# US 2019/0245154 A1 · Organic electroluminescent device, organic electroluminescent display device including the same, and organometallic compound for organic electroluminescent device

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- Number: US 2019/0245154 A1
- Document ID: US20190245154A1
- Status: Published application
- Kind: A1
- Application number: 16/260,104
- Filed: 2019-01-29
- Published: 2019-08-08
- Earliest claimed: 2018-02-02
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Jimyoung YE; Myeongsuk KlM; Byeongwook YOO; Yiseul KIM; Hyoyeon KIM; Jaehoon HWANG
- Web page: https://patentgrep.com/patent/US20190245154A1

## CPC

- H10K 85/346: {comprising platinum}
- C07F 15/002: {Osmium compounds}
- C07F 15/0033: {Iridium compounds}
- C07F 15/0086: {Platinum compounds}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/171: {Electron injection layers}
- H10K 59/122: Pixel-defining structures or layers, e.g. banks
- H10K 59/131: Interconnections, e.g. wiring lines or terminals
- H10K 85/342: {comprising iridium}
- H10K 85/348: {comprising osmium}
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 59/351: {comprising more than three subpixels, e.g. red-green-blue-white [RGBW]}
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 2101/10: Triplet emission
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

An organic electroluminescent device includes a first electrode, a hole transport region provided on the first electrode, an emission layer provided on the hole transport region, an electron transport region provided on the emission layer, and a second electrode provided on the electron transport region, wherein the emission layer includes an organometallic compound represented by Formula 1.

## Claims

### Claim 1

An organic electroluminescent device, comprising:
a first electrode;
a hole transport region provided on the first electrode;
an emission layer provided on the hole transport region;
an electron transport region provided on the emission layer; and
a second electrode provided on the electron transport region,
wherein the emission layer comprises an organometallic compound represented by the following Formula 1:
wherein in Formula 1,
R1 and R2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, or are combined with an adjacent group to form a ring,
“p” is an integer of 0 to 4,
“q” is an integer of 0 to 3,
“n” is 1 or 2,
M is Pt, Ir or Os, and
L1 is a bidentate ligand.

### Claim 2 (depends on 1)

The organic electroluminescent device of claim 1, wherein L1 is represented by one of the following Formulae 2-1 to 2-6:
wherein in Formulae 2-1 to 2-6,
X1 is O or NR′,
X2 to X4 are each independently CH, N, or NR21,
Y1 is a direct linkage or CH,
R′, and R3 to R21 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or are combined with an adjacent group to form a ring,
“a”, “c”, “d”, “e”, “g” and “j” are each independently an integer of 0 to 4,
“b” is an integer of 0 to 5,
“f” and “i” are an integer of 0 to 3, and
“h” is an integer of 0 to 2.

### Claim 3 (depends on 1)

The organic electroluminescent device of claim 1, wherein M is Pt.

### Claim 4 (depends on 1)

The organic electroluminescent device of claim 1, wherein Formula 1 is represented by one of the following Formulae 1-1 to 1-3:
wherein in Formulae 1-1 to 1-3,
M, R2, L1, “n” and “q” are the same as defined in claim 1.

### Claim 5 (depends on 1)

The organic electroluminescent device of claim 1, wherein the emission layer comprises a host and a dopant and emits near-infrared rays in a wavelength region of 750 nm to 1,000 nm, and
the dopant comprises the organometallic compound represented by Formula 1.

### Claim 6 (depends on 1)

The organic electroluminescent device of claim 1, wherein the organometallic compound represented by Formula 1 is at least one selected from compounds represented in the following Compound Group 1:

### Claim 7

An organic electroluminescent display device, comprising:
a first pixel comprising a first organic electroluminescent device which emits first visible rays;
a second pixel comprising a second organic electroluminescent device which emits second visible rays;
a third pixel comprising a third organic electroluminescent device which emits third visible rays; and
a fourth pixel comprising a fourth organic electroluminescent device which emits near-infrared rays;
wherein the fourth organic electroluminescent device comprises an emission layer comprising an organometallic compound represented by the following Formula 1:
wherein in Formula 1,
R1 and R2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, or are combined with an adjacent group to form a ring,
“p” is an integer of 0 to 4,
“q” is an integer of 0 to 3,
“n” is 1 or 2,
M is Pt, Ir or Os, and
L1 is a bidentate ligand.

### Claim 8 (depends on 7)

The organic electroluminescent display device of claim 7, wherein L1 is represented by one of the following Formulae 2-1 to 2-6:
wherein in Formulae 2-1 to 2-6,
X1 is O or NR′,
X2 to X4 are each independently CH, N, or NR21,
Y1 is a direct linkage or CH,
R′, and R3 to R21 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or are combined with an adjacent group to form a ring,
“a”, “c”, “d”, “e”, “g” and “j” are each independently an integer of 0 to 4,
“b” is an integer of 0 to 5,
“f” and “i” are an integer of 0 to 3, and
“h” is an integer of 0 to 2.

### Claim 9 (depends on 7)

The organic electroluminescent display device of claim 7, wherein M is Pt.

### Claim 10 (depends on 7)

The organic electroluminescent display device of claim 7, wherein Formula 1 is represented by one of the following Formulae 1-1 to 1-3:
wherein in Formulae 1-1 to 1-3,
M, R2, L1, “n” and “q” are the same as defined in claim 7.

### Claim 11 (depends on 7)

The organic electroluminescent display device of claim 7, wherein the organometallic compound represented by Formula 1 emits near-infrared rays in a wavelength region of 750 nm to 1,000 nm.

### Claim 12 (depends on 7)

The organic electroluminescent display device of claim 7, wherein the organometallic compound represented by Formula 1 is at least one selected from compounds represented in the following Compound Group 1:

### Claim 13

An organometallic compound represented by the following Formula 1:
wherein in Formula 1,
R1 and R2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, or are combined with an adjacent group to form a ring,
“p” is an integer of 0 to 4,
“q” is an integer of 0 to 3,
“n” is 1 or 2,
M is Pt, Ir or Os, and
L1 is a bidentate ligand.

### Claim 14 (depends on 13)

The organometallic compound of claim 13, wherein L1 is represented by one of the following Formulae 2-1 to 2-6:
wherein in Formulae 2-1 to 2-6,
X1 is O or NR′,
X2 to X4 are each independently CH, N, or NR21,
Y1 is a direct linkage or CH,
R′, and R3 to R21 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or are combined with an adjacent group to form a ring,
“a”, “c”, “d”, “e”, “g” and “j” are each independently an integer of 0 to 4,
“b” is an integer of 0 to 5,
“f” and “i” are an integer of 0 to 3, and
“h” is an integer of 0 to 2.

### Claim 15 (depends on 13)

The organometallic compound of claim 13, wherein M is Pt.

### Claim 16 (depends on 13)

The organometallic compound of claim 13, wherein Formula 1 is represented by one of the following Formulae 1-1 to 1-3:
wherein in Formulae 1-1 to 1-3,
M, R2, L1, “n” and “q” are the same as defined in claim 13.

### Claim 17 (depends on 13)

The organometallic compound of claim 13, wherein the organometallic compound represented by Formula 1 emits near-infrared rays in a wavelength region of 750 nm to 1,000 nm.

### Claim 18 (depends on 13)

The organometallic compound of claim 13, wherein the organometallic compound represented by Formula 1 is at least one selected from compounds represented in the following Compound Group 1: