# US 2017/0288148 A1 · Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof

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- Number: US 2017/0288148 A1
- Document ID: US20170288148A1
- Status: Published application
- Kind: A1
- Application number: 15/475,697
- Filed: 2017-03-31
- Published: 2017-10-05
- Earliest claimed: 2016-04-01
- Assignees: Duk San Neolux Co., Ltd.
- Applicants: Duk San Neolux Co., Ltd.
- Inventors: Jonggwang PARK; Yeon Hee CHOI; Yun Suk LEE; Kiho SO; Hyoung Keun PARK; Yeonseok JEONG; Hak Young LEE
- Web page: https://patentgrep.com/patent/US20170288148A1

## CPC

- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- 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
- C07D 487/06: Peri-condensed systems
- C09K 11/06: containing organic luminescent materials
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/342: {comprising iridium}
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/655: {comprising only sulfur as heteroatom}
- 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}
- C09K 2211/1022: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1037: with sulfur
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1088: containing oxygen as the only heteroatom
- C09K 2211/1092: containing sulfur as the only heteroatom
- H10K 50/15: Hole transporting layers
- H10K 50/156: {comprising a multilayered structure}
- 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 of Formula 1 and 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 electronic device comprising the organic electric element, wherein the driving voltage of the organic electronic device can be lowered, and the luminous efficiency and life span can be improved by comprising the compound represented by Formula 1 in the organic material layer.

## Claims

### Claim 1

A compound of Formula 1:
Wherein,
L is C6-C60 arylene group,
L2 and L3 are each independently selected from the group consisting of a single bond; a C6-C60 arylene group; a fluorenylene group; a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and a fused ring formed by a C6-C60 aromatic ring and a C3-C60 aliphatic ring,
Ar1 to Ar5 are each independently selected from the group consisting of a C6-C60 aryl group; a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Se, Si and P; a fluorenyl group; a fused ring formed by a C6-C60 aromatic ring and a C3-C60 aliphatic ring; a C1-C50 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C30 alkoxy group; and a C6-C30 aryloxy group, with the proviso that carbazole is excluded from Ar2 and Ar3,
“m” and “n” are each an integer of 0 to 3,
R1 and R2 are each independently selected from the group consisting of deuterium; tritium; halogen; a cyano group; a nitro group; a C6-C60 aryl group; a fluorenyl group; a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Se, Si and P; a fused ring formed by a C6-C60 aromatic ring and a C3-C60 aliphatic ring; a C1-C50 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C30 alkoxy group; and a C6-C30 aryloxy group,
when “m” and “n” are each an integer of 2 or more, a plurality of R1s and R2s may be each the same or different from each other, and neighboring R1s and/or neighboring R2s may be linked to each other to form a ring, and
Ar1˜Ar5, R1, R2, L1˜L3, a ring formed by linking between neighboring R1s, and a ring formed by linking between neighboring R2s may be each substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane group substituted or unsubstituted with a C1-C20 alkyl group or a C6-C20 aryl group; a phosphine oxide group substituted or unsubstituted 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 alkoxy 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 with deuterium; a fluorenyl group; a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Se, Si and P; a C3-C20 cycloalkyl group; a C7-C20 arylalkyl group; —N(Ra)(Rb); a C8-C20 arylalkenyl group; and
wherein 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 selected from the group consisting of O, N, S, Se, Si and P, and Ra and Rb may be each substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane group substituted or unsubstituted 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 alkoxy 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 with deuterium; a fluorenyl group; a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Se, Si and P; a C3-C20 cycloalkyl group; a C7-C20 arylalkyl group; and a C8-C20 arylalkenyl group.

### Claim 2 (depends on 1)

The compound of claim 1, wherein Formula 1 is represented by one of Formulas 2 to 5 below:
in formulas 2 to 5, Ar1˜Ar5, R1, R2, L1˜L3, m and n are each the same as defined in claim 1.

