# US 9,520,567 B2 · Luminescent material for organic optoelectric device and organic optoelectric device and display device

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- Number: US 9,520,567 B2
- Document ID: US9520567B2
- Status: Granted
- Kind: B2
- Application number: 14/760,154
- Filed: 2013-09-25
- Published: 2015-11-26
- Granted: 2016-12-13
- Earliest claimed: 2013-05-16
- Assignees: Cheil Industries Inc.
- Applicants: Cheil Industries Inc.
- Inventors: Han-III Lee; Eun-Sun Yu; Dong-Min Kang; Eui-Su Kang; Yong-Tak Yang; Jae-Jin Oh; Dong-Kyu Ryu; Sang-Shin Lee; Yu-Na Jang; Soo-Young Jeong; Su-Jin Han; Jin-Seok Hong
- Web page: https://patentgrep.com/patent/US9520567B2

## CPC

- H10K 85/622: {containing four rings, e.g. pyrene}
- C07D 213/06: containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D 213/16: containing only one pyridine ring
- C07D 213/22: containing two or more pyridine rings directly linked together, e.g. bipyridyl
- C07D 239/26: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 251/24: to three ring carbon atoms
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/14: containing three or more hetero rings
- C09B 57/00: Other synthetic dyes of known constitution
- C09K 11/06: containing organic luminescent materials
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1059: containing three nitrogen atoms as heteroatoms
- 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 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/342: {comprising iridium}
- H10K 2101/10: Triplet emission
- H10K 2101/30: Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Disclosed are a luminescent material for an organic optoelectric device represented by Chemical Formula 1, an organic optoelectric device including the luminescent material for an organic optoelectric device, and a display device including the organic optoelectric device.

## Claims

### Claim 1

A luminescent material for an organic optoelectric device, the luminescent material being represented by the Chemical Formula 1:
wherein, in Chemical Formula 1,
each Z is independently N or CRa,
at least two Zs are N, at least two Zs in the Z-containing ring bonded to L or the triphenylene group being N,
R1 to R10 and Ra are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof,
L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group,
n1 to n3 are each independently 0 or 1, and
n1+n2+n3≧1.

### Claim 2 (depends on 1)

The luminescent material for an organic optoelectric device of claim 1, wherein the luminescent material is represented by Chemical Formula 1-I or Chemical Formula 1-II:
wherein, in Chemical Formula 1-I and 1-II,
each Z is independently N or CRa,
at least two Zs are N, at least two Zs in the Z-containing ring bonded to L or the triphenylene group being N,
R1 to R10 and Ra are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof,
L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group,
n1 to n3 are each independently 0 or 1, and
n1+n2+n3≧1.

### Claim 3 (depends on 1)

The luminescent material for an organic optoelectric device of claim 1, wherein L is a substituted or unsubstituted phenylene group having a kink structure, a substituted or unsubstituted biphenylene group having a kink structure, or a substituted or unsubstituted terphenylene group having a kink structure.

### Claim 4 (depends on 3)

The luminescent material for an organic optoelectric device of claim 3, wherein L is one of the following substituted or unsubstituted groups
wherein:
R11 to R38 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroarylamine group, a substituted or unsubstituted C1 to C30 alkoxy group, a halogen, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof, and
* represents a binding site to a neighboring atom.

### Claim 5 (depends on 1)

The luminescent material for an organic optoelectric device of claim 1, wherein the luminescent material includes at least two kink structures.

### Claim 6 (depends on 1)

The luminescent material for an organic optoelectric device of claim 1, wherein the luminescent material is represented by Chemical Formula 1a or 1b:
wherein, in Chemical Formula 1a and 1 b,
each Z is independently N or CRa,
at least two Zs are N, at least two Zs in the Z-containing ring bonded to L or the triphenylene group being N, and
R1 to R10 and Ra are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof.

### Claim 7 (depends on 1)

The luminescent material for an organic optoelectric device of claim 1, wherein the luminescent material is represented by one of Chemical Formulae 1c to 1t:
wherein, in Chemical Formulae 1c to 1 t,
each Z is independently N or CRa,
at least two Zs are N, at least two Zs in the Z-containing ring bonded to L or the triphenylene group being N,
R1 to R10 and Ra are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof,
R11 to R14, R17 to R20, R23 to R26 and R36 to R38 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroarylamine group, a substituted or unsubstituted C1 to C30 alkoxy group, a halogen, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof.

### Claim 8 (depends on 1)

The luminescent material for an organic optoelectric device of claim 1, wherein the luminescent material includes one of the following compounds:

### Claim 9 (depends on 1)

The luminescent material for an organic optoelectric device of claim 1, wherein the luminescent material has a LUMO energy of −2.0 to −2.5 eV.

### Claim 10 (depends on 1)

An organic optoelectric device, comprising:
an anode and a cathode facing each other, and
an emission layer positioned between the anode and the cathode, the emission layer including the luminescent material according to claim 1.

### Claim 11 (depends on 10)

The organic optoelectric device of claim 10, wherein:
the luminescent material is a host of the emission layer, and
the emission layer further includes a dopant.

### Claim 12 (depends on 10)

The organic optoelectric device of claim 10, further comprising at least one auxiliary layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer, and a hole blocking layer.

### Claim 13 (depends on 10)

A display device comprising the organic optoelectric device according to claim 10.