JPS61169837A - Photosolubilizable composition - Google Patents

Abstract

PURPOSE:To obtain superior photosensitivity, wide development latitude, and good printing resistance by using a compsn. composed of a compd. producing acid upon irradiation of actinic rays, and a compd. having a silyl ether group decomposable with acid. CONSTITUTION:The compsn. is composed of the compd. capable of producing an acid upon irradiation of actinic rays represented by formula II or III, R1 being aryl, alkenyl, or the like, R2 being R1, -CX3, or alkyl, and X being Cl or Br, and a compd. having at least one silyl ether group decomposable with acid in the molecule represented by formula I, thus permitting the obtained positive type photosensitive material to be high in photosensitivity, wide in development latitude, superior in storage stability, storable for a long term, superior in printing resistance, simple and easy in manufacture, and usable for a lithographic plate, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION "Industrial Application Field" The present invention relates to a photo-solubilizable composition suitable for the production of lithographic printing plates, proofs for multicolor printing, drawings for overhead projectors, IC circuits, and odomasks. For more details, see (
The present invention relates to a novel photo-solubilized composition containing: a) a compound capable of generating silane upon irradiation with actinic rays; and (b) a compound having at least one crylic ether group capable of being decomposed by rRK.

"Prior Art" Orthoquino/diazide compounds have been known as photosensitive substances that act so-called positiso and are solubilized by actinic rays, and have been widely used in lithographic printing plates, photoresists, and the like. Examples of such orthoquinone diazide compounds include, for example, US Pat. No. 744. //r
No., same No. ko.

7t7,0 Octopus, No.-177, No. 27, No. 112, No.-1, No. 07,411, No. 3. out, ito issue, same number J, 0 pi 1,111, same number J, 0 reference t, //! r number, same number i, otat, iir
No. 3. ou4. ii No. 2, same No. 3,0444, 1
No. 20, @J, 01fi4, /ko1, No. J, 0hi4. / Ko No. 3.0 Hiroj, No. 713, No. 3.0
≦l, ≠JO No. 3, 10, tori No., JO No.
10 ots.

≠t1 No. J, tJ! , 70? No. 3, Hiroshi 7
．． It is described in numerous publications, including the specifications of No. 3.

These orthoquinonediazide compounds decompose when exposed to active light! These methods take advantage of the fact that they produce ring-membered carboxylic acids and are soluble in alkali, but they all have the disadvantage of insufficient photosensitivity. This is because, in the case of orthoquinone diazide compounds, the quantum yield essentially does not exceed 1.

Various attempts have been made to increase the photosensitivity of photosensitive compositions containing orthoquinone diazide compounds, but it has been extremely difficult to increase photosensitivity while maintaining the current tolerance. there were. For example, an example of such an attempt is Tokuko Shosan! -/Coco4cco, Tokukai Akira! Ko≠0/2! No., U.S. Patent WJ≠, 307. /7J
Examples include the contents described in the specifications such as No.

In addition, recently, several proposals have been made regarding photosensitive compositions that act in a positive direction without using an orthoquinone diazide compound. One example is Tokko Akira! t-
Polymer compounds which grow orthonitrocarbinol ester groups are mentioned in the specification of No. 2ty≦. 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, we also use a photosensitive system that is activated by contact action,
As a method of increasing photosensitivity, the known principle of causing the first reaction with an acid generated by photolysis and thereby solubilizing the exposed region is applied.

Examples of this include, for example, a combination of a compound that generates an acid by photolysis and an acetal or O,N-acetal compound (4?Kaisho≠r-rri00co), or a combination of an orthoester or an amide acetal compound. The combination of Japanese Patent Publication No. 1
/-/ko07/≠), a combination with a polymer having an acetal or ketal group f in the main chain (JP-A-ShojJ-/J3
No. 11), combination with enol ether compound %
Kaisho! ! -l Kotata! (No.), combination with N-acyliminocarbonic acid compound (No. % Kaishojj-/Cot13), and combination with polymer having orthoester group fcV in the main chain. (No.). In principle, these have a quantum yield exceeding 1, so they may exhibit high photosensitivity, but in the case of acetal or 0,N-acetal compounds, and in the case of polymers having acetal or ketal groups in the main chain Because the rate of the second reaction with the acid generated by photolysis is slow, it does not produce enough photosensitive gold for practical use. In addition, orthoester or amide acetal compounds, enol ether compounds, and even N-acylimino carbonate compounds do exhibit high photosensitivity, but they are not stable over time and cannot be stored for long periods of time. Poly-i-, which has an orthoester group in its main chain, also has high sensitivity, but has the disadvantage of narrow current tolerance.

