Organic electroluminescence device and electronic device

1. An organic electroluminescence device, comprising:

an anode;

an emitting layer; and

a cathode, wherein

the emitting layer comprises a first compound, a second compound, and a third compound,

the first compound is a delayed fluorescent compound,

the first compound has an energy gap T 77K at 77 [K] larger than an energy gap T 77K at 77 [K] of the second compound,

the third compound has an energy gap T 77K larger than the energy gap T 77K at 77 [K] of the second compound, and

the second compound is a compound having a fused ring structure represented by a formula (2) below, the fused ring structure having eight or less rings in total,

where: a monocyclic ring or a fused ring is optionally fused to at least one of positions a, c, d, e, f, h, i and j;

a five-membered ring or a fused ring having a five-membered ring is optionally fused to at least one of positions b and g;

when a six-membered ring is fused to the positions i and j, a monocyclic ring or a fused ring is also fused to the positions d and e;

when a six-membered ring is fused to the positions d and e, a monocyclic ring or a fused ring is also fused to the positions i and j;

when a fused ring having a five-membered ring is fused to the position b, the five-membered ring of the fused ring is directly fused to the position b; and

when a fused ring having a five-membered ring is fused to the position g, the five-membered ring of the fused ring is directly fused to the position g.

2. The organic electroluminescence device according to claim 1 , wherein

the first compound has a content ratio in a range from 10 mass % to 60 mass % in the emitting layer.

3. The organic electroluminescence device according to claim 1 , wherein

the first compound is a compound represented by a formula (1) below,

where: A is a group having a partial structure selected from formulae (a-1) to (a-7) below; when a plurality of A are present, the plurality of A are optionally mutually the same or different and the plurality of A are optionally mutually bonded to form a saturated or unsaturated ring;

B is a group having a partial structure selected from formulae (b-1) to (b-6) below; when a plurality of B are present, the plurality of B are optionally mutually the same or different and the plurality of B are optionally mutually bonded to form a saturated or unsaturated ring;

a, b and d are each independently an integer of 1 to 5;

c is an integer of 0 to 5;

when c is 0, A is bonded to B by a single bond or a spiro bond;

when c is an integer of 1 to 5, L is a linking group selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; and

when a plurality of L are present, the plurality of L are optionally mutually the same or different and are optionally mutually bonded to form a saturated or unsaturated ring,

where, in the formulae (b-1) to (b-6):

R is each independently a hydrogen atom or a substituent;

when R is a substituent, the substituent is selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; and

when a plurality of R are present, the plurality of R are optionally mutually the same or different and are optionally mutually bonded to form a saturated or unsaturated ring.

4. The organic electroluminescence device according to claim 3 , wherein

the first compound is a compound represented by a formula (10) below,

where: a1 is 0 or 1 and a2 is 0 or 1, provided that a1+a2≥1;

m1 is an integer of 1 to 5;

when a2 is 0, R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent;

when R 1 and R 2 are substituents, the substituents are each independently selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, and a substituted silyl group;

when a2 is 1, R 1 and R 2 are each independently a linking group selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, and a substituted silyl group;

when m1 is 2 or more, a plurality of R 1 are mutually the same or different and a plurality of R 2 are mutually the same or different;

A 1 and A 2 are each independently a group having a partial structure selected from formulae (a-1) to (a-7) below; when m1 is 2 or more, a plurality of A 2 are mutually the same or different;

when a1 is 0, L 2 is a hydrogen atom or a monovalent substituent;

when L 2 is a monovalent substituent, the substituent is selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;

when a1 is 1, L 2 is a single bond or a linking group;

when L 2 is a linking group, the linking group is selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;

L 1 is a single bond or a linking group;

when L 1 is a linking group, the linking group is selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; and

when m1 is 2 or more, a plurality of L 1 are mutually the same or different.

