# US 12,120,953 B2 · Heterocyclic compound, organic light-emitting device including heterocyclic compound, and electronic apparatus including organic light-emitting device

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 12,120,953 B2
- Document ID: US12120953B2
- Status: Granted
- Kind: B2
- Application number: 17/197,235
- Filed: 2021-03-10
- Published: 2022-04-14
- Granted: 2024-10-15
- Earliest claimed: 2020-09-10
- Assignees: Samsung Electronics Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.
- Inventors: Soonok Jeon; Dmitry Androsov; Juhyun Kim; Jong Soo Kim; Sooghang Ihn
- Web page: https://patentgrep.com/patent/US12120953B2

## CPC

- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- 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 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/12: comprising dopants
- H10K 2101/10: Triplet emission
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

Provided are a heterocyclic compound represented by Formula 1, an organic light-emitting device including the heterocyclic compound, and an electronic apparatus including the organic light-emitting device: wherein Formula 1 may be understood by referring to the description of Formula 1 provided herein.

## Claims

### Claim 1

A heterocyclic compound represented by Formula 1:
wherein, in Formula 1,
ring CY1, ring CY2, ring CY4, and ring CY5 are each independently a π electron-rich C3-C60 cyclic group, wherein ring CY1, ring CY2, ring CY4, and ring CY5 are each independently a benzene group, a naphthalene group, a phenanthrene group, a furan group, a thiophene group, a pyrrole group, a cyclopentene group, a silole group, a germole group, a benzofuran group, a benzothiophene group, an indole group, an indene group, a benzosilole group, a benzogermole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, an indolodibenzofuran group, an indolodibenzothiophene group, an undolocarbazole group, an indolofluorene group, an indolodibenzosilole group, an indolodibenzogermole group, or a 9,10-dihydroacridine group,
X1 is O, S, Si(R5)(R6), Ge(R5)(R6), or P(═O)(R5),
X3 is a single bond, O, S, N(R31), C(R31)(R32), Si(R31)(R32), or Ge(R31)(R32),
R1, R2, R4 to R6, R10, and R20 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
R31, R32, R40, and R50 are each independently:
hydrogen, deuterium, —F, or a cyano group; or
a C1-C60 alkyl group, a C1-C60 alkoxy group, a π electron-rich C3-C60 cyclic group, or a pyridinyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a π electron-rich C3-C60 cyclic group, a pyridinyl group, a biphenyl group, a terphenyl group, or any combination thereof, wherein the π electron-rich C3-C60 cyclic group is a cyclic group having 3 to 60 carbon atoms and not including at least one *—N═*′ as a ring-forming moiety, wherein * and *′ each indicated a binding site to an adjacent atom,
a1, a2, a4, and a5 are each independently an integer from 0 to 20, and
a substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with deuterium, —F, —C1, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-Coo aryl group, a C6-Coo aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or any combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-Coo arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —C1, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-Coo arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or any combination thereof;
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
any combination thereof,
wherein Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C1-C60 alkyl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C10 cycloalkyl group; a C1-C10 heterocycloalkyl group; a C3-C10 cycloalkenyl group; a C1-C10 heterocycloalkenyl group; a C6-C60 aryl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C1-C60 heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.

### Claim 2 (depends on 1)

The heterocyclic compound of claim 1, wherein X1 is O or S.

### Claim 3 (depends on 1)

The heterocyclic compound of claim 1, wherein X3 is a single bond.

### Claim 4 (depends on 1)

The heterocyclic compound of claim 1, wherein R1, R2, R4 to R6, R10, and R20 are each independently:
hydrogen, deuterium, —F, or a cyano group; or
a C1-C60 alkyl group, a C1-C60 alkoxy group, a π electron-rich C3-C60 cyclic group, or a pyridinyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a π electron-rich C3-C60 cyclic group, a pyridinyl group, a biphenyl group, a terphenyl group, or any combination thereof,
wherein the π electron-rich C3-C60 cyclic group is a cyclic group having 3 to 60 carbon atoms and not including at least one *—N═*′ as a ring-forming moiety, wherein * and *′ each indicate a binding site to an adjacent atom.

