# US 11,299,502 B2 · Condensed cyclic compound and organic light-emitting device including condensed cyclic compound

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- Number: US 11,299,502 B2
- Document ID: US11299502B2
- Status: Granted
- Kind: B2
- Application number: 16/218,670
- Filed: 2018-12-13
- Published: 2019-12-12
- Granted: 2022-04-12
- Earliest claimed: 2018-06-12
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Sehun Kim; Jaejin Lyu
- Web page: https://patentgrep.com/patent/US11299502B2

## CPC

- C07F 5/027: {Organoboranes and organoborohydrides}
- C07F 5/02: Boron compounds
- C07F 7/0816: {said ring comprising Si as a ring atom}
- C09K 11/06: containing organic luminescent materials
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- 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 85/658: {Organoboranes}
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 2101/40: Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
- 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
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A condensed cyclic compound and an organic light-emitting device including the same are provided. When the condensed cyclic compound is used as an emission layer material in a device, the device may have excellent driving voltage, efficiency, and colorimetric purity. An organic light-emitting device including the condensed cyclic compound may have a low driving voltage, excellent efficiency, and a long lifespan.

## 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 and comprising an emission layer and at least one condensed cyclic compound represented by Formula 1:
wherein in Formulae 1, 2A, and 2B,
X11 is selected from C(R12)(R13), Si(R12)(R13), O, and S, and X12 is selected from C(R14)(R16), Si(R14)(R16), O, and S,
when X11 is O or S, X12 is selected from C(R14)(R15) and Si(R14)(R15),
when X12 is O or S, X11 is selected from C(R12)(R13) and Si(R12)(R13),
X21 and X22 are each independently selected from a single bond, C(R24)(R25), Si(R24)(R25), N(R24), O, and S,
X23 is selected from a single bond, C(R26)(R27), Si(R26)(R27), N(R26), O, and S, and X24 is selected from a single bond, C(R28)(R29), Si(R28)(R29), N(R28), O, and S, provided that X23 and X24 are not each a single bond at the same time,
A21 to A25 are each independently selected from a C5-C30 carbocyclic group and a C1-C30 heterocyclic group,
L21 is selected from a single bond, a substituted or unsubstituted C5-C60 carbocyclic group, and a substituted or unsubstituted C1-C60 heterocyclic group,
a21 is an integer from 1 to 5,
R1 to R3 are each independently selected from a group represented by Formula 2A, a group represented by Formula 2B, 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 C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio 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), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2), provided that at least one selected from R1 to R3 is selected from the group represented by Formula 2A and the group represented by Formula 2B,
R4 to R15 and R21 to R29 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 C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio 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), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
two adjacent groups selected from R1 to R6 and R9 to R15 and/or two adjacent groups selected from R21 to R29 are optionally bound to form a saturated ring or an unsaturated ring,
b21 to b23 are each independently an integer from 1 to 10,
provided that in Formula 1, i) when X11 is C(R12)(R13), X12 is C(R14)(R15), O, or S, and R12 and R13 and/or R14 and R15 are not bound to each other, or ii) when X11 is C(R12)(R13), O, or S, X12 is C(R14)(R15), and R12 and R13 and/or R14 and R15 are not bound to each other, R1 to R3 does not comprise a group represented by Formula 2A-a:
wherein in Formula 2A-a, X201 is a single bond, C(R24)(R25), N(R24), O, or S, R24 and R25 are not bound, and
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 C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio 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 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 and an electron transport region between the emission layer and the second electrode,
wherein the hole transport region comprises a hole injection layer, a 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 1)

The organic light-emitting device of claim 1, wherein the emission layer comprises the condensed cyclic compound.

### Claim 4 (depends on 3)

The organic light-emitting device of claim 3, wherein the emission layer consists of the condensed cyclic compound, or
the emission layer further comprises a host, and a content of the condensed cyclic compound is in a range of about 0.1 parts to 50 parts by weight, based on 100 parts by weight of the emission layer.

### Claim 5 (depends on 3)

The organic light-emitting device of claim 3, wherein the condensed cyclic compound comprised in the emission layer is a thermal activated delayed fluorescence (TADF) emitter, and the emission layer emits delayed fluorescence.

### Claim 6 (depends on 3)

The organic light-emitting device of claim 3, wherein the emission layer emits blue light having a maximum emission wavelength in a range of about 420 nanometers (nm) to about 470 nm.

### Claim 7 (depends on 2)

The organic light-emitting device of claim 2, wherein the hole transport region comprises a p-dopant, wherein a lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant is −3.5 eV or less.

