Compound and organic light emitting device comprising same
Provided is a compound of Formula 1: and an organic light emitting device including the same.
1. A compound of Formula 1:
wherein in Formula 1:
X1 and X2 are the same as or different from each other, and are each independently —O—, —S—, —C(R7R8)-, or —N(R9);
at least two of R1 to R4 are the same as or different from each other, and are each independently a group of the following Formula A;
groups which are not the following Formula A among R1 to R4 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
R5 and R6 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring;
R7 to R9 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
a and b are each an integer from 1 to 4;
when a and b are each 2 or more, two or more structures in the parenthesis are the same as or different from each other:
wherein in Formula A:
L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group;
Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or are optionally bonded to each other to form a substituted or unsubstituted ring;
m is an integer from 1 to 5;
when m is 2 or more, two or more L1's are the same as or different from each other; and
is a moiety bonded to Formula 1.
2. The compound of claim 1 , wherein Formula 1 is any one of the following Formulae 1-1 to 1-3:
wherein in Formulae 1-1 to 1-3:
the definitions of X1, X2, and R1 to R4 are the same as those defined in Formula 1;
R5, R6, R51, and R61 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
a1 and b1 are each 1 or 2;
r51 and r61 are each an integer from 1 to 4;
when a1 and b1 are each 2, the structures in the parenthesis are the same as or different from each other; and
when r51 and r61 are each 2 or more, two or more structures in the parenthesis are the same as or different from each other.
3. The compound of claim 1 , wherein Formula 1 is any one of the following Formulae 1-4 to 1-7:
wherein in Formulae 1-4 to 1-7:
the definitions of X1, X2, R5, R6, a, and b are the same as those defined in Formula 1;
R1 and R2 are the same as or different from each other, and are each independently a group of Formula A; and
R3 and R4 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
4. The compound of claim 1 , wherein Formula 1 is any one of the following Formulae 1-9 to 1-12:
wherein in Formulae 1-9 to 1-12:
the definitions of X1, X2, R5, R6, a, and b are the same as those defined in Formula
the definitions of L1, m, Ar1, and Ar2 are the same as those defined in Formula A;
R3 and R4 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
L11 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group;
Ar11 and Ar12 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or are optionally bonded to each other to form a substituted or unsubstituted ring;
m1 is an integer from 1 to 5; and
when m1 is 2 or more, two or more L11's are the same as or different from each other.
5. The compound of claim 1 , wherein L1 is a direct bond or an arylene group.
6. The compound of claim 1 , wherein Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group which is unsubstituted or substituted with a halogen group, an alkyl group, or an aryl group; or a heteroaryl group which is unsubstituted or substituted with an alkyl group or an aryl group.
7. The compound of claim 1 , wherein the compound of Formula 1 is selected from among the following compounds:
Com-
R3 to
pound
X1
X2
R1
R2
R6
1-1
O
O
H
1-2
O
O
H
1-3
O
O
H
1-4
O
O
H
1-5
O
O
H
1-6
O
O
H
1-7
O
O
H
1-8
O
O
H
1-9
O
O
H
1-10
O
O
H
1-11
O
O
H
1-12
O
O
H
1-13
O
O
H
1-14
O
O
H
1-15
O
O
H
1-16
O
O
H
1-17
O
O
H
1-18
O
O
H
1-19
O
O
H
1-20
O
O
H
1-21
O
O
H
1-22
O
O
H
1-23
O
O
H
Com-
R3 to
pound
X1
X2
R1
R2
to R6
2-1
S
S
H
2-2
S
S
H
2-3
S
S
H
2-4
S
S
H
2-5
S
S
H
2-6
S
S
H
2-7
S
S
H
2-8
S
S
H
2-9
S
S
H
2-10
S
S
H
2-11
S
S
H
2-12
S
S
H
2-13
S
S
H
2-14
S
S
H
2-15
S
S
H
2-16
S
S
H
2-17
S
S
H
2-18
S
S
H
2-19
S
S
H
2-20
S
S
H
2-21
S
S
H
2-22
S
S
H
R3
Com-
to
pound
X1
X2
R1
R2
R6
3-1
H
3-2
H
3-3
H
3-4
H
3-5
H
3-6
H
3-7
H
3-8
H
3-9
H
3-10
H
3-11
H
3-12
H
3-13
H
3-14
H
3-15
H
3-16
H
3-17
H
3-18
H
3-19
H
3-20
H
Compound
X1
X2
R1
4-1
4-2
4-3
4-4
4-5
4-6
4-7
4-8
4-9
4-10
4-11
4-12
4-13
4-14
4-15
4-16
4-17
4-18
4-19
4-20
4-21
Compound
R2
R3 to R6
4-1
H
4-2
H
4-3
H
4-4
H
4-5
H
4-6
H
4-7
H
4-8
H
4-9
H
4-10
H
4-11
H
4-12
H
4-13
H
4-14
H
4-15
H
4-16
H
4-17
H
4-18
H
4-19
H
4-20
H
4-21
H
Compound
X
Y
R1
5-1
5-2
5-3
5-4
5-5
5-6
5-7
5-8
5-9
5-10
5-11
5-12
5-13
5-14
5-15
5-16
5-17
5-18
5-19
5-20
5-21
Compound
R2
R3 to R6
5-1
H
5-2
H
5-3
H
5-4
H
5-5
H
5-6
H
5-7
H
5-8
H
5-9
H
5-10
H
5-11
H
5-12
H
5-13
H
5-14
H
5-15
H
5-16
H
5-17
H
5-18
H
5-19
H
5-20
H
5-21
H
Compound
X
Y
R1
6-1
6-2
6-3
6-4
6-5
6-6
6-7
6-8
6-9
6-10
6-11
6-12
6-13
6-14
6-15
6-16
6-17
6-18
6-19
6-20
6-21
Compound
R2
R3 to R6
6-1
H
6-2
H
6-3
H
6-4
H
6-5
H
6-6
H
6-7
H
6-8
H
6-9
H
6-10
H
6-11
H
6-12
H
6-13
H
6-14
H
6-15
H
6-16
H
6-17
H
6-18
H
6-19
H
6-20
H
6-21
H
Compound
X1
X2
R1
7-1
O
S
7-2
O
7-3
O
7-4
O
7-5
O
7-6
S
7-7
S
7-8
S
7-9
S
7-10
7-11
7-12
7-13
7-14
7-15
7-16
O
S
7-17
O
7-18
O
7-19
O
7-20
O
Compound
R2
R3 to R6
7-1
H
7-2
H
7-3
H
7-4
H
7-5
H
7-6
H
7-7
H
7-8
H
7-9
H
7-10
H
7-11
H
7-12
H
7-13
H
7-14
H
7-15
H
7-16
H
7-17
H
7-18
H
7-19
H
7-20
H
Compound
X1
X2
R1
8-1
O
O
8-2
O
O
8-3
O
O
8-4
O
O
8-5
O
O
8-6
O
O
8-7
O
O
8-8
O
O
8-9
O
O
8-10
O
O
8-11
O
O
8-12
O
O
8-13
O
O
8-14
O
O
8-15
O
O
8-16
O
O
8-17
O
O
8-18
O
O
8-19
O
O
8-20
O
O
Compound
R2
R3 to R6
8-1
8-2
8-3
8-4
8-5
8-6
8-7
8-8
8-9
8-10
8-11
8-12
8-13
8-14
8-15
8-16
8-17
8-18
8-19
8-20
Com-
pound
X1
X2
R1
R2
R3 to R6
9-1
S
S
—CH 3
9-2
S
S
—CH 3
9-3
S
S
—CH 3
9-4
S
S
—CH 3
9-5
S
S
—CH 3
9-6
S
S
—CH 3
9-7
S
S
—CH 3
9-8
S
S
—CH 3
9-9
S
S
—CH 3
9-10
S
S
—CH 3
9-11
S
S
—CH 3
9-12
S
S
—CH 3
9-13
S
S
—CH 3
9-14
S
S
—CH 3
9-15
S
S
—CH 3
9-16
S
S
—CH 3
9-17
S
S
—CH 3
9-18
S
S
—CH 3
9-19
S
S
—CH 3
9-20
S
S
—CH 3
Compound
X1
X2
R1
10-1
10-2
10-3
10-4
10-5
10-6
10-7
10-8
10-9
10-10
10-11
10-12
10-13
10-14
10-15
10-16
10-17
10-18
10-19
10-20
Compound
R2
R3 to R6
10-1
10-2
10-3
10-4
10-5
10-6
10-7
10-8
10-9
10-10
10-11
10-12
10-13
10-14
10-15
10-16
10-17
10-18
10-19
10-20
Compound
X1
X2
R1
11-1
11-2
11-3
11-4
11-5
11-6
11-7
11-8
11-9
11-10
11-11
11-12
11-13
11-14
11-15
11-16
11-17
11-18
11-19
11-20
Compound
R2
R3 to R6
11-1
11-2
11-3
11-4
11-5
11-6
11-7
11-8
11-9
11-10
11-11
11-12
11-13
11-14
11-15
11-16
11-17
11-18
11-19
11-20
Compound
X
X
R1
12-1
12-2
12-3
12-4
12-5
12-6
12-7
12-8
12-9
12-10
12-11
12-12
12-13
12-14
12-15
12-16
12-17
12-18
12-19
12-20
Compound
R2
R3 to R6
12-1
12-2
12-3
12-4
12-5
12-6
12-7
12-8
12-9
12-10
12-11
12-12
12-13
12-14
12-15
12-16
12-17
12-18
12-19
12-20
Compound
X
X
R1
13-1
13-2
13-3
13-4
13-5
13-6
13-7
13-8
13-9
13-10
13-11
13-12
13-13
13-14
13-15
13-16
13-17
13-18
13-19
13-20
Compound
R2
R3 to R6
13-1
13-2
13-3
13-4
13-5
13-6
13-7
13-8
13-9
13-10
13-11
13-12
13-13
13-14
13-15
13-16
13-17
13-18
13-19
13-20
Compound
X
X
R1
14-1
O
S
14-2
O
14-3
O
14-4
O
14-5
O
14-6
S
14-7
S
14-8
S
14-9
S
14-10
14-11
14-12
14-13
14-14
14-15
14-16
O
S
14-17
O
14-18
O
14-19
O
14-20
O
Compound
R2
R3 to R6
14-1
14-2
14-3
14-4
14-5
14-6
14-7
14-8
14-9
14-10
14-11
14-12
14-13
14-14
14-15
14-16
14-17
14-18
14-19
14-20
8. An organic light emitting device comprising:
a first electrode;
a second electrode provided to face the first electrode; and
an organic material layer having one or more layers provided between the first electrode and the second electrode,
wherein one or more layers of the organic material layer comprise the compound of claim 1 .
9. The organic light emitting device of claim 8 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the compound.
10. The organic light emitting device of claim 8 , wherein the organic material layer comprises a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound.
11. The organic light emitting device of claim 8 , wherein the organic material layer comprises an electron injection layer, an electron transport layer, or a layer which injects and transports electrons simultaneously, and the electron injection layer, the electron transport layer, or the layer which injects and transports electrons simultaneously comprises the compound.
12. The organic light emitting device of claim 8 , wherein the organic material layer comprises an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the compound.
13. The organic light emitting device of claim 8 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises a compound of Formula 1A:
wherein in Formula 1A:
L103 and L104 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group;
Ar5 and Ar6 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; and
R101 to R108 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
14. The organic light emitting device of claim 13 , wherein L103 and L104 are the same as or different from each other, and are each independently selected from the substituents in the following Table 1, and Ar5 and Ar6 are the same as or different from each other, and are each independently selected from the substituents in the following Table 2:
TABLE 1
Substituent A1
Substituent A2
Substituent A3
Substituent A4
Substituent A5
Substituent A6
Substituent A7
Substituent A8
Substituent A9
Substituent A10
Substituent A11
Substituent A12
Substituent A13
Substituent A14
Substituent A15
TABLE 2
Substituent B1
Substituent B2
Substituent B3
Substituent B4
Substituent B5
Substituent B6
Substituent B7
Substituent B8
Substituent B9
Substituent B10
Substituent B11
Substituent B12
Substituent B13
Substituent B14
Substituent B15
Substituent B16
Substituent B17
Substituent B18
Substituent B19
Substituent B20
Substituent B21
Substituent B22
Substituent B23
Substituent B24
Substituent B25
Substituent B26
Substituent B27
Substituent B28
Substituent B29
Substituent B30
Substituent B31
Substituent B32
Substituent B33
Substituent B34
Substituent B35
Substituent B36
Substituent B37
Substituent B38
Substituent B39
Substituent B40
Substituent B41
Substituent B42
Substituent B43
Substituent B44
Substituent B45
Substituent B46
Substituent B47
Substituent B48
Substituent B49
Substituent B50
Substituent B51
Substituent B52
Substituent B53
Substituent B54
Substituent B55
Substituent B56
15. The organic light emitting device of claim 8 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises a compound of Formula 1B:
wherein in Formula 1B:
L105 to L107 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group;
Ar7 to Ar9 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; and
R109 to R115 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
16. The organic light emitting device of claim 15 , wherein L105 to L107 are the same as or different from each other, and are each independently selected from the substituents in the following Table 3, and Ar7 to Ar9 are the same as or different from each other, and are each independently selected from the substituents in the following Table 4:
TABLE 3
Substituent A1
Substituent A2
Substituent A3
Substituent A4
Substituent A5
Substituent A6
Substituent A7
Substituent A8
Substituent A9
Substituent A10
Substituent A11
Substituent A12
Substituent A13
Substituent A14
Substituent A15
TABLE 4
Substituent B1
Substituent B2
Substituent B3
Substituent B4
Substituent B5
Substituent B6
Substituent B7
Substituent B8
Substituent B9
Substituent B10
Substituent B11
Substituent B12
Substituent B13
Substituent B14
Substituent B15
Substituent B16
Substituent B17
Substituent B18
Substituent B19
Substituent B20
Substituent B21
Substituent B22
Substituent B23
Substituent B24
Substituent B25
Substituent B26
Substituent B27
Substituent B28
Substituent B29
Substituent B30
Substituent B31
Substituent B32
Substituent B33
Substituent B34
Substituent B35
Substituent B36
Substituent B37
Substituent B38
Substituent B39
Substituent B40
Substituent B41
Substituent B42
Substituent B43
Substituent B44
Substituent B45
Substituent B46
Substituent B47
Substituent B48
Substituent B49
Substituent B50
Substituent B51
Substituent B52
Substituent B53
Substituent B54
Substituent B55
Substituent B56
17. The organic light emitting device of claim 8 , wherein the organic light emitting device further comprises one or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.