Biscarbazole derivative, material for organic electroluminescence device and organic electroluminescence device using the same

1. An organic electroluminescence device comprising:

a cathode;

an anode; and

a plurality of organic thin-film layers provided between the cathode and the anode, wherein

at least one of the organic thin-film layers is an emitting layer comprising a first host material, a second host material and a phosphorescent material that exhibits a phosphorescence,

the first host material is a compound represented by a formula (4) below, and

the second host material is a compound represented by a formula (5) below,

where

A 1 represents a substituted or unsubstituted nitrogen-containing heterocyclic group having 1 to 30 ring carbon atoms,

when A 1 has a substituent, the substituent of A 1 is an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, a cyano group, a halogen atom, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms, or a monocyclic aromatic heterocyclic group having 2 to 30 ring carbon atoms,

A 2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted nitrogen-containing heterocyclic group having 1 to 30 ring carbon atoms,

when A 2 has a substituent, the substituent of A 2 is an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, a cyano group, a halogen atom, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms or a monocyclic aromatic heterocyclic group having 2 to 30 ring carbon atoms,

X 1 and X 2 are each a linking group and independently represent a single bond, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or substituted or unsubstituted fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms,

when X 1 has a substituent and/or X 2 has a substituent, the substituent for X 1 and X 2 is an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, a cyano group, a halogen atom, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms, or a monocyclic aromatic heterocyclic group having 2 to 30 ring carbon atoms,

Y 1 , Y 3 and Y 4 each independently represent a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 2 to 30 ring carbon atoms, or a substituted or unsubstituted fused aromatic heterocyclic group having 2 to 30 ring carbon atoms,

Y 2 represents a hydrogen atom, a fluorine atom, a cyano group, an unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted haloalkyl group having 1 to 20 carbon atoms, an unsubstituted haloalkoxy group having 1 to 20 carbon atoms, an unsubstituted alkylsilyl group having 1 to 10 carbon atoms, an unsubstituted arylsilyl group having 6 to 30 carbon atoms, an unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, an unsubstituted fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms, an unsubstituted aromatic heterocyclic group having 2 to 30 ring carbon atoms, or an unsubstituted fused aromatic heterocyclic group having 2 to 30 ring carbon atoms,

adjacent ones of Y 1 to Y 4 are optionally bonded to each other to form a ring structure,

p and q represent an integer of 1 to 4, and r and s represent an integer of 1 to 3, and

when p and q are an integer of 2 to 4 and r and s are an integer of 2 to 3, a plurality of Y 1 to Y 4 may be the same or different,

(Cz − ) a A 3   (5)

where:

Cz represents a substituted or unsubstituted arylcarbazolyl group or carbazolylaryl group;

A 3 represents a group represented by a formula (7A) below; and

a represents an integer of 1 to 3,

(M 1 ) c − (L 5 ) d − (M 2 ) e   (7A)

where:

M 1 and M 2 each independently represent a substituted or unsubstituted nitrogen-containing fused aromatic heterocyclic ring having 2 to 40 ring carbon atoms, M 1 and M 2 being optionally the same or different;

L 5 represents a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted fused aromatic hydrocarbon group having 10 to 30 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, or a substituted or unsubstituted fused aromatic heterocyclic group having 2 to 30 carbon atoms; and

c represents an integer of 0 to 2, d represents an integer of 1 to 2, and e represents an integer of 0 to 2 with a proviso that c+e is 1 or more.

2. The organic electroluminescence device according to claim 1 , wherein the first host material is represented by a formula (2) below,

where, A 1 , A 2 , X 1 , X 2 , Y 1 to Y 4 , p, q, r, and s are the same as A 1 , A 2 , X 1 , X 2 , Y 1 to Y 4 , p, q, r, and s in the formula (4).

3. The organic electroluminescence device according to claim 1 , wherein A 1 is selected from the group consisting of a substituted or unsubstituted pyridine ring, substituted or unsubstituted pyrimidine ring and substituted or unsubstituted triazine ring.

4. The organic electroluminescence device according to claim 1 , wherein A 1 is a substituted or unsubstituted pyrimidine ring.

5. The organic electroluminescence device according to claim 1 , wherein the first host material is represented by a formula (3) below,

where: A 2 , X 1 , Y 1 to Y 4 , p, q, r, and s are the same as A 2 , X 1 , Y 1 to Y 4 , p, q, r, and s in the formula (4),

Y 5 represents an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, a cyano group, a halogen atom, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms, or an aromatic heterocyclic group having 2 to 30 ring carbon atoms,

t represents an integer in a range of 1 to 3; and

when t is an integer of 2 to 3, a plurality of Y 5 may be the same or different.

6. The organic electroluminescence device according to claim 1 , wherein A 1 is a substituted or unsubstituted quinazoline ring.

7. The organic electroluminescence device according to claim 1 , wherein X 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or substituted or unsubstituted fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms.

8. The organic electroluminescence device according to claim 1 , wherein X 1 is a single bond.

9. The organic electroluminescence device according to claim 1 , wherein A 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.

10. The organic electroluminescence device according to claim 1 , wherein:

in the formula (4), when A 1 has a substituent, the substituent of A 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms;

A 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms; and

when A 2 has a substituent, the substituent of A 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms.

11. The organic electroluminescence device according to claim 1 , wherein:

in the formula (4), when A 1 has a substituent, the substituent of A 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms;

Y 1 to Y 4 are each a hydrogen atom; and

when A 2 has a substituent, the substituent of A 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms.

12. The organic electroluminescence device according to claim 1 , wherein the phosphorescent material is an ortho-metalated complex of a metal atom selected from iridium (Ir), osmium (Os) and platinum (Pt).

13. The organic electroluminescence device according to claim 1 , wherein an electron injecting layer is provided between the cathode and the emitting layer, the electron injecting layer comprising a nitrogen-containing cyclic derivative.