"Problems to be Solved by the Invention" The purpose of this research is to provide a novel photo-solubilizable composition in which these problems are solved. That is, it is an object of the present invention to provide a novel photo-solubilizable composition which has high photosensitivity and wide tolerability in the field.

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 has developed the present invention. Reached.

That is, the present invention provides (a) a compound capable of generating a total acid upon irradiation with actinic rays, and (b) a compound having at least one silyl ether group represented by the following general formula (1) in its molecule and capable of being decomposed by an acid. , wherein the compound capable of generating an acid upon irradiation with actinic rays is a compound represented by the following general formula (n) or (III). It is something that provides something.

Here, in the formula, Ro represents a substituted or unsubstituted aryl or alkenyl group, and R2 represents a, -CX3, or a substituted or unsubstituted alkyl group. X represents a chlorine atom or a bromine atom.

Examples of the compound represented by the general formula (II) used in (a)K of the present invention include JP-A-744-7μ72, JP-A-777μλ, and JP-A-Sho!?-
Examples include compounds described in iur'yrμ publication. Specific examples of the compound in (a) of the present invention include the following compounds. α Muko Ako! Muko t A core flat t CH3 A Kota 6JO ni l-13 &J/ Mu3ko JJ AJ Hiro AJ! Grave J4 Mu J7 Examples of the compound represented by the general formula (l[I) used in (a) of the present invention include, for example, the compound described by Chittai et al., Bull.

Chem, 8oc, Japan, Volume≠2,
Examples thereof include the compounds described in Co., Ltd., page K, US Pat. Variants include the following compounds.

& Jr. A3ri Cα3 M4LO Cα3 Muhiro CB r a Mudako CB r 3 ct3 Cα3 Ken 4c A≠7 A! O Cα.

black! l Cα3 Cα3 CCI? 3 Cα3 The compound having an acid-decomposable silyl ether group represented by the general formula (t) used in (b) K of the present invention preferably contains a repeating unit of the following general formula (IV). Features.

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

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

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

÷OH, Of(, -0+.

-1-+-CH2+-,0 coating CE(,CH,-0+-1
.

In the formula, l represents an integer from 1 to 0, and m and n represent an integer of 0 or more, preferably an integer of 0 to 100, and more preferably an integer of 0 to 0. R represents alkyl or a phenyl group which may have a substituent.

A particularly preferred hydrophilic group is ÷CH2C)12-0+.

It is.

R4 and FL may be the same or different, and each represents a hydrogen atom, an alkyl, an alkenyl, an aryl or aralkyl which may have a substituent, or -oa, t-
show. Preferably alkyl having l-hi carbon atoms, or -O
R,t-indicates. R6 represents an alkyl, aryl, or aral group which may have a substituent t'', preferably an alkyl group having /-r carbon atoms, or an aryl group having 6 to is carbon atoms.

Further, the compound used in the present invention may contain one or more types of repeating units represented by the general formula (■I).

Specific examples of the compound in Φ)K of the present invention include those shown below.

A/ Ako Aμ ni? 13 to ti3 handle
N'4v4!1! ! 0 ro ro fake yoke
\ku '4
4\ P111'1'1S
N
\beak
Kugure 4N1
Supplement "4 礪 Wife 4 Indicates an integer greater than or equal to ntiz in the specific example of agony. Also, 1
)'% Z indicates molar ratio, Compound Example A Kotar-JO1
In J3, x=10-11 mo AILfk, y=z~rO mole%, z=10-1 rj mole. Also, compound example A
t~/J, II, J7~. ．． ? r% J4, J! , and in 37~uo x=! NPO mol%, y=io~ri! Shows mol%.

The weight ratio of the compound capable of generating an acid upon irradiation with actinic light in (a) of the present invention and the compound having at least one silyl ether group capable of being decomposed by an acid in (b) is 0.001:/ It is preferably used at 0.0λ:l~o, r:i.

