JPH0481788B2 - - Google Patents

Description

[Detailed description of the invention]

FIELD OF THE INVENTION The present invention relates to photosensitive compositions containing novel photo-generated free radical compounds. More specifically, 2-halomethyl-1,3,4
- It relates to a photosensitive composition containing an oxadiazole compound. Compounds that decompose to produce free radicals upon exposure to light (free radical generators) are well known in the graphic arts field. They are widely used as photoinitiators in photopolymerizable compositions, photoactivators in free radical photographic compositions, and photoinitiators for reactions catalyzed by photogenerated acids. Such free radical generators are used to make a variety of photosensitive materials useful in printing, duplication, copying and other imaging systems. Organic halogen compounds photolyze to give halogen radicals such as chlorine radicals and bromine radicals. These halogen radicals are good hydrogen abstractors and produce acids in the presence of hydrogen donors.
For their application to photopolymerization processes and free radical photography processes, see J. Kosar, “Light Sensitive Systems.”
(Systems)” J.Wiley & Sons
(Sands) (New York).
1965), pages 180-181 and 361-370. [Prior Art] Conventionally, carbon tetrabromide, iodoform, tribromoacetophenone, and the like are representative compounds that generate halogen free radicals by the action of light, and have been widely used. However, since these free radical generating agents sublimate or have a bad odor, if they are used in a photosensitive material with a photosensitive layer provided on a support, the photosensitive layer may be damaged during manufacture, use, or storage of the photosensitive material. It volatilized from the water, reducing its effectiveness and becoming a sanitary problem. Furthermore, these free radical generating agents have problems in compatibility with other elements contained in the photosensitive layer. Furthermore, they have low photodecomposition sensitivity to light sources (metal halide lamps, etc.) commonly used in the production of printing plates, so it has been necessary to add them in large quantities in order to exhibit sufficient effects. When added in large amounts to the photosensitive layer, it has generally had a large adverse effect on the mechanical properties, developability, etc. of the photosensitive layer. In order to solve this problem, 2-halomethyl-5-vinyl-1,3,4-oxadiazole is disclosed in JP-A-54-74728 and JP-A-55-77742 as compounds that generate halogen free radicals, respectively. Compound, 4-trihalomethyl-5-aryl-1,
Photosensitive compositions using 3,4-oxadiazole compounds have been proposed. Furthermore, JP-A-59-148784
In the above publication, a 2-halomethyl-1,3,4-oxadiazole compound characterized by having a benzofuryl group at the 5-position either directly or via a vinyl group was proposed as a compound that generates a halogen free radical. . In particular, the oxadiazole compound disclosed in JP-A-59-148784 has excellent properties such as extremely high sensitivity to photolysis and excellent stability over time against commonly used light sources rich in ultraviolet light. However, when used as a component of the photosensitive composition of a lithographic printing plate, some of the photosensitive composition tends to remain in the non-image area after development, so it is especially difficult to soak cotton wool, sponge, etc. in the developer and rub it off. When developing the plate, the photosensitive composition remained partially in the non-image area, resulting in unevenness that not only spoiled the appearance, but also often caused scumming when used as a lithographic printing plate. [Object of the Invention] Therefore, an object of the present invention is to provide a photosensitive composition that hardly leaves a photosensitive composition in non-image areas after development and that does not easily cause scumming when used in a lithographic printing plate. . Another object of the present invention is to provide a photosensitive composition with excellent stability over time (that is, a property that maintains performance equivalent to that immediately after production even after long-term storage). Still another object of the present invention is to provide a photosensitive resist-forming composition that exhibits high sensitivity to commonly used ultraviolet light sources. Still another object of the present invention is to provide a photosensitive layer with excellent physical properties and developability. Further objects of the invention will become apparent from the following description. [Summary of the Invention] In order to achieve the above object, the present inventors have conducted various studies, and as a result, have arrived at the present invention, which consists of a 1,3,4-oxadiazole nucleus. 2 in which a benzofuryl group having 1 to 2 hydroxyl groups is bonded directly or via a vinyl group to the 5-position of
-A photosensitive composition containing a halomethyl-1,3,4-oxadiazole free radical generator. What does "soluble" mean as used herein?
