# US 2021/0240077 A1 · Photosensitive compositions, preparation methods thereof, and quantum dot polymer composite pattern produced therefrom

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- Number: US 2021/0240077 A1
- Document ID: US20210240077A1
- Status: Published application
- Kind: A1
- Application number: 17/234,126
- Filed: 2021-04-19
- Published: 2021-08-05
- Earliest claimed: 2015-12-17
- Assignees: Samsung Electronics Co., Ltd.; Samsung SDI Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.; Samsung SDI Co., Ltd.
- Inventors: Shang Hyeun PARK; Hojeong PAEK; Jonggi KIM; Nayoun WON; Shin Ae JUN
- Web page: https://patentgrep.com/patent/US20210240077A1

## CPC

- G03F 7/0043: {Chalcogenides; Silicon, germanium, arsenic or derivatives thereof; Metals, oxides or alloys thereof (G03F7/0044 takes precedence)}
- C09K 11/02: Use of particular materials as binders, particle coatings or suspension media therefor
- C09K 11/08: containing inorganic luminescent materials
- C09K 11/883: {with zinc or cadmium}
- G02B 5/207: {comprising semiconducting materials}
- G02B 5/223: {containing organic substances, e.g. dyes, inks or pigments}
- G03F 7/0007: {Filters, e.g. additive colour filters; Components for display devices}
- G03F 7/0047: {characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing}
- G03F 7/027: Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence)
- G03F 7/029: Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
- G03F 7/031: Organic compounds not covered by group G03F7/029
- G03F 7/033: the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
- 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)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS

## Abstract

A photosensitive composition including: a plurality of quantum dots, wherein the quantum dot includes an organic ligand bound to a surface of the quantum dot; a photoinitiator; a binder including a carboxylic acid group; a photopolymerizable monomer having a carbon-carbon double bond; and a solvent, wherein the photoinitiator includes a first photoinitiator including an oxime compound and a second photoinitiator including at least one selected from a phosphine oxide compound and an amino ketone compound.

## Claims

### Claim at position 1

-19. (canceled)

### Claim 20

A color filter comprising a substrate and a quantum dot-polymer composite pattern disposed on the substrate,
wherein the quantum dot-polymer composite pattern comprises a first quantum dot polymer composite,
wherein the first quantum dot polymer composite is configured to emit a first light and comprises a polymerization production of a first photosensitive composition comprising:
a plurality of first quantum dots being configured to emit the first light;
a photoinitiator system; and
a photopolymerizable monomer comprising a carbon-carbon double bond,
wherein the photoinitiator system comprises a first photoinitiator comprising an oxime compound and a second photoinitiator comprising a phosphine oxide compound, an amino ketone compound, or a combination thereof, and
wherein the first photosensitive composition further comprises a reactive compound comprising at least two thiol groups and represented by Chemical Formula 2:
wherein in Chemical Formula 2,
R1 is selected from hydrogen; a substituted or unsubstituted C1 to C30 linear or branched alkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C3 to C30 heteroaryl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C3 to C30 heterocycloalkyl group; a C1 to C10 alkoxy group; a hydroxy group; —NH2; a substituted or unsubstituted C1 to C30 amine group (—NRR′, wherein R and R′ are each independently hydrogen or a C1 to C30 linear or branched alkyl group); an isocyanate group; a halogen; —ROR′ (wherein R is a substituted or unsubstituted C1 to C20 alkylene group and R′ is hydrogen or a C1 to C20 linear or branched alkyl group); acyl halide (—RC(═O)X, wherein R is a substituted or unsubstituted alkylene group and X is a halogen); —C(═O)OR′ (wherein R′ is hydrogen or a C1 to C20 linear or branched alkyl group); —CN; or —C(═O)ONRR′ (wherein R and R′ are each independently hydrogen or a C1 to C20 linear or branched alkyl group),
L1 is a carbon atom, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C6 to C30 heteroarylene group, wherein at least one of non-adjacent methylene (—CH2-) groups of the substituted C1 to C30 alkylene group is replaced by a sulfonyl group (—SO2—), a carbonyl group (—CO—), an ether group (—O—), a sulfide group (—S—), a sulfoxide group (—SO—), an ester group (—C(═O)O—), an amide group (—C(═O)NR—) (wherein R is hydrogen or a C1 to C10 alkyl group), or a combination thereof,
Y1 is a single bond; a substituted or unsubstituted C1 to C30 alkylene group; a substituted or unsubstituted C2 to C30 alkenylene group; a substituted C1 to C30 alkylene group or a C2 to C30 alkenylene group wherein at least one methylene (—CH2-) group is replaced by a sulfonyl group (—S(═O)2—), a carbonyl group (—C(═O)—), an ether group (—O—), a sulfide group (—S—), a sulfoxide group (—S(═O)—), an ester group (—C(═O)O—), an amide group (—C(═O)NR—) (wherein R is hydrogen or a C1 to C10 linear or branched alkyl group), an imine group (—NR—) (wherein R is hydrogen or a C1 to C10 linear or branched alkyl group) or a combination thereof,
m is an integer of 1 or more,
k1 is 0 or an integer of 1 or more,
k2 is an integer of 1 or more, and
a sum of m and k2 is an integer of 3 or more,
provided that when Y1 is not a single bond, m does not exceed the valence of Y1, and provided that a sum of k1 and k2 does not exceed the valence of L1,
wherein a weight ratio of the first photoinitiator and the second photoinitiator is about 1:1 to 1:0.1;
wherein an amount of the first quantum dots is greater than or equal to about 10 weight % and an amount of the reactive compound is greater than 10 weight % and less than or equal to about 40 weight %, based on a total weight of the first photosensitive composition.

### Claim 21 (depends on 20)

The color filter of claim 20, wherein the first quantum dot polymer composite further comprises a polymer comprising a carboxylic acid group.

### Claim 22 (depends on 20)

The color filter of claim 20, wherein the amount of the first quantum dots is greater than or equal to about 12 weight % based on a total weight of the first photosensitive composition.

### Claim 23 (depends on 20)

The color filter of claim 20, wherein in the first photosensitive composition, the amount of the reactive compound is greater than or equal to about 15 weight % based on a total weight of the first photosensitive composition.

### Claim 24 (depends on 20)

The color filter of claim 20, wherein the first quantum dots emit red light or green light.

### Claim 25 (depends on 20)

The color filter of claim 20, wherein the quantum dot-polymer composite pattern further comprises a second quantum dot polymer composite disposed on the substrate and separately from the first quantum dot polymer composite, and
wherein the second quantum dot polymer composite is configured to emit a second light different from the first light and comprises a polymerization production of a second photosensitive composition comprising:
a plurality of second quantum dots being configured to emit the second light;
the photoinitiator system comprising the first photoinitiator and the second photoinitiator; and
the photopolymerizable monomer,
wherein the second photosensitive composition further comprises the reactive compound,
wherein in the second photosensitive composition, a weight ratio of the first photoinitiator and the second photoinitiator is about 1:1 to 1:0.1;
wherein an amount of the second quantum dots is greater than or equal to about 10 weight % and an amount of the reactive compound is greater than 10 weight % and less than or equal to about 40 weight %, based on a total weight of the second photosensitive composition.

### Claim 26 (depends on 25)

The color filter of claim 25, wherein the second quantum dots emit green light or red light.

### Claim 27 (depends on 20)

The color filter of claim 20, wherein the first quantum dot polymer composite is configured to maintain a blue light photoconversion rate of greater than or equal to about 40% of an initial value thereof after being exposed to light, developed, and heated at 180° C. for 30 minutes.

### Claim 28 (depends on 20)

The color filter of claim 20, wherein the plurality of the first quantum dots comprises a organic ligand and the organic ligand comprises RCOOH, RNH2, R2NH, R3N, RSH, R3PO, R3P, ROH, RCOOR′, RPO(OH)2, R2POOH (wherein R and R′ are each independently a C5 to C24 aliphatic hydrocarbon group or a C6 to C20 aromatic hydrocarbon group), a polymer organic ligand, or a combination thereof.

### Claim 29 (depends on 20)

The color filter of claim 20, wherein the first quantum dots comprises a Group II-VI compound, a Group III-V compound, a Group compound, a Group I-II-IV-VI compound, or a combination thereof.

### Claim 30 (depends on 20)

The color filter of claim 20, wherein the oxime compound comprises an arylthioaryl group, an acyl group RC(═O)— (wherein R is a C1 to C30 alkyl group, a C6 to C30 aryl group, or a C6 to C30 cycloalkyl group), C3 to C30 cycloalkyl group, an alkanedione group, or a combination thereof,
wherein the aminoketone compound comprises a dialkylamino group, a morpholinylphenyl group, an acetophenone group, or a combination thereof, and
wherein the phosphine oxide compound comprises acylphosphine oxide.

### Claim 31 (depends on 28)

The color filter of claim 28, wherein the oxime compound is an oxime compound having an arylthioaryl moiety,
wherein the aminoketone compound comprises 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one, and
wherein the phosphine oxide compound comprises a mixture of monoacyl phosphine oxide compound and a bisacylphosphine oxide compound.

### Claim 32 (depends on 20)

The color filter of claim 20, wherein the reactive compound comprises ethoxylated pentaerythritol tetra(3-mercaptopropionate), trimethylolpropanetri(3-mercaptopropionate), trimethylolpropanetri(3-mercaptoacetate), glycol di-3-mercaptopropionate, polypropylene glycol di-3-mercaptopropionate, ethoxylated trimethylpropane tri(3-mercaptopropionate), glycol dimercaptoacetate, ethoxylated glycol dimercaptoacetate, 1,4-bis(3-mercaptobutyryloxy)butane, trimethylolpropanetris(3-mercaptopropionate), tris[2-(3-mercaptopropinonyloxy)ethyl]isocyanurate, 1,3,5-tris(3-mercaptobutyloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), 1,6-hexanedithiol, 1,3-propanedithiol, 1,2-ethanedithiol, polyethylene glycol dithiol comprising 1 to 10 ethylene glycol structural units, or a combination thereof.

### Claim 33 (depends on 20)

The color filter of claim 20, wherein the reactive compound comprises a dithiol compound and the first photosensitive composition does not comprise a trithiol compound, a tetrathiol compound, or a combination thereof.

### Claim 34 (depends on 20)

The color filter of claim 20, wherein the first quantum dot composite further comprises a light diffusing agent selected from a metal oxide particle, a metal particle, or a combination thereof.

### Claim 35 (depends on 34)

The color filter of claim 34, wherein the light diffusing agent comprises a titanium oxide particle.

### Claim 36 (depends on 20)

A display device comprising a color filter of claim 20.