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Formulations and electronic devices

A technology for electronic devices and preparations, which is applied in the field of manufacturing the electronic devices, and can solve the problems of reduced performance and lifespan, preparation, low solubility, etc.

Active Publication Date: 2013-01-09
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the aforementioned small molecule-containing devices cannot usually be fabricated in this way due to the low solubility of non-polymers in conventional solvents.
Although the solubility of these compounds can be improved by modification, the obtained electronic devices show reduced performance and lifetime compared to those obtained by vapor deposition

Method used

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  • Formulations and electronic devices
  • Formulations and electronic devices
  • Formulations and electronic devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0399] Embodiment 1: the synthesis of compound 3 and 4

[0400]

[0401] Synthesis of compound 3

[0402] 40.0g (146mmol) of 3-dihydroxyboryl-[3,1′;5,1″]terphenyl 2, 18.8g (146mmol) of 1-iodo-3-bromophenyl (1) and 109.3g (730mmol ) potassium carbonate was suspended in 1350ml toluene and 1150ml water. 844mg (0.73mmol) tetrakis (triphenylphosphine) palladium (0) was added in this suspension, and this reaction mixture was heated under reflux for 16 hours. After cooling, The organic phase was separated off, washed three times with 200 ml of water, dried over sodium sulfate, and then evaporated to dryness. The residue was washed with ethanol, recrystallized from ethyl acetate, and finally dried under reduced pressure. Yield is 47.6 g (123 mmol), corresponding to 84.5% of theory.

[0403] Synthesis of Compound 4

[0404]40.0g (104mmol) 1-bromo-3-([3,1′; 5,1″]terphenyl-1-yl)benzene 3, 29.0g (114mmol) bispinacolate diboron, 29.5g ( 301mmol) of potassium acetate was suspended in...

Embodiment 2

[0406] Synthesis of compound 5

[0407]

[0408] 74.7g (150mmol) of bis (3,5-dibromophenyl) ketone, 109.7g (900mmol) of phenylboronic acid, 267.5g (1162mmol) of tripotassium phosphate monohydrate, 5.5g (18mmol) of three O-tolylphosphine and 673.5 mg (3 mmol) of palladium (II) acetate were suspended in 600 ml of toluene, 300 ml of di a mixture of alkanes and 750 ml of water and heated at reflux for 72 hours. After cooling, the organic phase is separated off, washed three times with water and dried over sodium sulfate. The mixture was then filtered through alumina, evaporated to about 200 ml, and 500 ml of ethanol were added, whereby the crude product precipitated. The solid was filtered off with suction, washed with 100 ml of ethanol, dissolved in boiling toluene and reprecipitated by adding hot ethanol. The yield is 44.0 g (90 mmol), corresponding to 60.2% of theory.

Embodiment 3

[0409] Embodiment 3: the synthesis of compound 6

[0410]

[0411] The synthesis was carried out analogously to compound 5, wherein phenylboronic acid was replaced by 1-bromo-3-([3,1′;5,1″]-terphenyl-1-yl)benzene 3. The yield was 123.2 g (88 mmol), corresponding to 58.7% of theory.

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Abstract

The present invention relates to a formulation, comprising at least one solvent and at least two functional compounds of the general formula (I), wherein A is a functional structural element, B is a solubility-promoting structural element, and k is an integer in the range of 1 to 20, the molecular weight of the functional compound is at least 550 g / mol, and the solubility-promoting structural element B corresponds to the general formula (L-I), wherein Ar1 and Ar2 are an aryl or heteroaryl group independently of each other, which aryl or heteroaryl group can be substituted with one or more arbitrary groups R, each instance of X is N or CR2, preferably CH, independently of each other, R1 and R2, independently of each other, are hydrogen, a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkyoxy, or thioalkoxy group having 3 to 40 C atoms or a silyl group or a substituted keto group having 1 to 40 C atoms, an alkoxy carbonyl group having 2 to 40 C atoms, an aryloxy carbonyl group having 7 to 40 C atoms, a cyano group (-CN), a carbamoyl group (-C(=O)NH2), a haloformyl group (-C(=O)-X, wherein X represents a halogen atom), a formyl group (-C(=O)-H), an isocyano group, an isocyanate group, a thiocyanate group, or a thioisocyanate group, a hydroxy group, a nitro group, a CF3 group, Cl, Br, F, a group that can be cross-linked, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of said systems, wherein one or more of the groups R1 and / or R2 can form a mono- or polycyclic, aliphatic, or aromatic ring system with each other and / or with the ring to which the group R1 is bonded; and I is 0, 1, 2, 3, or 4; wherein the dashed bond indicates the bond to the functional structural element A. The present invention further relates to electronic devices that contain mixtures of said compounds.

Description

technical field [0001] The present invention relates to formulations for the manufacture of electronic devices. The invention also relates to electronic devices and to methods for manufacturing said electronic devices. Background technique [0002] Electronic devices comprising organic, organometallic and / or polymeric semiconductors are increasing in importance; for reasons of cost and because of their properties, they are used in many commodities. Examples that may be mentioned here are organic-based charge-transport materials (e.g. triarylamine-based hole transporters) in copiers, organic or polymer light-emitting diodes (OLED or PLED) in display devices, or in Organic photoreceptors in copiers. Organic solar cell (O-SC), organic field effect transistor (O-FET), organic thin film transistor (O-TFT), organic integrated circuit (O-IC), organic optical amplifier and organic laser diode (O-laser) are in the Advanced stage of development and can achieve major importance in t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00H01L51/54H01L51/46H01L51/30H01L51/00H10K99/00
CPCY02E10/549C07C2603/24C07C2603/42C07C15/30C07C15/38C07F5/025C07F7/0812C07F9/65683C07F9/65685C07F9/65848C07F15/0033C07F15/0086C09D139/04C09K11/06C09K2211/1007C09K2211/1011C09K2211/1059C09K2211/185H10K85/1135H10K85/622H10K85/626H10K85/615H10K85/342H10K2102/103H10K50/171H10K50/17H10K50/15H10K50/16H10K50/18H10K71/12H10K85/60H10K85/151H10K85/654H10K85/6572
Inventor 雷米·马努克·安米安苏珊·霍伊恩托马斯·埃伯利菲利普·施特塞尔奥雷莉·吕德曼迪特马尔·孔克尔
Owner MERCK PATENT GMBH