IP Library Granted Patent US 10,290,500
Granted Patent B2
US 10,290,500 · App. 15/511,416 · Granted May 14, 2019

Spin on hard mask material

Inventors: Alex Phillip Graham Robinson (Birmingham, GB); Andeas Frommhold (Dera, DE); Alan Brown (Worcestershire, GB); Tom Lada (Somerville, MA)
Assignee: Irresistible Materials LTD
H01L21/0274B05D1/005B05D3/002B05D3/0254C01B32/152C09D163/04C09D177/00H01L21/02115H01L21/02282H01L21/02318H01L21/3065H01L21/3081H01L21/31122H01L21/31138
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Quick Facts
Patent No.
US 10,290,500
App. No.
15/511,416
Granted
May 14, 2019
Kind
B2
Abstract

Disclosed and claimed herein is a composition for forming a spin-on hard-mask, having a fullerene derivative and a crosslinking agent. Further disclosed is a process for forming a hard-mask.

Claims (19)

1. A composition for forming a spin-on hard-mask, comprising:

a) a fullerene derivative expressed by the general formula

 wherein n is an integer of 1-6, Q, the number of carbon atoms in the fullerene, is 60, 70, 76, 78, 80, 82, or 84, R 1 represents a first substituent comprising an ester, an alcohol, a phenol, an amine, an amide, an imide, or a carboxylic acid and R 2 represents a second substituent comprising hydrogen, a halogen, a C 6 -C 20 aryl group, a C 1 -C 20 alkyl group, an ester, an alcohol, a phenol, an amine, an amide, an imide, or a carboxylic acid,

b) a crosslinking agent comprising two or more thermally or catalytically reactive groups,

wherein the crosslinking agent is a polyaromatic, wherein the polyaromatic is 4,4′-(9-fluorenylidene) dianiline.

2. The composition of claim 1 , further comprising one or more additional fullerene derivatives, wherein at least one of Q=60 and at least a second Q=70.

3. The composition of claim 2 , further comprising one or more thermal acid generators.

4. The composition of claim 2 , wherein R 1 is a carboxylic acid.

5. The composition of claim 2 , wherein the crosslinking agent is chosen from an epoxy phenolic novolak resin, an epoxy cresylic novolak resin, an epoxy bisphenol A resin, an epoxy bisphenol A novolak resin, an epoxy bisphenol C resin, an alkylolmethyl melamine resin, an alkylolmethyl glycoluril resin, an alkylolmethyl guanamine resin, an alkylolmethyl benzo-guanamine resin, a glycosyl urea resin, or an alkyd resin.

6. The composition of claim 5 , further comprising one or more thermal acid generators.

7. The composition of claim 6 , wherein the one or more thermal acid generators are chosen from alkyl esters of organic sulfonic acids, alicyclic esters of organic sulfonic acids, amine salts of organic sulfonic acids, 2-nitrobenzyl esters of organic sulfonic acids, 4-nitrobenzyl esters of organic sulfonic acids, benzoin esters of organic sulfonic acids, β-hydroxyalkyl esters of organic sulfonic acids, β-hydroxycycloalkyl esters of organic sulfonic acids, triaryl sulfonium salts of organic sulfonic acids, alkyl diaryl sulfonium salts of organic sulfonic acids, dialkyl aryl sulfonium salts of organic sulfonic acids, trialkyl sulfonium salts of organic sulfonic acids, diaryl iodonium salts of organic sulfonic acids, alkyl aryl sulfonium salts of organic sulfonic acids, or ammonium salts of tris(organosulfonyl) methides.

8. The composition of claim 5 , further comprising one or more photoacid generators.

9. The composition of claim 8 , wherein the one or more photoacid generators are chosen from halogenated triazines, 2-nitrobenzyl esters of organic sulfonic acids, 4-nitrobenzyl esters of organic sulfonic acids, triaryl sulfonium salts of organic sulfonic acids, alkyl diaryl sulfonium salts of organic sulfonic acids, dialkyl aryl sulfonium salts of organic sulfonic acids, diaryl iodonium salts of organic sulfonic acids, alkyl aryl sulfonium salts of organic sulfonic acids, n-organosulfonyloxybicyclo[2.2.1]-hept-5-ene-2,3-dicarboximides, or 1,3-dioxoisoindolin-2-yl organosulfonates.

10. The composition of claim 5 , wherein the crosslinking agent is chosen from an epoxidized phenolic resin, an epoxidized cresylic resin, an epoxidized bisphenol A resin, an expoxidized bis-phenol A novolak resin, an epoxy bisphenol resin, an alkylolmethyl melamine resin, an alkylolmethyl glycoluril resin, an alkylolmethyl guanamine resin, an alkylomethy Benzo-Guanamine resin, a glycosyl urea resin, or an isocyanate resin.

11. The composition of claim 5 , wherein the spin-on hard-mask further comprises one or more solvents chosen from polyethylene glycol monomethyl ether acetate, ethyl lactate, anisole, toluene, chloroform, chlorobenzene, o-dichloro benzene, m-dichloro benzene, p-dichloro benzene, o-xylene, m-xylene, p-xylene, carbon disulfide or combinations thereof.

12. A process for forming a spin-on hard-mask, comprising:

a) providing a composition of claim 1 ,

b) forming a coating on a substrate; and

c) heating the substrate and the coating at a temperature sufficient to cross-link the coating.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 4, 2022
From: ROBINSON, ALEX P. G.
To: IRRESISTIBLE MATERIALS LTD
Reel/Frame 058540/0058 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 4, 2022
From: FROMMHOLD, ANDREAS
To: IRRESISTIBLE MATERIALS LTD
Reel/Frame 058540/0349 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 4, 2022
From: BROWN, ALAN
To: IRRESISTIBLE MATERIALS LTD
Reel/Frame 058540/0697 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 4, 2022
From: LADA, TOM
To: IRRESISTIBLE MATERIALS LTD
Reel/Frame 058541/0012 →
Continuity (2)
Provisional Application 62061294 · Oct 8, 2014
Related Publication 20170278703A1 · Sep 28, 2017