# US 11,444,247 B2 · Compound and organic light-emitting device including the same

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- Number: US 11,444,247 B2
- Document ID: US11444247B2
- Status: Granted
- Kind: B2
- Application number: 16/865,119
- Filed: 2020-05-01
- Published: 2021-04-08
- Granted: 2022-09-13
- Earliest claimed: 2019-10-08
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Minji Kim; Dongjun Kim; Eunjae Jeong; Sohee Jo; Sanghyun Han
- Web page: https://patentgrep.com/patent/US11444247B2

## CPC

- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 209/88: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- H10K 71/00: Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/115: comprising active inorganic nanostructures, e.g. luminescent quantum dots
- H10K 50/15: Hole transporting layers
- H10K 50/171: {Electron injection layers}
- H10K 59/123: Connection of the pixel electrodes to the thin film transistors [TFT]
- H10K 71/164: {using vacuum deposition}
- 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 2102/351: {Thickness}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A compound is represented by Formula 1, where the substituents are as defined in the detailed description. An organic light-emitting device including the compound has high efficiency and improved lifespan compared to an organic light-emitting device including a compound of the related art.

## Claims

### Claim 1

A compound represented by Formula 1 below:
wherein, in Formula 1,
Ar1 to Ar3 and R1 to R4 are each independently selected from hydrogen, 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 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), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
l to n are each independently an integer from 1 to 4,
o is an integer from 1 to 3,
at least one substituent of 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), —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), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and
—Si(Q31)(Q32)(Q33), —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 compound of claim 1, wherein R1 to R4 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group, and a monovalent non-aromatic condensed polycyclic group.

### Claim 3 (depends on 1)

The compound of claim 1, wherein Ar1 and Ar2 are each independently selected from Formulae 2a to 2c below:
wherein in Formulae 2a to 2c,
H1 is O, S, CR11R12, or NR13,
Z1 to Z4 and R11 to R13 are each independently selected from hydrogen, 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, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triazinyl group, a benzimidazolyl group, and a phenanthrolinyl group, wherein R11 and R12 are optionally linked to each other to form a ring,
a1 is an integer from 1 to 5,
a2 is an integer from 1 to 7,
3a and a4 are each independently an integer from 1 to 3, and
* indicates a binding site to a neighboring atom.

### Claim 4 (depends on 1)

The compound of claim 1, wherein Ar3 is selected from Formulae 3a and 3b below:
wherein in Formulae 3a and 3b,
Z4 and Z5 are each independently selected from hydrogen, 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, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triazinyl group, a benzimidazolyl group, and a phenanthrolinyl group,
a4 is an integer from 1 to 5,
a5 is an integer from 1 to 7, and
* indicates a binding site to a neighboring atom.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the compound represented by Formula 1 is represented by Formula 2 below:
wherein, in Formula 2, Ar1 to Ar3, R1 to R4, and l to o are each the same as respectively described in connection with Formula 1.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the compound represented by Formula 1 is represented by Formula 3 below:
wherein, in Formula 3, Ar1 to Ar3, R1 to R4, and l to o are each the same as respectively described in connection with Formula 1.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the compound represented by Formula 1 is represented by Formula 4 below:
wherein, in Formula 4, Ar1 to Ar3, R1 to R4, and l to o are each the same as respectively described in connection with Formula 1.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the compound represented by Formula 1 is represented by Formula 5 below:
wherein, in Formula 5, Ar1 to Ar3, R1 to R4, and l to o are each the same as respectively described in connection with Formula 1.

### Claim 9 (depends on 8)

The compound of claim 8, wherein R1 to R4 are each independently hydrogen or deuterium.

### Claim 10 (depends on 1)

The compound of claim 1, wherein the compound represented by Formula 1 is selected from compounds below:

### Claim 11 (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 comprising an emission layer,
wherein, the organic layer comprises the compound of claim 1.

### Claim 12 (depends on 11)

The organic light-emitting device of claim 11, wherein
the first electrode is an anode,
the second electrode is a cathode, and
the organic layer comprises:
i) a hole transport region between the first electrode and the emission layer and comprising a hole injection layer, a hole transport layer, an emission auxiliary layer, and/or an electron blocking layer, and
ii) an electron transport region between the emission layer and the second electrode and comprising a hole blocking layer, an electron transport layer, and/or an electron injection layer.

### Claim 13 (depends on 12)

The organic light-emitting device of claim 12, wherein the hole transport region comprises the compound.

### Claim 14 (depends on 11)

The organic light-emitting device of claim 11, wherein the emission layer is a blue emission layer.

### Claim 15 (depends on 11)

The organic light-emitting device of claim 11, wherein the emission layer is a fluorescent emission layer.

### Claim 16 (depends on 12)

The organic light-emitting device of claim 12, wherein the electron transport region comprises a metal-containing material.

### Claim 17 (depends on 12)

The organic light-emitting device of claim 12, wherein the electron injection layer comprises an alkali metal halide.

### Claim 18 (depends on 11)

The organic light-emitting device of claim 11, wherein:
the emission layer comprises a fluorescent dopant, and
the fluorescent dopant comprises an arylamine compound or a styrylamine compound.

### Claim 19 (depends on 11)

The organic light-emitting device of claim 11, wherein the emission layer comprises a quantum dot.

### Claim 20 (depends on 11)

An electronic apparatus comprising:
a thin-film transistor, and
the organic light-emitting device of claim 11,
wherein,
the thin-film transistor comprises a source electrode, a drain electrode, an activation layer, and a gate electrode, and
the first electrode of the organic light-emitting device is electrically connected to the source electrode or the drain electrode of the thin-film transistor.

### Claim 21 (depends on 5)

The compound of claim 5, wherein R1 to R4 are each independently hydrogen or deuterium.

### Claim 22 (depends on 6)

The compound of claim 6, wherein R1 to R4 are each independently hydrogen or deuterium.

### Claim 23 (depends on 7)

The compound of claim 7, wherein R1 to R4 are each independently hydrogen or deuterium.