# US 10,319,915 B2 · Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

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- Number: US 10,319,915 B2
- Document ID: US10319915B2
- Status: Granted
- Kind: B2
- Application number: 15/427,363
- Filed: 2017-02-08
- Published: 2017-08-17
- Granted: 2019-06-11
- Earliest claimed: 2016-02-11
- Assignees: Duk San Neolux Co., Ltd.
- Applicants: Duk San Neolux Co., Ltd.
- Inventors: Jong Gwang Park; Yun Suk Lee; Ki Ho So; Hyoung Keun Park; Yeon Seok Jeong; Jung Hwan Park; Sun Hee Lee; Gyu Min Lee
- Web page: https://patentgrep.com/patent/US10319915B2

## CPC

- H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source}
- C07D 333/76: Dibenzothiophenes
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 409/14: containing three or more hetero rings
- C09K 11/06: containing organic luminescent materials
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1088: containing oxygen as the only heteroatom
- C09K 2211/1092: containing sulfur as the only heteroatom
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/156: {comprising a multilayered structure}
- H10K 71/12: using liquid deposition, e.g. spin coating
- H10K 71/135: {using ink-jet printing}
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- Y02E 10/549: Organic PV cells
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Provided is a compound for an EBL capable of improving the light emitting efficiency, stability and life span of a device, and an organic electric element and an electronic device using the same.

## Claims

### Claim 1

A compound represented by Formula (1) below
wherein,
1) Ar1, Ar2, Ar3 and Ar4 are each independently selected from the group consisting of: a halogen; a C6-C60 aryl group; a fluorenyl group; a C2-C60 heterocyclic group including at least one hetero atom of O, N, S, Si or P; a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring; a C1-C50 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C30 alkoxyl group; a C6-C30 aryloxy group; and -L'-N(Ra)(Rb), or may combine to form an aromatic ring or a hetero-aromatic ring by condensation of adjacent groups to a ring, wherein at least one of Ar1, Ar2, Ar3 and Ar4 is a substituent represented by Formula (1-1) above,
2) L1 and L2 are each selected from the group consisting of: a single bond; a C6-C60 arylene group; a fluorenylene group; and a C2-C60 hetero arylene group including at least one hetero atom of O, N, S, Si or P,
3) l is an integer of 0 to 4, m, n and o are each an integer of 0 to 3,
4) R1, R2, R3 and R4 are each independently selected from the group consisting of: hydrogen; deuterium; halogen; a C6-C60 aryl group; a fluorenyl group; a C2-C60 heterocyclic group including at least one hetero atom of O, N, S, Si or P; a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring; a C1-C50 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C30 alkoxy group; a C6-C30 aryloxy group; and -L'-N(Ra)(Rb), wherein when R1 or R2 is plural, plurality of R1 or a plurality of R2 may combine to each other to form a ring,
5) X is O or S, and
6) In -L'-N(Ra)(Rb) above, L′ is selected from the group consisting of: a single bond; a C6-C60 arylene group; a fluorenylene group; a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring; and a C2-C60 heterocyclic, and Ra and Rb are each independently selected from the group consisting of: a C6-C60 aryl group; a fluorenyl group; a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring; and a C2-C60 heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si, and P,
wherein, the aryl group; fluorenyl group; arylene group; heterocyclic group; fused ring group described above may be substituted by one or more of the substituent(s) selected from the group consisting of: deuterium; halogen; a silane group; a siloxan group; a boron group; a germanium group; a cyano group; a nitro group; -L′-N(Ra)(Rb); a C1-C20 alkylthio group; a C1-C20 alkoxyl group; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C6-C20 aryl group; a C6-C20 aryl group substituted by deuterium; fluorenyl group; a C2-C20 heterocyclic group; a C3-C20 cycloalkyl group; a C7-C20 arylalkyl group; and a C8-C20 arylalkenyl group and also may combine to each other to form a saturated or unsaturated ring selected from the group consisting of: an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a hetero ring having 2 to 60 carbon atoms, and a fused ring formed by the combination of them.

### Claim 2 (depends on 1)

The compound according to claim 1 represented by Formula (2) or Formula (3) below,
wherein, R1, R2, R3, R4, l, m, n, o, Ar1, Ar2, Ar3, Ar4, L1, L2, X are the same as defined in claim 1.

### Claim 3 (depends on 1)

The compound according to claim 1 represented by any one of Formula (4) to Formula (9) below,
wherein, R1, R2, R3, R4, l, m, n, o, Ar1, Ar2, Ar3, Ar4, L1, L2, X are the same as defined in claim 1.

### Claim 4 (depends on 1)

The compound according to claim 1 represented by any one of the following compounds:

### Claim 5 (depends on 1)

An organic electric element comprising: a first electrode; a second electrode; and an organic material layer positioned between the first electrode and the second electrode, wherein the organic material layer comprises one or more of the compounds according to claim 1.

### Claim 6 (depends on 5)

The organic electric element according to claim 5, wherein the organic material layer is selected from the group consisting of a hole injection layer, a hole transport layer, an emitting-auxiliary layer, and an emitting layer, and contains one or more of the compounds.

### Claim 7 (depends on 6)

The organic electric element according to claim 6, wherein the organic material layer is a hole transport layer or an emitting-auxiliary layer.

### Claim 8 (depends on 5)

The organic electric element according to claim 5, further comprising a light efficiency enhancing layer formed on at least one of the opposite side to the organic material layer among one side of the first electrode, or one of the opposite side to the organic material layer among one side of the second electrode.

### Claim 9 (depends on 5)

The organic electric element according to claim 5, wherein the organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process.

### Claim 10 (depends on 5)

An electronic device comprising a display apparatus comprising the organic electric element according to claim 5; and a driving part configured to drive the display apparatus.

### Claim 11 (depends on 10)

The electronic device according to claim 10, wherein the organic electric element is at least one of an organic light emitting diode (OLED), an organic solar cell, an organic photo conductor, an organic transistor, and a device for monochromic or white illumination.