# US 10,501,655 B2 · Organic film forming composition and electronic apparatus comprising a cured product thereof

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- Number: US 10,501,655 B2
- Document ID: US10501655B2
- Status: Granted
- Kind: B2
- Application number: 15/183,553
- Filed: 2016-06-15
- Published: 2017-05-25
- Granted: 2019-12-10
- Earliest claimed: 2015-11-25
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Wonmin Yun; Eungseok Park; Byoungduk Lee; Yunah Chung; Yoonhyeung Cho; Yongchan Ju
- Web page: https://patentgrep.com/patent/US10501655B2

## CPC

- H10W 74/47: comprising organic materials, e.g. plastics or resins
- C09D 135/02: Homopolymers or copolymers of esters (C09D135/06, C09D135/08 take precedence)
- H10K 85/10: Organic polymers or oligomers
- H10W 74/121: {by multiple encapsulations, e.g. by a thin protective coating and a thick encapsulation}
- C08F 222/145: {the ester chains containing seven or more carbon atoms}
- C08F 2500/26: Use as polymer for film forming
- C08F 2800/20: as weight or mass percentages
- H10H 20/854: characterised by their material, e.g. epoxy or silicone resins
- H10K 10/88: Passivation; Containers; Encapsulations
- H10K 30/88: Passivation; Containers; Encapsulations
- H10K 50/84: Passivation; Containers; Encapsulations
- Y02E 10/549: Organic PV cells
- H10W: GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
- 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)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- H10H: INORGANIC LIGHT-EMITTING SEMICONDUCTOR DEVICES HAVING POTENTIAL BARRIERS
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

An organic film forming composition having improved hygroscopic properties (e.g., moisture-adsorbing abilities) and an electronic apparatus including a cured product of the organic film forming composition. The organic film forming composition may include a metal (meth)acrylate represented by Formula 1; and a curable material having at least two curable groups selected from the groups represented by Formulae 2A to 2D:

## Claims

### Claim 1

An organic film forming composition comprising:
a metal (meth)acrylate represented by Formula 1; and
a curable material,
wherein, in Formula 1,
M is a metal atom;
n is an integer selected from 1 to 3;
R1 to R3 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C1-C60 heteroaryl group; and
represents an interaction between adjacent ions,
wherein the curable material is selected from ethylene glycol di(meth)acrylate, hexanediol di(meth)acrylate, heptanediol di(meth)acrylate, octanediol di(meth)acrylate, nonanediol di(meth)acrylate, decanediol di(meth)acrylate, dodecanediol di(meth)acrylate, triethylpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, and combinations thereof, and the amount of the metal (meth)acrylate is about 0.1 to 10 parts by weight based on 100 parts by weight of the curable material.

### Claim 2 (depends on 1)

The organic film forming composition of claim 1, wherein, in Formula 1, M is selected from lithium (Li), sodium (Na), calcium (Ca), zinc (Zn), magnesium (Mg), and aluminum (Al).

### Claim 3 (depends on 1)

The organic film forming composition of claim 1, wherein the metal (meth)acrylate is represented by at least one selected from Formulae 1A to 1C:
wherein, in Formulae 1A to 1C,
Ma is a monovalent metal, Mb is a divalent metal, and Mcis a trivalent metal; and
R1a to R1c are each independently the same as described above in connection with R1, R2a to R2c are each independently the same as described above in connection with R2, and R3a to R3c are each independently the same as described above in connection with R3.

### Claim 4 (depends on 1)

The organic film forming composition of claim 1, wherein, in Formula 1, R1 to R3 are each independently selected from the group consisting of:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, and a hydrazono group;
a C1-C10 alkyl group; and
a C1-C10 alkyl group substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, and a hydrazono group.

### Claim 5 (depends on 1)

The organic film forming composition of claim 1, wherein, in Formula 1,
R1 is a C1-C10 alkyl group, and R2 and R3 are both hydrogens; or
R1 to R3 are all hydrogens.

### Claim 6 (depends on 1)

The organic film forming composition of claim 1, wherein the metal (meth)acrylate is selected from sodium (meth)acrylate, lithium (meth)acrylate, calcium (meth)acrylate, magnesium (meth)acrylate, aluminum (meth)acrylate, and combinations thereof.

### Claim 7 (depends on 1)

The organic film forming composition of claim 1, wherein the organic film forming composition further comprises an initiator.

### Claim 8 (depends on 1)

An electronic apparatus comprising:
a substrate;
an electronic device on the substrate; and
a sealing layer covering the electronic device and comprising a number “q” of sealing units, each sealing unit comprising an organic film and an inorganic film that are sequentially stacked on the electronic device, wherein q is an integer of 1 or greater, and the organic film comprises a cured product of the organic film forming composition of claim 1.

### Claim 9 (depends on 8)

The electronic apparatus of claim 8, wherein the electronic device is selected from an organic light-emitting device (OLED), a liquid crystal display (LCD), a light-emitting diode (LED), an organic photovoltaic (OPV) cell, and an organic thin film transistor.

### Claim 10 (depends on 8)

The electronic apparatus of claim 8, wherein the cured product is a polymer comprising: i) a repeating unit originating from the curable material, and ii) at least one moiety originating from the metal (meth)acrylate represented by Formula 1; and
the moiety originating from the metal (meth)acrylate represented by Formula 1 is selected from: a) a repeating unit represented by Formula 10, and b) a terminal group represented by Formula 11:
wherein, in Formulae 10 and 11,
M, n, and R1 to R3 are each independently the same as described above in connection with Formula 1;
R4 is the same as described above in connection with R2; and
* is a binding site to a repeating unit originating from the curable material.

### Claim 11 (depends on 10)

The electronic apparatus of claim 10, wherein a water molecule that has penetrated into the sealing unit is adsorbed to a carboxylate group (COO−) in Formulae 10 and/or 11 via a hydrogen bond or is adsorbed to a metal ion (Mn+) in Formulae 10 and/or 11 via an ion-dipole interaction.

### Claim 12 (depends on 8)

The electronic apparatus of claim 8, wherein the inorganic film comprises a metal, a metal nitride, a metal oxide, a metal oxynitride, or a combination thereof.

### Claim 13 (depends on 8)

The electronic apparatus of claim 8, wherein the sealing layer further comprises a lower inorganic film between the electronic device and the organic film.

### Claim 14 (depends on 8)

The electronic apparatus of claim 8, wherein the electronic apparatus further comprises at least one selected from a capping layer and a protective layer between the electronic device and the sealing unit.