# US 2025/0098531 A1 · Organic compounds and organic light-emitting device comprising the same

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- Number: US 2025/0098531 A1
- Document ID: US20250098531A1
- Status: Published application
- Kind: A1
- Application number: 18/884,440
- Filed: 2024-09-13
- Published: 2025-03-20
- Earliest claimed: 2023-09-14
- Assignees: Sfc Co., Ltd.
- Applicants: Sfc Co., Ltd.
- Inventors: So-young SHIM; Jin-hwi CHO
- Web page: https://patentgrep.com/patent/US20250098531A1

## CPC

- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- C09K 11/02: Use of particular materials as binders, particle coatings or suspension media therefor
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/12: comprising dopants
- H10K 85/30: Coordination compounds
- H10K 85/342: {comprising iridium}
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- 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}
- H10K 2101/90: {Multiple hosts in the emissive layer}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The present invention relates to an organic compound represented by the following [Formula 1], and a high-efficiency and long-lifetime organic light emitting device enabling significantly improved low voltage driving, and having excellent luminous efficiency, long lifetime and the like by employing the same as a light emitting layer host material in the device.

## Claims

### Claim 1

An organic light emitting device comprising:
a first electrode;
a second electrode opposite to the first electrode; and
an organic layer interposed between the first electrode and the second electrode,
wherein the organic layer includes a light emitting layer including a host and a dopant; and
the host includes at least one type of organic compound represented by the following [Formula 1]:
in [Formula 1],
X1 to X3 are the same as or different from each other and each independently N or CR, and at least one of X1 to X3 is N;
L1 to L3 are the same as or different from each other, and each independently a single bond, or any one selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, and substituted or unsubstituted divalent cyclic groups in which a C3-C24 aliphatic ring and a C5-C24 aromatic ring are fused together;
R and R1 to R3 are the same as or different from each other, and each independently any one selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 haloalkyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C50 cycloalkyl, substituted or unsubstituted C2-C50 heterocycloalkyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted cyclic groups in which a C3-C30 aliphatic ring and a C5-C30 aromatic ring are fused together, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthioxy, substituted or unsubstituted C5-C30 arylthioxy, substituted or unsubstituted amine, substituted or unsubstituted silyl, substituted or unsubstituted germanium, nitro, cyano and halogen;
however, at least one of R1s of [Formula 1] is [Structural Formula 1],
in [Structural Formula 1],
‘*’ means a bonding site linked to L1 of [Formula 1];
X4 to X7 are the same as or different from each other and each independently N or CR7, and at least one of X1 to X4 is N;
L4s are the same as or different from each other, and each independently a single bond, or any one selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, and substituted or unsubstituted divalent cyclic groups in which a C3-C24 aliphatic ring and a C5-C24 aromatic ring are fused together;
R7s are the same as or different from each other, and each independently any one selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 haloalkyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C50 cycloalkyl, substituted or unsubstituted C2-C50 heterocycloalkyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted cyclic groups in which a C3-C30 aliphatic ring and a C5-C30 aromatic ring are fused together, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthioxy, substituted or unsubstituted C5-C30 arylthioxy, substituted or unsubstituted amine, substituted or unsubstituted silyl, substituted or unsubstituted germanium, nitro, cyano and halogen;
R4 to R6 are the same as or different from each other, and each independently any one selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 haloalkyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C50 cycloalkyl, substituted or unsubstituted C2-C50 heterocycloalkyl, substituted or unsubstituted C2-C50 heteroaryl, and substituted or unsubstituted cyclic groups in which a C3-C30 aliphatic ring and a C5-C30 aromatic ring are fused together;
n1 to n3 are each independently an integer of 1 to 3, and when they are integers of 2 or greater, R1s to R3s are the same as or different from each other;
n4 is an integer of 4, and R4s are the same as or different from each other;
m1 to m4 are each independently an integer of 1 to 3, and when they are integers of 2 or greater, Lis to L4s are the same as or different from each other;
the plurality of adjacent R7s are optionally linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring; and
the term ‘substituted’ in the ‘substituted or unsubstituted’ in [Formula 1] and [Structural Formula 1] means being substituted with one or more substituents selected from the group consisting of deuterium, tritium, C1-C24 alkyl, C1-C24 haloalkyl, C2-C24 alkenyl, C2-C24 alkynyl, C3-C30 cycloalkyl, C1-C24 heteroalkyl, C6-C30 aryl, C7-C30 arylalkyl, C7-C30 alkylaryl, C2-C30 heteroaryl, C2-C30 heteroarylalkyl, cyclic groups in which a C3-C24 aliphatic ring and a C5-C24 aromatic ring are fused together, C1-C24 alkoxy, C1-C30 amine, C1-C30 silyl, C1-C30 germanium, C6-C24 aryloxy, C6-C24 arylthionyl, cyano, halogen, hydroxyl and nitro, and when there are two or more substituents, they are the same as or different from each other, and one or more hydrogen atoms in each of the substituents are optionally substituted with deuterium or tritium atoms.

