JPH0474172A - New sensitizer - Google Patents

Abstract

NEW MATERIAL:An aryl ketone derivative of formula I [R<1>,R<2>,R<3> are H, alkyl, alkoxy, nitro, OH; X is (CH2)l, O(CH2)m, etc.; l is 1-3; m is 0-2; p is 3-6). EXAMPLE:2-(4'-Piperidinobenxylidene)-1,3-indanedione. USE:A sensitizer. The compound of formula I has an excellent sensitizing action and is useful as a sensitizer for various photopolymerizable composition. PREPARATION:An active methylene compound of formula II is reacted with an aromatic aldehyde compound of formula III in the presence of a base (e.g. NaOH) in a solvent such as methanol at 70-110 deg.C to obtain the compound of formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a novel aryl ketone derivative useful as a sensitizer and a photopolymerizable composition containing the same.

[Prior Art] Conventionally, photopolymerizable compositions whose basic composition is a compound having an ethylenically unsaturated bond in the molecule and a photopolymerization initiator have not been cured or their tackiness has changed by irradiation with light. Or,
Utilizing these properties, such as insolubility in solvents, the field of application has expanded from simple resist materials to a wide range of fields such as paints, adhesives, molding materials, recording materials, and medical materials [for example, Ao Yamaoka, Nagamatsu et al. ``Photopolymer Technology'' written by Gentabe, Nikkan Kogyo Shimbun; 19B5, supervised by Kunihiro Ichimura; ``New Applications of Photofunctional Polymers, JCM, C, Inc.;
1988 etc.].

In addition, in recent years, attempts have been made to spectrally sensitize these photopolymerizable compositions to the visible region to form digital images using a visible light laser as a light source, and to apply them to full-color photosensitive materials. For example, “Journal of the Photographic Society of Japan” Vol. 49, No. 3, 23
0 page (1986) and “Functional Materials” September issue pp. 48-60
(1983) discloses a method for spectral sensitization of photopolymerizable compositions for use in visible light laser recording. Further, JP-A-59-189340 describes a method of spectrally sensitizing an organic peroxide initiator with an organic dye.

Further, European Patent No. 223.587 discloses an organic boron anion salt of an organic cationic dye as a new photopolymerization initiator. Examples of combinations of local polymerization initiators and visible light sensitizers include diarylketones and 2
．． 4.5-Triarylimidazolyl dimer initiator system (
JP-A-1-103603), an initiator system in which the conjugated system is further expanded with a thioxanthone compound (JP-A-60-2214)
03), thiopyrylium salt and benzoin initiator system (JP-A-53-278903), aminobenzylidene carbonyl compound and N-aryl-α amino acid initiator system (JP-A-1-131205), cationic dye and borate anion Examples include an initiator system containing a salt of (JP-A-1-152450).

In particular, in recent years, there has been a demand for photosensitive materials that are sensitive to hologram recording used in posters, credit cards, CD packaging, etc., and argon ion lasers and helium-neon gas lasers used in direct plate making to directly print digital image information. It is being As a visible light sensitizer that can meet these demands, JP-A-2-69
No. 2-869, JP-A No. 2-8585
New sensitizer systems are disclosed in Japanese Patent No. 7 and Japanese Patent Application Laid-Open No. 2-85858.

[Problem to be solved by the invention]

However, the sensitivity of conventional sensitizers is still unsatisfactory, and photopolymerizable compositions using these sensitizers are also unsatisfactory in the field of photosensitizers.

Therefore, it has been desired to develop a highly sensitive sensitizer and a photopolymerizable composition using the same.

[Means to solve the problem]

Under these circumstances, the present inventors have conducted extensive research in search of a sensitizer with higher sensitivity, and have found that an aryl ketone derivative having a nitrogen-containing saturated heterocycle represented by the following general formula (I) exhibits extremely high sensitization. The present inventors have discovered that an excellent photopolymerizable composition can be obtained by using the same, and have completed the present invention.

That is, the present invention represents an aryl ketone derivative represented by the following general formula (1) (representing an integer of 2 to 2), n represents an integer of 0 to 2, and p represents an integer of 3 to 6. The present invention provides a sensitizer and a photopolymerizable composition containing the same.

