IP Library › Granted Patent US 9,773,673
Granted Patent B2
US 9,773,673 · App. 15/148,622 · Granted Sep 26, 2017

Composition for manufacturing semiconductor device and method of manufacturing semiconductor device using the composition

Inventors: Jin Park (Yongin-si, KR); Hyun-woo Kim (Seongnam-si, KR); Myeong-koo Kim (Suwon-si, KR)
Assignee: Samsung Electronics Co., Ltd.
H01L21/0337C09D179/08G03F7/11H01L21/0276H01L21/0332
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Quick Facts
Patent No.
US 9,773,673
App. No.
15/148,622
Granted
Sep 26, 2017
Kind
B2
Abstract

A composition for manufacturing a semiconductor device includes at least one carbon-based compound that includes at least one of an alkyne group and an azide group, and a solvent. A method of manufacturing a semiconductor device includes forming a feature layer on a substrate, coating the feature layer with a composition including alkyne and azide, forming a carbon-containing layer including a triazole compound by performing a heat treatment on the coated composition, forming a photoresist film on the carbon-containing layer, forming photoresist patterns by exposing and developing the photoresist film, and patterning the carbon-containing layer and the feature layer using the photoresist patterns.

Claims (50)

1. A composition for manufacturing a semiconductor device, the composition comprising:

at least one carbon-based compound including at least one of an alkyne group and an azide group; and

a solvent;

wherein the at least one carbon-based compound comprises a first compound including alkyne and a second compound including azide.

2. The composition of claim 1 , wherein the first compound is expressed by the following Formula (1):

R 1 ≡R 2 ,  Formula (1)

wherein R 1 is a C1-C50 aliphatic hydrocarbon group or a C6-C50 aromatic hydrocarbon group, and R 2 is a hydrogen atom, a C1-C50 aliphatic hydrocarbon group, or a C6-C50 aromatic hydrocarbon group; and

the second compound is expressed by the following Formula (2):

N 3 —R 3 ,  Formula (2)

wherein R 3 is a C1-C50 aliphatic hydrocarbon group or a C6-C50 aromatic hydrocarbon group.

3. The composition of claim 1 , wherein the first compound is expressed by the following Formula (1-1):

wherein R 4 includes at least one of a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 heteroalkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, a substituted or unsubstituted C2-C20 alkynyl group, and a substituted or unsubstituted C2-C20 heteroalkynyl group,

each of R 5 and R 6 independently includes a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, a nitro group, a cyano group, an amino group, an azido group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamyl group, a thiol group, an ester group, a carboxyl group, a carboxyl group salt, a sulfonic acid group, a sulfonic acid group salt, a phosphoric acid, a phosphate, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C7-C40 aryl, substituted or unsubstituted C6-C40 aryloxy, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C1-C40 alkylamino, substituted or unsubstituted C6-C40 arylamino, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C8-C40 aryl silyl, substituted or unsubstituted C7-C40 ketoaryl, substituted or unsubstituted C7-C40 ketoheteroaryl, substituted or unsubstituted C1-C40 haloalkyl, a C1-C40 fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, and a fused heteroaromatic ring, and

m is an integer from 1 to 10.

4. The composition of claim 1 , wherein the second compound is expressed by the following Formula (2-1):

wherein R 7 includes at least one of a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 heteroalkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, a substituted or unsubstituted C2-C20 alkynyl group, and a substituted or unsubstituted C2-C20 heteroalkynyl group,

each of R 8 and R 9 independently includes at least one of a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, a nitro group, a cyano group, an amino group, an azido group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamyl group, a thiol group, an ester group, a carboxyl group, a carboxyl group salt, a sulfonic acid group, a sulfonic acid group salt, a phosphoric acid, a phosphate, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C7-C40 aryl, substituted or unsubstituted C6-C40 aryloxy, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C1-C40 alkylamino, substituted or unsubstituted C6-C40 arylamino, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C8-C40 aryl silyl, substituted or unsubstituted C7-C40 ketoaryl, substituted or unsubstituted C7-C40 ketoheteroaryl, substituted or unsubstituted C1-C40 haloalkyl, a C1-C40 fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, and a fused heteroaromatic ring, and

n is an integer from 1 to 10.

5. The composition of claim 1 , wherein the at least one carbon-based compound further comprises a third compound having a structure that is different from a structure of at least one of the first and second compounds.

6. The composition of claim 1 , wherein the first compound is expressed by the following Formula (1-3):

where R 11 includes at least one of a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 heteroalkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, a substituted or unsubstituted C2-C20 alkynyl group, and a substituted or unsubstituted C2-C20 heteroalkynyl group, and

each of R 12 , R 13 , R 14 , and R 15 independently includes at least one of a hydrogen atom, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C7-C40 aryl, substituted or unsubstituted C6-C40 aryloxy, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C1-C40 alkylamino, substituted or unsubstituted C6-C40 arylamino, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C8-C40 aryl silyl, substituted or unsubstituted C7-C40 ketoaryl, substituted or unsubstituted C7-C40 ketoheteroaryl, substituted or unsubstituted C1-C40 haloalkyl, a C1-C40 fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, and a fused heteroaromatic ring.

