# US 2025/0098538 A1 · Heterocyclic compound, organic light emitting device including the same, and electronic apparatus

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

- Number: US 2025/0098538 A1
- Document ID: US20250098538A1
- Status: Published application
- Kind: A1
- Application number: 18/816,804
- Filed: 2024-08-27
- Published: 2025-03-20
- Earliest claimed: 2023-08-30
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., LTD.
- Inventors: Junha Park; Changwoong Chu; Taeil Kim; Jangyeol Baek; Munki Sim
- Web page: https://patentgrep.com/patent/US20250098538A1

## CPC

- H10K 85/658: {Organoboranes}
- C07F 5/027: {Organoboranes and organoborohydrides}
- 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 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/121: {for assisting energy transfer, e.g. sensitization}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- 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 same, and an electronic apparatus including the organic light-emitting device. Descriptions of each substituent in Formula 1 are provided in the present specification.

## Claims

### Claim 1

A heterocyclic compound represented by Formula 1:
wherein, in Formula 1,
X1 and X2 are each independently O, S, Se, N(R1), C(═O), C(R1)(R2), or Si(R1)(R2),
A1 and A2 are each independently a C5-C60 carbocyclic group that is substituted with at least one deuterium or a C1-C60 heterocyclic group that is substituted with at least one deuterium,
A3 is a C5-C60 carbocyclic group or a C1-C60 heterocyclic group,
Q1 to Q3 are each independently a sterically shielding group,
k1 to k3 are each independently 0, 1, 2, 3, 4, 5, 6, 7, or 8,
at least one of k1 and k2 is 1, 2, 3, 4, 5, 6, 7, or 8,
R1, R2, R10, R20, and R30 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group that is unsubstituted or substituted with at least one deuterium, a C2-C60 alkenyl group that is unsubstituted or substituted with at least one deuterium, a C2-C60 alkynyl group that is unsubstituted or substituted with at least one deuterium, a C1-C60 alkoxy group that is unsubstituted or substituted with at least one deuterium, a C3-C10 cycloalkyl group that is unsubstituted or substituted with at least one deuterium, a C1-C10 heterocycloalkyl group that is unsubstituted or substituted with at least one deuterium, a C3-C10 cycloalkenyl group that is unsubstituted or substituted with at least one deuterium, a C1-C10 heterocycloalkenyl group that is unsubstituted or substituted with at least one deuterium, a C6-C60 aryl group that is unsubstituted or substituted with at least one deuterium, a C6-C60 aryloxy group that is unsubstituted or substituted with at least one deuterium, a C6-C60 arylthio group that is unsubstituted or substituted with at least one deuterium, a C1-C60 heteroaryl group that is unsubstituted or substituted with at least one deuterium, a C1-C60 heteroaryloxy group that is unsubstituted or substituted with at least one deuterium, a C1-C60 heteroarylthio group that is unsubstituted or substituted with at least one deuterium, a monovalent non-aromatic condensed polycyclic group that is unsubstituted or substituted with at least one deuterium, a monovalent non-aromatic condensed heteropolycyclic group that is unsubstituted or substituted with at least one deuterium, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2),
two or more neighboring ones selected from R1, R2, R10, R20, and R30 are optionally bonded together to form a C5-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a,
b10, b20, and b30 are each independently 0, 1, 2, 3, 4, 5, 6, 7, or 8,
R10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof; or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32), and
Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

### Claim 2 (depends on 1)

The heterocyclic compound of claim 1, wherein A1 and A2 are each independently a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an indole group, a pyridine group, a pyrimidine group, a carbazole group, a benzocarbazole group, a dibenzocarbazole group, a furan group, a benzofuran group, a dibenzofuran group, a naphthofuran group, a benzonaphthofuran group, a dinaphthofuran group, a thiophene group, a benzothiophene group, a dibenzothiophene group, a naphthothiophene group, a benzonaphthothiophene group, or a dinaphthothiophene group, each substituted with at least one deuterium, and
A3 is a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an indole group, a pyridine group, a pyrimidine group, a carbazole group, a benzocarbazole group, a dibenzocarbazole group, a furan group, a benzofuran group, a dibenzofuran group, a naphthofuran group, a benzonaphthofuran group, a dinaphthofuran group, a thiophene group, a benzothiophene group, a dibenzothiophene group, a naphthothiophene group, a benzonaphthothiophene group, or a dinaphthothiophene group.

### Claim 3 (depends on 1)

The heterocyclic compound of claim 1, wherein at least one selected from A1 and A2 has a deuterium substitution rate of 40% or more.

### Claim 4 (depends on 1)

The heterocyclic compound of claim 1, wherein the sterically shielding group is a substituted or unsubstituted carbocyclic group comprising three or more rings or a substituted or unsubstituted heterocyclic group comprising three or more rings.

### Claim 5 (depends on 1)

The heterocyclic compound of claim 1, wherein the sterically shielding group is represented by Formula Q-1:
wherein, in Formula Q-1,
A4 and A5 are each independently a C5-C60 carbocyclic group or a C1-C60 heterocyclic group,
R40 and R50 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group that is unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group that is unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkyl group that is unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkyl group that is unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkenyl group that is unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkenyl group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryl group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group that is unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group that is unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryl group that is unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryloxy group that is unsubstituted or substituted with at least one R10a, a C1-C60 heteroarylthio group that is unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed polycyclic group that is unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed heteropolycyclic group that is unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2),
two or more neighboring ones selected from R40 and R50 are optionally bonded together to form a C5-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a,
b40 and b50 are each independently 0, 1, 2, 3, 4, 5, 6, 7, or 8,
R10a and Q1 to Q3 are each as described in claim 1, and
* indicates a binding site to a neighboring atom.