The aryl ketone derivative of the present invention is represented by the general formula (I), and in the formula (I), R1, R2 and R3
Examples of the alkyl group represented by include methyl group, ethyl group, propyl group, butyl group, etc.; examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, butoxy group, etc. Further, specific examples of particularly preferred compounds of the present invention are as follows.

[In the formula, R1, R2 and R3 each represent a hydrogen atom, an alkyl group, an alkoxy group, a nitro group or a hydroxyl group, and
is 1+C)12+r, -C+Ct12h, -0-
GeH4-)-t- or -3+CI(*h (where 1 is an integer of 1 to 3, m is 0) Compound 17 Compound 22 The aryl ketone derivative (1) of the present invention is , for example, according to the following reaction formula (A) or (B).

Reaction formula (A): Compound of the present invention 23 Compound of the present invention 24 Compound of the present invention 25 2115 [In the formula, R1, R2, R3, ) and the aromatic aldehyde compound (I [I) in the presence of a base to produce the aryl ketone derivative (I) of the present invention. This reaction is carried out in the presence of a base such as sodium hydroxide, potassium hydroxide, sodium carbonate, pyridine, piperidine, etc., in a solvent such as methanol, ethanol, isopropyl alcohol, toluene, benzene, etc.
Preferably, the temperature is 110°C.

Reaction formula (B): (V) [In the formula, Y represents a halogen atom, R1, R2, R3,
X, n and p have the same meanings as above; that is, active methylene compound (■), aromatic aldehyde compound (r
The aryl ketone derivative (I) of the present invention is produced by reacting V) and the alicyclic amine (V). This reaction is preferably carried out in a solvent such as methanol, ethanol, isopropyl alcohol, toluene, benzene, etc. at the reflux temperature of the solvent.

The aryl ketone derivative (I) obtained as described above has an excellent sensitizing effect and is useful as a sensitizer for various photopolymerizable compositions. Therefore, the aryl ketone derivative (■
) (component (c)), (a) one ethylenically unsaturated bond
A highly sensitive photopolymerizable composition can be obtained by blending a polymerizable compound having at least 1 or more photopolymerizable compounds and (b) a photopolymerization initiator.

The polymerizable compound having one or more ethylenically unsaturated bonds used in the photopolymerizable composition of the present invention includes the following: ``When the composition is irradiated with ultraviolet rays or near ultraviolet rays, polymerization occurs due to the action of generated free radicals. The compound is not particularly limited as long as it causes a reaction, hardens, and becomes substantially insolubilized, and includes monomers, dimers, trimers, oligomers, so-called macromonomers, etc. Specifically, for example, Examples include unsaturated carboxylic acids, esters of unsaturated carboxylic acids and aliphatic polyhydroxy compounds, esters of unsaturated carboxylic acids and aromatic polyhydroxy compounds, and vinyl urethane compounds.

Specific examples of esters of aliphatic polyhydroxy compounds and unsaturated carboxylic acids include ethylene glycol diacrylate, triethylene glycol diacrylate, trimethylolpropane triacrylate, trimethylolethane triacrylate, pentaerythritol diacrylate, and pentaerythritol triacrylate. Acrylic acid esters such as acrylate, pentaerythritol tetraacrylate, dipentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, glycerol acrylate; triethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, trimethylolethane trimethacrylate , pentaerythritol dimethacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, dipentaerythritol dimethacrylate, dipentaerythritol trimethacrylate, dipentaerythritol tetramethacrylate, and other methacrylic acid esters; ethylene glycol shiitaconate, tetramethylene glycol shiitaconate itaconate esters such as ester, pentaerythritol triitaconate; crotonate esters such as ethylene glycol dicrotonate, diethylene glycol dicrotonate, pentaerythritol tetracrotonate; ethylene glycol dimaleate, triethylene glycol dimaleate, hentaerythritol Examples include tumarate esters such as dimaleate.

The ester of the aromatic polyhydroxy compound and unsaturated carboxylic acid includes hydroquinone diacrylate,
Examples include hydroquinone dimethacrylate, resorcin diacrylate, resorcin dimethacrylate, and pyrogallol triacrylate.

Examples of the vinyl urethane compound include amides such as methylenebisacrylamide and compounds obtained by adding a vinyl monomer to a polyisocyanate compound.

These polymerizable compounds (a) may be used alone or in combination of two or more.

