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Degradable resin monomer synthesized from dicyclohexylketone and preparation method of degradable resin monomer

A technology of dicyclohexyl ketone and resin monomers, which is applied in the field of degradable resin monomers and its preparation, can solve the problem of low resolution of photolithography patterns, and achieve the effect of simple synthesis route and convenient operation

Pending Publication Date: 2021-04-02
上海博栋化学科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, due to the specific structure of the acid-sensitive resin monomer in the existing photoresist, there is a problem of low photolithographic pattern resolution

Method used

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  • Degradable resin monomer synthesized from dicyclohexylketone and preparation method of degradable resin monomer
  • Degradable resin monomer synthesized from dicyclohexylketone and preparation method of degradable resin monomer
  • Degradable resin monomer synthesized from dicyclohexylketone and preparation method of degradable resin monomer

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] Preparation of compound 1-2:

[0029] Dissolve tert-butyldimethylsilyl chloride (13g, 86.3mmol) in tetrahydrofuran (50g), and then add the above mixture dropwise to 2-bromoethanol 1-1 (10g, 80.0 mmol), triethylamine (10g, 98.8mmol) and 4-dimethylaminopyridine (1g, 8.2mmol) in tetrahydrofuran (100g) solution, stirred for 3 hours. The resulting suspension was filtered to obtain a filtrate, which was concentrated and purified by vacuum distillation to obtain compound 1-2 (15.5 g, 64.8 mmol, molar yield 81.0%).

[0030] Preparation of Compound 1-3:

[0031] Compound 1-2 (13g, 54.3mmol) was dissolved in ether (100g), and under nitrogen protection, the above mixture was added dropwise to ether (30g) containing magnesium (1.3g, 54.2mmol), at 25°C Next, stir for 1 hour. Then dicyclohexyl ketone (10 g, 51.5 mmol) was dissolved in ether (80 g), dropped into the above mixture, and stirred for 3 hours. The reaction solution was quenched, then filtered, and the filtr...

Embodiment 2

[0037]

[0038] Preparation of compound 2-2:

[0039] Dissolve tert-butyldimethylsilyl chloride (10g, 66.3mmol) in tetrahydrofuran (50g), and then add the above mixture dropwise to 3-bromomethyl-3-hydroxymethyl -1-oxetane 1-1 (10g, 55.2mmol), triethylamine (8g, 79.1mmol) and 4-dimethylaminopyridine (1g, 8.2mmol) in tetrahydrofuran (100g) solution, stirring 3 hours. The resulting suspension was filtered to obtain a filtrate, which was concentrated and purified by vacuum distillation to obtain compound 2-2 (13 g, 44.0 mmol, molar yield 79.7%).

[0040] Preparation of compound 2-3:

[0041] Compound 2-2 (13g, 44.0mmol) was dissolved in ether (100g), and under nitrogen protection, the above mixture was added dropwise to ether (30g) containing magnesium (1.2g, 50mmol), at 25°C , and stirred for 1 hour. Then dicyclohexyl ketone (8 g, 41.2 mmol) was dissolved in ether (80 g), dropped into the above mixture, and stirred for 3 hours. The reaction solution was quenched, then fil...

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Abstract

The invention belongs to a degradable photoresist resin monomer, and discloses a degradable resin monomer synthesized from dicyclohexylketone and a preparation method of the degradable resin monomer.The structural formula of the resin monomer is shown in the description, wherein R is alkyl or heteroalkyl. The preparation method comprises the steps of protecting hydroxyl of a raw material I to obtain an intermediate II, wherein the raw material I comprises a structural general formula shown in the description, and R which is alkyl or heteroalkyl; reducing dicyclohexyl ketone under the condition of a Grignard reagent formed by the intermediate II and metal to obtain an intermediate III containing a hydroxyl group; deprotecting the intermediate III to obtain an intermediate IV containing twohydroxyl groups; and carrying out esterification reaction on the intermediate IV and an acrylic compound to obtain a resin monomer V. The resin monomer disclosed by the invention comprises a tert-butyl structure and a cyclic polyester structure, can improve the edge roughness, increase the contrast ratio and improve the resolution ratio, and has excellent etching resistance and fat solubility, and the preparation method is simple and convenient.

Description

technical field [0001] The invention relates to the technical field of degradable photoresist resin monomers, in particular to a degradable resin monomer synthesized from dicyclohexyl ketone and a preparation method thereof. Background technique [0002] Photolithographic materials (especially photoresist), also known as photoresist, are the most critical functional chemical materials involved in photolithography technology. The main components are resin, photoacid generator, and corresponding additives and Solvents, such materials are chemically sensitive to light (including visible light, ultraviolet rays, electron beams, etc.), and their solubility in the developer solution changes through photochemical reactions. [0003] The resin used in the photoresist is a polymer formed by the copolymerization of various resin monomers. Among them, the acid-sensitive resin monomer is an important part of realizing the difference in the dissolution of the resin in the developer solut...

Claims

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Application Information

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IPC IPC(8): C07C69/54C07D305/06C07C67/14C07C29/09C07C31/27C07F7/18
CPCC07C69/54C07D305/06C07C67/14C07C29/09C07F7/1804C07F7/188C07F7/1892C07C2601/14Y02P20/55
Inventor 傅志伟潘惠英蒋小惠毕景峰李嫚嫚
Owner 上海博栋化学科技有限公司
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