The pre-soluble composition of the present invention can be used only in combination with the above-mentioned compound capable of generating an acid upon irradiation with actinic rays and a compound having at least one silyl ether group that can be decomposed by an acid. 1. It is preferable to use it in combination with an alkali-soluble resin. Suitable alkali-soluble resins include novolak-type phenolic resins, and specifically include phenol formaldehyde resins, 0-cresol formaldehyde stm, m-cresol formaldehyde resins, and the like. Furthermore, 411F Kaisho jO-
As described in the Kojrot publication, in addition to the above-mentioned phenol resins, a condensation product of phenol or cresol substituted with an alkyl group having 3 to t carbon atoms, such as t-butylphenol formaldehyde resin, and formaldehyde. It is even more preferable to use both together. The alkali-soluble resin has a weight of about 0.000 to about 0.0000000000000000000000000000000000000000000 Yen based on the total weight of the photosensitive resist-forming composition, more preferably 60 to 0.0000000000000000000000000000000000000000000000000000000000000000000000000000000000001
It can be contained in an amount of 0% by weight.

The photosoluble composition of the present invention may further include a dye, if necessary.
A pigment, a plasticizer, a compound that increases the acid generation efficiency of the acid-generating compound (so-called sensitizer), etc. can be contained. Suitable dyes include oil-soluble dyes and basic dyes. Specifically, oil yellow g10/,
Oil yellow fj/30, oil pink gJ/co, oil green/BG, oil blue BO8, oil blue 603, oil black BY, oil black BS
1 Oil Black 'I'-40t (manufactured by Orient Chemical Industry Co., Ltd.) Crystal Violet (CI4)
'Ko! ! j), Methyl Violet (CI Sanko! 3!)
, Rhodamine B (CI Hiroj/70B), Malachite Green (CIμ4000), Methinone Blue (CIj Koo
tB etc. can be given.

The photosoluble composition of the present invention is dissolved in a solvent that dissolves each of the above components and applied onto a support. Examples of the solvent used here include ethylene dichloride, cyclohexanone, medel ethyl ketone, ethylene glycol monomethyl ether, ethylene glycol heptanoethyl ether, -1-methoxyethyl acetate, toluene, and ethyl acetate. Mix and use.

The concentration of the above components (total solids including additives) is
2 to 30% by weight. Among these, the preferable 11 degrees (solid content) of the composition of the present invention is O0l to CojJl amount.

The coating amount varies depending on the application, but for example, for photosensitive planographic printing plates, the solid content is generally O,j~J
, 077m 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 an aluminum plate treated to make it hydrophilic, such as a silicate-treated aluminum plate, an aluminum oxide plate, or a grained aluminum plate. , Noricate electrodeposited aluminum plate, other zinc plates,
Stainless steel plates, chromium-treated steel plates, hydrophilized plastic films and paper can be used.

Supports suitable for producing printing proof plates, films for overhead projectors, and films for second originals include transparent films such as polyethylene terephthalate film and triacetate film, and the surfaces of these plastic films are matted chemically or physically. I can give you what I have transformed into. Supports suitable for producing photomask films include aluminum and aluminum 9A.
Examples include polyethylene terephthalate film on which an alloy or chromium is vapor-deposited, and polyethylene terephthalate film on which a colored layer is formed.

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

Examples of active light sources used in the present invention include mercury lamps, metal halide lamps, seminone lamps, chemical lamps, and carbon arc lamps. Scanning exposure with a high-density energy beam (laser beam or electron beam) is also useful in the present invention. Such laser beams include helium neon lasers, argon lasers, krypton ion lasers, and helium neon lasers.
Examples include cadmium lasers.

Developers for the photosoluble composition of the present invention include sodium silicate, potassium silicate, sodium hydroxide, potassium hydroxide, Lytecum hydroxide, sodium tertiary phosphate,
Aqueous solutions of inorganic alkaline agents such as sodium diphosphate, triammonium phosphate, ammonium diphosphate, sodium metasilicate, sodium bicarbonate, aqueous ammonia, etc. are suitable, and their # degree is 0. /-10% by weight, preferably 0.1-7% by weight.

Moreover, a surfactant and an organic solvent such as alcohol can be added to the alkaline aqueous solution as required.

“Example” Below is the original F! The present invention will be explained in more detail using At-synthesis examples and examples, but the content of the present invention is not limited thereto. Synthesis example /-// is (b) K of the present invention
The synthesis method of the compound used is shown.

/, r-rkta/di, to -7.321(0,Ol
oimole), Tetraethyl V/Glycoulta.

