Organic compound and organic electroluminescent device comprising the same
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:
1. A compound of the following Chemical Formula 1:
wherein, in Chemical Formula 1,
L 1 is selected from the group consisting of a single bond, a C 6 ˜C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
Ar 1 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;
Z 1 , Z 3 and Z 5 are each independently N or C (R 8 ), wherein at least one of Z 1 , Z 3 and Z 5 is N;
o is an integer of 0 to 4;
R 8 to R 14 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 ˜C 40 alkyloxy group, a C 6 ˜C 60 aryloxy group, a C 3 ˜C 40 alkylsilyl group, a C 6 ˜C 60 arylsilyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 6 ˜C 60 arylphosphanyl group, a C 6 ˜C 60 mono or diarylphosphinyl group and a C 6 ˜C 60 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 R 8 , to R 14 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 C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 ˜C 60 aryloxy group, a C 1 ˜C 40 alkyloxy group, a C 6 ˜C 60 arylamine group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 1 ˜C 40 alkylsilyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 6 ˜C 60 arylphosphanyl group, a C 6 ˜C 60 mono or diarylphosphinyl group and a C 6 ˜C 60 arylsilyl group, and when substituted with a plurality of the substituents, these are the same as or different from each other;
any one of X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , and X 4 and X 5 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;
R 1 and R 2 are hydrogen;
X 1 to X 5 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 C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 ˜C 40 alkyloxy group, a C 6 ˜C 60 aryloxy group, a C 3 ˜C 40 alkylsilyl group, a C 6 ˜C 60 arylsilyl group, a C 1 ˜C 40 alkylsulfonyl group, a C 6 ˜C 60 arylsulfonyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 6 ˜C 60 arylphosphanyl group, a C 6 ˜C 60 mono or diarylphosphinyl group, a C 1 ˜C 40 alkylcarbonyl group, a C 6 ˜C 60 arylcarbonyl group and a C 6 ˜C 60 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 R 1 , R 2 , and X 1 to X 5 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 C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 ˜C 60 aryloxy group, a C 1 ˜C 40 alkyloxy group, a C 6 ˜C 60 arylamine group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 1 ˜C 40 alkylsilyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 6 ˜C 60 arylphosphanyl group, a C 6 ˜C 60 mono or diarylphosphinyl group and a C 6 ˜C 60 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;
R 3 is selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 ˜C 40 alkyloxy group, a C 6 ˜C 60 aryloxy group, a C 3 ˜C 40 alkylsilyl group, a C 6 ˜C 60 arylsilyl group, a C 1 ˜C 40 alkylsulfonyl group, a C 6 ˜C 60 arylsulfonyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 6 ˜C 60 arylphosphanyl group, a C 6 ˜C 60 mono or diarylphosphinyl group, a C 1 ˜C 40 alkylcarbonyl group, a C 6 ˜C 60 arylcarbonyl group and a C 6 ˜C 60 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 R 3 to R 6 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 C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 ˜C 60 aryloxy group, a C 1 ˜C 40 alkyloxy group, a C 6 ˜C 60 arylamine group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 1 ˜C 40 alkylsilyl group, a C 1 ˜C 40 alkylsulfonyl group, a C 6 ˜C 60 arylsulfonyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 6 ˜C 60 arylphosphanyl group, a C 6 ˜C 60 mono or diarylphosphinyl group, a C 1 ˜C 40 alkylcarbonyl group, a C 6 ˜C 60 arylcarbonyl group and a C 6 ˜C 60 arylsilyl group, and when substituted with a plurality of the substituents, these are the same as or different from each other.
