# US 12,225,813 B2 · Organic compound and organic electroluminescent device comprising the same

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- Number: US 12,225,813 B2
- Document ID: US12225813B2
- Status: Granted
- Kind: B2
- Application number: 16/615,891
- Filed: 2018-05-02
- Published: 2020-05-07
- Granted: 2025-02-11
- Earliest claimed: 2017-05-23
- Assignees: Doosan Solus Co., Ltd.
- Applicants: Doosan Solus Co., Ltd.
- Inventors: Hyung Chan Bae; Young Bae Kim; Ho Jun Son
- Web page: https://patentgrep.com/patent/US12225813B2

## CPC

- C07D 409/10: linked by a carbon chain containing aromatic rings
- C07D 251/24: to three ring carbon atoms
- C07D 263/54: Benzoxazoles; Hydrogenated benzoxazoles
- C07D 263/57: Aryl or substituted aryl radicals
- C07D 405/10: linked by a carbon chain containing aromatic rings
- C07D 405/14: containing three or more hetero rings
- C07D 413/10: linked by a carbon chain containing aromatic rings
- C07D 413/14: containing three or more hetero rings
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- 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 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 71/164: {using vacuum deposition}
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/342: {comprising iridium}
- H10K 2101/10: Triplet emission
- H10K 2102/351: {Thickness}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A novel compound of the Chemical Formula 1 and an organic electroluminescent device including the compound are disclosed. The novel compound, when included in an organic material layer, preferably a light emitting layer, of an organic electroluminescent device, can improve luminous efficiency, driving voltage, lifetime and other properties of the organic electroluminescent device:

## Claims

### Claim 1

A compound of the following Chemical Formula 1:
wherein, in Chemical Formula 1,
L1 is selected from the group consisting of a single bond, a C6˜C18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
Ar1 is a substituent represented by any one of the following Chemical Formula 13, Chemical Formula 14, and Chemical Formula C-1 to Chemical Formula C-6,
in Chemical Formulas 13, 14, and C1-C6,
* means a part where a bond is formed;
Z1, Z3 and Z5 are each independently N or C (R8), wherein at least one of Z1, Z3 and Z5 is N;
o is an integer of 0 to 4;
R8 to R14 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1˜C40 alkyloxy group, a C6˜C60 aryloxy group, a C3˜C40 alkylsilyl group, a C6˜C60 arylsilyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group and a C6˜C60 arylamine group, or bond to adjacent groups to form a fused ring; and
the alkyl group, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the aryloxy group, the alkyloxy group, the cycloalkyl group, the heterocycloalkyl group, the arylamine group, the alkylsilyl group, the alkylboron group, the arylboron group, the arylphosphanyl group, the mono or diarylphosphinyl group and the arylsilyl group of R8, to R14 are each independently unsubstituted or substituted with one or more types of substituents selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C6˜C60 aryloxy group, a C1˜C40 alkyloxy group, a C6˜C60 arylamine group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C1˜C40 alkylsilyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group and a C6˜C60 arylsilyl group, and when substituted with a plurality of the substituents, these are the same as or different from each other;
any one of X1 and X2, X2 and X3, X3 and X4, and X4 and X5 bonds to a ring of the following Chemical Formula 2 or 4 to form a fused ring;
m and n are an integer of 4;
R1 and R2 are hydrogen;
X1 to X5 not forming a fused ring with a ring of the following Chemical Formula 2 or 4 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1˜C40 alkyloxy group, a C6˜C60 aryloxy group, a C3˜C40 alkylsilyl group, a C6˜C60 arylsilyl group, a C1˜C40 alkylsulfonyl group, a C6˜C60 arylsulfonyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group, a C1˜C40 alkylcarbonyl group, a C6˜C60 arylcarbonyl group and a C6˜C60 arylamine group; and
the alkyl group, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the aryloxy group, the alkyloxy group, the cycloalkyl group, the heterocycloalkyl group, the arylamine group, the alkylsilyl group, the alkylboron group, the arylboron group, the arylphosphanyl group, the mono or diarylphosphinyl group and the arylsilyl group of R1, R2, and X1 to X5 not forming a fused ring with a ring represented by the following Chemical Formula 2 or 4 are each independently unsubstituted or substituted with one or more types of substituents selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C6˜C60 aryloxy group, a C1˜C40 alkyloxy group, a C6˜C60 arylamine group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C1˜C40 alkylsilyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group and a C6˜C60 arylsilyl group, and when substituted with a plurality of the substituents, these are the same as or different from each other;
wherein in Chemical Formula 2 or 4,
wherein in Chemical Formula 2 or 4,
a dotted line means a part that is fused to Chemical Formula 1;
p is an integer of 0 to 5;
Y1 is O;
R3 is selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1˜C40 alkyloxy group, a C6˜C60 aryloxy group, a C3˜C40 alkylsilyl group, a C6˜C60 arylsilyl group, a C1˜C40 alkylsulfonyl group, a C6˜C60 arylsulfonyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group, a C1˜C40 alkylcarbonyl group, a C6˜C60 arylcarbonyl group and a C6˜C60 arylamine group; and
the alkyl group, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the aryloxy group, the alkyloxy group, the cycloalkyl group, the heterocycloalkyl group, the arylamine group, the alkylsilyl group, the alkylsulfonyl group, the arylsulfonyl group, the alkylboron group, the arylboron group, the arylphosphanyl group, the mono or diarylphosphinyl group, the alkylcarbonyl group, the arylcarbonyl group and the arylsilyl group of R3 to R6 are each independently unsubstituted or substituted with one or more types of substituents selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C6˜C60 aryloxy group, a C1˜C40 alkyloxy group, a C6˜C60 arylamine group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C1˜C40 alkylsilyl group, a C1˜C40 alkylsulfonyl group, a C6˜C60 arylsulfonyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group, a C1˜C40 alkylcarbonyl group, a C6˜C60 arylcarbonyl group and a C6˜C60 arylsilyl group, and when substituted with a plurality of the substituents, these are the same as or different from each other.