7/-r (0,0!00mole), pyridi7/7゜μ
2 (O, here Omole), dehydrated distilled toluene rO
5 dichlorodimethyl 7 runs/J to a mixture of zl, ry(
A solution of 10 wl of toluene of O.ioomole) was added from the dropping funnel over 30 minutes while stirring and cooling on ice. After the addition, stirring was continued for 3 hours at 1c. The produced white salt (pyridine hydrochloride) was separated from P, and the toluene solution was concentrated under reduced pressure. Thereafter, under vacuum (approximately / mmHg)
9. Dry for io hours with heating for about lO@CK. Colorless and transparent liquid, yield: 0.7f6NMEL, its structure is a compound example &! It was confirmed that Furthermore, VPU(V
apour pressure osmomete
When the number average molecular weight was measured using r), it was found that Mn=/rito.

Instead of 1, l-octanediol in Synthesis Example 1, 1.7 cof (o, oroom
ole)f was used, and the reaction and post-treatment were carried out in the same manner as in Synthesis 99/. The structure was confirmed to be Compound Example 44 by colorless transparent liquid, yield -1, zt6NMB, and v
When the number average molecular weight was measured by PO, Mn=irz
It was o.

1 each in place of 1lt-octanediol and tetraethylene glycol in Synthesis Example/.

≠−Cyclohexanediol! , r/f(0, OjOO
mole), polyethylene glycol #Co00 (manufactured by Kanto Kagaku ■, average molecular weight Co00) IO? (0,0!Omol
e) t- was used, and the reaction and post-treatment were carried out in the same manner as in Synthesis Example 1. Colorless transparent viscous liquid, yield 15', 7f, NM[1,
The structure is confirmed to be the compound example mt, and v
When the number average molecular weight was measured using POK, it was found that Mn=/4Q.

In place of l, t-octanediol and tetraethylene glycol in Synthesis Example 1, p-medium silylene glycol J, ! J f (0, Ouomole)
, polyethylene glycol 3300 (manufactured by Kanto Kagaku ■, average molecular weight JOO)/If (0°640 mole) t- was used, and the reaction and post-treatment were carried out in the same manner as in Synthesis Example 1. It was a colorless transparent viscous liquid, the yield was λt, and it was confirmed by rfoNMB that the structure was that of Compound Example Mulco, and when the number average molecular weight was measured by vPO, it was found that Mn=i73o.

Synthesis Example 5 (Synthesis of Compound Example A/7) Dihydroxyethylnohydroquinone/di, P9(0,
/+70mole), Piriji7/7.1lf (OlJ,
27 mole) of dichlorodimethylsilane to a mixture of 1 t of dehydrated and distilled toluene solution.

The toluene Od solution of f(0,100m01e) is
It was added in the same manner as in Synthesis Example 1, and then the reaction and post-treatment were carried out in the same manner. Slightly brownish white solid, yield: 7
The structure was confirmed to be Compound Example &I7 by yeNM, and the number average molecular weight was measured by VP(J), and it was found that Mn-CoO≠0.

Synthesis Example 6 (Synthesis of raw materials for Compound Example A and O) Add a catalytic amount of pyridine to Edele/Glycol/llIc, and add 2.
≠-Tolylene diisocyanate 73PF was added from the dropping funnel over a period of about 10 minutes with stirring. After the addition, stirring was continued for an additional 2 hours at 70°C. Thereafter, the reaction solution was cooled in an ice-methanol bath to precipitate a white solid. After separating F, it was recrystallized with about 1 liter of water to obtain white crystals uf (yield: yoqb). NMR and elemental analysis confirmed that the white crystals were bis-(diethyl in J-hydro)co,μ-tolylene dicarbamate.

A catalytic amount of triethylamine was added to seven ethanolamine/l, and 1. Reference-tolylene diisocyaner)/J
2 was added from the dropping funnel over about 1 hour while stirring. After the addition, stirring was continued for an additional 7 hours at to'c. The produced white solid t-F was separated and recrystallized from about 3/l of water. White crystals 1zt2 (yield t6chi) f: Obtained. NMR and elemental analysis revealed that this white crystal was 2. Hiro - Trinon -
Bis-(cohydroxyethylcarpamite) was confirmed.