5. The organic electroluminescence device according to claim 3 , wherein

the first compound is a compound represented by a formula (10′) below,

where: m2 is 2;

a2 is 0 or 1;

a plurality of a2 are mutually the same or different;

m1 is an integer of 1 to 5;

a plurality of m1 are mutually the same or different;

when a2 is 0, R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent;

when R 1 and R 2 are substituents, the substituents are each independently selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, and a substituted silyl group;

when a2 is 1, R 1 and R 2 are each independently a linking group selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, and a substituted silyl group;

a plurality of R 1 are mutually the same or different;

a plurality of R 2 are mutually the same or different;

A 1 and A 2 are a group having a partial structure selected from the formulae (a-1) to (a-7);

a plurality of A 2 are mutually the same or different;

L 2 is a single bond or a linking group;

when L 2 is a linking group, the linking group is selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;

a plurality of L 2 are mutually the same or different;

L 1 is a single bond or a linking group;

when L 1 is a linking group, the linking group is selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; and

a plurality of L 1 are mutually the same or different.

6. The organic electroluminescence device according to claim 4 , wherein

the first compound is selected from the group consisting of a compound represented by a formula (10B), a compound represented by a formula (10C), a compound represented by a formula (10D), and a compound represented by a formula (10E) below,

where: in the formula (10D), X 2 is selected from the group consisting of ═N-L 1 -L 2 -A 1 , an oxygen atom, a sulfur atom and a selenium atom; and

in the formulae (10B), (10C), (10D) and (10E), R 1 , R 2 , A 1 , A 2 , L 1 and L 2 each represent the same as R 1 , R 2 , A 1 , A 2 , L 1 and L 2 in the formula (10).

7. The organic electroluminescence device according to claim 1 , wherein

the second compound is a fluorescent compound having an emission peak wavelength of 550 nm or less.

8. The organic electroluminescence device according to claim 1 , wherein

the second compound is a blue fluorescent compound.

9. The organic electroluminescence device according to claim 1 , wherein

the second compound is a compound having a benzofluorene skeleton, fluoranthene skeleton, pyrene skeleton, or chrysene skeleton.

10. The organic electroluminescence device according to claim 9 , wherein

the second compound is a compound represented by a formula (21) below,

where: n1 is an integer of 1 or more;

Ar 0 is a group having a benzofluorene skeleton, fluoranthene skeleton, pyrene skeleton, or chrysene skeleton;

A 1 and Ar 2 are each independently a substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms;

Ar 1 and Ar 2 are optionally mutually bonded to form a saturated or unsaturated ring;

when n1 is 2 or more, a plurality of Ar 1 are mutually the same or different and a plurality of Ar 2 are mutually the same or different;

L 0 is a single bond or a linking group;

when L 0 is a linking group, the linking group is selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; and

when n1 is 2 or more, a plurality of L 0 are mutually the same or different.

11. The organic electroluminescence device according to claim 10 , wherein

Ar 1 and Ar 2 are each independently selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

12. The organic electroluminescence device according to claim 10 , wherein

at least one of Ar 1 and Ar 2 is a substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.

13. The organic electroluminescence device according to claim 10 , wherein

at least one of Ar 1 and Ar 2 is the group represented by a formula (22) below,

where: x is an integer of 0 to 3;

y is an integer of 0 to 7;

X 5 represents an oxygen atom, a sulfur atom or a selenium atom;

when x is 0, the group represented by the formula (22) is bonded by a single bond to a nitrogen atom of the formula (21);

when x is an integer of 1 to 3, Ar 5 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms;

when x is 2 or more, a plurality of Ar 5 are optionally mutually the same or different and are optionally mutually bonded to form a saturated or unsaturated ring;

R 5 is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted silyl group, a carboxyl group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted alkoxycarbonyl group having 1 to 30 carbon atoms;

when y is 2 or more, a plurality of R 5 are optionally mutually the same or different and are optionally mutually bonded to form a saturated or unsaturated ring.

14. The organic electroluminescence device according to claim 13 , wherein

Ar 1 is a substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and

Ar 2 is a group represented by the formula (22).

15. The organic electroluminescence device according to claim 14 , wherein

Ar 1 is a substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 20 ring carbon atoms.

