IP Library Granted Patent US 8,779,655
Granted Patent B2
US 8,779,655 · App. 12/167,725 · Granted Jul 15, 2014

Organic electroluminescence device and material for organic electroluminescence device

Inventors: Kazuki Nishimura (Sodegaura, JP); Toshihiro Iwakuma (Sodegaura, JP); Kenichi Fukuoka (Sodegaura, JP); Chishio Hosokawa (Sodegaura, JP); Masahiro Kawamura (Sodegaura, JP); Mitsunori Ito (Sodegaura, JP); Yoriyuki Takashima (Sodegaura, JP); Toshinari Ogiwara (Sodegaura, JP)
Assignee: Idemitsu Kosan Co., Ltd.
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Quick Facts
Patent No.
US 8,779,655
App. No.
12/167,725
Granted
Jul 15, 2014
Kind
B2
Abstract

An organic electroluminescence device includes: a cathode; an anode; and a single-layered or multilayered organic thin-film layer provided between the cathode and the anode. The organic thin-film layer includes at least one emitting layer. The at least one emitting layer contains at least one phosphorescent material and a host material represented by the following formula (1). Ra—Ar 1 —Rb  (1) In the formula, Ar 1 , Ra and Rb each represent a substituted or unsubstituted benzene ring or a condensed aromatic hydrocarbon ring selected from a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted chrysene ring, a substituted or unsubstituted fluoranthene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted benzophenanthrene ring, a substituted or unsubstituted dibenzophenanthrene ring, a substituted or unsubstituted triphenylene ring, a substituted or unsubstituted benzo[a]triphenylene ring, a substituted or unsubstituted benzochrysene ring, a substituted or unsubstituted benzo[b]fluoranthene ring and a substituted or unsubstituted picene ring. Substituents for Ra and Rb are not aryl groups.

Claims (44)

1. An organic electroluminescence device, comprising:

a cathode;

an anode; and

a single-layered or multilayered organic thin-film layer provided between the cathode and the anode, wherein

the organic thin-film layer comprises at least one emitting layer, and

the at least one emitting layer comprises: at least one phosphorescent material; and a host material having excited triplet energy of of 2.0 eV to 2.8 eV, the host material represented by a formula (1) as follows,

Ra—Ar 1 —Rb  (1)

where:

Ar 1 represents a condensed aromatic hydrocarbon ring selected from a substituted or unsubstituted benzochrysene ring, and a substituted or unsubstituted picene ring;

Ra and Rb each represent a substituted or unsubstituted benzene ring or a condensed aromatic hydrocarbon ring selected from a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted chrysene ring, a substituted or unsubstituted fluoranthene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted benzophenanthrene ring, a substituted or unsubstituted dibenzophenanthrene ring, a substituted or unsubstituted benzochrysene ring, and a substituted or unsubstituted picene ring, wherein the substituents for Ra and Rb are not aryl groups,

wherein when Ra, Rb, or both are substituted with a substituent, the substituent is one or more of an alkyl group comprising 1 to 20 carbon atoms, a haloalkyl group comprising 1 to 20 carbon atoms, a cycloalkyl group comprising 5 to 18 carbon atoms, a silyl group comprising 3 to 20 carbon atoms, a cyano group, and a halogen atom,

wherein when Ar 1 is substituted with a substituent, the substituent is one or more of an aryl group comprising 6 to 22 carbon atoms, an alkyl group comprising 1 to 20 carbon atoms, a haloalkyl group comprising 1 to 20 carbon atoms, a cycloalkyl group comprising 5 to 18 carbon atoms, a silyl group comprising 3 to 20 carbon atoms, a cyano group, and a halogen atom.

2. The organic electroluminescence device according to claim 1 , wherein

the phosphorescent material comprises a metal complex, and

the metal complex comprises: a metal atom selected from Ir, Pt, Os, Au, Cu, Re and Ru; and a ligand.

3. The organic electroluminescence device according to claim 2 , wherein the ligand has an ortho-metal bond.

4. The organic electroluminescence device according to claim 1 , wherein a maximum wavelength of light emission of the at least one phosphorescent material contained in the emitting layer is in a range of 500 nm to 720 nm.

5. The organic electroluminescence device according to claim 1 , wherein

the organic thin-film layer comprises an electron transporting layer or an electron injecting layer between the cathode and the emitting layer, and

the electron transporting layer or the electron injecting layer comprises an aromatic ring having a nitrogen-containing six-membered or five-membered ring skeleton, or a condensed aromatic cyclic compound having a nitrogen-containing six-membered or five-membered ring skeleton.

6. The organic electroluminescence device according to claim 1 , wherein a reductive dopant is present at an interfacial region between the cathode and the organic thin-film layer.

