# US 10,121,987 B2 · Organic light emitting diode display including capping layer having high refractive index

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- Number: US 10,121,987 B2
- Document ID: US10121987B2
- Status: Granted
- Kind: B2
- Application number: 14/853,165
- Filed: 2015-09-14
- Published: 2016-05-26
- Granted: 2018-11-06
- Earliest claimed: 2014-11-24
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Hwan-Hee Cho; Myeong-Suk Kim; Sung-Wook Kim
- Web page: https://patentgrep.com/patent/US10121987B2

## CPC

- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 59/879: {comprising refractive means, e.g. lenses}
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- H10K 85/658: {Organoboranes}
- H10K 59/8731: {multilayered coatings having a repetitive structure, e.g. having multiple organic-inorganic bilayers}
- H10K 2101/00: Properties of the organic materials covered by group H10K85/00
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

An organic light emitting diode display including a first substrate; a first electrode on the first substrate; an organic light emitting layer on the first electrode; a second electrode on the organic light emitting layer; and a capping layer on the second electrode, wherein the capping layer includes at least one heterocyclic compound, the heterocyclic compound including a carbazole group and a heterocyclic group bonded with the carbazole group.

## Claims

### Claim 1

An organic light emitting diode display, comprising:
a first substrate;
a first electrode on the first substrate;
an organic light emitting layer on the first electrode;
a second electrode on the organic light emitting layer; and
a capping layer on the second electrode,
wherein the capping layer includes at least one heterocyclic compound, the heterocyclic compound including a carbazole group and a heterocyclic group bonded with the carbazole group, and
wherein the heterocyclic group bonded with the carbazole group includes a 6-membered ring with a heteroatom in the 6-membered ring.

### Claim 2 (depends on 1)

The organic light emitting diode display as claimed in claim 1, wherein the heterocyclic compound is represented by one of the following Chemical Formulae 1 to 5:
wherein, in Chemical Formulae 1 to 5,
A1 to A7 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 1 to 30 ring carbon atoms, one of A1 or A2 including the 6-member ring with a heteroatom in the ring, one of A3, A4, or A5, including the 6-membered ring with a heteroatom in the ring, and one of A6 or A7 including the 6-membered ring with a heteroatom in the ring;
Y1 to Y16 are each independently C—R or a nitrogen atom, wherein each R of the C—R is independently one of a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 1 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and having a linear, branched, or cyclic structure, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted dialkylarylsilyl group having 8 to 40 carbon atoms, a substituted or unsubstituted alkyldiarylsilyl group having 13 to 50 carbon atoms, a substituted or unsubstituted triarylsilyl group having 18 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a halogen atom, a cyano group, a hydroxyl group, a nitro group, or a carboxyl group;
R of adjacent C—R, when two of Y1 to Y16 that are adjacent to each other are C—R, are separate or are combined to form a cyclic structure;
L1 to L12 are each independently a single bond or a connecting group;
X1 is carbon or silicon;
R1 and R2 are each independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 1 to 30 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, R1 and R2 being separate or bonded together to form a cyclic structure; and
X2 is boron, phosphorus, or P═O.

### Claim 3 (depends on 2)

The organic light emitting diode display as claimed in claim 2, wherein the compound represented by Chemical Formula 1 is one of the following Compounds 1 to 48:

### Claim 4 (depends on 2)

The organic light emitting diode display as claimed in claim 2, wherein the compound represented by Chemical Formula 2 is one of the following Compounds 49 to 73

### Claim 5 (depends on 2)

The organic light emitting diode display as claimed in claim 2, wherein the compound represented by Chemical Formula 3 is one of the following Compounds 74 to 78

### Claim 6 (depends on 2)

The organic light emitting diode display as claimed in claim 2, wherein the compound represented by Chemical Formula 4 is one of the following Compounds 79 to 84

### Claim 7 (depends on 2)

The organic light emitting diode display as claimed in claim 2, wherein the compound represented by Chemical Formula 5 is one of the following Compounds 85 to 88

### Claim 8 (depends on 1)

The organic light emitting diode display as claimed in claim 1, wherein the capping layer has a refractive index of about 1.9 or higher.

### Claim 9 (depends on 1)

The organic light emitting diode display as claimed in claim 1, wherein the capping layer has a refractive index of about 1.9 to about 3.0.

### Claim 10 (depends on 1)

The organic light emitting diode display as claimed in claim 1, wherein the capping layer has a thickness of about 10 nm to about 300 nm.

### Claim 11 (depends on 1)

The organic light emitting diode display as claimed in claim 1, further comprising at least one of a hole injection layer and a hole transporting layer between the first electrode and the organic light emitting layer.

### Claim 12 (depends on 1)

The organic light emitting diode display as claimed in claim 1, further comprising at least one of an electron transporting layer and an electron injection layer between the organic light emitting layer and the second electrode.

### Claim 13 (depends on 1)

The organic light emitting diode display as claimed in claim 1, further comprising a second substrate on the capping layer, the second substrate being spaced apart from the capping layer.

### Claim 14 (depends on 13)

The organic light emitting diode display as claimed in claim 13, further comprising an air layer in a space between the capping layer and the second substrate.

### Claim 15 (depends on 13)

The organic light emitting diode display as claimed in claim 13, further comprising a filling member in a space between the capping layer and the second substrate.

### Claim 16 (depends on 1)

The organic light emitting diode display as claimed in claim 1, further comprising a thin film encapsulation layer on the capping layer.

### Claim 17

An organic light emitting diode display, comprising:
a first substrate;
a first electrode on the first substrate;
an organic light emitting layer on the first electrode;
a second electrode on the organic light emitting layer;
a capping layer on the second electrode; and
a second substrate on the capping layer, the second substrate being spaced apart from the capping layer,
wherein the capping layer includes at least one heterocyclic compound, the heterocyclic compound including a carbazole group and a heterocyclic group bonded with the carbazole group.

### Claim 18

An organic light emitting diode display, comprising:
a first substrate;
a first electrode on the first substrate;
an organic light emitting layer on the first electrode;
a second electrode on the organic light emitting layer; and
a capping layer on the second electrode; and
a thin film encapsulation layer on the capping layer,
wherein the capping layer includes at least one heterocyclic compound, the heterocyclic compound including a carbazole group and a heterocyclic group bonded with the carbazole group.
