# US 11,299,452 B2 · Compound for organic electronic device, organic electronic device using same, and electronic apparatus thereof

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- Number: US 11,299,452 B2
- Document ID: US11299452B2
- Status: Granted
- Kind: B2
- Application number: 16/302,920
- Filed: 2017-05-18
- Published: 2019-06-20
- Granted: 2022-04-12
- Earliest claimed: 2016-05-19
- Assignees: Duk San Neolux Co., Ltd.
- Applicants: Duk San Neolux Co., Ltd.
- Inventors: Mun Jae Lee; Soung Yun Mun; Jae Taek Kwon; Dae Sung Kim; Moo Jin Park; Chi Hyun Park; Sun Hee Lee; Hyun Ju Song; Bum Sung Lee
- Web page: https://patentgrep.com/patent/US11299452B2

## CPC

- C07C 211/54: having amino groups bound to two or three six-membered aromatic rings
- C07C 211/58: Naphthylamines; N-substituted derivatives thereof
- C07D 209/80: [b, c]- or [b, d]-condensed
- C07D 307/77: ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07D 333/50: condensed with carbocyclic rings or ring systems
- C07D 333/76: Dibenzothiophenes
- C07D 401/14: containing three or more hetero rings
- 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 405/12: linked by a chain containing hetero atoms as chain links
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 409/14: containing three or more hetero rings
- C07D 471/04: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D 491/048: the oxygen-containing ring being five-membered
- C07D 495/04: Ortho-condensed systems
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C09K 11/06: containing organic luminescent materials
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- 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 85/342: {comprising iridium}
- H10K 2101/10: Triplet emission
- H10K 2101/90: {Multiple hosts in the emissive layer}
- Y02E 10/549: Organic PV cells
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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 an organic electric element comprising as a phosphorescent host material, a mixture of the compounds of Formula (1) and Formula (2), and an organic electronic device or apparatus thereof for achieving a high luminous efficiency, a low driving voltage, and an improved lifespan.

## Claims

### Claim 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 an emitting layer, and the emitting layer is a phosphorescent light emitting layer comprising a first host compound represented by Formula (1) and a second host compound represented by Formula (2):
wherein:
1) Ar1, Ar2, Ar3 and Ar4 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 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;
2) c and e are each independently integers of 0 to 10, d is an integer of 0 to 2, and R3, R4 and R5 are, being the same or different from each other, 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 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-C60 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), wherein in case c and e are 2 or more, R3, R4 and R5 are each in plural being the same or different and a plurality of R3 or a plurality of R4 or a plurality of R5 combine to each other to form a ring;
3) L1, L2, L3 and L4 are each independently selected from the group consisting of a single bond; a C6-C60 arylene group; and 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;
4) A and B are each independently a C6-C20 aryl group or a C2-C20 heterocyclic group;
5) i and j are each independently 0 or 1, wherein i+j is 1 or more, and where i or j is 0, it means a direct bond,
6) X1 and X2 are each independently O, S, or CR′R″, wherein R′ and R″ are each 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 combine to each other to form a spiro ring,
wherein the aryl group, fluorenyl group, arylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group may be 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 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 of thereof, and
wherein the compound of Formula (2) excludes a compound wherein both A and B are a C6 aryl group.

### Claim 2 (depends on 1)

The organic electric element according to claim 1, wherein the first host compound represented by Formula (1) is represented by any one of the following Formulas (3) to (5):
wherein:
1) L1, L3, L4, Are and Ara are the same as defined in the claim,
2) X3 is O or S,
3) a is an integer of 0 to 4, b is an integer of 0 to 3, and R1 and R2 are the same or different from each other and 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 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); or in case a and b are 2 or more, R1 and R2 are each in plural being the same or different, and a plurality of R1 or a plurality of R2 combine to each other to form a ring.

### Claim 3 (depends on 1)

The organic electric element according to claim 1, wherein the compound represented by Formula (1) is represented by any one of the following Formulas (6) to (14):
wherein:
1) L1, L3, L4, Are and Ara are the same as defined in the claim,
2) a is an integer of 0 to 4, b is an integer of 0 to 3, and R1 and R2 are the same or different from each other, and 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 and P; a fused ring group of a C3-C6o 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 in case a and b are 2 or more, R1 and R2 are each in plural being the same or different, and a plurality of R1 or a plurality of R2 combine to each other to form a ring.

