# US 2014/0197386 A1 · Material for organic optoelectronic device, organic light emitting diode including the same, and display including the organic light emitting diode

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- Number: US 2014/0197386 A1
- Document ID: US20140197386A1
- Status: Published application
- Kind: A1
- Application number: 14/035,370
- Filed: 2013-09-24
- Published: 2014-07-17
- Earliest claimed: 2013-01-17
- Assignees: Cheil Industries Inc.; Samsung Electronics Co., Ltd.
- Applicants: Cheil Industries Inc.; Samsung Electronics Co., Ltd.
- Inventors: Hyung-Sun KIM; Byungku KIM; Chang woo KIM; Jin Hyeon RYU; Moo-Jin PARK; Jae-Deuk YANG; Eun-Sun YU; Ho-Jae LEE
- Web page: https://patentgrep.com/patent/US20140197386A1

## CPC

- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- C09K 11/06: containing organic luminescent materials
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/342: {comprising iridium}
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- 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 2101/90: {Multiple hosts in the emissive layer}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A material for an organic optoelectronic device including a first compound represented by Chemical Formula A-1 and a second compound represented by Chemical Formula B-1: wherein, variables R1-R8, Ar1, Ar2, L1, L2, X2, n1, and n2 are described in the specification.

## Claims

### Claim 1

A material for an organic optoelectronic device, comprising
a first compound represented by Chemical Formula A-1, and
a second compound represented by Chemical Formula B-1:
wherein, in Chemical Formula A-1,
Ar1 is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties,
L1 is a substituted or unsubstituted C2 to C6 alkenylene group, a substituted or unsubstituted C2 to C6 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
n1 is an integer of 0 to 3,
R1 to R4 are independently hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C20 sulfamoylamino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthio group, a substituted or unsubstituted C6 to C20 arylthio group, a substituted or unsubstituted C1 to C20 heterocyclothio group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof,
A is a substituted or unsubstituted C5 to C80 aryl group or a substituted or unsubstituted X2 to C80 heteroaryl group, and A includes one or five rings,
wherein, in Chemical Formula B-1,
X2 is —O—, —S—, or —NR′—,
Ar2, R5 to R8, and R′ are independently hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C20 sulfamoylamino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthio group, a substituted or unsubstituted C6 to C20 arylthio group, a substituted or unsubstituted C1 to C20 heterocyclothio group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof,
L2 is a substituted or unsubstituted C2 to C6 alkenylene group, a substituted or unsubstituted C2 to C6 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof, and
n2 is an integer of 0 to 3.

### Claim 2 (depends on 1)

The material for an organic optoelectronic device of claim 1, wherein A is represented by Chemical Formula A-2 or A-3:
wherein, in Chemical Formulae A-2 and A-3,
two adjacent *'s indicate bonding positions with Chemical Formula A-1,
X1 is O—, —S—, or —NR′—, and
R1, R2, and R′ are independently hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C20 sulfamoylamino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthio group, a substituted or unsubstituted C6 to C20 arylthio group, a substituted or unsubstituted C1 to C20 heterocyclothio group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof.

### Claim 3 (depends on 1)

The material for an organic optoelectronic device of claim 1, wherein A is represented by one of Chemical Formulae A-4 to A-9:
wherein, in Chemical Formula A-4 to A-9,
two adjacent *'s indicate bonding positions with Chemical Formula A-1,
X1 is O—, —S—, or —NR′—, and
R1, R2, and R′ are independently hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C20 sulfamoylamino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthio group, a substituted or unsubstituted C6 to C20 arylthio group, a substituted or unsubstituted C1 to C20 heterocyclothio group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof.

### Claim 4 (depends on 1)

The material for an organic optoelectronic device of claim 1, wherein Chemical Formula A-1 is represented by Chemical Formula A-10:
wherein, in Chemical Formula A-10,
Ar1 is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties,
L1 is a substituted or unsubstituted C2 to C6 alkenylene group, a substituted or unsubstituted C2 to C6 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
n1 is an integer of 0 to 3, and
R1 to R4 are independently hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C20 sulfamoylamino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthio group, a substituted or unsubstituted C6 to C20 arylthio group, a substituted or unsubstituted C1 to C20 heterocyclothio group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof.

### Claim 5 (depends on 1)

The material for an organic optoelectronic device of claim 1, wherein n2 in Chemical Formula B-1 is 0.

### Claim 6 (depends on 1)

The material for an organic optoelectronic device of claim 1, wherein in Chemical Formula B-1, X2 is NR′, wherein R′ is a substituted or unsubstituted C6 to C30 aryl group.

### Claim 7 (depends on 1)

The material for an organic optoelectronic device of claim 1, wherein the material for an organic optoelectronic device further comprises a dopant represented by Chemical Formula C-1:
wherein, in Chemical Formula C-1,
X1 to X6, Y1, and Y2 are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 fluoroalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 amino group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, or a substituent represented by Chemical Formula X-1,
Ar1 and Ar2 are substituted or unsubstituted C6 to C30 arylene groups,
R1 and R2 are independently hydrogen, deuterium, a C1 to C30 alkyl group substituted or unsubstituted with a halogen, a C6 to C30 aryl group substituted or unsubstituted with a C1 to C30 alkyl group or a halogen,
m1 and m2 are integers ranging from 0 to 2, and m1+m2 is greater than or equal to 1,
L is a bidentate ligand of a monovalent anion, and is coordination-bonded with iridium through lone pair electrons of carbon or heteroatom, and
n1 and n2 are independently integers ranging from 0 to 3, and n1+n2 is an integer ranging from 1 to 3,
wherein, in Chemical Formula X-1,
R3, R4, and R5 are independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 fluoroalkyl group, a substituted or unsubstituted C1 to C20 amino group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

### Claim 8 (depends on 1)

The material for an organic optoelectronic device of claim 1, wherein in Chemical Formula C-1,
m1 is 1 or 2 and Y1 is a substituent represented by Chemical Formula X-1, or
m2 is 1 or 2 and Y2 is a substituent represented by Chemical Formula X-1.

### Claim 9 (depends on 1)

The material for an organic optoelectronic device of claim 1, wherein in Chemical Formula C-1, n1+n2 is 3.

### Claim 10 (depends on 1)

The material for an organic optoelectronic device of claim 1, wherein in Chemical Formula C-1, n1 or n2 is 3.

### Claim 11 (depends on 1)

The material for an organic optoelectronic device of claim 1, wherein in Chemical Formula C-1, L is selected from Chemical Formulae L-1 to L-14:
wherein, in Chemical Formulae L-1 to L-14,
asterisk (*) indicates a site bonding with iridium,
R101 to R103 are independently hydrogen, deuterium, a C1 to C30 alkyl group substituted or unsubstituted with a halogen, or a C6 to C30 aryl group substituted or unsubstituted with a C1 to C30 alkyl group or a halogen,
R104 to R115 are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 an arylamino group, SF5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group, and
R116 to R117 are independently hydrogen, deuterium, a C1 to C30 alkyl group substituted or unsubstituted with a halogen, or a C6 to C30 aryl group substituted or unsubstituted with a C1 to C30 alkyl group.

### Claim 12 (depends on 1)

The material for an organic optoelectronic device of claim 1, wherein the substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties is a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted oxatriazolyl group, a substituted or unsubstituted thiatriazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzotriazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenanthrolinyl group, or substituted or unsubstituted phenazinyl group.

### Claim 13 (depends on 1)

The material for an organic optoelectronic device of claim 1, wherein the substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties is represented by one of Chemical Formulae E-1 to E-5:

### Claim 14 (depends on 1)

The material for an organic optoelectronic device of claim 1, wherein Chemical Formula A-1 is represented by one of Chemical Formulae H-1 to H-35:

### Claim 15 (depends on 1)

The material for an organic optoelectronic device of claim 1, wherein Chemical Formula B-1 is represented by one of Chemical Formulae I-1 to I-31:

### Claim 16 (depends on 7)

The material for an organic optoelectronic device of claim 7, wherein Chemical Formula C-1 is represented by Chemical Formulae J-1 to J-20:

### Claim 17 (depends on 1)

An organic light emitting diode comprising
an anode,
a cathode, and
at least one organic layer between the anode and the cathode,
wherein at least one organic layer comprises the material for an organic optoelectronic device according to claim 1.

### Claim 18 (depends on 17)

The organic light emitting diode of claim 17, wherein the at least one organic layer is an emission layer.

### Claim 19 (depends on 17)

A display device comprising the organic light emitting diode according to claim 17.

### Claim 20 (depends on 19)

The display device of claim 19, wherein A is represented by Chemical Formula A-2 or A-3:
wherein, in Chemical Formulae A-2 and A-3,
two adjacent *'s indicate bonding positions with Chemical Formula A-1,
X1 is O—, —S—, or —NR′—, and
R1, R2, and R′ are independently hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C20 sulfamoylamino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthio group, a substituted or unsubstituted C6 to C20 arylthio group, a substituted or unsubstituted C1 to C20 heterocyclothio group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof.