# US 11,910,705 B2 · Compound for organic electric element, organic electric element using the same, and electronic device thereof

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- Number: US 11,910,705 B2
- Document ID: US11910705B2
- Status: Granted
- Kind: B2
- Application number: 16/344,684
- Filed: 2019-01-17
- Published: 2020-05-28
- Granted: 2024-02-20
- Earliest claimed: 2018-02-02
- Assignees: Duk San Neolux Co., Ltd.
- Applicants: Duk San Neolux Co., Ltd.
- Inventors: Hyun Ju Song; Ho Young Jung; Mi Young Chae; Jae Taek Kwon; Moo Jin Park; Sun Hee Lee
- Web page: https://patentgrep.com/patent/US11910705B2

## CPC

- C07D 209/82: Carbazoles; Hydrogenated carbazoles
- C07D 209/86: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07D 333/76: Dibenzothiophenes
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/10: linked by a carbon chain containing aromatic rings
- C07D 403/14: containing three or more hetero rings
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/10: linked by a carbon chain containing aromatic rings
- 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
- C07D 471/04: Ortho-condensed systems
- C09K 11/06: containing organic luminescent materials
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- 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 85/6572: {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 2211/1018: Heterocyclic compounds
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/155: comprising dopants
- H10K 50/181: {Electron blocking layers}
- H10K 71/164: {using vacuum deposition}
- H10K 2101/10: Triplet emission
- H10K 2101/40: Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
- H10K 2101/90: {Multiple hosts in the emissive layer}
- H10K 2102/351: {Thickness}
- 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 are a compound capable of improving luminous efficiency, stability and lifetime of an organic electronic device, an organic electric element using the same, and an electronic device comprising the element.

## Claims

### Claim 1

A compound represented by Formula (1) any of Formulas 8 to 10:
wherein:
1) Ar1, Ar2 and Ar3 are each independently a C6-C25 aryl group,
2) l, e, d, and m are each an integer of 0 to 4, wherein l+e is an integer of 0 to 4, d+m is an integer of 0 to 4, a and b are an integer of 0 to 3,
3) R1, R2, and R4 are each independently selected from the group consisting of hydrogen; deuterium; halogen; a C6-C25 aryl group; a fluorenyl group; a C2-C25 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C3-C25 aliphatic ring and a C6-C25 aromatic ring; a C1- C25 alkyl group; a C2-C20 alkenyl group; and a C2-C20 alkynyl group; or a plurality of R1, a plurality of R2, and a plurality of R4 may be bonded to each other to form a C6-C25 aromatic ring,
4) R5 is hydrogen,
wherein, the aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, fused ring group, alkyl group, and alkenyl group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; silane group; cyano group; nitro group; C1-C20 alkoxyl group; C1-C20 alkyl group; C2-C20 alkenyl group; C6-C20 aryl group; C6-C20 aryl group substituted with deuterium; a fluorenyl group; C2-C20 heterocyclic group; and C3-C20 cycloalkyl group.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein at least one of Ar1 and Ar2 in the formulas is a C6-C24 aryl group.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein Ar1 or Ar3 in the formulas is a C6-C24 aryl group.

### Claim 4 (depends on 1)

A compound of claim 1 selected from the group consisting of the following compounds:

### Claim 5 (depends on 1)

An organic electronic element comprising a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode and comprising a compound of Formula (8), (9), or (10) according to claim 1.

### Claim 6 (depends on 5)

The organic electronic element according to claim 5, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, an emitting auxiliary layer, an 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 emitting auxiliary layer, the emitting layer, the electron transport auxiliary layer, the electron transport layer and the electron injection layer comprises one or more of the compounds of Formula (8), (9), or (10).

### Claim 7 (depends on 6)

The organic electronic element according to claim 6, wherein the compound is included in the emitting layer.

### Claim 8 (depends on 7)

The organic electronic element according to claim 7, further comprising a compound represented by Formula (12) in the emitting layer:
wherein:
1) Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, z10, z11, z12, z13, z14, z15 and Z16 are each independently CR or N, wherein R is hydrogen; a C6-C60 aryl group; a C3-C60 heterocyclic group including at least one heteroatom of O, N, S, Si, or P; a C1-C50 alkyl group; a C6-C60 arylamine group; a fluorenyl group; and may form a ring by combining with neighboring groups,
2) L2 is selected from the group consisting of a single bond; a C6-C60 arylene group; a C3-C60 heteroarylene group; and a divalent aliphatic hydrocarbon group,
3) W is NAr5, O, S or CR′R″, wherein R′ and R″ are each independently selected from the group of a C1-C50 alkyl group; a C6-C60 aryl group; a C3-C60 heterocyclic group including at least one heteroatom of O, N, S, Si, or P; and R′ and R″ may be bonded to each other to form a spiro ring, and
4) Ar4 and Ar5 are each independently selected from the group consisting of a C6-C60 aryl group; a C3-C60 heterocyclic group including at least one heteroatom of O, N, S, Si, or P; a C1-C50 alkyl group; a C6-C60 arylamine group; a fluorene group.

### Claim 9 (depends on 8)

The organic electronic element according to claim 8, wherein Formula (12) is any one of the following Formulas (13) to (16):
wherein Ar4, Ar5, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z12, Z13, Z14, Z15, Z16, L2, R′, R″ are the same as defined in claim 8.

### Claim 10 (depends on 8)

The organic electronic element according to claim 8, wherein both Ar4 and Ar5 in Formula (12) are a C6-C30 aryl group.

### Claim 11 (depends on 1, 8)

The organic electronic element according to claim 8, wherein the compound represented by Formula (12) is a compound represented by Formula (17):
wherein:
Ar4, Ar5, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z12, Z13, Z14, Z15, Z16, and L2 are the same as defined in claim 8,
1) L1 is selected from the group consisting of a single bond; a C6-C60 arylene group; a C3-C60 heteroarylene group; and a divalent aliphatic hydrocarbon group,
2) Y is O, S or NAr5,
3) Ra and Rb 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 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); or a plurality of Ra or a plurality of Rb may be bonded to each other to form an aromatic ring or and heteroaromatic ring,
wherein, L′ may be 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; and the 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 including at least one heteroatom of O, N, S, Si, or P; or a plurality of Ra or a plurality of Rb may be bonded to each other to form an aromatic ring or and heteroaromatic ring, and
4) y is an integer of 0 to 3, z is an integer of 0 to 4.

### Claim 12 (depends on 8)

The organic electronic element according to claim 8, wherein the compound represented by Formula (12) is any one of the following compounds:

### Claim 13 (depends on 1, 2)

An organic electronic element comprising an anode; a cathode; an organic material layer formed between the anode and the cathode,
wherein the organic material layer includes an emitting layer, an hole transport layer formed between the anode and the emitting layer; an emitting auxiliary layer formed between the emitting layer and the hole transport layer;
wherein the hole transport layer or the emitting auxiliary layer comprises a compound represented by Formula (18), and wherein the emitting layer comprises a compound represented by any of Formulas (8) to (10) of claim 1:
wherein:
1) Ar1, Ar2, Ar3, l, m, a, b, d, e, R1, R2, R4 and R5 are the same as defined in claim 1,
2) Ar4 and Ar5 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 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 group; 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 including at least one heteroatom of O, N, S, Si, or P; or Ar4 and Ar5 may be bonded to each other to form a ring,
3) Ar6 is selected from the group consisting of 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; or is at least one of the following Formulas (1-a), (1-b), (1-c):
4) Ar9, Ar10 and Ar11 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 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-C60 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),
5) h, i, and g are an integer of 0 to 4; j is an integer of 0 to 3; and R6, R7, R8 and R9 are the same or different from each other, and 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 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 in case g, h, i, j are 2 or more, R6, R7, R8 and R9 are each in plural being the same or different and may be bonded to each other to form a ring,
6) L6 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 including at least one heteroatom of O, N, S, Si or P, and
7) L5 is selected from the group consisting of 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 including at least one heteroatom of O, N, S, Si or P.

### Claim 14 (depends on 13)

The organic electronic element according to claim 13, further comprising at least one of the compounds represented by Formula (12) in the emitting layer:
wherein:
1) Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z12, Z13, Z14, Z15 and Z16 are each independently CR or N, wherein R is hydrogen; a C6-C60 aryl group; a C3-C60 heterocyclic group including at least one heteroatom of O, N, S, Si, or P; a C1-C50 alkyl group; a C6-C60 arylamine group; a fluorene group; and is possible to form a ring by combining with neighboring groups,
2) L2 is selected from the group consisting of a single bond; a C6-C60 arylene group; a C3-C60 heteroarylene group; and a divalent aliphatic hydrocarbon group,
3) W is NAr5, O, S or CR′R″, wherein R′ and R″ are each independently a C1-C50 alkyl group; a C6-C60 aryl group; a C3-C60 heterocyclic group including at least one heteroatom of O, N, S, Si, or P; and R′ and R″ may be bonded to each other to form a spiro ring, and
4) Ar4 and Ar5 are each independently selected from the group consisting of a C6-C60 aryl group; a C3-C60 heterocyclic group including at least one heteroatom of O, N, S, Si, or P; a C1-C50 alkyl group; a C6-C60 arylamine group; a fluorene group.

### Claim 15 (depends on 13)

The organic electronic element according to claim 13, wherein the hole transport layer comprises a compound represented by Formula(19) or Formula(20), and the emitting auxiliary layer comprises a compound represented by Formula(21) or Formula(22):
wherein:
1) Ar6 is selected from the group consisting of 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, and
2) Ar4, Ar5, Arg, Ar9, Ar10, Ar11, h, i, g, L5, L6, R6, R7, R8 and R9 are the same as defined in claim 13.

### Claim 16 (depends on 13)

The organic electronic element according to claim 13, wherein the compound represented by Formula (18) is one of the following compounds:

### Claim 17 (depends on 13)

The organic electronic element according to claim 13, wherein the compounds represented by Formula (8), (9) or (10) and Formula (18) are in a ratio of 1:9 to 9:1.

### Claim 18 (depends on 13)

The organic electronic element according to claim 13, wherein the compound represented by Formula (8), (9) or (10) is included in the emitting layer as a phosphorescent host material.

### Claim 19 (depends on 13)

The organic electronic element according to claim 13, further comprising a light efficiency enhancing layer formed on at least one of the opposite sides to the organic material layer among one side of the first electrode and of the second electrode.

### Claim 20 (depends on 13)

The organic electronic element according to claim 13, 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.

### Claim 21 (depends on 5)

A display device comprising the organic electronic element of claim 5; and a control part driving the display device.

### Claim 22 (depends on 21)

A display device according to claim 21, wherein the organic electronic element is an OLED, an organic solar cell, an organic photo conductor(OPC), organic transistor(organic TFT), or an element for monochromic or white illumination.

### Claim 23 (depends on 13)

A display device comprising the organic electronic element of claim 13; and a control part driving the display device.

### Claim 24 (depends on 23)

A display device according to claim 23, wherein the organic electronic element is an OLED, an organic solar cell, an organic photo conductor(OPC), organic transistor(organic TFT), or an element for monochromic or white illumination.