# US 9,434,856 B2 · Film-forming composition and embedding material

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- Number: US 9,434,856 B2
- Document ID: US9434856B2
- Status: Granted
- Kind: B2
- Application number: 14/400,258
- Filed: 2013-05-10
- Published: 2015-04-02
- Granted: 2016-09-06
- Earliest claimed: 2012-05-11
- Assignees: Nissan Chemical Industries, Ltd.
- Applicants: Nissan Chemical Industries, Ltd.
- Inventors: Naoya Nishimura; Takahiro Kaseyama; Masaaki Ozawa
- Web page: https://patentgrep.com/patent/US9434856B2

## CPC

- C09D 179/04: Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08G 73/026: {Wholly aromatic polyamines}
- C08G 73/0273: {Polyamines containing heterocyclic moieties in the main chain}
- C08G 73/0644: {Poly(1,3,5)triazines}
- C09D 4/00: Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16}
- C09D 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- H10K 85/111: {comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene}
- H10K 85/151: {Copolymers}
- H10K 50/85: Arrangements for extracting light from the devices
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

Provided is a film-forming composition containing organic monomers represented by formula (A) that are capable of providing triazine ring-containing polymers, crosslinking agents, and linear polymers, which contain a repeating unit structure represented by formula (1). Thus, a film-forming composition that is suitable as an embedding material can be provided, said film-forming composition: including triazine ring-containing polymers that are capable of achieving, by polymer alone, high heat resistance, high transparency, a high refractive index, high solubility and low volume shrinkage; and is capable of minimizing occurrences of cracks when embedding films are manufactured. Furthermore, a solvent-free film-forming composition that does not contain any solvents conducive to organic electroluminescent film degradation, can be cured at a low temperature, and is suitable for forming top-emission type organic electroluminescent elements, can be provided.

## Claims

### Claim 1

A film-forming composition comprising:
(A) a triazine ring-containing polymer which comprises a recurring unit structure of formula (1) below:
wherein R and R′ are each independently a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or an aralkyl group; and Ar is at least one moiety selected from the group consisting of moieties of formulas (2) to (13) below:
wherein R1 to R92 are each independently a hydrogen atom, a halogen atom, a carboxyl group, a sulfone group, an alkyl group of 1 to 10 carbons, or an alkoxy group of 1 to 10 carbons; R93 and R94 are hydrogen atoms or alkyl groups of 1 to 10 carbons; W1 and W2 are each independently a single bond, CR95R96 (wherein R95 and R96 are each independently a hydrogen atom or an alkyl group of 1 to 10 carbons, with the proviso that R95 and R96 may together form a ring), C═O, O, S, SO, SO2 or NR97 (wherein R97 is a hydrogen atom or an alkyl group of 1 to 10 carbons); and X1 and X2 are each independently a single bond, an alkylene group of 1 to 10 carbons, or a group of formula (14) below:
wherein R98 to R101 are each independently a hydrogen atom, a halogen atom, a carboxyl group, a sulfone group, an alkyl group of 1 to 10 carbons, or an alkoxy group of 1 to 10 carbons; and Y1 and Y2 being each independently a single bond or an alkylene group of 1 to 10 carbons;
(B) a crosslinking agent; and
1 to 200 parts by weight of (C) an organic monomer capable of providing a linear polymer, wherein the organic monomer is a compound of formula (A) below
wherein R102 and R104 are each independently a hydrogen atom, an alkyl group of 1 to 10 carbons or a polymerizable carbon-carbon double bond-containing group; and R103 being a hydrogen atom or an alkyl group of 1 to 10 carbons, with the proviso that either of R102 and R104 is a polymerizable carbon-carbon double bond-containing group but R102 and R104 are not both at the same time polymerizable carbon-carbon double bond-containing groups, per 100 parts by weight of said triazine-ring containing polymer (A),
wherein said film-forming composition is solvent-free.

### Claim 2 (depends on 1)

The film-forming composition of claim 1, wherein R102 and R103 in formula (A) are both hydrogen atoms and R104 is a polymerizable carbon-carbon double bond-containing group.

### Claim 3 (depends on 1, 2)

The film-forming composition of claim 1 or 2, wherein the organic monomer is N-vinylformamide.

### Claim 4 (depends on 1)

The film-forming composition of claim 1, wherein the crosslinking agent is a polyfunctional epoxy compound and/or a polyfunctional (meth)acrylic compound.

### Claim 5 (depends on 4)

The film-forming composition of claim 4, wherein the crosslinking agent is a polyfunctional (meth)acrylic compound.

### Claim 6 (depends on 5)

The film-forming composition of claim 5, wherein the polyfunctional (meth)acrylic compound is a compound which at 25° C. is liquid and has a viscosity of 5,000 mPa·s or less.

### Claim 7 (depends on 1)

The film-forming composition of claim 1, wherein the crosslinking agent is a polyfunctional epoxy compound, a polyfunctional vinyl ether compound or a polyfunctional allyl ether compound.

### Claim 8 (depends on 7)

The film-forming composition of claim 7, wherein the crosslinking agent is a polyfunctional allyl ether compound.

### Claim 9 (depends on 1)

An embedding material composed of the film-forming composition of claim 1.

### Claim 10 (depends on 9)

An embedding film obtained from the embedding material of claim 9.

### Claim 11 (depends on 10)

An electronic device comprising the embedding film of claim 10.

### Claim 12

A cured film obtained by curing a solvent-free film-forming composition comprising:
(A) a triazine ring-containing polymer which comprises a recurring unit structure of formula (1) below:
wherein R and R′ are each independently a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or an aralkyl group; and Ar is at least one moisety selected from the group consisting of moieties of formulas (2) to (13) below:
wherein R1 to R92 are each independently a hydrogen atom, a halogen atom, a carboxyl group, a sulfone group, an alkyl group 1 to 10 carbons, or an alkoxy group of 1 to 10 carbons; R93 and R94 R are hydrogen atoms or alkyl groups of 1 to 10 carbons; W1 and W2 are each independently a single bond, CR95R96 (wherein R95 and R96 are each independently a hydrogen atom or an alkyl group of 1 to 10 carbons, with the proviso that R95 and R96 may together form a ring), C═O, O, S, SO, SO2 or NR97 (wherein R97 is a hydrogen atom or an alkyl group of 1 to 10 carbons); and X1 and X2 are each independently a single bond, an alkylene group of 1 to 10 carbons, or a group of formula (14) below:
wherein R98 to R101 are each independently a hydrogen atom, a halogen atom, a carboxyl group, a sulfone group, an alkyl group of 1 to 10 carbons, or an alkoxy group of 1 to 10 carbons; and Y1 and Y2 being each independently a single bond or an alkylene group of 1 to 10 carbons;
(B) a crosslinking agent; and
1 to 200 parts by weight of (C) an organic monomer capable of providing a linear polymer, wherein the organic monomer is a compound of formula (A) below
wherein R102 and R104 are each independently a hydrogen atom, an alkyl group of 1 to 10 carbons or a polymerizable carbon-carbon double bond-containing group; and R103 being a hydrogen atom or an alkyl group of 1 to 10 carbons, with the proviso that either one of R102 and R104 is a polymerizable carbon-carbon double bond-containing group but R102 and R104 are not both at the same time polymerizable carbon-carbon double bond-containing groups, per 100 parts by weight of said triazine-ring containing polymer (A).

### Claim 13 (depends on 12)

An electronic device comprising the cured film of claim 12.

### Claim 14

A top emission-type organic electroluminescence device comprising a cured film obtained by curing a solvent-free film-forming composition comprising:
(A) a triazine ring-containing polymer which comprises a recurring unit structure of formula (1) below:
wherein R and R′ are each independently a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or an aralkyl group; and Ar is at least one moiety selected from the group consisting of moieties of formulas (2) to (13) below:
wherein R1 to R92 are each independently a hydrogen atom, a halogen atom, a carboxyl group, a sulfone group, an alkyl group of 1 to 10 carbons, or an alkoxy group of 1 to 10 carbons; R93 and R94 are hydrogen atoms or alkyl groups of 1 to 10 carbons; W1 and W2 are each independently a single bond, CR95R96 (wherein R95 and R96 are each independently a hydrogen atom or an alkyl group of 1 to 10 carbons, with the proviso that R95 and R96 may together form a ring), C═O, O, S, SO, SO2 or NR97 (wherein R97 is a hydrogen atom or an alkyl group of 1 to 10 carbons); and X1 and X2 are each independently a single bond, an alkylene group of 1 to 10 carbons, or a group of formula (14) below:
wherein R98 to R101 are each independently a hydrogen atom, a halogen atom, a carboxyl group, a sulfone group, an alkyl group of 1 to 10 carbons, or an alkoxy group of 1 to 10 carbons; and Y1 and Y2 being each independently a single bond or an alkylene group of 1 to 10 carbons;
(B) a crosslinking agent; and
1 to 200 parts by weight of (C) an organic monomer capable of providing a linear polymer, wherein the organic monomer is a compound of formula (A) below
wherein R102 and R104 are each independently a hydrogen atom, an alkyl group of 1 to 10 carbons or a polymerizable carbon-carbon double bond-containing group; and R103 being a hydrogen atom or an alkyl group of 1 to 10 carbons, with the proviso that either one of R102 and R104is a polymerizable carbon-carbon double bond-containing group but R102 and R104 are not both at the same time polymerizable carbon-carbon double bond-containing groups, per 100 parts by weight of said triazine-ring containing polymer (A).
