# US 12,225,817 B2 · Condensed cyclic compound and organic light-emitting device including the same

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- Number: US 12,225,817 B2
- Document ID: US12225817B2
- Status: Granted
- Kind: B2
- Application number: 17/739,532
- Filed: 2022-05-09
- Published: 2022-08-25
- Granted: 2025-02-11
- Earliest claimed: 2015-09-09
- Assignees: Samsung Electronics Co., Ltd.; Samsung SDI Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.; Samsung SDI Co., Ltd.
- Inventors: Sangmo Kim; Hyunjung Kim; Soonok Jeon; Yeonsook Chung; Miyoung Chae; Dalho Huh; Eunsuk Kwon; Jongsoo Kim; Myungsun Sim
- Web page: https://patentgrep.com/patent/US12225817B2

## CPC

- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C07D 209/94: containing carbocyclic rings other than six-membered
- C07D 487/04: Ortho-condensed systems
- C07D 491/04: Ortho-condensed systems
- C07D 491/048: the oxygen-containing ring being five-membered
- C07D 495/04: Ortho-condensed systems
- C07D 513/04: 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 11/025: {non-luminescent particle coatings or suspension media}
- C09K 11/06: containing organic luminescent materials
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/342: {comprising iridium}
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 85/653: {comprising only oxygen as heteroatom}
- 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

A condensed cyclic compound represented by Formula 1: Ar1-L1-L2-Ar2 Formula 1 wherein Ar1, Ar2, L1, and L2 are the same as described in the specification.

## Claims

### Claim 1

An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode and comprising an emission layer,
wherein the emission layer comprises a host and a dopant, wherein the host comprises one or more of a condensed cyclic compound represented by Formula 1:
in Formulae 1 to 5,
Ar1 is a group represented by Formula 2,
Ar2 is a group represented by Formula 3,
CY1 is selected from a fluorene group, a carbazole group, and a dibenzofuran group,
CY2 and CY3 are each a benzene group,
i) L1 is a group represented by Formula 4 and L2 is a group represented by Formula 5;
ii) L1 is a group represented by Formula 5 and L2 is a group represented by Formula 4; or
iii) L1 and L2 are each independently a group represented by Formula 4,
CY4 and CY5 are each independently selected from C5-C30 carbocyclic groups,
R1 to R4, R10, R20 and R30 are each independently selected from a hydrogen, a deuterium, a cyano group (CN), 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 C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryloxy group, a substituted or unsubstituted C2-C60 heteroarylthio group, a substituted or unsubstituted C3-C60 heteroarylalkyl 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(Q4)(Q5), and —B(Q6)(Q7),
R40 and R50 are each independently selected from a hydrogen, a deuterium, 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 C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryloxy group, a substituted or unsubstituted C2-C60 heteroarylthio group, a substituted or unsubstituted C3-C60 heteroarylalkyl 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(Q4)(Q5), and —B(Q6)(Q7),
a1 to a5 are each independently an integer of 0 to 10,
each of * and *′ is a binding site to a neighboring atom,
at least one substituent of the substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C3-C10 cycloalkyl group, substituted C1-C10 heterocycloalkyl group, substituted C3-C10 cycloalkenyl group, substituted C1-C10 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C7-C60 arylalkyl group, substituted C1-C60 heteroaryl group, substituted C2-C60 heteroaryloxy group, substituted C2-C60 heteroarylthio group, substituted C3-C60 heteroarylalkyl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
a deuterium, —CD3, —CD2H, —CDH2, a cyano 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 a deuterium, —CD3, —CD2H, —CDH2, a cyano 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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q14)(Q15) and —B(Q16)(Q17);
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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl 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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —CD3, —CD2H, —CDH2, a cyano group, a C1-Coo 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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q24)(Q25) and —B(Q26)(Q27); and
—Si(Q31)(Q32)(Q33), —N(Q34)(Q35) and —B(Q36)(Q37), and
Q1 to Q7, Q11 to Q17, Q21 to Q27 and Q31 to Q37 are each independently selected from a hydrogen, a deuterium, a cyano 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 C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryloxy group, a substituted or unsubstituted C2-C60 heteroarylthio group, a substituted or unsubstituted C3-C60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

### Claim 2 (depends on 1)

The organic light-emitting device of claim 1, wherein
Ar1 is selected from groups represented by Formulae 2-1 to 2-6, and
Ar2 is selected from groups represented by Formula 3-7:
in Formulae 2-1 to 2-6 and 3-7,
X1 is C(R17)(R18), N(R19), O,
R1 to R4 are each independently the same as described in claim 1,
R11 to R19 are each independently the same as R10 in claim 1,
R21 to R24 are each independently the same as R20 in claim 1,
R31 to R34 are each independently the same as R30 in claim 1, and
is a binding site to a neighboring atom.

### Claim 3 (depends on 2)

The organic light-emitting device of claim 2, wherein
R1 to R4, R11 to R19, R21 to R24 and R31 to R34 are each independently selected from
a hydrogen, a deuterium, a cyano group (CN), a C1-C20 alkyl group and a C1-C20 alkoxy group;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from a deuterium, a cyano group (CN), a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;
a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;
a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, a cyano group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and —Si(Q31)(Q32)(Q33); and
—Si(Q1)(Q2)(Q3), and
Q1 to Q3 and Q31 to Q33 are each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.

