Material for organic electroluminescence device and organic electroluminescence device

1. A material for organic electroluminescence device represented by formula (I);

wherein

each of A 1 and A 2 independently represents a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;

each of X 1 to X 8 and Y 1 to Y 8 independently represents N (nitrogen atom) or CR a (C represents a carbon atom);

each of R a independently represents a hydrogen atom, 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 silyl group, or a halogen atom, provided that when two or more R a groups exist, the R a groups may be the same or different;

L 1 represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms;

n represents an integer of 0 to 3, provided that when n=0, L 1 represents a single bond and one of X 5 to X 8 and one of Y 1 to Y 8 and A 2 are directly bonded to each other;

one of X 5 to X 8 and one of Y 1 to Y 8 and A 2 are bonded to each other via L 1 or directly;

each of sa and ta independently represents an integer of 0 to 5, each of sb, tb and tc independently represents an integer of 0 to 4, and sc represents an integer of 0 to 3, provided that sa+sb+sc+ta+tb+tc represents an integer of 1 to 5;

when sa is 1 to 5, A 1 and Q 1 of (Q 1 ) sa are bonded to each other;

when sb is 1 to 4, at least one of X 1 to X 4 and Q 1 of (Q 1 ) sb are bonded to each other;

when sc is 1 to 3, at least one of X 5 to X 8 and Q 1 of (Q 1 ) sc are bonded to each other;

when ta is 1 to 5, A 2 and Q 2 of (Q 2 ) ta are bonded to each other;

when tb is 1 to 4, at least one of Y 5 to Y 8 and Q 2 of (Q 2 ) tb are bonded to each other;

when tc is 1 to 4, at least one of Y 1 to Y 4 and Q 2 of (Q 2 ) tc are bonded to each other;

each of Q 1 and Q 2 independently represents -Az-W q ;

q represents an integer of 1 to 4;

when two or more Q 1 groups exist, the Q 1 groups may be the same or different;

when two or more Q 2 groups exist, the Q 2 groups may be the same or different;

Az represents a q+1 valent residue of a ring represented by formula (X):

wherein

each of Z 1 to Z 5 independently represents a nitrogen atom or CR b ;

R b is as defined in R a , provided that when any two of Z 1 to Z 5 adjacent to each other represent CR b , the adjacent R b groups may be bonded to each other to form a ring structure;

when two or more R b groups exist, the R b groups may be the same or different;

when two or more Az groups exist, the Az groups may be the same or different;

W represents a cyano group, a cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a cyano-substituted heterocyclic group having 5 to 30 ring atoms, provided that the cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and the cyano-substituted heterocyclic group having 5 to 30 ring atoms may be further substituted by a substituent other than a cyano group, and

when two or more W groups exist, the W groups may be the same or different.

2. The material for organic electroluminescence device according to claim 1 , represented by formula (II):

wherein

A 1 , A 2 , X 1 to X 8 , Y 1 to Y 8 , L 1 , n, sa, sb, sc, ta, tb, Q 1 , and Q 2 are as defined above,

tc represents an integer of 0 to 3, provided that sa+sb+sc+ta+tb+tc represents an integer of 1 to 5; and

one of X 5 to X 8 and one of Y 1 to Y 4 are bonded to each other via L 1 or directly.

3. The material for organic electroluminescence device according to claim 1 , represented by formula (III):

wherein

A 1 , A 2 , X 1 to X 8 , Y 1 to Y 8 , L 1 , n, Q 1 , and Q 2 are as defined above;

each of sa and ta independently represents an integer of 0 to 5, provided that sa+ta represents an integer of 1 to 5; and

one of X 5 to X 8 and one of Y 1 to Y 4 are bonded to each other via L 1 or directly.

4. The material for organic electroluminescence device according to claim 1 , wherein X 7 and Y 3 are bonded to each other via L 1 or directly.

5. The material for organic electroluminescence device according to claim 1 , wherein X 6 and Y 2 are bonded to each other via L 1 or directly.

6. The material for organic electroluminescence device according to claim 1 , wherein X 6 and Y 3 are bonded to each other via L 1 or directly.

7. The material for organic electroluminescence device according to claim 1 , wherein Az represents a q+1 valent residue of a ring selected from the group consisting of a substituted or unsubstituted pyrimidine ring, a substituted or unsubstituted triazine ring, a substituted or unsubstituted pyridine ring, and a substituted or unsubstituted quinazoline ring.

8. The material for organic electroluminescence device according to claim 1 , wherein L 1 represents a phenylene group and n represents an integer of 1 to 3, or L 1 represents a single bond and n represents 0.

9. The material for organic electroluminescence device according to claim 1 , wherein W represents a cyano-substituted phenyl group, a cyano-substituted biphenyl group, a cyano-substituted 9,9-diphenylfluorenyl group, a cyano-substituted 9,9′-spirobi[9H-fluorene]-2-yl group, a cyano-substituted 9,9-dimethylfluorenyl group, a cyano-substituted dibenzofuranyl group, or a cyano-substituted dibenzothiophenyl group.

10. The material for organic electroluminescence device according to claim 1 , wherein each of sa, sb, sc, ta, tb, and tc represents 0 or 1.

11. The material for organic electroluminescence device according to claim 1 , wherein each of ta, tb and tc represents 0.

12. The material for organic electroluminescence device according to claim 1 , wherein sa+sb+sc+ta+tb+tc represents 1.

13. The material for organic electroluminescence device according to claim 1 , wherein q represents 1 or 2.

14. The material for organic electroluminescence device according to claim 1 , wherein q represents 1.

15. An organic electroluminescence device comprising an organic thin film layer comprising one or more layers between a cathode and an anode,

wherein

the organic thin film layer comprises a light emitting layer, and

at least one layer of the organic thin film layer comprises the material for organic electroluminescence device according to claim 1 .

16. The organic electroluminescence device according to claim 15 , wherein the light emitting layer comprises the material for organic electroluminescence device.

17. The organic electroluminescence device according to claim 15 , wherein the light emitting layer comprises a phosphorescent emitting material selected from ortho metallated complexes of a metal selected from iridium (Ir), osmium (Os), and platinum (Pt).

18. The organic electroluminescence device according to claim 15 , wherein the light emitting layer comprises a first host material selected from the material for organic electroluminescence device and a second host material represented by formula (1);

wherein

Z 11 represents a ring structure fused to a side a and represented by formula (1-1) or (1-2), and Z 12 represents a ring structure fused to a side b and represented by formula (1-1) or (1-2), provided that at least one of Z 11 and Z 12 is represented by formula (1-1);

in formula (1-1),

a side c is fused to the side a or b of formula (1);

in formula (1-2),

any one of sides d, e and f is fused to the side a or b of formula (1);

in formulae (1-1) and (1-2),

X 11 represents a sulfur atom, an oxygen atom, N—R 19 , or C(R 20 )(R 21 );

each of R 11 to R 21 independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, 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 alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, provided that adjacent groups of R 11 to R 21 may be bonded to each other to form a ring;

M 1 represent a substituted or unsubstituted nitrogen-containing aromatic heteroring having 5 to 30 ring atoms;

L 2 represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, a cycloalkylene group having 5 to 30 ring atoms, or a group in which the preceding groups are directly linked to each other; and

k represents 1 or 2.

19. The organic electroluminescence device according to claim 18 , wherein the second host material is represented by formula (2):

wherein

Z 11 represents a ring structure fused to the side a and represented by formula (1-1) or (1-2), and Z 12 represents a ring structure fused to the side b and represented by formula (1-1) or (1-2), provided that at least one of Z 11 and Z 12 is represented by formula (1-1);

L 2 is as defined in formula (1);

each of X 12 to X 14 independently represents a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 2 , provided that at least one of X 12 to X 14 represents a nitrogen atom;

each of Y 11 to Y 13 independently represents CH or a carbon atom bonded to R 31 or L 2 ;

each of R 31 independently represents a halogen atom, a cyano group, 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 alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;

when two or more R 31 groups exist, the R 31 groups may be the same or different and adjacent R 34 groups may be bonded to each other to form a ring;

k represents 1 or 2, and m represents an integer of 0 to 4;

the side c of formula (1-1) is fused to the side a or b of formula (2); and

any one of sides d, e and f of formula (1-2) is fused to the side a or b of formula (2).

20. The organic electroluminescence device according to claim 18 , wherein the second host material is represented by formula (3):

wherein

L 2 is as defined in formula (1);

each of X 12 to X 14 independently represents a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 2 , provided that at least one of X 12 to X 14 represents a nitrogen atom;

each of Y 11 to Y 13 independently represents CH or a carbon atom bonded to R 31 or L 2 ;

each of R 31 independently represents a halogen atom, a cyano group, 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 alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;

when two or more R 31 groups exist, the R 31 groups may be the same or different and adjacent R 31 groups may be bonded to each other to form a ring;

m represents an integer of 0 to 4;

each of R 41 to R 48 independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, 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 alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms; and

adjacent groups of R 41 to R 48 may be bonded to each other to form a ring.

21. The organic electroluminescence device according to claim 18 , wherein the second host material is represented by formula (4):

wherein

L 2 is as defined in formula (1);

each of X 12 to X 14 independently represents a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 2 , provided that at least one of X 12 to X 14 represents a nitrogen atom;

each of Y 11 to Y 13 independently represents CH or a carbon atom bonded to R 31 or L 2 ;

each of R 31 independently represents a halogen atom, a cyano group, 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 alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;

when two or more R 31 groups exist, the R 31 groups may be the same or different and adjacent R 31 groups may be bonded to each other to form a ring;

m represents an integer of 0 to 4;

each of L 3 and L 4 independently represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, a cycloalkylene group having 5 to 30 ring atoms, or a group in which the preceding groups are directly linked to each other;

each of R 51 to R 54 independently represents a halogen atom, a cyano group, 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 alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;

when two or more R 51 groups exist, the R 51 groups may be the same or different and adjacent R 51 groups may be bonded to each other to form a ring;

when two or more R 52 groups exist, the R 52 groups may be the same or different and adjacent R 52 groups may be bonded to each other to form a ring;

when two or more R 53 groups exist, the R 53 groups may be the same or different and adjacent R 53 groups may be bonded to each other to form a ring;

when two or more R 54 groups exist, the R 54 groups may be the same or different and adjacent R 54 groups may be bonded to each other to form a ring;

M 2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; and

each of p and s independently represents an integer of 0 to 4, and each of q and r independently represents an integer of 0 to 3.

22. The organic electroluminescence device according to claim 15 , wherein the light emitting layer comprises a first host material selected from the materials for organic electroluminescence device and a second host material selected from compounds having no cyano group.