# US 2021/0242408 A1 · Compound for organic electric element, organic electric element using the same, and electronic device thereof

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- Number: US 2021/0242408 A1
- Document ID: US20210242408A1
- Status: Published application
- Kind: A1
- Application number: 17/233,438
- Filed: 2021-04-17
- Published: 2021-08-05
- Earliest claimed: 2016-06-28
- Assignees: Duk San Neolux Co., Ltd.
- Applicants: Duk San Neolux Co., Ltd.
- Inventors: Hyoung Keun PARK; Yun Suk LEE; Ki Ho SO; Jong Gwang PARK; Yeon Seok JEONG; Jung Hwan PARK; Sun Hee LEE; Hak young LEE
- Web page: https://patentgrep.com/patent/US20210242408A1

## CPC

- C07D 333/76: Dibenzothiophenes
- C07D 209/82: Carbazoles; Hydrogenated carbazoles
- C07D 209/88: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 405/14: containing three or more hetero rings
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- 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 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/649: {Aromatic compounds comprising a hetero atom}
- 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}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C07D 419/10: linked by a carbon chain containing aromatic rings
- C07D 419/12: linked by a chain containing hetero atoms as chain links
- C07D 419/14: containing three or more hetero rings
- H10K 10/462: {Insulated gate field-effect transistors [IGFETs]}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- Y02E 10/549: Organic PV cells
- 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 novel compound capable of improving the luminous efficiency, stability and life span of a device, an organic electric element using the same, and an electronic device thereof.

## Claims

### Claim 1

A compound of Formula (1):
wherein:
1) m is an integer of 0 to 4, and n, o and p are an integer of 0 to 3,
2) when m, n, o and p are 1 or more, R1, R2, R3, and R4 are each independently selected from the group consisting of hydrogen; deuterium; a halogen; a C6-C60 aryl group; a fluorenyl group; a C2-C60 heterocyclic group comprising at least one hetero atom of O, N, S, Si and 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), wherein, 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 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 of O, N, S, Si, and P, or
when m, n, o and p are 2 or more, adjacent R1s or adjacent R2s or adjacent R3s or adjacent R4s are optionally combined to each other to form an aromatic or a heteroaromatic ring,
3) X is O, S, or CR′R″, and Y is O, S, NR′ or CR′R″, wherein R′ and R″ are independently hydrogen; a C6-C60 aryl group; a fluorenyl group; a C3-C60 heterocyclic group; or a C1-C50 alkyl group; and R′ and R″ are optionally combined to each other to form a spiro ring.
4) L1 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 group,
5) L2 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 group,
6) Ar1, Ar2 and Ar3 are each independently selected from the group consisting of a C6-C60 aryl group; a fluorenyl group; a C2-C60 heterocyclic group including at least one hetero atom of O, N, S, Si and 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), wherein Ar2 and Ar3, Ar3 and L2, Ar2 and L2, Ar1 and L1, or Ar1 and L2 are optionally bonded to each other to form a ring,
wherein the aryl group, fluorenyl group, arylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group or aryloxy group in R1 to R4, R′, R″, L, L2 and Ar1 to Ar3 are optionally substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane group substituted or unsubstituted with C1-C20 alkyl group or C6-C20 aryl group; siloxane group; boron group; germanium group; cyano group; nitro group; -L′-N(Ra)(Rb); a C1-C20 alkylthio group; C1-C20 alkoxyl group; C1-C20 alkyl group; C2-C20 alkenyl group; C2-C20 alkynyl group; C6-C20 aryl group; C6-C20 aryl group substituted with deuterium; a fluorenyl group; C2-C20 heterocyclic group; C3-C20 cycloalkyl group; C7-C20 arylalkyl group and C8-C20 arylalkenyl group, wherein the substituents may combine to each other and form a saturated or unsaturated ring, wherein the term ‘ring’ means C3-C60 aliphatic ring or C6-C60 aromatic ring or a C2-C60 heterocyclic ring or a fused ring formed by the combination thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the compound of Formula (1) is represented by one of Formulas (2) to (5):
wherein R1, R2, R3, R4, m, n, o, p, L1, L2, Ar1, Ar2, Ar3, X and Y are the same as defined in claim 1.