### Claim 2 (depends on 1)

The organic light emitting device according to claim 1, wherein at least one of R2 and R3 in [Formula 1] is substituted or unsubstituted C6-C30 aryl.

### Claim 3 (depends on 2)

The organic light emitting device according to claim 2, wherein the substituted of the substituted or unsubstituted C6-C30 aryl is with any one selected from C1-C30 silyl or C1-C30 germanium.

### Claim 4 (depends on 1)

The organic light emitting device according to claim 1, wherein X1 to X3 in [Formula 1] are all N.

### Claim 5 (depends on 1)

The organic light emitting device according to claim 1, wherein at least one of R2 and R3 in [Formula 1] is substituted or unsubstituted C3-C20 heteroaryl.

### Claim 6 (depends on 5)

The organic light emitting device according to claim 5, wherein the heteroaryl is substituted or unsubstituted carbazole.

### Claim 7 (depends on 1)

The organic light emitting device according to claim 1, wherein R4 to R6 in [Structural Formula 1] are the same as or different from each other, and each independently any one selected from hydrogen, deuterium and substituted or unsubstituted C1-C10 alkyl.

### Claim 8 (depends on 1)

The organic light emitting device according to claim 1, wherein m4 in [Structural Formula 1] is an integer of 1, and at the same time, L4 is a single bond.

### Claim 9 (depends on 1)

The organic light emitting device according to claim 1, wherein at least one deuterium atom substitutes in [Formula 1].

### Claim 10 (depends on 1)

The organic light emitting device according to claim 1, wherein [Formula 1] is any one selected from compounds represented by the following formulae:

### Claim 11 (depends on 1)

The organic light emitting device according to claim 1, wherein, in addition to the organic compound represented by [Formula 1], one or more types of host compounds different therefrom are mixed or stacked and used as the host in the light emitting layer of the organic light emitting device.

### Claim 12 (depends on 1)

The organic light emitting device according to claim 1, wherein the dopant in the light emitting layer of the organic light emitting device includes at least one organometallic compound including a transition metal.

### Claim 13 (depends on 12)

The organic light emitting device according to claim 12, wherein, as the dopant in the light emitting layer of the organic light emitting device, one or more types of polycyclic compounds represented by the following [Formula 2] are mixed and used in addition to the organometallic compound including a transition metal, or a polycyclic compound represented by the following [Formula 2] is stacked and used above or below the layer including the organometallic compound:
in [Formula 2],
Y1 and Y2 are the same as or different from each other, and each independently any one selected from O, S, NR11, CR12R13, SiR14R15 and GeR16R17;
A1 to A3 are the same as or different from each other, and each independently any one selected from substituted or unsubstituted C6-C30 aromatic hydrocarbon rings, substituted or unsubstituted C3-C30 aliphatic hydrocarbon rings, substituted or unsubstituted C2-C30 aromatic heterocyclic rings, substituted or unsubstituted C2-C30 aliphatic heterocyclic rings, and substituted or unsubstituted cyclic groups in which a C3-C24 aliphatic ring and a C5-C24 aromatic ring are fused together;
R11 to R17 are the same as or different from each other, and each independently any one selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 haloalkyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C50 cycloalkyl, substituted or unsubstituted C2-C50 heterocycloalkyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted cyclic groups in which a C3-C30 aliphatic ring and a C5-C30 aromatic ring are fused together, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthioxy, substituted or unsubstituted C5-C30 arylthioxy, substituted or unsubstituted amine, substituted or unsubstituted silyl, substituted or unsubstituted germanium, nitro, cyano and halogen;
R11 to R17 are optionally linked to the rings A1 to A3 to further form an alicyclic or aromatic monocyclic or polycyclic ring;
R12 and R13, R14 and R15, and R16 and R17 are optionally linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring; and
the term ‘substituted’ in the ‘substituted or unsubstituted’ in [Formula 2] means being substituted with one or more substituents selected from the group consisting of deuterium, tritium, C1-C24 alkyl, C1-C24 haloalkyl, C2-C24 alkenyl, C2-C24 alkynyl, C3-C30 cycloalkyl, C1-C24 heteroalkyl, C6-C30 aryl, C7-C30 arylalkyl, C7-C30 alkylaryl, C2-C30 heteroaryl, C2-C30 heteroarylalkyl, cyclic groups in which a C3-C24 aliphatic ring and a C5-C24 aromatic ring are fused together, C1-C24 alkoxy, C1-C30 amine, C1-C30 silyl, C1-C30 germanium, C6-C24 aryloxy, C6-C24 arylthionyl, cyano, halogen, hydroxyl and nitro, and when there are two or more substituents, they are the same as or different from each other, and one or more hydrogen atoms in each of the substituents are optionally substituted with deuterium or tritium atoms.

