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

Patent metadata

Field	Value
Publication number	US-10294183-B2
Application number	US-201515125503-A
Country	US
Kind code	B2
Filing date	Mar 13, 2015
Priority date	Mar 13, 2014
Publication date	May 21, 2019
Grant date	May 21, 2019

Abstract

The compound according to the present invention is represented by a specific formula. The compound according to the present invention has a structure according to the specific formula, and therefore can be applied to a wet process and is excellent in heat resistance and etching resistance. In addition, the compound according to the present invention has such a specific structure, and therefore has a high heat resistance, a relatively high carbon concentration, a relatively low oxygen concentration and also a high solvent solubility. Therefore, the compound according to the present invention can be used to form an underlayer film whose degradation is suppressed at high-temperature baking and which is also excellent in etching resistance to oxygen plasma etching or the like. Furthermore, the compound is also excellent in adhesiveness with a resist layer and therefore can form an excellent resist pattern.

First claim

The invention claimed is:

1. A compound represented by the following formula (1):

wherein R 1 includes 1-30 carbon atoms and is a group represented by R A -R B where R A is a methine group and R B is an aryl group having 7 or more carbon atoms, each of R 2 to R 5 is independently a linear, 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, a thiol group or a hydroxyl group, wherein at least one R 4 and/or at least one R 5 is a hydroxyl group and/or a thiol group, each of m 2 and m 3 is independently an integer of 0 to 8, each of m 4 and m 5 is independently an integer of 0 to 9, wherein at least one of m 4 and m 5 is an integer of 1 to 9, n is an integer of 1, and each of p 2 to p 5 is independently an integer of 0 to 2.

2. The compound according to claim 1 , wherein at least one R 2 and/or at least one R 3 is a hydroxyl group and/or a thiol group.

3. The compound according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by the following formula (1a):

wherein R 1 to R 5 and n are the same as defined in the formula (1), each of m 2′ and m 3′ is independently an integer of 0 to 4, and each of m 4′ and m 5′ is independently an integer of 0 to 5, wherein at least one of m 4′ and m 5′ is an integer of 1 to 5.

4. The compound according to claim 3 , wherein the compound represented by the formula (1a) is a compound represented by the following formula (1b):

wherein R 1 is the same as defined in the formula (1), each of R 6 and R 7 is independently a linear, 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, a thiol group or a hydroxyl group, and each of m 6 and m 7 is independently an integer of 0 to 7.

5. The compound according to claim 4 , wherein the compound represented by the formula (1b) is represented by the following formula (BiF-1)

6. A resin obtained by using the compound according to claim 1 as a monomer.

7. A material for forming an underlayer film for lithography, comprising the compound according to claim 1 .

8. The material for forming the underlayer film for lithography according to claim 7 , further comprising an organic solvent.

9. The material for forming the underlayer film for lithography according to claim 7 , further comprising an acid generator.

10. The material for forming the underlayer film for lithography according to claim 7 , further comprising a crosslinking agent.

11. An underlayer film for lithography, formed from the material for forming the underlayer film for lithography according to claim 7 .

12. 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 according to claim 7 ,
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 with an alkali.

13. 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 according to claim 7 ,
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 with an alkali 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 an obtained intermediate layer film pattern as an etching mask and etching the substrate with an obtained underlayer film pattern as an etching mask, to form a pattern on the substrate.

14. A method for purifying the compound according to claim 1 , the method comprising
a step of bringing a solution comprising an organic solvent optionally immiscible with water, and the compound into contact with an acidic aqueous solution for extraction.

15. The method according to claim 14 , wherein the acidic aqueous solution is an aqueous solution of at least one mineral acid selected from the group consisting of hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid, or an aqueous solution of at least one organic acid selected from the group consisting of acetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, fumaric acid, maleic acid, tartaric acid, citric acid, methanesulfonic acid, phenolsulfonic acid, p-toluenesulfonic acid and trifluoroacetic acid.

16. The method according to claim 14 , wherein the organic solvent optionally immiscible with water is toluene, 2-heptanone, cyclohexanone, cyclopentanone, methyl isobutyl ketone, propylene glycol monomethyl ether acetate or ethyl acetate.

17. The method according to claim 14 , further comprising a step of performing an extraction treatment with water, after the step of bringing the solution into contact with the acidic aqueous solution for extraction.

18. A resin having, as a repeating structure, the following structure represented by formula (2):

wherein R 1 is a 2n-valent group having 1 to 30 carbon atoms, each of R 2 to R 5 is independently a linear, 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, a thiol group or a hydroxyl group, wherein at least one R 4 and/or at least one R 5 is a hydroxyl group and/or a thiol group, L is a single bond, or a linear or branched alkylene group having 1 to 20 carbon atoms, each of m 2 and m 3 is independently an integer of 0 to 8, each of m 4 and m 5 is independently an integer of 0 to 9, wherein at least one of m 4 and m 5 is an integer of 1 to 9, n is an integer of 1 to 4, and each of p 2 to p 5 is independently an integer of 0 to 2.

19. A material for forming an underlayer film for lithography, comprising the resin according to claim 18 .

20. The material for forming the underlayer film for lithography according to claim 19 , further comprising an organic solvent.

21. The material for forming the underlayer film for lithography according to claim 19 , further comprising an acid generator.

22. The material for forming the underlayer film for lithography according to claim 19 , further comprising a crosslinking agent.

23. An underlayer film for lithography, formed from the material for forming the underlayer film for lithography according to claim 19 .

24. A resist pattern forming method, comprising
step (A-1) of forming an underlayer film on a substrate by using the material fo

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Makinoshima Takashi
• Echigo Masatoshi

Classifications

• C08G8/04

  of aldehydes · CPC title

• G03F7/11

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

• C09D161/12

  with polyhydric phenols · CPC title

• G03F7/094

  Multilayer resist systems, e.g. planarising layers · CPC title

• C07C39/15 Primary

  with all hydroxy groups on non-condensed rings {, e.g. phenylphenol} · CPC title