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Materials for organic electroluminescent devices

A technology of conditions and groups, applied in the field of materials used in organic electroluminescent devices, can solve problems such as not disclosed

Active Publication Date: 2014-01-01
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no disclosure therein of compounds comprising bridged five-membered heteroaryl ring groups instead of six-membered heteroaryl ring groups

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 1a

[0184] Example 1a: 10-Bromo-8,8-dimethyl-8H-9-thio-11b-azacyclo[a]fluoranthene (Compound 1a)

[0185]

[0186] Step 1: Methyl 3-carbazol-9-ylthiophene-2-carboxylate

[0187] Under protective gas, 102g (420mmol) 3-phenyl-9H-carbazole, 92g (420mmol) methyl 3-bromothiophene-2-carboxylate, 24g (375mmol) copper powder, 104g (757mmol) potassium carbonate and 11g (42mmol) of 18-crown-6 was first introduced into 1200ml of DMF and heated at 130°C for 86 hours. The mixture was then evaporated, washed by stirring with hot heptane, and purified by chromatography (heptane:dichloromethane 1:1). The product was washed by stirring with hot hexanes and a solid was isolated. Yield: 121 g (397 mmol), 65% of theory, according to 1 The purity by H NMR is about 97%.

[0188] Step 2: 2-(3-carbazol-9-ylthiophen-2-yl)propan-2-ol

[0189] 85 g (277 mmol) of methyl 3-carbazol-9-ylthiophene-2-carboxylate were dissolved in 1700 ml of dry THF and degassed. The mixture was cooled to -78°C and 740 m...

Embodiment 2a

[0198] Example 2a: 3-Bromo-8,8-dimethyl-8H-9-thia-11b-azacyclo[a]fluoranthene (Compound 2a)

[0199]

[0200] Step 1: Methyl 3-(3-bromocarbazol-9-yl)thiophene-2-carboxylate

[0201] Cool 63.5g (207mmol) of 8,8-dimethyl-8H-9-thia-11b-azacyclopenta[a]fluoranthene in 2L DMF to -10°C, and add 37.3 g (207 mmol) NBS. The mixture was then allowed to reach room temperature and stirred at this temperature for 6 hours. 500ml of water was then added to the mixture, followed by CH 2 Cl 2 extract. The organic phase was washed with MgSO 4 Dry and remove solvent in vacuo. The solid was isolated by washing the product with stirring with hot toluene. Yield: 72 g (186 mmol), 90% of theory, according to 1 The purity by H NMR is about 97%.

[0202] Step 2: 2-[3-(3-Bromocarbazol-9-yl)thiophen-2-yl]propan-2-ol

[0203] 106 g (277 mmol) of methyl 3-(3-bromocarbazol-9-yl)thiophene-2-carboxylate were dissolved in 1700 ml of dry THF and degassed. The mixture was cooled to -78°C and 740 ml...

Embodiment 3a

[0210] Example 3a: 8,8-Dimethyl-8H-9-thia-11b-azo[a]fluoranthene-10-boronic acid (Compound 3a)

[0211]

[0212] Dissolve 85 g (233 mmol) of 10-bromo-8,8-dimethyl-8H-9-thia-11b-azacyclopenta[a]fluoranthene in 1400 ml of dry THF at -70 °C 121 ml (303 mmol) of a 2.5 M solution of n-butyllithium in cyclohexane were added dropwise, and after 1 hour 33 ml of trimethylborate (302 mmol) were added dropwise, the mixture was allowed to reach room temperature over the course of 1 hour, Removing the solvent, will be based on 1 H-NMR showed a homogeneous residue which was used in subsequent reactions without further purification. The yield is 69 g (207 mmol), corresponding to 90% of theory.

[0213] Compounds 3b-3o were obtained analogously:

[0214]

[0215]

[0216]

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Abstract

The present invention relates to compounds according to formula (1) and formula (2), which are suitable for use in electronic devices, in particular organic electroluminescent devices.

Description

technical field [0001] The present invention relates to materials for use in electronic devices, in particular in organic electroluminescent devices. Background technique [0002] The structure of organic electroluminescent devices (OLEDs) in which an organic semiconductor is used as functional material is described, for example, in US4539507, US5151629, EP0676461 and WO98 / 27136. The luminescent materials used here are increasingly organometallic complexes which exhibit phosphorescence rather than fluorescence (M.A. Baldo et al., Appl. Phys. Lett. 1999, 75, 4-6). For quantum mechanical reasons, up to four times higher energy and power efficiencies can be achieved using organometallic compounds as phosphorescent emitters. There is still a need for improvements in OLEDs in general, especially OLEDs exhibiting triplet emission (phosphorescence), for example in terms of efficiency, operating voltage and lifetime. This applies in particular to OLEDs which emit in the relatively...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D471/16C07D491/16C07D491/22C07D495/04C07D495/16C07D495/22C07D498/16C07D519/00C07F5/02C09K11/06H01L51/50H01L51/00
CPCC07D471/04H01L51/5072H01L51/0085C07D495/04H01L51/5096C07D519/00C09K2211/1033C09B57/00C07D491/16C09K11/06H01L2251/5384C09K2211/1044H01L51/5016H01L51/0067H01L51/50H01L51/0072C09B57/008H01L51/0071C07D495/16H01L51/006C07D491/22C09K2211/1037H01L51/0068C09K2211/1051C09K2211/185H01L51/0074H05B33/14C07D495/22H01L51/0087C07D498/16C09K2211/1059H01L51/0065C07D471/16C09K2211/1074C07F5/025C09K2211/1007C09K2211/1029C09K2211/1081C09K2211/1077H10K85/654H10K85/6576H10K85/657H10K85/6572H10K50/18H10K85/653H10K85/655H10K85/633H10K85/346H10K85/342H10K50/16H10K50/11H10K2101/10H10K2101/90C07D495/14
Inventor 伊里娜·马丁诺娃克里斯托夫·普夫卢姆埃米尔·侯赛因·帕勒姆雷米·马努克·安米安特雷莎·穆希卡-费尔瑙德克莱尔·德诺南古
Owner MERCK PATENT GMBH
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