Compound, resin, material for forming underlayer film for lithography, underlayer film for lithography, pattern forming method, and purification method

Patent metadata

Field	Value
Publication number	US-10745372-B2
Application number	US-201515539560-A
Country	US
Kind code	B2
Filing date	Dec 14, 2015
Priority date	Dec 25, 2014
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

Abstract

A compound represented by the following formula (1):

wherein each X independently represents an oxygen atom or a sulfur atom, or non-crosslinking, R 1 represents a single bond or a 2n-valent group having 1 to 30 carbon atoms, the group may have an alicyclic hydrocarbon group, a double bond, a hetero atom, or an aryl group having 6 to 30 carbon atoms, each R 2 independently represents a straight, branched or cyclic alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or a hydroxyl group, in which at least one R 2 represents an alkoxy group having 1 to 30 carbon atoms or an aryloxy group having 6 to 30 carbon atoms, each m is independently an integer of 1 to 6, each p is independently 0 or 1, and n is an integer of 1 to 4.

First claim

The invention claimed is:

1. A material for forming an underlayer film for lithography comprising:
a compound represented by the following formula (1):

wherein each X is an oxygen atom, R 1 represents a 2n-valent group having 1 to 30 carbon atoms, the group may have an alicyclic hydrocarbon group, a double bond, a hetero atom, or an aryl group having 6 to 30 carbon atoms, each R 2 independently represents a straight, branched or cyclic alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or a hydroxyl group, in which at least one R 2 is selected from the group consisting of a butoxy group, a pentyloxy group, a hexyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cyclohexenyloxy group, an isophoronyloxy group, a norbornanyloxy group, an adamantyloxy group, a tricyclodecanyloxy group, a pyridinyloxy group, a phenyloxy group, a methylphenyloxy group, a dimethylphenyloxy group, a trimethylphenyloxy group, an ethylphenyloxy group, a propylphenyloxy group, a butylphenyloxy group, a cyclohexylphenyloxy group, a fluorophenyloxy group, a bromophenyloxy group, an iodophenyloxy group, a hydroxyphenyloxy group, a methoxyphenyloxy group, an aminophenyloxy group, a nitrophenyloxy group, a cyanophenyloxy group, a phenylphenyloxy group, a terphenyloxy group, a phenyloxyphenyloxy group, a naphthyloxy group, a methylnaphthyloxy group, a dimethylnaphthyloxy group, an ethylnaphthyloxy group, a fluoronaphthyloxy group, a chloronaphthyloxy group, a bromonaphthyloxy group, an iodonaphthyloxy group, a hydroxynaphthyloxy group, a methoxynaphthyloxy group, an aminonaphthyloxy group, a nitronaphthyloxy group, a cyanonaphthyloxy group, a phenylnaphthyloxy group, a phenyloxynaphthyloxy group, an anthracenyloxy group, a pyrenyloxy group, a methylpyrenyloxy group, a dimethylpyrenyloxy group and a fluorenyloxy group, each m is independently an integer of 1 to 6, each p is 1, and n is an integer of 1 to 4, the compound having a solubility of 5% by mass or more in cyclohexanone;
cyclohexanone as an organic solvent; and
at least one of an acid generating agent and a crosslinking agent.

2. The material for forming an underlayer film for lithography according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by the following formula (1A-2):

wherein R 1 and p are the same as those described in formula (1), R 6 is the same as R 2 defined in the formula (1), and each m 6 is independently an integer of 1 to 3.

3. The material for forming an underlayer film for lithography according to claim 1 , wherein the compound represented by formula (1) is represented by the following formula (BisN-1-CH1) or the following formula (BisN-1-CH2)

4. The material for forming an underlayer film for lithography according to claim 1 , wherein the compound represented by formula (1) is represented by the following formula (BisN-1-PH1) or the following formula (BisN-1-PH2)

5. The material for forming the underlayer film for lithography according to claim 1 comprising the acid generating agent.

6. The material for forming the underlayer film for lithography according to claim 1 comprising the crosslinking agent.

7. The material for forming an underlayer film for lithography according to claim 1 , wherein (i) a content of the organic solvent is 100 to 10,000 parts by mass based on 100 parts by mass of the compound, (ii) when the material for forming the underlayer film for lithography comprises the acid generating agent, a content of the acid generating agent is 0.1 to 50 parts by mass based on 100 parts by mass of the compound, and (iii) when the material for forming the underlayer film for lithography comprises the crosslinking agent, a content of the crosslinking agent is 5 to 50 parts by mass based on 100 parts by mass of the compound.

8. The material for forming an underlayer film for lithography according to claim 1 , wherein the crosslinking agent is at least one selected from the group consisting of aldehyde, ketone, carboxylic acid, carboxylic halide, a halogen-containing compound, an amino compound, an imino compound, isocyanate and an unsaturated hydrocarbon group-containing compound.

9. An underlayer film for lithography, formed from the material for forming the underlayer film for lithography according to claim 1 .

10. A resist pattern forming method, comprising
step (A-1) of forming an underlayer film on a substrate by using the material for forming the underlayer film for lithography according to claim 1 ,
step (A-2) of forming at least one photoresist layer on the underlayer film, and
step (A-3) of, after step (A-2), irradiating a predetermined region of the photoresist layer with radiation, followed by developing.

11. A circuit pattern forming method, comprising
step (B-1) of forming an underlayer film on a substrate by using the material for forming the underlayer film for lithography according to claim 1 ,
step (B-2) of forming an intermediate layer film on the underlayer film by using a silicon atom-containing resist intermediate layer film material,
step (B-3) of forming at least one photoresist layer on the intermediate layer film,
step (B-4) of, after step (B-3), irradiating a predetermined region of the photoresist layer with radiation, followed by developing to form a resist pattern, and
step (B-5) of, after step (B-4), etching the intermediate layer film with the resist pattern as a mask, etching the underlayer film with the obtained intermediate layer film pattern as an etching mask and etching the substrate with the obtained underlayer film pattern as an etching mask, to form a pattern on the substrate.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Toida Takumi
• Echigo Masatoshi
• Sato Takashi
• Makinoshima Takashi

Classifications

• C08G18/30

  Low-molecular-weight compounds {(C08G18/2805 takes precedence)} · CPC title

• G03F7/26

  Processing photosensitive materials; Apparatus therefor (G03F7/12 - G03F7/24 take precedence) · CPC title

• C08G8/04

  of aldehydes · CPC title

• C07D311/78 Primary

  Ring systems having three or more relevant rings · CPC title

• G03F7/11

  having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)} · CPC title