Organic electroluminescent element, material for organic electroluminescent element, light emitting device, display device and lighting device each using said element, and compound used for said element
This application relates, in part, to 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 layer of the organic layer(s) contains a compound represented by the following formula (1). The organic electroluminescent element has low driving voltage and excellent durability. wherein X 1 to X 11 represent CR 0 or N, and R 0 represents a hydrogen atom or a substituent. Adjacent two of X 1 to X 11 each independently represent at least CR 0 , R 0 s of the adjacent two CR 0 s are bonded to each other to form a ring, and only one R 0 of the adjacent two CR 0 s represents an aryl group or a heteroaryl group.
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 layer of the organic layer(s) contains a compound represented by one of the following general formulae (3), (7), (8), or (9):
wherein Y B1 , Y F1 , Y G1 and Y H1 each independently represents CR 1 R 2 , NR 3 , O, S, or Se, R 1 to R 3 each independently represents a substituent, X B1 , X B4 to X H15 , X F1 to X F4 , X F7 to X F15 , X G1 to X G5 , X G8 to X G15 , X H1 to X H5 , and X H8 to X H15 each independently represents CR 4 or N, and each R 4 independently represents a hydrogen atom or a substituent,
wherein when Y B1 is NR 3 , R 3 is not connected to X B1 or X B12 to form a ring; and
wherein when Y F1 is NR 3 , R 3 is not connected to X F4 or X F12 to form a ring.
2. The organic electroluminescent element according to claim 1 , wherein the compound contained in at least one layer of the organic layer(s) is represented by one of the general formulae (11), (15), (16), or (17):
wherein Y B1 , Y F1 , Y G1 , and Y H1 each independently represents CR 1 R 2 , NR 3 , O, S, or Se, and R 1 to R 3 each independently represents a substituent; R B1 , R B4 to R B15 , R F1 to R F4 , R F7 to R F15 , R G1 to R G5 , R G8 to R G15 , R H1 to R H5 , and R H8 to R H15 each independently represents a hydrogen atom or a substituent,
wherein when Y B1 is NR 3 , R 3 is not connected to R B1 or R B12 to form a ring; and
wherein when Y F1 is NR 3 , R 3 is not connected to R F4 or R F12 to form a ring.
3. The organic electroluminescent element according to claim 1 , wherein the value of LUMO of the compound represented by one of the general formulae (3), (7), (8), or (9), as determined by an electron density functional theory B3LYP/6-31G (d) level, is more than 1.25.
4. The organic electroluminescent element according to claim 1 , wherein the light emitting layer contains at least one kind of phosphorescent light emitting material.
5. The organic electroluminescent element according to claim 4 , wherein the phosphorescent light emitting material is an iridium complex represented by the following general formula (E-1):
wherein Z 1 and Z 2 each independently represents a carbon atom or a nitrogen atom;
A 1 represents an atomic group that forms a 5- or 6-membered hetero ring together with Z 1 and a nitrogen atom;
B 1 represents an atomic group that forms a 5- or 6-membered ring together with Z 2 and a carbon atom;
(X—Y) represents a mono-anionic bidentate ligand; and
n E1 represents an integer of 1 to 3.
6. The organic electroluminescent element according to claim 5 , wherein the iridium complex represented by the general formula (E-1) is represented by the following general formula (E-2):
wherein A E1 to A E8 each independently represents a nitrogen atom or C—R E ;
R E represents a hydrogen atom or a substituent;
(X—Y) represents a mono-anionic bidentate ligand; and
n E2 represents an integer of 1 to 3.
7. The organic electroluminescent element according to claim 1 , wherein the light emitting layer contains the compound represented by one of the general formulae (3), (7), (8), or (9).
8. A light emitting device using the organic electroluminescent element according to claim 1 .
9. A display device using the organic electroluminescent element according to claim 1 .
10. An illumination device using the organic electroluminescent element according to claim 1 .
11. A compound represented by one of the following general formulae (3), (7), (8), or (9):
wherein Y B1 , Y F1 , Y G1 , and Y H1 each independently represents CR 1 R 2 , NR 3 , O, S, or Se, R 1 to R 3 each independently represents a substituent, X B1 , X B4 to X B15 , X F1 to X F4 , X F7 to X F15 , X G1 to X G5 , X G8 to X G15 , X H1 to X H5 , and X H8 to X H15 each independently represents CR 4 or N, and each R 4 independently represents a hydrogen atom or a substituent,
wherein when Y B1 is NR 3 , R 3 is not connected to X B1 or X B12 to form a ring; and
wherein when Y B1 is NR 3 , R 3 is not connected to X B1 or X B12 to form a ring.
12. The compound according to claim 11 , which is represented by any one of the following general formulae (11), (15), (16), or (17):
wherein Y B1 , Y F1 , Y G1 and Y H1 each independently represents CR 1 R 2 , NR 3 , O, S, or Se, and R 1 to R 3 each independently represents a substituent; R B1 , R B4 to R B15 , R F1 to R F4 , R F7 to R F15 , R G1 to R G5 , R G8 to R G15 , R H1 to R H5 , and R H8 to R H15 each independently represents a hydrogen atom or a substituent
wherein when Y B1 is NR 3 , R 3 is not connected to R B1 or R B12 to form a ring; and
wherein when Y F1 is NR 3 , R 3 is not connected to R F4 or R F12 to form a ring.
13. A material for an organic electroluminescent element, represented by one of the following general formulae (3), (7), (8), or (9):
wherein Y B1 , Y F1 , Y G1 , and Y H1 each independently represents CR 1 R 2 , NR 3 , O, S, or Se, R 1 to R 3 each independently represents a substituent, X B1 , X B4 to X B15 , X F1 to X F4 , X F7 to X F15 , X G1 to X G5 , X G8 to X G15 , X H1 to X H5 , and X H8 to X H15 each independently represents CR 4 or N, and each R 4 independently represents a hydrogen atom or a substituent,
wherein when Y B1 is NR 3 , R 3 is not connected to X B1 or X B12 to form a ring; and
wherein when Y F1 is NR 3 , R 3 is not connected to X F4 or X F12 to form a ring.
14. The material for an organic electroluminescent element according to claim 13 , which is represented by any one of the following general formulae (11), (15), (16), or (17):
wherein Y B1 , Y F1 , Y G1 , and Y H1 each independently represents CR 1 R 2 , NR 3 , O, S, or Se, and R 1 to R 3 each independently represents a substituent; R B1 , R B4 to R B15 , R F1 to R F4 , R F7 to R F15 , R G1 to R G5 , R G8 to R G15 , R H1 to R H5 , and R H8 to R H15 each independently represents a hydrogen atom or a substituent,
wherein when Y B1 is NR 3 , R 3 is not connected to R B1 or R B12 to form a ring; and
wherein when Y F1 is NR 3 , R 3 is not connected to R F4 or R F12 to form a ring.
15. The organic electroluminescent element according to claim 1 , wherein the compound contained in at least one layer of the organic layer(s) is represented by general formulae (11):
wherein Y B1 represents O; and R B1 , and R B4 to R B15 each independently represents a hydrogen atom or a substituent, wherein when Y B1 is NR 3 , R 3 is not connected to R B1 or R B12 to form a ring.
16. The organic electroluminescent element according to claim 1 , wherein the compound contained in at least one layer of the organic layer(s) is represented by general formulae (15):
wherein Y F1 represents NR 3 , and R 3 represents a substituent; and R F1 to R F4 , and R F7 to R F15 , each independently represents a hydrogen atom or a substituent, wherein when Y F1 is NR 3 , R 3 is not connected to R F4 or R F12 to form a ring.
17. The compound according to claim 11 , wherein the compound is represented by general formulae (11):
wherein Y B1 represents O; and R B1 , and R B4 to R B15 each independently represents a hydrogen atom or a substituent, wherein when Y B1 is NR 3 , R 3 is not connected to R B1 or R B12 to form a ring.
18. The compound according to claim 11 , wherein the compound is represented by general formulae (15):
wherein Y F1 represents NR 3 , and R 3 represents a substituent; and R F1 to R F4 , and R F7 to R F15 each independently represents a hydrogen atom or a substituent, wherein when Y F1 is NR 3 , R 3 is not connected to R F4 or R F12 to form a ring.