IP Library › Granted Patent US 11,327,398
Granted Patent B2
US 11,327,398 · App. 16/399,473 · Granted May 10, 2022

Photoresist compositions and methods for fabricating semiconductor devices using the same

Inventors: Chawon Koh (Yongin-si, KR); Tsunehiro Nishi (Seongnam-si, KR); Brian Cardineau (Corvallis, OR); Sangyoon Woo (Leuven, BE); Jason Stowers (Corvallis, OR); Soo Young Choi (Hwaseong-si, KR)
Assignees: Samsung Electronics Co., Ltd.; Inpria Corporation
G03F7/0042G03F7/11G03F7/2004H01L21/0274H01L21/31144G03F7/325
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Quick Facts
Patent No.
US 11,327,398
App. No.
16/399,473
Granted
May 10, 2022
Kind
B2
Abstract

Provided herein are photoresist compositions and methods for fabricating semiconductor devices using the same. A photoresist composition may include an organometallic material, a fluorine-containing material, and an organic solvent.

Claims (58)

1. A photoresist composition, comprising:

an organometallic material;

a fluorine-containing material; and

an organic solvent,

wherein the fluorine-containing material has a structure represented by one of formula (1) to (14):

wherein:

a, b and c, if present, are each independently a natural number;

R 1 , if present, is fluorine;

R 2 , if present, is each independently hydrogen or a hydrophilic group; and

R 3 , if present, is a hydrophobic group; and

wherein, in formulae (7) to (10), a/(a+b) is 0.1-1 and b/(a+b) is 0.0-0.9; and

wherein, in formulae (11) to (14), a/(a+b+c) is 0.0-0.9, b/(a+b+c) is 0.1-1, and c/(a+b+c) is 0.0-0.9.

2. The photoresist composition of claim 1 , wherein the organometallic material is an organometallic nano-cluster material, and wherein the fluorine-containing material is a fluorine-containing polymer material.

3. The photoresist composition of claim 1 , wherein the organometallic material is present in the photoresist composition in an amount of 0.1-99 wt. % of the photoresist composition, the fluorine-containing material is present in the photoresist composition in an amount of 0.1-30 wt. % of the photoresist composition, and the organic solvent is present in the photoresist composition in an amount of 0.9-99.8 wt. % of the photoresist composition.

4. The photoresist composition of claim 1 , wherein the organometallic material comprises at least one metal selected from the group consisting of: tin (Sn), indium (In), antimony(Sb), and hafnium (Hf).

5. The photoresist composition of claim 1 , wherein the organic solvent comprises methyl isobutyl carbinol (MIBC), ether, propylene glycol monomethylether acetate (PGMEA), propylene glycol monomethylether (PGME), ethyl lactate (EL), and/or β-hydroxy β-methylbutyric acid (HBM).

6. The photoresist composition of claim 1 , further comprising a surfactant in an amount of 0.01-3 wt. % of the photoresist composition.

7. The photoresist composition of claim 1 , wherein the organometallic material has a chemical formula represented by one of formula (15) to (17):

R w MeO (2−(w−2)−(x/2)) (OH) x ,  (15)

R y MeL 4−y ,  (16)

or

RMeO (3/2−z/2) (OH) z ;  (17)

wherein:

R is a hydrocarbon compound having 1 to 30 carbon atoms and includes at least one atom selected from carbon, nitrogen and oxygen,

Me is selected from the group consisting of: tin (Sn), indium (In), antimony (Sb), and hafnium (Hf); and

wherein, in formula (15), 0<w≤2 and 0<(w+x)≤4, in formula (16), y is 1 or 2, and L is a metal ligand, and,

in formula (17), 0<z<3.

8. The photoresist composition of claim 1 , further comprising a moisture absorbent in an amount of 0.01-10 wt. % of the photoresist composition.

9. The photoresist composition of claim 8 , wherein the moisture absorbent is selected from the group consisting of polyoxyethylene nonylphenolether, R 5 C 6 H 4 C(CH 2 CH 2 O) n H, polyethylene glycol (PEG), HO(CH 2 CH 2 O) n H, and polyacrylamide, wherein R 5 is a hydrocarbon compound having 1 to 30 carbon atoms and includes at least one atom selected from carbon, nitrogen and oxygen and n is a natural number selected from 1 to 1,000.

