# US 2021/0242410 A1 · Compound for organic electric element, organic electric element using the same, and electronic device thereof

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- Number: US 2021/0242410 A1
- Document ID: US20210242410A1
- Status: Published application
- Kind: A1
- Application number: 17/213,157
- Filed: 2021-03-25
- Published: 2021-08-05
- Earliest claimed: 2016-03-16
- 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; Sun Hee LEE; Sun Pil HWANG; Ho Young JUNG; Bum Sung LEE
- Web page: https://patentgrep.com/patent/US20210242410A1

## CPC

- C07D 487/04: Ortho-condensed systems
- C07D 209/56: Ring systems containing three or more rings
- C07D 209/80: [b, c]- or [b, d]-condensed
- 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 209/88: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- 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 405/12: linked by a chain containing hetero atoms as chain links
- 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 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 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/636: {comprising heteroaromatic 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}
- C09K 2211/1018: Heterocyclic compounds
- C09K 2211/1022: bridged by heteroatoms, e.g. N, P, Si or B
- H10K 10/40: Organic transistors
- H10K 30/50: Photovoltaic [PV] devices
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/12: comprising dopants
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 50/17: Carrier injection layers
- H10K 50/171: {Electron injection layers}
- H10K 50/18: Carrier blocking layers
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- 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}
- H10K 2101/10: Triplet emission
- H10K 2101/90: {Multiple hosts in the emissive layer}
- 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 is an organic electric element and an electronic device thereof, by using the mixture of the compounds as a phosphorescent host material, it is possible to achieve a high luminous efficiency and a low driving voltage of an organic electric element, and the life span of the device can be greatly improved.

## 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 24:
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 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; and a C6-C30 aryloxy group;
2) a is an integer of 0 to 4, and b is an integer of 0 to 3, and c and e are an integer of 0 to 10, and d is an integer of 0 to 2,
3) R1, R2, 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 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; and a C6-C30 aryloxy group; or in case a, b, c, and e are 2 or more, d is 2, R1, R2, R3, R4 and R5 are each in plural and are the same or different, and a plurality of R1 or a plurality of R2 or a plurality of R3 or a plurality of R4 or a plurality of R5 may be bonded to each other to form a ring,
4) L1 and L2 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,
5) A and B are each independently a C6-C60 aryl group or a C2-C20 heterocyclic group, wherein where both A and B are a substituted or unsubstituted C6 aryl group (phenyl group), d is 2 and R4s are bonded to each other to form an aromatic or heteroaromatic ring,
6) X2 is NR′, O, S, or CR′R″, wherein R′ and R″ are independently hydrogen; a C6-C60 aryl group; a fluorenyl group; a C3-C60 heterocyclic group; or a C1-C50 alkyl group, wherein R′ and R″ may be bonded to each other to form a spiro ring,
7) n is an integer of 1 or 2, and when n is 2, two Ar2 are the same or different, and two Ar3 are each the same or different,
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; 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; and C2-C20 heterocyclic group; wherein the substituents may combine each other and form a saturated or unsaturated ring, wherein the term ‘ring’ means a C3-C60 aliphatic ring or a C6-C60 aromatic ring or a C2-C60 heterocyclic ring or a fused ring formed by the combination thereof.

### Claim 2 (depends on 1)

The organic electric element of claim 1, wherein the first host compound of Formula 1 is represented by Formula 3 or Formula 4:
wherein R1, R2, Ar1, Ar2, Ar3, a and b are the same as defined in claim 1.

### Claim 3 (depends on 1)

The organic electric element of claim 1, wherein L1 and L2 are selected from the group consisting of Formulas (A-1) to (A-12):
wherein
1) a′, c′, d′ and e′ are an integer of 0 to 4, and b′ is an integer of 0 to 5, and f′ and g′ are an integer of 0 to 3, and h′ is an integer of 0 to 1,
2) R6, R7 and R8 are the same or different, 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 or 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; and a C6-C30 aryloxy group; or when e′, f′ and g′ are 2 or more, they are the same as or different from each other, and a plurality of R6 or a plurality of R7 or plurality of R8 may be bonded to each other to form an aromatic or a heteroaromatic ring, or two adjacent R6 and R7, or R7 and R8 may be bonded to form an aromatic or heteroaromatic ring,
3) Y is NR′, O, S or CR′R″,
4) Z1, Z2 and Z3 are independently CR′ or N and at least one of Z1, Z2 and Z3 is N. and
5) R′ and R″ are independently hydrogen; a C6-C60 aryl group; a fluorenyl group; a C3-C60 heterocyclic group; or a C1-C50 alkyl group, wherein R′ and R″ may be bonded to each other to form a spiro ring.

