IP Library Granted Patent US 10,886,119
Granted Patent B2
US 10,886,119 · App. 16/502,062 · Granted Jan 5, 2021

Aromatic underlayer

Inventors: Sheng Liu (Bow, NH); James F. Cameron (Brookline, MA); Shintaro Yamada (Shrewsbury, MA)
Assignee: Rohm and Haas Electronic Materials LLC
H01L21/02118C08L61/30C08L65/00H01L21/02532H01L21/3213C08L2203/206
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Quick Facts
Patent No.
US 10,886,119
App. No.
16/502,062
Granted
Jan 5, 2021
Kind
B2
Abstract

Curable homopolymers formed from monomers having two 2-naphthol moieties are useful as underlayers in semiconductor manufacturing processes.

Claims (14)

1. A method comprising: (a) providing an electronic device substrate; (b) coating a layer of a coating composition comprising one or more curable compounds on a surface of the electronic device substrate, wherein the one or more curable compounds is a polymer comprising repeating units of formula (1)

wherein Z is a covalent chemical bond or a divalent linking group chosen from O, C(═O), S, S(═O), S(═O) 2 , N(R), C 1-100 -hydrocarbylene, substituted C 1-100 -hydrocarbylene, —O—(C 1-20 -alkylene-O—) m1 , —O—(C 5-60 -arylene-O—) m2 , and C(R 3 )(R 4 ); R is chosen from H, C 1-20 -alkyl, C 5-30 -aryl, and C 2-20 -unsaturated aliphatic moiety; each R 1 and each R 2 are independently chosen from H, OR, C 1-30 -hydrocarbyl, substituted C 1-30 -hydrocarbyl, —C(═O)—O—R 5 , SR, S(═O)R, S(═O) 2 R, N(R 5 )(R 6 ), and N(R 7 )C(═O)R 5 ; one R 1 and one R 2 and Z may be taken together along with the atoms to which they are attached to form a 5 to 6-membered ring; R 3 and R 4 are independently chosen from C 1-20 -alkyl and C 5-30 -aryl; R 5 and R 6 are independently C 1-20 -alkyl or C 5-30 -aryl; R 7 is H or R 6 ; R 5 and R 6 may be taken together along with the atoms to which they are attached to form a 5- to 6-membered ring; each of a1 and a2 is from 0 to 5; each of m1 and m2=1 to 100; and n=2 to 1000; wherein a first 2-naphthol moiety of a first repeating unit of formula (1) is bonded by a single bond to a second 2-naphthol moiety of a second repeating unit of formula (1) at the respective 1-position of the first 2-naphthol moiety and second 2-naphthol moiety; (c) curing the layer of the curable compound to form an underlayer; (d) coating a layer of a photoresist on the underlayer; (e) exposing the photoresist layer to actinic radiation through a mask; (f) developing the exposed photoresist layer to form a resist pattern; and (g) transferring the pattern to the underlayer to expose portions of the electronic device substrate.

2. The method of claim 1 further comprising the steps of patterning the substrate; and then removing the patterned underlayer.

3. The method of claim 1 further comprising the step of coating one or more of a silicon-containing layer, an organic antireflective coating layer and a combination thereof over the underlayer before step (d).

4. The method of claim 3 further comprising the step of transferring the pattern to the one or more of the silicon-containing layer, the organic antireflective coating layer and the combination thereof after step (f) and before step (g).

5. The method of claim 1 wherein the coating composition further comprises one or more of an organic solvent, a curing agent, and a surface leveling agent.

