# US 12,225,818 B2 · Organic light-emitting device

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- Number: US 12,225,818 B2
- Document ID: US12225818B2
- Status: Granted
- Kind: B2
- Application number: 16/969,513
- Filed: 2019-06-11
- Published: 2020-12-31
- Granted: 2025-02-11
- Earliest claimed: 2018-06-11
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Joo Ho Kim; Ji Young Choi; Woochul Lee; Dong Hoon Lee; Dongheon Kim; Sang Duk Suh; Hyungjin Lee
- Web page: https://patentgrep.com/patent/US12225818B2

## CPC

- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 85/656: {comprising two or more different heteroatoms per ring (H10K85/652 takes precedence)}
- 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 85/658: {Organoboranes}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 2101/90: {Multiple hosts in the emissive layer}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

An organic light emitting device including a first electrode, a second electrode, and a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer includes a compound of Chemical Formula 1, a compound of Chemical Formula 2 and a compound of Chemical Formula 3.

## Claims

### Claim 1

An organic light emitting device comprising:
a first electrode;
a second electrode; and
a light emitting layer provided between the first electrode and the second electrode,
wherein the light emitting layer includes a compound of Chemical Formula 1, a compound of Chemical Formula 2, and a compound of Chemical Formulae 3-5 or 3-6:
wherein in Chemical Formulae 1 and 2:
L1 to L4 are the same as or different from each other, and each independently a direct bond or a substituted or unsubstituted arylene group;
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group;
Ar3 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group;
R1 to R3 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, an amino group, an aryl group, or a heteroaryl group; and
a1 and a2 are each independently an integer of 0 to 8, a3 is an integer of 0 to 7, and when a1 is 2 or greater, the R1s are the same as or different from each other, when a2 is 2 or greater, the R2s are the same as or different from each other, and when a3 is 2 or greater, the R3s are the same as or different from each other:
wherein in Chemical Formulae 3-5 and 3-6:
X is B, P=O or P=S;
A1 to A3 are the same as or different from each other, and each independently a monocyclic or polycyclic ring;
A4 and A5 are the same as or different from each other, and each independently a monocyclic or polycyclic ring;
Y2 is O or NR12;
Y3 is CR21R22 or SiR27R28, Y4 is a direct bond, O, CR23R24 or NR14, and Y5 is a direct bond, O, CR25R26 or NR15;
R12, R14, and R15 are the same as or different from each other, and each independently hydrogen, deuterium, an alkyl group, a cycloalkyl group, or an aryl group that is unsubstituted or substituted with an alkyl group, an arylalkyl group or an aryl group;
R21 and R22 are the same as or different from each other, and each independently hydrogen, deuterium, an alkyl group, a cycloalkyl group or an aryl group, or bond to each other to form a ring;
R23 and R24 are the same as or different from each other, and each independently hydrogen, deuterium, an alkyl group, a cycloalkyl group or an aryl group, or bond to each other to form a ring;
R25 and R26 are the same as or different from each other, and each independently hydrogen, deuterium, an alkyl group, a cycloalkyl group or an aryl group, or bond to each other to form a ring;
R27 and R28 are the same as or different from each other, and each independently hydrogen, deuterium, an alkyl group, a cycloalkyl group or an aryl group;
T1 to T5 are the same as or different from each other, and each independently hydrogen, deuterium, a hydroxyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an aryl group, a heteroaryl group, or —NR41R42, and R41 and R42 are the same as or different from each other and each independently hydrogen, an alkyl group, a heteroaryl group, or an aryl group that unsubstituted or substituted with an alkyl group or a silyl group; and
c1 to c5 are each independently an integer of 0 or greater, and when c1 is 2 or greater, the T1s are the same as or different from each other, when c2 is 2 or greater, the T2s are the same as or different from each other, when c3 is 2 or greater, the T3s are the same as or different from each other, when c4 is 2 or greater, the T4s are the same as or different from each other, and when c5 is 2 or greater, the T5s are the same as or different from each other.

### Claim 2 (depends on 1)

The organic light emitting device of claim 1, wherein L1 to L4 are the same as or different from each other, and each independently a direct bond; a phenylene group; a biphenylene group; or a naphthalene group.

### Claim 3 (depends on 1)

The organic light emitting device of claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; a biphenyl group; a terphenyl group; or a naphthyl group.

### Claim 4 (depends on 1)

The organic light emitting device of claim 1, wherein Ar3 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted fluoranthenyl group; a substituted or unsubstituted pyrenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazolyl group.

### Claim 5 (depends on 1)

The organic light emitting device of claim 1, wherein A1 to A3 are the same as or different from each other, and each independently benzene, naphthalene, triphenylene, 9,9′-spirobifluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, carbazole, indolocarbazole, naphthobenzofuran,

### Claim 6 (depends on 1)

The organic light emitting device of claim 1, wherein the compound of Chemical Formula 1 is one selected from among the following compounds:

### Claim 7 (depends on 1)

The organic light emitting device of claim 1, wherein the compound of Chemical Formula 2 is one selected from among the following compounds:

### Claim 8

An organic light emitting device comprising:
a first electrode;
a second electrode; and
a light emitting layer provided between the first electrode and the second electrode,
wherein the light emitting layer includes a compound of Chemical Formula 1, a compound of Chemical Formula 2, and a compound BD-11 or BD-18:
wherein in Chemical Formulae 1 and 2:
L1 to L4 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group;
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group;
Ar3 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
R1 to R3 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a cyano group; a silyl group; an alkyl group; a cycloalkyl group; an alkenyl group; an alkynyl group; an alkoxy group; an aryloxy group; an amino group; an aryl group; or a heteroaryl group; and
a1 and a2 are each independently an integer of 0 to 8, a3 is an integer of 0 to 7, and when a1 is 2 or greater, R1s are the same as or different from each other, when a2 is 2 or greater, R2s are the same as or different from each other, and when a3 is 2 or greater, R3s are the same as or different from each other;

### Claim 9 (depends on 8)

The organic light emitting device of claim 8, wherein:
L1 to L4 are the same as or different from each other, and each independently a direct bond; a phenylene group; a biphenylene group; or a naphthalene group; and
Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; a biphenyl group; a terphenyl group; or a naphthyl group.

