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

An organic electroluminescence device comprising:

• a cathode;
• an anode;
• and a plurality of organic thin-film layers provided between the cathode and the anode, the organic thin-film layers comprising an emitting layer, wherein
• at least one of the organic thin-film layers comprises a biscarbazole derivative represented by a formula (1A) or (1B) below,
• wherein:
• A1 represents a substituted or unsubstituted nitrogen-containing heterocyclic group selected from the group consisting of a substituted or unsubstituted pyridine ring, substituted or unsubstituted pyrimidine ring, substituted or unsubstituted triazine ring and substituted or unsubstituted quinazoline ring, when A1 has a substituent, the substituent of A1 is an alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkylsilyl group having 1 to 10 carbon atoms, arylsilyl group having 6 to 30 ring carbon atoms, cyano group, halogen atom, aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms;
• A2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, when A2 has a substituent, the substituent of A2 is an alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkylsilyl group having 1 to 10 carbon atoms, arylsilyl group having 6 to 30 ring carbon atoms, cyano group, halogen atom, aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms;
• X1 and X2 each are 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 X1 and X2 each have a substituent, the substituent of X1 and X2 is an alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkylsilyl group having 1 to 10 carbon atoms, arylsilyl group having 6 to 30 ring carbon atoms, cyano group, halogen atom, aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms;
• Y1, Y3 and Y4 independently represent a hydrogen atom, fluorine atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 10 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, substituted or unsubstituted fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 2 to 30 ring carbon atoms, or substituted or unsubstituted fused aromatic heterocyclic group having 2 to 30 ring carbon atoms;
• Y2 represents a hydrogen atom, fluorine atom, cyano group, unsubstituted alkyl group having 1 to 20 carbon atoms, unsubstituted alkoxy group having 1 to 20 carbon atoms, unsubstituted haloalkyl group having 1 to 20 carbon atoms, unsubstituted haloalkoxy group having 1 to 20 carbon atoms, unsubstituted alkylsilyl group having 1 to 10 carbon atoms, unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, unsubstituted fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms, unsubstituted aromatic heterocyclic group having 2 to 30 ring carbon atoms, or unsubstituted fused aromatic heterocyclic group having 2 to 30 ring carbon atoms;
• adjacent ones of Y1 to Y4 are allowed to be bonded to each other to form a ring structure;
• p and q represent an integer of 1 to 4;
• r and s represent an integer of 1 to 3;
• 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 Y1 to Y4 are allowed to be the same or different;
• the alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, and alkylsilyl group having 1 to 10 carbon atoms for the substituent of A1, A2, X1 and X2, are linear, branched or cyclic;
• and
• the alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, haloalkoxy group having 1 to 20 carbon atoms, and alkylsilyl group having 1 to 10 carbon atoms for Y1, Y2, Y3 and Y4 are linear, branched or cyclic.