### Claim 5 (depends on 1)

The heterocyclic compound of claim 1, wherein R1, R2, R4 to R6, R10, R20, R31, R32, R40, and R50 are each independently:
hydrogen, deuterium, —F, or a cyano group; or
a C1-C20 alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, a furanyl group, a thiophenyl group, a pyrrolyl group, a cyclopentenyl group, a silolyl group, a germolyl group, a benzofuranyl group, a benzothiophenyl group, an indolyl group, an indenyl group, a benzosilolyl group, a benzogermolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a dibenzosilolyl group, a dibenzogermolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzocarbazolyl group, a benzofluorenyl group, a benzonaphthosilolyl group, a benzonaphthogermolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dibenzocarbazolyl group, a dibenzofluorenyl group, a dinaphthosilolyl group, a dinaphthogermolyl group, a pyridinyl group, a biphenyl group, or a terphenyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, a furanyl group, a thiophenyl group, a pyrrolyl group, a cyclopentenyl group, a silolyl group, a germolyl group, a benzofuranyl group, a benzothiophenyl group, an indolyl group, an indenyl group, a benzosilolyl group, a benzogermolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a dibenzosilolyl group, a dibenzogermolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzocarbazolyl group, a benzofluorenyl group, a benzonaphthosilolyl group, a benzonaphthogermolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dibenzocarbazolyl group, a dibenzofluorenyl group, a dinaphthosilolyl group, a dinaphthogermolyl group, a pyridinyl group, a biphenyl group, a terphenyl group, or any combination thereof.

### Claim 6 (depends on 1)

The heterocyclic compound of claim 1, wherein a group represented by
in Formula 1 is represented by one of Formulae 3-1 to 3-7:
wherein, in Formulae 3-1 to 3-7,
X3 is understood by referring to the description of X3 in claim 1,
X5 is O, S, N(R59), C(R59a)(R59b), Si(R59a)(R59b), or Ge(R59a)(R59b),
X6 is a single bond, O, S, N(R59c), C(R59d)(R59e), Si(R59d)(R59e), or Ge(R59d)(R59e),
R41 to R44 are each understood by referring to the description of R40 in claim 1,
R51 to R59, and R59a to R59e are each understood by referring to the description of R50 in claim 1, and
* indicates a binding site to an adjacent atom.

### Claim 7 (depends on 1)

The heterocyclic compound of claim 1, wherein a group represented by
in Formula 1 is represented by Formula 3-7, and at least one of R43 and R53 in Formula 3-7 is not hydrogen.

### Claim 8 (depends on 1)

The heterocyclic compound of claim 1, wherein the heterocyclic compound emits delayed fluorescence.

### Claim 9 (depends on 1)

The heterocyclic compound of claim 1, wherein the heterocyclic compound emits blue light.

### Claim 10 (depends on 1)

An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer located between the first electrode and the second electrode and comprising an emission layer,
wherein the organic layer comprises the heterocyclic compound of claim 1.

### Claim 11 (depends on 10)

The organic light-emitting device of claim 10, wherein the heterocyclic compound is included in the emission layer.

### Claim 12 (depends on 11)

The organic light-emitting device of claim 11, wherein the emission layer comprises a host and an emitter, the host is different from the emitter, and the heterocyclic compound is included in the emitter.

### Claim 13 (depends on 12)

The organic light-emitting device of claim 12, wherein a ratio of emission components emitted from the heterocyclic compound is in a range of about 70% to about 100%, based on total emission components emitted from the emission layer.

### Claim 14 (depends on 12)

The organic light-emitting device of claim 12, wherein the emission layer emits blue light.

### Claim 15 (depends on 11)

The organic light-emitting device of claim 11, wherein the emission layer comprises a host, an emitter, and a sensitizer, the host, the emitter, and the sensitizer are different from each other, and the heterocyclic compound is included in the sensitizer.

### Claim 16 (depends on 15)

The organic light-emitting device of claim 15, wherein a ratio of emission components emitted from the emitter is in a range of about 70% to about 100%, based on total emission components emitted from the emission layer.

### Claim 17 (depends on 12)

The organic light-emitting device of claim 12, wherein the host does not comprise a transition metal.

### Claim 18 (depends on 15)

The organic light-emitting device of claim 15, wherein the emitter is a fluorescence emitter.

### Claim 19 (depends on 10)

An electronic apparatus comprising the organic light-emitting device of claim 10.