### Claim 3 (depends on 1)

The compound of claim 1, wherein Formula 1 is represented by one of Formulas 6 to 10 below:
in formulas 6 to 10, Ar1˜Ar5, R1, R2, L1˜L3, m and n are each the same as defined in claim 1.

### Claim 4 (depends on 1)

The compound of claim 1, L1 is represented by one of Formulas L1-1 to L1-7 below:
in formulas L1-1 to L1-7,
“a” to “c” are each an integer of 0 to 4, “d” is an integer of 0 to 6, “e” is an integer of 0 to 5, “f” and “g” are each an integer of 0 to 3, and
R3 to R5 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 selected from the group consisting of O, N, S, Si and P; a fused ring formed by a C6-C60 aromatic ring and a C3-C60 aliphatic ring; a C1-C50 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C30 alkoxy group; and a C6-C30 aryloxy group, and a plurality of R3s to R5s may be each the same or different from each other when “a” to “g” are each an integer of 2 or more.

### Claim 5 (depends on 1)

The compound of claim 1, one of Ar1 to Ar5 is represented by Formula 11 below:
in formula 11,
X is S, Se, 0, C(Rc)(Rd) or N(Re) when at least one of Ar1, Ar4 and Ar5 is Formula 11, and X is S, Se, O or C(Rc)(Rd) when at least one of Ar2 and Ar3 is Formula 11,
Rc to Re 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 selected from the group consisting of O, N, S, Si and P; a fused ring formed by a C6-C60 aromatic ring and a C3-C60 aliphatic ring; a C1-C50 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C30 alkoxy group; and a C6-C30 aryloxy group, and Rc and Rd may be linked to each other to form a spiro compound,
L4 is selected from the group consisting of a single bond; a C6-C60 arylene group; a fluorenylene group; a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and a fused ring formed by a C6-C60 aromatic ring and a C3-C60 aliphatic ring,
“o” is an integer of 0 to 3, “p” is an integer of 0 to 4, R6 and R7 are each independently selected from the group consisting of deuterium; tritium; halogen; a cyano group; a nitro group; a C6-C60 aryl group; a fluorenyl group; a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; a fused ring formed by a C6-C60 aromatic ring and a C3-C60 aliphatic ring; a C1-C50 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C30 alkoxy group; and a C6-C30 aryloxy group, and
when “o” and “p” are each an integer of 2 or more, a plurality of R6s and R7s may be each the same or different from each other, and adjacent R6s and/or adjacent R6s may be linked to each other to form a ring.

### Claim 6 (depends on 5)

The compound of claim 5, at least one of Ar1, Ar2 and Ar5 is the above Formula 11, wherein X is S.

### Claim 7 (depends on 1)

The compound of claim 1, wherein Formula 1 is any one of the compounds below:

### Claim 8 (depends on 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, wherein the organic material layer comprises the compound of claim 1.

### Claim 9 (depends on 8)

The organic electric element of claim 8, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, an emission-auxiliary layer, an light emitting layer, an electron transport-auxiliary layer, an electron transport layer and an electron injection layer, and at least one of the hole injection layer, the hole transport layer, the emission-auxiliary layer, the light emitting layer, the electron transport-auxiliary layer, the electron transport layer and the electron injection layer contains the compound as a single compound or a mixture of two or more different kinds.

### Claim 10 (depends on 9)

The organic electric element of claim 9, wherein the organic layer comprises the light emitting layer and the emission-auxiliary layer, and the light emitting layer includes a phosphorescent red light emitting material, and the compound is contained in the emission-auxiliary layer.

### Claim 11 (depends on 8)

The organic electric element of claim 8, wherein the organic material layer is formed by any one of the processes of spin coating, nozzle printing, inkjet printing, slot coating, dip coating and roll-to-roll.

### Claim 12 (depends on 8)

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 8.

### Claim 13 (depends on 12)

The electronic device of claim 12, wherein the organic electric element comprises at least one of an organic light emitting diode, an organic solar cell, an organic photo conductor, an organic transistor, and an element for monochromatic or white illumination.