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Materials for Organic Electroluminescent Devices

A technology of electronic devices and devices, which is applied in the field of indenofluorene derivatives, can solve problems such as low efficiency, blocking vapor deposition sources, blocking, etc.

Active Publication Date: 2015-12-16
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 1. Efficiency is still low, especially in the case of fluorescent OLEDs, and should be improved
[0004] 2. Usually the service life is still short, especially in the case of blue light emission, so there is a need for further improvement at this point
[0007] 5. Some materials of the prior art, especially hole transport materials, have the problem that they crystallize at the edge of the vapor deposition source during vapor deposition, thus blocking said vapor deposition source
However, these compounds have the problem that, due to the crystallinity of the material, they show problematic behavior during vapor deposition in mass production, since the material crystallizes on the vapor deposition source during vapor deposition and blocks it
Therefore, the use of these materials in production is accompanied by increased technical complexity

Method used

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  • Materials for Organic Electroluminescent Devices
  • Materials for Organic Electroluminescent Devices
  • Materials for Organic Electroluminescent Devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103] Example 1: Synthesis of Amine-1

[0104] a) Synthesis of (2'-nitrophenyl) fluoren-2-yl derivatives

[0105]

[0106] Make 164.4g (650mmol) 9,9-dimethyl-9H-fluorene-2-boronic acid, 33.8g (124mmol) 2,5-dibromonitrobenzene and 164.7g (774mmol) K 2 CO 3 Suspended in 750ml THF and 750ml water, the mixture was washed with N 2 Saturation, 2.9 g (2.55 mmol) of tetrakis(triphenylphosphine)palladium(0) were added, and the mixture was heated at the boil for 2 h. The mixture was poured into 3 L of a 1:1:1 mixture of water / MeOH / 6M HCl and filtered with suction to remove a beige precipitate, which was washed with water and dried. according to 1 The product content determined by H-NMR was about 75%, and the total yield was 183 g (90%).

[0107] b) Synthesis of dibromo derivatives

[0108]

[0109] 384 g (973 mmol) of the compound from a) were first introduced under protective gas into 2.5 L of chloroform and cooled to 5°C. To this solution, 55.2ml (1071mmol) of Br dissolv...

Embodiment 2

[0119] Embodiment 2: synthetic amine-2

[0120] a) Synthesis of thioethers

[0121]

[0122] Make the K 2 CO 3 Suspended in 850ml THF and 850ml water, with N 2 The mixture was saturated, 3.3 g (2.9 mmol) of tetrakis(triphenylphosphine)palladium(0) were added and the mixture was heated at the boil for 2 h. The mixture was poured into 3 L of a 1:1:1 mixture of water / MeOH / 6M HCl and filtered with suction to remove a beige precipitate, which was washed with water and dried. according to 1 The product content determined by H-NMR was about 95%, and the total yield was 190 g (82%).

[0123] b) Oxidation of sulfides

[0124]

[0125]196 g (619.3 mmol) of the thioether from a) were first introduced under protective gas into 2.3 L of glacial acetic acid and 250 ml of dichloromethane and cooled to 0°C. To this solution was added dropwise 1.1 L (619 mmol) of 30% H 2 o 2 solution, and the mixture was stirred overnight. Na 2 SO 3 The solution was added to the mixture, the ...

Embodiment 3 to 8

[0141] Examples 3 to 8: Fabrication of OLEDs

[0142] The OLEDs of the invention were produced by the general method according to WO 04 / 058911, which was adapted to the conditions described here (layer-thickness variation, materials used).

[0143] Results for various OLEDs are given in Examples 3 to 8 below. A glass plate coated with structured ITO (indium tin oxide) forms the matrix of the OLED. For improved processing, 20 nm of PEDOT (poly(3,4-ethylenedioxy-2,5-thiophene), applied by spin coating from water, purchased from H.C. Starck, Goslar, Germany) was applied to the substrate superior. The OLED consists of the following sequential layers: substrate / PEDOT 20nm / HIL 15nm / hole transport layer (HTM) 20, 110 or 200nm / NPB 20nm / emissive layer (EML) 30nm / electron transport layer (ETM) 20nm and finally the cathode.

[0144] Materials other than PEDOT were applied by thermal vapor deposition in a vacuum chamber. The emitting layer here always consists of a matrix material (ho...

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Abstract

The present invention relates to indenofluorene derivatives containing heteroaromatic bridge atoms as a novel class of materials with light-emitting and hole-transport properties, particularly for use in light-emitting and / or charge-transport layers of electroluminescent devices. The present invention also relates to methods of preparing the compounds of the present invention, and to electronic devices comprising the compounds.

Description

technical field [0001] The present invention describes indenofluorene derivatives containing heteroaromatic bridging atoms as a novel class of materials with light-emitting and hole-transporting properties, especially for use in light-emitting and / or charge-transporting layers of electroluminescent devices . The invention also relates to processes for preparing the compounds of the invention, and to electronic devices comprising the compounds. Background technique [0002] The general structure of organic electroluminescent devices is described, for example, in US4539507, US5151629, EP0676461 and WO98 / 27136. However, these devices still need improvement: [0003] 1. Efficiency is still low, especially in the case of fluorescent OLEDs, and should be improved. [0004] 2. Generally, the service life is still short, especially in the case of blue light emission, so there is a need for further improvement at this point. [0005] 3. The operating voltage is rather high not on...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06
CPCC09K11/06C09K2211/1022C09K2211/1029C09K2211/1044C09K2211/1092H05B33/14C09B17/00C09B19/00C09B57/00C09B57/008Y02E10/549H10K85/6576H10K85/6572H10K50/15C07D209/82
Inventor 埃米尔·侯赛因·帕勒姆克里斯托夫·普夫卢姆阿尔内·比辛霍尔格·海尔菲利普·施特塞尔
Owner MERCK PATENT GMBH
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