### Claim 2

A compound of the following Chemical Formula 1:
wherein in Chemical Formula 1,
L1 is selected from the group consisting of a single bond, a C6˜C18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
any one of X1 and X2, X2 and X3, X3 and X4, and X4 and X5 bonds to a ring of the following Chemical Formula 3 to form a fused ring;
m and n are each independently an integer of 0 to 4;
R1, R2, and X1 to X5 not forming a fused ring with a ring of the following Chemical Formula 3 is each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1˜C40 alkyloxy group, a C6˜C60 aryloxy group, a C3˜C40 alkylsilyl group, a C6˜C60 arylsilyl group, a C1˜C40 alkylsulfonyl group, a C6˜C60 arylsulfonyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group, a C1˜C40 alkylcarbonyl group, a C6˜C60 arylcarbonyl group and a C6˜C60 arylamine group; and
the alkyl group, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the aryloxy group, the alkyloxy group, the cycloalkyl group, the heterocycloalkyl group, the arylamine group, the alkylsilyl group, the alkylboron group, the arylboron group, the arylphosphanyl group, the mono or diarylphosphinyl group and the arylsilyl group of R1, R2, and X1 to X5 not forming a fused ring with a ring of the following Chemical Formula 3 is each independently unsubstituted or substituted with one or more types of substituents selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C6˜C60 aryloxy group, a C1˜C40 alkyloxy group, a C6˜C60 arylamine group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C1˜C40 alkylsilyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group and a C6˜C60 arylsilyl group, and when substituted with a plurality of the substituents, these are the same as or different from each other;
wherein in Chemical Formula 3,
a dotted line means a part that is fused to Chemical Formula 1;
q is an integer of 0 to 4;
Y2 is O, S or C (R5) (R6);
R3, R5, and R6 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1˜C40 alkyloxy group, a C6˜C60 aryloxy group, a C3˜C40 alkylsilyl group, a C6˜C60 arylsilyl group, a C1˜C40 alkylsulfonyl group, a C6˜C60 arylsulfonyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group, a C1˜C40 alkylcarbonyl group, a C6˜C60 arylcarbonyl group and a C6˜C60 arylamine group; and
the alkyl group, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the aryloxy group, the alkyloxy group, the cycloalkyl group, the heterocycloalkyl group, the arylamine group, the alkylsilyl group, the alkylsulfonyl group, the arylsulfonyl group, the alkylboron group, the arylboron group, the arylphosphanyl group, the mono or diarylphosphinyl group, the alkylcarbonyl group, the arylcarbonyl group and the arylsilyl group of R3, R5, and R6 are each independently unsubstituted or substituted with one or more types of substituents selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C6˜C60 aryloxy group, a C1˜C40 alkyloxy group, a C6˜C60 arylamine group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C1˜C40 alkylsilyl group, a C1˜C40 alkylsulfonyl group, a C6˜C60 arylsulfonyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group, a C1˜C40 alkylcarbonyl group, a C6˜C60 arylcarbonyl group and a C6˜C60 arylsilyl group, and when substituted with a plurality of the substituents, these are the same as or different from each other;
Ar1 is a substituent represented by any one of the following Chemical Formula 13, Chemical Formula C-1 to Chemical Formula C-6,
Z1, Z3 and Z5 are each independently N or C (R8), wherein at least one of Z1, Z3 and Z5 is N;
o is an integer of 0 to 4;
R8 is selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1˜C40 alkyloxy group, a C6˜C60 aryloxy group, a C3˜C40 alkylsilyl group, a C6˜C60 arylsilyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group and a C6˜C60 arylamine group, or bonds to adjacent groups to form a fused ring, and when R8 is present in plural numbers, these are the same as or different from each other; and R9 and R10 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1˜C40 alkyloxy group, a C6˜C60 aryloxy group, a C3˜C40 alkylsilyl group, a C6˜C60 arylsilyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group and a C6˜C60 arylamine group;
the alkyl group, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the aryloxy group, the alkyloxy group, the cycloalkyl group, the heterocycloalkyl group, the arylamine group, the alkylsilyl group, the alkylboron group, the arylboron group, the arylphosphanyl group, the mono or diarylphosphinyl group and the arylsilyl group of R8 and R10 are each independently unsubstituted or substituted with one or more types of substituents selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C6˜C60 aryloxy group, a C1˜C40 alkyloxy group, a C6˜C60 arylamine group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C1˜C40 alkylsilyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group and a C6˜C60 arylsilyl group, and when substituted with a plurality of the substituents, these are the same as or different from each other; and
R11 and R12 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1˜C40 alkyloxy group, a C6˜C60 aryloxy group, a C3˜C40 alkylsilyl group, a C6˜C60 arylsilyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group and a C6˜C60 arylamine group; and
the alkyl group, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the aryloxy group, the alkyloxy group, the cycloalkyl group, the heterocycloalkyl group, the arylamine group, the alkylsilyl group, the alkylboron group, the arylboron group, the arylphosphanyl group, the mono or diarylphosphinyl group and the arylsilyl group of R11 and R12 are each independently unsubstituted or substituted with one or more types of substituents selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C6˜C60 aryloxy group, a C1˜C40 alkyloxy group, a C6˜C60 arylamine group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C1˜C40 alkylsilyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group and a C6˜C60 arylsilyl group, and when substituted with a plurality of the substituents, these are the same as or different from each other;
provided that when Ar1 is represented by Chemical Formula C-1, R12 is not hydrogen or deuterium;
provided that when Ar1 is represented by Chemical Formula 13, compounds meet conditions that at least one of R9 and R10 is a heteroaryl group having 5 to 60 nuclear atoms, or that L1 is a heteroarylene group having 5 to 18 nuclear atoms.

### Claim 3 (depends on 1)

The compound of claim 1, which is represented by the following Chemical Formula 5 or 10:
wherein, in Chemical Formula 5 or 10,
p, q, m, n, R1 to R3, L1 and Ar1 have the same definitions as in claim 1.

### Claim 4 (depends on 1)

The compound of claim 1, wherein L1 is a direct bond, or a linker selected from the group consisting of the following Chemical Formula A-1 to A-6:
wherein in Chemical Formula A-1 to A-6,
* means a part where a bond is formed.

### Claim 5 (depends on 2)

The compound of claim 2, wherein R12 is selected from the group consisting of a C1˜C40 alkyl group, a C6˜C60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms; and
the alkyl group, the aryl group and the heteroaryl group of R12 are each independently unsubstituted or substituted with one or more types of substituents selected from the group consisting of a C1˜C40 alkyl group, a C6˜C60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms, and when substituted with a plurality of the substituents, these are the same as or different from each other.

### Claim 6 (depends on 1)

The compound of claim 1, wherein R13 and R14 are each independently selected from the group consisting of a C1˜C30 alkyl group, a C6˜C30 aryl group and a heteroaryl group having 5 to 30 nuclear atoms.

### Claim 7 (depends on 1)

The compound of claim 1, which is selected from the group consisting of the following compounds:

### Claim 8 (depends on 1)

An organic electroluminescent device comprising:
an anode;
a cathode; and
one or more organic material layers provided between the anode and the cathode,
wherein at least one of the one or more organic material layers includes the compound of the Chemical Formula 1 of claim 1.

### Claim 9 (depends on 8)

The organic electroluminescent device of claim 8, wherein the organic material layer includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron transport layer, an electron transport auxiliary layer and a light emitting layer.

### Claim 10 (depends on 2)

The compound of claim 2, which is represented by any one of the following Chemical Formula 6 to 9:
wherein, in Chemical Formula 6 to 9,
p is an integer of 0 to 5;
L1, Ar1, q, m, n, R1, R2, and R3 have the same definitions as in claim 2.

### Claim 11 (depends on 2)

The compound of claim 2, which is selected from the group consisting of the following compounds:

### Claim 12 (depends on 2)

An organic electroluminescent device comprising:
an anode;
a cathode; and
one or more organic material layers provided between the anode and the cathode,
wherein at least one of the one or more organic material layers includes the compound of Chemical Formula 1 of claim 2.