Organic light-emitting device using paracyclophane

• US 20040110027A1
• Filed: 12/04/2002
• Published: 06/10/2004
• Est. Priority Date: 12/04/2002
• Status: Active Grant

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Suzuki, Koichi, Chen, Jian Ping, Ueno, Kazunori
• Granted Patent: US 6,869,698 B2
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C07C 13/70 with a condensed ring system consisting of at least two, mutually uncondensed aromatic ring systems, linked by an annular structure formed by carbon chains on non-adjacent positions of the aromatic ring, e.g. cyclophanes
• CPC Class Codes: C07C 211/54 having amino groups bound to two or three six-membered aromatic rings
• CPC Class Codes: C07C 211/61 with at least one of the condensed ring systems formed by three or more rings
• CPC Class Codes: C07C 23/18 Polycyclic halogenated hydrocarbons
• CPC Class Codes: C07C 25/22 with condensed rings
• CPC Class Codes: C07C 2603/18 Fluorenes; Hydrogenated fluorenes
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1003 Carbocyclic compounds
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 85/60 Organic compounds having low molecular weight H10K85/10 - H10K85/50 take precedence
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

An organic light-emitting device (OLED) in which a paracyclophane or a paracyclophane derivative is used as the emissive layer and/or one or more of the charge transport layers, or as a host material for one or more of these layers.

Claims

1. An organic light emitting device comprising:

an emissive layer sandwiched between at least a cathode and an anode, wherein the emissive layer includes a paracyclophane or a paracyclophane derivative expressed according to the following general formula (I);

wherein Ar represents identical aromatics that are present optionally,

wherein R₁ to R₈ are present optionally, and

wherein each of R₁ to R₈ independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, nitro group or cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted alkoxycarbonyl group or carboxyl group.

2. An organic light emitting device according to claim 1, wherein if the Ar groups are present, they are para-bonded.

3. An organic light emitting device according to claim 1, wherein if the Ar groups are present, they are ortho-bonded.

4. An organic light emitting device according to claim 1, wherein said emissive layer is comprised of a functional light-emitting layer of the paracyclophane or paracyclophane derivative.

5. An organic light emitting device according to claim 1, wherein said emissive layer is comprised of a host material of the paracyclophane or paracyclophane derivative, together with a functional light-emitting dopant.

6. An organic light emitting device according to claim 1, wherein R₁ through R₈ are provided symmetrically.

7. An organic light emitting device according to claim 1, wherein R₁ through R8 are provided non-symmetrically.

8. An organic light emitting device comprising:

an emissive layer sandwiched between at least one charge transport layer and an anode and a cathode, wherein the charge transport layer includes a paracyclophane or paracyclophane derivative according to the following general formula (I);

wherein Ar represents identical aromatics that are present optionally,

wherein R₁ to R₈ are present optionally, and

wherein each of R₁ to R₈ independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, nitro group or cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted alkoxycarbonyl group or carboxyl group.

9. An organic light emitting device according to claim 8, wherein if the Ar groups are present, they are para-bonded.

10. An organic light emitting device according to claim 8, wherein if the Ar groups are present, they are ortho-bonded.

11. An organic light emitting device according to claim 8, wherein said charge transport layer is comprised of a functional charge transport layer of the paracyclophane or paracyclophane derivative.

12. An organic light emitting device according to claim 8, wherein said charge transport layer is comprised of a host material of the paracyclophane or paracyclophane derivative, together with a functional charge transport dopant.

13. An organic light emitting device according to claim 8, wherein the charge transport layer is an electron transport layer.

14. An organic light emitting device according to claim 8, wherein the charge transport layer is a hole transport layer.

15. An organic light emitting device according to claim 8, wherein R₁ through R₈ are provided symmetrically.

16. An organic light emitting device according to claim 8, wherein R₁ through R₈ are provided symmetrically.