# US 12,216,405 B2 · Photosensitive resin composition, photosensitive resin film, photosensitive dry film, patterning process, and light emitting device

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- Number: US 12,216,405 B2
- Document ID: US12216405B2
- Status: Granted
- Kind: B2
- Application number: 17/778,203
- Filed: 2020-11-12
- Published: 2023-02-02
- Granted: 2025-02-04
- Earliest claimed: 2019-12-03
- Assignees: Shin-Etsu Chemical Co., Ltd.
- Applicants: Shin-Etsu Chemical Co., Ltd.
- Inventors: Hitoshi Maruyama; Tamotsu Oowada
- Web page: https://patentgrep.com/patent/US12216405B2

## CPC

- G03F 7/0757: {Macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence)}
- C08G 77/20: containing silicon bound to unsaturated aliphatic groups
- G03F 7/0047: {characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing}
- G03F 7/105: having substances, e.g. indicators, for forming visible images
- G03F 7/40: Treatment after imagewise removal, e.g. baking
- B82Y 30/00: Nanotechnology for materials or surface science, e.g. nanocomposites
- C08G 77/50: by carbon linkages
- C08G 77/52: containing aromatic rings
- C08G 77/54: Nitrogen-containing linkages
- C09D 183/14: in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C09D183/10 takes precedence)
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- 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)

## Abstract

A photosensitive resin composition containing (A) an acid-crosslinkable group-containing silicone resin, (B) a photo-acid generator, and (C) quantum dot particles. Thus, a photosensitive resin composition is capable of easily forming a film having favorable heat resistance, lithography resolution, and luminous properties; a photosensitive resin film and a photosensitive dry film are obtained by using the photosensitive resin composition; patterning processes use these; and a light emitting device is obtained by using the photosensitive resin composition.

## Claims

### Claim 1

A photosensitive resin composition comprising:
(A) an acid-crosslinkable group-containing silicone resin;
(B) a photo-acid generator; and
(C) quantum dot particles,
wherein,
the component (A) comprises a silicone resin containing a repeating unit represented by any of the following formulae (A1) to (A6),
wherein R1 to R4 each independently represent a monovalent hydrocarbon group having 1 to 20 carbon atoms optionally containing a heteroatom; each “m” independently represents an integer of 1 to 600, and when “m” is an integer of 2 or more, R3's are identical to or different from one another, and R4's are identical to or different from one another; “a”, “b”, “c”, “d”, “e”, and “f”' represent numbers satisfying 0≤a≤1, 0 ≤b≤1, 0≤c≤1,0≤d≤1,0≤e≤1,0≤f≤1, 0<c+d+e+f≤1, and a+b+c+d+e+f=1; each X1 represents a divalent group shown by the following formula (X1); each X2 represents a divalent group shown by the following formula (X2); and each X3 represents a divalent group shown by the following formula (X3),
wherein R11 to R14 each independently represent a monovalent hydrocarbon group having 1 to 20 carbon atoms optionally containing a heteroatom; “p” represents an integer of 1 to 600, and when “p” is an integer of 2 or more, R13's are identical to or different from one another, and R14's are identical to or different from one another; R15 and R16 each independently represent a hydrogen atom or a methyl group; and each “x” independently represents an integer of 0 to 7,
wherein Y1 represents a single bond, a methylene group, a propane-2,2-diyl group, a 1,1,1,3,3,3-hexafluoropropane-2,2-diyl group, or a fluorene-9,9-diyl group; R21 and R22 each independently represent an alkyl or alkoxy group having 1 to 4 carbon atoms; “g” and “h” each independently represent 0, 1, or 2, when “g” is 2, R21's are identical to or different from one another, and when “h” is 2, R22's are identical to or different from one another; R23 and R24 each independently represent a hydrogen atom or a methyl group; and each “y” independently represents an integer of 0 to 7, and
wherein R31 and R32 each independently represent a hydrogen atom or a methyl group; each “z” independently represents an integer of 0 to 7; and R33 represents a monovalent hydrocarbon group having 1 to 8 carbon atoms optionally containing an ester bond or an ether bond, or a monovalent group shown by the following formula (X3-1),
wherein R34 represents a divalent hydrocarbon group having 1 to 8 carbon atoms optionally containing an ester bond or an ether bond.

### Claim 2 (depends on 1)

The photosensitive resin composition according to claim 1, wherein the quantum dot particles (C) comprise red quantum dot particles or green quantum dot particles.

### Claim 3 (depends on 1)

The photosensitive resin composition according to claim 1, wherein the quantum dot particles (C) are composed of a II-VI semiconductor compound; a III-V semiconductor compound; a IV-VI semiconductor compound; a group IV element or a compound containing a group IV element; or a combination thereof.

### Claim 4 (depends on 2)

The photosensitive resin composition according to claim 2, wherein the quantum dot particles (C) are composed of a II-VI semiconductor compound; a III-V semiconductor compound; a IV-VI semiconductor compound; a group IV element or a compound containing a group IV element; or a combination thereof.

### Claim 5 (depends on 1)

The photosensitive resin composition according to claim 1, wherein the quantum dot particles (C) is contained in an amount of 3 to 80 mass % based on a total solid content of the photosensitive resin composition.

### Claim 6 (depends on 2)

The photosensitive resin composition according to claim 2, wherein the quantum dot particles (C) is contained in an amount of 3 to 80 mass % based on a total solid content of the photosensitive resin composition.

### Claim 7 (depends on 3)

The photosensitive resin composition according to claim 3, wherein the quantum dot particles (C) is contained in an amount of 3 to 80 mass % based on a total solid content of the photosensitive resin composition.

### Claim 8 (depends on 1)

The photosensitive resin composition according to claim 1, further comprising (D) a crosslinking agent.

### Claim 9 (depends on 1)

The photosensitive resin composition according to claim 1, further comprising (E) an antioxidant.

### Claim 10 (depends on 1)

The photosensitive resin composition according to claim 1, further comprising (F) a solvent.

### Claim 11 (depends on 1)

A photosensitive resin film comprising a dried product of the photosensitive resin composition according to claim 1.

### Claim 12 (depends on 11)

A photosensitive dry film comprising:
a support film; and
the photosensitive resin film according to claim 11 on the support film.

### Claim 13 (depends on 1)

A patterning process comprising steps of:
(i) applying the photosensitive resin composition according to claim 1 onto a substrate to form a photosensitive resin film on the substrate;
(ii) exposing the photosensitive resin film to light; and
(iii) developing the exposed photosensitive resin film with a developer to dissolve and remove an unexposed portion for patterning.

### Claim 14 (depends on 12)

A patterning process comprising steps of:
(i′) forming a photosensitive resin film on a substrate by using the photosensitive dry film according to claim 12;
(ii) exposing the photosensitive resin film to light; and
(iii) developing the exposed photosensitive resin film with a developer to dissolve and remove an unexposed portion for patterning.

### Claim 15 (depends on 13)

The patterning process according to claim 13, further comprising (iv) a step of post-curing the resin film patterned by the development, the post-curing being performed at a temperature of 100 to 250° C.

### Claim 16 (depends on 14)

The patterning process according to claim 14, further comprising (iv) a step of post-curing the resin film patterned by the development, the post-curing being performed at a temperature of 100 to 250° C.

### Claim 17 (depends on 11)

A light emitting device comprising the photosensitive resin film according to claim 11.

### Claim 18 (depends on 1)

The photosensitive resin composition according to claim 1, wherein “a”, “c”, and “e” in the formulae (A1), (A3) and (A5) represent numbers satisfying 0.2≤a+c+e≤0.95.

### Claim 19 (depends on 1)

The photosensitive resin composition according to claim 1, wherein “a”, “b”, “c”, “d”, “e”, and “f” in the formulae (A1) to (A6) represent numbers satisfying 0.2≤a+c+e≤0.95, 0.05≤b+d+f≤0.8, 0≤a+b≤0.9, 0≤c+d≤0.7, and 0<e+f≤1.