Novel compound and organic electroluminescent device comprising same
AssigneeDoosan Corporation
InventorsTae Hyung KIM, In Hyuk LEE, Yong Hwan LEE, Jin Yong SHIN, Ho Cheol PARK, Chang Jun LEE, Eun Jung LEE, Young Mi BEAK
Life of this patent
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Abstract
The present disclosure relates to a novel compound having excellent hole injection capabilities and transport capabilities, light-emitting capabilities, and the like, and an organic electroluminescent device which includes the compound in one or more organic material layers thereof so as to improve characteristics such as light-emitting efficiency, driving voltage, and a service life.
Claims17
-11. (canceled)
A compound of the following Formula 1:
- in Formula 1,
- Y1 to Y4 are each independently N or CR3, and in this case, when CR3 is present in a plural number, they are the same as or different from each other, and
- provided that at least one of Y1 and Y2, Y2 and Y3, and Y3 and Y4 is CR3, and forms a fused ring of the following Formula 2;
- in Formula 2,
- Y5 to Y8 are each independently selected from N or CR4, and in this case, when CR4 is present in a plural number, they are the same as or different from each other, and
- provided that at least one of Y5 to Y8 is CR4, and in this case, at least one R4 is a substituent of the following Formula 3;
- in Formula 3,
- L is a single bond, or selected from the group consisting of a substituted or unsubstituted C6 to C60 arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms, and
- in this case, one or more substituents each introduced into the arylene group and the heteroarylene group of L are each independently selected from the group consisting of deuterium, halogen, cyano, a C1 to C40 alkyl group, a C3 to C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6 to C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1 to C40 alkyloxy group, a C6 to C60 aryloxy group, and a C6 to C60 arylamine group, and provided that when the substituent is present in a plural number, they are optionally the same as or different from each other;
- Ra and Rb are each independently selected from the group consisting of a substituted or unsubstituted C1 to C40 alkyl group, a substituted or unsubstituted C3 to C40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, and
- in this case, one or more substituents each introduced into the alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, and the heteroaryl group of Ra and Rb are each independently selected from the group consisting of deuterium, halogen, cyano, a C1 to C40 alkyl group, a C3 to C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6 to C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1 to C40 alkyloxy group, a C6 to C60 aryloxy group, a C1 to C40 alkylsilyl group, a C6 to C60 arylsilyl group, a C1 to C40 alkyl boron group, a C6 to C60 aryl boron group, a C6 to C60 arylphosphine group, a C6 to C60 arylphosphine oxide group, and a C6 to C60 arylamine group, and provided that when the substituent is present in a plural number, they are optionally the same as or different from each other;
- provided that L, Ra, and Rb optionally combine with an adjacent substituent to form a fused ring;
- X1 and X2 are each independently selected from the group consisting of O, S, Se, N(Ar1), C(Ar2)(Ar3), and Si(Ar4)(Ar5), and in this case, when N(Ar1) is present in a plural number, they are the same as or different from each other, when C(Ar2)(Ar3) is present in a plural number, they are the same as or different from each other, and when Si(Ar4)(Ar5) is present in a plural number, they are the same as or different from each other, and
- provided that at least one of X1 and X2 is N(Ar1);
- Ar1 to Ar5 are each independently selected from the group consisting of a substituted or unsubstituted C1 to C40 alkyl group, a substituted or unsubstituted C3 to C40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C1 to C40 alkyloxy group, a substituted or unsubstituted C6 to C60 aryloxy group, a substituted or unsubstituted C1 to C40 alkylsilyl group, a substituted or unsubstituted C6 to C60 arylsilyl group, a substituted or unsubstituted C1 to C40 alkyl boron group, a substituted or unsubstituted C6 to C60 aryl boron group, a substituted or unsubstituted C6 to C60 arylphosphine group, a substituted or unsubstituted C6 to C60 arylphosphine oxide group, or a substituted or unsubstituted C6 to C60 arylamine group;
- R1 to R4 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1 to C40 alkyl group, a substituted or unsubstituted C3 to C40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C1 to C40 alkyloxy group, a substituted or unsubstituted C6 to C60 aryloxy group, a substituted or unsubstituted C1 to C40 alkylsilyl group, a substituted or unsubstituted C6 to C60 arylsilyl group, a substituted or unsubstituted C1 to C40 alkyl boron group, a substituted or unsubstituted C6 to C60 aryl boron group, a substituted or unsubstituted C6 to C60 arylphosphine group, a substituted or unsubstituted C6 to C60 arylphosphine oxide group, and a substituted or unsubstituted C6 to C60 arylamine group, and they form or do not form a fused ring with an adjacent group;
- and
- one or more substituents each introduced into the alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, and the arylamine group of R1 to R4 and Ar1 to Ar5 are each independently selected from the group consisting of deuterium, halogen, cyano, a C1 to C40 alkyl group, a C3 to C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6 to C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1 to C40 alkyloxy group, a C6 to C60 aryloxy group, a substituted or unsubstituted C1 to C40 alkylsilyl group, a C6 to C60 arylsilyl group, a C1 to C40 alkyl boron group, a C6 to C60 aryl boron group, a C6 to C60 arylphosphine group, a C6 to C60 arylphosphine oxide group, and a C6 to C60 arylamine group, and provided that when the substituent is present in a plural number, they are optionally the same as or different from each other.
A compound selected from the group consisting of compounds of the following Formulae 4 to 9:
- in Formulae 4 to 9,
- Y1 to Y4 are each independently N or CR3, and in this case, when CR3 is present in a plural number, they are the same as or different from each other;
- Y5 to Y8 are each independently selected from N or CR4, and in this case, when CR4 is present in a plural number, they are the same as or different from each other, and
- provided that at least one of Y5 to Y8 is CR4, and in this case, at least one of one or more R4's is a substituent of the following Formula 3;
- in Formula 3,
- L is a single bond, or selected from the group consisting of a substituted or unsubstituted C6 to C60 arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms, and
- in this case, one or more substituents each introduced into the arylene group and the heteroarylene group of L are each independently selected from the group consisting of deuterium, halogen, cyano, a C1 to C40 alkyl group, a C3 to C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6 to C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1 to C40 alkyloxy group, a C6 to C60 aryloxy group, and a C6 to C60 arylamine group, and provided that when the substituent is present in a plural number, they are optionally the same as or different from each other;
- Ra and Rb are each independently selected from the group consisting of a substituted or unsubstituted C1 to C40 alkyl group, a substituted or unsubstituted C3 to C40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, and
- in this case, one or more substituents each introduced into the alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, and the heteroaryl group of Ra and Rb are each independently selected from the group consisting of deuterium, halogen, cyano, a C1 to C40 alkyl group, a C3 to C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6 to C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1 to C40 alkyloxy group, a C6 to C60 aryloxy group, a C1 to C40 alkylsilyl group, a C6 to C60 arylsilyl group, a C1 to C40 alkyl boron group, a C6 to C60 aryl boron group, a C6 to C60 arylphosphine group, a C6 to C60 arylphosphine oxide group, and a C6 to C60 arylamine group, and provided that when the substituent is present in a plural number, they are optionally the same as or different from each other;
- provided that L, Ra, and Rb optionally combine with an adjacent substituent to form a fused ring;
- X1 and X2 are each independently selected from the group consisting of O, S, Se, N(Ar1), C(Ar2)(Ar3), and Si(Ar4)(Ar5), and in this case, when N(Ar1) is present in a plural number, they are the same as or different from each other, when C(Ar2)(Ar3) is present in a plural number, they are the same as or different from each other, and when Si(Ar4)(Ar5) is present in a plural number, they are the same as or different from each other, and
- provided that at least one of X1 and X2 is N(Ar1);
- Ar1 to Ar5 are each independently selected from the group consisting of a substituted or unsubstituted C1 to C40 alkyl group, a substituted or unsubstituted C3 to C40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C1 to C40 alkyloxy group, a substituted or unsubstituted C6 to C60 aryloxy group, a substituted or unsubstituted C1 to C40 alkylsilyl group, a substituted or unsubstituted C6 to C60 arylsilyl group, a substituted or unsubstituted C1 to C40 alkyl boron group, a substituted or unsubstituted C6 to C60 aryl boron group, a substituted or unsubstituted C6 to C60 arylphosphine group, a substituted or unsubstituted C6 to C60 arylphosphine oxide group, or a substituted or unsubstituted C6 to C60 arylamine group;
- R1 to R4 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1 to C40 alkyl group, a substituted or unsubstituted C3 to C40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C1 to C40 alkyloxy group, a substituted or unsubstituted C6 to C60 aryloxy group, a substituted or unsubstituted C1 to C40 alkylsilyl group, a substituted or unsubstituted C6 to C60 arylsilyl group, a substituted or unsubstituted C1 to C40 alkyl boron group, a substituted or unsubstituted C6 to C60 aryl boron group, a substituted or unsubstituted C6 to C60 arylphosphine group, a substituted or unsubstituted C6 to C60 arylphosphine oxide group, and a substituted or unsubstituted C6 to C60 arylamine group, and these form or do not form a fused ring with an adjacent group;
- and
- one or more substituents each introduced into the alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, and the arylamine group of R1 to R4 and Ar1 to Ar5 are each independently selected from the group consisting of deuterium, halogen, cyano, a C1 to C40 alkyl group, a C3 to C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6 to C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1 to C40 alkyloxy group, a C6 to C60 aryloxy group, a substituted or unsubstituted C1 to C40 alkylsilyl group, a C6 to C60 arylsilyl group, a C1 to C40 alkyl boron group, a C6 to C60 aryl boron group, a C6 to C60 arylphosphine group, a C6 to C60 arylphosphine oxide group, and a C6 to C60 arylamine group, and provided that when the substituent is present in a plural number, they are optionally the same as or different from each other.
Dependencies are inferred from the claim text.