10. The photoresist composition of claim 1 , further comprising water in an amount of 0.001-0.1 wt. % of the photoresist composition.

11. A photoresist composition, comprising:

an organometallic material;

a fluorine-containing material; and

an organic solvent,

wherein the organometallic material has a chemical formula represented by formula (15) or formula (17):

R w MeO (2−(w−2)−(x/2)) (OH) x ;  (15)

RMeO (3/2−z/2) (OH) z ,  (17)

wherein:

R is a hydrocarbon compound having 1 to 30 carbon atoms and includes at least one atom selected from carbon, nitrogen and oxygen;

Me is selected from the group consisting of tin (Sn), indium (In), antimony (Sb), and hafnium (Hf); and

in formula (15), 0<w≤2 and 0<(w+x)≤4, and, in formula (17), 0<z<3.

12. The photoresist composition of claim 11 , wherein the organometallic material is an organometallic nano-cluster material, and wherein the fluorine-containing material is a fluorine-containing polymer material.

13. The photoresist composition of claim 11 , wherein the organometallic material is present in the photoresist composition in an amount of 0.1-99 wt. % of the photoresist composition, the fluorine-containing material is present in the photoresist composition in an amount of 0.1-30 wt. % of the photoresist composition, and the organic solvent is present in the photoresist composition in an amount of 0.9-99.8 wt. % of the photoresist composition.

14. The photoresist composition of claim 11 , wherein:

the fluorine-containing material has a structure represented by one of formula (1) to (14):

wherein:

a, b and c, if present, are each independently a natural number;

R 1 , if present, is fluorine;

R 2 , if present, is each independently hydrogen or a hydrophilic group; and

R 3 , if present, is a hydrophobic group; and

wherein, in formulae (7) to (10), a/(a+b) is 0.1-1 and b/(a+b) is 0.0-0.9; and

wherein, in formulae (11) to (14), a/(a+b+c) is 0.0-0.9, b/(a+b+c) is 0.1-1, and c/(a+b+c) is 0.0-0.9.

15. The photoresist composition of claim 11 , wherein the fluorine-containing material comprises at least one functional group selected from the group consisting of —CFOH, —CHCFOH, —CHCFCFOH, —C(CF)OH, —CFCF(CF)OH, and —CHC(CF)OH.

16. The photoresist composition of claim 11 , wherein the organic solvent comprises methyl isobutyl carbinol (MIBC), ether, propylene glycol monomethylether acetate (PGMEA), propylene glycol monomethylether (PGME), ethyl lactate (EL), and/or β-hydroxy β-methylbutyric acid (HBM).

17. The photoresist composition of claim 11 , further comprising a surfactant in an amount of 0.01-3 wt. % of the photoresist composition.

18. The photoresist composition of claim 11 , further comprising a moisture absorbent in an amount of 0.01-10 wt. % of the photoresist composition.

19. The photoresist composition of claim 18 , wherein the moisture absorbent is selected from the group consisting of polyoxyethylene nonylphenolether, R 5 C 6 H 4 C(CH 2 CH 2 O) n H, polyethylene glycol (PEG), HO(CH 2 CH 2 O) n H, and polyacrylamide, wherein R 5 is a hydrocarbon compound having 1 to 30 carbon atoms and includes at least one atom selected from carbon, nitrogen and oxygen and n is a natural number selected from 1 to 1,000.

20. The photoresist composition of claim 11 , further comprising water in an amount of 0.001-0.1 wt. % of the photoresist composition.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 30, 2019
From: KOH, CHAWON; NISHI, TSUNEHIRO; CHOI, SOO YOUNG
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 049039/0086 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 30, 2019
From: CARDINEAU, BRIAN; WOO, SANGYOON; STOWERS, JASON
To: INPRIA CORPORATION
Reel/Frame 049039/0190 →
Continuity (1)
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Cited By (1)
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