Compound, light-emitting material, and organic light-emitting device
A compound represented by the general formula (1) is useful as a light-emitting material. In the general formula (1), Ar 1 to Ar 3 represent an aryl group, provided that at least one thereof represents an aryl group substituted by a group represented by the general formula (2). In the general formula (2), R 1 to R 8 represent a hydrogen atom or a substituent; Z represents O, S, O═C or Ar 4 —N; and Ar 4 represents an aryl group.
1. A compound represented by the following general formula (1):
wherein in the general formula (1), Ar 1 to Ar 3 each independently represent a substituted or unsubstituted aryl group, provided that at least one thereof represents an aryl group substituted by a group represented by the following general formula (2):
wherein in the general formula (2), * represents the bonding site to the triazine ring in the general formula (1); R 1 to R 8 each independently represent a hydrogen atom or a substituent; Z represents O, S, O═C or Ar 4 —N; and Ar 4 represents a substituted or unsubstituted aryl group, provided that R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 each may be bonded to each other to form a cyclic structure, provided that neither Ar 2 nor Ar 3 is a phenyl group when Ar1 is a 4-(phenothiazin-10-yl)phenyl group, and
provided that when one of the Ar 1 to Ar 3 is an aryl group substituted with a group represented by the general formula (2) wherein Z is O, S or O═C, then at least one of the other Ar 1 to Ar 3 has a group represented by the general formula (2).
2. The compound according to claim 1 , wherein at least one of Ar 1 to Ar 3 in the general formula (1) represents an aryl group substituted by a group represented by the following general formula (3):
wherein in the general formula (3), * represents the bonding site to the triazine ring in the general formula (1); R 1 to R 8 each independently represent a hydrogen atom or a substituent, provided that R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 each may be bonded to each other to form a cyclic structure.
3. The compound according to claim 1 , wherein at least one of Ar 1 to Ar 3 in the general formula (1) represents an aryl group substituted by a group represented by the following general formula (4):
wherein in the general formula (4), * represents the bonding site to the triazine ring in the general formula (1); R 1 to R 8 each independently represent a hydrogen atom or a substituent, provided that R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 each may be bonded to each other to form a cyclic structure.
4. The compound according to claim 1 , wherein at least one of Ar 1 to Ar 3 in the general formula (1) represents an aryl group substituted by a group represented by the following general formula (5):
wherein in the general formula (5), * represents the bonding site to the triazine ring in the general formula (1); R 1 to R 8 each independently represent a hydrogen atom or a substituent, provided that R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 each may be bonded to each other to form a cyclic structure.
5. The compound according to claim 1 , wherein the compound has a structure represented by the following general formula (6):
wherein in the general formula (6), Ar 2 , Ar 3 , Ar 2 ′ and Ar 3 ′ each independently represent a substituted or unsubstituted aryl group; Ar 5 and Ar 5 ′ each independently represent a substituted or unsubstituted arylene group; and R 1 to R 8 each independently represent a hydrogen atom or a substituent, provided that R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 each may be bonded to each other to form a cyclic structure.
6. The compound according to claim 1 , wherein the compound has a structure represented by the following general formula (7):
wherein in the general formula (7), at least one of R 11 to R 25 represents a group represented by the general formula (2) below, and the other thereof each independently represent a hydrogen atom or a substituent other than the general formula (2), provided that R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 19 and R 20 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , and R 24 and R 25 each may be bonded to each other to form a cyclic structure:
wherein in the general formula (2), * represents the bonding site to the triazine ring in the general formula (1); R 1 to R 8 each independently represent a hydrogen atom or a substituent; Z represents O, S, O═C or Ar 4 —N; and Ar 4 represents a substituted or unsubstituted aryl group, provided that R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 each may be bonded to each other to form a cyclic structure.
7. The compound according to claim 6 , wherein at least one of R 11 to R 25 in the general formula (7) represents a group represented by the following general formula (3):
wherein in the general formula (3), * represents the bonding site to the triazine ring in the general formula (1); R 1 to R 8 each independently represent a hydrogen atom or a substituent, provided that R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 each may be bonded to each other to form a cyclic structure.
8. The compound according to claim 6 , wherein at least one of R 11 to R 25 in the general formula (7) represents a group represented by the following general formula (4):
wherein in the general formula (4), * represents the bonding site to the triazine ring in the general formula (1); R 1 to R 8 each independently represent a hydrogen atom or a substituent, provided that R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 each may be bonded to each other to form a cyclic structure.
9. The compound according to claim 6 , wherein at least one of R 11 to R 25 in the general formula (7) represents a group represented by the following general formula (5):
wherein in the general formula (5), * represents the bonding site to the triazine ring in the general formula (1); R 1 to R 8 each independently represent a hydrogen atom or a substituent, provided that R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 each may be bonded to each other to form a cyclic structure.
10. The compound according to claim 7 , wherein the compound has a rotationally symmetric structure with the center of the triazine ring as the axis.
11. The compound according to claim 6 , wherein the compound has a structure represented by the following general formula (8):
wherein in the general formula (8), R 1 to R 8 , R 11 , R 12 , R 14 to R 25 , R 11 ′, R 12 ′, and R 14 ′ to R 25 ′ each independently represent a hydrogen atom or a substituent, provided that R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 11 and R 12 , R 14 and R 15 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 19 and R 20 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 11′ and R 12′ , R 14′ and R 15′ , R 16′ and R 17′ , R 17′ and R 18′ , R 18′ and R 19′ , R 19′ and R 20′ , R 21′ and R 22′ , R 22′ and R 23′ , R 23′ and R 24′ , and R 24′ and R 25′ each may be bonded to each other to form a cyclic structure.
12. An organic light-emitting device containing a substrate having thereon a light-emitting layer that contains a host material and a light-emitting material containing a compound represented by the following general formula (1):
wherein in the general formula (1), Ar 1 to Ar 3 each independently represent a substituted or unsubstituted aryl group, provided that at least one thereof represents an aryl group substituted by a group represented by the following general formula (2):
wherein in the general formula (2), * represents the bonding site to the triazine ring in the general formula (1); R 1 to R 8 each independently represent a hydrogen atom or a substituent; Z represents O, S, O═C or Ar 4 —N; and Ar 4 represents a substituted or unsubstituted aryl group, provided that R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 each may be bonded to each other to form a cyclic structure, provided that neither Ar 2 nor Ar 3 is a phenyl group when Ar 1 is a 4-(phenothiazin-10-yl)phenyl group.
13. The organic light-emitting device according to claim 12 , wherein the device emits delayed fluorescent light.
14. The organic light-emitting device according to claim 12 , wherein the device is an organic electroluminescent device.