### Claim 4 (depends on 2)

The organic light-emitting device of claim 2, wherein
X1 is O.

### Claim 5 (depends on 1)

The organic light-emitting device of claim 1, wherein
CY4 and CY5 are each independently selected from a benzene group, a naphthalene group, a fluorene group, a carbazole group, a dibenzofuran group, and a dibenzothiophene group.

### Claim 6 (depends on 1)

The organic light-emitting device of claim 1, wherein the condensed cyclic compound is represented by one of Formulae 1-1 to 1-3:
in Formulae 1-1 and 1-3,
Ar1 and Ar2 are the same as in claim 1,
R41 to R48 are each independently the same as R40 in claim 1, and
R51 to R54 are each independently the same as R50 in claim 1.

### Claim 7 (depends on 1)

The organic light-emitting device of claim 1,
wherein the host comprises a compound selected from Compounds 33 to 44, 49, 54, 57 57 to 75, 80 to 85, 90 and 103 to 108:

### Claim 8 (depends on 1)

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

### Claim 9 (depends on 1)

The organic light-emitting device of claim 1, wherein
an amount of the host is greater than an amount of the dopant.

### Claim 10

A condensed cyclic compound represented by Formula 1:
in Formulae 1 to 5,
Ar1
is a group represented by Formula 2,
Ar2 is a group represented by Formula 3,
CY1 is selected from a fluorene group, a carbazole group, or a dibenzofuran group,
CY2 and CY3 are each a benzene group,
i) Li is a group represented by Formula 4 and L2 is a group represented by Formula 5; ii) L1 is a group represented by Formula 5 and L2 is a group represented by Formula 4; or iii) L1 and L2 are each independently a group represented by Formula 4,
CY4 and CY5 are each independently selected from C5-C30 carbocyclic groups,
R1 to R4, R10, R20 and R30 are each independently selected from a hydrogen, a deuterium, a cyano group (CN), 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 C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryloxy group, a substituted or unsubstituted C2-C60 heteroarylthio group, a substituted or unsubstituted C3-C60 heteroarylalkyl 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(Q4)(Q5), and —B(Q6)(Q7),
R40 and R50 are each independently selected from a hydrogen, a deuterium, 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 C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryloxy group, a substituted or unsubstituted C2-C60 heteroarylthio group, a substituted or unsubstituted C3-C60 heteroarylalkyl 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(Q4)(Q5), and —B(Q6)(Q7),
a1 to a5 are each independently an integer of 0 to 10,
each of * and *′ is a binding site to a neighboring atom,
at least one substituent of the substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C3-C10 cycloalkyl group, substituted C1-C10 heterocycloalkyl group, substituted C3-C10 cycloalkenyl group, substituted C1-C10 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C7-C60 arylalkyl group, substituted C1-C60 heteroaryl group, substituted C2-C60 heteroaryloxy group, substituted C2-C60 heteroarylthio group, substituted C3-C60 heteroarylalkyl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
a deuterium, —CD3, —CD2H, —CDH2, a cyano 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 a deuterium, —CD3, —CD2H, —CDH2, a cyano 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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q14)(Q15) and —B(Q16)(Q17);
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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl 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 Co-Coo aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —CD3, —CD2H, —CDH2, a cyano 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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q24)(Q25) and —B(Q26)(Q27); and
—Si(Q31)(Q32)(Q33), —N(Q34)(Q35) and —B(Q36)(Q37), and
Q1 to Q7, Q11 to Q17, Q21 to Q27 and Q31 to Q37 are each independently selected from a hydrogen, a deuterium, a cyano 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 C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryloxy group, a substituted or unsubstituted C2-C60 heteroarylthio group, a substituted or unsubstituted C3-C60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

### Claim 11 (depends on 10)

The condensed cyclic compound of claim 10, wherein
Ar1 is selected from groups represented by Formulae 2-1 to 2-6, and
Ar2 is selected from a group represented by Formula 3-7:
in Formulae 2-1 to 2-6 and 3-7,
X1 is C(R17)(R18), N(R19), or O,
R1 to R4 are each independently the same as described in claim 10,
R11 to R19 are each independently the same as R10 in claim 10,
R21 to R24 are each independently the same as R20 in claim 10,
R31 to R34 are each independently the same as R30 in claim 10, and
is a binding site to a neighboring atom.

### Claim 12 (depends on 10)

The condensed cyclic compound of claim 10, wherein
CY4 and CY5 are each independently selected from a benzene group, a naphthalene group, a fluorene group, a carbazole group, a dibenzofuran group, and a dibenzothiophene group.

### Claim 13 (depends on 10)

The condensed cyclic compound of claim 10, wherein
the condensed cyclic compound is represented by one of Formulae 1-1 to 1-3:
in Formulae 1-1 to 1-3,
Ar1 and Ar2 are the same as in claim 10,
R41 to R48 are each independently the same as R40 in claim 10, and
R51 to R54 are each independently the same as R50 in claim 10.

### Claim 14 (depends on 10)

The condensed cyclic compound of claim 10 being selected from Compounds 33 to 44, 57 to 73, 80-85, 90, or 103 to 108: