# US 10,873,041 B2 · Condensed cyclic compound and organic light-emitting device including the same

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- Number: US 10,873,041 B2
- Document ID: US10873041B2
- Status: Granted
- Kind: B2
- Application number: 16/121,365
- Filed: 2018-09-04
- Published: 2019-06-06
- Granted: 2020-12-22
- Earliest claimed: 2017-12-06
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Seulong Kim; Daeyup Shin
- Web page: https://patentgrep.com/patent/US10873041B2

## CPC

- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- C09K 11/06: containing organic luminescent materials
- 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 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1018: Heterocyclic compounds
- C09K 2211/1022: bridged by heteroatoms, e.g. N, P, Si or B
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/10: Triplet emission
- H10K 2101/20: Delayed fluorescence emission
- H10K 2101/30: Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A condensed cyclic compound that emits high-efficiency delayed fluorescence is provided. The compound may be represented by Formula 1, in which A is a moiety represented by Formula 1-1. In Formula 1-1, X1 may be a carbon or silicon atom linked to B1 and B2, and X2 may be a carbon or silicon atom linked to B3 and B4. When the compound represented by Formula 1 satisfies ES1<2ET1<ET2 (wherein ES1 is the first singlet energy level, ET1 is the first triplet energy level, and ET2 is the second triplet energy level of the condensed cyclic compound), an energy transition to a second triplet state may be disfavored during up-conversion of the condensed cyclic compound from a triplet state to a singlet state through interaction with an adjacent molecule in a triplet energy state.

## Claims

### Claim 1

A condensed cyclic compound represented by Formula 1:
Formula 1
wherein, in Formula 1,
A is a moiety represented by Formula 1-1, and
B1 to B4 are each independently 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, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group:
wherein, in Formula 1-1,
X1 is a carbon atom (C) linked to B1 and B2 or a silicon atom (Si) linked to B1 and B2,
X2 is a carbon atom linked to B3 and B4 or a silicon atom linked to B3 and B4,
X3 iS O or S,
Al and A2 are each independently a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group,
L1 and L2 are each independently a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
a1 and a2 are each independently an integer from 0 to 5,
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),
b1 and b2 are each independently an integer from 1 to 10,
c1 and c2 are each independently 1, 2, 3, or 4,
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), and
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.

### Claim 2 (depends on 1)

The condensed cyclic compound of claim 1, wherein:
X1 is a carbon atom linked to B1 and B2, and X2 is a carbon atom linked to B3 and B4; or
X1 is a silicon atom linked to B1 and B2, and X2 is a silicon atom linked to B3 and B4.

### Claim 3 (depends on 1)

The condensed cyclic compound of claim 1, wherein A1 and A2 are each a benzene group.

### Claim 4 (depends on 1)

The condensed cyclic compound of claim 1, wherein B1 to B4 are each independently selected from 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, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

### Claim 5 (depends on 1)

The condensed cyclic compound of claim 1, wherein:
B1 to B4 are each independently selected from:
a phenyl group and a pyridinyl group; and
a phenyl group and a pyridinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a pentyl group, an isoamyl group, a hexyl group, a phenyl group, and —Si(Q31)(Q32)(Q32).

### Claim 6 (depends on 1)

The condensed cyclic compound of claim 1, wherein:
B1 to B4 in Formula 1 are each independently selected from:
a phenyl group, and a pyridinyl group; and
a phenyl group and a pyridinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a pentyl group, an isoamyl group, a hexyl group, a phenyl group, and —Si(Q31)(Q32)(Q32), and
R1 and R2 in Formula 1-1 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a pentyl group, an isoamyl group, a hexyl group, a phenyl group, a biphenyl group, and a pyridinyl group.

### Claim 7 (depends on 1)

The condensed cyclic compound of claim 1, wherein:
B1 to B4 in Formula 1 are each independently selected from:
a phenyl group, and a pyridinyl group; and
a phenyl group and a pyridinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a pentyl group, an isoamyl group, a hexyl group, a phenyl group, and —Si(Q31)(Q32)(Q32), and
A1 and A2 in Formula 1-1 are each a benzene group.

### Claim 8 (depends on 1)

The condensed cyclic compound of claim 1, wherein,
in Formula 1,
a dihedral angle between a plane P1 including A and a plane P2 including Bn is 60° or more, and
n is 1, 2, 3, or 4.

### Claim 9 (depends on 1)

The condensed cyclic compound of claim 1, wherein:
the condensed cyclic compound satisfies Equation 1:
ES1<2ET1<ET2, Equation 1
wherein, in Equation 1,
ES1 is the first singlet energy level of the condensed cyclic compound,
ET1 is the first triplet energy level of the condensed cyclic compound, and
ET2 is the second triplet energy level of the condensed cyclic compound.

### Claim 10 (depends on 9)

The condensed cyclic compound of claim 9, wherein ES1 is about 2.7 eV to about 3.0 eV.

### Claim 11 (depends on 9)

The condensed cyclic compound of claim 9, wherein ET2 is about 2.8 eV to about 3.4 eV.

### Claim 12 (depends on 1)

The condensed cyclic compound of claim 1, wherein the condensed cyclic compound satisfies Equation 2:
2EAT1<EBT1, Equation 2
wherein, in Equation 2,
EAT1 is the first triplet energy level of A,
EBT1 is the first triplet energy level of Bn, and n is 1, 2, 3, or 4.

### Claim 13 (depends on 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,
wherein the organic layer comprises an emission layer and at least one of the condensed cyclic compound of claim 1.

### Claim 14 (depends on 13)

The organic light-emitting device of claim 13, 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,
the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and
the electron transport region comprises a buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

### Claim 15 (depends on 13)

The organic light-emitting device of claim 13, wherein the emission layer comprises the condensed cyclic compound.

### Claim 16 (depends on 15)

The organic light-emitting device of claim 15, wherein:
the emission layer further comprises a host, and
an amount of the host in the emission layer is larger than an amount of the condensed cyclic compound.

### Claim 17 (depends on 16)

The organic light-emitting device of claim 16, wherein the condensed cyclic compound is provided to emit delayed fluorescence.

### Claim 18 (depends on 16)

The organic light-emitting device of claim 16, wherein an amount of the condensed cyclic compound in the emission layer is about 0.01 parts by weight to about 30 parts by weight based on 100 parts by weight of the host.

### Claim 19 (depends on 16)

The organic light-emitting device of claim 16, wherein:
the host comprises a compound represented by Formula 301:
[Ar301]xb11—[(L301)xb1—R301]xb21, Formula 301
wherein, in Formula 301,
Ar301 is a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
xb11 is 1, 2, or 3,
L301 is selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
xb1 is an integer from 0 to 5,
R301 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 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(Q301)(Q302)(Q303), —N(Q301)(Q302), —B(Q301)(Q302), —C(═O)(Q301), —S(═O)2(Q301), and —P(═O)(Q301)(Q302),
xb21 is an integer from 1 to 5, and
Q301 to Q303 are each independently selected from a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

### Claim 20 (depends on 13)

The organic light-emitting device of claim 13, wherein the emission layer comprises the condensed cyclic compound, and light having a maximum emission wavelength of about 420 nm to about 470 nm is emitted from the emission layer.