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Photopolymerizable composition, color filter, method for producing same, solid-state image pickup element, liquid crystal display device, lithographic printing original plate, and novel compound

一种光聚合性、组合物的技术，应用在光聚合性组合物,新型化合物领域，能够解决灵敏度不足、曝光时间变长、成品率降低等问题

Active Publication Date: 2012-05-30
FUJIFILM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When a large amount of color material is added to obtain a high color density, the sensitivity is insufficient to faithfully reproduce the shape of a fine pixel pattern of 2.5 μm or less, and many patterns tend to be missing as a whole.
In addition, in order to eliminate this chip, light irradiation with higher energy is required, so there is a problem that the exposure time becomes longer, and the decrease in manufacturing yield becomes noticeable.

Method used

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  • Photopolymerizable composition, color filter, method for producing same, solid-state image pickup element, liquid crystal display device, lithographic printing original plate, and novel compound
  • Photopolymerizable composition, color filter, method for producing same, solid-state image pickup element, liquid crystal display device, lithographic printing original plate, and novel compound
  • Photopolymerizable composition, color filter, method for producing same, solid-state image pickup element, liquid crystal display device, lithographic printing original plate, and novel compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0415] Hereinafter, although an Example demonstrates this invention more concretely, this invention is not limited to the following Example unless the summary is exceeded. In addition, unless otherwise indicated, "part" means a mass basis, and "%" means "mass %".

[0416] First, details of the specific oxime compounds (Specific Compound 1 to Specific Compound 11) used in Examples and comparative compounds (Comparative Compound 1 to Comparative Compound 4) used in Comparative Examples are given.

[0417] The synthesis method of Specific Compound 1 to Specific Compound 11 is shown below.

[0418]

[0419]

[0420]

[0421] (Synthesis of α Heterocompounds)

[0422] ·Synthesis of α-morpholino isobutyrate hydrochloride

[0423] Dilute ethyl 2-bromopropionate (0.125 mol) in 75 mL of toluene, add formalin (0.3 mol), and stir at room temperature for 10 hours. After removing the white solid by filtration, the filtrate was distilled to obtain ethyl 2-morpholinopropionate (0....

Synthetic example 1

[0435] [Synthesis Example 1] Synthesis of Specific Compound 1 as Specific Oxime Compound

[0436] 1-[6-(2-methylbenzoyl)-9-ethyl-9H-carbazol-3-yl]ethanone oxime (12mmol) and α-morpholino isobutyrate hydrochloride (12mmol ) was suspended in 20 mL of dichloromethane. After cooling this to 0°C, 4-dimethylaminopyridine (24 mmol) and dicyclohexylcarbodiimide (13 mmol) were added thereto, followed by stirring at 0°C for 1 hour. After extraction with chloroform, it was washed with a saturated aqueous sodium chloride solution, the organic layer was dried over magnesium sulfate, and the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (hexane / ethyl acetate=4 / 1) to obtain 7.6 mmol of the target specific compound 1 .

[0437] The structure of the obtained specific compound 1 was identified by NMR.

[0438] ( 1 H-NMR 300MHz deuterated chloroform): 1.47(s, 6H,), 1.49(t, 3H, J=7.2Hz), 2.35(s, 3H), 2.52(s, 3H), 2.74(t, 4H, J =4.5Hz), 3.75(...

Synthetic example 2

[0440] [Synthesis Example 2] Synthesis of Specific Compound 2 as Specific Oxime Compound

[0441] In Synthesis Example 1, it was synthesized by the same method as Specific Compound 1, except that α-diethylaminoisobutyrate hydrochloride was used instead of α-pyrrolidine isobutyrate hydrochloride.

[0442] The structure of the obtained specific compound 2 was identified by NMR.

[0443] ( 1 H-NMR 300MHz deuterated chloroform): 1.45(s, 6H,), 1.49(t, 3H, J=7.2Hz), 1.55(t, 6H, J=7.2Hz), 2.35(s, 3H), 2.54( s, 3H), 2.90(m, 4H), 4.42(q, 2H, J=7.2Hz), 7.26~7.47(m, 6H), 7.98(d, 1H, J=8.4Hz), 8.11(d, 1H , J=8.4Hz), 8.45(s, 1H), 8.52(s, 1H)

[0444] The molar absorptivity at 365 nm of Specific Compound 2 was measured in the same manner as above, and it was 1600 in ethyl acetate.

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Abstract

Disclosed is a photopolymerizable composition which contains (A) a photopolymerization initiator that has a partial structure represented by general formula (1) and (B) a polymerizable compound. In general formula (1), R3 and R4 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group or an alkoxy group,R3 and R4 may form a ring with each other,and X represents OR5, SR6, or NR17R18. The photopolymerizable composition is capable of forming a cured film that has high sensitivity, excellent curability with respect to the inner part of the film, and excellent adhesion to a supporting body. The cured film is able to maintain a patterned shape even during post-heating after development and has good pattern formability, while being suppressed in coloring due to heating or passage of time.

Description

technical field [0001] The present invention relates to a photopolymerizable composition, a color filter made of a photopolymerizable compound, a method for producing the same, a solid-state imaging device including the color filter, a liquid crystal display device, a lithographic printing plate precursor, and the photopolymerizable compound Contains novel compounds. Background technique [0002] As a photopolymerizable composition, the composition which added the photopolymerization initiator to the polymerizable compound which has an ethylenically unsaturated bond is mentioned, for example. Such a photopolymerizable composition polymerizes and cures when irradiated with light, and thus is used in photocurable inks, photosensitive printing plates, color filters, various photoresists, and the like. [0003] In addition, as a photopolymerization initiator, there is, for example, a method in which an acid is generated by irradiation with light, and the generated acid is used ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G03F7/031C07D209/82C07D295/14C07D335/06C07D339/08C07D491/048G02B5/20G02F1/1335G03F7/00G03F7/004H01L27/14
CPCC07D311/68C07D209/82C07D209/86C07D339/08C07D295/12G02B5/223C07D335/06C07D339/06G03F7/031H01L27/14621G03F7/0007C07D295/20C07D491/04C07D491/048G02F1/133516H01L27/14643G02F2202/023C07D295/14C07D209/88C09K2323/031G02B5/201G03F7/0045C09K19/00
Inventor 牧野雅臣
Owner FUJIFILM CORP
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