Organic electroluminescent material, organic electroluminescent element, display device and lighting device
View Patent ↗Disclosed are: an organic EL material which emits light having a short wavelength and has high luminous efficiency and long light emission life; an organic EL element which contains the organic EL material; and a lighting device and a display device, each of which comprises the organic EL element. The organic EL material is a compound represented by Formula (1):
1. An organic electroluminescence material being a compound represented by Formula (1),
wherein A and B each represent a 6-membered aromatic hydrocarbon group, or a 5- or 6-membered aromatic heterocyclic group, provided that at least one of A and B represents a 5-membered aromatic heterocyclic group; Q represents a substituent having a vacant orbital which is capable of accepting a π electron from A or B; M represents a transition metal element belonging to groups 8 to 10 in the periodic table; L represents a ligand which is capable of coordinating with M; m1 is an integer of 1 to 3; m2 is an integer of 0 to 2; and n is an integer of 1 to 4, and
wherein the substituent Q represents one selected from the group consisting of Q-1, Q-2 and Q-3,
wherein Ar 1 and Ar 2 each respectively represent an aromatic hydrocarbon ring group or an aromatic heterocyclic group, provided that Ar 1 and Ar 2 may be joined to form an aromatic ring; Ra, Rb and Rc each represent an alkyl group, a cycloalkyl group, an aromatic hydrocarbon ring group or an aromatic heterocyclic group; J 1 , J 2 and J 3 each represent an arylene group or a heteroarylene group; and r, s and t each represent an integer of 0 or 1.
2. The organic electroluminescence material of claim 1
wherein the compound represented by Formula (1) is further represented by Formula (2), Formula (3), Formula (4), or Formula (5),
wherein R represents an alkyl group, a cycloalkyl, an aromatic hydrocarbon group, or an aromatic heterocyclic group;
R 11 to R 16 each represent a hydrogen atom or a substituent, provided that at least one of R 11 to R 16 represents the substituent Q having a vacant orbital which is capable of accepting a π electron from a bonded ring; M represents a transition metal element belonging to groups 8 to 10 in the periodic table; L represents a ligand which is capable of coordinating with M; m1 is an integer of 1 to 3; and m2 is an integer of 0 to 2,
wherein T represents an oxygen atom or a sulfur atom; R 21 to R 26 each represent a hydrogen atom or a substituent, provided that at least one of R 21 to R 26 represents the substituent Q having a vacant orbital which is capable of accepting a π electron from a bonded ring; M represents a transition metal element belonging to groups 8 to 10 in the periodic table; L represents a ligand which is capable of coordinating with M; m1 is an integer of 1 to 3; and m2 is an integer of 0 to 2,
wherein R 31 to R 37 each represent a hydrogen atom or a substituent, provided that at least one of R 31 to R 37 represents the substituent Q having a vacant orbital which is capable of accepting a π electron from a bonded ring; M represents a transition metal element belonging to groups 8 to 10 in the periodic table; L represents a ligand which is capable of coordinating with M; m1 is an integer of 1 to 3; and m2 is an integer of 0 to 2,
wherein R 51 to R 57 each represent a hydrogen atom or a substituent, provided that at least one of R 51 to R 57 represents the substituent Q having a vacant orbital which is capable of accepting a n electron from a bonded ring; U 1 and U 2 each represent a carbon atom or a nitrogen atom; M represents a transition metal element belonging to groups 8 to 10 in the periodic table; L represents a ligand which is capable of coordinating with M; m1 is an integer of 1 to 3; m2 is an integer of 0 to 2; and x1 and x2 each represent an integer of 0 or 1.
3. The organic electroluminescence material of claim 2 ,
wherein R 13 in the compound represented by Formula (2), R 23 in the compound represented by Formula (3), R 33 in the compound represented by Formula (4), and R 55 in the compound represented by Formula (5) each represents the substituent Q.
4. The organic electroluminescence material of claim 1 ,
wherein the substituent Q represents one selected from the group consisting of Q-1-1 to Q-1-10,
wherein Ar 1 and Ar 2 each respectively represent an aromatic hydrocarbon ring group or an aromatic heterocyclic group, provided that Ar 1 and Ar 2 may be joined to form an aromatic ring; D 1 to D 5 each represent a carbon atom or a nitrogen atom; Rd and Re each represent an alkyl group, a cycloalkyl group, an aromatic hydrocarbon ring group or an aromatic heterocyclic group; p represents an integer of 0 to 4, and q represents an integer of 0 to 2; E 1 represents O, S or N-Rf, provided that Rf represents an alkyl group, a cycloalkyl group, an aromatic hydrocarbon ring group or an aromatic heterocyclic group; E 2 and E 3 each represent a carbon atom or a nitrogen atom; Mes represents a mesityl group; W 1 represents an integer of 1 to 5; and W2 represents an integer of 1 to 3.
5. The organic electroluminescence material of claim 2 ,
wherein, in the compound represented by Formula (2), in the compound represented by Formula (3), in the compound represented by Formula (4), or in the compound represented by Formula (5), M represents a platinum atom or an iridium atom.
6. An organic electroluminescence element comprising at least one light emitting layer sandwiched between an anode and a cathode,
wherein the light emitting layer contains at least one compound represented by Formula (1) of claim 1 .
7. The organic electroluminescence element of claim 6 ,
wherein the compound represented by Formula (1) is further represented by Formula (2), Formula (3), Formula (4), or Formula (5) ,
wherein R represents an alkyl group, a cycloalkyl, an aromatic hydrocarbon group, or an aromatic heterocyclic group; R 11 to R 16 each represent a hydrogen atom or a substituent, provided that at least one of R 11 to R 16 represents the substituent Q having a vacant orbital which is capable of accepting a π electron from a bonded ring; M represents a transition metal element belonging to groups 8 to 10 in the periodic table; L represents a ligand which is capable of coordinating with M; m1 is an integer of 1 to 3; and m2 is an integer of 0 to 2,
wherein T represents an oxygen atom or a sulfur atom; R 21 to R 26 each represent a hydrogen atom or a substituent, provided that at least one of R 21 to R 26 represents the substituent Q having a vacant orbital which is capable of accepting a π electron from a bonded ring; M represents a transition metal element belonging to groups 8 to 10 in the periodic table; L represents a ligand which is capable of coordinating with M; m1is an integer of 1 to 3; and m2 is an integer of 0 to 2,
wherein R 31 to R 37 each represent a hydrogen atom or a substituent, provided that at least one of R 31 to R 37 represents the substituent Q having a vacant orbital which is capable of accepting a π electron from a bonded ring; M represents a transition metal element belonging to groups 8 to 10 in the periodic table; L represents a ligand which is capable of coordinating with M; m1 is an integer of 1 to 3; and m2 is an integer of 0 to 2,
wherein R 51 to R 57 each represent a hydrogen atom or a substituent, provided that at least one of R 51 to R 57 represents the substituent Q having a vacant orbital which is capable of accepting a n electron from a bonded ring; U 1 and U 2 each represent a carbon atom or a nitrogen atom; M represents a transition metal element belonging to groups 8 to 10 in the periodic table; L represents a ligand which is capable of coordinating with M; m1 is an integer of 1 to 3; m2 is an integer of 0 to 2; and x1 and x2 each represent an integer of 0 or 1.
8. The organic electroluminescence element of claim 7 ,
wherein R 13 in the compound represented by Formula (2), R 23 in the compound represented by Formula (3), R 33 in the compound represented by Formula (4), and R 55 in the compound represented by Formula (5) each represents the substituent Q.
9. The organic electroluminescence element of claim 7 ,
wherein, in the compound represented by Formula (2), in the compound represented by Formula (3), in the compound represented by Formula (4), or in the compound represented by Formula (5), the substituent Q is a substituent containing an element belonging to group 13 in the periodic table, a sulfur atom or a phosphor atom.
10. The organic electroluminescence element of claim 9 ,
wherein the substituent Q is one selected from the group consisting of the partial structures of Q-1, Q-2 and Q-3,
wherein Ar 1 and Ar 2 each respectively represent an aromatic hydrocarbon ring group or an aromatic heterocyclic group, provided that Ar 1 and Ar 2 may be joined to form an aromatic ring;
Ra, Rb and Rc each represent an alkyl group, a cycloalkyl group, an aromatic hydrocarbon ring group or an aromatic heterocyclic group; J 1 , J 2 and J 3 each represent an arylene group or a heteroarylene group; and r, s and t each represent an integer of 0 or 1.
11. The organic electroluminescence element of claim 10 ,
wherein the substituent Q is one selected from the group consisting of the partial structures Q-1-1 to Q-1-10 ,
wherein Ar 1 and Ar 2 each respectively represent an aromatic hydrocarbon ring group or an aromatic heterocyclic group, provided that Ar 1 and Ar 2 may be joined to form an aromatic ring; D 1 to D 5 each represent a carbon atom or a nitrogen atom; Rd and Re each represent an alkyl group, a cycloalkyl group, an aromatic hydrocarbon ring group or an aromatic heterocyclic group; p represents an integer of 0 to 4, and q represents an integer of 0 to 2; E 1 represents O, S or N-Rf, provided that Rf represents an alkyl group, a cycloalkyl group, an aromatic hydrocarbon ring group or an aromatic heterocyclic group; E 2 and E 3 each represent a carbon atom or a nitrogen atom; Mes represents a mesityl group; W1 represents an integer of 1 to 5; and W2 represents an integer of 1 to 3.
12. The organic electroluminescence element of claim 7 ,
wherein, in the compound represented by Formula (2), in the compound represented by Formula (3), in the compound represented by Formula (4), or in the compound represented by Formula (5), M represents a platinum atom or an iridium atom.
13. The organic electroluminescence element of any one of claim 7 ,
comprising an organic layer containing at least one compound represented by Formula (2), Formula (3), Formula (4), or Formula (5); and the aforesaid organic layer is formed with a wet process.
14. A display device comprising the organic electroluminescence element of claim 6 .
15. A lighting device comprising the organic electroluminescence element of claim 6 .
16. The organic electroluminescence material of claim 1 ,
wherein in the compound represented by Formula (1), M represents a platinum atom or an iridium atom.
17. The organic electroluminescence material of claim 6 ,
wherein in the compound represented by Formula (1), M represents a platinum atom or an iridium atom.
18. The organic electroluminescence material of claim 6 ,
wherein an organic layer containing at least one compound represented by Formula (1); and the aforesaid organic layer is formed with a wet process.