IP Library Granted Patent US 10,416,561
Granted Patent B2
US 10,416,561 · App. 15/454,021 · Granted Sep 17, 2019

Coating composition, and process for producing photoresist laminate

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Quick Facts
Patent No.
US 10,416,561
App. No.
15/454,021
Granted
Sep 17, 2019
Kind
B2
Abstract

A coating composition which contains a fluorinated polymer having a unit (1) represented by —[CX 1 X 2 —CY 1 (Rf 1 —COOM 1 )]— and a fluorinated compound represented by CX 3 X 4 ═CY 2 (Rf 2 —COOM 2 ), wherein the content of the fluorinated compound is from 0.1 to 8.0 parts by mass per 100 parts by mass of the fluorinated polymer. X 1 , X 2 , X 3 and X 4 are H, F or Cl, Y 1 and Y 2 are H, F, Cl, a methyl group or a trifluoromethyl group, Rf 1 and Rf 2 are a perfluoroalkylene group which may contain an etheric oxygen atom between carbon-carbon atoms, or an oxyperfluoroalkylene group which may contain an etheric oxygen atom between carbon-carbon atoms, —COOM 1 is —COOH or —COOZ 1 , and —COOM 2 is —COOH or —COOZ 2 (wherein Z 1 and Z 2 are an ammonium ion in which the hydrogen atom may be substituted). The coating composition is suitable for forming a thin antireflection coating layer without increasing its refractive index.

Claims (21)

1. A coating composition, comprising:

a fluorinated polymer having a unit represented by formula (1); and

a fluorinated compound represented by formula (2), wherein the content of the fluorinated compound is from 0.1 to 8.0 parts by mass per 100 parts by mass of the fluorinated polymer, and the fluorinated polymer has number average molecular weight of from 1,000 to 30,000:

—[CX 1 CX 2 —CY 1 (Rf 1 —COOM 1 )]—  (1)

wherein X 1 and X 2 are each independently a hydrogen atom, a fluorine atom or a chlorine atom, Y 1 is a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group or a trifluoromethyl group, Rf 1 is a perfluoroalkylene group which may contain an etheric oxygen atom between carbon-carbon atoms, or an oxyperfluoroalkylene group which may contain an etheric oxygen atom between carbon-carbon atoms, the number of carbon atoms in Rf 1 is from 1 to 10 or in the case that Rf 1 contains the etheric oxygen atom, from 2 to 10, and —COOM 1 is —COOH or —COOZ 1 , wherein Z 1 is an ammonium ion in which the hydrogen atom may be substituted;

CX 3 X 4 ═CY 2 (Rf 2 —COOM 2 )  (2)

wherein X 3 and X 4 are each independently a hydrogen atom, a fluorine atom or a chlorine atom, Y 2 is a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group or a trifluoromethyl group, Rf 2 is a perfluoroalkylene group which may contain an etheric oxygen atom between carbon-carbon atoms, or an oxyperfluoroalkylene group which may contain an etheric oxygen atom between carbon-carbon atoms, the number of carbon atoms in Rf 2 is from 1 to 10 or in the case that Rf 2 contains the etheric oxygen atom, from 2 to 10, and —COOM 2 is —COOH or —COOZ 2 , wherein Z 2 is an ammonium ion in which the hydrogen atom may be substituted.

2. The coating composition according to claim 1 , wherein all of X 1 , X 2 and Y 1 are fluorine atoms.

3. The coating composition according to claim 1 , wherein the content of the fluorinated polymer in the coating composition is from 1 to 25 mass %.

4. The coating composition according to claim 1 , wherein CX 1 X 2 in the fluorinated polymer is equal to CX 3 X 4 in the fluorinated compound.

5. The coating composition according to claim 1 , wherein CY 1 in the fluorinated polymer is equal to CY 2 in the fluorinated compound.

6. The coating composition according to claim 1 , wherein COOM 1 in the fluorinated polymer is equal to COOM 2 in the fluorinated compound.

7. The coating composition according to claim 1 , wherein Rf 1 in the fluorinated polymer is equal to Rf 2 in the fluorinated compound.

8. The coating composition according to claim 1 , further comprising an additional polymer different from the fluorinated polymer, and wherein the content of the additional polymer in the coating composition is from 1 to 50 mass % based on the total amount of the fluorinated polymer and the additional polymer.

9. A process for producing a photoresist laminate having an antireflection coating layer provided on the surface of a photoresist layer, comprising:

applying a coating liquid which comprises the coating composition as defined in claim 8 and in which the total content of the fluorinated polymer and the additional polymer is from 1 to 10 mass %, to the surface of the photoresist layer; and

drying the coating liquid to form the antireflection coating layer.

10. The coating composition according to claim 1 , further comprising a solvent.

11. A process for producing a photoresist laminate having an antireflection coating layer provided on the surface of a photoresist layer, comprising:

applying a coating liquid which comprises the coating composition as defined in claim 1 and in which the content of the fluorinated polymer is from 1 to 10 mass %, to the surface of the photoresist layer; and

drying the coating liquid to form the antireflection coating layer.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 3, 2019
From: YAMASAKI, RYUJIRO; ITO, MASAHIRO; SAKANE, YOSHIHIKO
To: ASAHI GLASS COMPANY, LIMITED
Reel/Frame 049342/0704 →
CHANGE OF NAME Recorded Aug 7, 2018
From: ASAHI GLASS COMPANY, LIMITED
To: AGC INC.
Reel/Frame 046730/0786 →