# US 10,121,974 B2 · Condensed-cyclic compound and organic light-emitting device comprising the same

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- Number: US 10,121,974 B2
- Document ID: US10121974B2
- Status: Granted
- Kind: B2
- Application number: 14/743,217
- Filed: 2015-06-18
- Published: 2016-06-30
- Granted: 2018-11-06
- Earliest claimed: 2014-12-31
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Mieun Jun; Sooyon Kim; Youngkook Kim; Seokhwan Hwang; Seunggak Yang
- Web page: https://patentgrep.com/patent/US10121974B2

## CPC

- C07F 5/027: {Organoboranes and organoborohydrides}
- C07F 7/0803: {Compounds with Si-C or Si-Si linkages}
- C07F 7/081: {comprising at least one atom selected from the elements N, O, halogen, S, Se or Te}
- C09K 11/06: containing organic luminescent materials
- H10K 85/361: {Polynuclear complexes, i.e. complexes comprising two or more metal centers}
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- 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}
- H10K 85/658: {Organoboranes}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1088: containing oxygen as the only heteroatom
- C09K 2211/1092: containing sulfur as the only heteroatom
- C09K 2211/1096: containing other heteroatoms
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting 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 is represented by Formula 1: where X, L1 to L3, R1 to R3, Ar1 to Ar6, c1 to c3, a1 to a2, and b1 to b3 are as defined in the specification.

## Claims

### Claim 1

A condensed-cyclic compound represented by one of Formula 1, 1B, and 1C:
wherein, in Formula 1, X is selected from O, S, and N(R11);
when X is O, A is selected from a naphthalene, an anthracene, a phenanthrene, a chrysene, and a pyrene, and ii) when X is S or N(R11), A is selected from a benzene, a naphthalene, an anthracene, a phenanthrene, a chrysene, and a pyrene;
in Formulae 1B and 1C,
X is selected from O, S, N(R11), Si(R12)(R13) and C(R15)(R16);
in Formula 1, 1B, and 1C
L1 to L3 are each independently selected from:
a phenylene group, and
a phenylene group substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, 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
a1 to a3 are each independently selected from 0 and 1;
Ar1 to Ar6 are each independently selected from a group represented by one of Formulae 6-1 to 6-28:
wherein, in Formulae 6-1 to 6-28, * indicates a binding site to an adjacent atom;
c1 to c3 are each independently selected from 0 and 1, provided that a sum of c1, c2, and c3 is 1 or more;
R1 to R3 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a methyl group and a phenyl group
b1 to b3 are each independently an integer selected from 0 to 3;
R11, R12, R13, R15, and R16 are each independently selected from a methyl group and a phenyl group;
and
B is a boron atom.

### Claim 2 (depends on 1)

The condensed-cyclic compound as claimed in claim 1, wherein
L1 to L3 are each independently selected from a group represented by one of Formulae 3-1 to 3-3:
wherein, in Formulae 3-1 to 3-3,
Z1 is selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, and a phenyl group
d1 is an integer selected from 1 to 4;
and
* and *′ each indicate a binding site to an adjacent atom.

### Claim 3 (depends on 1)

The condensed-cyclic compound as claimed in claim 1, wherein
L1 to L3 are each independently selected from a group represented by one of Formulae 4-1, 4-3, 4-8, 4-10, 4-17, 4-24, 4-26, and 4-28:
wherein, in Formulae 4-1, 4-3, 4-8, 4-10, 4-17, 4-24, 4-26, and 4-28, *and *′ each indicate a binding site to an adjacent atom.

### Claim 4 (depends on 1)

The condensed-cyclic compound as claimed in claim 1, wherein a sum of c1, c2, and c3 is selected from 1 and 2.

### Claim 5 (depends on 1)

The condensed-cyclic compound as claimed in claim 1, wherein the condensed-cyclic compound is represented by one of Formulae 1A to 1C:
wherein,
in Formulae 1A, X is selected from S and N(R11),
in Formulae 1B and 1C, X is selected from O, S, N(R11), Si(R12)(R13), and C(R15)(R16), and L1 to L3, a1 to a3, Ar1 to Ar6, c1 to c3, R1 to R3, b1 to b3 and R11, R12, R13, R15, and R16 are the same as defined in claim 1.

### Claim 6 (depends on 1)

The condensed-cyclic compound as claimed in claim 1, wherein
the condensed-cyclic compound is represented by one of Formulae 1-1 to 1-3 and Formulae 2-1 to 2-3:
wherein,
in Formulae 1-1 and 2-1, X is selected from S and N(R11),
in Formulae 1-2, 1-3, 2-2 and 2-3, X is selected from O, S, N(R11), Si(R12)(R13), and C(R15)(R16),
and
in Formulae 1-1 to 1-3 and Formulae 2-1 to 2-3, L1, L2, a1, a2, Ar1 to Ar4, R1 to R3, b1 to b3, R11, R12, R13, R15, and R16 are the same as defined in claim 1.

### Claim 7 (depends on 1)

The condensed-cyclic compound as claimed in claim 1, wherein
the condensed-cyclic compound is represented by one selected from Formulae 1-1(1) to 1-3(1) and Formulae 2-1(1) to 2-3(1):
wherein,
in Formulae 1-1(1) and 2-1(1), X is selected from S and N(R11),
in Formulae 1-2(1), 1-3(1), 2-2(1) and 2-3(1), X is selected from O, S, N(R11), Si(R12)(R13), and C(R15)(R16),
in Formulae 1-1(1) to 1-3(1) and Formulae 2-1(1) to 2-3(1), L1, L2, a1, a2, Ar1 to Ar4 and R11, R12, R13, R15, and R16 are the same as defined in claim 1, and R1a to R1f, R2a to R2c, and R3a to R3c are the same as defined in connection with R1 as described in claim 1.

### Claim 8 (depends on 7)

The condensed-cyclic compound as claimed in claim 7, wherein
Ar1 to Ar4 are each independently selected from Formulae 6-1 to 6-28, and
R1a to R1f, R2a to R2c, and R3a to R3c are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a methyl group, and a group represented by Formula 6-1:
wherein, in Formulae 6-1 to 6-28, * indicates a binding site to an adjacent atom.

### Claim 9 (depends on 1)

The condensed-cyclic compound as claimed in claim 1, wherein the condensed-cyclic compound is represented by one of Compounds 14 to 26, 40 to 169 and 182 to 231:

### Claim 10 (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, the organic layer including an emission layer, wherein the organic layer includes the condensed-cyclic compound represented by Formula 1 as claimed in claim 1.

### Claim 11 (depends on 10)

The organic light-emitting device as claimed in claim 10, wherein
the first electrode is an anode,
the second electrode is a cathode,
and the organic layer includes i) a hole transport region between the first electrode and the emission layer, the hole transport region including at least one selected from a hole injection layer, a hole transport layer, a buffer layer, and an electron blocking layer and ii) an electron transport region between the emission layer and the second electrode, the electron transport region including at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer,
wherein at least one selected from the hole transport region and the emission layer includes the condensed-cyclic compound represented by Formula 1.

### Claim 12 (depends on 10)

The organic light-emitting device as claimed in claim 10, wherein the emission layer further includes a host.