Organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-9748492-B2
Application number	US-201314069808-A
Country	US
Kind code	B2
Filing date	Nov 1, 2013
Priority date	Nov 2, 2012
Publication date	Aug 29, 2017
Grant date	Aug 29, 2017

Abstract

Provided are an amine compound having a benzofluorene structure and further having a dibenzofuran structure and/or a dibenzothiophene structure, and an organic electroluminescent device containing a cathode, an anode and an organic thin film layer intervening between the cathode and anode, the organic thin film layer comprising one layer or plural layers comprising at least an emitting layer, at least one layer of the organic thin film layer comprising the aforementioned amine compound solely or as a component of a mixture.

First claim

What is claimed is:

1. An amine compound represented by the following formula (1):
B A) n   (1)

wherein in the formula (1),
n represents an integer of from 2 to 4;
B represents a structure represented by the following formula (2); and
A represents an amine moiety represented by the following formula (4),
plural moieties represented by A may be the same as or different from each other,

wherein in the formula (2),
at least one combination among combinations of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 represents a bond to a divalent group represented by the following formula (3); and
R 9 and R 10 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having from 5 to 30 ring atoms,

wherein in the formula (3),
* represents a bonding position to one combination in the formula (2), which shows a bond to the divalent group represented by the formula (3),

in the formulae (2) and (3),
n group(s) among R 1 to R 8 and R 11 to R 14 each represent a bond to the moiety represented by A; and
the others of R 1 to R 8 and R 11 to R 14 than as described above each independently represent a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having from 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having from 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having from 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having from 5 to 30 ring atoms,

wherein in the formula (4),
Ar 1 represents a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having from 5 to 30 ring carbon atoms;
L 1 and L 2 each independently represent a single bond, an arylene group having from 6 to 30 ring carbon atoms, a heteroarylene group having from 5 to 30 ring atoms or a divalent linking group formed by bonding 2 to 4 of these groups;
any one among R 21 to R 28 represents a bond to the group represented by L 2 , and the others thereof each independently represent a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having from 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having from 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having from 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having from 5 to 30 ring atoms, or members of one or more combinations selected among combinations of R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 26 and R 27 , and R 27 and R 28 are bonded to each other to form a saturated or unsaturated ring structure;
X represents an oxygen atom or a sulfur atom; and
** represents a bonding position to the structure represented by B.

2. The amine compound according to claim 1 , wherein in the formula (1), B represents any one of the following formulae (11) to (13):

wherein R 1 to R 14 are the same as in the formulae (2) and (3).

3. The amine compound according to claim 1 , wherein in the formula (2), two combinations among combinations of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 each represent a bond to a divalent group represented by the formula (3).

4. The amine compound according to claim 1 , wherein in the formula (1), B represents any one of the following formulae (14) to (19):

wherein R 1 to R 14 are the same as in the formulae (2) and (3), and R 11′ to R 14′ have the same meanings as R 11 to R 14 , respectively.

5. The amine compound according to claim 4 , wherein in the formula (1), B represents any one of the formulae (14) to (16).

6. The amine compound according to claim 1 , wherein in the formula (1), X represents an oxygen atom.

7. The amine compound according to claim 1 , wherein in the formula (4), L 1 represents a single bond.

8. The amine compound according to claim 1 , wherein in the formula (4), L 2 represents a single bond.

9. The amine compound according to claim 1 , wherein in the formula (4), R 24 or R 25 represents a bond to the group represented by L 2 .

10. The amine compound according to claim 1 , wherein in the formula (1), n represents 2.

11. The amine compound according to claim 1 , wherein in the formula (4), Ar 1 represents a substituted or unsubstituted phenyl, naphthyl or biphenylyl group.

12. An organic electroluminescent device comprising a cathode, an anode and an organic thin film layer intervening between the cathode and anode, the organic thin film layer containing one layer or plural layers containing at least an emitting layer, at least one layer of the organic thin film layer containing the amine compound according to claim 1 solely or as a component of a mixture.

13. The organic electroluminescent device according to claim 12 , wherein the emitting layer comprises the amine compound.

14. The organic electroluminescent device according to claim 12 , wherein the at least one layer of the organic thin film layer contains the amine compound according to claim 1 and an anthracene derivative represented by the following formula (5):

wherein in the formula (5),
Ar 11 and Ar 12 each independently represent a substituted or unsubstituted monocyclic group having from 5 to 50 ring atoms or a substituted or unsubstituted condensed ring group having from 8 to 50 ring atoms; and
R 101 to R 108 each independently represent a group selected from a hydrogen atom, a substituted or unsubstituted monocyclic group having from 5 to 50 ring atoms, a substitu

Assignees

• Idemitsu Kosan Co

Inventors

• Ito Hirokatsu
• Ikeda Takeshi

Classifications

• H01L51/0058

  Electricity · mapped topic

• H01L51/0054

  Electricity · mapped topic

• H01L51/5056

  Electricity · mapped topic

• H01L51/0055

  Electricity · mapped topic

• H01L51/006 Primary

  Electricity · mapped topic