# US 2026/0096342 A1 · Heterocyclic compound, composition for organic layer including the same and light emitting device including the same

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- Number: US 2026/0096342 A1
- Document ID: US20260096342A1
- Status: Published application
- Kind: A1
- Application number: 19/339,720
- Filed: 2025-09-25
- Published: 2026-04-02
- Earliest claimed: 2024-09-27
- Assignees: Lt Materials Co., Ltd.
- Applicants: Lt Materials Co., Ltd.
- Inventors: SEUNG WOO LEE; JUN TAE MO; DONG JUN KIM; DAE HYUK CHOI
- Web page: https://patentgrep.com/patent/US20260096342A1

## CPC

- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- C07B 59/002: {Heterocyclic compounds}
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/14: containing three or more hetero rings
- C07D 409/14: containing three or more hetero rings
- C09K 11/02: Use of particular materials as binders, particle coatings or suspension media therefor
- C09K 11/06: containing organic luminescent materials
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/342: {comprising iridium}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 50/12: comprising dopants
- 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 2101/10: Triplet emission
- H10K 2101/90: {Multiple hosts in the emissive layer}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A heterocyclic compound is represented by Formula 1. A light-emitting device includes a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode and including the heterocyclic compound. The organic layer may include an emission layer including a dopant material and a host material including the heterocyclic compound.

## Claims

### Claim 1

A heterocyclic compound represented by Formula 1:
wherein two adjacent groups of R1 to R4 are linked to form an aromatic ring represented by
and
among the remaining two groups of R1 to R4 that do not form the aromatic ring and R5 to R12:
one is a group represented by Formula 2;
another is a benzocarbazole group having a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms bonded to a nitrogen atom; and
the remaining ones are each independently selected from the groups consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, —SiRR′R″, or —P(═O)RR′, wherein two or more adjacent groups among the remaining ones are optionally linked to form a substituted or unsubstituted 5- to 9-membered saturated or unsaturated ring; and
R, R′ and R″ are each independently hydrogen, deuterium, —CN, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms:
in Formula 2, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,
L1, L2, and L3 are each independently a direct linkage, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,
a, b and c are each independently an integer of 0 to 5,
when a is an integer of 2 to 5, a plurality of L1 groups are the same or different,
when b is an integer of 2 to 5, a plurality of L2 groups are the same or different,
when c is an integer of 2 to 5, a plurality of L3 groups are the same or different, and
* represents a bonding site.

### Claim 2 (depends on 1)

The heterocyclic compound according to claim 1, wherein the heterocyclic compound is represented by any one selected from the groups consisting of Formulae 1-1 to 1-3:
in Formulae 1-1 to 1-3, R1 to R12 are the same as defined in Formula 1.

### Claim 3 (depends on 2)

The heterocyclic compound according to claim 2, wherein, in Formulae 1-1 to 1-3,
among the remaining two groups of R1 to R4 that do not form the ring and R5 to R8,
one is represented by Formula 2, another is a benzocarbazole group having a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms bonded to a nitrogen atom, and
R9 to R12 are each independently hydrogen or deuterium.

### Claim 4 (depends on 1)

The heterocyclic compound according to claim 1, wherein the benzocarbazole group is represented by any one selected from the groups consisting of Formulae 3-1 to 3-4:
in Formulae 3-1 to 3-4, Ar3 is an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms,
two adjacent groups of Rd, Re, Rf and Rg are linked to form an aromatic ring represented by
the remaining two groups of Rd, Re, Rf and Rg that do not form the ring, and Rh, Ri, Rj, Rk, Rl, Rm and Rn are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, —SiRR′R″, and —P(═O)RR′, wherein two or more adjacent groups among the remaining two groups of Rd, Re, Rf and Rg that do not form the ring and Rh, Ri, Rj, Rk, Rl, Rm and Rn are optionally linked to form a substituted or unsubstituted 5- to 9-membered saturated or unsaturated ring, and
R, R′ and R″ are each independently hydrogen, deuterium, —CN, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,
q is an integer of 0 to 3, and when q is 2 or 3, a plurality of Rh groups are the same or different,
r is an integer of 0 to 5, and when r is an integer from 2 to 5, a plurality of Ri groups are the same or different, and
s is an integer of 0 to 4, and when s is an integer from 2 to 4, a plurality of Rj groups are the same or different.

### Claim 5 (depends on 4)

The heterocyclic compound according to claim 4, wherein, in Formulae 3-1 to 3-4, Ar3 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

### Claim 6 (depends on 1)

The heterocyclic compound according to claim 1, wherein, in Formula 2, L1 is a direct linkage or a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.

### Claim 7 (depends on 1)

The heterocyclic compound according to claim 1, wherein the deuterium content of the heterocyclic compound is 0, or greater than 0 and not more than 100%.

### Claim 8 (depends on 1)

The heterocyclic compound according to claim 1, wherein the heterocyclic compound is represented by any one of Formulae below:

### Claim 9 (depends on 1)

A light-emitting device comprising:
a first electrode;
a second electrode; and
one or more organic layers interposed between the first electrode and the second electrode,
wherein one or more of the organic layers comprises the heterocyclic compound according to claim 1.

### Claim 10 (depends on 9)

The light-emitting device according to claim 9, wherein the organic layer comprises an emission layer, and
the emission layer comprises a dopant material and a host material, and the host material comprises the heterocyclic compound.

### Claim 11 (depends on 10)

The light-emitting device according to claim 10, wherein the organic layer further comprises a hole transport layer disposed between the first electrode and the emission layer, and an electron transport layer disposed between the emission layer and the second electrode.

### Claim 12 (depends on 10)

The light-emitting device according to claim 10, wherein the host material further comprises a compound represented by Formula 4:
in Formula 4, any one of R21 to R27 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,
the remaining groups of R21 to R27 are each independently selected from the group consisting of hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a phosphine oxide group, and a silyl group, or two or more adjacent groups are linked to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms,
L4 is a direct linkage, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
z is an integer of 0 to 5;
when z is an integer of 2 to 5, a plurality of L4 groups are the same or different;
Y1 to Y3 are each independently CH, nitrogen (N), oxygen (O), or sulfur(S); and at least two of Y1 to Y3 are nitrogen; and
Ar21 and Ar22 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

### Claim 13 (depends on 12)

The light-emitting device according to claim 12, wherein the compound represented by Formula 4 comprises one or more compounds represented by any one of Formulae below:

### Claim 14 (depends on 1)

A composition for an organic layer of an organic light-emitting device, comprising:
the heterocyclic compound represented by Formula 1 according to claim 1; and
a compound represented by Formula 4 below:
in Formula 4, any one of R21 to R27 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,
the remaining groups of R21 to R27 are each independently selected from the group consisting of hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a phosphine oxide group, and a silyl group, or two or more adjacent groups are linked to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms,
L4 is a direct linkage, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
z is an integer of 0 to 5;
when z is an integer of 2 to 5, a plurality of L4 groups are the same or different;
Y1 to Y3 are each independently CH, nitrogen (N), oxygen (O), or sulfur(S), and at least two of Y1 to Y3 are nitrogen; and
Ar21 and Ar22 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

### Claim 15 (depends on 14)

A composition for an organic layer of an organic light-emitting device according to claim 14, wherein the weight ratio of the compound represented by Formula 4 to the weight of the heterocyclic compound represented by Formula 1 in the total weight of the composition is 0.1 to 10.