Next, by changing the type of compound (a) of the present invention in the following photosensitive liquid (A), three types of photosensitive liquid (A)-/~[A]-! This photosensitive solution was applied onto an anodized aluminum plate and dried for a few minutes with too'c to form each photosensitive lithographic printing plate [A)-/~(A'J-j. The dry weight of all coatings at this time was /, jf/m2.

Further, Table 1 shows the nine compounds (a) of the present invention using the photosensitive liquid (A)-/-(:A)-7ic.

Photosensitive liquid (A) Compound (a) of the present invention (a) 0, μOt cresol-formaldehyde novolac resin /, l f Compound (b) of the present invention (■-koλ) o, art oil blue #t03 (manufactured by Orient Chemical Industry ■) ) o, oiy ethylene dichloride 10f methyl cellosolve
io1 Next, as a comparative example, the following photosensitive liquid [
B'3 was applied in the same manner as photosensitive liquid [A] to prepare a photosensitive lithographic printing plate [B].

Photosensitive liquid CB) Cresol-formaldehyde novolac resin and 7. λ-naphthoquinone--diazido! -Condensation product with sulfonyl chloride o, 4try cresol-formaldehyde novolac resin i, i yl, conabutoquinone-2-di 0.0 co? Acid-μm sulfonyl chloride oil blue #tOJ (manufactured by Orient Chemical Industry ■) o, oty ethylene dichloride 10f methyl cellosolve
The coating weight after drying is / , j
It was t/m2.

A gray scale with a VCQ degree difference of 0./j was brought into close contact with the photosensitive layer of the photosensitive lithographic printing plates (A]-/~[A]-1 and [B], and exposed from a distance of 70 cIIL with a 30 ampere carbon arc lamp. Go nine.

Photosensitive lithographic printing plates [:A]-/~I:A]-7 and CB]'tDP exposed to show excellent photosensitivity of the present invention
-μ (product name: manufactured by Fuji Photo Film ■) was immersed and developed for 60 seconds at COZ'C with a t-fold diluted aqueous solution, and the density difference was 0.
．． The exposure time at which the first stage was completely clear on the /j gray scale was determined and was as shown in Table 1.

Table 7 Compounds (a), I-j, / of the present invention in Table 1
/, , /A1.2t, uo, n=Q, x/y=4A
o7to<molar ratio) was used. All molecular weights were determined by GPC (Gel PermeationChrom).
atography) polystyrene standard 2!00~z
It was from ooo.

As shown in Table 1, the photosensitive lithographic printing plate (A) using the compound of the present invention -/~ [:A] -j is - [B]
Less exposure time and higher sensitivity.

Example 2 In the following photosensitive liquid [C], the types of the compounds of the present invention that can generate acids upon irradiation with actinic rays were changed, and the following photosensitive liquids [C]-/~(C]-4' were prepared. A photosensitive lithographic printing plate (C]-/~[C]-μ was prepared in the same manner as in Example 1.
was created.

Photosensitive solution (“C) Compound of the present invention (a) (I −/co) o, 3ty
Cresol-formaldehyde novolac resin i, o y Compound (b) of the present invention o, o zy Oil Blue (manufactured by Orient Chemical Industry ■) o, oiy Ethylene dichloride 10f Methyl cellosolve
All ioy coating amounts are dry weight.
j f / @2. Note that the photosensitive solution (compound (a) of the present invention used in CHI (I −/λ) is H=
IA, X / y = u O / l O (molar ratio), molecular weight is 3.1 by GPC, polystyrene standard
It was 00. Table 2 shows the compounds (b) of the present invention which generate acids upon irradiation with actinic rays and which were used in photosensitive solutions [C]-7 to [C]-≠.

A gray scale with a degree difference of 00 ip was adhered to the photosensitive layer of the photosensitive lithographic printing plate [:C]-/~[C]-μ and the photosensitive layer prepared in Example 1. Exposure was carried out with a lamp from a distance of 70 cIIL.

2j'C with a 1-fold diluted aqueous solution of exposed photosensitive lithographic printing plates (C)-/~(C)-μ and (B:I'rDP-t,t (product name: manufactured by Fuji Photo Film ■). After immersion development was carried out for 10 seconds, the exposure time at which the third stage was completely cleared in the gray scale with the density difference o and is was determined, and the results were as shown in Table 2.

(・:' As shown in Table 2, all of the good-bad light lithographic printing plates (C)-/~(C)-μ using the compounds of the present invention have a longer exposure time than [B]. small amount and high sensitivity.

Patent Applicant Fuji Photo Film Co., Ltd. Procedural Amendment (Indication of Blade Case 10, 1985, Patent Application No. 7017)
No. 2, Title of the invention Previous solubilized composition 3, Relationship to the amended person's case Name of patent applicant (520
) Fuji Photo Film Co., Ltd. Date of amendment order
Month 30, 1933 (shipment date) & Subject of amendment Replace column 6 of the "Detailed Description of the Invention" of the specification, Contents of the Amendment, No. 1, page 1 with an attached sheet.

Claims (1)

[Scope of Claims] (a) It has at least one acid-decomposable silyl ether group represented by the following general formula (I) in the molecule, and its solubility in a developer increases by the action of an acid. Compounds, and ▲mathematical formulas, chemical formulas, tables, etc.▼(I) (b) Compound R_1-SO that can generate an acid when irradiated with actinic rays and is represented by the following general formula (II) or (III)
_2-SO_2-R_2 (II) In the formula, R_1 and R_
2 each independently represents an aryl group or a substituted aryl group ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (III) In the formula, A is an arylene group, substituted arylene group, alkylene group, substituted alkylene group, alkenylene group, substituted Represents an alkenylene group. A photo-solubilizing composition characterized in that R represents an alkyl group, a substituted alkyl group, an aryl group, or a substituted aryl group.