7. The composition of claim 1 , wherein the second compound is expressed by the following Formula (2-3):

wherein R 16 is a C1-C50 aliphatic hydrocarbon group or a C6-C50 aromatic hydrocarbon group, and

each of R 17 , R 18 , R 19 , and R 20 independently includes at least one of a hydrogen atom, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C7-C40 aryl, substituted or unsubstituted C6-C40 aryloxy, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C1-C40 alkylamino, substituted or unsubstituted C6-C40 arylamino, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C8-C40 aryl silyl, substituted or unsubstituted C7-C40 ketoaryl, substituted or unsubstituted C7-C40 ketoheteroaryl, substituted or unsubstituted C1-C40 haloalkyl, a C1-C40 fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, and a fused heteroaromatic ring.

8. A composition for manufacturing a semiconductor device, the composition comprising:

at least one carbon-based compound including at least one of an alkyne group and an azide group; and

a solvent;

wherein the at least one carbon-based compound comprises a fourth compound including alkyne and azide.

9. A composition for manufacturing a semiconductor device, the composition comprising:

at least one carbon-based compound including at least one of an alkyne group and an azide group; and

a solvent;

wherein the at least one carbon-based compound comprises a fourth compound expressed by the following Formula (4):

wherein “A” includes a carbon-based compound including at least one substituted or unsubstituted ring,

R 21 and R 22 are substantially equal to or different from each other, and each of R 21 and R 22 independently includes at least one of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 heteroalkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, a substituted or unsubstituted C2-C20 alkynyl group, and a substituted or unsubstituted C2-C20 heteroalkynyl group.

10. The composition of claim 1 , wherein at least one of the first and second compounds comprises at least one heteroatom from nitrogen (N), oxygen (O), phosphorus (P), sulfur (S), boron (B), silicon (Si), a halogen atom, and a metal atom.

11. The composition of claim 5 , wherein the third compound does not comprise alkyne and azide.

12. The composition of claim 5 , wherein the third compound comprises pyromellitic dianhydride (PMDA).

13. The composition of claim 5 , wherein the third compound comprises at least one heteroatom from nitrogen (N), oxygen (O), phosphorus (P), sulfur (S), boron (B), silicon (Si), a halogen atom, and a metal atom.

14. The composition of claim 9 , wherein “A” comprises a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, or a fused heteroaromatic ring.

15. The composition of claim 9 , wherein “A” comprises at least one of substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C7-C40 aryl, substituted or unsubstituted C6-C40 aryloxy, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C1-C40 alkylamino, substituted or unsubstituted C6-C40 arylamino, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C8-C40 aryl silyl, substituted or unsubstituted C7-C40 ketoaryl, substituted or unsubstituted C7-C40 ketoheteroaryl, substituted or unsubstituted C1-C40 haloalkyl, and a cyano group.

16. The composition of claim 9 , wherein “A” comprises at least one heteroatom from nitrogen (N), oxygen (O), phosphorus (P), sulfur (S), boron (B), silicon (Si), a halogen atom, and a metal atom.

17. The composition of claim 9 , wherein each of R 21 and R 22 independently comprises one of a methyl group, an ethyl group, a phenyl group, a pyridinyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a biphenyl group, an iptycenyl group, a tartrate ester group, an acetylene group, an alkene group, and combinations thereof.

18. The composition of claim 9 , wherein the fourth compound is expressed by the following Formula (4-1):

wherein each of R 21 and R 22 independently includes one of a methyl group, an ethyl group, a phenyl group, a pyridinyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a biphenyl group, an iptycenyl group, a tartrate ester group, an acetylene group, an alkene group, and combinations thereof,

R 23 includes at least one of a hydrogen atom, a C1-C50 aliphatic hydrocarbon group, and a C6-C50 aromatic hydrocarbon group, and

each of k, m, and n is an integer from 1 to 10.

19. The composition of claim 9 , wherein the fourth compound is expressed by the following Formula (4-2):

wherein each of R 24 and R 25 independently includes at least one of a hydrogen atom, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C7-C40 aryl, substituted or unsubstituted C6-C40 aryloxy, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C1-C40 alkylamino, substituted or unsubstituted C6-C40 arylamino, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C8-C40 aryl silyl, substituted or unsubstituted C7-C40 ketoaryl, substituted or unsubstituted C7-C40 ketoheteroaryl, substituted or unsubstituted C1-C40 haloalkyl, a C1-C40 fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, and a fused heteroaromatic ring.

20. The composition of claim 9 , wherein the fourth compound is expressed by the following Formula (4-3):

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 9, 2016
From: PARK, JIN; KIM, HYUN-WOO; KIM, MYEONG-KOO
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 038512/0901 →
Priority Claims (1)
KR 10-2015-0118877 · Aug 24, 2015 · national
Continuity (1)
Related Publication 20170062217A1 · Mar 2, 2017