Nitrogen heterocycle fused ring-indene compound and organic light-emitting display device
The present disclosure relates to a nitrogen heterocycle fused ring-indene compound having a structure represented by the Formula (I), in which Ar 1 represents a substituted or unsubstituted aromatic fused ring group containing at least one nitrogen heteroaryl; Ar 2 represents a chemical group acting as an electron donor; R 1 and R 2 are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl. The compounds according to the present disclosure have high glass transition temperature and thermal stability, and are easy to form a high-quality amorphous film, so that a driving voltage can be lowered, the luminous efficiency and lifetime of the device are improved.
1. A nitrogen heterocycle fused ring-indene compound being any one of following compounds:
wherein
Ar 2 is an electron donor; and
R 1 and R 2 are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl.
2. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein R 1 and R 2 are each methyl.
3. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein Ar 2 is selected from the group consisting of substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silicylene, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl.
4. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein Ar 2 is any one of following groups:
wherein m, n and p are integers independently selected from 0, 1, 2 and 3;
U 1 , U 2 and U 3 are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silicylene, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C10-C 30 fused aryl; and
# indicates a bonding position to which a benzene ring in the compounds I-2, I-3, I-5, or I-6 is bonded.
5. The nitrogen heterocycle fused ring-indene compound according to claim 4 , wherein Ar 2 is any one of following groups:
wherein R is selected from the group consisting of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silicylene, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C10-C30 fused aryl.
6. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein Ar 2 is any one of following groups:
wherein Z is selected from a group consisting of carbon atom, nitrogen atom, oxygen atom, sulfur atom, and silicon atom;
q is an integer selected from 0, 1, 2 and 3;
U 4 is selected from the group consisting of hydrogen atom, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silicylene, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C10-C30 fused aryl;
when Z is oxygen or sulfur, q=0; and
# indicates a bonding position to which a benzene ring in the compounds I-2, I-3, I-5, or I-6 is bonded.
7. The nitrogen heterocycle fused ring-indene compound according to claim 6 , wherein Ar 2 is any one of following groups:
8. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein Ar2 is any one of following groups:
wherein Z is selected from the group consisting of carbon, nitrogen, oxygen, sulfur, and silicon;
X is selected from the group consisting of carbon, nitrogen, oxygen, and sulfur;
m, n, p and q are integers independently selected from 0, 1, 2 and 3;
U 1 , U 2 , U 3 and U 4 are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silicylene, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C10-C30 fused aryl;
when Z or X is oxygen or sulfur, p or q is 0; and
# indicates a bonding position to which a benzene ring in the compounds I-2, I-3, I-5, or I-6 is bonded.
9. The nitrogen heterocycle fused ring-indene compound according to claim 8 , wherein Ar 2 is any one of following groups:
wherein R is selected from the group consisting of hydrogen atom, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl.
10. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein Ar 2 is any one of following groups:
wherein X is selected from the group consisting of oxygen atom, sulfur atom, and silicon atom;
m and n are integers independently selected from 0, 1, 2 and 3;
U 1 and U 2 are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silicylene, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C10-C30 fused aryl; and
# indicates a bonding position to which a benzene ring in the compounds I-2, I-3, I-5, or I-6 is bonded.
11. The nitrogen heterocycle fused ring-indene compound according to claim 10 , wherein Ar 2 is any one of following groups:
12. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein Ar 2 is any one of following groups:
wherein R is selected from the group consisting of hydrogen atom, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl.
13. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein the nitrogen heterocycle fused ring-indene compound is any one of following compounds:
14. An organic light-emitting display device, comprising
an anode;
a cathode; and
a light-emitting layer disposed between the anode and the cathode,
wherein a host material or a guest material of the light-emitting layer is selected from the group consisting of nitrogen heterocycle fused ring-indene compounds, and combinations thereof, the nitrogen heterocycle fused ring-indene compound is any one of following compounds:
wherein
Ar 2 is an electron donor; and
R 1 and R 2 are independently selected from the group consisting of hydrogen atom, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl.
15. The organic light-emitting display device according to claim 14 , wherein Ar 2 is selected from the group consisting of substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silicylene, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl.
16. The organic light-emitting display device according to claim 14 , wherein Ar 2 is any one of following groups:
wherein m, n and p are integers independently selected from 0, 1, 2 and 3;
U 1 , U 2 and U 3 are independently selected from the group consisting of hydrogen atom, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silicylene, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C10-C30 fused aryl; and
# indicates a bonding position to which a benzene ring in the compounds I-2, I-3, I-5, or I-6 is bonded.
17. The organic light-emitting display device according to claim 14 , further comprising a hole injection layer, a hole transmission layer, an electron blocking layer, a hole blocking layer, an electron transmission layer, an electron injection layer, or any combination thereof.
18. The organic light-emitting display device according to claim 17 , wherein the electron transmission layer or the hole transmission layer is made of a material selected from the group consisting of nitrogen heterocycle fused ring-indene compounds, and combinations thereof, the nitrogen heterocycle fused ring-indene compounds is any one of following compounds:
wherein
Ar 2 is an electron donor; and
R 1 and R 2 are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl.