# US 12,193,320 B2 · Heterocyclic compound, light-emitting device including heterocyclic compound, and electronic apparatus including light-emitting device

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- Number: US 12,193,320 B2
- Document ID: US12193320B2
- Status: Granted
- Kind: B2
- Application number: 17/323,817
- Filed: 2021-05-18
- Published: 2021-12-02
- Granted: 2025-01-07
- Earliest claimed: 2020-05-19
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Heechoon Ahn; Soobyung Ko; Hyeongmin Kim; Hyunah Um; Yeseul Lee; Yirang Im
- Web page: https://patentgrep.com/patent/US12193320B2

## CPC

- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- C07F 7/0812: {comprising a heterocyclic ring}
- C09K 11/06: containing organic luminescent materials
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/342: {comprising iridium}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 2101/10: Triplet emission
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

A heterocyclic compound represented by Formula 1: wherein, in Formula 1, Ar1 to Ar4, Ar11, and Ar12 are each, independently from one another, as defined herein.

## Claims

### Claim 1

A heterocyclic compound represented by Formula 1:
wherein, a group represented by
in Formula 1 is a group represented by one of Formulae 7-2 to 7-13:
wherein, in Formulae 7-2 to 7-13, Ar4, R4, and a4 have, independently from one another, the same meanings as described hereinafter, a43 is an integer from 0 to 3, * indicates a binding site to an adjacent silicon atom in Formula 1, and *′ indicates a binding site to L1 in Formula 1,
Ar1 to Ar4, and Ar12 in Formula are each, independently from one another, a group represented by Formula 2 or a group represented by Formula 3, and Ar11 in Formula 1 is a group represented by Formula 2,
d1, d2, and d3 in Formula 1 are each, independently from one another, an integer from 0 to 5;
d11 in Formula 1 1;
d12 in Formula 1 is 0 or 1;
L1 in Formula 1 is a single bond or a group represented by Formula 4;
L11 in Formulae 2 and 3 is a single bond, a group represented by Formula 4, or a group represented by Formula 5
b1 and b11 in Formulae 1 to 3 are each, independently from one another, an integer from 1 to 5;
X1 in Formula 1 is a single bond, O, S, C(Z3)(Z4), or Si(Z3)(Z4);
X11 in Formulae 2 and 3 is a single bond, O, S, C(Z13)(Z14), or Si(Z13)(Z14);
X21 in Formula 4 is a single bond, O, S, C(Z23)(Z24), or Si(Z23)(Z24);
R1 to R4 in Formula 1 are each, independently from one another:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, or a C1-C20 alkoxy group;
a C1-C20 alkyl group or a C1-C20 alkoxy group, each, independently from one another, substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10 alkylphenyl group, a fluorenyl group, a carbazolyl group, or a dibenzosilolyl group, each, independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10 alkylphenyl group, a fluorenyl group, a carbazolyl group, a dibenzosilolyl group, or any combination thereof; or
—Si(Q1)(Q2)(Q3),
Z1 to Z4, Z11 to Z15, and Z21 to Z25 in Formulae 1 to 5 are each, independently from one another, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2);
a1 to a3 in Formula 1 are each, independently from one another, an integer from 0 to 5;
a4, c1, c11, c13, c21, and c25 in Formulae 1 to 5 are each, independently from one another, an integer from 0 to 4;
c2, c12, and c22 in Formulae 1, 3, and 4 are each, independently from one another, an integer from 0 to 3;
* in Formulae 2 and 4 indicates a binding site to an adjacent carbon atom, and * and *′ in Formulae 3 to 5 each indicate a binding site to an adjacent atom; and
R10a is:
-D, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12),
—C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C1-C60 arylthio group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21),
—S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof; or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each, independently from one another, hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; or a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each independently from one another, unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

### Claim 2 (depends on 1)

The heterocyclic compound of claim 1, wherein d1, d2, and d3 in Formula 1 are each 0.

### Claim 3 (depends on 1)

The heterocyclic compound of claim 1, wherein d1, d2, and d3 in Formula 1 are each, independently from one another, 0 or 1, and the sum of d1, d2, and d3 is 1 or 2.

### Claim 4 (depends on 1)

The heterocyclic compound of claim 1, wherein Z1 to Z4, Z11 to Z15, and Z21 to Z25 in Formulae 1 to 5 are each, independently from one another:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, or a C1-C20 alkoxy group;
a C1-C20 alkyl group or a C1-C20 alkoxy group, each, independently from one another, substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10 alkylphenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a dibenzosilolyl group, each, independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10 alkylphenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, or any combination thereof; or
—Si(Q1)(Q2)(Q3) wherein Q1, Q2, and Q3 have, independently from one another, the same meanings as in claim 1.

### Claim 5 (depends on 1)

The heterocyclic compound of claim 1, wherein a group represented by
in Formula 1 is a group represented by one of Formulae 6-1 to 6-14:
wherein, in Formulae 6-1 to 6-14, Ar11, Ar12, X1, Z1, Z2, c1, and c2 have, independently from one another, the same meanings as in claim 1, c13 is an integer from 0 to 3, and * indicates a binding site to L1 in Formula 1.

### Claim 6 (depends on 1)

The heterocyclic compound of claim 1, wherein a group represented by
in Formula 1 is a group represented by one of Formulae 8-1 to 8-4:
wherein, in Formulae 8-1 to 8-4, Ar2, R2, and a2 have, independently from one another, the same meanings as in claim 1, a24 is an integer from 0 to 4, and * indicates a binding site to an adjacent silicon atom in Formula 1.

### Claim 7 (depends on 1)

The heterocyclic compound of claim 1, wherein a group represented by Formula 4 comprises one or more groups represented by Formulae 4-1 to 4-4:
wherein, in Formulae 4-1 to 4-4, X21, Z21, Z22, c21, and c22 have, independently from one another, the same meanings as in claim 1, * indicates a binding site to an adjacent carbon atom, and *′ indicates a binding site to an adjacent atom.

### Claim 8 (depends on 1)

The heterocyclic compound of claim 1, wherein a group represented by Formula 5 comprises one or more groups represented by Formulae 5-1 to 5-3:
wherein in Formulae 5-1 to 5-3, Z26 to Z29 have, independently from one another, the same meanings as Z25 as in claim 1, and * and *′ each indicate a binding site to an adjacent atom.

### Claim 9

A heterocyclic compound selected from one of Compounds 1, 3 to 39 and 42 to 62:

### Claim 10 (depends on 1)

A light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
an interlayer disposed between the first electrode and the second electrode and comprising an emission layer; and the heterocyclic compound of claim 1.

### Claim 11 (depends on 10)

The light-emitting device of claim 10, wherein the emission layer in the interlayer comprises the heterocyclic compound.

### Claim 12 (depends on 11)

The light-emitting device of claim 11, wherein the emission layer comprises a dopant and a host, and the host comprises the heterocyclic compound.

### Claim 13 (depends on 12)

The light-emitting device of claim 12, wherein the dopant is configured to emit a blue light.

### Claim 14 (depends on 12)

The light-emitting device of claim 12, wherein
the dopant comprises a transition metal and a ligand(s) in a number represented by m;
m is an integer from 1 to 6;
the ligands in number of m are identical to or different from one another;
at least one of the ligands is bound to the transition metal via a carbon-transition metal bond; and
the carbon-transition metal bond is a coordinate bond.

### Claim 15 (depends on 10)

An electronic apparatus comprises the light-emitting device of claim 10.

### Claim 16 (depends on 15)

The electronic apparatus of claim 15, further comprising a thin-film transistor, wherein the thin-film transistor comprises a source electrode and a drain electrode, and the first electrode of the light-emitting device is electrically connected to at least one of the source electrode and the drain electrode of the thin-film transistor.