### Claim 8

A condensed cyclic compound represented by Formula 1:
wherein in Formulae 1, 2A, and 2B,
X11 is selected from C(R12)(R13), Si(R12)(R13), O, and S, and X12 is selected from C(R14)(R16), Si(R14)(R16), O, and S,
when X11 is O or S, X12 is selected from C(R14)(R15) and Si(R14)(R16),
when X12 is O or S, X11 is selected from C(R12)(R13) and Si(R12)(R13),
X21 and X22 are each independently selected from a single bond, C(R24)(R25), Si(R24)(R25), N(R24), O, and S,
X23 is selected from a single bond, C(R26)(R27), Si(R26)(R27), N(R26), O, and S, and X24 is selected from a single bond, C(R28)(R29), Si(R28)(R29), N(R28), O, and S, provided that X23 and X24 are not each a single bond at the same time,
A21 to A25 are each independently selected from a C5-C30 carbocyclic group and a C1-C30 heterocyclic group,
L21 is selected from a single bond, a substituted or unsubstituted C5-C60 carbocyclic group, and a substituted or unsubstituted C1-C60 heterocyclic group,
a21 is an integer from 1 to 5,
R1 to R3 are each independently selected from a group represented by Formula 2A, a group represented by Formula 2B, 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 C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio 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), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2), provided that at least one selected from R1 to R3 is selected from the group represented by Formula 2A and the group represented by Formula 2B,
R4 to R15 and R21 to R29 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 C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio 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), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(a), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
two adjacent groups selected from R1 to R6 and R9 to R15 and/or two adjacent groups selected from R21 to R29 are optionally bound to form a saturated ring or an unsaturated ring, and
b21 to b23 are each independently an integer from 1 to 10,
provided that in Formula 1, i) when is C(R12)(R13), X12 is C(R14)(R15), O, or S, and R12 and R13 and/or R14 and R16 are not bound to each other, or ii) when is C(R12)(R13), O, or S, X12 is C(R14)(R15), and R12 and Ria and/or R14 and R15 are not bound to each other, R1 to R3 does not comprise a group represented by Formula 2A-a:
wherein in Formula 2A-a, X201 is a single bond, C(R24)(R25), N(R24), O, or S, R24 and R25 are not bound, and
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 C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio 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 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 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 condensed cyclic compound of claim 8, wherein
X11 is C(R12)(R13), and X12 is C(R14)(R15),
X11 is C(R12)(R13), and X12 is Si(R14)(R15),
X11 is C(R12)(R13), and X12 is O,
X11 is C(R12)(R13), and X12 is S,
X11 is Si(R12)(R13), and X12 is Si(R14)(R15),
X11 is Si(R12)(R13), and X12 is O, or
X11 is Si(R12)(R13), and X12 is S.

### Claim 10 (depends on 8)

The condensed cyclic compound of claim 8, wherein
in Formula 2A, X21 is selected from a single bond, C(R24)(R25), and Si(R24)(R25), and
in Formula 2B, X22 is selected from a single bond, C(R24)(R25), and Si(R24)(R25), X23 is selected from a single bond, C(R26)(R27), Si(R26)(R27), N(R26), O, and S, and X24 is selected from a single bond, C(R28)(R29), Si(R28)(R29), and N(R28).

### Claim 11 (depends on 8)

The condensed cyclic compound of claim 8, wherein
i) X11 is Si(R12)(R13), X12 is Si(R14)(R15), and at least one selected from R1 to R3 is the group represented by Formula 2B,
ii) is selected from C(R12)(R13), Si(R12)(R13), O, and S, X12 is selected from C(R14)(1R15), O, and S, and at least one selected from R1 to R3 is the group represented by Formula 2B,
iii) is selected from C(R12)(R13), O, and S, X12 is selected from C(R14)(R15), Si(R14)(R15), O, and S, and at least one selected from R1 to R3 is the group represented by Formula 2B,
iv) X11 is Si(R12)(R13), X12 is Si(R14)(R15), and at least one selected from R1 to R3 is the group represented by Formula 2A,
v) X11 is Si(R12)(R13), and at least one selected from R1 to R3 is the group represented by Formula 2A,
vi) X12 is Si(R14)(R15), and at least one selected from R1 to R3 is the group represented by Formula 2A, or
vii) X11 is selected from C(R12)(R13), O, and S, X12 is selected from C(R14)(1R15), O, and S, at least one selected from R1 to R3 is the group represented by Formula 2A, and R24 and R25 are bound to form a saturated ring or an unsaturated ring.

### Claim 12 (depends on 8)

The condensed cyclic compound of claim 8, wherein in Formula 2A, A21 and A22 are each independently selected from a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, a triphenylene group, a pyrene group, a chrysene group, a pyridine group, a pyrazine group, a pyrimidine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a 2,6-naphthyridine group, a 1,8-naphthyridine group, a 1,5-naphthyridine group, a 1,6-naphthyridine group, a 1,7-naphthyridine group, a 2,7-naphthyridine group, a quinoxaline group, a quinazoline group, a phenanthridine group, and a phenanthroline group.