### Claim 14 (depends on 1)

The organic light emitting device according to claim 1, wherein the organic light emitting device is used in any one device selected from flat panel displays, flexible displays, monochromatic or white flat panel lighting systems, monochromatic or white flexible lighting systems, displays for automotives and aircraft, and displays for virtual or augmented reality.

### Claim 15

An organic compound represented by the following [Formula 1]:
wherein, in [Formula 1],
X1 to X3 are the same as or different from each other and each independently N or CR, and at least one of X1 to X3 is N;
L1 to L3 are the same as or different from each other, and each independently a single bond, or any one selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, and substituted or unsubstituted divalent cyclic groups in which a C3-C24 aliphatic ring and a C5-C24 aromatic ring are fused together;
R and R1 to R3 are the same as or different from each other, and each independently any one selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 haloalkyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C50 cycloalkyl, substituted or unsubstituted C2-C50 heterocycloalkyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted cyclic groups in which a C3-C30 aliphatic ring and a C5-C30 aromatic ring are fused together, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthioxy, substituted or unsubstituted C5-C30 arylthioxy, substituted or unsubstituted amine, substituted or unsubstituted silyl, substituted or unsubstituted germanium, nitro, cyano and halogen;
however, at least one of R1s of [Formula 1] is [Structural Formula 1],
in [Structural Formula 1],
‘*’ means a bonding site linked to L1 of [Formula 1];
X4 to X7 are the same as or different from each other and each independently N or CR7, and at least one of X1 to X4 is N;
L4s are the same as or different from each other, and each independently a single bond, or any one selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, and substituted or unsubstituted divalent cyclic groups in which a C3-C24 aliphatic ring and a C5-C24 aromatic ring are fused together;
R7s are the same as or different from each other, and each independently any one selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 haloalkyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C50 cycloalkyl, substituted or unsubstituted C2-C50 heterocycloalkyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted cyclic groups in which a C3-C30 aliphatic ring and a C5-C30 aromatic ring are fused together, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthioxy, substituted or unsubstituted C5-C30 arylthioxy, substituted or unsubstituted amine, substituted or unsubstituted silyl, substituted or unsubstituted germanium, nitro, cyano and halogen;
R4 to R6 are the same as or different from each other, and each independently any one selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 haloalkyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C50 cycloalkyl, substituted or unsubstituted C2-C50 heterocycloalkyl, substituted or unsubstituted C2-C50 heteroaryl, and substituted or unsubstituted cyclic groups in which a C3-C30 aliphatic ring and a C5-C30 aromatic ring are fused together;
n1 to n3 are each independently an integer of 1 to 3, and when they are integers of 2 or greater, R1s to R3s are the same as or different from each other;
n4 is an integer of 4, and R4s are the same as or different from each other;
m1 to m4 are each independently an integer of 1 to 3, and when they are integers of 2 or greater, Lis to L4s are the same as or different from each other;
the plurality of adjacent R7s are optionally linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring; and
the term ‘substituted’ in the ‘substituted or unsubstituted’ in [Formula 1] and [Structural Formula 1] means being substituted with one or more substituents selected from the group consisting of deuterium, tritium, C1-C24 alkyl, C1-C24 haloalkyl, C2-C24 alkenyl, C2-C24 alkynyl, C3-C30 cycloalkyl, C1-C24 heteroalkyl, C6-C30 aryl, C7-C30 arylalkyl, C7-C30 alkylaryl, C2-C30 heteroaryl, C2-C30 heteroarylalkyl, cyclic groups in which a C3-C24 aliphatic ring and a C5-C24 aromatic ring are fused together, C1-C24 alkoxy, C1-C30 amine, C1-C30 silyl, C1-C30 germanium, C6-C24 aryloxy, C6-C24 arylthionyl, cyano, halogen, hydroxyl and nitro, and when there are two or more substituents, they are the same as or different from each other, and one or more hydrogen atoms in each of the substituents are optionally substituted with deuterium or tritium atoms.