Indicates that it dissolves at a concentration of 0.002wt% or more, and alkaline water refers to an aqueous sodium hydroxide solution or an aqueous sodium silicate solution that does not contain an organic solvent. In Japanese Patent Application Laid-open No. 59-148784 as mentioned above,
2-halomethyl- characterized by having a benzofuryl group at the 5-position directly or via a vinyl group
Although a 1,3,4-oxadiazole-based free radical generating agent is disclosed, this compound is insoluble even in alkaline water with a pH of 9 or higher, and in this point it is essentially different from the present invention. That is, since the free radical generating agent used in the present invention has 1 to 2 hydroxyl groups in the benzofuryl group, it is soluble in alkaline water, which is probably why the photosensitive composition does not remain in the non-image area after development. For example, when used in planographic printing plates, scumming seems to be extremely difficult to occur, and the effect is remarkable. The preferred free radical generating agent of the present invention can be represented by the following general formula []. General formula [] Here, X represents a chlorine atom or a bromine atom, Y represents a hydrogen atom, a halogen atom, an alkyl group, or an aryl group, A represents a benzofuryl group substituted with 1 to 2 hydroxyl groups, and m is an integer of 1 to 3. , n is 0
or 1. The benzofuryl group substituted with 1 or 2 hydroxyl groups represented by A may be a 2-benzofuryl group or a 3-benzofuryl group, and the benzofuryl group may include an alkyl group, an alkoxy group, a cyano group in addition to a hydroxyl group. may be substituted with groups or atoms such as nitro groups, phenoxy groups, phenyl groups and halogen atoms. Here, each of the alkyl group and the alkoxy group preferably has 1 to 6 carbon atoms. Examples of particularly preferred compounds in the present invention are shown below. For example, the compound represented by the general formula []
It is synthesized by dealkylating (or dealkylenating) the ether bond moiety of a compound represented by the following general formula [] or [], which is synthesized according to the synthesis method described in Publication No. 59-148784. Ru. General formula [] General formula [] (Here, X, Y, m, and n have the same meanings as in the general formula []. R represents a lower alkyl group or a benzyl group, and l is 1 or 2.) alkylenation) reaction, for example, Organic Synthesis,
The method described in Collect Volume, pp. 412-414 (1973), by M. Gerecke et al., Helvetica Chimica
Acta, Vol. 59, pp. 2551-2557 (1976), EHVickery et al., Journal of Organic
Chemistry, Vol. 44, pp. 4444-4446 (1979), or M. Node et al., Journal of
It can be carried out according to the method described in Organic Chemistry, Vol. 45, pp. 4275-4277 (1980). In the photosensitive composition containing the free radical generator of the present invention, at least one addition-polymerizable ethylenically unsaturated monomer or oligomer, e.g., a film-cleavable group such as a C-O-C bond, is present.
It includes compounds that interact with photodecomposition products of free radical generating agents, such as compounds that develop, decolor, or change color with acids (hereinafter referred to as color change agents). The free radical generating agent in the present invention includes a lithographic printing plate,
A photosensitive resist-forming composition used for manufacturing IC circuits, photomasks, etc. has the ability to immediately provide visible contrast with unexposed areas without developing upon exposure (hereinafter referred to as printout ability). This is particularly useful when giving. A photosensitive resist composition having such printout ability can obtain a visible image by exposure alone, below the yellow safety light in the exposure process. When printing is interrupted, it becomes possible for the plate maker to know whether the plate given to him is being exposed or not.
