Tetraaryl benzidines

• US 5,639,914 A
• Filed: 11/01/1994
• Issued: 06/17/1997
• Est. Priority Date: 11/01/1993
• Status: Expired due to Term

• Current Assignee: Hodogaya Chemical Co., Ltd, JOLED Inc.
• Original Assignee: Hodogaya Chemical Co., Ltd, Matsushita Electric Industrial Company Limited (Panasonic Holdings Corporation)
• Inventors: Oshino, Masahiko, Nakanishi, Naoko, Tomiyama, Hiromitsu, Ihara, Ikuko
• Primary Examiner(s): Raymond, Richard L.
• Application Number:
  US08/332,726
• Time in Patent Office: 959 Days
• Field of Search: 552/110, 564/50, 564/309
• US Class Current: 564/309
• CPC Class Codes: C07C 211/54 having amino groups bound to two or three six-membered aromatic rings
• CPC Class Codes: C07C 211/56 the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
• CPC Class Codes: C07C 211/61 with at least one of the condensed ring systems formed by three or more rings
• CPC Class Codes: C07C 217/84 the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
• CPC Class Codes: C07C 217/92 the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 225/22 having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 2603/18 Fluorenes; Hydrogenated fluorenes
• CPC Class Codes: C07C 275/40 being further substituted by nitrogen atoms not being part of nitro or nitroso groups
• CPC Class Codes: C07C 317/36 with the nitrogen atoms of the amino groups bound to hydrogen atoms or to carbon atoms
• CPC Class Codes: C07C 323/37 the sulfur atom of the sulfide group being further bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: Y10S 428/917 Electroluminescent
• CPC Class Codes: Y10T 428/31504 Composite [nonstructural laminate]
• CPC Class Codes: Y10T 428/31678 Of metal
• CPC Class Codes: Y10T 428/31692 Next to addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31909 Next to second addition polymer from unsaturated monomers

Abstract

The present invention provides novel amine compounds useful as electron-transporting materials to be incorporated in organic electro-luminescence devices. More particularly, the present invention provides an organic electro-luminescence device (organic EL device) which can find wide application in various display units, requires a low applied voltage and exhibits a high luminance and an excellent stability.

Claims

1. A compound, represented by any one of the following formulae (I) to (V):

##STR59## wherein R₁₁ and R₁₂ may be the same or different and each represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, an unsubstituted phenyl group, or a phenyl group having a lower alkyl group or a lower alkoxy group as a substituent(s), with the proviso that at least one of R₁₁ and R₁₂ is a phenyl group, or a phenyl group having a lower alkyl group or a lower alkoxy group; and

R₁₃ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a chlorine atom;

##STR60## wherein R₂₁, R₂₂ and R₂₃ may be the same or different and each represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, an unsubstituted phenyl group, or a phenyl group having a lower alkyl group or a lower alkoxy group as a substituent(s);

R₂₄ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a chlorine atom; and

A₁ represents a group represented by any one of the following structural formulae (a1) to (i1);

##STR61## in which R₂₅ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a chlorine atom;

##STR62## wherein R₃₁, R₃₂ and R₃₃ may be the same or different and each represent a hydrogen atom, a lower alkyl group, or a lower alkoxy group, an unsubstituted phenyl group, or a phenyl group having a lower alkyl group or a lower alkoxy group as a substituent(s);

R₃₄ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a chlorine atom; and

A₂ represents a group represented by any one of the following formulae (j1) to (n1);

##STR63## wherein R₄₁ and R₄₂ may be the same or different and each represent a hydrogen atom, a lower alkyl group, or a lower alkoxy group, an unsubstituted phenyl group, or a phenyl group having a lower alkyl group or a lower alkoxy group as a substituent(s);

R₄₃ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a chlorine atom; and

A₃ represents a group represented by any one of the following structural formulae (a2) to (i2);

##STR64## in which R₄₄ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a chlorine atom;

##STR65## wherein R₅₁ and R₅₂ may be the same or different and each represent a hydrogen atom, a lower alkyl group, or a lower alkoxy group, an unsubstituted phenyl group or a phenyl group having a lower alkyl group or a lower alkoxy group as a substituent(s);

R₅₃ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a chlorine atom; and

A₄ represents a group represented by any one of the following structural formulae (j2) to (n2);

##STR66##

2. The compound of claim 1, of the formula (I).

3. The compound of claim 1, of the formula (II).

4. The compound of claim 1, of the formula (III).

5. The compound of claim 1, of the formula (IV).

6. The compound of claim 1, of the formula (V).