# US 2019/0375773 A1 · Heterocyclic compound and organic light-emitting device including the same

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- Number: US 2019/0375773 A1
- Document ID: US20190375773A1
- Status: Published application
- Kind: A1
- Application number: 16/435,892
- Filed: 2019-06-10
- Published: 2019-12-12
- Earliest claimed: 2018-06-12
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Mieun JUN; Soobyung KO; Heechoon AHN; Youngkook KIM; Seokhwan HWANG
- Web page: https://patentgrep.com/patent/US20190375773A1

## CPC

- C07F 9/6571: having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F 9/6596: having atoms other than oxygen, sulfur, selenium, tellurium, nitrogen or phosphorus as ring hetero atoms
- C07F 9/6568: having phosphorus atoms as the only ring hetero atoms
- C07F 9/65685: {the ring phosphorus atom being part of a phosphine oxide or thioxide}
- C07F 9/6578: having phosphorus and sulfur atoms with or without oxygen atoms, as ring hetero atoms
- C07F 9/6584: having one phosphorus atom as ring hetero atom
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 2101/10: Triplet emission
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A heterocyclic compound represented by Formula 1: wherein A1 in Formula 1 is selected from groups represented by Formulae 1-1 to 1-7, and an organic light-emitting device including the same.

## Claims

### Claim 1

A heterocyclic compound represented by Formula 1:
wherein A1 in Formula 1 is selected from groups represented by Formulae 1-1 to 1-7:
wherein X1 in Formula 1-1 to 1-7 is selected from O, S, SO2, N(R12), C(R13)(R14), Si(R15)(R16), Se, Ge(R17)(R18), and Sn(R19)(R20),
X2 in Formulae 1-1 to 1-7 is selected from O, S, N(R21), C(R22)(R23), and Si(R24)(R25),
R1 to R25 in Formulae 1 and 1-1 to 1-7 are each independently selected from a group represented by Formula 2-1, a group represented by Formula 2-2, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 C6-C60 aryloxy group, and a substituted or unsubstituted C6-C60 arylthio group,
A11, L1, and L2 in Formulae 2-1 and 2-2 are each independently selected from a C5-C60 carbocyclic group and a C2-C60 heterocyclic group,
A12 in Formula 2-2 is a C2-C60 heterocyclic group,
a1 and a2 in Formulae 2-2 and 2-2 are each independently an integer from 0 to 5, wherein, when a1 is two or more, two or more L1(s) are identical to or different from each other, and when a2 is two or more, two or more L2(s) are identical to or different from each other,
R31 and R32 in Formulae 2-1 and 2-2 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), and —P(═O)(Q1)(Q2),
b1, b2, c1, and c2 in Formulae 2-1 and 2-2 are each independently an integer from 0 to 5, wherein, when b1 is two or more, two or more R31(s) are identical to or different from each other, when b2 is two or more, two or more R32(s) are identical to or different from each other, when c1 is two or more, two or more *-[(L1)a1-(R31)b1](s) are identical to or different from each other, and when c2 is two or more, two or more *-[(L2)a2-(R32)b2](s) are identical to or different from each other,
i) when A1 in Formula 1 is a group represented by Formula 1-1, at least one of R2, R3, R5, R6, R8, and R9 in Formula 1 is selected from a group represented by Formula 2-1 and a group represented by Formula 2-2,
ii) when A1 in Formula 1 is a group represented by Formula 1-1 and R2, R3, R5, R6, R7, R8, and R9 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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, and a substituted or unsubstituted C1-C60 alkoxy group, R4 in Formula 1 is a group represented by Formula 2-1, or
iii) when A1 in Formula 1 is a group represented by Formula 1-1 and R2, R3, R5, R6, R8, and R9 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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, and a substituted or unsubstituted C1-C60 alkoxy group, R4 and R7 in Formula 1 are each independently a group represented by Formula 2-1,
at least one substituent of the substituted C5-C60 carbocyclic group, the substituted C2-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),
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 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, and
* indicates a binding site to a neighboring atom.

### Claim 2 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein
X1 is selected from O, S, N(R12), and C(R13)(R14).

### Claim 3 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein
R1 is selected from:
hydrogen, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, and a phenanthrenyl group; and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, and a phenanthrenyl 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 hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, and a phenanthrenyl group.

### Claim 4 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein
A11, L1, and L2 are each independently selected from:
a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a naphthyridine group, a quinoxaline group, a quinazoline group, a carbazole group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a triazine group, a dibenzofuran group, a dibenzothiophene group, and a biphenyl group; and
a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a naphthyridine group, a quinoxaline group, a quinazoline group, a carbazole group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a triazine group, a dibenzofuran group, a dibenzothiophene group, and a biphenyl 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 methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, ter-butyl group, a pentyl group, an isoamyl group, a hexyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a Spiro-fluorene-benzofluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyridinyl group, a pyrimidyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a biphenylyl group.

### Claim 5 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein
A12 is selected from:
a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a naphthyridine group, a quinoxaline group, a quinazoline group, a carbazole group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a triazine group, a dibenzofuran group, and a dibenzothiophene group; and
a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a naphthyridine group, a quinoxaline group, a quinazoline group, a carbazole group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a triazine group, a dibenzofuran group, and a dibenzothiophene 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 methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, ter-butyl group, a pentyl group, an isoamyl group, a hexyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-fluorene-benzofluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyridinyl group, a pyrimidyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a biphenylyl group.

### Claim 6 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein
R31 and R32 are each independently selected from groups represented by Formulae 5-1 to 5-28:
wherein, in Formulae 5-1 to 5-28,
Y31 is O, S, C(Z35)(Z36), N(Z35), or Si(Z35)(Z36),
Z31 to Z36 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-C20 alkyl group, a C1-C20 alkenyl group, a C1-C20 alkynyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenanthrenyl group, an anthracenyl group, a triperylenyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, and a triazinyl group,
e2 is 1 or 2,
e3 is an integer from 1 to 3,
e4 is an integer from 1 to 4,
e5 is an integer from 1 to 5,
e6 is an integer from 1 to 6,
e7 is an integer from 1 to 7, and
* indicates a binding site to a neighboring atom.

### Claim 7 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein
the group represented by Formula 2-1 is selected from groups represented by Formulae 2-1-(1) to 2-1-(17):
wherein, in the above structures, * indicates a binding site to a neighboring atom.

### Claim 8 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein
the group represented by Formula 2-2 is selected from groups represented by Formulae 2-2-(1) and 2-2-(2):
wherein, in the above structures, * indicates a binding site to a neighboring atom.

### Claim 9 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein
the heterocyclic compound is represented by Formula 11,
wherein, in Formula 11,
at least one of R3 and R8 is selected from a group represented by Formula 2-1 and a group represented by Formula 2-2, and
X1, R1, R2, R4 to R7, and R9 are each independently the same as described in claim 1.

### Claim 10 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein
the heterocyclic compound is represented by Formula 11,
wherein, in Formula 11,
X1 and R1 are each independently the same as described in claim 1, and
R2, R3, R5, R6, R7, R8, and R9 are each independently hydrogen, deuterium, a cyano group, a C1-C10 alkyl group, or a C1-C10 alkoxy group, and R4 is a group represented by Formula 2-1, or
R2, R3, R5, R6, R8, and R9 are each independently hydrogen, deuterium, a cyano group, a C1-C10 alkyl group, or a C1-C10 alkoxy group, and R4 and R7 are each independently a group represented by Formula 2-1.

### Claim 11 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein
i) A1 in Formula 1 is selected from groups represented by Formulae 1-2 to 1-7, X2 in Formulae 1-2 to 1-7 is N(R21), and at least one of R2 to R11 and R21 is selected from a group represented by Formula 2-1 and a group represented by Formula 2-2, or
ii) A1 in Formula 1 is selected from groups represented by Formulae 1-2 to 1-7, X2 in Formulae 1-2 to 1-7 is selected from O, S, C(R22)(R23), and Si(R24)(R25), and at least one of R2 to R11 is selected from a group represented by Formula 2-1 and a group represented by Formula 2-2.

### Claim 12 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein
i) A1 in Formula 1 is selected from groups represented by Formulae 1-2 to 1-7, X2 in Formulae 1-2 to 1-7 is N(R21), and at least one of R3, R4, R7, R8, and R21 is selected from a group represented by Formula 2-1 and a group represented by Formula 2-2, or
ii) A1 in Formula 1 is selected from groups represented by Formulae 1-2 to 1-7, X2 in Formulae 1-2 to 1-7 is selected from O, S, C(R22)(R23), and Si(R24)(R25), and at least one of R3, R4, R7, and R8 is selected from a group represented by Formula 2-1 and a group represented by Formula 2-2.

### Claim 13 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein
the heterocyclic compound is represented by Formula 12 or 13:
wherein, in Formulae 12 and 13,
X1, X2, and R1 to R11 are each independently the same as described in claim 1.

### Claim 14 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein
the compound represented by Formula 1 is selected from Compounds 1 to 285:

### Claim 15 (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 and including an emission layer,
wherein the organic layer includes at least one of the heterocyclic compound of claim 1.

### Claim 16 (depends on 15)

The organic light-emitting device as claimed in claim 15, wherein
the first electrode is an anode,
the second electrode is a cathode,
the organic layer further includes 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 includes at least one selected from a hole injection layer, a hole transport layer, a buffer layer, an emission auxiliary layer, and an electron blocking layer, and
the electron transport region includes a hole blocking layer, an electron transport layer, and an electron injection layer.

### Claim 17 (depends on 16)

The organic light-emitting device as claimed in claim 16, wherein
the emission layer includes the heterocyclic compound.

### Claim 18 (depends on 16)

The organic light-emitting device as claimed in claim 16, wherein
the emission layer includes a host and a dopant, and
the host or the dopant includes the heterocyclic compound.

### Claim 19 (depends on 18)

The organic light-emitting device as claimed in claim 18, wherein
the host includes the heterocyclic compound, and
the dopant includes a phosphorescent dopant.

### Claim 20 (depends on 18)

The organic light-emitting device as claimed in claim 18, wherein
the dopant includes the heterocyclic compound, and
the host includes at least one selected from an anthracene-based compound, a pyrene-based compound, a spiro-bifluorene-based compound, and a phosphine oxide-based compound.