JPS63226641A - Photosensitive composition - Google Patents

Abstract

PURPOSE:To obtain a photosensitive compsn. giving a planographic printing plate having high printing resistance by using a polymer having active imino groups, insoluble in water and soluble in an alkali soln. CONSTITUTION:This photosensitive compsn. contains a polymer having active imino groups, insoluble in water and soluble in an alkali soln. The polymer has structural units represented by formula I or II. In the formula I, A is H, halogen atom or 1-4C alkyl group, B is alkylene, phenylene, substd. alkylene or substd. phenylene group, X is a group represented by formula III, Y is a group represented by formula IV or -R<1>, each of (m) and (n) is 0 or 1 but (m) and (n) are not simultaneously 0 and the imino group bonds directly to at least one carbonyl or sulfonyl group in X and Y. In the formula II, E is H, halogen atom, 1-4C alkyl or phenyl group, each of F and G is alkylene or substd. alkylene group, each of (p), (p'), (q) and (q') is 0 or 1 and at least one of (q) and (q') is 1.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a photosensitive composition suitable for manufacturing lithographic printing plates, IC circuits and photomasks.

More specifically, it relates to a photosensitive composition comprising a photosensitive compound such as an 0-naphthoquinone diazide compound and a polymer soluble in an alkaline aqueous solution or an alkaline solvent mainly composed of water (hereinafter referred to as alkaline water soluble).

[Conventional technology]

A photosensitive composition composed of an 0-naphthoquinone diazide compound and a novolak type phenol resin has been used industrially as an extremely excellent photosensitive composition in the production of lithographic printing plates and as a photoresist.

However, due to the nature of the novolak-type phenolic resin used as the main material, it has poor adhesion to the substrate, brittle film, poor abrasion resistance, and insufficient stiffness when used in lithographic printing plates, etc., which should be improved. However, there were some limitations in terms of application.

In order to solve this problem, various polymers have been investigated as binders. For example, Tokuko Sho 52-410
Although the polyhydroxystyrene or hydroxystyrene copolymer described in Publication No. 50 did have improved film properties, it had the drawback of poor abrasion resistance. Furthermore, in JP-A-51-34711, it is proposed to use a polymer having a structural unit of an acrylic acid derivative in its molecular structure as a binder, but it is said that such a polymer has a narrow range of appropriate development conditions. There was a problem.

[Problem that the invention seeks to solve]

Therefore, an object of the present invention is to provide a photosensitive composition that can be used in a wide range of appropriate development conditions and provides a lithographic printing plate with high printing durability. Another object of the present invention is to provide a photosensitive composition that has good adhesion to a substrate and provides a flexible film.

[Means for solving problems]

As a result of various studies, the present inventors have come up with the following photosensitive composition useful for achieving the above object.

That is, the present invention provides a positive photosensitive composition characterized by containing a water-insoluble and alkaline water-soluble polymer having an active imino group.

In a preferred embodiment of the present invention, the polymer has a structural unit represented by the following general formula [I] or [II].

(X), [However, in the formula, A is a hydrogen atom, a halogen atom, or a carbon number 1
~4 alkyl group. B represents an alkylene group, a phenylene group, a substituted alkylene group, or a substituted alkylene group; and R1 represents an alkyl group, a phenyl group, a substituted alkyl group, or a substituted phenyl group. ). m and n represent 0 or 1, and m and n are never both 0. Further, the imino group is directly bonded to at least one carbonyl group or sulfonyl group of X or Y. ] (However, in the formula, E is a hydrogen atom, a halogen atom, or a carbon number of 1 to
4 represents an alkyl group or a phenyl group.

F and G each independently represent an alkylene group or a substitution 1, and at least one of q or q' is 1. In addition, the polymer in the present invention has a small number of imino groups (both are directly bonded to one carbonyl group or sulfonyl group).
It is characterized by having an active imino group in its molecular structure, and its dissociation causes it to dissolve in a developing solution, which is alkaline water.

The active imino group in the present invention has a degree of dissociation (pKa) of 4.
-11, more preferably 5-9. If the pKa is either larger or smaller than this range, the range of appropriate development conditions will be narrowed.

It was truly surprising that the polymer of the present invention provides a photosensitive composition that has good adhesion to a substrate, excellent abrasion resistance, and a wide range of appropriate development conditions (broad development tolerance). .

A preferred structure of the polymer in the present invention is the general formula C
I) or (II).

A in the general formula CI) is a hydrogen atom, a /'%rogen atom, or an alkyl group, and more preferably a hydrogen atom or a methyl group.

B is an alkylene group, a phenylene group, a substituted alkylene group or a substituted phenylene group, and more preferably a phenylene group or a case where m=0.

-C=N, -No2 or -R1, more preferably a phenyl group, a naphthyl group, a cyclohexyl group or an alkyl group having 1 to 4 carbon atoms.

General formula [E in ID is a hydrogen atom, a halogen atom,
It represents an alkyl group having 1 to 4 carbon atoms or a phenyl group, and more preferably a hydrogen atom.

F and G each independently represent an alkylene group or a substituted alkylene group, but more preferably a methylene group or a p
This is the case when =p'=o.

The molecular weight of the polymer in the present invention can range from a wide range, but when measured by gel permeation chromatography using polystyrene as a standard, the weight average molecular weight ('llffw) ranges from 500 to 1. ．． 00
Preferably, it is 0,000, more preferably,
It is 4.000 to 300.000. The proportion of the polymer having active imino groups in the photosensitive composition of the present invention is 3 to 90% by weight, more preferably 15 to 50% by weight.

The polymer having an active imino group in the present invention may be a polymer having a repeating structure consisting only of the structural units of the general formula CI) or [II), or a copolymer of the general formulas [I) and (n), but the commonly used It may also be a multi-component copolymer having a repeating structure in which one or more of the vinyl monomers listed above are combined.

In the case of such a multicomponent copolymer, general formula (I) or CI
Structural units shown in [ ] alone or in combination, 10
It is preferably contained in an amount of mol % or more, and more preferably 20 mol % or more. Structural units used in combination with the structural unit represented by general formula (I) or [■] include, for example, ethylenically unsaturated olefins such as ethylene, propylene, imbutylene, butadiene, and isobutylene, such as styrene, α-methyl Styrenes such as styrene, 0-methylstyrene, m-methylstyrene, p-methylstyrene, 0-chlorostyrene, p-chlorostyrene, e.g. acrylic acid, methyl acrylate, acrylic acid etynopea, acrylic acid 1so-putino Acrylic acid and its esters such as hexyl acrylate, octyl acrylate, 2-hydroxyethyl acrylate, 2-cyanoethyl acrylate, glycidinopacrylate dimethylaminoethyl acrylate, e.g. methacrylic acid , methyl methacrylate, ethyl methacrylate, n-butinope methacrylate methacrylic acid 1
so-butyl, tert-butynope methacrylate, hexynope methacrylate, 2-ethylhexynope methacrylate, urinope methacrylate, tridecyl methacrylate, cyclohexyl methacrylate, pendinope methacrylate, 2-hydroxyethyl methacrylate, methacrylic acid 2-hydroxypropinope dimethylaminoethyl methacrylate,
Methacrylic acid and its esters such as diethylaminoethyl methacrylate, glycidinope methacrylate, tetrahydrofurfuryl methacrylate, allyl methacrylate, vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl caproate, vinyl benzoate, etc. , for example, nitriles such as acrylonitrile and allyl methacrylate, such as methyl vinyl ether, ethyl vinyl ether, inbutyl vinyl ether, β-
Chloroethyl vinyl ether/to vinyl ethers such as cyclohexyl vinyl ether, such as acrylamide, N-methylacrylamide, NlN-dimethylacrylamide, N-tert-butylacrylamide,
Acrylamides such as N-octylacrylamide and diacetone acrylamide, such as N-vinylpyronopene N-vinylcarbazole, N-vinylindole, N
-Those with a structure in which the unsaturated double bonds of vinyl monomers such as N-vinyl compounds such as vinylpyrrolidone are cleaved, and other phenolic hydroxyl groups disclosed in JP-A No. 58-203433. Examples include substituted styrenes having

Next, typical examples of polymers having active imino groups in the present invention will be shown.

[Exemplary compounds]

Nα5Nα6 Nα5Nα6 Nα7 Next, typical synthesis examples of the polymer having an active imino group in the present invention will be shown, but the present invention is not limited to these examples in any way.

Synthesis Example 1 10.0 g (0,044 mol) and 4.46 g (0,044 mol) of methyl methacrylate were dissolved in V-65[2,2'-azobis-(2 ,4-dimethylvaleronitrile]0.0213
Copolymerization was carried out using g as an initiator.

After stirring at 60°C for 7 hours, 60ml of 2-methoxyethanol was added! was added and reprecipitated into water 21.