At the same time, for example, when a large plate is exposed to light many times, as in the so-called reprint printing method used to make lithographic printing plates, it is difficult for the operator to immediately check which areas have been exposed. can. The composition used to provide such printout ability (hereinafter referred to as printout composition) contains a free radical generating agent and a discoloration that changes color due to the free radicals generated from the free radical generating agent. The free radical generating agent of the present invention is effectively used as the free radical generating agent. In the present invention, as a color change agent, one that changes from an originally colorless state to a colored state due to the action of the photodegradation product of the free radical generating agent of the present invention, and one that changes color from an originally colorless state to a colored state, and a color change agent that changes color from an originally colorless state to a colored state due to the action of the photodecomposition product of the free radical generating agent of the present invention. There are two types: one that bleaches color and one that bleaches color. Typical examples of color changing agents belonging to the former type include arylamines. Arylamines suitable for this purpose include simple arylamines such as primary and secondary aromatic amines, as well as so-called leuco dyes, examples of which are as follows. Diphenylamine, dibenzylaniline, triphenylamine, diethylaniline, diphenyl-p-phenylenediamine, p-toluidine,
4,4'-biphenyldiamine, o-chloroaniline, o-bromoaniline, 4-chloro-o-phenylenediamine, o-bromo-N,N-dimethylaniline, 1,2,3-triphenylguanidine, Naphthylamine, diaminodiphenylmethane, aniline, 2,5-dichloroaniline, N-
methyldiphenylamine, o-toluidine, p,
p′-tetramethyldiaminodiphenylmethane,
N,N-dimethyl-p-phenylenediamine,
1,2-dianilinoethylene, p,p′,p″-hexamethyltriaminotriphenylmethane, p,
p′-tetramethyldiaminotriphenylmethane,
p,p'-tetramethyldiaminodiphenylmethylimine, p,p',p''-triamino-o-methyltriphenylmethane, p,p',p''-triaminotriphenylcarbinol, p,p'- tetramethylaminodiphenyl-4-anilinonaphthylmethane,
p, p′, p″-triaminotriphenylmethane,
p,p',p''-hexapropyltriaminotriphenylmethane. Also, as a color-changing agent that originally has a unique color, this color changes or is decolored by the photodecomposition product of the free radical generating agent. , diphenylmethane, triphenylmethane, thiazine, oxazine, xanthene, ansteraquinone, iminonaphthoquinone, and azomethine. Examples of these are as follows. Brilliant green, eosin, ethyl violet, erythrosin B, methyl green, crystal violet, basic fuchsin, phenolphthalein, 1,3-diphenyl triazine, alizarin red S, thymol phthalein,
Methyl Violet 2B, Quinaldine Red, Rose Bengal, Methanil Yellow, Thymol Sulfophthalein, Xylenol Blue, Methyl Orange, Orange, Diphenylthiocarbazone,
2,7-dichlorofluorescein, paramethyl red, congo red, benzopurpurin 4B,
α-Naphthyl Red, Nile Blue 2B, Nile Blue A, Phenacetarin, Methyl Violet, Malachite Green, Parafuchsin, Oil Blue #603 [manufactured by Orient Chemical Industry Co., Ltd.], Oil Pink #312 [manufactured by Orient Chemical Industry Co., Ltd.] , Oil Red 5B [manufactured by Orient Chemical Industry Co., Ltd.], Oil Scarlet #308 [manufactured by Orient Chemical Industry Co., Ltd.], Oil Red OG [manufactured by Orient Chemical Industry Co., Ltd.], Oil Red RR [manufactured by Orient Chemical Industry Co., Ltd.] ], Oil Green #502 [manufactured by Orient Chemical Industry Co., Ltd.], Spiron Red BEH Special [Hodogaya Chemical Industry Co., Ltd.]
], m-Cresol Purple, Cresol Red, Rhodamine B, Rhodamine 6G, Fast Ash Biolette R, Sulforhodamine B,
Auramine, 4-p-diethylaminophenyl imino naphthoquinone, 2-carboxyanilino-4
-p-diethylaminophenylimino naphthoquinone, 2-carbostearylamino-4-p-dihydroxyethyl-amino-phenylimino naphthoquinone, p-methoxybenzoyl-p'-diethylamino-o'-methylphenyliminoacetanilide, cyano -p-diethylaminophenyl iminoacetanilide, 1-phenyl-3-methyl-
4-p-diethylaminophenylimino-5-pyrazolone, 1-β-naphthyl-4-p-diethylaminophenylimino-5-pyrazolone. In the printout compositions according to the invention, the free radical generators of the invention are stable over time, but among those used as color changing agents, leucotriphenylmethane dyes are generally susceptible to oxidation. Therefore, when using these dyes, it is effective to include some kind of stabilizer. Stabilizers for this purpose include the amines described in U.S. Pat. No. 3,042,573;
Zinc oxide, phenols, sulfur compounds described in 3042516, alkali metal iodides, organic acids, organic anhydrides described in 3082086, 3377167 The triaryl compounds of antimony, arsenic, bismuth, and phosphorus described in 1 are effective. The ratio of the above color change agent and the free radical generator of the present invention is from about 0.01 part by weight to about 100 parts by weight, more preferably from 0.1 to 10 parts by weight of the free radical generator of the present invention to 1 part by weight of the color change agent. Parts by weight are used, most preferably in the range of 0.5 to 5 parts by weight. Also,