16. The organic electroluminescence device according to claim 14 , wherein

Ar 1 is a group selected from a phenyl group, biphenyl group, naphthyl group, phenanthryl group, terphenyl group and fluorenyl group.

17. The organic electroluminescence device according to claim 13 , wherein

X 5 is an oxygen atom.

18. The organic electroluminescence device according to claim 10 , wherein

Ar 0 is a group having a pyrene skeleton or a chrysene skeleton.

19. The organic electroluminescence device according to claim 10 , wherein

the group having the benzofluorene skeleton as Ar 0 in the formula (21) is a group represented by a formula (Ar-1) below,

where: R 11 and R 12 each independently represent a hydrogen atom or a substituent;

when R 1 and R 2 are substituents, the substituents are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms;

R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 and R 22 each independently represent a hydrogen atom, a substituent or a single bond to be bonded to L 0 ; at least one of R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 and R 22 is a single bond to be bonded to L 0 ;

when R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 and R 22 are substituents, the substituents are each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted silyl group, a carboxyl group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted alkoxycarbonyl group having 1 to 30 carbon atoms;

at least one of a combination of R 13 and R 14 , a combination of R 14 and R 15 , a combination of R 15 and R 16 , a combination of R 17 and R 18 , a combination of R 18 and R 19 , a combination of R 19 and R 20 , a combination of R 20 and R 21 , and a combination of R 21 and R 22 optionally forms a saturated or unsaturated ring.

20. The organic electroluminescence device according to claim 19 , wherein

at least one of Ar 1 and Ar 2 is the group represented by the formula (Ar-1).

21. The organic electroluminescence device according to claim 19 , wherein

the group represented by the formula (Ar-1) is a group represented by a formula (Ar-2) below,

where: R 11 , R 12 , R A and R B each independently represent a hydrogen atom or a substituent;

when R 11 , R 12 , R A and R B are substituents, the substituents are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms;

R 13 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 and R 26 each independently represent a hydrogen atom, a substituent or a single bond to be bonded to L 0 ;

at least one of R 13 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 and R 26 is a single bond to be bonded to L 0 ;

when R 13 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 and R 26 are substituents, the substituents are each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted silyl group, a carboxyl group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted alkoxycarbonyl group having 1 to 30 carbon atoms;

at least one of a combination of R 17 and R 18 , a combination of R 18 and R 19 , a combination of R 19 and R 20 , a combination of R 20 and R 21 , a combination of R 21 and R 22 , a combination of R 23 and R 24 , a combination of R 24 and R 25 , and a combination of R 25 and R 26 optionally forms a saturated or unsaturated ring.

22. The organic electroluminescence device according to claim 21 , wherein

at least one of R 21 and R 25 is a single bond to be bonded to L 0 .

23. The organic electroluminescence device according to claim 9 , wherein

the second compound is a compound represented by a formula (23) below,

where: p is an integer of 0 to 5;

q and r are each independently an integer of 1 to 5;

Ar 10 is a group having a benzofluorene skeleton, fluoranthene skeleton, pyrene skeleton, or chrysene skeleton;

R 10 is a substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms;

when a plurality of R 10 are present, the plurality of R 10 are optionally mutually the same or different and are optionally mutually bonded to form a saturated or unsaturated ring;

when p is 0, Ar 10 is bonded to R 10 by a single bond;

when p is an integer of 1 to 5, L 10 is a linking group selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; and

when a plurality of L 10 are present, the plurality of L 10 are optionally mutually the same or different and are optionally mutually bonded to form a saturated or unsaturated ring.

24. The organic electroluminescence device according to claim 23 , wherein

Ar 10 is a group having a benzofluoranthene skeleton.

25. The organic electroluminescence device according to claim 1 , further comprising:

a hole transporting layer between the anode and the emitting layer.

26. The organic electroluminescence device according to claim 1 , further comprising:

an electron transporting layer between the emitting layer and the cathode.

27. An electronic device comprising the organic electroluminescence device according to claim 1 .