# US 12,193,321 B2 · Compound for organic electric element, organic electric element comprising the same, and electronic device thereof

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- Number: US 12,193,321 B2
- Document ID: US12193321B2
- Status: Granted
- Kind: B2
- Application number: 16/946,904
- Filed: 2020-07-10
- Published: 2021-01-14
- Granted: 2025-01-07
- Earliest claimed: 2019-07-10
- Assignees: Duk San Neolux Co., Ltd.
- Applicants: Duk San Neolux Co., Ltd.
- Inventors: Ki Ho So; Hyung Dong Lee; Dae Hwan Oh; Won Sam Kim; Byoung Yeop Kang
- Web page: https://patentgrep.com/patent/US12193321B2

## CPC

- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 411/12: linked by a chain containing hetero atoms as chain links
- C07D 411/14: containing three or more hetero rings
- C07D 471/06: Peri-condensed systems
- C07D 513/10: Spiro-condensed systems
- C09K 11/06: containing organic luminescent materials
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/15: Hole transporting layers
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- 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}
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Provided are a compound represented by Formula 1, an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, and an electronic device thereof, wherein by comprising compound represented by Formula 1 in the organic material layer, the driving voltage of the organic electric element can be lowered, and the luminous efficiency and life time, in particular, life time can be improved.

## Claims

### Claim 1

A compound of Formula 1:
wherein:
Ar1 to Ar6 are each independently selected from the group consisting of a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C3-C60 aliphatic ring group, -L′-N(Ra)(Rb), Formula A-1 and Formula A-2, and at least one of Ar1 to Ar6 is Formula A-1 or Formula A-2,
X1 is O or S,
X2 is N(R′), O or S,
R1 to R6 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano group, nitro group, a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C3-C60 aliphatic ring group, a C1-C30 alkyl group, a C2-C30 alkenyl group, a C2-C30 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxy group and -L′-N(Ra)(Rb), and adjacent groups together may be bonded to each other to form a ring,
n, p′ and r′ are each an integer of 0 to 3, m, o, p, q and r are each an integer of 0 to 4, and where they are each an integer of 2 to 4, each of R1s, each of R2s, each of R3s, each of R4s, each of R5s, or each of R6s is the same or different from each other,
x and y are each an integer of 0 to 2, and x+y is an integer greater than or equal to 1,
L1 to L3 and L′ are each independently selected from the group consisting of a single bond, a C6-C60 arylene group, a fluorenylene group, a C3-C60 aliphatic ring group and a C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P,
R′, Ra and Rb are each independently selected from the group consisting of a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P and a C3-C60 aliphatic ring group,
with the proviso that, in the case where L1 and L2 are each a single bond, X2 is O or S, and y is an integer of 1, at least one of R1 to R6 forms an aromatic hydrocarbon ring with an adjacent group, and
Ar1 to Ar6, R1 to R6, L1 to L3, R′ and the ring formed by adjacent groups may be each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C6-C20 aryloxy group, a C6-C20 arylthio group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C3-C20 aliphatic ring group, a C7-C20 arylalkyl group, and C8-C20 arylalkenyl group,
with the proviso that Formula 20 is excluded from Formula 1:
wherein X1, L1-L2, Ar1-Ar4, R1, and R2 are the same as defined for Formula 1, and a is an integer of 0 to 5 and m is an integer of 0 to 3.

### Claim 2 (depends on 1)

The compound of claim 1, wherein Formula 1 is represented by Formula 2 or Formula 3:
wherein X1, L1-L3, Ar1-Ar6, R1, R2, n and m are the same as defined in claim 1, and n is an integer of 0 to 3 in Formula 2 and an integer of 0 to 2 in Formula 3.

### Claim 3 (depends on 1)

The compound of claim 1, wherein Formula 1 is represented by one of Formula 4 to Formula 6, Formula 8, Formula 9, Formula 11 and Formula 14 to Formula 19:
wherein X1, L1-L3, Ar1-Ar6, R1, and R2, n and m are the same as defined in claim 1, n is an integer of 0 to 3 in Formulas 4 to 6, 8, 9 and 11 and an integer of 0 to 2 in Formulas 14 to 19, and m is an integer of 0 to 3 in Formulas 4 to 6, 8, 9 and 11 and an integer of 0 to 4 in Formulas 14 to 19.

### Claim 4 (depends on 1)

The compound of claim 1, wherein Formula 1 is represented by one of Formula 21 to Formula 34:
wherein X1, L1-L3, Ar1-Ar6, R1, and R2, n and m are the same as defined in claim 1, and a and b are each an integer of 0 to 6.

### Claim 5 (depends on 1)

The compound of claim 1, wherein at least one of L1 to L3 is a single bond.

### Claim 6

A compound selected from the group consisting of the following compounds:

### Claim 7 (depends on 1)

An organic electric element comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer comprises an emission-auxiliary layer, and wherein the emission-auxiliary layer comprises a single compound or a mixture of two or more compounds represented by Formula 1 of claim 1.

### Claim 8 (depends on 7)

The organic electric element of claim 7 further comprising a layer for improving luminous efficiency formed on one side of the anode and/or the cathode, the one side not facing the organic material layer.

### Claim 9 (depends on 7)

The organic electric element of claim 7, wherein the organic material layer further comprises at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport-auxiliary layer, an electron transport layer and an electron injection layer.

### Claim 10 (depends on 7)

The organic electric element of claim 7, wherein the organic material layer comprises two or more stacks and each of the stacks comprises a hole transport layer, the emission-auxiliary layer, a light emitting layer and an electron transport layer formed sequentially on the anode.

### Claim 11 (depends on 10)

The organic electric element of claim 10, wherein the organic electric element further comprises a charge generation layer formed between the stacks.

### Claim 12 (depends on 7)

An electronic device comprising a display device and a control unit for driving the display device, wherein the display device comprises the organic electric element of claim 7.

### Claim 13 (depends on 12)

The electronic device of claim 12, wherein the organic electric element is selected from the group consisting of an organic electroluminescent element, an organic solar cell, an organic photo conductor, an organic transistor, an element for monochromatic illumination and an element for quantum dot display.