Organic electroluminescent element, compound, and light emitting device, display device and lighting system, using said element
An organic electroluminescent element including a substrate, a pair of electrodes including an anode and a cathode, disposed on the substrate, and at least one organic layer including a light emitting layer, disposed between the electrodes, in which at least one kind of compound represented by the following general formula is contained in any layer of the at least one organic layer, is an organic electroluminescent element, in which the generation of dark spots during driving is inhibited: wherein Q, Ar, L, and n are as defined in the application.
1. An organic electroluminescent element comprising:
a substrate;
a pair of electrodes including an anode and a cathode, disposed on the substrate; and
at least one organic layer including a light emitting layer, disposed between the electrodes,
wherein at least one kind of compound represented by the following general formula (II) is contained in any layer of the at least one organic layer;
wherein: R 1 to R 10 represent a hydrogen atom or a substituent, three out of the combinations of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 and R 10 and R 1 are substituted with each independent groups represented by the following general formula B, provided that at least one of the combinations of R 3 and R 4 , R 5 and R 6 , R 8 and R 9 , and R 10 and R 1 are substituted with the general formula B:
wherein L 2 represents CR 12 R 13 , NR 14 , SiR 15 R 16 , an O atom, or an S atom, wherein R 12 , R 13 , R 14 , R 15 and R 16 each independently represents a fluorine atom, an alkyl group, an aryl group, or a heteroaryl group; * and # represent sites for substitution with any one of the combinations of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 or R 10 and R 1 in the general formula (II), one of two groups in the combinations may be substituted at * or the other may be substituted at #; R 21 's each independently represents a substituent; o represents an integer of 0 to 4; where in the case where o is 2 to 4, the respective R 21 's may be the same as or different from each other, and R 21 's may be bonded to each other to form a ring.
2. The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (II) is a compound represented by the following general formula (III):
wherein: L 31 , L 32 , L 33 and L 34 each independently represents CR 12 R 13 , NR 14 , SiR 15 R 16 , an O atom, or an S atom, wherein (R 12 , R 13 , R 14 , R 15 and R 16 each independently represents a fluorine atom, an alkyl group, an aryl group, or a heteroaryl group; m1 and n1 are each 0 or 1, satisfying m1+n1=1; R 31 , R 32 and R 33 each independently represents a substituent; p1, q1 and r1 each independently represents an integer of 0 to 4; where in the case where p1, q1 and r1 are each 2 to 4, R 31 , R 32 and R 33 may be the same as or different from each other, and R 31 's, R 32 's, or R 33 's may be bonded to each other to form a ring.
3. The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (II) is a compound represented by the following general formula (IV):
wherein: L 41 , L 42 , L 43 and L 44 each independently represents CR 12 R 13 , NR 14 , SiR 15 R 16 , an O atom, or an S atom, wherein (R 12 , R 13 , R 14 , R 15 and R 16 each independently represents a fluorine atom, an alkyl group, an aryl group, or a heteroaryl group; m2 and n2 are each 0 or 1, satisfying m2+n2=1; R 41 , R 42 and R 43 each independently represents a substituent; p2, q2 and r2 each independently represents an integer of 0 to 4; where in the case where p2, q2 and r2 are each 2 to 4, R 41 , R 42 , R 43 may be the same as or different from each other, and R 41 's, R 42 's, or R 43 's may be bonded to each other to form a ring.
4. The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (II) is a compound represented by the following general formula (V):
wherein: L 51 , L 52 , L 53 and L 54 each independently represents CR 12 R 13 , NR 14 , SiR 15 R 16 , anl O atom, or an S atom, wherein R 12 , R 13 , R 14 , R 15 and R 16 each independently represents a fluorine atom, an alkyl group, an aryl group, or a heteroaryl group; m3 and n3 are each 0 or 1, satisfying m3+n3=1; R 51 , R 52 and R 53 each independently represents a substituent; p3, q3 and r3 each independently represents an integer of 0 to 4; where in the case where p3, q3 and r3 are each 2 to 4, R 51 , R 52 , R 53 may be the same as or different from each other, and R 51 's, R 52 's, or R 53 's may be bonded to each other to form a ring.
5. The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (II) is a compound represented by the following general formula (VI):
wherein: L 61 , L 62 , L 63 and L 64 each independently represents CR 12 R 13 , NR 14 , SiR 15 R 16 , anl O atom, or an S atom, wherein R 12 , R 13 , R 14 , R 15 and R 16 each independently represents a fluorine atom, an alkyl group, an aryl group, or a heteroaryl group; m4 and n4 are each 0 or 1, satisfying m4+n4=1; R 61 , R 62 and R 63 each independently represents a substituent; p4, q4 and r4 each independently represents an integer of 0 to 4; where in the case where p4, q4 and r4 are each 2 to 4, R 61 , R 62 , R 63 may be the same as or different from each other, and R 61 's, R 62 's, or R 63 's may be bonded to each other to form a ring.
