Monoamine compound, charge transport material, composition for charge transport film, organic electroluminescent element, organic EL display, and organic EL lighting

• US 9,985,214 B2
• Filed: 07/17/2014
• Issued: 05/29/2018
• Est. Priority Date: 08/27/2009
• Status: Active Grant

• Current Assignee: Mitsubishi Chemical Corporation (Mitsubishi Chemical Group Corp.)
• Original Assignee: Mitsubishi Chemical Corporation (Mitsubishi Chemical Group Corp.)
• Inventors: Baba, Tatsushi, Iida, Koichiro
• Primary Examiner(s): Murray, Jeffrey H
• Application Number:
  US14/334,262
• Publication Number:
  US 20140330025A1
• Time in Patent Office: 1,412 Days
• Field of Search: None
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07D 403/14 containing three or more hetero rings
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: H05B 33/10 Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6574 comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

A monoamine compound characterized by being represented by the following general formula (1).

[In general formula (1), R¹ to R³ each independently represent a phenyl group which may have a substituent in at least one of o- and m-positions, in which the substituent may be bonded to each other to form a cyclic structure. R¹ to R³ are a group different from each other.]

Claims

1. A monoamine compound represented by formula (1):

4. The monoamine compound according to claim 1, wherein when one or more of R¹ to R³ independently represent a group other than a phenyl group having as a substituent an aromatic heterocyclic group which may have a substituent, R¹ to R³ each independently represent a phenyl group having as a substituent an aromatic hydrocarbon group which may have a substituent.

5. The monoamine compound according to claim 1, wherein a difference between a carbon number of the group having the greatest carbon numbers among R¹ to R³ and a carbon number of the group having the second greater carbon numbers among R¹ to R³ is 5 or more.

6. The monoamine compound according to claim 1, wherein a difference between a carbon number of the group having the smallest carbon numbers among R¹ to R³ and a carbon number of the group having the second greater carbon numbers among R¹ to R³ is 5 or more.

7. The monoamine compound according to claim 5, wherein a difference between a carbon number of the group having the smallest carbon numbers among R¹ to R³ and a carbon number of the group having the second greater carbon numbers among R¹ to R³ is 5 or more.

10. The monoamine compound according to claim 1, wherein at least one of R¹ to R³ comprises a partial structure represented by formula (2-1):

11. The monoamine compound according to claim 1, wherein in formula (1), R¹ to R³ each independently are a phenyl group which may have a substituent in an m-position.

12. The monoamine compound according to claim 1, wherein in formula (1), at least one of R¹ to R³ is a group including a partial structure represented by formula (2-2):

13. The monoamine compound according to claim 12, wherein the partial structure represented by formula (2-2) is a partial structure represented by formula (3):

14. The monoamine compound according to claim 1, wherein in formula (1) at least one of R¹ to R³ is a group represented by the following formula (11):

15. The monoamine compound according to claim 1, which has a solubility in m-xylene of 5% by mass or more at 25°

C. and atmospheric pressure.

16. The monoamine compound according to claim 1, wherein R¹ to R³ each independently represent a phenyl group which may have as substituents one or more aromatic hydrocarbon groups or aromatic heterocyclic groups.

2. A monoamine compound represented by formula (1):

8. The monoamine compound according to claim 2, wherein when one or more of R¹ to R³ independently represent a group other than a phenyl group having as a substituent an aromatic heterocyclic group which may have a substituent, R¹ to R³ each independently represent a phenyl group having as a substituent an aromatic hydrocarbon group which may have a substituent.

17. The monoamine compound according to claim 2, wherein R¹ to R³ each independently represent a phenyl group which may have as substituents one or more aromatic hydrocarbon groups or aromatic heterocyclic groups.

3. A monoamine compound represented by formula (1):

9. The monoamine compound according to claim 3, wherein when one or more of R¹ to R³ independently represent a group other than a phenyl group having as a substituent an aromatic heterocyclic group which may have a substituent, R¹ to R³ each independently represent a phenyl group having as a substituent an aromatic hydrocarbon group which may have a substituent.

18. The monoamine compound according to claim 3, wherein R¹ to R³ each independently represent a phenyl group which may have as substituents one or more aromatic hydrocarbon groups or aromatic heterocyclic groups.