METHOD OF PRODUCING LAYER STRUCTURE, AND METHOD OF FORMING PATTERNS

• US 20170115572A1
• Filed: 09/14/2016
• Published: 04/27/2017
• Est. Priority Date: 10/23/2015
• Status: Active Grant

• Current Assignee: Samsung SDI Company Limited
• Original Assignee: Samsung SDI Company Limited
• Inventors: KIM, Sunghwan, KIM, Yoona, KIM, Jinhyung, LEE, Chungheon, JEONG, Seulgi, KIM, Minsoo, SONG, Hyunji, KANG, Sunhae, KIM, Youngmin, NAM, Younhee, BAEK, Jaeyeol, YOON, Byeri, HONG, Seunghee, HWANG, Sunmin
• Granted Patent: US 10,663,863 B2
• Time in Patent Office: Days
• CPC Class Codes: G03F 7/091 characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
• CPC Class Codes: G03F 7/11 having cover layers or intermediate layers, e.g. subbing layers G03F7/091 - G03F7/093, B41N3/03 take precedence

Abstract

A method of producing a layer structure and a method of forming a pattern, the method of producing a layer structure including coating a first composition on a substrate that has a pattern thereon; curing the coated first composition to form a first organic layer; applying a liquid material to the first organic layer to remove a part of the first organic layer; and coating a second composition on remaining parts of the first organic layer; and curing the coated second composition on the remaining parts of the first organic layer to form a second organic layer: wherein the first composition and the second composition each independently include a solvent, and a polymer including a structural unit represented by Chemical Formula 1,

*A¹-B¹*.  [Chemical Formula 1]

Claims

1. A method of producing a layer structure, the method comprising

coating a first composition on a substrate that has a pattern thereon;

curing the coated first composition to form a first organic layer;

applying a liquid material to the first organic layer to remove a part of the first organic layer; and

coating a second composition on remaining parts of the first organic layer; and

curing the coated second composition on the remaining parts of the first organic layer to form a second organic layer;

wherein the first composition and the second composition each independently include;

a solvent, and

a polymer including a structural unit represented by Chemical Formula 1,

*

A¹-B¹

*[Chemical Formula 1]

wherein, in Chemical Formula 1,

A¹ is a divalent cyclic group including at least one of a substituted or unsubstituted benzene ring,

B¹ is a divalent organic group, and

* is a linking point.

2. The method as claimed in claim 1, wherein the remaining parts of the first organic layer remain inside gaps of the pattern.

3. The method as claimed in claim 1, wherein the liquid material includes γ

-butyrolactone, δ

-valerolactone, ethyllactate, ethyl-3-ethoxypropionate, propylene glycolmonomethyl ether acetate, β

-hydroxy β

-methylbutyrate, methanol, ethanol, 1-propyl alcohol, 2-propyl alcohol, 2-butanol, ethylene glycol, propylene glycol, glycerol, 1,6-hexanediol, cyclo hexanediol, sorbitol, xylitol, 2-methyl-2,4-pentanediol, 1,3-butanediol, 1,4-butanediol, ethylene glycol monomethyl ether, diethylene glycol, dipropylene glycol, propylene glycol monomethyl ether, diethylene glycol monomethyl ether, triethylene glycol, poly(ethylene glycol), propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, ethylethoxy propionate, propylene glycol monomethyl ether propionate, ethylene glycol diacetate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, n-butyl acetate, formamide, monomethylformamide, dimethyl formamide, acetamide, monomethylacetamide, dimethyl acetamide, monoethylacetamide, diethylacetamide, N-methylpyrrolidone, methoxy methyl propionate, methoxy ethyl propionate, methoxy propyl propionate, methoxy butyl propionate, ethoxy methyl propionate, ethoxy ethylpropionate, ethoxy propyl propionate, ethoxy butyl propionate, dimethyl sulfone, dimethyl sulfoxide, sulfolane, acetone, acetyl acetone, methylethyl ketone, methyl isobutyl ketone, or a combination thereof.

4. The method as claimed in claim 1, wherein the liquid material is applied in an amount of about 0.1 cc to about 100 cc.

