# US 11,309,496 B2 · Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof

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- Number: US 11,309,496 B2
- Document ID: US11309496B2
- Status: Granted
- Kind: B2
- Application number: 16/900,172
- Filed: 2020-06-12
- Published: 2020-10-22
- Granted: 2022-04-19
- Earliest claimed: 2014-01-16
- Assignees: Duk San Neolux Co., Ltd.
- Applicants: Duk San Neolux Co., Ltd.
- Inventors: Yu Ri Kim; Sun-Hee Lee; Won Sam Kim; Hye Ryeong Kim; Ho Young Jung; Jung Hwan Park; Sun Pil Hwang
- Web page: https://patentgrep.com/patent/US11309496B2

## CPC

- C07D 495/14: Ortho-condensed systems
- C07D 491/14: Ortho-condensed systems
- C07D 491/147: the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
- C09K 11/06: containing organic luminescent materials
- H05B 33/20: characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
- 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 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- 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 2211/1092: containing sulfur as the only heteroatom
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/17: Carrier injection layers
- H10K 71/135: {using ink-jet printing}
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/342: {comprising iridium}
- H10K 2101/10: Triplet emission
- Y02E 10/549: Organic PV cells
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

A compound represented by Formula 1 is disclosed. An organic electric element includes a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode. The organic material layer includes the compound represented by Formula 1. When the organic electric element includes the compound in the organic material layer, luminescence efficiency, stability, and life span can be improved.

## Claims

### Claim 1

A compound of Formula 1:
wherein:
Z is S,
one of X, Y, V and W is N(R6), and the other three of X, Y, V and W are each independently S or O,
m, n, o and p are each independently an integer of 0 or 1, with the proviso that m+n is 1 or more and o+p is 1 or more,
R1 to R4 are each independently selected from the group consisting of deuterium; halogen; 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 group formed by a C3-C60 aliphatic ring with 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; -L′-N(Ar1)(Ar2); and a combination thereof,
a and d are each an integer of 0 to 4, b and c are each an integer of 0 to 2, and where a, b, c or d is 2 or more, two adjacent groups of R1s, R2s, R3s or R4s are optionally linked together to form a ring,
R6 is selected from the group consisting of a fluorenyl group; a C8-C60 heterocyclic group containing a quinazolinyl group; and -L′-N(Ar1)(Ar2), with the proviso that where L′ is a single bond or a C6 aryl group in the -L′-N(Ar1)(Ar2), at least one of Ar1 a Ar2 is a fluorenyl group or a C2-C60 heterocyclic group;
L′ is selected from the group consisting of a single bond; a C6-C60 arylene group; a fluorenylene group; a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring; a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and a combination thereof, wherein, L′ may be optionally substituted by one or more substituents selected from the group consisting of deuterium; halogen; a silane 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, Si, and P; a C3-C20 cycloalkyl group; a C7-C20 arylalkyl group; and a C8-C20 arylalkenyl group,
Ar1 and Ar2 are each independently selected from the group consisting of a C6-C60 aryl group; a fluorenyl group; a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring; a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and a combination thereof, and
where R1 to R4, Ar1 and Ar2 are the aryl, fluorenyl, heterocyclic ring or fused ring, and where R6 is the fluorenyl or heterocyclic ring each of the R1 to R4 and R6, Ar1, and Ar2 is optionally substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane 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, Si, and P; a C3-C20 cycloalkyl group; a C7-C20 arylalkyl group; and a C8-C20 arylalkenyl group.

### Claim 2

A compound of Formula 1:
wherein:
Z is N(R5),
X, Y, V and W are each independently N(R6), S or O, with the proviso that: at least one of X, Y, V and W is not N(R6), and where both n and o are 0 (zero), at least one of Y and V is not N(R6),
m, n, o and p are each independently an integer of 0 or 1, with the proviso that m+n is 1 or more and o+p is 1 or more,
R1 to R4 are each independently selected from the group consisting of deuterium; halogen; 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 group formed by a C3-C60 aliphatic ring with 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; -L-N(Ar1)(Ar2); and a combination thereof,
a and d are each an integer of 0 to 4, b and c are each an integer of 0 to 2, and where a, b, c or d is 2 or more, two adjacent groups of R1s, R2s, R3s or R4s are optionally linked together to form a ring except for a heterocyclic group containing O,
R5 is a C2-C60 heterocyclic group containing a quinazolinyl group,
R6 is selected from the group consisting of a C6-C60 aryl group; a fluorenylene group; or 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 group formed by a C3-C60 aliphatic ring with 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; -L′-N(Ar1)(Ar2); and a combination thereof,
L′ is selected from the group consisting of a single bond; a C6-C60 arylene group; a fluorenylene group; a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring; a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and a combination thereof,
Ar1 and Ar2 are each independently selected from the group consisting of a C6-C60 aryl group; a fluorenyl group; a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring; a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and a combination thereof,
with the proviso that where X, Y, V and W are each 0 or S, the R5 is a C10-C60 fused aryl group, a fluorenyl group, a C8 heterocyclic group, or -L′-N(Ar1)(Ar2), wherein where L′ is a single bond or a C6 arylene group, at least one of Ar1 and Ar2 is selected from the group consisting of a C10-C60 aryl group, a fluorenyl group; a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring; a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and a combination thereof, and
where R1 to R4 and R6, L′, Ar1 and Ar2 are the aryl, fluorenyl, heterocyclic ring or fused ring, and where R5 is the fluorenyl or heterocyclic group, each of the R1 to R6, Ar1, and Ar2, is optionally substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane 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, Si, and P; a C3-C20 cycloalkyl group; a C7-C20 arylalkyl group; and a C8-C20 arylalkenyl group.

### Claim 3 (depends on 1)

The compound of claim 1 represented by one of Formulas 2 to 4:
wherein V, W, X, Y, Z, R1 to R4, a, b, c and d are defined the same as in claim 1.

### Claim 4 (depends on 2)

The compound of claim 2 represented by one of Formulas 2 to 4:
wherein V, W, X, Y, Z, R1 to R4, a, b, c and d are defined the same as in claim 2.

### Claim 5

A compound selected from the group consisting of:

### Claim 6 (depends on 1)

An organic electric element comprising a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode and comprising one or more of the compounds of claim 1.

### Claim 7 (depends on 2)

An organic electric element comprising a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode and comprising one or more of the compounds of claim 2.

### Claim 8 (depends on 5)

An organic electric element comprising a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode and comprising one or more of the compounds of claim 5.

### Claim 9 (depends on 6)

The organic electric element of claim 6, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, an emission-auxiliary layer and a light emitting layer.

### Claim 10 (depends on 7)

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

### Claim 11 (depends on 6)

The organic electric element of claim 6, wherein the organic electric element further comprises a luminescence efficiency-improving layer formed on the surface of the first and/or the second electrodes not contacting the organic material layer.

### Claim 12 (depends on 7)

The organic electric element of claim 7, wherein the organic electric element further comprises a luminescence efficiency-improving layer formed on the surface of the first and/or the second electrodes not contacting the organic material layer.

### Claim 13 (depends on 6)

An electronic device comprising a display device, which comprises the organic electric element of claim 6, and a control unit for driving the display device.

### Claim 14 (depends on 7)

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

### Claim 15 (depends on 8)

An electronic device comprising a display device, which comprises the organic electric element of claim 8, and a control unit for driving the display device.

### Claim 16 (depends on 14)

The electronic device of claim 14, 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.

### Claim 17 (depends on 15)

The electronic device of claim 15, 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.