They may be used in combination with the free radical generating agent in the present invention. On the other hand, the photosensitive resist-forming composition, which is the object to which printout ability is imparted by the printout composition of the present invention, can be used to create various printing plates such as lithographic printing plates, IC circuits, photomasks, etc., as described above. used for. Various things are included. Typical examples include (1) compositions made of diazo resins, (2) compositions made of o-quinonediazide compounds, (3) compositions made of photosensitive azide compounds, and (4) main chains of polymers. or -CH=CH-CO in the side chain
(5) a photopolymerizable composition comprising an addition-polymerizable unsaturated compound and a photopolymerization initiator; details of these compositions are described in U.S. Pat. No. 4,279,982. It is stated in column 8, line 11 to column 11, line 32. When such a photosensitive resist-forming composition contains the printout composition, based on 100 parts by weight of the photosensitive resist-forming composition,
From about 0.1 parts by weight to about 0.1 parts by weight of the printout composition
It can be contained in an amount of 150 parts by weight, more preferably 1 to 60 parts by weight. Examples of solvents used when applying the photosensitive register-forming composition imparted with printout ability include ethylene dichloride, cyclohexanone, methyl ethyl ketone, 2-methoxyethyl acetate, monochlorobenzene, toluene, and ethyl acetate. These can be used alone or in combination. The photosensitive resist-forming composition imparted with such printout ability is particularly suitable for photosensitive lithographic printing plates (Presensitized plates) used for preparing lithographic printing plates.
(Plate) and abbreviated as PS version. ) is advantageously used as a photosensitive layer. In this case, the support is, for example, a metal plate made of aluminum (including aluminum alloys), zinc, iron, steel, etc., or plastics on which such metals are laminated or vapor-deposited, and most preferably an aluminum plate. It is. In the case of supports with metal surfaces, especially aluminum, graining, sodium silicate, potassium fluorozirconate,
It is preferable that the surface be subjected to a surface treatment such as immersion treatment in an aqueous solution such as a phosphate or an anodic oxidation treatment. Also, as described in British Patent No. 851,819, an aluminum plate that has been grained and then immersed in an aqueous sodium silicate solution or anodized in sulfuric acid, as described in US Pat. No. 3,181,461. An aluminum plate which is anodized and then immersed in an aqueous solution of an alkali metal silicate is also preferably used. The above-mentioned anodizing treatment is carried out using, for example, an aqueous or non-aqueous solution of an inorganic acid such as phosphoric acid, chromic acid, sulfuric acid, or boric acid, or an organic acid such as oxalic acid or sulfamic acid, or a salt thereof, either alone or in combination. Among these, it is particularly preferably carried out by passing an electric current through an aluminum plate as an anode in an aqueous solution of phosphoric acid, sulfuric acid, or a mixture thereof. Also effective is silicate electrodeposition as described in US Pat. No. 3,658,662. Additionally, British Patent No.
Also preferred is an aluminum plate which is electrolyzed with alternating current in a hydrochloric acid electrolyte and then anodized in a sulfuric acid electrolyte, as described in No. 1208224. Further, it is preferable to provide an undercoat layer of a cellulose resin containing a water-soluble salt of a metal such as zinc on the aluminum plate anodized in the above process in order to prevent scum during printing. The amount of photosensitive layer provided on such a support is from about 0.1 to about 7 g/m ² , preferably from 0.5 to 4 g/m 2 .
^m2 range. The thus obtained PS plate is subjected to image exposure, and then an image is formed by processing including development using a conventional method. For example, in the case of a PS plate having a photosensitive layer of a photosensitive composition in which the composition (1) made of diazo resin contains a printout composition,
After image exposure, the unexposed portions of the photosensitive layer are removed by development to obtain a lithographic printing plate. In addition, in the case of a PS plate having a photosensitive layer made of a photosensitive composition containing a printout composition in the composition (2) above, after image exposure, the exposed portion is removed by developing with an alkaline aqueous solution. A lithographic printing plate is obtained. No matter what kind of photosensitive layer the PS version has,
The ability to print out according to the present invention does not require any special measures, and a conventionally known developer suitable for each photosensitive composition can be used.