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

The organic electric element of claim 1, wherein the first host compound of Formula 1 is represented by one of Formulas 5 to 8:
wherein
1) R1, R2, Ar1, Ar2, Ar3, a, b, R′ and R″ are the same as defined in claim 1,
2) R6 and R7 are the same or different, 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 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; and a C6-C30 aryloxy group; or in case f′ and g′ are 2 or more, each as plurality are the same as or different from each other, and a plurality of R6 or a plurality of R7 or a plurality of R8 or adjacent R6 and R7, or adjacent R7 and R8 may be bonded to each other to form an aromatic or a heteroaromatic ring,
3) a′, c′ and d′ are each an integer of 0 to 4, and f′ and g′ are each an integer of 0 to 3,
4) Y is NR′, O, S or CR′R″, and
5) R′ and R″ are independently hydrogen; a C6-C60 aryl group; a fluorenyl group;
a C3-C60 heterocyclic group; or a C1-C50 alkyl group, wherein R′ and R″ may be bonded to each other to form a spiro ring.

### Claim 5 (depends on 1)

The organic electric element of claim 1, wherein the first host compound of Formula 1 is represented by one of Formulas 9 to 20:
wherein R1, R2, L1, Ar1, Ar2, Ar3, a and b are the same as defined in claim 1.

### Claim 6 (depends on 1)

The organic electric element of claim 1, wherein the first host compound of Formula 1 is represented by Formula 21 or Formula 22:
wherein R1, R2, L1, Ar1, Ar2, Ar3, a and b are the same as defined in claim 1.

### Claim 7 (depends on 1)

The organic electric element of claim 1, wherein n is 1 in Formula 1.

### Claim 8 (depends on 1)

The organic electric element of claim 1, wherein n is 2 in Formula 1.

### Claim 9 (depends on 1, 2)

The organic electric element of claim 1, wherein the first host compound of Formula 1 is represented by Formula 23:
wherein
1) R1, R2, L1, Ar1, Ar2, a. b and n are the same as defined in claim 1,
2) f is an integer of 0 to 3, and g is an integer of 0 to 4,
3) R9 and R10 are the same or different, 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 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; and a C6-C30 aryloxy group; or in case f and g are 2 or more, each as plurality are the same as or different from each other, and a plurality of R9 or a plurality of R10 or adjacent R9 and R10 may be bonded to each other to form an aromatic or a heteroaromatic ring,
4) Y is NR′, O, S or CR′R″, wherein R′ and R″ are independently hydrogen; a C6-C60 aryl group; a fluorenyl group; a C3-C60 heterocyclic group; or a C1-C50 alkyl group, wherein R′ and R″ may be bonded to each other to form a spiro ring.

### Claim 10 (depends on 1)

The organic electric element of claim 1, wherein A and B in Formula 24 are selected from the group consisting of Formulas (B-1) to (B-7):
wherein
1) Z4 to Z50 are independently CR′ or N,
2) R′ is hydrogen; a C6-C60 aryl group; a fluorenyl group; a C3-C60 heterocyclic group; or a C1-C50 alkyl group,
3) * indicates the position to be condensed.

### Claim 11 (depends on 1)

The organic electric element of claim 1, wherein R4 in Formula 24 comprises a compound forming an aromatic ring or a heteroaromatic ring.

### Claim 12 (depends on 1)

The organic electric element of claim 1, wherein the second host compound of Formula 24 is represented by one of Formulas 26 to 34:
wherein
Ar4, X1, R3, R4, R5, L2, c, d, and e are the same as defined in claim 1.

### Claim 13 (depends on 1)

The organic electric element of claim 1, wherein the second host compound of Formula 24 is represented by one of Formulas 46 to 49:
wherein,
R3, R4, R5, Ar4, L2, c, d, e, A, B, R′ and R″ are the same as defined in claim 1.

### Claim 14 (depends on 1)

The organic electric element of claim 1, wherein the first host compound of Formula 1 is selected from the group consisting of compounds 1-1 to 1-68 and compounds 2-1 to 2-68:

### Claim 15 (depends on 1)

The organic electric element of claim 1, wherein the second host compound of Formula 24 is selected from the group consisting of compounds 3-1 to 3-12, 3-25 to 3-36, 3-41, 3-49 to 3-60, 3-73 to 3-84, and 3-81′ to 3-84′:

### Claim 16 (depends on 1)

The organic electric element of claim 1, wherein the emitting layer is a phosphorescent light emitting layer.

### Claim 17 (depends on 1)

The organic electric element of claim 1, wherein the compounds represented by Formula 1 and by Formula 24 are mixed in a ratio of 1:9 to 9:1 to be included in the emitting layer.

### Claim 18 (depends on 1)

The organic electric element of claim 1, wherein the compound represented by Formula 1 and by Formula 24 are mixed in a ratio of 1:9 to 5:5 to be included in the emitting layer.

### Claim 19 (depends on 1)

The organic electric element of claim 1, wherein the compounds represented by Formula 1 and by Formula 24 are mixed in a ratio of 2:8 or 3:7 to be included in the emitting layer.