# US 2018/0123051 A1 · Compound for organic electric element, organic electric element using the same, and electronic device thereof

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- Number: US 2018/0123051 A1
- Document ID: US20180123051A1
- Status: Published application
- Kind: A1
- Application number: 15/566,628
- Filed: 2017-03-16
- Published: 2018-05-03
- 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/US20180123051A1

## 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 at position 1

-23. (canceled)

### Claim 24

A compound represented by Formula 2 below
in Formula 2,
1) Ar4 is 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; a C6-C30 aryloxy group; and -L′-N(Ra)(Rb) (where, 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 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 containing at least one hetero atom of O, N, S, Si, and P),
2) c and e are integer of 0 to 10, and d is an integer of 0 to 2,
3) R3, R4 and R5 may be 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; a C6-C30 aryloxy group; and -L′-N(Ra)(Rb) wherein L′, Ra and Rb are same as defined above; or in case c and e are 2 or more and d is 2, 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) L2 may be 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 may be independently a C6-C60 aryl group or a C2-C20 heterocyclic group, wherein 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 a ring to form an aromatic or hetero ring,
6) i and j are independently 0 or 1, with the proviso that i+j is 1 or more, and when i or j is 0, it means a direct bond,
7) X1 and X2 are independently 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; or R′ and R″ may be bonded to each other to form a spiro,
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 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 25

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, wherein the emitting layer comprises a first host compound represented by Formula 1 as the phosphorescent light emitting layer and a second host compound represented by Formula 2.
In Formula 1 and Formula 2,
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; 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, 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 P, N, S, Si, and P, wherein Ar2 and Ar3 may be bonded to each other to form a ring,
2) a is an integer of 0 to 4, and b is an integer of 0 to 3, and c and e are integer of 0 to 10, and d is an integer of 0 to 2,
3) R1, R2, R3, R4 and R5 may be 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; a C6-C30 aryloxy group; and -L′-N(Ra)(Rb); 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 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 hetero ring,
6) i and j are independently 0 or 1, with the proviso that i+j is 1 or more, and when i or j is 0, it means a direct bond,
7) X1 and X2 are independently 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,
8) 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; 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 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 26 (depends on 25)

The compound of claim 25, wherein the first host compound represented by Formula 1 comprises a compound represented by Formula 3 or Formula 4 below.
wherein R1, R2, L1, Ar1, Ar2, Ar3, a and b are the same as defined in claim 25.

### Claim 26 (depends on 25)

The compound of claim 25, wherein R4 in Formula 2 comprises a compound forming an aromatic ring or a heteroaromatic ring.

### Claim 27 (depends on 25)

The compound of claim 25, wherein L1 and L2 are selected from the group consisting of the following Formulas (A-1) to (A-12):
In Formulas (A-1) to (A-12),
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 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 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) R′ and R″ are the same as defined above,
5) Z1, Z2 and Z3 are independently of each other CR′ or N and at least one is N.

### Claim 27 (depends on 25)

The compound of claim 25, wherein the second host compound represented by Formula 2 comprises a compound represented by any one of the following Formulas 26 to 45:
In Formulas 26 to 45,
Ar4, X1, X2, R3, R4, R5, L2, c, d, and e are the same as defined in the claim 25.

### Claim 28 (depends on 2, 25)

The compound of claim 25, wherein the first host compound represented by Formula 1 is represented by any one of the following Formulas 5 to 8:
wherein
1) R1, R2, Ar1, Ar2, Ar3, a, b, R′ and R″ are the same as defined in claim 25,
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; a C6-C30 aryloxy group; and -L′-N(Ra)(Rb); 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″.

### Claim 28 (depends on 25)

The compound of claim 25, wherein the second host compound represented by Formula 2 comprises any one of compounds represented by Formulas 46 to 53 below:
In Formulas 46 to 53,
R3, R4, R5, Ar4, L2, c, d, e, A, B, R′ and R″ are the same as defined in the claim 25.

### Claim 29 (depends on 25)

The compound of claim 25, wherein the first host compound represented by Formula 1 is represented by any one of Formulas 9 to 20 below:
wherein R1, R2, L1, Ar1, Ar2, Ar3, a and b are the same as defined in the claim 25.

### Claim 29 (depends on 25)

The compound of claim 25, wherein the first host compound represented by Formula 1 is any one of the following Compounds 1-1 to 1-68 and Compounds 2-1 to 2-68:

### Claim 30 (depends on 25)

The compound of claim 25, wherein the first host compound represented by Formula 1 comprises a compound represented by any one of Formula 21 to Formula 22 below:
wherein R1, R2, L1, Ar1, Ar2, Ar3, a and b are the same as defined in the claim 25.

### Claim 30 (depends on 25)

The compound of claim 25, wherein the second host compound represented by Formula 2 comprises any one of the following Compounds 3-1 to 3-86:

### Claim 31 (depends on 25)

The compound of claim 25, wherein n is 1 in Formula 1.

### Claim 31 (depends on 25)

The compound of claim 25, wherein the emitting layer is a phosphorescent light emitting layer.

### Claim 32 (depends on 25)

The compound of claim 25, wherein n is 2 in Formula 2.

### Claim 32 (depends on 25)

The compound of claim 25, wherein the compounds represented by Formula 1 and by Formula 2 are mixed in a ratio of 1:9 to 9:1 to be included in the emitting layer.

### Claim 33 (depends on 2, 25)

The compound of claim 25, wherein the first host compound represented by Formula 1 comprises a compound represented by Formula 23 below:
wherein
1) R1, R2, L1, Ar1, Ar2, a, b and n are the same as defined in claim 25,
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; a C6-C30 aryloxy group; and -L′-N(Ra)(Rb); 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″,
5) R′ and R″ are the same as defined above.

### Claim 33 (depends on 25)

The compound of claim 25, wherein the compound represented by Formula 1 and by Formula 2 are mixed in a ratio of 1:9 to 5:5 to be included in the emitting layer.

### Claim 34 (depends on 25)

The compound of claim 25, wherein the second host compound represented by the Formula 2 comprises a compound represented by Formula 24 or Formula 25 below:
wherein R3, R4, R5, Ar4, L2, c, d, e, A, B, X1 and X2 are the same as defined in the claim 25.

### Claim 34 (depends on 25)

The compound of claim 25, wherein he compound represented by Formula 1 and by Formula 2 are mixed in a ratio of 2:8 or 3:7 to be included in the emitting layer.

### Claim 35 (depends on 25)

The compound of claim 25, wherein A and B in the Formula 2 are selected from the group consisting of the following Formulas (B-1) to (B-7):
In Formulas (B-1) to (B-7),
1) Z4 to Z50 are CR′ or N,
2) R′ is the same as defined above,
3) * indicates the position to be condensed.

### Claim 35 (depends on 25)

An electronic device comprising a display device including the organic electric element of claim 25; and a control unit for driving the display device.

### Claim 36 (depends on 35)

The electronic device of claim 35, wherein the organic electric element is at least one of an OLED, an organic solar cell, an organic photo conductor, an organic transistor and an element for monochromic or white illumination.