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Oxime ester compound and photopolymerization initiator containing said compound

A technology of compound and oxime ester, which is applied in the field of oxime ester compound and photopolymerization initiator containing the compound, which can solve the problems of low transmittance and brightness reduction

Pending Publication Date: 2019-07-16
ADEKA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If the transmittance in the visible light region is low, there will be problems such as a decrease in brightness

Method used

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  • Oxime ester compound and photopolymerization initiator containing said compound
  • Oxime ester compound and photopolymerization initiator containing said compound
  • Oxime ester compound and photopolymerization initiator containing said compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0275] [Example 1] Production of Compound No.1

[0276] (Step 1) Production of Intermediate 1A (Haloaryl Compound)

[0277] In a 100ml 4-neck flask, weigh 2-chloro-4'-fluoroacetophenone (3.59g), salicylic acid aldehyde (5.08g), potassium carbonate (5.75g), acetone (15g) respectively, and then carry out Heat to reflux for 1 hour. After cooling to room temperature, ion-exchanged water (41.6 g) was added, and the precipitate was collected by filtration and fully dried to obtain intermediate 1A (4.74 g: yield 95%) as a pale yellow solid.

[0278]

[0279] Intermediate 1A

[0280] (Step 2) Production of intermediate 1B (ketone compound)

[0281] In a 100ml 4-neck flask, weigh intermediate 1A (4.42g), the following indole compound 1A (4.07g), potassium carbonate (4.62g) and DMAc (23.25g), and then react at 110°C for 3 Hour. Ion-exchanged water (15.5 g) and ethyl acetate (23.25 g) were added, oil-water separation was performed, and the organic layer was washed with water thre...

Embodiment 2

[0293] [Example 2] Production of compound No.189

[0294] (Step 1) Production of Intermediate 2A

[0295] After adding 9.6 g of the above intermediate 1B, 30.0 g of dimethylacetamide, and 2.2 g of hydroxylamine hydrochloride, 1.2 g of sodium hydroxide was added at 60°C. After making it react at 60 degreeC for 2 hours, ion-exchange water and chloroform were added, and it extracted, heating. The organic layer was washed 3 times with water, and the solvent was removed, followed by purification through a silica gel column (ethyl acetate / hexane=1 / 6) to obtain the following intermediate 2A (2.0 g: yield 25%).

[0296]

[0297] (Step 2) Production of compound No. 189 (oxime ester compound of the present invention)

[0298] Compound No. 189 was obtained in the same manner as in Step 4 of Example 1, except that Intermediate 1C was changed to Intermediate 2A.

Embodiment 3

[0299] [Example 3] Production of compound No.190

[0300] (Step 1) Production of Intermediate 3B

[0301] The following intermediate body 3B was obtained in the same manner as in Step 2 of Example 1, except that the indole compound 1A was changed to the following carbazole compound 3A.

[0302]

[0303] (Step 2) Production of Intermediate 3C

[0304] 2.72 g of aluminum chloride and 30.0 g of dichloroethane were added to a 100 ml 4-neck flask, and 7.54 g of intermediate 3B was added under ice-cooling, followed by 3.32 g of octanoyl chloride. After allowing to react at room temperature for 1 hour, the reaction solution was poured into ice water for oil-water separation. After the organic layer was washed with water three times, the solvent was removed, and the following intermediate 3C was obtained through a silica gel column (ethyl acetate / hexane=1 / 10) (1.1 g: yield 11%).

[0305]

[0306] (Process 3) Manufacture of No.190

[0307] The above-mentioned Compound No. 190...

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Abstract

Provided is an oxime ester compound represented by general formula (Ialpha) or (Ibeta). (In the formulae: R1 to R6 and R101 to R108 each independently denote a group represented by general formula (II), a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, or the like; one of R1 to R6 and R101 to R108 is a group represented by general formula (II); R7 to R11 and R109 to R113 each independently denote a group represented by general formula (IIIalpha) or (IIIbeta), a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, or the like; at least one of R7 to R11 and R109 to R113 is a group represented by general formula (IIIalpha) or (IIIbeta); and X1 and X101 are either not present or are each a direct bond,-CO-, -O- or -S-).

Description

technical field [0001] The present invention relates to a novel oxime ester compound useful as a photopolymerization initiator used in a photosensitive composition, a photopolymerization initiator containing the compound, and a photosensitive composition containing the photopolymerization initiator and an ethylenically unsaturated compound things. Background technique [0002] The photosensitive composition is obtained by adding a photopolymerization initiator to an ethylenically unsaturated compound, and can be polymerized and cured by irradiating energy rays (light), so it can be used for photocurable inks, photosensitive printing plates, various A photoresist, etc. [0003] As a photopolymerization initiator used in the above-mentioned photosensitive composition, a highly sensitive oxime ester photoinitiator having an aromatic heterocyclic ring is disclosed in the following patent document 1, and a photoinitiator having an aromatic heterocycle at 365 to 405 nm is disclos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/10C07D307/80C07D333/56C07D405/14C07D409/10C07D409/14C07D417/10C07D417/14C08F2/48G03F7/004G03F7/031
CPCC07D307/80C07D333/56C07D405/10C07D405/14C07D409/10C07D409/14C07D417/10C07D417/14C08F2/48G03F7/004G03F7/031C08F2/50G03F7/105
Inventor 竹内良智三原大树
Owner ADEKA CORP
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