### Claim 3 (depends on 1)

The compound of claim 1, wherein the compound of Formula (1) is represented by one of Formulas (6) to (9):
wherein R1, R2, R3, R4, m, n, o, p, L1, L2, Ar1, Ar2, Ar3, X and Y are the same as defined in claim 1.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the Y-containing ring in Formula (1) is represented by one of Formulas [A-1] to [A-16]:
wherein R3, R4, o, p and Y are the same as defined in claim 1.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the compound of Formula (1) is represented by one of Formula (10), Formula (11) and Formula (13):
wherein R, R2, R3, R4, m, n, o, p, L1, L2, Ar1, Ar2, Ar3, X and Y are the same as defined in claim 1.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the compound of Formula (1) is represented by one of Formula (14) to Formula (17):
wherein R1, R2, R3, R4, m, n, o, p, L1, L2, Ar1, Ar2, Ar3, and X are the same as defined in claim 1.

### Claim 7 (depends on 1)

The compound of claim 1, wherein L1 and L2 in Formula (1) are selected from the group consisting of Formula (B-1) to Formula (B-12):
wherein:
1) a′, c′, d′ and e′ are each an integer of 0 to 4, b′ is an integer of 0 to 6, and h′ is an integer of 0 to 1,
2) R6, R7 and R8, being the same or different from each other, are each independently selected from the group consisting of deuterium; halogen; a C6-C60 aryl group; a fluorenyl group; a C2-C60 heterocyclic group including at least one heteroatom 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), wherein, 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 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 of O, N, S, Si, and P,
or in the case where a′, b′, c′, d′, e′, f′ and g′ are 2 or more and d is 2, R6, R7 and R8 are each in plural being the same or different from each other, and a plurality of R6 or a plurality of R7 or a plurality of R′ may be bonded to each other to form a ring, or adjacent R6 and R7, or adjacent R7 and R8 may be bonded to each other to form an aromatic or a heteroaromatic ring,
3) Y′ is NR′, O, S, or CR′R″, wherein R′ and R″ are independently hydrogen; a C6-C60 aryl group; a fluorenyl group; a C3-C60 heterocyclic group; or a C1-C50 alkyl group; and R′ and R″ may be bonded to each other to form a spiro ring,
4) Z4, Z5 and Z6 are each independently CR′ or N, and at least one is N.

### Claim 8 (depends on 1)

The compound of claim 1, wherein at least one of L1 and L2 in Formula (1) is substituted at a meta position.

### Claim 9 (depends on 1)

The compound of claim 1, wherein the compound of Formula (1) is selected from the group consisting of Formula (P-123) to Formula (P-125) and Formula (P-128):

### Claim 10 (depends on 1)

An organic electric element comprising a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, wherein the organic material layer comprises one or more of a hole injection layer, a hole transport layer, an emitting-auxiliary layer, an emitting layer, an hole blocking layer, an electronic auxiliary layer, and an electron transport layer, and wherein the organic material layer comprises the compound according to claim 1.

### Claim 11 (depends on 10)

The organic electric element of claim 10, wherein the organic layer is a hole transport layer or an emitting-auxiliary layer, and wherein the compound is a single compound or a mixture of two or more compounds having different structures in the hole transport layer or in the emitting-auxiliary layer.

### Claim 12 (depends on 10)

The organic electric element of claim 10, wherein the organic electric element further comprises a light efficiency enhancing layer formed on the side of the first electrode and/or the second electrode, the side being opposite to the organic material layer not facing the organic material layer.

### Claim 13 (depends on 10)

The organic electric element of claim 10, wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process, and since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the method of forming the organic material layer.

### Claim 14 (depends on 10)

An electronic device comprising a display device including the organic electric element according to claim 10; and a control unit for driving the display device.

### Claim 15 (depends on 14)

The electronic device of claim 14, wherein the organic electric element is at least one of an OLED, an organic solar cell, an organic photo conductor, an organic transistor and an element for monochromic or white illumination.