IP Library Granted Patent US 10,236,451
Granted Patent B2
US 10,236,451 · App. 14/413,575 · Granted Mar 19, 2019

Compound and organic electroluminescent device comprising the same

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Quick Facts
Patent No.
US 10,236,451
App. No.
14/413,575
Granted
Mar 19, 2019
Kind
B2
Abstract

Disclosed is a novel benzimidazole compound having excellent hole injection and transport capabilities, light-emitting capabilities, and the like, and an organic electroluminescent device which comprises the benzimidazole compound in one or more organic material layers thereof so as to thereby achieve enhanced characteristics, such as light-emitting efficiency, driving voltage, and lifespan.

Claims (63)

1. A compound of the Formula selected from the group consisting of the following Formulae 9 to 12:

in Formulae 9 to 12,

X 1 is selected from the group consisting of NR 1 , O, S, Se, SiR 2 R 3 , and CR 4 R 5 ;

X 2 is N or CR 6 ;

Y 1 to Y 4 are each independently N or CR 7 , and in this case, a plurality of CR 7 's are the same as or different from each other;

R 1 to R 7 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C 1 to C 40 alkyloxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 1 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C 60 arylsilyl group, a substituted or unsubstituted C 1 to C 40 alkylboron group, a substituted or unsubstituted C 6 to C 60 arylboron group, a substituted or unsubstituted C 6 to C 60 arylphosphine group, a substituted or unsubstituted C 6 to C 60 arylphosphine oxide group, and a substituted or unsubstituted C 6 to C 60 arylamine group, or may be fused with an adjacent group to form a fused ring, and

in this case, the alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group and the arylamine group of R 1 to R 7 may be each independently substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, 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 6 to C 60 arylborane group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron 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;

X 3 is selected from the group consisting of O, S, Se, N(Ar 1 ), C(Ar 2 )(Ar 3 ), and Si(Ar 4 )(Ar 5 ), with the proviso that in Formula 10, X 3 is not S, and in this case, a plurality of X 3 's are the same as or different from each other;

Ar 1 to Ar 5 are each independently selected from the group consisting of a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C 1 to C 40 alkyloxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 3 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C 60 arylsilyl group, a substituted or unsubstituted C 1 to C 40 alkylboron group, a substituted or unsubstituted C 6 to C 60 arylboron group, a substituted or unsubstituted C 6 to C 60 arylphosphine group, a substituted or unsubstituted C 6 to C 60 arylphosphine oxide group, and a substituted or unsubstituted C 6 to C 60 arylamine group, and

the alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, and the arylamine group of Ar 1 to Ar 5 may be each independently substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, 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 6 to C 60 arylborane group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron 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;

Y 5 to Y 8 are each independently N or CR 8 , and in this case, a plurality of CR 8 's is the same as or different from each other;

R 8 is selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C 1 to C 40 alkyloxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 1 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C 60 arylsilyl group, a substituted or unsubstituted C 1 to C 40 alkylboron group, a substituted or unsubstituted C 6 to C 60 arylboron group, a substituted or unsubstituted C 6 to C 60 arylphosphine group, a substituted or unsubstituted C 6 to C 60 arylphosphine oxide group, and a substituted or unsubstituted C 6 to C 60 arylamine group, or may be fused with an adjacent group to form a fused ring, and

the alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, and the arylamine group of R 8 may be each independently substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, 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 6 to C 60 arylborane group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron 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. A compound of the formula selected from the group consisting of the following Formulae 3 to 8:

in Formula 3 to 8,

X 1 is selected from the group consisting of NR 1 , O, S, Se, SiR 2 R 3 , and CR 4 R 5 ;

X 2 is N or CR 6 ;

X 3 is N(Ar 1 );

Y 1 to Y 4 are each independently N or CR 7 , and in this case, a plurality of CR 7 's are the same as or different from each other,

R 1 to R 7 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C 1 to C 40 alkyloxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 1 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C 60 arylsilyl group, a substituted or unsubstituted C 1 to C 40 alkylboron group, a substituted or unsubstituted C 6 to C 60 arylboron group, a substituted or unsubstituted C 6 to C 60 arylphosphine group, a substituted or unsubstituted C 6 to C 60 arylphosphine oxide group, and a substituted or unsubstituted C 6 to C 60 arylamine group, or may be fused with an adjacent group to form a fused ring, with the proviso that in Formulae 4, R 6 is not hydrogen, cyano, and an unsubstituted C 1 to C 40 alkyl group, and that in Formulae 5, R 6 is not hydrogen and cyano;