7. The organic electroluminescence device according to claim 1 , wherein Ra, Rb, or both represent a substituted or unsubstituted naphthalene ring.

8. The organic electroluminescence device according to claim 1 , wherein Ra, Rb, or both represent a substituted or unsubstituted chrysene ring.

9. The organic electroluminescence device according to claim 1 , wherein Ra, Rb, or both represent a substituted or unsubstituted fluoranthene ring.

10. The organic electroluminescence device according to claim 1 , wherein Ra, Rb, or both represent a substituted or unsubstituted phenanthrene ring.

11. The organic electroluminescence device according to claim 1 , wherein Ra, Rb, or both each represent a substituted or unsubstituted benzophenanthrene ring.

12. The organic electroluminescence device according to claim 1 , wherein Ra, Rb, or both each represent a substituted or unsubstituted dibenzophenanthrene ring.

13. The organic electroluminescence device according to claim 1 , wherein Ra, Rb, or both represent a substituted or unsubstituted benzochrysene ring.

14. The organic electroluminescence device according to claim 1 , wherein Ra, Rb, or both represent a substituted or unsubstituted picene ring.

15. An organic electroluminescence device, comprising:

a cathode;

an anode; and

a single-layered or multilayered organic thin-film laver provided between the cathode and the anode, wherein

the organic thin-film layer comprises at least one emitting layer, and

the at least one emitting layer comprises: at least one phosphorescent material; and a host material having excited triplet energy of of 2.0 eV to 2.8 eV, the host material represented by a formula (1) as follows,

Ra—Ar 1 —Rb  (1)

where:

Ar 1 represents a condensed aromatic hydrocarbon ring selected from a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted dibenzophenanthrene ring, a substituted or unsubstituted benzochrysene ring, and a substituted or unsubstituted picene ring;

wherein Ra, Rb, or both represent a substituted or unsubstituted chrysene ring, a substituted or unsubstituted fluoranthene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted benzophenanthrene ring, a substituted or unsubstituted dibenzophenanthrene ring, a substituted or unsubstituted benzochrysene ring, and a substituted or unsubstituted picene ring, wherein the substituents for Ra and Rb are not aryl groups,

wherein when Ra, Rb, or both are substituted with a substituent, the substituent is one or more of an alkyl group comprising 1 to 20 carbon atoms, a haloalkyl group comprising 1 to 20 carbon atoms, a cycloalkyl group comprising 5 to 18 carbon atoms, a silyl group comprising 3 to 20 carbon atoms, a cyano group, and a halogen atom,

wherein when Ar 1 is substituted with a substituent, the substituent is one or more of an aryl group comprising 6 to 22 carbon atoms, an alkyl group comprising 1 to 20 carbon atoms, a haloalkyl group comprising 1 to 20 carbon atoms, a cycloalkyl group comprising 5 to 18 carbon atoms, a silyl group comprising 3 to 20 carbon atoms, a cyano group, and a halogen atom.

16. The organic electroluminescence device according to claim 15 , wherein Ar 1 is a substituted or unsubstituted naphthalene ring.

17. The organic electroluminescence device according to claim 15 , wherein Ar 1 is a substituted or unsubstituted benzochrysene ring.

18. The organic electroluminescence device according to claim 15 , wherein Ar 1 is a substituted or unsubstituted picene ring.

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE THIRD ASSIGNOR'S DOCUMENT DATE PREVIOUSLY RECORDED ON REEL 021648 FRAME 0620. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Oct 15, 2008
From: NISHIMURA, KAZUKI; IWAKUMA, TOSHIHIRO; FUKUOKA, KENICHI; HOSOKAWA, CHISHIO; KAWAMURA, MASAHIRO; ITO, MITSUNORI; TAKASHIMA, YORIYUKI; OGIWARA, TOSHINARI
To: IDEMITSU KOSAN CO., LTD.
Reel/Frame 021683/0963 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 8, 2008
From: NISHIMURA, KAZUKI; IWAKUMA, TOSHIHIRO; FUKUOKA, KENICHI; HOSOKAWA, CHISHIO; KAWAMURA, MASAHIRO; ITO, MITSUNORI; TAKASHIMA, YORIYUKI; OGIWARA, TOSHINARI
To: IDEMITSU KOSAN CO., LTD.
Reel/Frame 021648/0620 →
Priority Claims (3)
JP 2007-179109 · Jul 7, 2007 · national
JP 2007-179120 · Jul 7, 2007 · national
JP 2007-179121 · Jul 7, 2007 · national
Continuity (3)
Continuation In Part 12108066 · Apr 23, 2008
Provisional Application 61053908 · May 16, 2008
Related Publication 20090045730A1 · Feb 19, 2009