It can be developed. The photosensitive resist-forming composition imparted with the above-mentioned printout ability can be used for producing printing proof plates, films for overhead projectors, and films for second originals. Suitable supports include transparent films such as polyethylene terephthalate film and cellulose triacetate film, and these plastic films whose surfaces have been chemically or physically matted. Further, the above composition can also be used for producing a film for photomasks. Suitable supports include polyethylene terephthalate films deposited with aluminum, aluminum alloys, or chromium, and polyethylene terephthalate films provided with colored layers. Furthermore, the composition described above can be used as a photoresistor. In this case, various materials such as a steel plate, a copper plated plate, a stainless steel plate, a glass plate, etc. can be used as the support. [Effects of the Invention] When the free radical generating agent of the present invention is exposed to light in a photosensitive resist-forming composition containing various photosensitive resist-forming compounds, it decomposes and efficiently removes coexisting color-changing agents. It is amazing how well it changes color instantly. As a result, a clear boundary is obtained between the exposed and unexposed areas, which can be recognized as a visible image with rich contrast. Further, since a wide range of color changing agents can be used, an appropriate color changing agent can be selected when various additives are added to improve the performance of the photosensitive composition. Additionally, the free radical generators used in the present invention are stable over time, thereby improving the shelf life of these articles, for example when used in PS plates. Furthermore, the photodecomposition reaction of the free radical generating agent in the present invention is very fast and is not significantly inhibited by the coexisting photosensitive resist-forming compound, so that even a small amount added is effective. In addition, the free radical generating agent in the present invention does not significantly inhibit the photodecomposition of photosensitive resist-forming compositions, such as compositions (1) and (2), and therefore the photosensitivity of the photosensitive resist-forming compound (resist (photosensitivity)
does not decrease too much. Further, since the free radical generating agent according to the present invention is effective when added in a small amount, it does not deteriorate the physical properties of the resist image obtained after imagewise exposure and development of the photosensitive resist-forming composition. For example, when the photosensitive resist-forming compound imparted with printout ability according to the present invention is used as the photosensitive layer of a photosensitive lithographic printing plate, the developability, oil sensitivity, printing stains, printing durability, etc. of the printing plate obtained, etc. The various properties are the same as when no free radical generator is added. [Example] Hereinafter, the present invention will be explained in more detail with reference to Examples. Note that "%" is by weight unless otherwise specified.
shows. Example 1 Surface grained and then anodized, thickness 0.24mm
Apply the following photosensitive solution to an aluminum plate and heat it at 100℃.
and dried for 2 minutes. Esterification reaction product of naphthoquinone-(1,2)-diazide-(2)-5-sulfonyl chloride and cresol novolak resin 0.75g Cresol novolak resin 2.10g Tetrahydrophthalic anhydride 0.15g Free radical generator (first Items listed in the table) 0.03g Crystal Violet 0.01g Oil Blue #603 (manufactured by Orient Chemical Industry Co., Ltd.) 0.01g Ethylene dichloride 18g 2-methoxyethyl acetate 12g The coating solution after drying was 2.1g/cm ² . Each of these photosensitive lithographic printing plates was exposed to light for 40 seconds using a 2KW metal halide lamp from a distance of 1 meter through a positive transparency. The optical density of the exposed and unexposed areas of the photosensitive layer was measured using a Macbeth reflection densitometer. The image obtained by exposure appears sharper as the difference (ΔD) between the optical density of the exposed area and that of the unexposed area is larger. Also, gray scale (the optical density difference between two adjacent stages is 0.15, the optical density of the first stage is 0.1,
One with 15 steps. ) under the same conditions as above, and then immersed in a 4% sodium metasilicate aqueous solution at 25° C. for 1 minute to examine resist sensitivity. Sensitivity was indicated by the number of solid steps (the higher the number of steps, the higher the sensitivity). After exposure in the same manner as above through a positive transparent original, development was performed by rubbing with a sponge impregnated with a 4% sodium metasilicate aqueous solution, and unevenness in non-image areas (hand-developed unevenness) was examined. In Table 1, cases in which almost no unevenness appears are indicated by ○, and cases in which unevenness occurs are indicated by ×. On the other hand, in order to examine the ease with which stains (scumming) appear, these photosensitive planographic printing plates were treated with a tired developer and the presence or absence of stains was examined using a printing press. The results are shown in Table 1. As is clear from Table 1, according to the present invention, it was possible to provide a printout image, without lowering the sensitivity of the resist, and without causing unevenness in non-image areas during development. . In addition, with the known free radical generating agent cited as a comparative example, staining occurred in a tired developer (Experiment No.
7, No. 8), the free radical generating agent of the present invention did not cause staining, indicating that the present invention is extremely superior.

【table】

[Table] Example 2 The following photosensitive liquid was applied to an aluminum plate and dried in the same manner as in Example 1. Copolymer of methyl methacrylate and methacrylic acid (copolymerization molar ratio = 9:1) 0.62g Trimethylolpropane triacrylate 0.38g 2-benzoylmethylene-3-methyl-β-naphthothiazoline 0.02g Free radical generator [Examples] Compound (1)] 0.04 g Leucocrystal violet 0.008 g Methyl ethyl ketone 15 g The coating amount after drying was 2.5 g/cm ² . When this photosensitive lithographic printing plate was exposed to light through a transparent negative in the same manner as in Example 1, the exposed areas were colored purple and a printed image (printout) with rich contrast was obtained. Thereafter, unexposed areas were removed using a developer consisting of 1.2 g of caustic soda, 300 ml of isopropyl alcohol, and 900 ml of water to obtain a lithographic printing plate. In addition, in the above photosensitive liquid, a free radical generating agent (exemplary compound
When a photosensitive solution other than (1)) was used, almost no printed image appeared even when exposed in the same way. Example 3 The following photosensitive liquid was applied to the uncoated aluminum plate used in Example 1 using a Whaler. Drying is
This was carried out at 100°C for 2 minutes. p-Toluenesulfonate of condensate of p-diazodiphenylamine and paraformaldehyde 0.2g Polyvinyl formal 0.75g Free radical generator [Exemplary compound (2)] 0.02g Crystal violet 0.02g 2-methoxyethanol 20g Methanol 5g The dry coating amount was 1.0 g/m ² . This photosensitive lithographic printing plate was processed by a 1 kW metal halide run for 70 min.
When exposed for 30 seconds from a distance of 1.5 cm, a clear printout image with high contrast and fading of the exposed areas was obtained. It should be noted that when the above-mentioned photosensitive liquid was used without the free radical generating agent (exemplified compound (2)), a clear printout image could not be obtained. Example 4 The following photosensitive liquid was applied to an aluminum plate in the same manner as in Example 1 and dried. Polyester synthesized by condensation of ethyl p-phenylene diacrylate and equimolar amount of 1,4-bis-β-hydroxyethoxycyclohexane (molecular weight approximately 8000) 0.5g 2-benzoylmethylene-3-methyl-β-naphtho Thiazoline 0.03g Free radical generator (exemplified compound (14)) 0.008g Leucocrystal violet 0.008g Monochlorobenzene 9g Ethylene dichloride 6g The coating amount after drying was 1.5g/m ² . When this photosensitive lithographic printing plate was exposed through a transparent negative in the same manner as in Example 1, a printed image with rich contrast was obtained. The surface was then developed by wiping with a developer having the composition shown below to obtain a lithographic printing plate. In addition, compared to the case of using a photosensitive liquid in which the free radical generating agent [exemplified compound (14)] is excluded from the above photosensitive liquid,
The printed images were clearly clearer, and the sensitivity of the registers was almost the same. Developer composition γ-butyrolactone 1000ml Chrycerol 100ml Methyl abietate 10ml

Claims (1)

[Claims] 1 At the 5th position of the 1,3,4-oxadiazole nucleus,
2-halomethyl- to which a benzofuryl group having 1 to 2 hydroxyl groups is bonded directly or via a vinyl group
A photosensitive composition comprising a 1,3,4-oxadiazole free radical generating agent. 2 At the 5th position of the 1,3,4-oxadiazole nucleus,
2-halomethyl- to which a benzofuryl group having 1 to 2 hydroxyl groups is bonded directly or via a vinyl group
1. A photosensitive composition comprising a 1,3,4-oxadiazole free radical generating agent and a color changing agent that changes color due to a photodecomposition product of the free radical generating agent. 3 At the 5th position of the 1,3,4-oxadiazole nucleus,
2-halomethyl- to which a benzofuryl group having 1 to 2 hydroxyl groups is bonded directly or via a vinyl group
1. A photosensitive composition comprising a 1,3,4-oxadiazole free radical generating agent, a color change agent that changes color due to a photodecomposition product of the free radical generating agent, and an o-naphthoquinone diazide compound.