# US 11,078,210 B2 · Heterocyclic compound and organic light emitting device including the same

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- Number: US 11,078,210 B2
- Document ID: US11078210B2
- Status: Granted
- Kind: B2
- Application number: 16/114,032
- Filed: 2018-08-27
- Published: 2019-08-15
- Granted: 2021-08-03
- Earliest claimed: 2018-02-09
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Munki Sim; Junha Park; Hyoyoung Lee; Youngkook Kim; Seokhwan Hwang
- Web page: https://patentgrep.com/patent/US11078210B2

## CPC

- C07D 491/048: the oxygen-containing ring being five-membered
- 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
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 50/171: {Electron injection layers}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A a heterocyclic compound and an organic light-emitting device including the same are presented. The organic light-emitting device includes two electrodes and an organic layer between the electrodes that includes an emission layer and at least one heterocyclic compound, which is represented by the following Formula: wherein ring A1 is selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group, X1 is O, S, or Se, and Li is selected from a substituted or unsubstituted C5-C60 carbocyclic group, a substituted or unsubstituted C1-C60 heterocyclic group, *—Si(Q1)(Q2)-*′, *—P(═O)(Q1)-*′, *—P(═O)2—*′, *—P(═S)(Q1)-*′, *—P(═S)2—*′, *—S(═O)(Q1)-*′, and *—S(═O)2—*′. Other variables in the Formula are defined, and more specific structures are disclosed in the specification.

## Claims

### Claim 1

An organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer comprising an emission layer and an electron transport region between the emission layer and the second electrode, the electron transport region comprising at least one heterocyclic compound represented by Formula 1:
wherein, in Formula 1,
ring A1 is selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group,
X1 is O, S, or Se,
L1 is selected from a substituted or unsubstituted C5-C60 carbocyclic group, a substituted or unsubstituted C1-C60 heterocyclic group, *—Si(Q1)(Q2)—*′, *—P(═O)(Q1)-*′, *—P(═O)2—*′, *—P(═S)(Q1)-*′, *—P(═S)2—*′, *—S(═O)(Q1)-*′, and *—S(═O)2—*′,
a1 is an integer from 0 to 5; and when a1 is 0, —(L1)a1- is a single bond, and when a1 is 2 or greater, at least two L1(s) are identical to or different from each other,
Ar1 is selected from 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, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —C(═O)(Q1), —N(Q1)(Q2), —P(═O)(Q1)(Q2), —P(═O)2(Q1), —P(═S)(Q1)(Q2), —P(═S)2(Q1), —S(═O)(Q1)(Q2), and —S(═O)2(Q1)(Q2),
b1 is an integer from 1 to 10; and when b1 is 2 or greater, at least two Ar1(s) are identical to or different from each other,
R1 and R2 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 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, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —C(═O)(Q1), —N(Q1)(Q2), —P(═O)(Q1)(Q2), —P(═O)2(Q1), —P(═S)(Q1)(Q2), —P(═S)2(Q1), —S(═O)(Q1)(Q2), and —S(═O)2(Q1)(Q2),
c1 is an integer from 1 to 6; and when c1 is 2 or greater, at least two R1(s) are identical to or different from each other,
c2 is an integer of 1 or 2; and when c2 is 2, at least two R2(s) are identical to or different from each other,
d1 is an integer from 1 to 5,
at least one substituent of the substituted C5-C60 carbocyclic group, the substituted C1-C60 heterocyclic group, 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 selected from:
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, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
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-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from 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, 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 C10-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 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, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32).
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 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-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 C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
* indicates a binding site to an adjacent atom.

### Claim 2 (depends on 1)

The organic light-emitting device of claim 1, wherein
the first electrode is an anode,
the second electrode is a cathode,
the organic layer further comprises a hole transport region between the first electrode and the emission layer,
the hole transport region comprises a hole injection layer, a first hole transport layer, a second hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof, and
the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

### Claim 3 (depends on 2)

The organic light-emitting device of claim 2, wherein the electron transport region comprises the electron transport layer and the electron injection layer, and at least one of the electron transport layer and the electron injection layer comprises the at least one heterocyclic compound.

### Claim 4 (depends on 2)

The organic light-emitting device of claim 2, wherein the electron transport region comprises the electron transport layer, and the electron transport layer comprises the at least one heterocyclic compound.

### Claim 5 (depends on 2)

The organic light-emitting device of claim 2, wherein the electron transport region comprises a metal-containing material, and the metal-containing material comprises a lithium (Li) complex.

### Claim 6 (depends on 2)

The organic light-emitting device of claim 2, wherein the emission layer comprises the at least one heterocyclic compound.

### Claim 7 (depends on 6)

The organic light-emitting device of claim 6, wherein the emission layer further comprises a dopant, wherein a content of the at least one heterocyclic compound is greater than that of the dopant in the emission layer, and the dopant is a phosphorescent dopant or a fluorescent dopant.

### Claim 8

A heterocyclic compound represented by Formula 1:
wherein, in Formula 1,
ring A1 is selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group,
X1 is O, S, or Se,
L1 is selected from a substituted or unsubstituted C5-C60 carbocyclic group, a substituted or unsubstituted C1-C60 heterocyclic group, *13 Si(Q1)(Q2)-*′, *—P(═O)(Q1)-*′, * P(═O)2—*′, *—P(═S)(Q1)-*′, *—P(═S)2—*′, *—S(═O)(Q1)-*′, and *—S(═O)2—*′,
a1 is an integer from 0 to 5; and when a1 is 0, —(L1)a1—is a single bond, and when a1 is 2 or greater, at least two L1(s) are identical to or different from each other,
Ar1 is selected from groups represented by Formulae 5-1 to 5-28, 5-30 to 5-35, 5-37, 5-38, —Si(Q1)(Q2)(Q3), —P(═O)(Q1)(Q2), —P(═O)2(Q1), —P(═S)(Q1)(Q2), —P(═S)2(Q1), —S(═O)(Q1)(Q2), and —S(═O)2(Q1):
wherein, in Formulae 5-1 to 5-28, 5-30 to 5-35, 5-37, and 5-38,
Y31 is O, S, C(Z33)(Z34), N(Z35), Si(Z36)(Z37), or P(═O)(Z38),
Z31 to Z38 are each independently selected from hydrogen, deuterium, —F, —CI, —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 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-fluorene-benzofluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —Si(Q31)(Q32)(Q33), and P(═O)(Q31)(Q32),
wherein Q1 to Q3 and Q31 to Q33 are each independently selected from a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,
e2 is an integer from 0 to 2; and when e2 is 2, two Z32(s) are identical to or different from each other,
e3 is an integer from 0 to 3; and when e3 is 2 or greater, at least two Z31(s) are identical to or different from each other, and at least two Z32(s) are identical to or different from each other,
e4 is an integer from 0 to 4; and when e4 is 2 or greater, at least two Z31(s) are identical to or different from each other, and at least two Z32(s) are identical to or different from each other,
e5 is an integer from 0 to 5; and when e5 is 2 or greater, at least two Z31(s) are identical to or different from each other, and at least two Z32(s) are identical to or different from each other,
e6 is an integer from 0 to 6; and when e6 is 2 or greater, at least two Z31(s) are identical to or different from each other, and at least two Z32(s) are identical to or different from each other,
e7 is an integer from 0 to 7; and when e7 is 2 or greater, at least two Z31(s) are identical to or different from each other,
e9 is an integer from 0 to 9; and when e9 is 2 or greater, at least two Z31(s) are identical to or different from each other, and
* indicates a binding site to an adjacent atom,
b1 is an integer from 1 to 10; and when b1 is 2 or greater, at least two Ar1(s) are identical to or different from each other,
R1 is 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 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 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, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —C(═O)(Q1), —N(Q1)(Q2), —P(═O)(Q1)(Q2), —P(═O)2(Q1), —P(═S)(Q1)(Q2), —P(═S)2(Q1), —S(═O)(Q1)(Q2), and —S(═O)2(Q1)(Q2),
R2 is 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 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 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —C(═O)(Q1), —N(Q1)(Q2), —P(═O)(Q1)(Q2), —P(═O)2(Q1), —P(═S)(Q1)(Q2), —P(═S)2(Q1), —S(═O)(Q1)(Q2), and —S(═O)2(Q1)(Q2),
c1 is an integer from 1 to 6; and when c1 is 2 or greater, at least two R1(s) are identical to or different from each other,
c2 is an integer of 1 or 2; and when c2 is 2, at least two R2(s) are identical to or different from each other,
d1 is an integer from 1 to 5,
at least one substituent of the substituted C5-C60 carbocyclic group, the substituted C1-C60 heterocyclic group, 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 selected from:
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, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
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-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from 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, 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-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 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-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 C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
* indicates a binding site to an adjacent atom.

### Claim 9 (depends on 8)

The heterocyclic compound of claim 8, wherein ring A1 is selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a pyrrole group, an indole group, an indene group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an iso-oxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group.

