Organic compound, charge-transporting material, composition containing the compound, organic electroluminescent element, display device, and lighting device

Patent metadata

Field	Value
Publication number	US-9564602-B2
Application number	US-201414547614-A
Country	US
Kind code	B2
Filing date	Nov 19, 2014
Priority date	Apr 7, 2011
Publication date	Feb 7, 2017
Grant date	Feb 7, 2017

Abstract

The invention provides an organic compound incorporating a specific structure into a pyridine skeleton or a 1,3,5-triazine skeleton and adapting the molecular weight to a specific range, a composition comprising the organic compound and a solvent, organic electroluminescent element comprising a layer that is formed by using the composition, and the uses thereof.

First claim

The invention claimed is:

1. An organic compound which is represented by formula (1), has a molecular weight of 750 or more and 2,000 or less, and has one or no carbazolyl group in the molecule:

wherein
A, B, and C each independently are selected from substituents represented by formulae (2-1) to (2-5):
—Ar 1 —X 1   (2-1)

—Ar 2 —Ar 3 —X 2   (2-2)

—Ar 4 —Ar 5 —Ar 6 —X 3   (2-3)

—Ar 7 —Ar 8 —Ar 9 —Ar 10 —X 4   (2-4)

—Ar 11 —Ar 12 —Ar 13 —Ar 14 —Ar 15 —X 5   (2-5)

wherein Ar 1 represents a 1,2-phenylene group or 1,3-phenylene group, which may have a substituent R, Ar 2 to Ar 15 each independently represent a 1,3-phenylene group, or 1,4-phenylene group, which may have a substituent,
X 1 represents an aromatic hydrocarbon group which has 10 or more carbon atoms and may have a substituent R, or a carbazolyl group which may have a substituent R, and X 2 to X 5 each independently represent an aromatic hydrocarbon group which may have a substituent R, a carbazolyl group which may have a substituent R,
R represents a phenyl group which may have a substituent R′, an alkyl group, a silyl group, a fluorine atom, or a perfluoroalkyl group,
R′ represents an alkyl group, a silyl group, a fluorine atom, or a perfluoroalkyl group,
with the proviso that A, B, and C each contain at least one of a 1,2-phenylene group and a 1,3-phenylene group, and that A, B, and C are a different substituent from each other; and
D represents CH or a nitrogen atom.

2. The organic compound according to claim 1 , wherein in formulae (2-1) to (2-5), the substituents represented by Ar 1 , Ar 3 , Ar 6 , Ar 10 , and Ar 15 are 1,3-phenylene groups.

3. A charge-transporting material which comprises the organic compound according to claim 1 .

4. A composition which comprises the organic compound according to claim 1 and a solvent.

5. An organic electroluminescent element which comprises an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein at least one of the organic layers is a layer formed from the composition according to claim 4 .

6. An organic electroluminescent element comprising, an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein at least one of the organic layers is a layer formed from a composition comprising the organic compound according to claim 1 and a solvent, wherein the layer formed from the composition comprising the organic compound and the solvent is a luminescent layer.

7. A display device which comprises an organic electroluminescent element which comprises an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein at least one of the organic layers is a layer formed from a composition comprising the organic compound according to claim 1 and a solvent.

8. A lighting device which comprises an organic electroluminescent element which comprises an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein at least on of the organic layers is a layer formed from a composition comprising the organic compound according to claim 1 and a solvent.

9. A composition which comprises the organic compound according to claim 2 and a solvent.

10. An organic electroluminescent element which comprises an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein at least one of the organic layers is a layer formed from the composition according to claim 9 .

11. The organic compound according to claim 1 , wherein in formulae (2-1) to (2-5), Ar 1 represents a unsubstituted 1,3-phenylene group, Ar 2 to Ar 15 each independently represent a unsubstituted 1,3-phenylene group, or unsubstituted 1,4-phenylene group,
X 1 represents an unsubstituted aromatic hydrocarbon group which has 10 or more carbon atoms, or an unsubstituted carbazolyl group, and X 2 and X 5 each independently represent an unsubstituted aromatic hydrocarbon group, an unsubsituted carbazolyl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothienyl group.

12. An organic compound which is represented by formula (1), has a molecular weight of 750 or more and 2,000 or less, and has one or no carbazolyl group in the molecule:

wherein
A, B, and C each independently are selected from substituents represented by formulae (2-1) to (2-5):
—Ar 1 —X 1   (2-1)

—Ar 2 —Ar 3 —X 2   (2-2)

—Ar 4 —Ar 5 —Ar 6 —X 3   (2-3)

—Ar 7 —Ar 8 —Ar 9 —Ar 10 —X 4   (2-4)

—Ar 11 —Ar 12 —Ar 13 —Ar 14 —Ar 15 —X 5   (2-5)

wherein Ar 1 represents a 1,2-phenylene group or 1,3-phenylene group, which may have a substituent R, Ar 2 to Ar 15 each independently represent a 1,3-phenylene group, or 1,4-phenylene group, which may have a substituent,
X 1 represents an aromatic hydrocarbon group which has 10 or more carbon atoms and may have a substituent R, or a carbazolyl group which may have a substituent R, and X 2 to X 5 each independently represent an aromatic hydrocarbon group which may have a substituent R, a carbazolyl group which may have a substituent R,
R represents a phenyl group which may have a substituent R′, an alkyl group, a silyl group, a fluorine atom, or a perfluoroalkyl group,
R′represents an alkyl group, a silyl group, a fluorine atom, or a perfluoroalkyl group,
with the proviso that A, B, and C each contain at least one of a 1,2-phenylene group and a 1,3-phenylene group, and that A, B, and C do not simultaneously represent the same group; and
D represents a nitrogen atom.

Assignees

• Mitsubishi Chem Corp

Inventors

• Ishibashi Koichi
• Gorohmaru Hideki
• Shimizu Wataru
• Okamoto Tomomi

Classifications

• C07D405/14

  containing three or more hetero rings · CPC title

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• H01L51/0072

  Electricity · mapped topic

• H01L51/0085

  Electricity · mapped topic

• H01L51/5012

  Electricity · mapped topic