Synthesis Example 8 (Synthesis of Compound Example A and O) Bis-(-monohydroxyethyl) obtained in Synthesis Example jK,
≠-Tolylene dicarpamate coy, 1t (0,100m
ole), Piriji 7/7. uf(O,JJOmOle)
was stirred in ethyl acetate Ir0w at room temperature, and dichlorodiethylsilane l was added.

A toluene solution of Wf (0,100 m01e) was added from the dropping funnel. The addition took approximately 30 minutes. After addition, continue to stir for 3 hours at JO''C.

After separating the Hα salt of pyridine produced by F, the reaction solution is!
-Na HCOs aqueous solution 200g1. Furthermore, it was washed with saturated saline solution and dried with Na 2 S 04. Thereafter, the reaction solution was dried by #condensation, and as a result, a colorless resin Jlf was obtained. NMR confirmed that the structure was Compound Example A. Further KGPC (Gel Pe
When the molecular weight was measured by rmation chromatography), it was found to be 4c using a polystyrene standard.
, it was zoo.

Synthesis Example 9 (Synthesis of Compound Example MJ7) Bis-(-monohydroxyethyl)m-xylene dicarpametone glycol obtained by the same method as Synthesis Example 4 was concentrated and then concentrated using a water cup crystal. )/r.

79 (0, OAoomOle), p-xylylene glycol j, If (0,0+00mole), pyridine iy
, IAf (0-coco0 mole) of ethyl acetate/rOw
The reaction and post-treatment were carried out by the method shown in Mixture Gold Synthesis Example t.

A colorless viscous liquid was obtained. The structure was confirmed to be the compound core by NMR, and further GP
When the molecular weight was measured by C, it was 100 using a polystyrene standard. Synthesis f[3io (Compound Example, Synthesis of If&3)
ethylcarpamide)t, rif(0゜OjOOmole)
, tetraethylene glycol/J, 4f (0,0700
m01e), pyridine/7.44? (0, here omo
The ethyl acetate Ir0w1 mixture of l e ) was reacted and worked up in the same manner as in Synthesis Example t. A colorless viscous liquid cocof was obtained. According to NMR, the structure is Compound Example 7
After confirming that it was fLJ, we further analyzed the molecular weight using GPC, and found that it was /,! with a polystyrene standard. It was 00.

Bis-(diethyl in cohydro)isophthalate (O0/
(70 mole), Virigi 7/7, 4cf (0, Coco O
dichlorodiethylsilane/! to 100ml of toluene solution of mole). , 7f (0,100 mol) of a toluene, 20-solution was added through the dropping funnel at room temperature with stirring over a period of about J0 minutes. 1 at to”c after addition
Stirring was continued for an hour.

After separating the H (jtF) of the generated pyridine, post-treatment was performed in the same manner as shown in the synthesis IPIIF to obtain a non-male viscous liquid core 21. NMRK revealed that the structure was that of Compound Example 53.
It was confirmed that the molecular weight was 1, and the molecular weight was further measured by GPC, and it was found to be J,000 using a polystyrene standard.

Example 1 A CoS aluminum plate with a thickness of 00.2 μmm was heated at 10thC.
It was degreased by immersing it in a 10% aqueous solution of tribasic sodium phosphate maintained at a temperature of 300 ml for 3 minutes, then grained with a nylon brush, etched with sodium aluminate for about 10 seconds, and then completely desmutted with a 3% aqueous solution of sodium hydrogen sulfate. . This aluminum plate was heated at a current density of 2 A /
Anodizing was performed for λ minutes at d m to produce an aluminum plate.

Next, the type of compound (a) of the present invention was changed in the following photosensitive solution (A) to adjust l/type of photosensitive solution (A) -t to [person] -//f, and this photosensitive solution was anodized. The photosensitive solution (A) was coated on an aluminum plate and dried for 2 minutes with ioo"C to prepare the respective photosensitive ftti lithographic printing plates [A]-1 to [person]-//l-. As the compound (b) of the present invention, a compound represented by the compound A and O was used.The molecular demon is GPC (Gel Permeation Chr
omatography) with polystyrene standards, 10
It was 0. The amount of coating at this time is all dry weight /, 1
It was 97m”.

The compounds (a) of the present invention used in photosensitive solutions (A)-/ to (A)-// are shown in Table 1.

Photosensitive liquid (A) Next, as a comparative example, the following photosensitive liquid CB) t-photosensitive liquid (A)
A photosensitive lithographic printing plate CB) was prepared by coating in the same manner as above.

Photosensitive liquid CB) The coating weight after drying is /,! It was f/fn.

, photosensitive lithographic printing plate (A)-/~(A)-// and C
There is a density difference of 0 on the photosensitive layer of B). l! 70C1M with a 30 ampere carbon arc lamp in close contact with gray cool.
Exposure was carried out from a distance of .

Photosensitive lithographic printing plates exposed to show the excellent photosensitivity of the present invention (A) -/~[Person] -// and CB) t-DP-
1 (trade name: manufactured by Fuji Photo Film ■) with an r-fold diluted aqueous solution at 2z0C for 60 seconds and developed, with a # degree difference of 0. /
! (With Q gray scale!) After finding the exposure time to make the rows completely clear, the result was as shown in Table 1.

Table 1 As shown in Table 1, photosensitive lithographic printing plates (A)-/~[person]-// are all CB) using the compound of the present invention.
Less exposure time and higher sensitivity.

Implementation f! J2 Photosensitive lithographic printing was carried out in the same manner as in Example 1 using (A)-/Col[λ]-/7f in which the compound of (b) of the present invention was changed in the photosensitive solution (A) of Example 1. Plate (A)-/Col (A)-/7 was produced. As the compound (a) of the present invention in the photosensitive solution (A), the compound shown in Compound Example Aio was used. All coating amounts are dry weight /, 197
m".Also, photosensitive liquids (A)-/2 to (A)-77
The compounds of the present invention used in Table 4 are shown in Table 4.

Photosensitive lithographic printing plates (A)-/J to (A)-77 and CB
)t-Execution fFIIl Exposure and development*1-Execution, density difference 0. l! The exposure time for making the third row completely clear on the gray scale was determined and the results were as shown in Table 1.

Table 2 Compounds of the present invention in Table 1 Am;, /co, /I
Then x / y x j O / j O (molar ratio), n
= uO was used. AJ Ri de x/y/
The one with z=JO/107410 (molar ratio) was used. The molecular weight of the compounds of the present invention in Table 2 is 7g.
66,/-1it is VPU (V, 5pour Pr
essureUsmometer) dettoo~
Ko100. I & Coco, Kota, 31 are GPC, polystyrene standard from 2j00! 000.

As shown in Table 1, all of the photosensitive lithographic printing plates (A)-icol (A)-/7 using the compounds of the present invention are CB
), the exposure time is shorter and the sensitivity is higher.

Example 3 Photosensitive solution of Example 1 (A)-j, C person)-10° and (A
)-z and (A)-to, a photosensitive lithographic printing plate was prepared in the same manner as in Example 1 using the photosensitive liquid (C)-/-co in which only the compound (a) of the present invention was replaced with another compound. (A)-
j, C person)-/os (C)-l ~ Ko7 were created. The amount of coating was 97 m/j on dry weight. In addition, the compound used in the photosensitive liquid [C]-7-co was
Shown in the table.

In order to check the stability over time, photosensitive planographic printing plates (A)-r, (
A) −/0, (C) Immediately after preparing −t−1, and Temperature Hiro! @C1 After being left for 3 days under the condition of humidity 7j,
Exposure and development were carried out by the method shown in Example 1, and the density difference was 0.7! The exposure time for making the third row completely clear on the gray scale was determined and the results were as shown in Table 3.

As shown in Table 3, photosensitive lithographic printing plates (A)-t and (A)-t o using the compound of the present invention were left for 3 days immediately after preparation and under conditions of temperature 1Az"c and humidity 7j-. There is no difference in subsequent exposure time, and the stability over time is excellent.

Patent Applicant: Fuji Photo Film Co., Ltd. Procedural Amendment Showa “0 year r ship Q day

Claims (1)

[Scope of Claims] (a) A compound capable of generating an acid upon irradiation with actinic rays; and (b) at least one silyl ether group represented by the following general formula (I) in the molecule and capable of being decomposed by an acid. A photo-solubilizable composition containing a compound having the following formula (II) or (III), wherein the compound capable of generating an acid upon irradiation with actinic rays is a compound represented by the following general formula (II) or (III). Solubilizing composition. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) Here, in the formula, R_1 is substituted or unsubstituted. aryl,
The alkenyl group R_2 represents R_1, -CX_3, or a substituted or unsubstituted alkyl group. X represents a chlorine atom or a bromine atom.