Use of an organic matrix material for producing an organic semiconductor material, organic semiconductor material and electronic component

• US 7,540,978 B2
• Filed: 08/03/2005
• Issued: 06/02/2009
• Est. Priority Date: 08/05/2004
• Status: Active Grant

• Current Assignee: Novaled AG
• Original Assignee: Novaled AG
• Inventors: Blochwitz-Nimoth, Jan, Salbeck, Josef, Pfeiffer, Martin, Lux, Andrea
• Primary Examiner(s): Kopec; Mark
• Assistant Examiner(s): Thomas; Jaison P
• Application Number:
  US11/196,491
• Publication Number:
  US 20060049397A1
• Time in Patent Office: 1,399 Days
• Field of Search: 252/500, 257/40, 257/103, 313/503, 313/504, 136/263
• US Class Current: 252/500
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• 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: 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 50/14 Carrier transporting layers
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

The present invention relates to use of an organic matrix material for producing an organic semiconductor material, characterized in that the organic matrix material is comprised at least partly of a spirobifluorene compound, and the glass transition temperature of the organic matrix material is at least 120° C. and the highest occupied molecular orbital (HOMO) of the matrix material is at a maximum energy level of 5.4 eV; and also to an organic semiconductor material and electronic component.

Claims

1. Organic semiconductor material containing a hole transport layer of an organic matrix material doped with an organic dopant by coevaporation characterized in that the organic matrix material comprises at least partly one or more spiro-bifluorene compounds of the formula (I)

2. Organic semiconductor material according to claim 1, characterized in that the dopant is 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane or a derivative thereof.

3. Organic semiconductor material according to claim 1, characterized in that the molar doping ratio of dopant to matrix material is between 1:

1 and 1;

10.000.

4. Electronic component having an organic semiconductor material containing a hole transport layer of an organic matrix material doped with an organic dopant by coevaporation, characterized in that the organic matrix material is comprised at least partly of a spiro-bifluorene compound of the formula (I)

5. Electronic component according to claim 4 in the form of an organic light-emitting diode (OLED), a photovoltaic cell, an organic solar cell, an organic diode or an organic field-effect transistor.

6. Method for preparing an organic semiconductor or material comprising a hole transport layer, the method comprising producing the hole transport layer by co-evaporating and applying by vapor deposition a dopant and an organic matrix material, wherein the organic matrix material is comprised at least partly of a spiro-bifluorene compound of the formula (I)

7. Method according to claim 6, wherein the spirobifluorene compound is selected from the group consisting of:

8. Method of claim 6, characterized in that the glass transition temperature of the spiro-bifluorene compound lies between 120°

C. and 250°

C., and the highest occupied molecular orbital of the compound lies at an energy level between 4.5 eV and 5.4 eV.

9. Method according to claim 8, characterized in that the highest occupied molecular orbital of the compound lies between 4.8 eV and 5.2 eV.