5. The method as claimed in claim 1, wherein the first organic layer and the second organic layer are a hardmask layer.

6. The method as claimed in claim 5, wherein the second organic layer is directly on the remaining parts of the first organic layer.

7. The method as claimed in claim 1, wherein, in Chemical Formula 1, A¹ is a divalent cyclic group including at least two rings in its structure.

8. The method as claimed in claim 1, wherein, in Chemical Formula 1, A¹ is a substituted or unsubstituted divalent cyclic group of one of the following compounds:

9. The method as claimed in claim 1, wherein, in Chemical Formula 1, A¹ is a group that is substituted with a hydroxy group, a thionyl group, a thiol group, a cyano group, an amino group, a C1 to C10 alkyl group, a C6 to C30 aryl group, a C1 to C30 alkoxy group, or a combination thereof.

10. The method as claimed in claim 1, wherein the polymer further includes a structural unit represented by Chemical Formula 2:

*

A²-B¹

* 

 

[Chemical Formula 2]

wherein, in Chemical Formula 2,

A² is a divalent cyclic group including at least one of a substituted or unsubstituted benzene ring, and

B¹ and * are defined the same as those of Chemical Formula 1, and

wherein the structural unit represented by Chemical Formula 2 is different from the structural unit represented by Chemical Formula 1.

11. The method as claimed in claim 1, wherein, in Chemical Formula 1, B¹ is represented by Chemical Formula 3:

*-

C^H2

^aL

C^H2

^b-* 

 

[Chemical Formula 3]

wherein, in Chemical Formula 3,

a and b are each independently an integer of 0 to 2, and

L is a substituted or unsubstituted divalent cyclic group of one of the following compounds,

12. The method as claimed in claim 1, wherein the polymer has a weight average molecular weight of about 500 to about 200,000.

13. The method as claimed in claim 1, wherein the curing after applying the second composition is performed at a temperature that is higher than a temperature at which the curing after applying the first composition is performed.

14. The method as claimed in claim 1, wherein the first composition and the second composition each independently include a surfactant, a plasticizer, a cross-linking agent, a thermal acid generator, a photoacid generator, or a combination thereof.

15. The method as claimed in claim 14, wherein the cross-linking agent includes methoxymethylated glycoluril, butoxymethylated glycoluril, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzoguanamine, butoxymethylated benzoguanamine, methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, butoxymethylated thiourea, methoxymethylatedbenzene, butoxymethylated benzene, methoxymethylated phenol, butoxymethylated phenol, or a combination thereof.

16. The method as claimed in claim 1, wherein the solvent of the first composition and the solvent of second composition each independently include propylene glycol, propylene glycol diacetate, methoxy propanediol, diethylene glycol, diethylene glycol butylether, tri(ethylene glycol)monomethylether, propylene glycol monomethylether, propylene glycol monomethylether acetate, cyclohexanone, ethyllactate, gamma-butyrolactone, N,N-dimethyl formamide, N,N-dimethyl acetamide, methylpyrrolidone, methylpyrrolidinone, acetylacetone, ethyl 3-ethoxypropionate, or a combination thereof.

17. The method as claimed in claim 1, wherein:

coating the first composition includes applying the first composition to a thickness of about 300 Å

to about 10 μ

m, and

coating the second composition includes applying the second composition to a thickness of about 300 Å

to about 10 μ

m.

18. The method as claimed in claim 1, wherein:

one side of the substrate has a first part having a pattern thereon and a second part without a pattern thereon, and

a sum of step differences of the second organic layer is smaller than a sum of step differences of the first organic layer.

19. A method of forming a pattern, the method comprising:

providing a layer structure produced according to the method as claimed in claim 1;

forming a silicon-containing thin layer on the layer structure;

forming a photoresist layer on the silicon-containing thin layer;

exposing and developing the photoresist layer to form a photoresist pattern; and

selectively removing the silicon-containing thin layer and the first organic layer, the second organic layer, or a combination thereof in the layer structure using the photoresist pattern.

20. The method as claimed in claim 19, further comprising forming a bottom antireflective coating prior to forming the photoresist.