IP Library Granted Patent US 9,728,727
Granted Patent B2
US 9,728,727 · App. 13/964,203 · Granted Aug 8, 2017

Organic electroluminescence device and organic light emitting medium

Inventors: Masahide Matsuura (Chiba, JP); Masakazu Funahashi (Chiba, JP); Kenichi Fukuoka (Chiba, JP); Chishio Hosokawa (Chiba, JP)
Assignee: IDEMITSU KOSAN CO., LTD.
H01L51/0058C07C13/567C07C13/72C07C15/28C07C15/30C07C15/38C07C15/52C09K11/06H01L51/006H01L51/0052H01L51/0054H01L51/0072H05B33/14B82Y30/00C07C2103/46C07C2103/50C09K2211/1007C09K2211/1011C09K2211/1014H01L51/0055H01L51/0056H01L51/0059H01L51/0062H01L51/5012H01L51/5024H01L51/5052H01L51/5206H01L51/5221Y10S428/917Y10S977/755
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Quick Facts
Patent No.
US 9,728,727
App. No.
13/964,203
Granted
Aug 8, 2017
Kind
B2
Abstract

An organic electroluminescence device having a layer of an organic light emitting medium which comprises (A) a specific arylamine compound and (B) at least one compound selected from specific anthracene derivatives, spirofluorene derivatives, compounds having condensed rings and metal complex compounds and is disposed between a pair of electrodes and an organic light emitting medium comprising the above components (A) and (B) are provided. The organic electroluminescence device exhibits a high purity of color, has excellent heat resistance and a long life and efficiently emits bluish to yellowish light. The organic light emitting medium can be advantageously used for the organic electroluminescence device.

Claims (67)

1. An electroluminescence device comprising a pair of electrodes and a layer of an organic light emitting medium disposed between the pair of electrodes, wherein the layer of an organic light emitting medium comprises:

(A) at least one arylamine compound of formula (V):

wherein:

X 3 is an unsubstituted pyrene residue;

each of Ar 5 and Ar 6 is independently a substituted or unsubstituted aromatic group selected from the group consisting of a phenyl group, a naphthyl group, an anthranyl group, a phenanthryl group, a pyrenyl group, a coronyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a furanyl group, a thienyl group, a benzothienyl group, an indolyl group, and a carbazolyl group;

p is 2; and

(B) at least one anthracene derivative of formula (I):

A 1 -L-A 2   (I)

wherein:

A 1 and A 2 may be the same or different and each of A 1 and A 2 is independently a substituted or unsubstituted monophenylanthryl group or a substituted or unsubstituted diphenylanthryl group; and

L is a single bond or a divalent bonding group; and

a weight ratio of component (A) to component (B) is from 1:99 to 20:80.

2. The electroluminescence device according to claim 1 , wherein the anthracene derivative is of formula (I-a):

wherein:

each of R 1 to R 10 is independently a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group which may be substituted, an alkoxyl group, an aryloxyl group, an alkylamino group, an alkenyl group, an arylamino group, or a heterocyclic group which may be substituted:

each of a and b is an integer of 1 to 5

when each of a and b represents an integer of 2 or greater, atoms or groups represented by a plurality of R 1 and R 2 may be the same or different and may be bonded to each other to form a ring;

groups represented by combinations of R 3 and R 4 , R 5 and R 6 , R 7 and R 8 , and R 9 and R 10 may be bonded to each other to form a ring; and

L 1 is a single bond, —O—, —S—, —N(R)— wherein R is an alkyl group or an aryl group which may be substituted, an alkylene group, or an arylene group.

3. The electroluminescence device according to claim 1 , wherein the anthracene derivative is of formula (I-b):

wherein:

each of R 11 to R 20 is independently a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group which may be substituted, an alkoxyl group, an aryloxyl group, an alkylamino group, an arylamino group, or a heterocyclic group which may be substituted:

each of c, d, e, and f is an integer of 1 to 5;

when each of c, d, e, and f represents an integer of 2 or greater, atoms or groups represented by a plurality of R 11 , R 12 , R 16 , and R 17 may be the same or different and may be bonded to each other to form a ring;

groups represented by combinations of R 13 and R 14 , and R 18 and R 19 may be bonded to each other to form a and

L 2 is a single bond, —O—, —S—, —N(R)— wherein R is an alkyl group or an aryl group which may be substituted, an alkylene group, or an arylene group.

4. The electroluminescence device according to claim 1 , wherein a layer of a chalcogenide, a layer of a metal halide, or a layer of a metal oxide is disposed on at least one surface of the pair of electrodes.

5. The electroluminescence device according to claim 1 , wherein a mixed region comprising a reducing dopant and organic substances or a mixed region comprising an oxidizing dopant and organic substances is disposed on at least one surface of the pair of electrodes.

6. The electroluminescence device according to claim 1 , wherein a thickness of the layer of an organic light emitting medium is from 10 to 40 nm.

7. The electroluminescence device of claim 1 , wherein at least one of Ar 5 and Ar 6 is a substituted or unsubstituted terphenyl group.

8. The electroluminescence device of claim 1 , wherein each of Ar 5 and Ar 6 is independently a substituted or unsubstituted group selected from the group consisting of a phenyl group and a biphenyl group.

9. The electroluminescence device of claim 1 , wherein each of Ar 5 and Ar 6 is a substituted or unsubstituted phenyl group.

10. The electroluminescence device of claim 1 , wherein each optional substituent of Ar 5 and Ar 6 is independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkoxyl group having 1 to 6 carbon atoms, an aryloxyl group having 5 to 18 carbon atoms, an aralkyloxyl group having 7 to 18 carbon atoms, an arylamino group having 5 to 16 carbon atoms, a nitro group, a cyano group, an ester group having 1 to 6 carbon atoms, and a halogen atom.

11. The electroluminescence device of claim 1 , wherein each optional substituent of Ar 5 and Ar 6 is independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a cyano group, and a halogen atom.

12. The electroluminescence device of claim 1 , wherein each optional substituent of Ar 5 and Ar 6 is independently selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group.

13. The electroluminescence device of claim 1 , wherein:

each of Ar 5 and Ar 6 is independently a substituted or unsubstituted group selected from the group consisting of a phenyl group and a biphenyl group; and

each optional substituent of Ar 5 and Ar 6 is independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a cyano group, and a halogen atom.

14. The electroluminescence device of claim 1 , wherein:

at least one of Ar 5 and Ar 6 is a substituted or unsubstituted terphenyl group; and

each optional substituent of Ar 5 and Ar 6 is independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a cyano group, and a halogen atom.

15. The electroluminescence device of claim 1 , wherein:

each of A 5 and Ar 6 is independently a substituted or unsubstituted group selected from the group consisting of a phenyl group and a biphenyl group; and

each optional substituent of A 5 and Ar 6 is independently selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group.

16. The electroluminescence device of claim 1 , wherein:

at least one of Ar 5 and Ar 6 is a substituted or unsubstituted terphenyl group; and

each optional substituent of Ar 5 and Ar 6 is independently selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group.

17. The electroluminescence device of claim 1 , wherein:

each of Ar 5 and Ar 6 is a substituted or unsubstituted phenyl group; and

each optional substituent of Ar 5 and Ar 6 is independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a cyano group, and a halogen atom.

18. The electroluminescence device of claim 1 , wherein:

each of Ar 5 and Ar 6 is a substituted or unsubstituted phenyl group; and

each optional substituent of Ar 5 and Ar 6 is independently selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group.

19. The electroluminescence device of claim 1 , wherein:

each of A 5 and Ar 6 is a substituted or unsubstituted terphenyl group; and

at least one of Ar 5 and Ar 6 is a substituted terphenyl group substituted with a halogen atom.

20. The electroluminescence device of claim 1 , wherein:

each of Ar 5 and Ar 6 is a substituted or unsubstituted terphenyl group; and

at least one of Ar 5 and Ar 6 is a substituted terphenyl group substituted with a fluorine atom.

21. The electroluminescence device of claim 1 , wherein:

each of Ar 5 and Ar 6 is independently a substituted or unsubstituted group selected from the group consisting of a phenyl group and a biphenyl group; and

each optional substituent of Ar 5 and Ar 6 is independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a cyano group.

22. The electroluminescence device of claim 1 , wherein:

each of A 5 and Ar 6 is independently a substituted or unsubstituted group selected from the group consisting of a phenyl group and a biphenyl group; and

each optional substituent of Ar 5 and Ar 6 is independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms and a cyano group.

23. The electroluminescence device of claim 22 , wherein each of Ar 5 and Ar 6 is a substituted or unsubstituted phenyl group.

24. The electroluminescence device of claim 22 , wherein each of Ar 5 and Ar 6 is a substituted or unsubstituted biphenyl group.

Priority Claims (1)
JP 2002-211308 · Jul 19, 2002 · national
Continuity (5)
Continuation 13675037 · Nov 13, 2012
Division 12773307 · May 4, 2010
Continuation 11207933 · Aug 22, 2005
Division 10617397 · Jul 11, 2003
Related Publication 20130328030A1 · Dec 12, 2013