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High-efficiency polymerizable photoinitiator for photoresistance

A photoinitiator and polymerization type technology, applied in the field of photoinitiator for polymerizable color photoresist and its preparation, can solve the problems of easy yellowing, low solubility, large amount of photoinitiator, etc. The effects of migration, increased crosslink density, and increased initiation efficiency

Pending Publication Date: 2020-03-27
BEIJING ETERNAL MATERIAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although there are many types of photoinitiators, subject to the production and application process requirements of color gel, they must meet the requirements of heat resistance, acid resistance, alkali resistance, light resistance, unaffected color gel color and color gel chroma, etc. Therefore, there are fewer options
The existing photoinitiators for color glue mostly use solid small molecule photoinitiators, which often have poor compatibility with colorants, resins, monomers, etc., color, easy yellowing, easy aggregation, easy precipitation, low solubility, and poor thermal stability. , Easy to migrate or precipitate from the color plastic after light curing, which affects the quality of the color plastic; moreover, it is easy to volatilize and sublimate during the post-baking process, which affects the health of workers on the production line, and may damage the mask during the exposure process. pattern pollution
However, if a macromolecular photoinitiator is used directly, there are disadvantages such as low sensitivity, large amount of photoinitiator, and low conversion rate of double bonds of color glue.
In addition, hydrogen abstraction-type photoinitiators require co-initiators to achieve high initiation efficiency, which exacerbates the impact of the above problems

Method used

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  • High-efficiency polymerizable photoinitiator for photoresistance
  • High-efficiency polymerizable photoinitiator for photoresistance
  • High-efficiency polymerizable photoinitiator for photoresistance

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1. 4-methoxy,4'-(2-methacrylate)benzophenone E-1 Synthesis

[0047]

[0048] Add 48g of methanol (1.5mol) into a 250mL three-necked flask and stir, raise the temperature to reflux, slowly add 42g of diketene (0.5mol), continue to react at reflux temperature for 5h, and distill under reduced pressure to obtain 89.4g (0.77mol) of methyl acetoacetate .

[0049] Add 200mL THF and 15.6g stirred and dispersed NaH (60%, dispersed in mineral oil, 0.39mol) to a 500mL three-necked flask protected by argon, and 34.8g methyl acetoacetate (0.3mol) is added dropwise at room temperature in the flask and stir well. When the liquid in the flask became clear, 46.8 g of iodomethane (0.33 mmol) was added dropwise, the mixture was stirred at 40° C. for 10 h, the reaction solution was quenched with saturated aqueous ammonium chloride and extracted 3 times with ethyl acetate. The combined organic layers were dried with anhydrous sodium sulfate and spin-dried to dry the solvent,...

Embodiment 2

[0066] Example 2. 4-tert-butoxy,4'-(2-ethylacrylate)benzophenone E-2 Synthesis

[0067]

[0068] The synthesis process of E-2 refers to the synthesis of E-1, the difference is that the methanol used in A-1 is replaced by ethanol, and the anisole used in C-1 is replaced by tert-butylphenyl ether.

[0069] Wherein: tert-butylphenyl ether: purity 98%, purchased from Alfa Aesar.

[0070] NMR data of E-2: 1 H NMR (300Hz) in DMSO: δ1.07ppm (t, 3H), 1.42ppm (s, 9H), 4.00ppm (q, 2H), 6.20, 6.39ppm (d, J = 56.7, 2H), 7.03-7.73 ppm(m,8H).

Embodiment 3

[0071] Example 3. 4-(N,N-Dimethylamino),4’-(2-Acrylic acid methyl) benzophenone E-3 Synthesis

[0072]

[0073]Under nitrogen protection, add 7.2g of magnesium chips (0.3mol) and a grain of iodine to a 500mL three-necked flask, slowly introduce 100mL of THF solution and 20g of 4-bromo-N,N-dimethylaniline (0.1mol) into the flask . Control the Grignard reaction speed, and after the dripping is completed, heat in a water bath until THF refluxes. After 4 hours, the heating was removed, and after the temperature of the liquid in the flask dropped to room temperature, the solution in the flask was slowly introduced into a 1000 mL three-necked flask through a thin guide needle. Fully dissolve 20 g of 4-bromooxynil (1.1 mol) in 100 mL of THF solution, and slowly drop it into the three-neck flask. After the dripping was completed, the solution in the flask was heated to THF reflux, and the water bath was removed after the reaction was completed. After the solution in the flask d...

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Abstract

The invention provides a high-efficiency polymerizable photoinitiator suitable for color photoresist and a preparation method of the photoinitiator, the initiator takes hydrogen abstraction type photoinitiator benzophenone as a core, an acrylate group is introduced into one benzene ring, and a hydrogen donor group is introduced into the other benzene ring. On one hand, the acrylate group can improve the solubility of the photoinitiator and improve the compatibility with resin, monomers and the like, and on the other hand, the photoinitiator participates in polymerization in the photocuring process, so that the crosslinking density of the colored glue is improved, the hardness is improved, and micromolecular photoinitiator migration caused by post-baking high temperature or extreme conditions is reduced; the hydrogen-donating group can significantly improve the initiation efficiency of the photoinitiator and the polymerization speed of the system.

Description

technical field [0001] The invention provides an organic compound and a preparation method thereof, in particular a series of photoinitiators for polymerizable color photoresists capable of participating in photocuring and a preparation method thereof. Background technique [0002] Color photoresist (hereinafter sometimes referred to as color glue) is a kind of photochemically active substance. Under ultraviolet light, the substance coated on the glass plate is rapidly cured and polymerized in a specific area, and finally a colored pattern is obtained through selective etching. Color glue is currently widely used in the production of flat panel display color filters (hereinafter sometimes referred to as photoresists). The photoinitiator is excited by ultraviolet light in the color gel to undergo chemical changes to produce active intermediates with the ability to initiate active polymerization. [0003] Although there are many types of photoinitiators, subject to the produ...

Claims

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Application Information

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IPC IPC(8): G03F7/004G03F7/027C08F2/48C07C69/738C07C67/343C07C227/10C07C229/44
CPCG03F7/004G03F7/027C08F2/48C07C69/738C07C229/44Y02P20/10
Inventor 桑伟刘永祥侯少堃王晓青孙涛
Owner BEIJING ETERNAL MATERIAL TECH
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