6. The method of claim 1 wherein the repeating units of formula (1) are chosen from formulae:

7. An electronic device comprising an electronic device substrate having a layer of a polymer comprising as polymerized units one or more curable compounds on a surface of the electronic device substrate, wherein the one or more curable compounds is a polymer comprising repeating units of formula (1)

wherein Z is a covalent chemical bond or a divalent linking group chosen from O, C(═O), S, S(═O), S(═O) 2 , N(R), C 1-100 -hydrocarbylene, substituted C 1-100 -hydrocarbylene, —O—(C 1-20 -alkylene-O—) m1 , —O—(C 5-60 -arylene-O—) m2 , and C(R 3 )(R 4 ); R is chosen from H, C 1-20 -alkyl, C 5-30 -aryl, and C 2-20 -unsaturated aliphatic moiety; each R 1 and each R 2 are independently chosen from H, OR, C 1-30 -hydrocarbyl, substituted C 1-30 -hydrocarbyl, —C(═O)—O—R 5 , SR, S(═O)R, S(═O) 2 R, N(R 5 )(R 6 ), and N(R7)C(═O)R 5 ; one R 1 and one R 2 and Z may be taken together along with the atoms to which they are attached to form a 5 to 6-membered ring; R 3 and R 4 are independently chosen from C 1-20 -alkyl and C 5-30 -aryl; R 5 and R 6 are independently C 1-20 -alkyl or C 5-30 -aryl; R 7 is H or R 6 ; R 5 and R 6 may be taken together along with the atoms to which they are attached to form a 5- to 6-membered ring; each of a1 and a2 is from 0 to 5; each of m1 and m2=1 to 100; and n=2 to 1000; wherein a first 2-naphthol moiety of a first repeating unit of formula (1) is bonded by a single bond to a second 2-naphthol moiety of a second repeating unit of formula (1) at the respective 1-position of the first 2-naphthol moiety and second 2-naphthol moiety.

8. A polymer comprising repeating units of formula (1)

wherein Z is a covalent chemical bond or a divalent linking group chosen from O, C(═O), S, S(═O), S(═O) 2 , N(R), C 1-100 -hydrocarbylene, substituted C 1-100 -hydrocarbylene, —O—(C 1-20 -alkylene-O—) m1 , —O—(C 5-60 -arylene-O—) m2 , and C(R 3 )(R 4 ); R is chosen from H, C 1-20 -alkyl, C 5-30 -aryl, and C 2-20 -unsaturated aliphatic moiety; each R 1 and each R 2 are independently chosen from H, OR, C 1-30 -hydrocarbyl, substituted C 1-30 -hydrocarbyl, —C(═O)—O—R 5 , SR, S(═O)R, S(═O) 2 R, N(R 5 )(R 6 ), and N(R7)C(═O)R 5 ; one R 1 and one R 2 and Z may be taken together along with the atoms to which they are attached to form a 5 to 6-membered ring; R 3 and R 4 are independently chosen from C 1-20 -alkyl and C 5-30 -aryl; R 5 and R 6 are independently C 1-20 -alkyl or C 5-30 -aryl; R 7 is H or R 6 ; R 5 and R 6 may be taken together along with the atoms to which they are attached to form a 5- to 6-membered ring; each of a1 and a2 is from 0 to 5; each of m1 and m2=1 to 100; and n=2 to 1000; wherein a first 2-naphthol moiety of a first repeating unit of formula (1) is bonded by a single bond to a second 2-naphthol moiety of a second repeating unit of formula (1) at the respective 1-position of the first 2-naphthol moiety and second 2-naphthol moiety.

9. The method of claim 1 wherein Z is a covalent chemical bond or a divalent linking group chosen from —O—(C 5-60 -arylene-O—) m2 , and m2=1 to 100.

10. The electronic device of claim 7 wherein Z is a covalent chemical bond or a divalent linking group chosen from —O—(C 5-60 -arylene-O—) m2 , and m2=1 to 100.

11. The polymer of claim 8 wherein Z is a covalent chemical bond or a divalent linking group chosen from —O—(C 5-60 -arylene-O—) m2 , and m2=1 to 100.

Assignments (4)
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 073515/0243 →
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 073517/0298 →
CHANGE OF NAME Recorded Oct 29, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS LLC
To: DUPONT ELECTRONIC MATERIALS INTERNATIONAL, LLC
Reel/Frame 069272/0383 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 27, 2022
From: LIU, SHENG; CAMERON, JAMES F.; YAMADA, SHINTARO
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 058787/0280 →
Cited By (1)
US 12,535,736