### Claim 4 (depends on 1, 2)

The organic electric element according to claim 1, wherein the first host compound represented by Formula (1) is represented by any one of the following Formulas (15) to (23):
wherein:
1) L1, L3, L4, Ar2 and Ara are the same as defined in claim 1,
2) a is an integer of 0 to 4, b is an integer of 0 to 3, and R1 and R2 are the same or different from each other, and 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 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); or in case a and b are 2 or more, R1 and R2 are each in plural being the same or different, and a plurality of R1 or a plurality of R2 combine to each other to form a ring.

### Claim 5 (depends on 1)

The organic electric element according to claim 1, wherein Ar1, Ar2 and Ar3 in Formula (1) are all C6-C24 aryl groups, and L1, L3 and L4 are single bonds or all C6-C24 aryl groups.

### Claim 6 (depends on 1, 2)

The organic electric element according to claim 1, wherein the compound represented by Formula (1) is represented by any one of the following Formulas (24) to (26):
wherein:
1) L1, L3, L4, Are and Ar3 are the same as defined in claim 1,
2) Ar5 and Ar6 are each independently selected from the group consisting of a C6-C60 aryl group; a C2-C60 heterocyclic group including at least one heteroatom of O, N, S, Si and P; a fused ring group of a C3-C60 aliphatic ring and a C3-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).

### Claim 7 (depends on 1)

The organic electric element according to claim 1, wherein L1, L3 and L4 in Formula (1) are each selected from the group consisting of the following Formulas (A-1) to (A-12):
wherein:
1) a′, c′, d′ and e′ are each independently integers of 0 to 4; b′ is an integer of 0 to 6; f′ and g′ are each independently integers of 0 to 3; and h′ is an integer of 0 to 1,
2) R6, R7 and R8 are the same or different from each other, and 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 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-C60 aryloxy group; and -L′-N(Ra)(Rb); or in case f ‘and g’ are 2 or more, 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 adjacent R6 and R7 may combine 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 the same as defined in the claim,
4) Z1, Z2 and Z3 are each independently CR′ or N, wherein at least one is N.

### Claim 8 (depends on 1)

The organic electric element according to claim 1, wherein at least one of L1, L3, and L4 in Formula (1) is substituted on a m(meta)-position.

### Claim 9 (depends on 1)

The organic electric element according to claim 1, wherein the second host compound represented by Formula (2) comprises a compound represented by the following Formula (27) or (28):
wherein R3, R4, R5, Ar4, L2, c, d, e, A, B, X1 and X2 are the same as defined in the claim.

### Claim 10 (depends on 1)

The organic electric element according to claim 1, wherein A and B in Formula (2) are selected from the group consisting of the following Formulas (B-1) to (B-7):
wherein:
1) Z4 to Z50 are each independently CR′ or N,
2) R′ is the same as defined in the claim,
3) * indicates the position to be condensed.

### Claim 11 (depends on 1)

The organic electric element according to claim 1, wherein the second host compound represented by Formula (2) includes a compound represented by any of the following Formulas (29) to (48):
wherein Ar4, L2, X1, X2, R3, R4, R5, c, d, and e are the same as defined in the claim.

### Claim 12 (depends on 1)

The organic electric element according to claim 1, wherein the second host compound represented by Formula (2) comprises any of compounds represented by the following Formulas (49) to (56):
wherein R3, R4, R5, L2, Ar4, c, d, e, A, B, R′ and R″ are the same as defined in the claim.

### Claim 13 (depends on 1)

The organic electric element according to claim 1, wherein the first host compound represented by Formula (1) is one of the following Compounds 1-1′ to 1-82′:

### Claim 14 (depends on 1)

The organic electric element according to claim 1, wherein the second host compound represented by Formula (2) is one of the following compounds:

### Claim 15 (depends on 1)

The organic electronic element of claim 1, further comprising at least one hole transporting band layer between the first electrode and the emitting layer, wherein the hole transporting band layer includes a hole transport layer, an emitting auxiliary layer, or both the layers, and the hole transporting band layer includes a compound represented by Formula (1).

### Claim 16 (depends on 1)

The organic electric element according to claim 1, wherein the compounds represented by Formula (1) and (2) are mixed in a ratio of 1:9 to 9:1 to be included in the emitting layer.

### Claim 17 (depends on 1)

The organic electric element according to claim 1, wherein the compound represented by Formula (1) and (2) are mixed in a ratio of 1:9 to 5:5 to be included in the emitting layer.

### Claim 18 (depends on 1)

The organic electric element according to claim 1, wherein the compound represented by Formula (1) and (2) are mixed in a ratio of 2:8 or 3:7 to be included in the emitting layer.

### Claim 19 (depends on 1)

A display device comprising the organic electric element of claim 1 and a control part driving the display device.

### Claim 20 (depends on 19)

A display device according to claim 19, 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.