### Claim 10 (depends on 8)

The organic light emitting device of claim 8, wherein Ar3 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted fluoranthenyl group; a substituted or unsubstituted pyrenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazolyl group.

### Claim 11 (depends on 8)

The organic light emitting device of claim 8, wherein the compound of Chemical Formula 1 is one selected from among the following compounds:

### Claim 12 (depends on 8)

The organic light emitting device of claim 8, wherein the compound of Chemical Formula 2 is one selected from among the following compounds:

### Claim 13

An organic light emitting device comprising:
a first electrode;
a second electrode; and
a light emitting layer provided between the first electrode and the second electrode,
wherein the light emitting layer includes a compound of Chemical Formula 1, a compound of Chemical Formula 2, and a compound of Chemical Formula 3-2:
wherein in Chemical Formulae 1 and 2:
L1 to L4 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group;
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group;
Ar3 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
R1 to R3 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a cyano group; a silyl group; an alkyl group; a cycloalkyl group; an alkenyl group; an alkynyl group; an alkoxy group; an aryloxy group; an amino group; an aryl group; or a heteroaryl group; and
a1 and a2 are each independently an integer of 0 to 8, a3 is an integer of 0 to 7, and when a1 is 2 or greater, R1s are the same as or different from each other, when a2 is 2 or greater, R2s are the same as or different from each other, and when a3 is 2 or greater, R3s are the same as or different from each other,
wherein in Chemical Formulae 3-2:
X is B;
A1 to A3 are the same as or different from each other, and each independently a monocyclic or polycyclic ring;
Y1 is O or NR11, and Y2 is O or NR12;
Y3 is SiR27R28;
R11 and R12 are the same as or different from each other, and each independently hydrogen; deuterium; an alkyl group; a cycloalkyl group; or an aryl group unsubstituted or substituted with an alkyl group, an arylalkyl group or an aryl group;
R27 and R28 are the same as or different from each other, and each independently hydrogen, deuterium, an alkyl group, a cycloalkyl group or an aryl group;
T1 to T3 are the same as or different from each other, and each independently hydrogen; deuterium; a hydroxyl group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryloxy group; an aryl group; a heteroaryl group; or —NR41R42, and R41 and R42 are the same as or different from each other and each independently hydrogen; an alkyl group; an aryl group unsubstituted or substituted with an alkyl group or a silyl group; or a heteroaryl group; and
c1 to c3 are each independently an integer of 0 or greater, and when c1 is 2 or greater, T1s are the same as or different from each other, when c2 is 2 or greater, T2s are the same as or different from each other, when c3 is 2 or greater, T3s are the same as or different from each other.

### Claim 14 (depends on 13)

The organic light emitting device of claim 13, wherein:
L1 to L4 are the same as or different from each other, and each independently a direct bond; a phenylene group; a biphenylene group; or a naphthalene group; and
Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; a biphenyl group; a terphenyl group; or a naphthyl group.

### Claim 15 (depends on 13)

The organic light emitting device of claim 13, wherein Ar3 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted fluoranthenyl group; a substituted or unsubstituted pyrenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazolyl group.

### Claim 16 (depends on 13)

The organic light emitting device of claim 13, wherein A1 to A3 are the same as or different from each other, and each independently benzene, naphthalene, triphenylene, 9,9′-spirobifluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, carbazole, indolocarbazole, naphthobenzofuran,

### Claim 17 (depends on 13)

The organic light emitting device of claim 13, wherein Chemical Formula 3-2 is Chemical Formula 4-9:
wherein in Chemical Formula 4-9:
X and A1 to A3 have the same definitions as in Chemical Formula 3-2;
R11 and R12 are the same as or different from each other, and each independently hydrogen; deuterium; an alkyl group; a cycloalkyl group; or an aryl group unsubstituted or substituted with an alkyl group, an arylalkyl group or an aryl group;
R27 and R28 are the same as or different from each other, and each independently hydrogen, deuterium, an alkyl group, a cycloalkyl group or an aryl group;
T1 to T3 are the same as or different from each other, and each independently hydrogen; deuterium; a hydroxyl group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryloxy group; an aryl group; a heteroaryl group; or —NR41R42, and R41 and R42 are the same as or different from each other and each independently hydrogen; an alkyl group; a cycloalkyl group; an aryl group unsubstituted or substituted with an alkyl group or a silyl group; or a heteroaryl group; and
c1 to c3 are each independently an integer of 0 or greater, and when c1 is 2 or greater, T1s are the same as or different from each other, when c2 is 2 or greater, T2s are the same as or different from each other, when c3 is 2 or greater, T3s are the same as or different from each other, when c4 is 2 or greater, T4s are the same as or different from each other, and when c5 is 2 or greater, T5s are the same as or different from each other.

### Claim 18 (depends on 13)

The organic light emitting device of claim 13, wherein the compound of Chemical Formula 1 is one selected from among the following compounds:

### Claim 19 (depends on 13)

The organic light emitting device of claim 13, wherein the compound of Chemical Formula 2 is one selected from among the following compounds: