Organic light-emitting compound and organic electroluminescent device using same
View Patent ↗The present invention relates to a novel indole-based compound having superior hole injection and transport capabilities, light-emitting capabilities, and the like, and an organic electroluminescent device which comprises the indole-based compound in one or more organic layers thereof so as to thereby achieve improved characteristics, such as light-emitting efficiency, driving voltage, and lifespan characteristics.
1. A compound of the following Formulae 1a to 1f:
wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms and a C 6 to C 60 arylamine group,
Y 1 to Y 4 are each independently N or CR 3 ,
Y 5 to Y 8 are each independently N or CR 4 ,
X 1 and X 2 are each independently selected from the group consisting of Se, N(Ar 1 ), C(Ar 2 )(Ar 3 ) and Si(Ar 4 )(Ar 5 ), and at least one of X 1 and X 2 is N(Ar 1 ),
R 3 and R 4 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 to C 60 aryloxy group, a C 6 to C 60 arylsilyl group, a C 6 to C 60 aryl boron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group and a C 6 to C 60 arylamine group, or an adjacent group forming a part of the fused ring,
Ar 1 to Ar 5 are each independently selected from the group consisting of a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 to C 60 aryloxy group, a C 6 to C 60 arylsilyl group, a C 6 to C 60 aryl boron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group and a C 6 to C 60 arylamine group, and
the C 1 to C 40 alkyl group, the C 6 to C 60 aryl group, the heteroaryl group having 5 to 60 nuclear atoms, the C 6 to C 60 aryloxy group, the C 6 to C 60 arylsilyl group, the C 6 to C 60 arylboron group, the C 6 to C 60 arylphosphine group, the C 6 to C 60 arylphosphine oxide group and the C 6 to C 60 arylamine group of R 1 to R 4 and Ar 1 to Ar 5 are optionally each independently unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 3 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 2 to C 40 alkylboron group, a C 6 to C 60 aryl boron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group and a C 6 to C 60 arylamine group.
2. The compound of claim 1 , wherein Ar 1 to Ar 5 are each independently selected from the group consisting of a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C 6 to C 60 arylamine group.
3. The compound of claim 1 , wherein R 1 to R 4 are each independently selected from the group consisting of a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C 6 to C 60 arylamine group.
4. The compound of claim 1 , wherein both X 1 and X 2 are N(Ar 1 ).
5. The compound of claim 1 , wherein the compound of Formulae 1a to 1f is selected from the group consisting of compounds of the following Formulae 5a to 5f:
in the formulae, R 1 , R 2 and Y 1 to Y 8 are the same as those defined in claim 1 ,
Z 1 to Z 5 are each independently N or CAr 6 ,
Ar 6 , A and B are each independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 3 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 2 to C 40 alkylboron group, a C 6 to C 60 aryl boron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group and a C 6 to C 60 arylamine group,
r and s are each an integer of 0 to 6, provided that r+s is at least 1 or more, and
p and q are each an integer of 0 to 3.
6. The compound of claim 5 , wherein Ar 6 , A and B are each independently selected from the group consisting of a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C 6 to C 60 arylamine group.
7. An organic elecroluminescent device comprising:
(i) an anode;
(ii) a cathode; and
(iii) an organic layer having one or more layers interposed between the anode and the cathode,
wherein at least one in the organic layer comprises the compound of claim 1 .
8. The organic electroluminescent device of claim 7 , wherein the organic layer comprising the compound is selected from the group consisting of a hole injection layer, a hole transporting layer, an electron injection layer, an electron transporting layer and a light-emitting layer.
9. The organic electroluminescent device of claim 6 , wherein the compound is a phosphorescent host of a light-emitting layer.