The obtained polymer was dissolved in 100 ml of tetrahydrofuran, and then reprecipitated in 1.5 A of methanol to obtain 10.2 g of polymer of Exemplified Compound No. 1.

(1Jw = 200000, yield 70%) The composition ratio of the polymer was determined by 'H-NMR.

(Similarly below) Synthesis Example 2 N-methacrylylsulfonamide 15.78 g (0,
070 mol), benzyl methacrylate 12.35 g (0
,070 mol) in 47 ml of ethyl acetate -650,
Copolymerization was carried out using 173 g as an initiator. After stirring at 60°C for 6 hours, the resulting polymer was reprecipitated in 1.5β of hexane, dissolved in 150ml of tetrahydrofuran, and reprecipitated in methanol 21 to obtain poly7-23. of exemplified compound Nα2. 4g was obtained. (Nw =
65000, yield 83%) Synthesis Example 3 N-methacrylylsulfonamide 11.28 g (0,
055 mol), ethyl acrylate 1-3.74 g (0
, 15 mol) for ethyl acetate 65 I! Inside, ■-65
Copolymerization was carried out using 0.235 g as an initiator. 60
After stirring at °C for 6 hours, 50 ml of ethyl acetate was added.
Hexane 2! It sank back inside. The obtained polymer was dissolved in 150 mf of ethyl acetate and reprecipitated in 1.52 mf of hexane to obtain 23.9 g of a polymer of Exemplified Compound 3. (1~=60000, yield 96%) Synthesis example 4 N-methacrylylsulfonamide 11.27 g (0,
050 mol), n-butyl acrylate 13.74 g (
0,107 mol) of V-650 in 65 ml of ethyl acetate.
, 195 g was used as an initiator. After stirring at 60°C for 6 hours, it was reprecipitated in 1.5β hexane to obtain 20.6 g of polymer of Exemplified Compound 4 (iw = 830
00, yield 82%) Synthesis Example 5 14.58 g (0.15 mol) of maleimide and 15.04 g (0.15 mol) of methyl methacrylate were mixed in V-650.3 in 1-acetoxy-2-methoxyethane 69rr+f.
Copolymerization was carried out using 71 g as an initiator. After stirring at 60° C. for 2 hours, 50 ml of 1-acetoxy-2-methoxyethane was added and the mixture was reprecipitated in 2β of water to obtain 23.7 g of a polymer of Exemplary Compound 5. (-M' = 59000, yield 80%) Synthesis Example 6 9.75 g (0.10 mol) of maleimide and 17.62 g (0.10 mol) of benzyl methacrylate were added to 64 ml of 1-acetoxy-2-methoxyethane. Inside■-65 0.
Copolymerization was carried out using 125 g as an initiator. 4 at 60℃
After stirring for an hour, 30 mA' of 1-acetoxy-2-methoxyethane was added, and the mixture was reprecipitated into water 21. The obtained polymer was mixed with 150 m of 1-acetoxy-2-methoxyethane.
I! 22.5 g of a polymer of Exemplified Compound 6 was obtained by dissolving it in water and reprecipitating it in water 21. (mw = 84
GOO1 yield: 82%) Synthesis Example 7 N-methacrylylsulfonamide 11.28 g (0,
055 mol), ethyl acrylate 3.30 g (0,0
33 mol), n-butyl acrylate 5.77 g (0,
-650 mol) in 75 ml of ethyl acetate.
Copolymerization was carried out using 171 g as an initiator. 6 at 60℃
After stirring for an hour, the mixture was reprecipitated into 1.5β hexane to obtain 18.7 g of a polymer of Exemplified Compound 7. (mw = 7
6000, yield 92%) As the photosensitizing compound that acts on the positive type used in the present invention, 0-naphthoquinonediazide compounds are preferred, and 1 and 2 described in Japanese Patent Publication No. 43-28403 Most preferred are esters of -diazonaphthoquinone sulfonic acid chloride and pyrogallol-acetone resin. Other suitable orthoquinonediazide compounds include U.S. Patent No. 3.046.
120 and 3.188.210 are esters of 1,2-diazonaphthoquinonesulfonic acid chloride and phenol-formaldehyde resins. Other useful 0-naphthoquinone diazide compounds are known and reported in numerous patents. For example, JP-A-47-5303, JP-A-48-6
No. 3802, No. 63803, No. 48-63, No. 48-96
No. 575, No. 49-38701, No. 133-1973
No. 54, Special Publication No. 11222/1973, 961/1973
No. 0, Publication No. 49-17481, U.S. Patent Nos. 2 and 7
No. 97.213, No. 3.454.400, No. 3.
No. 544.323, No. 3.573.917, No. 3
．． 674.495, British Patent No. 3, 785.825, British Patent No. 1.227.602, British Patent No. 1, 251.345
No. 1.267, 005, No. 1.329.88
No. 8, No. 1.330.932, German Patent No. 854
．． Examples include those described in various specifications such as No. 890.

In addition, as a photosensitive compound or photosensitive mixture that acts in a positive manner without using an 0-naphthoquinone diazide compound, for example, a polymer compound having an orthonitrocarbinol ester group, which is described in the specification of Japanese Patent Publication No. 56-2696, is also used. It can be used in the present invention.

Furthermore, a photosensitive mixture of a compound that generates an acid upon photolysis and a compound having a C-0-C group or a C-0-3i group that dissociates with an acid can also be used in the present invention.

For example, the combination of a compound that generates an acid upon photolysis and an acetal or 0,N-acetal compound is
-89003), combination with orthoester or amide acetal compound JP-A-51-120714),
combination with a polymer having an acetal or ketal group in the main chain (JP-A-53-133429); combination with an enol ether compound (JP-A-55-12995);
Combination with N-acyliminocarbonate compound (JP-A-55-
126236), a combination with a polymer having an orthoester group in the main chain (JP-A-56-17345), a combination with a silyl ester compound (JP-A-60-10247)
No.) and combination with silyl ether compound JP-A-60
-37549, JP-A-60-121446), etc.

The amount of these positively acting photosensitive compounds or photosensitive mixtures in the photosensitive composition of the present invention is 10 to 50% by weight, more preferably 20 to 40% by weight.

In addition to the polymer of the present invention, the composition of the present invention contains known alkali-soluble polymer compounds such as phenol formaldehyde resin, cresol formaldehyde resin, phenol-modified xylene resin, polyhydroxystyrene, and polyhalogenated hydroxystyrene. can be done.

Such alkali-soluble polymer compound accounts for 70% of the total composition.
It is used in an amount of less than % by weight.

The composition of the present invention may contain a cyclic acid anhydride to increase sensitivity, a printout agent to obtain a visible image immediately after exposure, a dye as an image coloring agent, and other fillers. As a cyclic acid anhydride, US Pat. No. 4.115.
128, phthalic anhydride,
Tetrahydrophthalic anhydride, hexahydrophthalic anhydride, 3,6-nindooxy-Δ4-tetrahydrophthalic anhydride, tetrachlorophthalic anhydride, maleic anhydride, chloromaleic anhydride, α-phenylmaleic anhydride, succinic anhydride, pyromellitic acid By containing these cyclic acid anhydrides in an amount of 1 to 15% by weight based on the total composition, the sensitivity can be increased up to about 3 times. Typical print-out agents for obtaining a visible image immediately after exposure include a combination of a photosensitive compound that releases an acid upon exposure and an organic dye that can form a salt. Specifically, JP-A-50-36209, JP-A-53-81
The combination of 0-naphthoquinonediazide-4-sulfonic acid halide and a salt-forming organic dye described in JP-A No. 28, JP-A-53-36223, JP-A-Sho 54-74
The combination of a trihalomethyl compound and a salt-forming organic dye described in Japanese Patent No. 728 can be mentioned. In addition to the above-mentioned salt-forming organic dyes, other dyes can also be used as image coloring agents. Suitable dyes include oil-soluble dyes and basic dyes, including salt-forming organic dyes. Specifically, oil yellow #101, oil yellow #130, oil pink #312, oil green BG, oil blue BO3, oil blue #603.
, Oil Black BY, Oil Black BS, Oil Black T-505 (manufactured by Orient Chemical Industry Co., Ltd.), Crystal Violet (CI42555), Methyl Violet (CI42535), Rhodamine B (
CI45170B), malachite green (CI420
00), methylene blue (CI52015), etc.

The composition of the present invention is applied onto a support after being dissolved in a solvent that dissolves each of the above components. The solvent used here is
These include ethylene dichloride, cyclohexanone, methyl ethyl ketone, ethylene glycol monomethyl ether, propylene glycol monomethyl ether, ethylene glycol monoethyl ether, 2-methoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, toluene, and ethyl acetate. Solvents may be used alone or in combination.

The concentration (solid content) of the above components is 2 to 50% by weight. The amount of coating varies depending on the application, but for example, for photosensitive planographic printing plates, it is generally preferable to have a solid content of 0.5 to 3.0 g/m''.As the amount of coating decreases, the photosensitivity increases. However, the physical properties of the photoresist film deteriorate.

When producing a lithographic printing plate using the photosensitive composition of the present invention, the support may be a hydrophilized aluminum plate, such as a silicate-treated aluminum plate, an anodized aluminum plate, a grained aluminum plate, There is an aluminum plate with electrodeposited silicate, and other examples include zinc plate, stainless steel plate, chromium-treated steel plate, and hydrophilized plastic film and paper.

Developers for the photosensitive 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, Aqueous solutions of inorganic alkaline agents such as ammonium diphosphate, sodium metasilicate, sodium bicarbonate, aqueous ammonia, etc. are suitable, and their concentrations are 0.1 to 10% by weight,
It is preferably added in an amount of 0.5 to 5% by weight.

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

〔Example〕

Next, the present invention will be explained in more detail by giving examples. All percentages in the examples below are by weight unless otherwise specified.

Examples 1 to 7 The surface of an aluminum plate having a thickness of 0.30 um was grained using a nylon brush and a water suspension of 400 mesh pumice stone, and then thoroughly washed with water.

After etching by immersing in 10% sodium hydroxide at 70°C for 60 seconds, washing with running water and 20% HNO.

Neutralized and washed with water. This was subjected to electrolytic surface roughening treatment in a 1% nitric acid aqueous solution under the condition of VA=12.7V using a sinusoidal alternating waveform current at an anode special electric charge of 160 clones/dms. When the surface roughness was measured, it was found to be 0.6
μ (expressed as Ra), followed by 30% H2S
After being immersed in an aqueous solution of O and desmutted at 55°C for 2 minutes, it was anodized to a thickness of 2.7 g/m' at a current density of 2 A/dm in 20% H2SO<aqueous solution.

The following photosensitive solution was applied onto the thus obtained aluminum support using a whiler and dried at 100° C. for 2 minutes.

Naphthoquinone-(1,2)-0,7,5g diazide-(
2) Esterification reaction product of -5-sulfonyl chloride and cresol novolak resin m-cresol novolak resin 1.40 g Tetrahydrophthalic anhydride 0.15 g 1st
Polymer listed in the table 0.70 g2-(
p-butoxyphenyl) -0,02g4.6-bis(
Trichloromethyl)-3-triazinenaphthoquinone-1,2-diazide-0,03g 4-sulfonic acid chloride Crystal violet 0.01 g Oil Blue #603 0.015g (manufactured by Orient Chemical Industry Co., Ltd.) Ethylene dichloride 18g 2-methoxyethyl acetate The amount of application after drying is 2.
1 g/m''. Each of these photosensitive lithographic printing plates was exposed to light for 40 seconds using a 2 KIll metal halide lamp from a distance of 1 m through a positive transparent original.The exposed photosensitive lithographic printing plates were soaked in a 4% aqueous sodium metasilicate solution. 1
The plate was immersed for a minute, developed, and then processed according to a conventional method to obtain a lithographic printing plate. The lithographic printing plate thus obtained was printed on an offset printing machine to perform a rigidity test.

If the printing durability is poor, the image area will wear out and ink will not adhere to it after a small number of sheets are printed, making it impossible to obtain normal printed matter.

In addition, in order to investigate the wide range of suitable development conditions (development acceptability), changes in tone reproducibility were investigated when developing by immersing in the developer for 5 minutes and developing by immersing for 1 minute. ○ indicates that there was almost no change, × indicates that there was a large change, and ∆ indicates that there is a significant change. In addition, in order to examine the adhesion and flexibility of the photosensitive composition to the substrate, the image area was scratched after exposure by applying a constant load with a diamond needle, and after development, the composition was printed and the ease of scratching was examined. ○ for items that are hard to get scratched, 1 for items that are extremely easy to get scratched, △ for those in between.
It was displayed in These results are shown in Table 1.

As is clear from Table 1, the photosensitive composition of the present invention is
It can be seen that it has extremely excellent performance.

Examples 8 to 11 The following photosensitive liquids were applied onto supports prepared in the same manner as in Examples 1 to 7 using a whiler, and dried at 100°C for 2 minutes.

0 naphthoquinone-(1,2)-0,90g diazirho-(
2) Esterified product of -5-sulfonyl chloride and pyrogallol-acetone resin (described in Example 1 of US Patent No. 3.635.709) 0 Exemplary compound Nα1 Listed in Table 2 0
Cresol novolak resin 2.1g to (m)
-Cresol, ratio of exemplified cresol in table p-2 5:5) Amount minus the amount of compound Nα1 added 02-Trichloromethyl-5-0,04g (4-hydroxystyryl)-1,3,4- Oxadiazole 0 Phthalic anhydride 0.20 g
O oil-soluble dye (CI42595) 0.03g
o Ethylene dichloride 15go Methyl cellosolve 8gThe coating amount after drying was 2.5g/rn''.These photosensitive lithographic printing plates were evaluated in the same manner as Examples 1 to 7, and the results are shown in Table 2. It can be seen from Table 2 that the photosensitive composition of the present invention has excellent performance.

〔Effect of the invention〕

The photosensitive composition containing the polymer having an active imino group of the present invention has good developability and printing durability, and also has excellent adhesion to a substrate.

Showa year month day 3. Relationship to the case of the person making the amendment Applicant name (520) Fuji Photo Film Co., Ltd. 4;
Agent 5, date of amendment order Voluntary (1) Amend the scope of claims as shown in the attached sheet.

(2) Correct the following errors in the description.

Claims (1) A positive photosensitive composition comprising a polymer having an active imino group and being insoluble in water and soluble in alkaline water.

(2) The photosensitive composition according to claim (1), wherein the degree of dissociation (pKa) of the active imino group is 4 to 11.

(3) Claim No. 1 in which the active imino group is directly bonded to at least one carbonyl group or sulfonyl group.
) or (2).

(4) The photosensitive composition according to claim (3), wherein the polymer has a structural unit represented by the following general formula [■] or CII).

! fcH, -C+- ζ (B).

(X),.

Chang Y [1 [However, in the formula, A is a hydrogen atom, a halogen atom, or a carbon number of 1
~4 alkyl group. B represents an alkylene group, a phenylene group, a substituted alkylene group, or a substituted phenylene group. X represents 10-1 (I or -R1 (however, R1 represents an alkyl group, a phenyl group, a substituted alkyl group, or a substituted phenyl group).m
and n represent 0 or 1, and m and n are never both 0. Further, the imino group is directly bonded to at least one carbonyl group or sulfonyl group of X or Y. 〕(
F) P(G), (where E is a hydrogen atom, a halogen atom, or a carbon number of 1 to
4 represents an alkyl group or a phenyl group. F and G each independently represent an alkylene group, q' represents 0 or 1, and q
or at least one of q' is 1. Further, the imino group is directly bonded to at least one carbonyl group or sulfonyl group. )

Claims (4)

[Claims] (1) A positive photosensitive composition having an active imino group and containing a water-insoluble and alkaline water-soluble polymer. (2) The photosensitive composition according to claim (1), wherein the degree of dissociation (pKa) of the active imino group is 4 to 11. (3) Claim No. 1 in which the active imino group is directly bonded to at least one carbonyl group or sulfonyl group.
) or (2). (4) The photosensitive composition according to claim (3), wherein the polymer has a structural unit represented by the following general formula [I] or [II]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [I] [However, in the formula, A is a hydrogen atom, a halogen atom, or a carbon number of 1
~4 alkyl group. B represents an alkylene group, a phenylene group, a substituted alkylene group or a substituted phenylene group. X represents ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼. Y has ▲mathematical formulas, chemical formulas, tables, etc.▼, ▲mathematical formulas, chemical formulas, tables, etc.▼, ▲mathematical formulas, chemical formulas,
There are tables, etc. ▼, -C≡N, -NO_2 or -R^1 (However, R^1 represents an alkyl group, phenyl group, substituted alkyl group, or substituted phenyl group.)
. m and n represent 0 or 1, and m and n are never both 0. Further, the imino group is directly bonded to at least one carbonyl group or sulfonyl group of X or Y. ] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [II] (However, in the formula, E is a hydrogen atom, a halogen atom, or a carbon number of 1 to
4 represents an alkyl group or a phenyl group. F and G each independently represent an alkylene group or a substituted alkylene group. X represents ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼. P, P', q and q' represent 0 or 1, and at least one of q or q' is 1. Further, the imino group is directly bonded to at least one carbonyl group or sulfonyl group. )