Ar 1 is selected from the group consisting of a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C 1 to C 40 alkyloxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 3 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C 60 arylsilyl group, a substituted or unsubstituted C 1 to C 40 alkylboron group, a substituted or unsubstituted C 6 to C 60 arylboron group, a substituted or unsubstituted C 6 to C 60 arylphosphine group, a substituted or unsubstituted C 6 to C 60 arylphosphine oxide group, and a substituted or unsubstituted C 6 to C 60 arylamine group;

Y 5 to Y 8 are each independently N or CR 8 , and in this case, a plurality of CR 8 's are the same as or different from each other;

R 8 is selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C 1 to C 40 alkyloxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 1 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C 60 arylsilyl group, a substituted or unsubstituted C 1 to C 40 alkylboron group, a substituted or unsubstituted C 6 to C 60 arylboron group, a substituted or unsubstituted C 6 to C 60 arylphosphine group, a substituted or unsubstituted C 6 to C 60 arylphosphine oxide group, and a substituted or unsubstituted C 6 to C 60 arylamine group; and

the alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, and the arylamine group of R 1 to R 8 and Ar 1 may be each independently substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, 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 6 to C 60 arylborane group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron 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.

3. The compound as claimed in claim 1 , wherein X 3 is N(Ar 1 ), and Ar 1 is the same as that defined in claim 1 .

4. The compound as claimed in claim 1 , wherein X 1 is NR 1 , X 3 is N(Ar 1 ), and R 1 and Ar 1 are each the same as that defined in claim 1 .

5. The compound as claimed in claim 1 , wherein R 1 to R 8 and Ar 1 to Ar 5 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, and a substituted or unsubstituted C 6 to C 60 arylamine group; and

the alkyl group, the aryl group, the heteroaryl group, and the arylamine group of R 1 to R 8 and Ar 1 to Ar 5 may be substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, 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 6 to C 60 arylborane group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron 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.

6. The compound as claimed in claim 1 , wherein R 1 to R 8 and Ar 1 to Ar 5 are each independently selected from the group consisting of hydrogen, and the following substituents A1 to A40:

7. An organic electroluminescent device comprising:

an anode;

a cathode; and

one or more organic material layers interposed between the anode and the cathode,

wherein at least one of the organic material layers comprises a compound the formula selected from the group consisting of the following Formulae 9 to 12:

in Formulae 9 to 12,

X 1 is selected from the group consisting of NR 1 , O, S, Se, SiR 2 R 3 , and CR 4 R 5 ;

X 2 is N or CR 6 ;

Y 1 to Y 4 are each independently N or CR 7 , and in this case, a plurality of CR 7 's are the same as or different from each other;

R 1 to R 7 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C 1 to C 40 alkyloxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 1 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C 60 arylsilyl group, a substituted or unsubstituted C 1 to C 40 alkylboron group, a substituted or unsubstituted C 6 to C 60 arylboron group, a substituted or unsubstituted C 6 to C 60 arylphosphine group, a substituted or unsubstituted C 6 to C 60 arylphosphine oxide group, and a substituted or unsubstituted C 6 to C 60 arylamine group, or may be fused with an adjacent group to form a fused ring, and

in this case, the alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group and the arylamine group of R 1 to R 7 may be each independently substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, 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 6 to C 60 arylborane group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron 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;

X 3 is selected from the group consisting of O, S, Se, N(Ar 1 ), C(Ar 2 )(Ar 3 ), and Si(Ar 4 )(Ar 5 ), and in this case, a plurality of X 3 's are the same as or different from each other;

Ar 1 to Ar 5 are each independently selected from the group consisting of a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C 1 to C 40 alkyloxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 3 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C 60 arylsilyl group, a substituted or unsubstituted C 1 to C 40 alkylboron group, a substituted or unsubstituted C 6 to C 60 arylboron group, a substituted or unsubstituted C 6 to C 60 arylphosphine group, a substituted or unsubstituted C 6 to C 60 arylphosphine oxide group, and a substituted or unsubstituted C 6 to C 60 arylamine group, and

the alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, and the arylamine group of Ar 1 to Ar 5 may be each independently substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, 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 6 to C 60 arylborane group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron 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;

Y 5 to Y 8 are each independently N or CR 8 , and in this case, a plurality of CR 8 's are the same as or different from each other;

R 8 is selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C 1 to C 40 alkyloxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 1 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C 60 arylsilyl group, a substituted or unsubstituted C 1 to C 40 alkylboron group, a substituted or unsubstituted C 6 to C 60 arylboron group, a substituted or unsubstituted C 6 to C 60 arylphosphine group, a substituted or unsubstituted C 6 to C 60 arylphosphine oxide group, and a substituted or unsubstituted C 6 to C 60 arylamine group, or may be fused with an adjacent group to form a fused ring, and

the alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, and the arylamine group of R 8 may be each independently substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, 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 6 to C 60 arylborane group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron 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.

8. The organic electroluminescent device as claimed in claim 7 , wherein the one or more organic material layers, which comprise the compound, are selected from the group consisting of a hole injection layer, a hole transporting layer, and a light-emitting layer.

9. The organic electroluminescent device as claimed in claim 8 , wherein the compound is a host of the light-emitting layer.

10. An organic electroluminescent device comprising:

an anode;

a cathode; and

one or more organic material layers interposed between the anode and the cathode,

wherein at least one of the organic material layers comprises a compound of the formula selected from the group consisting of the following Formulae 3 to 8:

in Formulae 3 to 8,

X 1 is selected from the group consisting of NR 1 , O, S, Se, SiR 2 R 3 , and CR 4 R 5 ;

X 2 is N or CR 6 ;

X 3 is N(Ar 1 );

Y 1 to Y 4 are each independently N or CR 7 , and in this case, a plurality of CR 7 's are the same as or different from each other,

R 1 to R 7 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C 1 to C 40 alkyloxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 1 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C 60 arylsilyl group, a substituted or unsubstituted C 1 to C 40 alkylboron group, a substituted or unsubstituted C 6 to C 60 arylboron group, a substituted or unsubstituted C 6 to C 60 arylphosphine group, a substituted or unsubstituted C 6 to C 60 arylphosphine oxide group, and a substituted or unsubstituted C 6 to C 60 arylamine group, or may be fused with an adjacent group to form a fused ring;

Ar 1 is selected from the group consisting of a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C 1 to C 40 alkyloxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 3 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C 60 arylsilyl group, a substituted or unsubstituted C 1 to C 40 alkylboron group, a substituted or unsubstituted C 6 to C 60 arylboron group, a substituted or unsubstituted C 6 to C 60 arylphosphine group, a substituted or unsubstituted C 6 to C 60 arylphosphine oxide group, and a substituted or unsubstituted C 6 to C 60 arylamine group;

Y 5 to Y 8 are each independently N or CR 8 , and in this case, a plurality of CR 8 's are the same as or different from each other;

R 8 is selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C 1 to C 40 alkyloxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 1 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C 60 arylsilyl group, a substituted or unsubstituted C 1 to C 40 alkylboron group, a substituted or unsubstituted C 6 to C 60 arylboron group, a substituted or unsubstituted C 6 to C 60 arylphosphine group, a substituted or unsubstituted C 6 to C 60 arylphosphine oxide group, and a substituted or unsubstituted C 6 to C 60 arylamine group; and

the alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, and the arylamine group of R 1 to R 8 and Ar 1 may be each independently substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, 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 6 to C 60 arylborane group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron 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.

Assignments (4)
CHANGE OF NAME Recorded Jan 4, 2021
From: DOOSAN SOLUS CO., LTD.
To: SOLUS ADVANCED MATERIALS CO., LTD.
Reel/Frame 054887/0911 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 18, 2020
From: DOOSAN CORPORATION
To: DOOSAN SOLUS CO., LTD.
Reel/Frame 052970/0277 →
CHANGE OF ADDRESS Recorded Jun 18, 2020
From: DOOSAN CORPORATION
To: DOOSAN CORPORATION
Reel/Frame 052971/0480 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 21, 2015
From: BAE, HYUNG CHAN; BEAK, YOUNG MI; KIM, TAE HYUNG; PARK, HO CHEOL; LEE, CHANG JUN; SHIN, JIN YOUNG
To: DOOSAN CORPORATION
Reel/Frame 035693/0203 →