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Materials for Organic Electroluminescent Devices

A technology of electronic devices and main materials, applied in 4 fields, can solve problems such as low conjugation, difficulty in handling cleaning equipment, and difficulty in purification

Active Publication Date: 2015-12-02
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 1. The service life is still very short, especially in the case of blue or green emission, which means that only simple industrial applications have been possible so far
[0004] 2. In some cases, the compounds used are only sparingly soluble in common organic solvents, which makes their purification during synthesis more difficult and also makes handling the material from solution and cleaning equipment in the manufacture of electronic devices difficulty
However, due to the usual linkage (2,2′-position or 2,7-position), they always contain a para-linked biphenyl bridging group, thus resulting in the lowest conjugation, which reduces the bandgap adaptability

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

[0095] Example 1: Synthesis of 4,4'-bis(naphthalene-1-yl)-1,1'-dimethoxy-9,9'-spirobifluorene

[0096]

[0097] In 300ml toluene, 100ml di 25.5 g (120 mmol) of tripotassium phosphate in a mixture of alkanes and 400 ml of water, 913 mg (3 mmol) of tri-o-tolylphosphine, and then 112 mg (0.5 mmol) of palladium (II) acetate were added to well-stirred 26.7 g (50 mmol) of 4,4 '-Dibromo-1,1'-dimethoxy-9,9'-spirobifluorene and 22.4g (130mmol) of 1-naphthaleneboronic acid in suspension, and then the mixture was heated to reflux for 16h. After cooling, the precipitated solid was filtered off with suction, washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, volume:volume), and three times with 100 ml of ethanol, then removed from DMF (about 10 ml / g) was recrystallized three times. Yield: 20 g (31 mmol), 65.0%, purity: 99.9% (HPLC).

Embodiment 2

[0098] Example 2: Synthesis of 4,4'-bis(naphthalene-1-yl)-9,9'-spirobifluorene

[0099]

[0100] Mix well stirred 31.5g (50mmol) 4,4'-bis(naphthalene-1-yl)-1,1'-dimethoxy-9,9'-spirobifluorene, 18.1g (100mmol) 1-benzene Base-5-chlorotetrazole and 27.6g (200mmol) K 2 CO 3 The suspension was heated to reflux in 250ml acetone for 18h. After cooling, the precipitated solid was filtered off with suction and dried. The solid was dissolved in 200 ml of toluene, 6 g of 5% Pd / C was added, and the mixture was stirred at 40° C. under hydrogen atmosphere for 8 h. After removal of the solvent, the residue was washed three times with 50 ml ethanol:water (1:1, v:v), three times with 100 ml ethanol, and then recrystallized three times from DMF (about 10 ml / g). Yield: 18.7 g (33 mmol), 69.0%, purity: 99.9% (HPLC).

Embodiment 3

[0101] Example 3: Synthesis of 4,4'-bis(diphenylamino)-1,1'-dimethoxy-9,9'-spirobifluorene

[0102]

[0103] Add 190 μL (1 mmol) di-tert-butylphosphine chloride, then 112 mg (0.5 mmol) palladium(II) acetate to 19.7 g (37 mmol) 4,4′-dibromo-1,1′-dimethoxy-9 , 9'-spirobifluorene, 10.2g (60mmol) of diphenylamine and 7.7g (80mmol) of sodium tert-butoxide in 500ml of toluene suspension, and then the mixture was heated to reflux for 5h. After cooling to 60° C., 500 ml of water were added, the organic phase was separated off, filtered through silica gel, evaporated to near dryness in vacuo at 80° C., and then 300 ml of ethanol were added. After cooling, the solids were filtered off with suction. from two Alkanes (about 8ml / g) recrystallized five times. Yield: 18.8 g (26.5 mmol), 72%, purity 87% (HPLC).

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Abstract

The present invention relates to 4,4′-substituted spirobifluorenes which are suitable, owing to excellent properties, as functional materials in organic electroluminescent devices. In addition, the present invention relates to a process for the preparation of 4,4′-substituted spirobifluorenes and to the use of these compounds in organic electroluminescent devices.

Description

technical field [0001] The present invention relates to 4,4'-substituted spirobifluorenes, which are suitable as functional materials in organic electroluminescent devices due to their excellent properties. In addition, the invention relates to processes for the preparation of 4,4'-substituted spirobifluorenes and the use of these compounds in organic electroluminescent devices. Background technique [0002] The general structure of organic electroluminescent devices is described, for example, in US4539507, US5151629, EP0676461 and WO98 / 27136. However, there is still a need to improve these devices: [0003] 1. The still short lifetime, especially in the case of blue or green emission, means that only simple industrial applications have been possible so far. [0004] 2. In some cases, the compounds used are only sparingly soluble in common organic solvents, which makes their purification during synthesis more difficult and also makes handling the material from solution and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06H05B33/14C07C13/72H01L51/50H01L51/00H10K99/00
CPCC09K11/06C07C13/72C07C43/21C07C49/665C07C211/61C07C217/94C07C2103/94C07D209/86C07D235/20C07D241/48C07D251/24C07D265/38C07D333/08C07D333/16C07D403/10C07D471/10C07F9/5325C09B1/00C09B23/14C09B57/00C09B57/008C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1059C09K2211/1092C09K2211/185H01L51/0059H01L51/0067H01L51/5016H01L51/5048H05B33/14Y02E10/549Y10S428/917C07C2603/94H10K85/631H10K85/654H10K50/14H10K50/11H10K2101/10
Inventor 埃米尔·侯赛因·帕勒姆苏珊·霍伊恩埃斯特·布罗伊宁
Owner MERCK PATENT GMBH
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