Material for organic electroluminescence device and organic electroluminescence device

1. An organic electroluminescence device which comprises a light emitting layer which is disposed between a cathode and an anode and comprises a first host material, a second host material and a light emitting material,

wherein the first host material is represented by formula (A):

wherein

each of A 1 and A 2 independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted residue selected from the group consisting of a pyrrole ring, an isoindole ring, a benzofuran ring, an isobenzofuran ring, a dibenzothiophene ring, an indole ring, a pyrrolidine ring, a dioxane ring, a piperidine ring, a morpholine ring, a piperazine ring, a carbazole ring, a furan ring, a thiophene ring, an oxazole ring, an oxadiazole ring, a benzoxazole ring, a thiazole ring, a thiadiazole ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a dibenzofuran ring, and a benzo[c]dibenzofuran ring;

A 3 represents a divalent monocyclic heterocyclic group having 5 ring atoms;

A 3 may be independently substituted with at least one group selected from the group consisting of a cyano group, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a haloalkoxyl group having 1 to 20 carbon atoms, an alkyl silyl group having 1 to 10 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an aralkyl group having 6 to 30 carbon atoms, and a heteroaryl group having 5 to 30 ring atoms, a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a phenanthryl group, a spirobifluorenyl group, a triphenylenyl group, a fluorenyl group, a spirobifluorenyl group, and a fluoranthenyl group,

m represents an integer of 0 to 3;

each of X 1 to X 8 and Y 1 to Y 8 independently represents N or CR a ;

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, a halogen atom, or a cyano group, provided that when two or more R a groups exist, the R a groups may be the same or different and one of X 5 to X 8 and one of Y 1 to Y 4 are bonded to each other via A 3 ; and

the formula (A) satisfies at least one of the following requirements (i) to (v):

(i) at least one of A 1 and A 2 represents a cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted group selected from the group consisting of a pyrrole ring, an isoindole ring, a benzofuran ring, an isobenzofuran ring, a dibenzothiophene ring, an indole ring, a pyrrolidine ring, a dioxane ring, a piperidine ring, a morpholine ring, a piperazine ring, a carbazole ring, a furan ring, a thiophene ring, an oxazole ring, an oxadiazole ring, a benzoxazole ring, a thiazole ring, a thiadiazole ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a dibenzofuran ring, and a benzo[c]dibenzofuran ring;

(ii) at least one of X 1 to X 4 and Y 5 to Y 8 represents CR a , and at least one of R a in X 1 to X 4 and Y 5 to Y 8 represents 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;

(iii) m represents an integer of 1 to 3 and at least one of A 3 represents a cyano-substituted divalent heterocyclic group having 5 ring atoms;

(iv) at least one of X 5 to X 8 and Y 1 to Y 4 represents CR a , and at least one of R a in X 5 to X 8 and Y 1 to Y 8 represents 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; and

(v) at least one of X 1 to X 8 and Y 1 to Y 8 represents C—CN; and

the second host material is represented by formula (1):

wherein

Z 1 represents a ring structure fused to a side a and represented by formula (1-1) or (1-2), and Z 2 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 1 and Z 2 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 a ring;

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

L 1 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.

2. The organic electroluminescence device according to claim 1 , wherein the first host material satisfies at least one of the requirements (i) and (ii).

3. The organic electroluminescence device according to claim 1 , wherein the second host material is represented by formula (2):

wherein

Z 1 represents a ring structure fused to the side a and represented by formula (1-1) or (1-2), and Z 2 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 1 and Z 2 is represented by formula (1-1);

L 1 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 1 , 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 1 ;

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;

k represents 1 or 2, and n 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).

4. The organic electroluminescence device according to claim 1 , wherein the second host material is represented by formula (3):

wherein

L 1 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 1 , 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 1 ;

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;

n 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.

5. The organic electroluminescence device according to claim 1 , wherein the first host material satisfies only the requirement (i).

6. The organic electroluminescence device according to claim 1 , wherein the second host material is represented by formula (4):

wherein

L 1 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 1 , 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 1 ;

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;

n represents an integer of 0 to 4;

each of L 2 and L 3 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.

7. The organic electroluminescence device according to claim 1 , wherein at least one of A 1 and A 2 represents a cyano-substituted phenyl group, a cyano-substituted naphthyl group, a cyano-substituted phenanthryl group, a cyano-substituted dibenzofuranyl group, a cyano-substituted dibenzothiophenyl group, a cyano-substituted biphenyl group, a cyano-substituted terphenyl 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, or a cyano-substituted triphenylenyl group.

8. The organic electroluminescence device according to claim 1 , wherein the light emitting material comprises a phosphorescent emitting material selected from ortho metallated complexes of a metal selected from iridium (Ir), osmium (Os), and platinum (Pt).

9. The organic electroluminescence device according to claim 1 , wherein a peak of emission wavelength of the phosphorescent emitting material is 490 nm or longer and 700 nm or shorter.

10. The organic electroluminescence device according to claim 1 , wherein m of formula (A) represents 0.