The photopolymerization initiator (b) used in the present invention is the component (c)
Any compound can generate active radicals when irradiated with light in the coexistence with a sensitizer, such as hexaarylbiimidazole, organic halogen compounds, organic peroxides, diaryliodonium salts, and amine compounds. ,
Examples include aromatic ketone compounds.

Specific examples of hexaarylbiimidazole include 2,
2'-bis(0-chlorophenyl)-4゜4', 5
．． 5'-tetraphenylbiimidazole, 2゜27-
Bis(0-bromophenyl)-4,4',5゜5'-tetraphenylbiimidazole, 2,2'-bis(0,p
-dichlorophenyl)-4,4', 5゜5'-tetraphenylbiimidazole, 2.2'-bis(0-chlorophenyl)-4,4', 5. 5'-tetra (m-
methoxyphenyl)biimidazole, 2,2'-bis(
o, o'-dichlorophenyl)-4, 4', 5
．． 5'-tetraphenylbiimidazole, 2.2'-
Bis(0-nitrophenyl)-4,4'.

5.5'-tetraphenylbiimidazole, 2.2'-
Bis(0-methylphenyl)-4,4', 5.
Examples include 5'-tetraphenylbiimidazole.

Examples of organic halogen compounds include p-nitrobenzotribromide, bromotrichloromethane, hexabromoethanebensitrichloride, 1,1°1-)'Jbromo2-methyl-2-propatol, 1.1.2.2- Tetrabromoethane, 2,2゜2-tribromoethanol, 1.1.1-)dichloro-2-methyl-propanol, 0-nitro-α,α,α-tribromoacetophenone, m-nitro-α, α, α-tribromoacetophenone, p-nitro-α, α, α-tribromoacetophenone, α, α, α-tribromoacetophenone, α, α, α
-m-tetrabromoacetophenone, α, α, α-tribromo 3.4-dichloroacetophenone, α, α, α
-p-tetrabromoacetophenone, α, α, α, α′
, α', α'-hexabromo-p-diacetylbenzene, ω, ω, ω-tribromomethyl-4-methylquinoline, ω, ω-dichloromethyl-quinoline, ω-promlepidine, 2-ω-bromomethyl Isoquinoline, 4-ω.

ω, ω-tribromo-methylpyrimidine, 4-phenyl-6-ω, ω-tribromomethylpyrimidine, 2-ω
, ω, ω-trichloromethyl-6-nitropenzothiazole, 1-phenyl-3-ω.

ω, ω-trichloro-5-methylpyrazole, ω.

ω, ω-tribromo lepidine benzimidazole,
2.5-ditribromomethyl-3,4-dibromothiophene, hexabromodimethyl sulfoxide, pentabromodimethyl sulfoxide, hexabromodimethyl sulfone, trichloromethyl phenyl sulfone, tribromomethyl phenyl sulfone, trichloromethyl-p -chlorophenylsulfone, tribromomethyl-p-nitrophenylsulfone, 2-trichloromethyl-benzothiazolylsulfone, 4,6-dimethylpyrimidyl-2-)
! I dibromotylsulfone, tetrabromodimethylsulfone, 2,4-dichlorophenyltrichloromethylsulfone, 2-methyl-4-chlorophenyltrichloromethylsulfone, 2,5 dimethyl-4-chlorophenyltrichloromethylsulfone, 2,4-dichlorophenyltribromomethyl Sulfone, 1,3-benzenesulfonyl chloride, 2,4-dinitrobenzenesulfonyl chloride, 0-nitrobenzenesulfonyl chloride, m-nitropennesulfonyl chloride, 3.3
'-diphenylsulfone disulfonyl chloride,
Ethanesulfonyl chloride, p-bromobenzenesulfonyl chloride, p-nitrobenzenesulfonyl chloride, p-iodobenzenesulfonyl chloride, p-acetamidobenzenesulfonyl chloride, p-chlorobenzenesulfonyl chloride, p-
Toluenesulfonyl chloride, methanesulfonyl chloride, benzenesulfonyl chloride, m-nitrobenzenesulfonyl fluoride, benzenesulfonyl chloride, 2,4-dinitrobenzenesulfenyl chloride, 0-nitrobenzenesulfenyl chloride, 2.4.6 -Tris (trichloromethyl)
S-triazine, 2. 4. 6-
) Lis(tribromomethyl)-S-)riazine and the like.

As organic peroxides, 3. 3', 4. 4'-
Tetra-(1-butylberoxycarbonyl)benzophenone, 3. 3', 4. 4'-tetra-(t-
amylperoxycarbonyl)benzophenone, 3.3
'.

4.4'-tetra-(1-hexylperoxycarbonyl)benzophenone, 3. 3', 4. 4'-tetra-(t-octylperoxycarbonyl)benzophenone, 3. 3', 4. 4'-tetra-(cumylperoxycarbonyl)benzophenone, 3.3'.

Examples include 4'-tetra-(p-isopropylcumylberoxycarbonyl)benzophenone. Examples of diaryliodonium salts include diphenyliodonium hexafluoroacetate, diphenyliodonium chloride, 4-chlorophenyl-phenyliodonium chloride, di(4-chlorophenyl)iodonium chloride, 4-trifluoromethylphenyl-phenyliodonium chloride, 4-ethylphenylphenyliodonium Chloride, di(4-acetylphenyl)
Iodonium iodite, anisylphenyliodonium hexafluoroborate, 4-butoxyphenyl-phenyliodonium hexafluoroborate, di(4-
Phenylphenyl)iodonium chloride, di(carbomethoxyphenyl)iodonium hexafluorophosphate, 4-methoxyphenyl-phenyliodonium hexafluorophosphate, 4-ethoxyphenyl-phenyliodonium chloride, diphenyliodonium-hexafluorophosphate, etc. . As an amine compound, (dihydroxyethyl)
Methylamine, trihydroxyethylamine, ethyl p-dimethylaminobenzoate, 2-butoxyethyl p-dimethylaminobenzoate, N-phenylglycine, N-butyl-N-phenylglycine, N-ethyl N-phenylglycine, etc. It will be done. Aromatic ketone compounds include benzophenone, 4.4'dimethylbenzophenone,
Examples include thioxanthone, Michler's ketone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-butylthioxanthone, and 2-isopropylthioxanthone.

Among these photopolymerization initiators (b), 2,2'-bis(
0-chlorophenyl)-4,4', 5. 5'-tetraphenylbiimidazole, 2,2'-bis(.

bromophenyl) -4,4', 5. 5'-tetraphenylbiimidazole, 3. 3', 4. 4
Particularly preferred are '-tetra(1-butylperoxycarbonyl)benzophenone, N-phenylglycine, and N-butyl-N-phenylglycine.

The photopolymerization initiator (b) in the present invention may be used alone or in combination of two or more, and the amount thereof is as follows:
The amount of the ethylenically unsaturated compound (1 to 60 parts by weight is preferably 1 to 60 parts by weight, particularly preferably 5 to 30 parts by weight, based on 8000 parts by weight). If the amount is too small, the sensitivity of the photopolymerizable composition will decrease; if it is too large, the image quality will deteriorate. Contrast is reduced.

The aryl ketone derivative (I), which is the component (c) in the photopolymerizable composition of the present invention, can be used alone or in a mixture of two or more kinds, and the amount of the aryl ketone derivative (I) is determined by adjusting the amount of the above-mentioned ethylenically unsaturated compound ( It is preferably 0.1 to 30 parts by weight based on 8000 parts by weight, and particularly preferably 0.3 to 15 parts by weight. If it is too small, the sensitivity of the photopolymerizable composition will decrease, and if it is too large, the image contrast will decrease. .

Further, additives such as a polymeric binder, a chain transfer agent, a thermal polymerization inhibitor, a plasticizer, etc. can be added to the photopolymerizable composition of the present invention, if necessary.

The polymeric binder is a film-forming polymer and may be any compound that binds the other photopolymerizable composition to the support. Preferably, a binder should be selected that allows development in alcohol or water or weakly alkaline water. For example, water-developable polymeric binders include methacrylic acid copolymers, acrylic acid copolymers, itaconic acid copolymers, crotonic acid copolymers, maleic acid copolymers, and partially esterified maleic acid copolymers. Conventionally known organic polymers such as , acidic cellulose copolymers, polyvinylpyrrolidone, gelatin, polyvinyl alcohol, polyvinyl butyral, and polyethylene oxide are useful.

As the chain transfer agent, organic sulfur compounds such as 2-mercaptobenzoxazole, 2-mercaptobenzthiazole, and 2-mercaptobenzimidazole are useful.

