# US 10,319,946 B2 · Organic light emitting device encapsulating composition, and organic light emitting device display apparatus manufactured using same

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- Number: US 10,319,946 B2
- Document ID: US10319946B2
- Status: Granted
- Kind: B2
- Application number: 15/129,924
- Filed: 2015-04-09
- Published: 2017-05-25
- Granted: 2019-06-11
- Earliest claimed: 2014-04-23
- Assignees: Samsung SDI Co., Ltd.
- Applicants: Samsung SDI Co., Ltd.
- Inventors: Seong Ryong Nam; Ji Yeon Lee; Kyoung Jin Ha; Sung Min Ko; Han Sung Yu
- Web page: https://patentgrep.com/patent/US10319946B2

## CPC

- C08F 230/08: containing silicon
- C08F 222/102: {of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate}
- H10K 59/8731: {multilayered coatings having a repetitive structure, e.g. having multiple organic-inorganic bilayers}
- C08L 33/10: Homopolymers or copolymers of methacrylic acid esters
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

A composition for encapsulation of an organic light emitting diode and an organic light emitting diode display manufactured using the same. The composition for encapsulation includes: about 10 wt % to about 70 wt % of (A) a non-silicon-based di(meth)acrylate; about 20 wt % to about 70 wt % of (B) a silicon-based di(meth)acrylate; about 5 wt % to about 40 wt % of (C) a mono(meth)acrylate; and about 1 wt % to about 10 wt % of (D) an initiator, wherein the (B) silicon-based di(meth)acrylate is represented by Formula 1.

## Claims

### Claim 1

A composition for encapsulation of an organic light emitting diode, the composition comprising:
about 10 wt % to about 70 wt % of (A) a non-silicon-based di(meth)acrylate;
about 20 wt % to about 70 wt % of (B) a silicon-based di(meth)acrylate;
about 5 wt % to about 40 wt % of (C) a mono(meth)acrylate; and
about 1 wt % to about 10 wt % of (D) an initiator, based on the total weight of (A), (B), (C) and (D),
wherein the (B) silicon-based di(meth)acrylate is represented by Formula 1:
wherein, in Formula 1,
R1 and R2 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C30 alkylene ether group, *—N(R′)—(R″)—* (* represents a binding site for an element, R′ is hydrogen or a substituted or unsubstituted C1 to C30 alkyl group, and R″ is a substituted or unsubstituted C1 to C20 alkylene group), a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C7 to C30 arylalkylene group, or *—(R′)—O—** (* represents a binding site for O in Formula 1, ** represents a binding site for Si in Formula 1, and R′ is a substituted or unsubstituted C1 to C30 alkylene group);
X1, X2, X3, X4, X5 and X6 are each independently hydrogen, a hydroxyl group, a halogen, a cyano group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 alkyl ether group, *—N(R′)—(R″)—* (* represents a binding site for an element, and R′ and R″ are each independently hydrogen or a substituted or unsubstituted C1 to C30 alkyl group), a substituted or unsubstituted C1 to C30 alkyl sulfide group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted C7 to C30 arylalkyl group;
at least one of X1, X2, X3, X4, X5 and X6 is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group;
R3 and R4 are each independently hydrogen or a methyl group; and
n is an integer from 0 to 30, or ranges on average from 0 to 30.

### Claim 2 (depends on 1)

The composition for encapsulation of an organic light emitting diode according to claim 1, comprising:
about 10 wt % to about 50 wt % of the (A) non-silicon-based di(meth)acrylate;
about 20 wt % to about 70 wt % of the (B) silicon-based di(meth)acrylate;
about 5 wt % to about 40 wt % of the (C) mono(meth)acrylate; and
about 1 wt % to about 10 wt % of the (D) initiator, based on the total weight of (A), (B), (C) and (D).

### Claim 3 (depends on 1)

The composition for encapsulation of an organic light emitting diode according to claim 1, wherein:
R1 and R2 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, or a substituted or unsubstituted C1 to C30 alkylene ether group;
X1, X2, X3, X4, X5 and X6 are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 alkyl ether group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted C7 to C30 arylalkyl group; and
at least one of X1, X2, X3, X4, X5 and X6 is a substituted or unsubstituted C6 to C30 aryl group.

### Claim 4 (depends on 1)

The composition for encapsulation of an organic light emitting diode according to claim 1, wherein the (B) silicon-based di(meth)acrylate is represented by any one of Formulae 3 to 8:

### Claim 5 (depends on 1)

The composition for encapsulation of an organic light emitting diode according to claim 1, wherein the (A) non-silicon-based di(meth)acrylate is represented by Formula 2:
wherein, in Formula 2,
R3 and R4 are each independently hydrogen or a methyl group; and
R5 is a substituted or unsubstituted C1 to C20 alkylene group.

### Claim 6 (depends on 1)

The composition for encapsulation of an organic light emitting diode according to claim 1, wherein the (C) mono(meth)acrylate is a non-silicon-based mono(meth)acrylate.

### Claim 7 (depends on 1)

The composition for encapsulation of an organic light emitting diode according to claim 1, wherein the (C) mono(meth)acrylate includes an aromatic mono(meth)acrylate.

### Claim 8 (depends on 1)

The composition for encapsulation of an organic light emitting diode according to claim 1, wherein the (C) mono(meth)acrylate includes a non-aromatic mono(meth)acrylate.

### Claim 9 (depends on 1)

The composition for encapsulation of an organic light emitting diode according to claim 1, further comprising a heat stabilizer.

### Claim 10 (depends on 9)

The composition for encapsulation of an organic light emitting diode according to claim 9, wherein the heat stabilizer is present in an amount of about 0.01 ppm to about 2,000 ppm based on the total weight of (A), (B), (C) and (D).

### Claim 11 (depends on 9)

The composition for encapsulation of an organic light emitting diode according to claim 9, wherein:
the (A) non-silicon-based di(meth)acrylate includes a C1 to C20 alkylene group-containing di(meth)acrylate;
the (B) silicon-based di(meth)acrylate is represented by any one of Formulae 3 to 8:
the (C) mono(meth)acrylate is represented by Formula 9:
wherein, in Formula 9, R3 is hydrogen or a methyl group; s is an integer from 0 to 10; and R6 is a substituted or unsubstituted C6 to C50 aryl group or a substituted or unsubstituted C6 to C50 aryloxy group; and
the (D) initiator includes a phosphorus initiator.

### Claim 12 (depends on 1)

The composition for encapsulation of an organic light emitting diode according to claim 1, wherein the composition has a viscosity at 25° C.±2° C. of about 5 cPs to about 50 cPs.

### Claim 13 (depends on 1)

An organic light emitting diode display, comprising:
an organic light emitting diode; and
a barrier stack formed on the organic light emitting diode and including an inorganic barrier layer and an organic barrier layer,
wherein the organic barrier layer is formed of the composition for encapsulation of an organic light emitting diode according to claim 1.

### Claim 14 (depends on 13)

The display according to claim 13, wherein the organic barrier layer is formed of the composition for encapsulation of an organic light emitting diode using inkjet printing or deposition.