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Compound, resin, material for forming underlayer film for lithography, underlayer film for lithography, pattern forming method, and method for purifying compound or resin

A compound and lower-layer technology, applied in the preparation of organic compounds, chemical instruments and methods, and photosensitive materials for optomechanical equipment, etc., can solve the problems of difficult to obtain resist pattern film thickness, resist pattern collapse, resolution, etc. question

Inactive Publication Date: 2018-01-02
MITSUBISHI GAS CHEM CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as the resist pattern is miniaturized, problems such as resolution problems and resist pattern collapse after development gradually occur, so resist thinning is desired.
In response to such expectations, it is difficult to obtain a resist pattern film thickness sufficient for substrate processing only by reducing the thickness of the resist

Method used

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  • Compound, resin, material for forming underlayer film for lithography, underlayer film for lithography, pattern forming method, and method for purifying compound or resin
  • Compound, resin, material for forming underlayer film for lithography, underlayer film for lithography, pattern forming method, and method for purifying compound or resin
  • Compound, resin, material for forming underlayer film for lithography, underlayer film for lithography, pattern forming method, and method for purifying compound or resin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0310] (Example 1) Synthesis of TriF-3

[0311] Prepare a container with an internal volume of 1000 mL including a stirrer, condenser, and burette. In this container, 100 g (537 mmol) of 4,4-biphenol (reagent manufactured by Tokyo Chemical Industry Co., Ltd.), 49 g (269 mmol) of 4-biphenylaldehyde (manufactured by Mitsubishi Gas Chemical Co., Ltd.) and 400 mL of butyl acetate were added, and concentrated sulfuric acid (96 Mass %, 27 g (269 mmol) of reagent manufactured by Kanto Chemical Co., Ltd., to prepare a reaction liquid. This reaction liquid was stirred at 130°C for 5 hours to perform the reaction. Then, 2 L of ion-exchange water was added to the reaction liquid to precipitate the reaction product, and it was cooled to room temperature. Then, 89 g (534 mmol) of sodium hydroxide aqueous solution (24% by mass) was added, neutralized, and separated by filtration. After drying the solid obtained by filtration, it was dissolved in 400 mL of ethyl acetate, and 400 mL of heptan...

Embodiment 2

[0322] (Example 2) Synthesis of TriF-2

[0323] 100 g of (TriF-3) synthesized in Example 1 was separated by column chromatography to obtain 11.3 g of the target compound group (TriF-2) represented by the following formula.

[0324] It should be noted that through 400MHz- 1 H-NMR found the following peaks.

[0325] 1 H-NMR: (d-DMSO, internal standard TMS)

[0326] δ(ppm) 9.3~9.4(6.1H, O-H), 6.7~7.7(38.8H, Ph-H), 6.0~6.2(2.1H, C-H)

[0327] In addition, the peaks shown in Table 2 and the corresponding molecular weights were observed in LC-MS.

[0328] [Table 2]

[0329] Hold time (minutes)

Molecular weight (m / z)

area(%)

4.79

886.3

94.5

6.36

1236.5

5.5

[0330] From the above 1 The results of H-NMR and LC-MS confirmed that the target compound group obtained in Example 2 is a mixture having a chemical structure of the following formula.

[0331]

[0332] n=1 (94.5%), n=2 (5.5%)

[0333] (TriF-2)

Embodiment 3

[0334] (Example 3) Synthesis of TriF-1

[0335] 10 g of (TriF-2) synthesized in Example 2 was separated by column chromatography to obtain 8.4 g of the target compound (TriF-1) represented by the following formula.

[0336] It should be noted that through 400MHz- 1 H-NMR found the following peaks.

[0337] 1 H-NMR: (d-DMSO, internal standard TMS)

[0338] δ(ppm) 9.3(6H, O-H), 6.7~7.7(38H, Ph-H), 6.0~6.1(2H, C-H)

[0339] In addition, the peaks shown in Table 3 and the corresponding molecular weights were observed in LC-MS.

[0340] [table 3]

[0341] Hold time (minutes)

Molecular weight (m / z)

area(%)

4.79

886.3

>99.8

[0342] From the above 1 The results of H-NMR and LC-MS confirmed that the target compound obtained in Example 3 is a compound having a chemical structure of the following formula.

[0343]

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PUM

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Abstract

This compound is represented by formula (1). (In formula (1), R1's are each independently a divalent group having 1-30 carbon atoms, R2 to R7 are each independently a linear, branched, or cyclic alkylgroup having 1-10 carbon atoms, an aryl group having 6-10 carbon atoms, an alkenyl group having 2-10 carbon atoms, a thiol group or a hydroxyl group, wherein at least one R5 is a hydroxyl group or athiol group, m2, m3, and m6 are each independently an integer of 0-9, m4 and m7 are each independently an integer of 0-8, m5 is an integer of 1-9, n is an integer of 1-4, and p2 to p7 are each independently an integer of 0-2.)

Description

Technical field [0001] The present invention relates to a compound or resin having a specific structure. In addition, the present invention relates to an underlayer film forming material for lithography containing the compound or resin, an underlayer film for lithography obtained from the material, and a pattern forming method using the material. Furthermore, the present invention relates to a purification method of the compound or resin. Background technique [0002] In the manufacture of semiconductor devices, photoresist materials are used for microfabrication of photolithography. However, in recent years, with the high integration and high speed of LSI, further miniaturization is required based on pattern rules. In the lithography using light exposure used as a current general technology, the substantial resolution limit derived from the wavelength of the light source is gradually approaching. [0003] The light source for photolithography used when forming the resist pattern...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/15C07C37/20C07C37/72C08G8/04C08G8/20G03F7/11
CPCC07C39/15C08G8/04G03F7/094G03F7/0397C09D161/12G03F7/11G03F7/2012C08G8/20H01L21/0274C07C37/72C07C37/20C08G8/02H01L21/3081
Inventor 堀内淳矢越后雅敏牧野嶋高史
Owner MITSUBISHI GAS CHEM CO INC