# US 10,319,919 B2 · Compound and organic light-emitting device including the same

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- Number: US 10,319,919 B2
- Document ID: US10319919B2
- Status: Granted
- Kind: B2
- Application number: 15/177,312
- Filed: 2016-06-08
- Published: 2017-04-20
- Granted: 2019-06-11
- Earliest claimed: 2015-10-15
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Eunyoung Lee; Youngkook Kim; Junha Park; Munki Sim; Hyoyoung Lee; Eunjae Jeong; Seokhwan Hwang
- Web page: https://patentgrep.com/patent/US10319919B2

## CPC

- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C07D 471/04: Ortho-condensed systems
- C07F 9/5325: {Aromatic phosphine oxides or thioxides (P-C aromatic linkage)}
- C07F 9/6561: containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- H10K 59/123: Connection of the pixel electrodes to the thin film transistors [TFT]
- H10K 85/30: Coordination compounds
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 50/155: comprising dopants
- H10K 50/16: Electron transporting layers
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

An organic light-emitting device includes: 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 comprises a compound represented by Formula 1. An organic light-emitting device including the compound may have high efficiency, low voltage, high luminance, and a long lifespan.

## Claims

### Claim 1

A compound represented by Formula 1:
wherein, in Formula 1,
A1 to A8 are each independently selected from CR11, CR12, CR13, CR14, CR15, CR16, CR17, CR18, and N, wherein at least one selected from A1 to A8 is N;
R1 is selected from deuterium, a halogen group, a nitro group, a cyano 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 C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-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, P(═O)R31R32, P(═S)R33R34, S(═O)2R35, and S(═O)R36;
R2 is selected from hydrogen, deuterium, a halogen group, a nitro group, a cyano 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 C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-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, P(═O)R31R32, P(═S)R33R34, S(═O)2R35, and S(═O)R36;
R11, R12, R13, R14, R15, R16, R17, and R18 are each independently hydrogen;
R31, R32, R33, R34, R35, and R36 are each independently selected from hydrogen, deuterium, a halogen group, a nitro group, a cyano group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group;
L1 and L2 are each independently selected from 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;
a1 and a2 are each independently an integer from 0 to 3;
m and n are each independently an integer selected from 1 to 2; and
at least one substituent of the substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C1-C60 alkoxy group, substituted C3-C10 cycloalkyl group, substituted C2-C10 heterocycloalkyl group, substituted C3-C10 cycloalkenyl group, substituted C2-C10 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C1-C60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic condensed heteropolycyclic group, substituted C6-C60 arylene group, substituted C1-C60 heteroarylene group, a substituted divalent non-aromatic condensed polycyclic group, and a substituted divalent non-aromatic condensed heteropolycyclic group is selected from the group consisting of:
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-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 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 C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-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, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), and —B(Q16)(Q17),
a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-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, and
a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-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 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-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-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, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), and —B(Q26)(Q27),
wherein Q11 to Q17 and Q21 to Q27 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-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

### Claim 2 (depends on 1)

The compound of claim 1, wherein
R31, R32, R33, R34, R35, and R36 in Formula 1 are each independently a substituted or unsubstituted C6-C60 aryl group.

### Claim 3 (depends on 1)

The compound of claim 1, wherein
L1 and L2 in Formula 1 are each independently one of Formulae 2a to 2d:
wherein “*” in Formulae 2a to 2d indicates a binding site.

### Claim 4 (depends on 1)

The compound of claim 1, wherein
R1 in Formula 1 is selected from deuterium, a cyano group, P(═O)R31R32, P(═S)R33R34, and a group represented by one of Formulae 3a to 3k;
and R2 in Formula 1 is selected from hydrogen, deuterium, a cyano group, P(═O)R31R32, P(═S)R33R34, and a group represented by one of Formulae 3a to 3k:
wherein in Formulae 3a to 3k, H1 is selected from CR41R42, NR43, O, and S;
R41 to R43, Z1, and Z2 are each independently selected from hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carboxy group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C1 to C20 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;
p in Formulae 3a and 3k is an integer selected from 1 to 4, p in Formula 3c is an integer selected from 1 to 3, p in Formula 3d is an integer selected from 1 to 9, p in Formulae 3e and 3g is an integer selected from 1 to 6, p in Formula 3f is an integer selected from 1 to 5, and p in Formulae 3h, 3i, and 3j is an integer selected from 1 to 7, wherein when p is 2 or more, two or more Z1(s) are identical to or different from each other; and
* indicates a binding site.

### Claim 5 (depends on 1)

The compound of claim 1, wherein
the compound of Formula 1 is represented by Formula 2:

### Claim 6 (depends on 1)

The compound of claim 1, wherein
the compound of Formula 1 is represented by Formula 3:

### Claim 7 (depends on 1)

The compound of claim 1, wherein
the compound of Formula 1 is represented by Formula 4:

### Claim 8 (depends on 1)

The compound of claim 1, wherein
the compound of Formula 1 is represented by Formula 5:

### Claim 9

A compound represented by one of Compounds 1 to 113 and 124 to 127:

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

### Claim 11 (depends on 10)

The organic light-emitting device of claim 10, 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, the hole transport region comprising at least one selected from a hole transport layer, a hole injection layer, and an electron blocking layer, and
ii) an electron transport region between the emission layer and the second electrode, the electron transport region comprising an electron transport layer and at least one selected from a hole blocking layer and an electron injection layer.

### Claim 12 (depends on 11)

The organic light-emitting device of claim 11, wherein
the electron transport region comprises the compound represented by Formula 1.

### Claim 13 (depends on 11)

The organic light-emitting device of claim 11, wherein
the electron transport layer comprises the compound represented by Formula 1.

### Claim 14 (depends on 11)

The organic light-emitting device of claim 11, wherein
the hole transport region comprises a charge-generating material.

### Claim 15 (depends on 14)

The organic light-emitting device of claim 14, wherein
the charge-generating material is a p-dopant.

### Claim 16 (depends on 14)

The organic light-emitting device of claim 14, wherein
the charge-generating material is HT-D1 or F4-TCNQ:

### Claim 17 (depends on 11)

The organic light-emitting device of claim 11, wherein
the electron transport region comprises a metal-containing material.

### Claim 18 (depends on 11)

The organic light-emitting device of claim 11, wherein
the electron transport region comprises ET-D1 or ET-D2:

### Claim 19 (depends on 10)

A display apparatus comprising the organic light-emitting device of claim 10, wherein the first electrode of the organic light-emitting device is electrically coupled to a source electrode or a drain electrode of a thin film transistor.