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Asymmetric dioxime ester compound, making method and application thereof

A technology of compounds and general formulas, applied in applications, oxime preparation, thioether preparation, etc., can solve the problems of increased molecular weight, low activity of oxime esters, and no improvement in photosensitivity

Active Publication Date: 2015-09-16
INSIGHT HIGH TECH (BEIJING) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The substituted carbazolooxetane oxime ester described in Chinese patent CN102046667B has an absorption wavelength of up to 405nm, which is conducive to curing with LED lamps and visible light, but reduces the initiation activity per unit mass due to its increased molecular weight; patent Various dioxime ester derivatives based on phenylcarbazole disclosed in WO2008138732 have two oxime ester groups in one molecule, and one oxime ester is at the para-position of phenyl on the N substitution position. Experiments have proved that, Such oxime esters have very low activity and cannot make additional contributions to the photoinitiating activity of the molecule, so they are not practical;
[0005] In addition, there are many other patents of oxime ester photoinitiators, such as: WO2006018973, WO2007071497, CN1805955B, CN1922142B, CN1928715A, CN101508744B, CN102020727, but they are all side chains at the 3, 6, and 9 positions of carbazole Various modifications are carried out on the surface, and some molecular weights increase without any improvement in the photosensitivity

Method used

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  • Asymmetric dioxime ester compound, making method and application thereof
  • Asymmetric dioxime ester compound, making method and application thereof
  • Asymmetric dioxime ester compound, making method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0128] Example 1 Synthesis of 5-phenylthioindan-1-one

[0129]

[0130] Weigh 33.3g (0.2mol) of 5-chloro-1-indanone in a 50ml three-necked flask, add 30ml of N,N-dimethylformamide (DMF), 30.0g (0.27mol) of thiophenol, and 36g of anhydrous carbonic acid Potassium, nitrogen protection, stirring at 40-45°C for 6h; recover DMF under reduced pressure, add the residue to 100ml water, extract twice with 25ml 1,2-dichloroethane, combine the 1,2-dichloroethane solution, and use Wash twice with 10ml of water, spread filter paper in a Buchner funnel, use it to filter the organic phase, concentrate the filtrate to dryness, recrystallize the residue with methanol, and obtain 43.4g of light yellow crystals after drying, the yield is 90.3%, and the purity is analyzed by HPLC 98.2%. The melting range is 46.0-48.0°C.

Embodiment 2

[0131] Example 2 Synthesis of 5-(4-octanoylphenylthio)indan-1-one

[0132]

[0133] Weigh 24.04g (0.1mol) of the product 5-phenylthioindan-1-one of Example 1 and dissolve it in 120ml of 1,2-dichloroethane, cool down to 5-10°C, add 28g (0.21mol) of anhydrous Aluminum trichloride, stirring and adding 17.9g (0.11mol) octanoyl chloride dropwise, stirring for 4h after adding, treating the reaction solution with dilute hydrochloric acid, separating the organic solution, washing once with water, concentrating and recovering 1,2-dichloroethane, and The residue was recrystallized in 100ml of ethanol to obtain 33.1g of white crystals, yield 90.1%, melting range 74.3-75.2°C, 1 H-NMR data shows that the product obtained is 5-(4-octanoylphenylthio)indan-1-one; 1 H-NMR (CDCl 3 ), δ (ppm) value data: 0.8848 (t, 3H, CH 3 ), 1.2892-1.3412 (m, 8H, 4CH 2 ), 1.7359 (m,2H,CH 2 ), 2.7066 (t,2H,c-CH 2 ), 2.9526(t,2H,CH 2 ), 3.0961 (t,2H,c-CH 2 ), 7.2740 / 7.3008(d,1H,ArH), 7.3734(s,1H,ArH),...

Embodiment 3

[0134] Example 3 Synthesis of 5-(4-octanoylphenylthio)indan-1,2-dione-2-oxime

[0135]

[0136] Get 18.4g (0.05mol) of the product 5-(4-octanoylphenylthio)indan-1-one obtained in Example 2, dissolve it in a 250ml three-necked flask with 150ml ethanol, add 2g of 36% concentrated hydrochloric acid, and bathe in a water bath for 15 Stir at -20°C, add 6.2g (0.06mol) n-butyl nitrite dropwise within 15min, stir at 25°C for 5h, then cool down the reaction solution to 5-10°C, filter the precipitated yellow solid, 18.7g after drying, analyze the purity 98.90%, melting range 162.7-164.0°C, 1 H-NMR data showed that the obtained product was 5-(4-octanoylphenylthio)indan-1,2-dione-2-oxime, and the yield was 94.2%; 1 H-NMR (CDCl 3 ), δ (ppm) value data: 0.8866 (t, 3H, CH 3 ), 1.2965-1.3512 (m, 8H, 4CH 2 ), 1.7493 (m,2H,CH 2 ), 2.9737(t,2H,CH 2 ), 3.7977 (s,2H,c-CH 2 ), 7.2674 / 7.2943(d,1H,ArH), 7.3320(s,1H,ArH), 7.5281 / 7.5558(d,2H,2ArH), 7.7707 / 7.7977(d,1H,2ArH), 7.9648 / 7.9925(d, ...

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Abstract

The invention relates to an asymmetric dioxime ester compound shown as general formula I and a making method thereof. In the general formula I, Ar1 is X1 substituted C6-C20 o-arylene or C3-C20 o-heteroarylene; Ar2 is C6-C20 arylene or C3-C20 heteroarylene, is connected to Ar1 through X1, or at the same time of connection to Ar1 through X1, the Ar2 carbon atom adjacent to the substituent group X1 is in connection with Ar1 through an axial bond, carbon atom, carbonyl, O, S and NR18 to form a cyclic structure; n is 0 or 1; X1 is NR18, O, S, C=O or S=O; Y1 is (CH2)mCR15R16, NR19, O(CR15R16)m, S(CR15R16)m, (CR15R16)m C=O, S=O; m is 0 or 1; R1, R2 and R3 are respectively hydrogen atom, alkyl or alkoxy, arbitrary group substituted alkyl or alkoxy, cycloalkyl, arbitrary group substituted aryl, and acyl. The invention also relates to a photocurable composition with the general formula I compound as the photoinitiator. The composition is used for preparation of photoresist devices like color filters for display screens, and shows very high curing sensitivity. (formula I as shown in the specification).

Description

technical field [0001] The present invention relates to an asymmetric dioxime ester compound, which is characterized in that it is an esterified derivative in which arylene and cyclic ketoxime and chain ketoxime exist simultaneously in the molecule, and the esterified oxime group is at the carbonyl α-position, which has a Use as a photoinitiator in photocurable compositions. Background technique [0002] Oxime ester compounds have been discovered as photoinitiators very early. Both US3558309 and US4255513 patents have disclosed oxime ester compounds as photoinitiators. However, the oxime esters of some structures have poor thermal stability or low sensitivity, so it is difficult to Thermal stability, sensitivity and other properties meet the requirements of the modern electronics industry. CN1514845A discloses a series of oxime ester compounds, and two varieties OXE01 and OXE02 are on the market. Products with similar properties include oxime esters 305 and 304 disclosed in...

Claims

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Application Information

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IPC IPC(8): C07C323/47C07C319/20C07C251/66C07C249/12C07D307/83C07D333/78C07D307/77C07D209/94C07C251/44C07C323/22C07C49/84C08F2/48G03F7/004G03F7/027C09D11/101G02B5/20
CPCC07C49/84C07C249/12C07C251/44C07C251/66C07C319/20C07C323/22C07C323/47C07D209/94C07D307/83C08F2/48C09D11/101G02B5/20G03F7/004G03F7/027C07C323/45
Inventor 赵文超王永林王辰龙麻忠利姚丽秀胡伟静
Owner INSIGHT HIGH TECH (BEIJING) CO LTD
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