### Claim 10 (depends on 8)

The heterocyclic compound of claim 8, wherein L1 is selected from a benzene group, a pentalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, an indacene group, an acenaphthalene group, a fluorene group, a spiro-fluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphenylene group, a hexacene group, a pyrrole group, an imidazole group, a pyrazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an isoindole group, an indole group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a carbazole group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzoxazole group, a benzimidazole group, a furan group, a benzofuran group, a thiophene group, a benzothiophene group, a thiazole group, an isothiazole group, a benzothiazole group, an iso-oxazole group, an oxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a benzoxazole group, a dibenzofuran group, a dibenzothiophene group, a benzocarbazole group, and a dibenzocarbazole group;
a benzene group, a pentalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, an indacene group, an acenaphthalene group, a fluorene group, a spiro-fluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphenylene group, a hexacene group, a pyrrole group, an imidazole group, a pyrazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an isoindole group, an indole group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a carbazole group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzoxazole group, a benzimidazole group, a furan group, a benzofuran group, a thiophene group, a benzothiophene group, a thiazole group, an isothiazole group, a benzothiazole group, an iso-oxazole group, an oxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a benzoxazole group, a dibenzofuran group, a dibenzothiophene group, a benzocarbazole group, and a dibenzocarbazole group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C1-C20 heteroaryl group, and —Si(Q31)(Q32)(Q33); and
*—Si(Q1)(Q2)-*′, *—P(═O)(Q1)-*′, *—P(═O)2*′, *—P(═S)(Q1)-*′, *—P(═S)2—*′, *—S(═O)(Q1)-*′, and *—S(═O)2—*′,
wherein Q1, Q2, and Q31 to Q33 are each independently selected from a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C1-C20 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and
* and *′ each indicate a binding site to an adjacent atom.

### Claim 11 (depends on 8)

The heterocyclic compound of claim 8, wherein L1 is selected from groups represented by Formulae 3-1 to 3-50, *—Si(Q1)(Q2)*′, *—P(═O)(Q1)*′, *—P(═Q)2*′, *—P(═S)(Q1)*′, *—P(═S)2*′ *—S(═O)(Q1)-*′, and *—S(═O)2*′:
wherein, in Formulae 3-1 to 3-50,
Y1 is selected from O, S, C(Z3)(Z4), N(Z5), and Si(Z6)(Z7),
Z1 to Z7 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 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q31)(Q32)(Q33),
d2 is an integer from 0 to 2; and when d2 is 2, two Z1(s) are identical to or different from each other,
d3 is an integer from 0 to 3; and when d3 is 2 or greater, at least two Z1(s) are identical to or different from each other, and at least two Z2(s) are identical to or different from each other,
d4 is an integer from 0 to 4; and when d4 is 2 or greater, at least two Z1(s) are identical to or different from each other, and at least two Z2(s) are identical to or different from each other,
d5 is an integer from 0 to 5; and when d5 is 2 or greater, at least two Z1(s) are identical to or different from each other, and at least two Z2(s) are identical to or different from each other,
d6 is an integer from 0 to 6; and when d6 is 2 or greater, at least two Z1(s) are identical to or different from each other, and at least two Z2(s) are identical to or different from each other,
d8 is an integer from 0 to 8; and when d8 is 2 or greater, at least two Z1(s) are identical to or different from each other,
wherein Q1, Q2, and Q31 to Q33 are each independently selected from a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, and
* and *′ each indicate a binding site to an adjacent atom.

### Claim 12 (depends on 8)

The heterocyclic compound of claim 8, wherein Ar1 is selected from groups represented by Formulae 6-1 to 6-86 and 6-91 to 6-97, —Si(Q1)(Q2)(Q3), and —P(═O)(Q1)(Q2):
wherein, in Formulae 6-1 to 6-97,
“Ph” represents a phenyl group, and
Q1 to Q3 are each a phenyl group, and
* indicates a binding site to an adjacent atom.

### Claim 13 (depends on 8)

The heterocyclic compound of claim 8, wherein R1 is 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 alkoxy group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a phenanthrolinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, and
R2 is 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 alkoxy group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group.

### Claim 14 (depends on 8)

The heterocyclic compound of claim 8, wherein b1 is an integer from 1 to 3.

### Claim 15 (depends on 8)

The heterocyclic compound of claim 8, wherein the heterocyclic compound is represented by any one of Formulae 1A to 1E:
wherein, in Formulae 1A to 1E,
X1, L1, a1, Ar1, and b1 are each as defined in claim 8,
R11, R12, and R13 are each defined the same as R1 in claims 8, and
R21 and R22 are each defined the same as R2 in claim 8.

### Claim 16 (depends on 8)

The heterocyclic compound of claim 8, wherein the heterocyclic compound is represented by any one of Formulae 1A-1 to 1A-3:
wherein in Formulae 1A-1 to 1A-3,
L1, a1, Ar1, and b1 are each as defined in claims 8, and
R111 is defined the same as R1 in claim 8.

### Claim 17 (depends on 8)

The heterocyclic compound of claim 8, wherein the heterocyclic compound is selected from Compounds 1 to 41 and 51 to 56: