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Monomer having lactone skeleton, polymer compound and photoresist composition

A polymer compound and skeleton technology, applied in the field of photoresist monomers, polymer compounds and photoresist compositions, can solve problems such as poor solubility, achieve improved solubility, excellent solubility, The effect of sharp patterns

Inactive Publication Date: 2011-05-18
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, resins containing a large amount of cycloaliphatic acrylic esters having lactone rings have poor solubility in organic solvents such as resist solvents, and therefore there is an urgent need to improve the solubility of resins used in resists.

Method used

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  • Monomer having lactone skeleton, polymer compound and photoresist composition
  • Monomer having lactone skeleton, polymer compound and photoresist composition
  • Monomer having lactone skeleton, polymer compound and photoresist composition

Examples

Experimental program
Comparison scheme
Effect test

manufacture example 1

[0117] 2-Methacryloyloxyacetoxy-3,3-dimethyl-γ-butyrolactone was produced according to the following reaction procedure formula.

[0118] [chemical formula 9]

[0119]

[0120] Add 10.0 g (0.0768 mol) of 2-hydroxy-3,3-dimethyl-γ-butyrolactone represented by formula (5a) and 20.0 g of acetonitrile in the three-necked flask and dissolve it, then add 1,8-di Azabicyclo[5.4.0]undec-7-ene (DBU) 38.6g (0.2536mol), and the internal temperature was raised to 30°C. After that, 26.0 g (0.2305 mol) of chloroacetyl chloride represented by the formula (4a) was slowly added dropwise at an internal temperature of 45° C. or lower in a nitrogen atmosphere, and then stirred at 40° C. for 5 hours. Then, after adding and stirring the reaction liquid to the liquid mixture of 50 g of ethyl acetate and 50 g of pure water, it liquid-separated and extracted the organic layer. After the extracted organic layer was washed 3 times with 36 g of 8% by weight aqueous sodium bicarbonate solution, 2 times...

Embodiment 2

[0127] Synthesis of polymer compounds with the following structures

[0128] [chemical formula 10]

[0129]

[0130] In a round-bottomed flask equipped with a reflux tube, a stirring bar, and a three-way cock, under a nitrogen atmosphere, add 41.65 g of propylene glycol monomethyl ether acetate (PGMEA) and 17.85 g of propylene glycol monomethyl ether (PGME), and keep the temperature While stirring at 80°C, the following monomer solution consisting of 2-methacryloyloxyacetoxy-3,3-dimethyl- γ-butyrolactone 12.07g (47.1mmol), 1-hydroxy-3-methacryloyloxyadamantane 5.57g (23.5mmol), 1-(1-methacryloyloxy-1-methyl ethyl Base) 12.36 g (47.1 mmol) of adamantane, 1.80 g of dimethyl 2,2'-azobisisobutyrate [manufactured by Wako Pure Chemical Industries, Ltd., trade name "V-601"], 77.35 g of PGMEA And PGME 33.15g mixed. After the dropwise addition was completed, stirring was continued for 2 hours. After the polymerization reaction finished, this reaction solution was added dropwise ...

Embodiment 3

[0132] Synthesis of polymer compounds with the following structures

[0133] [chemical formula 11]

[0134]

[0135] Except that the monomer components used in Example 2 were changed to the following components, the same operation as in Example 2 was carried out to obtain 25.2 g of the target resin. The monomer components are: 2-methacryloyloxy Acetoxy-3,3-dimethyl-γ-butyrolactone 12.63g (49.3mmol), 1-hydroxy-3-methacryloyloxyadamantane 5.82g (24.6mmol), 2-methylpropene 11.55 g (49.3 mmol) of acyloxy-2-methyladamantane. GPC analysis was carried out on the recovered polymer, and the results showed that its Mw (weight average molecular weight) was 8900, and its molecular weight distribution (Mw / Mn) was 1.89.

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Abstract

Disclosed is a novel monomer having a lactone skeleton, which is useful as a monomer component for a highly functional polymer or the like that can maintain stability such as chemical resistance when used for a resist resin or the like, while having excellent solubility in organic solvents and improved hydrolyzability and / or improved solubility in water after hydrolysis. The monomer having a lactone skeleton is represented by formula (1) (wherein Ra represents a hydrogen atom, a halogen atom or an optionally substituted alkyl group having 1-6 carbon atoms; R1 represents a group having a lactone skeleton; and Y represents a divalent organic group having 1-6 carbon atoms).

Description

technical field [0001] The present invention relates to a photoresist monomer, a polymer compound, and a photoresist composition used in microfabrication of semiconductors, and a method for producing a semiconductor using the photoresist composition. Background technique [0002] In the field of semiconductor manufacturing, photolithography technology for patterning has been rapidly developed, and along with this development, the line width has also tended to be extremely finer in recent years. Initially, i-rays and g-rays were used for exposure in lithography, and their line widths were also wide. Therefore, the capacity of the fabricated semiconductor is also low. However, with the development of technology in recent years, the use of KrF excimer laser has become possible, and its line width has also rapidly become smaller. Since then, research has progressed towards the application of ArF excimer lasers with shorter wavelengths, and in recent years they have been put in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F20/28C07D307/33G03F7/039H01L21/027
CPCC07D307/33C08F220/18G03F7/0397C08F220/28C08F220/1818C08F220/283C08F20/28H01L21/0275
Inventor 小山裕住田真理田中洋己
Owner DAICEL CHEM IND LTD
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