Composition for forming coating film and method for forming coating film using same

Patent metadata

Field	Value
Publication number	US-10875969-B2
Application number	US-201615567846-A
Country	US
Kind code	B2
Filing date	Mar 23, 2016
Priority date	Apr 20, 2015
Publication date	Dec 29, 2020
Grant date	Dec 29, 2020

Abstract

[Problem] To provide a composition for forming a coating layer having excellent gas barrier performance and a method of forming the coating layer. [Means for Solution] A composition for forming a coating film comprising a specific silicon compound which reacts with a polysilazane by exposure, a polysilazane and an organic solvent, and a method for forming a coating layer comprising coating the composition on a substrate and exposing.

First claim

The invention claimed is:

1. A composition for forming a coating film, comprising:
a silicon compound represented by the following formula (1):

wherein
R 1 s are monovalent groups independently selected from the group consisting of hydrogen, halogen atom, hydrocarbyl group, hydroxy group, hydroxy hydrocarbyl group, acyl group, acyloxy group, amino group, hydrocarbylamino group, hydrocarbyloxy group, silyl group, hydrocarbylsilyl group, imino group-containing hydrocarbyl group and imino group-containing hydrocarbylamino group, or a divalent hydrocarbon chain or a single bond which is unsubstituted or substituted by a halogen atom, hydroxy group or amino group, where different silicon atoms are unbound or bound to form a cyclic structure,
L 1 is a connecting group selected from single bond, oxy group, imide bond, imino group, carbonyl group, carbonyloxy group and unsaturated bond, and hydrocarbon chain that may contain them, where said connecting group may contain an alicycle, an aromatic ring, or a hetero ring,
n1 is the number indicating degree of polymerization and exceeding 0,

a polysilazane represented by the formula (2)

wherein each R 21 is hydrogen, and
which has a mass average molecular weight 1,000 to 10,000 and
an organic solvent and
wherein 0.1 to 8 parts by mass of said silicon compound is contained per 100 parts by mass of said polysilazane.

2. The composition for forming a coating film according to claim 1 , wherein said organic solvent comprises one or more kinds of solvent that is aromatic hydrocarbon, saturated hydrocarbon compound, alicyclic hydrocarbon and alkylether.

3. The composition for forming a coating film according to claim 1 , wherein said silicon compound is represented by the following formula (1A):

wherein
R 1A s are monovalent groups independently selected from the group consisting of hydrogen, halogen atom, hydroxy group, alkyl group, cycloalkyl group, alkoxy group, aryl group, aralkyl group, acyl group, acyloxy group, alkyl amino group, amino group, silyl group and alkylsilyl group, or R 1A s are a single bond where different silicon atoms are unbound or bound to form a cyclic structure and
n1A is the number indicating degree of polymerization and exceeding 1.

4. The composition for forming a coating film according to claim 3 , wherein said R 1A s are groups independently selected from the group consisting of alkyl group, alkoxy group, silyl group, silylalkyl group and alkylsilyl group.

5. The composition for forming a coating film according to claim 3 , wherein said R 1A s are groups independently selected from the group consisting of alkyl group of 1 to 4 carbon atoms, alkoxy group of 1 to 3 carbon atoms and alkylsilyl group of 1 to 3 carbon atoms.

6. The composition for forming a coating film according to claim 3 , wherein said R 1A s are independently selected from the group consisting of methyl group, ethyl group, t-butyl group, trimethylsilyl group, methoxy group and ethoxy group.

7. The composition for forming a coating film according to claim 3 , wherein n1A is 1 or more and 6 or less.

8. The composition for forming a coating film according to claim 1 , wherein said silicon compound is represented by the following formula (1B):

wherein
R 1B s are monovalent groups independently selected from the group consisting of alkyl group, cycloalkyl group, aryl group, aryloxy group, heteroaryl group, aralkyl group, alkenyl group, alkynyl group, hydroxy group, hydroxyalkyl group, hydroxyalkenyl group, acyl group, acyloxy group, alkylamino group, alkyloxy group, silyl group and alkylsilyl group,
L 1B is a connecting group selected from single bond, imide bond, imino group, carbonyl group, carbonyloxy group, unsaturated bond, and hydrocarbon chain, and
n1B is the number indicating degree of polymerization and exceeding 0, and

at least one of R 1B and L 1B contains an ethylene bond or an acetylene bond.

9. The composition for forming a coating film according to claim 8 , wherein at least one R 1B is a monovalent group selected from the group consisting of ethynyl group and vinyl group.

10. The composition for forming a coating film according to claim 8 , wherein L 1B is selected from the group consisting of single bond and imino group, and hydrocarbon chain, and at least one R 1B is a monovalent group selected from the group consisting of ethynyl group and vinyl group.

11. The composition for forming a coating film according to claim 8 , wherein n1B is one or more, L 1B is imino group, and two R 1B at both terminals of the molecular chain contain each an ethylene bond or an acetylene bond.

12. The composition for forming a coating film according to claim 8 , wherein said silicon compound has a mass-average molecular weight of 50 to 200,000.

13. The composition for forming a coating film according to claim 1 , wherein said silicon compound is represented by the following formula (1C):

wherein
R 1C s are monovalent groups independently selected from the group consisting of alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, arylamino group, hydroxy group, hydroxyalkyl group, acyl group, acyloxy group, amino group, alkylamino group, alkyloxy group, silyl group and alkylsilyl group,
L 1C is a connecting group selected from alkylene group and arylene group that contain or do not contain oxy group, and
n1C is the number indicating degree of polymerization and exceeding 1, and

none of R 1C s and L 1C contains an ethylene bond or an acetylene bond.

14. The composition for forming a coating film according to claim 13 , wherein said L 1C is selected from the group consisting of 1,2-ethanedioxy group, 1,4-butanedioxy group, 1,6-hexanedioxy group, 1,4-cyclohexanedioxy group, phenylenedioxy group, bis(2-oxyethyl)ether group, ethylene group, tetramethylene group, hexamethylene group and phenylene group.

15. The composition for forming a coating film according to claim 13 , wherein n1C is 1.

16. The composition for forming a coating film according to claim 1 , wherein said silicon compound is represented by the following formula (1D):

wherein
R 1D s are monovalent groups independently selected from the group consisting of alkyl group, aryl group, alkylamino group, arylamino group, imino group-containing alkyl group and imino group-containing alkylamino group, where the number of hydrogen atom bound to each silicon atom is 1 or less and the total number of carbon atoms and nitrogen atoms contained in all R 1D is 8 or more.

17. The composition for forming a coating film according to claim 16 , wherein said R 1D is selected from the group consisting of alkyl group of 1 to 10 carbon atoms, aryl group of 6 to 12 carbon atoms, alkylamino group of 1 to 10 carbon atoms, arylamino gr

Assignees

• Az Electronic Mat Luxembourg Sarl
• Merck Patent Gmbh

Inventors

• Kawato Shunji
• Ozaki Yuki
• SATAKE Noboru
• Kobayashi Masakazu
• Endo Hironori

Classifications

• C08L2201/14

  Gas barrier composition · CPC title

• C08J2383/16

  in which all the silicon atoms are connected by linkages other than oxygen atoms · CPC title

• C08J3/28

  Treatment by wave energy or particle radiation · CPC title

• C08L2203/16

  used for films · CPC title

• C08K5/5445

  containing at least one Si-N bond · CPC title