# US 2024/0206334 A1 · Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

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- Number: US 2024/0206334 A1
- Document ID: US20240206334A1
- Status: Published application
- Kind: A1
- Application number: 18/413,635
- Filed: 2024-01-16
- Published: 2024-06-20
- Earliest claimed: 2020-10-26
- Assignees: Duk San Neolux Co., Ltd.
- Applicants: Duk San Neolux Co., Ltd.
- Inventors: Hyun Ju SONG; Hyo Min JIN; Junggeun LEE
- Web page: https://patentgrep.com/patent/US20240206334A1

## CPC

- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- C07D 251/24: to three ring carbon atoms
- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07D 333/76: Dibenzothiophenes
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C09K 11/06: containing organic luminescent materials
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-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 85/653: {comprising only oxygen as heteroatom}
- 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 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 50/18: Carrier blocking layers
- H10K 2101/10: Triplet emission
- H10K 2101/90: {Multiple hosts in the emissive layer}
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Provided are a compound that improves the luminous efficiency, stability, and lifespan of an organic electronic element using the same, the element, and an electronic device thereof.

## Claims

### Claim 1

A compound represented by Formula (1):
wherein:
R1, R2 and R3 are each the same or different, and each independently hydrogen or deuterium,
a is an integer of 0 to 5, b is an integer of 0 to 6, c is an integer of 0 to 4,
L1 and L2 are each independently selected from the group consisting of single bond; a C6-C60 arylene group; and a C2-C60 heterocyclic group including at least one heteroatom of O, N, S, Si or P;
Ar1 and Ar2 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 a C3-C60 aliphatic ring; and a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring;
wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group and fused ring group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; 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, and the hydrogen of these substituents may be further substituted with one or more deuterium, and the substituents may be bonded to each other to 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 group or a fused ring formed by the combination thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein L1 and L2 are a single bond or represented by any of Formulas L-1 to L-20:
wherein:
Z is O, S, C(R23)(R24) or N—Ar3,
R4, R5, R6, R7, R8, R9, R23, R24 and Ar3 are each the same or different, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a nitro group; a C6-C20 aryl group; a C6-C20 aryl group substituted with deuterium; a fluorenyl group; a C2-C20 heterocyclic group including at least one hetero atom of O, N, S, Si or a C3-C20 cycloalkyl group; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C20 alkoxyl group; or an adjacent plurality of R4 or plurality of R5 or plurality of R6 or plurality of R7 or plurality of R8 or plurality of R9 may be bonded to each other to form a ring,
d, f, g, h and i are each independently an integer of 0 to 4, e is an integer of 0 to 6, and
* means the position to be bonded.

### Claim 3 (depends on 1)

The compound of claim 1, wherein Ar1 and Ar2 are represented by any one of Formulas Ar-1 to Ar-12:
wherein:
X is O, S, CRaRb or NRc,
Ra, Rb, Rc, R10, R11, R12, R13, R14, R15 and R16 are each selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a nitro group; a C6-C20 aryl group; a C6-C20 aryl group substituted with deuterium; a fluorenyl group; a C2-C20 heterocyclic group including at least one hetero atom of O, N, S, Si or P; a C3-C20 cycloalkyl group; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; and a C1-C20 alkoxyl group, and adjacent groups thereof may be bonded to each other to form a ring,
j is an integer of o to 5, k is an integer of 0 to 7, l is an integer of 0 to 9, m, n and p are each independently an integer of 0 to 4, o is an integer of 0 to 2, and
* means the position to be bonded.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the compound represented by Formula (1) is any one of Compounds P-1 to P-96:

### Claim 5 (depends on 1)

A composition for an organic electronic element comprising a mixture of a compound represented by Formula (1) of claim 1, and a compound represented by Formula 4 or Formula 5:
wherein:
L12, L13, L14 and L15 are each independently selected from the group consisting of single bond; a C6-C60 arylene group; a fluorenylene group; a C2-C60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; and a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring;
Ar12, Ar13 and Ar14 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; and a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring; a C3-C60 aliphatic 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;
Ar15 is 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; and a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring; and —L′—NR′R″;
Y10 is O, S, CR51R52 or NR53,
Ring B is an C6˜C20 aryl group,
L′ is selected from the group consisting of a single bond; a C6-C60 arylene group; a fluorenylene group; a C2-C60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; and a C3-C60 aliphatic ring,
R51, R52, R53, R′ and R″ are the same as the definition of Ar12, or R51 and R52 are bonded to each other to form a spiro,
R31 and R32 are each the same or different, and each independently selected from the group consisting of hydrogen; deuterium; a halogen; a cyano group; 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 F; 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, and an adjacent plurality of R31 or plurality of R32 may be bonded to each other to form a ring,
ba and bb are each independently an integer of 0 to 4,
wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; 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; and —L′—NR′R″, and the hydrogen of these substituents may be further substituted with one or more deuterium, and the substituents may be bonded to each other to 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 group or a fused ring formed by the combination thereof.

### Claim 6 (depends on 5)

The composition for an organic electronic element according to claim 5, wherein the composition for an organic electronic element is for a host for an emitting layer.

### Claim 7 (depends on 5)

The composition for an organic electronic element according to claim 5, wherein the compound of Formula 4 is any one of Compounds H-1 to H-124:

### Claim 8 (depends on 5)

The composition for an organic electronic element according to claim 5, wherein the compound of Formula 5 is any one of Compounds S-1 to S-116:

### Claim 9 (depends on 1, 5)

An organic electronic 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 the compound represented by Formula (1) of claim 1 or the composition for an organic electronic element of claim 5.

### Claim 10 (depends on 9)

The organic electronic element according to claim 9, further comprising a light efficiency enhancing layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic material layer.

### Claim 11 (depends on 9)

The organic electronic element according to claim 9, wherein the organic material layer comprises 2 or more stacks comprising a hole transport layer, an emitting layer and an electron transport layer sequentially formed on the first electrode.

### Claim 12 (depends on 11)

The organic electronic element according to claim 11, the organic material layer further comprise a charge generation layer formed between the 2 or more stacks.

### Claim 13 (depends on 9)

An electronic device comprising a display device comprising the organic electronic element of claim 9; and a control unit for driving the display device.

### Claim 14 (depends on 13)

The electronic device according to claim 13, wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photo conductor(OPC), organic transistor (organic TFT) and an element for monochromic or white illumination.

### Claim 15 (depends on 1)

A method for reusing a compound of Formula (1) of claim 1 comprising:
recovering a crude organic light emitting material comprising the compound of Formula (1) from a deposition apparatus used in a process for depositing the organic emitting material to prepare an organic light emitting device;
removing impurities from the crude organic light emitting material;
recovering the organic light emitting material after the impurities are removed; and
purifying the recovered organic light emitting material to have a purity of 99.9% or higher.