6. The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (II) is contained in the light emitting layer.
7. The organic electroluminescent element according to claim 1 , the compound represented by the general formula (II) is a light emitting material contained in the light emitting layer.
8. The organic electroluminescent element according to claim 7 , further comprising a host material in the light emitting layer.
9. The organic electroluminescent element according to claim 8 , wherein the host material has an anthracene skeleton.
10. A light emitting device using the organic electroluminescent element according to claim 1 .
11. A display device using the organic electroluminescent element according to claim 1 .
12. An illumination device using the organic electroluminescent element according to claim 1 .
13. A compound represented by the following general formula (II):
wherein: R 1 to R 10 represent a hydrogen atom or a substituent, three out of the combinations of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 and R 10 and R 1 are substituted with each independent groups represented by the following general formula B, provided that at least one of the combinations of R 3 and R 4 , R 5 and R 6 , R 8 and R 9 , and R 10 and R 1 are substituted with the general formula B:
wherein L 2 represents CR 12 R 13 , NR 14 , SiR 15 R 16 , an O atom, or an S atom, wherein R 12 , R 13 , R 14 , R 15 and R 16 each independently represents a fluorine atom, an alkyl group, an aryl group, or a heteroaryl group; * and # represent sites for substitution with any one of the combinations of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 or R 10 and R 1 in the general formula (II), one of two groups in the combinations may be substituted at * or the other may be substituted at #; R 21 's each independently represents a substituent; o represents an integer of 0 to 4; where in the case where o is 2 to 4, the respective R 21 's may be the same as or different from each other, and R 21 's may be bonded to each other to form a ring.
14. The compound according to claim 13 , wherein the compound represented by the general formula (II) is a compound represented by the following general formula (III):
wherein: L 31 , L 32 , L 33 and L 34 each independently represents CR 12 R 13 , NR 14 , SiR 15 R 16 , anl O atom, or an S atom, wherein R 12 , R 13 , R 14 , R 15 and R 16 each independently represents a fluorine atom, an alkyl group, an aryl group, or a heteroaryl group; m1 and n1 are each 0 or 1, satisfying m1+n1=1; R 31 , R 32 and R 33 each independently represents a substituent; p1, q1 and r1 each independently represents an integer of 0 to 4; where in the case where p1, q1 and r1 are each 2 to 4, R 21 , R 32 and R 33 may be the same as or different from each other, and R 31 's, R 32 's, or R 33 's may be bonded to each other to form a ring.
15. The compound according to claim 13 , wherein the compound represented by the general formula (II) is a compound represented by the following general formula (IV):
wherein: L 41 , L 42 , L 43 and L 44 each independently represents CR 12 R 13 , NR 14 , SiR 15 R 16 , an O atom, or an S atom, wherein (R 12 , R 13 , R 14 , R 15 and R 16 each independently represents a fluorine atom, an alkyl group, an aryl group, or a heteroaryl group; m2 and n2 are each 0 or 1, satisfying m2+n2=1; R 41 , R 42 and R 43 each independently represents a substituent; p2, q2 and r2 each independently represents an integer of 0 to 4; where in the case where p2, q2 and r2 are each 2 to 4, R 41 , R 42 , R 43 may be the same as or different from each other, and R 41 's, R 42 's, or R 43 's may be bonded to each other to form a ring.
16. The compound according to claim 13 , wherein the compound represented by the general formula (II) is a compound represented by the following general formula (V):
wherein: L 51 , L 52 , L 53 and L 54 each independently represents CR 12 R 13 , NR 14 , SiR 15 R 16 , an O atom, or an S atom, wherein R 12 , R 13 , R 14 , R 15 and R 16 each independently represents a fluorine atom, an alkyl group, an aryl group, or a heteroaryl group; m3 and n3 are each 0 or 1, satisfying m3+n3=1; R 51 , R 52 and R 53 each independently represents a substituent; p3, q3 and r3 each independently represents an integer of 0 to 4; where in the case where p3, q3 and r3 are each 2 to 4, R 51 , R 52 , R 53 may be the same as or different from each other, and R 51 's, R 52 's, or R 53 's may be bonded to each other to form a ring.
17. The compound according to claim 13 , wherein the compound represented by the general formula (II) is a compound represented by the following general formula (VI):
wherein: L 61 , L 62 , L 63 and L 64 each independently represents CR 12 R 13 , NR 14 , SiR 15 R 16 , an O atom, or an S atom, wherein R 12 , R 13 , R 14 , R 15 and R 16 each independently represents a fluorine atom, an alkyl group, an aryl group, or a heteroaryl group; m4 and n4 are each 0 or 1, satisfying m4+n4=1; R 61 , R 62 and R 63 each independently represents a substituent; p4, q4 and r4 each independently represents an integer of 0 to 4; where in the case where p4, q4 and r4 are each 2 to 4, R 61 , R 62 , R 63 may be the same as or different from each other, and R 61 's, R 62 's, or R 63 's may be bonded to each other to form a ring.
18. The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (II) is selected from the group consisting of