2. A compound of the following Chemical Formula 1:
wherein in Chemical Formula 1,
L 1 is selected from the group consisting of a single bond, a C 6 ˜C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
any one of X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , and X 4 and X 5 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;
R 1 , R 2 , and X 1 to X 5 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 C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 ˜C 40 alkyloxy group, a C 6 ˜C 60 aryloxy group, a C 3 ˜C 40 alkylsilyl group, a C 6 ˜C 60 arylsilyl group, a C 1 ˜C 40 alkylsulfonyl group, a C 6 ˜C 60 arylsulfonyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 6 ˜C 60 arylphosphanyl group, a C 6 ˜C 60 mono or diarylphosphinyl group, a C 1 ˜C 40 alkylcarbonyl group, a C 6 ˜C 60 arylcarbonyl group and a C 6 ˜C 60 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 R 1 , R 2 , and X 1 to X 5 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 C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 ˜C 60 aryloxy group, a C 1 ˜C 40 alkyloxy group, a C 6 ˜C 60 arylamine group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 1 ˜C 40 alkylsilyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 6 ˜C 60 arylphosphanyl group, a C 6 ˜C 60 mono or diarylphosphinyl group and a C 6 ˜C 60 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;
Y 2 is O, S or C (R 5 ) (R 6 );
R 3 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 ˜C 40 alkyloxy group, a C 6 ˜C 60 aryloxy group, a C 3 ˜C 40 alkylsilyl group, a C 6 ˜C 60 arylsilyl group, a C 1 ˜C 40 alkylsulfonyl group, a C 6 ˜C 60 arylsulfonyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 6 ˜C 60 arylphosphanyl group, a C 6 ˜C 60 mono or diarylphosphinyl group, a C 1 ˜C 40 alkylcarbonyl group, a C 6 ˜C 60 arylcarbonyl group and a C 6 ˜C 60 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 R 3 , R 5 , and R 6 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 C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 ˜C 60 aryloxy group, a C 1 ˜C 40 alkyloxy group, a C 6 ˜C 60 arylamine group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 1 ˜C 40 alkylsilyl group, a C 1 ˜C 40 alkylsulfonyl group, a C 6 ˜C 60 arylsulfonyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 6 ˜C 60 arylphosphanyl group, a C 6 ˜C 60 mono or diarylphosphinyl group, a C 1 ˜C 40 alkylcarbonyl group, a C 6 ˜C 60 arylcarbonyl group and a C 6 ˜C 60 arylsilyl group, and when substituted with a plurality of the substituents, these are the same as or different from each other;
Ar 1 is a substituent represented by any one of the following Chemical Formula 13, Chemical Formula C-1 to Chemical Formula C-6,
Z 1 , Z 3 and Z 5 are each independently N or C (R 8 ), wherein at least one of Z 1 , Z 3 and Z 5 is N;
o is an integer of 0 to 4;
R 8 is selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 ˜C 40 alkyloxy group, a C 6 ˜C 60 aryloxy group, a C 3 ˜C 40 alkylsilyl group, a C 6 ˜C 60 arylsilyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 6 ˜C 60 arylphosphanyl group, a C 6 ˜C 60 mono or diarylphosphinyl group and a C 6 ˜C 60 arylamine group, or bonds to adjacent groups to form a fused ring, and when R 8 is present in plural numbers, these are the same as or different from each other; and R 9 and R 10 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 ˜C 40 alkyloxy group, a C 6 ˜C 60 aryloxy group, a C 3 ˜C 40 alkylsilyl group, a C 6 ˜C 60 arylsilyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 6 ˜C 60 arylphosphanyl group, a C 6 ˜C 60 mono or diarylphosphinyl group and a C 6 ˜C 60 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 R 8 and R 10 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 C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 ˜C 60 aryloxy group, a C 1 ˜C 40 alkyloxy group, a C 6 ˜C 60 arylamine group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 1 ˜C 40 alkylsilyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 6 ˜C 60 arylphosphanyl group, a C 6 ˜C 60 mono or diarylphosphinyl group and a C 6 ˜C 60 arylsilyl group, and when substituted with a plurality of the substituents, these are the same as or different from each other; and
R 11 and R 12 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 ˜C 40 alkyloxy group, a C 6 ˜C 60 aryloxy group, a C 3 ˜C 40 alkylsilyl group, a C 6 ˜C 60 arylsilyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 6 ˜C 60 arylphosphanyl group, a C 6 ˜C 60 mono or diarylphosphinyl group and a C 6 ˜C 60 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 R 11 and R 12 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 C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 ˜C 60 aryloxy group, a C 1 ˜C 40 alkyloxy group, a C 6 ˜C 60 arylamine group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 1 ˜C 40 alkylsilyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 6 ˜C 60 arylphosphanyl group, a C 6 ˜C 60 mono or diarylphosphinyl group and a C 6 ˜C 60 arylsilyl group, and when substituted with a plurality of the substituents, these are the same as or different from each other;
provided that when Ar 1 is represented by Chemical Formula C-1, R 12 is not hydrogen or deuterium;
provided that when Ar 1 is represented by Chemical Formula 13, compounds meet conditions that at least one of R 9 and R 10 is a heteroaryl group having 5 to 60 nuclear atoms, or that L 1 is a heteroarylene group having 5 to 18 nuclear atoms.
3. 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, R 1 to R 3 , L 1 and Ar 1 have the same definitions as in claim 1 .
4. The compound of claim 1 , wherein L 1 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.
5. The compound of claim 2 , wherein R 12 is selected from the group consisting of a C 1 ˜C 40 alkyl group, a C 6 ˜C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms; and
the alkyl group, the aryl group and the heteroaryl group of R 12 are each independently unsubstituted or substituted with one or more types of substituents selected from the group consisting of a C 1 ˜C 40 alkyl group, a C 6 ˜C 60 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.
6. The compound of claim 1 , wherein R 13 and R 14 are each independently selected from the group consisting of a C 1 ˜C 30 alkyl group, a C 6 ˜C 30 aryl group and a heteroaryl group having 5 to 30 nuclear atoms.
7. The compound of claim 1 , which is selected from the group consisting of the following compounds:
8. 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 .
9. 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.
10. 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;
L 1 , Ar 1 , q, m, n, R 1 , R 2 , and R 3 have the same definitions as in claim 2 .
11. The compound of claim 2 , which is selected from the group consisting of the following compounds:
12. 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 .