Organic electroluminescent materials

• US 6,737,532 B2
• Filed: 04/05/2002
• Issued: 05/18/2004
• Est. Priority Date: 05/08/2001
• Status: Expired due to Term

• Current Assignee: InnoLux Corporation
• Original Assignee: CHI MEI Optoelectronics Corporation, Kyocera Corporation
• Inventors: Chung, Jun-Wen, Chen, Ruey-Min
• Primary Examiner(s): Lambkin, Deborah C.
• Application Number:
  US10/117,408
• Publication Number:
  US 20020195930A1
• Time in Patent Office: 774 Days
• Field of Search: 548/156, 548/219
• US Class Current: 548/156
• CPC Class Codes: C07D 209/60 Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
• CPC Class Codes: C07D 277/64 with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
• CPC Class Codes: H10K 50/00 Organic light-emitting devices integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36
• CPC Class Codes: H10K 50/131 with spacer layers between the electroluminescent layers
• CPC Class Codes: H10K 85/114 Poly-phenylenevinylene; Derivatives thereof
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/652 Cyanine dyes
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons

Abstract

An organic electroluminescent compound of the formula (I)

wherein:

X₁ is selected from the group consisting of oxygen, sulfur, C(CH₃)₂ and N—R, wherein R is hydrogen, alkyl of from 1 to 20 carbon atoms or aryl; and

Ar₁ and Ar₂ are individually aryl or heterocyclic systems.

Applying the compound to an electroluminescent (EL) device provides a highly efficient blue and green emitting organic EL device.

Claims

1. An organic electroluminescent compound of the formula (I):

wherein;

X₁ is selected from the group consisting of oxygen, sulfur, C(CH₃)₂ and N—

R,

wherein R is hydrogen, alkyl of from 1 to 20 carbon atoms or aryl; and

Ar₁ is an aryl or heterocyclic system, and Ar₂ is selected from the group consisting of substituted or unsubstituted biphenylene, substituted or unsubstituted triphenylene, substituted or unsubstituted terephenylene, substituted or unsubstituted bithiophene, substituted or unsubstituted trithiophene, substituted or unsubstituted terephenylene, substituted or unsubstituted arylene vinylene, substituted or unsubstituted carbazole, substituted or unsubstituted arylamino group, and substituted or unsubstituted carbocyclic aromatic group.

2. The organic electroluminescent compound as claimed in claim 1, wherein Ar₁ is shown as:

wherein;

R₁, R₂, R₃ and R₄ are individually selected from the group consisting of hydrogen, halogen, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted thioalkyl group, substituted or unsubstituted arylene group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted arylamino group, substituted or unsubstituted carbocyclic aromatic group, substituted or unsubstituted heterocyclic aromatic group, nitro group, and cyano group.

5. The organic electroluminescent compound as claimed in claim 1, wherein changing a symmetry of Ar₂ changes a wavelength of emitted light.

6. The organic electroluminescent compound as claimed in claim 1, wherein changing a composition of Ar₂ changes a wavelength of emitted light.

3. An organic electroluminescent compound of the formula(II):

wherein;

X₂ and X₃ are individually selected from the group consisting of oxygen, sulfur, C(CH₃)₂ and N—

R, wherein R is hydrogen, alkyl of from 1 to 20 carbon atoms or aryl; and

Ar₁ and Ar₃ are individually aryl or heterocyclic systems, and Ar₂ is selected from the group consisting of substituted or unsubstituted triphenylene, substituted or unsubstituted terephenylene, substituted or unsubstituted bithiophene, substituted or unsubstituted trithiophene, substituted or unsubstituted terephenylene, substituted or unsubstituted arylene vinylene, substituted or unsubstituted carbazole, substituted or unsubstituted arylamino group, substituted or unsubstituted carbocyclic aromatic group, and substituted or unsubstituted heterocyclic aromatic group.

4. The organic electroluminescent compound as claimed in claim 3, wherein Ar₁ and Ar₃ are shown as:

wherein;

R₁, R₂, R₃ and R₄ are individually selected from the group consisting of hydrogen, halogen, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted thioalkyl group, substituted or unsubstituted arylene group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted arylamino group, substituted or unsubstituted carbocyclic aromatic group, substituted or unsubstituted heterocyclic aromatic group, nitro group, and cyano group.

7. The organic electroluminescent compound as claimed in claim 3, wherein changing a symmetry of Ar₂ changes a wavelength of emitted light.

8. The organic electroluminescent compound as claimed in claim 3, wherein changing a composition of Ar₂ changes a wavelength of emitted light.