### Claim 6 (depends on 1)

The heterocyclic compound of claim 1, wherein R1, R2, R10, R20, and R30 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C20 alkyl group, a C1-C20 alkoxy group, or a group represented by one selected from Formulae 5-1 to 5-26 and Formulae 6-1 to 6-55:
wherein, in Formulae 5-1 to 5-26 and 6-1 to 6-55,
Y31 and Y32 are each independently O, S, C(Z33)(Z34), N(Z33), or Si(Z33)(Z34),
Z31 to Z34 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkenyl group, a C1-C20 alkynyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, and a triazinyl group,
e2 is 1 or 2,
e3 is an integer from 1 to 3,
e4 is an integer from 1 to 4,
e5 is an integer from 1 to 5,
e6 is an integer from 1 to 6,
e7 is an integer from 1 to 7,
e9 is an integer from 1 to 9, and
* indicates a binding site to a neighboring atom.

### Claim 7 (depends on 1)

The heterocyclic compound of claim 1, wherein the heterocyclic compound represented by Formula 1 is a compound represented by one selected from Formulae 11-1 to 11-14:
wherein, in Formulae 11-1 to 11-14,
X1, X2, Q1, and Q2 are each as described in claim 1,
R11 to R13 are each independently the same as described in connection with R10 in claim 1,
at least one selected from R11 to R13 is deuterium,
R21 to R24 are each independently the same as described in connection with R20 in claim 1,
at least one selected from R21 to R24 in Formulae 11-1 to 11-4 is deuterium, and
at least one selected from R21 to R23 in Formulae 11-5 to 11-14 is deuterium, and
Z1 to Z3 are each independently Q3 or R30.

### Claim 8 (depends on 1)

The heterocyclic compound of claim 1, wherein the heterocyclic compound represented by Formula 1 is a compound represented by Formula 21:
wherein, in Formula 21,
X1 and X2 are each as described in claim 1,
R11 to R13 are each independently the same as described in connection with R10 in claim 1,
at least one selected from R11 to R13 is deuterium,
R21 to R23 are each independently the same as described in connection with R20 in claim 1,
at least one selected from R21 to R23 is deuterium,
Z1 to Z3 are each independently Q3 or R30,
R41 to R48 and R51 to R58 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group that is unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group that is unsubstituted or substituted with at least one R10a, a C3-C10cycloalkyl group that is unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkyl group that is unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkenyl group that is unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkenyl group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryl group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group that is unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group that is unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryl group that is unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryloxy group that is unsubstituted or substituted with at least one R10a, a C1-C60 heteroarylthio group that is unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed polycyclic group that is unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed heteropolycyclic group that is unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2),
two or more neighboring ones selected from R41 to R48 and R51 to R58 are optionally bonded together to form a C5-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a, and
R10a and Q1 to Q3 are each as described in claim 1.

### Claim 9 (depends on 1)

The heterocyclic compound of claim 1, wherein the heterocyclic compound represented by Formula 1 is selected from Compounds 1 to 60:

### Claim 10 (depends on 1)

A composition comprising at least one heterocyclic compound of claim 1.

### Claim 11 (depends on 1)

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

### Claim 12 (depends on 11)

The organic light-emitting device of claim 11, wherein the first electrode is an anode,
the second electrode is a cathode,
the interlayer further comprises: a hole transport region between the first electrode and the emission layer; and an electron transport region between the emission layer and the second electrode,
the hole transport region comprises at least one selected from a hole injection layer, a hole transport layer, a buffer layer, an emission auxiliary layer, and an electron blocking layer, and
the electron transport region comprises at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

### Claim 13 (depends on 11)

The organic light-emitting device of claim 11, wherein the emission layer comprises the heterocyclic compound.

### Claim 14 (depends on 13)

The organic light-emitting device of claim 13, wherein the emission layer comprises a host and a dopant, and
the dopant comprises the heterocyclic compound.

### Claim 15 (depends on 13)

The organic light-emitting device of claim 13, wherein the emission layer emits blue light having a maximum emission wavelength of about 410 nm to about 490 nm.

### Claim 16 (depends on 13)

The organic light-emitting device of claim 13, wherein the emission layer further comprises a sensitizer.

### Claim 17 (depends on 11)

An electronic apparatus comprising the organic light-emitting device of claim 11.

### Claim 18 (depends on 17)

The electronic apparatus of claim 17, further comprising a thin-film transistor, wherein the thin-film transistor comprises a source electrode and a drain electrode, and
the first electrode of the organic light-emitting device is electrically connected with at least one selected from the source electrode and the drain electrode of the thin-film transistor.

### Claim 19 (depends on 11)

A consumer product comprising the organic light-emitting device of claim 11.

### Claim 20 (depends on 19)

The consumer product of claim 19, wherein the consumer product is one selected from a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and/or light for signal, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a portable phone, a tablet personal computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality or augmented reality display, a vehicle, a video wall comprising a plurality of displays tiled together, a theater or stadium screen, a phototherapy device, and a signboard.