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Degradable photoresist resin monomer synthesized from dimethyl bicyclo [3.3.1] nonane diketone and synthesis method of degradable photoresist resin monomer

A technology of dimethyl bicyclic, resin monomer, applied in the field of resin monomer and its synthesis, can solve the problems of weak etching resistance, insufficient resolution, etc., achieve good etching resistance, increase solubility, dissolve The effect of increased speed difference

Pending Publication Date: 2020-09-01
XUZHOU B&C CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Resin is a polymer formed by the polymerization of various resin monomers. Among them, the acid-sensitive resin monomer is an important part to realize the difference in the dissolution of the resin in the developer solution before and after exposure. The common acid-sensitive resin monomer has only one acid-sensitive group. , the resin monomer is a linear polymer with weak etching resistance, and the poor solubility in the developer solution after exposure is only determined by the acid-sensitive resin monomer, resulting in insufficient resolution.

Method used

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  • Degradable photoresist resin monomer synthesized from dimethyl bicyclo [3.3.1] nonane diketone and synthesis method of degradable photoresist resin monomer
  • Degradable photoresist resin monomer synthesized from dimethyl bicyclo [3.3.1] nonane diketone and synthesis method of degradable photoresist resin monomer
  • Degradable photoresist resin monomer synthesized from dimethyl bicyclo [3.3.1] nonane diketone and synthesis method of degradable photoresist resin monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] The first step: a, preparation of methyl Grignard reagent: magnesium chips (2.7g, 111mmol) were added to anhydrous ether (15mL), then an iodine tablet was added, and methyl bromide (10.6g, 112mmol) Dissolve it in ether (25mL) to prepare a solution. Under the protection of nitrogen, first add methyl bromide in ether solution (6mL) to the above reaction solution. Add the remaining ether solution of methyl bromide dropwise, add ether (20mL), raise the temperature to keep boiling slightly, and reflux for half an hour; b. Synthesis of intermediate 1-2: under nitrogen protection, use the prepared methyl Grignard reagent with Cool in ice water, add (1R, 4R, 5S, 6S)-4,6-dimethylbicyclo[3.3.1]nonane-2,8-dione (10.0g, 55mmol) dropwise in diethyl ether ( 20mL) solution, control the rate of addition, keep the reaction solution slightly boiling, after the dropwise addition, continue to stir at 25 degrees Celsius for half an hour, white solids are precipitated in the reac...

Embodiment 2

[0030]

[0031] The first step: the operation steps and raw material dosage are the same as the first step reaction of Example 1, and the reaction obtains compound 2-2 (8.5g, 40mmol, 72.2%);

[0032] The second step: the operation steps are the same as the second step reaction of Example 1, wherein the reactants and the charging amount: intermediate 1-2 (8.8g, 41mmol) is replaced by intermediate 2-2 (8.5g, 40mmol), propylene Acyl chloride (7.6g, 84mmol) was replaced by methacryloyl chloride (8.4g, 80mmol), triethylamine (16.8g, 166mmol) was replaced by triethylamine (16.2g, 160mmol), and compound 2-3 (9.8g, 28 mmol, 70.2%).

Embodiment 3

[0034]

[0035] The first step: the operation steps are the same as the first step of Example 1, wherein methyl bromide (10.6g, 112mmol) is changed to ethyl bromide (12.1g, 111mmol), to obtain compound 3-2 (10.5g, 44mmol, 78.7 %);

[0036] The second step: the operation steps are the same as the second step reaction of Example 1, wherein reactants and charging amount: intermediate 1-2 (8.8g, 41mmol) is replaced by intermediate 3-2 (10.5g, 44mmol), propylene Acyl chloride (7.6g, 84mmol) was replaced by acryloyl chloride (8g, 88mmol), triethylamine (16.8g, 166mmol) was replaced by triethylamine (17.7g, 175mmol), and compound 3-3 (11g, 32mmol, 72.3% ).

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Abstract

The invention discloses a degradable photoresist resin monomer synthesized from dimethyl bicyclo [3.3. 1] nonane diketone and a synthesis method of the resin monomer. The structural formula of the resin monomer is shown in the specification, wherein R1 is a saturated alkane or a cycloalkane, and R2 is hydrogen or methyl. The synthesis method comprises the following steps: reacting (1R, 4R, 5S, 6S)-4, 6-dimethyl bicyclo [3.3. 1] nonane-2, 8-dione (I) with an alkyl Grignard reagent or a cycloalkyl Grignard reagent under the protection of inert gas to obtain an intermediate (II); reacting the intermediate (II) with acryloyl chloride or methacryloyl chloride under an alkaline condition to obtain a resin monomer (III); polymer resin formed by polymerizing the resin monomer provided by the invention and other resin monomers has better etching resistance, is beneficial to improving the edge roughness of a developed pattern, and greatly improves the resolution of a photoetching pattern.

Description

technical field [0001] The invention relates to the field of photoresist resin, in particular to a resin monomer and a synthesis method thereof. Background technique [0002] Photolithography technology refers to the chemical sensitivity of photoresist materials (especially photoresist) under the action of visible light, ultraviolet rays, electron beams, etc., through exposure, development, etching and other processes, the design on the mask plate Graphics microfabrication technology that transfers graphics to the substrate. [0003] Photolithography 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. , This type of material is chemically sensitive to light (including visible light, ultraviolet rays, electron beams, etc.), and its solubility in the developer solution changes thro...

Claims

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Application Information

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IPC IPC(8): C07C69/54C07C67/08G03F7/004
CPCC07C69/54G03F7/004C07C2602/46C07C2601/14
Inventor 傅志伟贺宝元邵严亮毛国平余文清薛富奎刘司飞
Owner XUZHOU B&C CHEM CO LTD
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