IP Library Granted Patent US 8,541,111
Granted Patent B2
US 8,541,111 · App. 12/117,544 · Granted Sep 24, 2013

Organic electroluminescent device and display apparatus

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Quick Facts
Patent No.
US 8,541,111
App. No.
12/117,544
Granted
Sep 24, 2013
Kind
B2
Abstract

A red light-emitting organic electroluminescent device is provided and includes an anode; a cathode; and an organic layer which includes a light-emitting layer and is interposed between the anode and cathode. The light-emitting layer includes a red light-emitting guest material and a host material composed of a polycyclic aromatic hydrocarbon compound whose mother skeleton has a ring member number of from four to seven. The organic electroluminescent device also includes an electron transport layer containing a benzimidazole derivative provided adjacent to the light-emitting layer.

Claims (36)

1. A red light-emitting organic electroluminescent device comprising:

an anode;

a cathode;

an organic layer which includes a light-emitting layer and is interposed between the anode and cathode, the light-emitting layer including a red light-emitting guest material and a host material composed of a polycyclic aromatic hydrocarbon compound with a mother skeleton having a ring member number of from four to seven; and

an electron transport layer including a benzimidazole derivative represented by the following general formula (1) provided adjacent to the light-emitting layer

wherein

A 1 represents a hydrogen atom, a substituted or unsubstituted aryl group having not more than sixty carbon atoms, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkyl group having from one to twenty carbon atoms or an alkoxy group having from one to twenty carbon atoms;

A 2 represents a hydrogen atom, an unsubstituted aryl group having not more than sixty carbon atoms, an unsubstituted heterocyclic group, an unsubstituted alkyl group having from one to twenty carbon atoms or an alkoxy group having from one to twenty carbon atoms;

B represents a substituted or unsubstituted arylene group having not more than sixty carbon atoms, a pyridinylene group which may have a substituted or unsubstituted group, a quinolinylene group which may have a substituent or a fluorenylene group which may have a substituent; and

Ar represents a substituted or unsubstituted alkyl group having from one to twenty carbon atoms or a substituted or unsubstituted alkoxy group having from one to twenty carbon atoms.

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

the mother skeleton of the polycyclic aromatic hydrocarbon compound which configures the host material of the light-emitting layer is selected from the group consisting of pyrene, benzopyrene, chrysene, naphthacene, benzonaphthacene, dibenzonaphthacene, perylene and coronene.

3. The organic electroluminescent device according to claim 1 , wherein

a compound represented by the following general formula (2) is used as the host material of the light-emitting layer:

wherein R 1 to R 8 each independently represents hydrogen, a halogen, a hydroxyl group, a substituted or unsubstituted carbonyl group having not more than twenty carbon atoms, a substituted or unsubstituted carbonyl ester group having not more than twenty carbon atoms, a substituted or unsubstituted alkyl group having not more than twenty carbon atoms, a substituted or unsubstituted alkenyl group having not more than twenty carbon atoms, a substituted or unsubstituted alkoxyl group having not more than twenty carbon atoms, a cyano group, a nitro group, a substituted or unsubstituted silyl group having not more than thirty carbon atoms, a substituted or unsubstituted aryl group having not more than thirty carbon atoms, a substituted or unsubstituted heterocyclic group having not more than thirty carbon atoms or a substituted or unsubstituted amino group having not more than thirty carbon atoms.

4. The organic electroluminescent device according to claim 1 , wherein the electron transport layer has a stack structure including a plurality of layers.

5. The organic electroluminescent device according to claim 1 , wherein the electron transport layer has a layer formed by subjecting plural kinds of the benzimidazole derivative to simultaneous vapor deposition.

6. A display apparatus comprising:

a substrate; and

a plural number of red light-emitting organic electroluminescent devices provided on the substrate and including

an anode,

a cathode,

an organic layer which includes a light-emitting layer and is interposed between the anode and cathode, the light-emitting layer including a red light-emitting guest material and a host material composed of a polycyclic aromatic hydrocarbon compound whose mother skeleton has a ring member number of from four to seven; and

an electron transport layer containing a benzimidazole derivative represented by the following general formula (1) provided adjacent to the light-emitting layer

wherein

A 1 represents a hydrogen atom, a substituted or unsubstituted aryl group having not more than sixty carbon atoms, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkyl group having from one to twenty carbon atoms or an alkoxy group having from one to twenty carbon atoms;

A 2 represents a hydrogen atom, an unsubstituted aryl group having not more than sixty carbon atoms, an unsubstituted heterocyclic group, an unsubstituted alkyl group having from one to twenty carbon atoms or an alkoxy group having from one to twenty carbon atoms;

B represents a substituted or unsubstituted arylene group having not more than sixty carbon atoms, a pyridinylene group which may have a substituted or unsubstituted group, a quinolinylene group which may have a substituent or a fluorenylene group which may have a substituent; and

Ar represents a substituted or unsubstituted alkyl group having from one to twenty carbon atoms or a substituted or unsubstituted alkoxy group having from one to twenty carbon atoms.

7. The display apparatus according to claim 6 , wherein the organic electroluminescent device is provided as a red light-emitting device in a part of plural pixels.

8. The display apparatus according to claim 6 , wherein a blue light-emitting, organic electroluminescent device and a green light-emitting, organic electroluminescent device are provided together with the red light-emitting device on the substrate.

9. The organic electroluminescent device according to claim 1 , wherein the guest material is represented by the following formula (106)

10. The organic electroluminescent device according to claim 1 , wherein the guest material is represented by the following formula (107)

11. The organic electroluminescent device according to claim 1 , wherein the guest material is represented by the following formula (108)

12. The organic electroluminescent device according to claim 1 , wherein the guest material is represented by the following formula (109)

13. The organic electroluminescent device according to claim 1 , wherein the host material is represented by the following formula (103)

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 18, 2025
From: JDI DESIGN AND DEVELOPMENT G.K.
To: MAGNOLIA BLUE CORPORATION
Reel/Frame 072039/0656 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 31, 2024
From: JOLED, INC.
To: JDI DESIGN AND DEVELOPMENT G.K.
Reel/Frame 066382/0619 →
CORRECTION BY AFFIDAVIT FILED AGAINST REEL/FRAME 063396/0671 Recorded Jun 12, 2023
From: JOLED, INC.
To: JOLED, INC.
Reel/Frame 064067/0723 →
SECURITY INTEREST Recorded Apr 20, 2023
From: JOLED, INC.
To: INCJ, LTD.
Reel/Frame 063396/0671 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 15, 2015
From: SONY CORPORATION
To: JOLED INC.
Reel/Frame 036106/0355 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 12, 2008
From: KAMBE, EMIKO; MATSUNAMI, SHIGEYUKI; KIJIMA, YASUNORI
To: SONY CORPORATION
Reel/Frame 020933/0962 →