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Materials for Organic Electroluminescent Devices

A technology of general formula and compound, applied in the field of materials for organic electroluminescent devices, can solve the problems of low efficiency, blocking vapor deposition source, difficult realization, etc.

Active Publication Date: 2011-12-14
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 fluorescent OLED case, should be improved
[0004] 2. Usually the service life is very short, especially in the case of blue light, so there is still a need for improvement at this point
[0005] 3. The operating voltage is quite high, especially in the case of fluorescent OLEDs
However, with state-of-the-art materials, this can only be achieved with difficulty due to the concomitant increase in voltage
[0007] 5. In this regard, some prior art materials show the problem of crystallizing at the edge of the vapor deposition source during vapor deposition and clogging the vapor deposition source
However, these compounds have a problem in mass production that due to the crystallinity of the material, the material crystallizes on the vapor deposition source during vapor deposition and clogs the vapor deposition source
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

[0146] a) Synthesis of thioethers

[0147]

[0148] 200g (732mmol) 2-bromo-9,9-dimethyl-9H-fluorene, 122.9g (732mmol) 2-methylsulfanylphenylboronic acid and 202g (950mmol) K 2 CO 3 Suspended in 850ml THF and 850ml water, the mixture was washed with N 2 After saturation, 3.3 g (2.9 mmol) of tetrakis(triphenylphosphine)palladium(0) were added and the mixture was heated at the boil for 2 hours. The mixture was poured into 3 L of a 1:1:1 mixture of water / MeOH / 6M HCl, the beige precipitate was filtered off with suction, 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%).

[0149] b) oxidation

[0150]

[0151] First 196 g (619.3 mmol) of the compound from a) were 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 overn...

Embodiment 2-9

[0161] Examples 2-9: Fabrication of OLEDs

[0162] The inventive OLEDs are produced by the general method according to WO 04 / 058911, which is adapted to the conditions described here (layer-thickness variation, materials used).

[0163] Results for various OLEDs are given in Examples 2 to 9 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 / HIL1 5nm / hole transport layer (HTM) 20, 110 or 200nm / NPB 20nm / emissive layer (EML) 30 or 40nm / electron transport layer (ETM) 20nm and finally of the cathode.

[0164] Materials other than PEDOT were applied by thermal vapor deposition in a vacuum chamber. The emitting layer here always consists of a matrix material (host...

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Abstract

The present invention describes indenofluorene derivatives of the general formula I, II, III or IV having emitting and hole-transporting properties, in particular for use in the emission and / or charge-transport layer of electro-luminescent devices. The invention furthermore relates to a process for the preparation of the compounds according to the invention and to electronic devices comprising same.

Description

technical field [0001] The present invention describes, in particular for use in light-emitting and / or charge-transport layers in electroluminescent devices, as a novel class of materials with light-emitting and hole-transporting properties heteroaromatic bridge atoms containing amines para to the bridge atoms Indenofluorene derivatives. The present invention also relates to processes for the preparation of the compounds of the invention and electronic devices comprising the compounds. Background technique [0002] The general structure of organic electroluminescent devices is described, for example, in US 4539507, US 5151629, EP 0676461 and WO 98 / 27136. However, there is still a need to improve these devices: [0003] 1. Efficiency is still low, especially in the case of fluorescent OLEDs, and should be improved. [0004] 2. Usually the service life is very short, especially in the case of blue light, so there is still a need for improvement at this point. [0005] 3. T...

Claims

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Application Information

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IPC IPC(8): C07D209/94C07D333/50C07D333/76C07D333/78C07D401/04C07D403/04C07D403/14C07D409/04C07D409/14C07D413/04C07D413/14C07D487/04C07D495/04C07F9/6553C07D401/14
CPCC09B17/00C07D413/04C09K2211/1014H01L51/0072C07D403/14C07D409/14C07D401/14C09K2211/1092C09B57/008C07D209/94H01L51/0074C07D409/04H01L51/5016H01L51/0059C09K2211/1033H05B33/14C07D333/78C07D333/76C09K11/06C09B57/00H01L51/5012C07D403/04C07D487/04C09K2211/1011C07D401/04C07D495/04C09K2211/1029H01L51/5048C07D333/50C09B15/00C07D413/14C09B19/00Y02E10/549C07F9/655354H10K85/631H10K85/6576H10K85/6572H10K50/14H10K50/11H10K2101/10
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·施托塞尔
Owner MERCK PATENT GMBH
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