### Claim 13 (depends on 8)

The condensed cyclic compound of claim 8, wherein in Formula 2B, A23 to A25 are each independently selected from a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, a triphenylene group, a pyrene group, a chrysene group, a pyridine group, a pyrazine group, a pyrimidine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a 2,6-naphthyridine group, a 1,8-naphthyridine group, a 1,5-naphthyridine group, a 1,6-naphthyridine group, a 1,7-naphthyridine group, a 2,7-naphthyridine group, a quinoxaline group, a quinazoline group, a phenanthridine group, a phenanthroline group, a benzofuran group, a benzothiophene group, an indene group, an indole group, a furopyridine group, a thienopyridine group, a cyclopentapyridine group, a pyrrolopyridine group, a dibenzofuran group, a dibenzothiophene group, a fluorene group, a carbazole group, a benzonaphthofuran group, a benzonapthothiophene group, a benzofluorene group, a benzocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dibenzofluorene group, a dibenzocarbazole group, a benzoxazole group, a benzothiazole group, a benzimidazole group, a naphthofuran group, a naphthothiophene group, a spiro-bifluorene group, and a spiro-fluorene-indene group.

### Claim 14 (depends on 8)

The condensed cyclic compound of claim 8, wherein L21 is selected from a single bond, 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-bifluorene group, a benzofluorene 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; and
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-bifluorene group, a benzofluorene 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-C29 aryl group, a C1-C20 heteroaryl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), and —S(═O)2(Q31),
wherein Q31 to Q33 are each independently selected from hydrogen, 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-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 aryl group substituted with a C1-C60 alkyl 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.

### Claim 15 (depends on 8)

The condensed cyclic compound of claim 8, wherein R1 to R3 are each independently selected from the group represented by Formula 2A, the group represented by Formula 2B, hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl 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), and —N(Q1)(Q2),
R4 to R15 and R21 to R29 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl 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), and —N(Q1)(Q2),
wherein Q1 to Q3 are each independently selected from hydrogen, deuterium, a C1-C60 alkyl group, a C1-C60 alkoxy 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
R12 and R13, R14 and R15, R24 and R25, R26 and R27, and/or R28 and R29 are optionally bound to each other to form a saturated ring or an unsaturated ring.

### Claim 16 (depends on 8)

The condensed cyclic compound of claim 8, wherein R12 and R13, R14 and R15, R24 and R25, R26 and R27, and/or R28 and R29 are bound to each other to form a group represented by Formula 9-1:
wherein, in Formula 9-1,
X91 is selected from a single bond, O, S, Se, C(R93)(R94), Si(R93)(R94), and Ge(R93)(R94),
A91 and A92 are each independently selected from a C5-C30 carbocyclic group and a C1-C30 heterocyclic group,
R91 and R92 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 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 C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio 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), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
wherein Q1 to Q3 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,
b91 and b92 are each independently an integer from 1 to 10, and
* indicates binding site to a carbon atom in Formulae 1, 2A, and 2B.

### Claim 17 (depends on 8)

The condensed cyclic compound of claim 8, wherein the group represented by Formula 2B is represented by one of Formulae 2B-1 to 2B-5:
wherein, in Formulae 2B-1 to 2B-5,
b22 is 1 or 2, b24 is an integer from 1 to 4,
X25 is selected from C(R30)(R31), Si(R30)(R31), N(R30), O, and S,
R30 and R31 are each defined the same as R1 in Formula 1, and
A23, A25, X22 to X24, L21, a21, R21 to R23, b21, and b23 are each defined the same as those in Formula 2B.

### Claim 18 (depends on 8)

The condensed cyclic compound of claim 8, wherein the group represented by Formula 2B is represented by one of Formulae 2B-1(1) to 2B-5(2):
wherein, in Formulae 2B-1(1) to 2B-5(2),
X22 is selected from C(R24)(R25), Si(R24)(R25), N(R24), O, and S,
X23 is selected from C(R26)(R27), Si(R26)(R27), N(R26), O, and S,
X24 is selected from C(R28)(R29), Si(R28)(R29), N(R28), O, and S,
X25 is selected from C(R30)(R31), Si(R30)(R31), N(R30), O, and S,
R30 and R31 are each defined the same as R1 in Formula 1,
b21, b23, and b24 are each independently an integer from 1 to 4, b22 is 1 or 2, and
L21, a21, and R21 to R29 are each defined the same as those in Formula 2B.

### Claim 19 (depends on 8)

The condensed cyclic compound of claim 8, wherein the group represented by Formula 2B is represented by one of Formulae 2B-1-a to 2B-5-b:
wherein, in Formulae 2B-1-a to 2B-5-b,
X23 is selected from C(R26)(R27), Si(R26)(R27), N(R26), O, and S,
X24 is selected from C(R28)(R29), Si(R28)(R29), N(R28), O, and S,
X25 is selected from C(R30)(R31), Si(R30)(R31), N(R30), O, and S,
X202 to X204 are each independently selected from C(R32)(R33) and Si(R32)(R33),
R30 and R33 are each defined the same as R1 in Formula 1,
b21, b23, and b24 are each independently an integer from 1 to 4, b22 is 1 or 2, and
L21, a21, and R21 to R29 are each defined the same as those in Formula 2B.

### Claim 20 (depends on 8)

The condensed cyclic compound of claim 8, being selected from Compounds 1 to 23: