# US 2014/0197387 A1 · Nanocomposite, method of preparing the same, and surface light emitting device using the same

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- Number: US 2014/0197387 A1
- Document ID: US20140197387A1
- Status: Published application
- Kind: A1
- Application number: 14/079,959
- Filed: 2013-11-14
- Published: 2014-07-17
- Earliest claimed: 2012-11-14
- Assignees: Samsung Electronics Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.
- Inventors: Hiroshi MIYAO; Tadao YAGI; Ryuichi SATOH
- Web page: https://patentgrep.com/patent/US20140197387A1

## CPC

- C08J 5/005: {Reinforced macromolecular compounds with nanosized materials, e.g. nanoparticles, nanofibres, nanotubes, nanowires, nanorods or nanolayered materials}
- C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
- C08G 2261/5222: electrofluorescent
- C08G 2261/95: Use in organic luminescent diodes
- C08J 2379/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C09C 1/3669: {Treatment with low-molecular organic compounds}
- C09C 1/3684: {Treatment with organo-silicon compounds}
- C09C 3/08: Treatment with low-molecular-weight {non-polymer} organic compounds {(C09C3/006, C09C3/048 take precedence)}
- C09C 3/12: Treatment with organosilicon compounds {(C09C3/006 takes precedence)}
- H10K 50/854: comprising scattering means
- H10K 50/858: comprising refractive means, e.g. lenses
- H10K 2102/331: {Nanoparticles used in non-emissive layers, e.g. in packaging layer}
- Y02E 10/549: Organic PV cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09C: TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES (treatment of materials specially adapted to enhance their filling properties in mortars, concrete or artificial stone C04B14/00, C04B18/00, C04B20/00); PREPARATION OF CARBON BLACK {; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Provided is a nanocomposite including a matrix resin including a polyimide, and a surface-modified inorganic oxide nanoparticle dispersed in the matrix, wherein the surface-modified inorganic oxide nanoparticle includes an inorganic oxide nanoparticle, a first functional group modifying a surface of the inorganic oxide nanoparticle and having an imide backbone, and a second functional group modifying a surface of the inorganic oxide nanoparticle and binding to the matrix resin.

## Claims

### Claim 1

A nanocomposite comprising:
a matrix resin including a polyimide;
and a surface-modified inorganic oxide nanoparticle dispersed in the matrix, wherein the surface-modified inorganic oxide nanoparticle includes
an inorganic oxide nanoparticle;
a first functional group modifying a surface of the inorganic oxide nanoparticle and having an imide backbone; and
a second functional group modifying a surface of the inorganic oxide nanoparticle and binding to the matrix resin.

### Claim 2 (depends on 1)

The nanocomposite of claim 1, wherein the second functional group comprises an epoxy group.

### Claim 3 (depends on 1)

The nanocomposite of claim 1, wherein the vol % of the inorganic oxide nanoparticle based on the total nanocomposite is from about 30 to about 60 vol %.

### Claim 4 (depends on 1)

The nanocomposite of claim 1, wherein the mean particle diameter of the inorganic oxide nanoparticle measured by direct observation method is in a range from about 2 nanometers to about 100 nanometers.

### Claim 5 (depends on 1)

The nanocomposite of claim 1, wherein the inorganic oxide nanoparticle comprises at least one oxide selected from titanium oxide, zirconium oxide, and barium titanium acid.

### Claim 6 (depends on 5)

The nanocomposite of claim 5, wherein the inorganic oxide nanoparticle comprises a rutile titanium oxide.

### Claim 7

A method of preparing a nanocomposite comprising:
modifying a surface of an inorganic oxide nanoparticle with a silane coupling agent having an amino group, represented by General Formula 1, or a phosphate ester compound having an amino group, represented by General Formula 2;
imidizing at least a portion of the amino groups to produce an inorganic oxide nanoparticle having a surface modified with a first functional group having an imide backbone,
modifying the surface of the inorganic oxide nanoparticle with a second functional group to obtain a surface-modified inorganic oxide nanoparticle comprising the inorganic oxide nanoparticle and the first functional group and the second functional group modifying the surface of the inorganic oxide nanoparticle; and
mixing the surface-modified inorganic oxide nanoparticle with a polyamic acid and treating with heat the resulting mixture of the surface-modified inorganic oxide nanoparticle and the polyamic acid
wherein,
in General Formula 1, R1 is a substituted or unsubstituted C1 through C10 alkylene group, a substituted or unsubstituted C6 through C20 arylene group, or a substituted or unsubstituted C4 through C20 heteroarylene group, R2 is a hydrogen atom or a substituted or unsubstituted C1 through C10 alkyl group, R3 is a substituted or unsubstituted C1 through C10 alkyl group or a substituted or unsubstituted C1 through C10 alkoxy group, and R4 is a substituted or unsubstituted C1 through C10 alkyl group, and
in General Formula 2, R5 is a substituted or unsubstituted C1 through C10 alkylene group, a substituted or unsubstituted C6 through C20 arylene group, or a substituted or unsubstituted C4 through C20 heteroarylene group, and R6 is a substituted or unsubstituted C1 through C10 alkyl group.

### Claim 8

A method of preparing a nanocomposite comprising:
imidizing at least a portion of amino groups included in a silane coupling agent, represented by General Formula 1, or a phosphate ester compound, represented by General Formula 2, to obtain a silane coupling agent or a phosphate ester compound having an imide backbone;
binding the silane coupling agent or the phosphate ester compound having an imide backbone to a surface of an inorganic oxide nanoparticle to obtain an inorganic oxide nanoparticle having a surface modified with a first functional group having the imide backbone;
modifying the surface of the inorganic oxide nanoparticle with a second functional group having an epoxy group to obtain a surface-modified inorganic oxide nanoparticle comprising the inorganic oxide nanoparticle and the first functional group and the second functional group modifying the surface of the inorganic oxide nanoparticle; and
mixing the surface-modified inorganic oxide nanoparticle with a polyamic acid and treating with heat the resulting mixture of the surface-modified inorganic oxide nanoparticle and the polyamic acid
wherein
in General Formula 1, R1 is a substituted or unsubstituted C1 through C10 alkylene group, a substituted or unsubstituted C6 through C20 arylene group, or a substituted or unsubstituted C4 through C20 heteroarylene group, R2 is a hydrogen atom or a substituted or unsubstituted C1 through C10 alkyl group, R3 is a substituted or unsubstituted C1 through C10 alkyl group or a substituted or unsubstituted C1 through C10 alkoxy group, and R4 is a substituted or unsubstituted C1 through C10 alkyl group, and
in General Formula 2, R5 is a substituted or unsubstituted C1 through C10 alkylene group, a substituted or unsubstituted C6 through C20 arylene group, or a substituted or unsubstituted C4 through C20 heteroarylene group, and R6 is a substituted or unsubstituted C1 through C10 alkyl group.

### Claim 9

A method of preparing a nanocomposite comprising:
modifying a surface of an inorganic oxide nanoparticle with a silane coupling agent having an amino group, represented by General Formula 1, or a phosphate ester compound having an amino group, represented by General Formula 2;
imidizing at least a portion of the amino groups to produce an inorganic oxide nanoparticle having a surface modified with a first functional group having an imide backbone;
modifying the surface of the inorganic oxide nanoparticle with a second functional group having an epoxy group to produce a surface-modified inorganic oxide nanoparticle comprising the inorganic oxide nanoparticle and a first functional group and a second functional group modifying the surface of the inorganic oxide nanoparticle; and
mixing the surface-modified inorganic oxide nanoparticle with a diamine and an acid dianhydride and reacting the diamine and the acid dianhydride to produce a mixture of the surface-modified inorganic oxide nanoparticle and a polyamic acid, and treating with heat the resulting mixture
wherein
in General Formula 1, R1 is a substituted or unsubstituted C1 through C10 alkylene group, a substituted or unsubstituted C6 through C20 arylene group, or a substituted or unsubstituted C4 through C20 heteroarylene group, R2 is a hydrogen atom or a substituted or unsubstituted C1 through C10 alkyl group, R3 is a substituted or unsubstituted C1 through C10 alkyl group or a substituted or unsubstituted C1 through C10 alkoxy group, and R4 is a substituted or unsubstituted C1 through C10 alkyl group, and
in General Formula 2, R5 is a substituted or unsubstituted C1 through C10 alkylene group, a substituted or unsubstituted C6 through C20 arylene group, or a substituted or unsubstituted C4 through C20 heteroarylene group, and R6 is a substituted or unsubstituted C1 through C10 alkyl group.

### Claim 10

A method of preparing a nanocomposite comprising:
imidizing at least a portion of amino groups included in a silane coupling agent, represented by General Formula 1, or a phosphate ester compound, represented by General Formula 2, to obtain a silane coupling agent or a phosphate ester compound having an imide backbone;
binding the silane coupling agent or the phosphate ester compound having an imide backbone to a surface of an inorganic oxide nanoparticle to obtain an inorganic oxide nanoparticle having a surface modified with a first functional group having an imide backbone;
modifying the surface of the inorganic oxide nanoparticle with a second functional group having an epoxy group to obtain a surface-modified inorganic oxide nanoparticle comprising the inorganic oxide nanoparticle and a first functional group and a second functional group modifying the surface of the inorganic oxide nanoparticle; and
mixing the surface-modified inorganic oxide nanoparticle with a diamine and an acid dianhydride and reacting the diamine and the acid dianhydride to produce a mixture of the surface-modified inorganic oxide nanoparticle and a polyamic acid, and treating with heat the resulting mixture
wherein
in General Formula 1, R1 is a substituted or unsubstituted C1 through C10 alkylene group, a substituted or unsubstituted C6 through C20 arylene group, or a substituted or unsubstituted C4 through C20 heteroarylene group, R2 is a hydrogen atom or a substituted or unsubstituted C1 through C10 alkyl group, R3 is a substituted or unsubstituted C1 through C10 alkyl group or a substituted or unsubstituted C1 through C10 alkoxy group, and R4 is a substituted or unsubstituted C1 through C10 alkyl group, and
in General Formula 2, R5 is a substituted or unsubstituted C1 through C10 alkylene group, a substituted or unsubstituted C6 through C20 arylene group, or a substituted or unsubstituted C4 through C20 heteroarylene group, and R6 is a substituted or unsubstituted C1 through C10 alkyl group.

### Claim 11 (depends on 1)

A surface light emitting device comprising:
a translucent substrate wherein a transparent substrate of the translucent substrate is covered by a covering layer comprising the nanocomposite of claim 1;
a transparent conductive film laminated on the translucent substrate; and
an organic electroluminescent layer laminated on the transparent conductive film.

### Claim 12 (depends on 11)

The surface light emitting device of claim 11, wherein the translucent substrate comprises the transparent substrate having an embossed surface and the covering layer covers the embossed surface of the transparent substrate.

### Claim 13 (depends on 11)

The surface light emitting device of claim 11, wherein the covering layer comprises the nanocomposite and a scattering particle dispersed in the nanocomposite; and
the translucent substrate comprises the transparent substrate having a flat surface and the covering layer covers the flat surface of the transparent substrate.

### Claim 14 (depends on 11)

The surface light emitting device of claim 11, wherein the translucent substrate comprises the transparent substrate having an embossed surface and the covering layer covers the embossed surface of the transparent substrate; and
the covering layer comprises the nanocomposite and a scattering particle dispersed in the nanocomposite.