Thermal polymerization inhibitors include hydroquinone, hydroquinone monomethyl ether, ■-butylcatechol, p-benzenequinone, 2゜5-di-t-butylhydroquinone, phenothiazine, p-aminophenol, 4-phenylpyridine-N-oxide, , 6-di-t-butylcresol, cholic acid, methyl m-hydroxybenzoate, and other conventionally known organic compounds are useful. As the plasticizer, conventionally known organic compounds such as dioctyl phthalate, didodecyl phthalate, triethylene glycol cabrilate, dimethyl glycol phthalate, tricresyl phosphate, dioctyl adipate, dibutyl sebacate, and triacetylglycerin are useful. These additives may be used alone or in combination.

A photosensitive material can be prepared by coating the thus obtained photopolymerizable composition of the present invention on a support without a solvent or by dissolving it in a suitable solvent and then drying it. Here, the thickness of the photosensitive layer is 0.5 mm to 2 mm for boat fishing, but 1 mm to 30 mm.
A trend is more preferable. Examples of the solvent used include toluene, xylene, monochlorobenzene, 0-dichlorobenzene, chloroform, carbon tetrachloride, amyl acetate, ethyl propionate, cyclohexanone, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, methyl cellosolve, ethyl cellosolve, and acetone. , methanol, ethanol, etc.

Supports used include, for example, aluminum, copper,
Sheets of metals such as zinc, iron, chromium, nickel, etc., or alloys containing these as main components Papers ranging from high-quality paper to cardboard, glass, inorganic sheets such as ceramics, polyethylene phthalate, acidic cellulose, polyethylene,
Examples include polymer films such as polystyrene. If necessary, a conventionally known subbing layer may be applied to the surface of the support.

In addition, the photopolymerizable composition of the present invention can be used by forming an oxygen blocking layer on the photosensitive layer using a known technique in order to reduce the permeability of oxygen, which causes photofading of the sensitizer and inhibition of the polymerization reaction. Accordingly, it is possible to further improve the sensitivity. Specifically, a transparent film such as a polyethylene terephthalate film may be pressed onto the photosensitive layer, or a water-soluble polymer such as polyvinyl alcohol may be applied to provide a coating layer. The thickness of this coating layer is generally 8 to 80 mm, more preferably 10 to 50 mm.

As an exposure light source for forming a photopolymerized image using the photosensitive material thus obtained, any light source that emits visible light of 400 nm or more may be used.

Specifically, examples include light sources that emit non-coherent light such as carbon arc lamps, high-pressure mercury lamps, mercury-cannon lamps, xenon lamps, metal halide lamps, fluorescent lamps, tungsten lamps, magnesium lamps, LBDs, argon ion racers, helium neon racers, etc. , an excimer laser, a dye laser, a nitrogen laser, and other light sources that emit coherent light.

The photopolymerizable compositions of the invention have a wide range of applications, e.g.
Production of PS plates used in offset printing, recording materials such as photoresists, dry films, and holograms for production of printed wiring boards and ICs, image forming materials such as relief images and image reproductions, photocurable inks, Can be used for paints, adhesives, etc.

〔Example〕

The present invention will be explained below with reference to Examples, but the present invention is not limited thereto.

Synthesis Example 2 - Synthesis of (4'-piperidinobenzylidene)-1,3-indanedione (inventive compound 1): 21.9 g (0.15 mol) of 1°3-indane in 100 toluene 12. Dissolve the dione and 18.6 g (0.15 mol) of p-fluorobenzaldehyde and with stirring.
8g of piperidine was added slowly. This reaction mixture was
The mixture was heated to reflux for an hour. After cooling, the precipitated crystals were filtered, washed with ethanol, and purified using a column to obtain 12.5 g (yield 26.3%) of red needle-like crystals of 2-(4'-piperidinobenzylidene)-1. 3-indandione (melting point 183-185°C) was obtained.

Elemental analysis value C) IN Calculated value 79.47 6.03 4.41 Analysis value 79
．． 38 6.08 4.40 The infrared absorption spectrum and nuclear magnetic resonance spectrum are shown in Figures 1 and 2, respectively.

The compounds 2 to 25 of the present invention described above can also be obtained in the same manner.

Example 1 10 parts by weight of polyvinylpyrrolidone with an average molecular weight of 360,000,
10 parts by weight of pentaerythritol tetraacrylate (manufactured by Shin Nakamura Chemical Co., Ltd., NK Ester A-TMMT), 1 part by weight of the sensitizer listed in Table 1, 0.8 part by weight of N-butyl-N-phenylglycine, and methyl cellosolve. 10
0 parts by weight were mixed to prepare a photosensitive liquid. This photosensitive solution was spin-coated onto an aluminum support and then heated at 40°C for 30 minutes.
Dry for 0 minutes. The dry film thickness is approximately 1. A sample of OIIm was prepared.

Next, a 500W xenon lamp was used as a light source, and a 490W
After exposing the sample to visible light through an interference filter (Asahi spectroscopic side) that passes only nm light, or to light from a 488 nm single line of an argon laser focused to a beam diameter of 1.5 m++, the uncured area was removed with ethanol. It was eluted and removed, stained with a methyl blue ethanol solution, and the presence or absence of hardening was visually determined. The minimum light energy required to cure the coating film was defined as the sensitivity (Table 1). As for the sensitivity in this table, the smaller the value, the higher the sensitivity.

The following margin compound 26: Table compound 27: described in No. 155292) (described in JP-A-54-155292) Example 2 Polymethyl methacrylate binder (manufactured by DuPont Japan Limited, Elvacite 2008) 5 parts by weight, polyethylene glycol dimethacrylate (manufactured by Shin Nakamura Chemical Industry ■, NK Ester 9PG) 5 parts by weight, 0.5 parts by weight of the sensitizer listed in Table 2, 2.2'bis(0-chlorophenyl)-4,4', 5. 1.5 parts by weight of 5'tetraphenylbiimidazole, 1 part by weight of 2°27-cythiobis(benzoxazole), polyoxyethylene lauryl ether (manufactured by Kao Aji Co., Ltd.).

1 part by weight of Emulgen 105) and 100 parts by weight of methylene chloride were mixed to prepare a photosensitive liquid. This photosensitive solution was spin-coated onto a 2 mm thick glass plate, and then heated at 40°C for 30 minutes.
Dry for a minute. A sample with a dry film thickness of approximately 1.5/7+11 was prepared.

Next, exposure was performed in the same manner as in Example 1, and then a general-purpose toner was applied to the uncured portion, and the presence or absence of curing was visually determined. The minimum light energy required to cure the coating layer was defined as the sensitivity (Table 2).

Margins below the table Example 3 10 parts by weight of polyvinyl butyral (S-LEC BM-1, manufactured by Block Chemical Industry ■), pentaerythritol triacrylate (manufactured by Shin Nakamura Chemical Industry ■, NK ester^)
-TMM-3L) 10 parts by weight, 1 part by weight of the sensitizer listed in Table 3, 3. 3', 4. 4'-tetra-(t
A photosensitive liquid was prepared by mixing 0.8 parts by weight of 2,6-di-t-butylcresol, 50 parts by weight of methyl cellosolve, and 50 parts by weight of methanol.

This photosensitive solution was spin coated onto an aluminum support and then dried at 40°C for 30 minutes. A sample having a dry film thickness of approximately 1.0 IIrn was prepared.

Next, the film was exposed and developed in the same manner as in Example 1, and the sensitivity was determined (Table 3).

Margins below [Effects of the Invention] As described above, the compounds of the present invention are useful as sensitizers with extremely high sensitivity, and photopolymerizable compositions containing the sensitizers are useful as photosensitive materials in a wide range of fields. be.

[Brief explanation of the drawing]

FIG. 1 shows an infrared absorption spectrum of Compound 1 of the present invention, and FIG. 2 shows a nuclear magnetic resonance spectrum of the same compound. that's all

Claims (1)

[Claims] 1. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [In the formula, R^1, R^2, and R^3 are each a hydrogen atom, an alkyl group, or an alkoxy group, nitro group, or hydroxyl group, and X is a ▲ mathematical formula, chemical formula, table, etc.
There are chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (Here l is 1 to 3
, m is an integer from 0 to 2), and n is an integer from 0 to 2.
p is an integer of 3 to 6.] An aryl ketone derivative represented by the following. 2. A sensitizer comprising the aryl ketone derivative according to claim 1. 3. The following components (a), (b) and (c) (a) A polymerizable compound having one or more ethylenically unsaturated bonds (b) A photopolymerization initiator (c) The aryl ketone derivative according to claim 1 A photopolymerizable composition containing.