A biscarbazole derivative represented by a formula (1A) or (1B) below,

• wherein:
• A1 is represented by one of the following formulae (101) to (105);
• A2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, when A2 has a substituent, the substituent of A2 is an alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkylsilyl group having 1 to 10 carbon atoms, arylsilyl group having 6 to 30 ring carbon atoms, cyano group, halogen atom, aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms;
• X1 and X2 each are 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 X1 and X2 each have a substituent, the substituent of X1 and X2 is an alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkylsilyl group having 1 to 10 carbon atoms, arylsilyl group having 6 to 30 ring carbon atoms, cyano group, halogen atom, aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms;
• Y1, Y3 and Y4 independently represent a hydrogen atom, fluorine atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 10 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, substituted or unsubstituted fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 2 to 30 ring carbon atoms, or substituted or unsubstituted fused aromatic heterocyclic group having 2 to 30 ring carbon atoms;
• Y2 represents a hydrogen atom, fluorine atom, cyano group, unsubstituted alkyl group having 1 to 20 carbon atoms, unsubstituted alkoxy group having 1 to 20 carbon atoms, unsubstituted haloalkyl group having 1 to 20 carbon atoms, unsubstituted haloalkoxy group having 1 to 20 carbon atoms, unsubstituted alkylsilyl group having 1 to 10 carbon atoms, unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, unsubstituted fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms, unsubstituted aromatic heterocyclic group having 2 to 30 ring carbon atoms, or unsubstituted fused aromatic heterocyclic group having 2 to 30 ring carbon atoms;
• adjacent ones of Y1 to Y4 are allowed to be bonded to each other to form a ring structure;
• p and q represent an integer of 1 to 4;
• 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 Y1 to Y4 are allowed to be the same or different,
• in the formulae (101) to (105):
• Y and Y′ represent a hydrogen atom, fluorine atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 10 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, 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;
• Y and Y′ are the same or different;
• and
• * represents a bonding position to X1, and in the formula (105):
• u represents an integer of 1 to 5;
• when u is an integer of 2 to 5, a plurality of Y are the same or different;
• the alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, and alkylsilyl group having 1 to 10 carbon atoms for the substituent of A2, X1 and X2 are linear, branched or cyclic;
• and
• the alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, haloalkoxy group having 1 to 20 carbon atoms, and alkylsilyl group having 1 to 10 carbon atoms for Y1, Y2, Y3, Y4, Y and Y′ are linear, branched or cyclic.

An organic electroluminescence device comprising:

• a cathode;
• an anode;
• and a plurality of organic thin-film layers provided between the cathode and the anode, the organic thin-film layers comprising an emitting layer, wherein
• at least one of the organic thin-film layers comprises a biscarbazole derivative represented by a formula (1A) or (1B) below,
• wherein:
• A1 is represented by one of the following formulae (101) to (105);
• A2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, when A2 has a substituent, the substituent of A2 is an alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkylsilyl group having 1 to 10 carbon atoms, arylsilyl group having 6 to 30 ring carbon atoms, cyano group, halogen atom, aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms;
• X1 and X2 each are 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 X1 and X2 each have a substituent, the substituent of X1 and X2 is an alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkylsilyl group having 1 to 10 carbon atoms, arylsilyl group having 6 to 30 ring carbon atoms, cyano group, halogen atom, aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms;
• Y1, Y3 and Y4 independently represent a hydrogen atom, fluorine atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 10 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, substituted or unsubstituted fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 2 to 30 ring carbon atoms, or substituted or unsubstituted fused aromatic heterocyclic group having 2 to 30 ring carbon atoms;
• Y2 represents a hydrogen atom, fluorine atom, cyano group, unsubstituted alkyl group having 1 to 20 carbon atoms, unsubstituted alkoxy group having 1 to 20 carbon atoms, unsubstituted haloalkyl group having 1 to 20 carbon atoms, unsubstituted haloalkoxy group having 1 to 20 carbon atoms, unsubstituted alkylsilyl group having 1 to 10 carbon atoms, unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, unsubstituted fused aromatic hydrocarbon group having 10 to 30 ring carbon atoms, unsubstituted aromatic heterocyclic group having 2 to 30 ring carbon atoms, or unsubstituted fused aromatic heterocyclic group having 2 to 30 ring carbon atoms;
• adjacent ones of Y1 to Y4 are allowed to be bonded to each other to form a ring structure;
• p and q represent an integer of 1 to 4;
• 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 Y1 to Y4 are allowed to be the same or different,
• in the formulae (101) to (105):
• Y and Y′ represent a hydrogen atom, fluorine atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 10 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, 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;
• Y and Y′ are the same or different;
• and
• * represents a bonding position to X1, and in the formula (105):
• u represents an integer of 1 to 5;
• when u is an integer of 2 to 5, a plurality of Y are the same or different;
• the alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, and alkylsilyl group having 1 to 10 carbon atoms for the substituent of A2, X1 and X2 are linear, branched or cyclic;
• and
• the alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, haloalkoxy group having 1 to 20 carbon atoms, and alkylsilyl group having 1 to 10 carbon atoms for Y1, Y2, Y3, Y4, Y and Y′ are linear, branched or cyclic.