Materials for organic electroluminescent devices

A technology of general formula and compound, applied in the field of preparing the compound of the present invention, can solve the problems of short working life, vapor deposition, low electron mobility and the like

Active Publication Date: 2012-05-09
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 2. Usually the working life is still relatively short, especially in the case of blue light emission, so further improvement is needed here
Since then AlQ 3 Often used as an electron transport material, but it has a number of disadvantages: it cannot be vapor-deposited without residues, since it partially decomposes at sublimation temperatures, which represents a major problem especially for production plants
This has the consequence that the vapor deposition source must be cleaned or replaced frequently
In addition, AlQ 3 decomposition products enter the OLED, where they cause shortened lifetime and reduced quantum and power efficiencies
In addition, AlQ 3 Has low electron mobility, which results in high voltage and therefore lower power efficiency
To avoid short circuits in displays, it is desirable to increase the thickness of the layer; for AlQ 3 This is not possible due to the low charge carrier mobility and the resulting voltage increase
The charge-carrier mobility of other electronic conductors (US4,539,507) is also too low to form thick layers with them, and as a result OLED lifetimes are even longer than those using AlQ 3 worse
QUR 3 Intrinsic color (yellow in solid state) due to reabsorption and weak re-emission can lead to a color shift, especially in the case of blue OLEDs, which likewise proves to be disadvantageous

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

[0229] Example 1: Synthesis of 2,5-bis(9-phenyl-9H-carbazol-3-yl) diethyl terephthalate:

[0230]

[0231] 913mg (3mmol) of tris(o-tolyl)phosphine, and then 112mg (0.5mmol) of palladium(II) acetate were added to 18.6g (49.1mmol) of 2,5-dibromoterephthalate diethyl and 38g which were well stirred (102mmol) (9-phenyl-9H-carbazol-3-yl) boric acid and 51g (221mmol) tripotassium phosphate in 380ml toluene, 190ml two In a suspension of a mixture of alkane and 480 ml of water, the mixture was heated to reflux for 16 h. After cooling to room temperature (RT), 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, V: V), and three times with 100 ml of ethanol, and removed from DMF (About 10ml / g) Recrystallize three times.

[0232] Yield: 22.6 g (32 mmol), 63.0%.

Embodiment 2

[0233] Example 2: Synthesis of 2-[4-(1-hydroxy-1-methylethyl)-2,5-bis(9-phenyl-9H-carbazol-3-yl)phenyl]propan-2- alcohol:

[0234]

[0235] Dissolve 6.8g (9.67mmol) 2,5-bis(9-phenyl-9H-carbazol-3-yl)diethyl terephthalate in 40ml THF, add 40ml (42mmol) at -75℃ A 2M methyl lithium solution in diethyl ether, the mixture was stirred at -75°C for 3 h. After warming to room temperature, use NH 4 The mixture was hydrolyzed with Cl solution, extracted with ethyl acetate, dried, and the solvent was removed under reduced pressure. The remaining colorless solid was recrystallized twice from toluene / EtOH, leaving 4.2 g (6.2 mmol) of 62% diol in the form of colorless crystals.

Embodiment 3

[0237]

[0238] 3.38g (5mmol) 2-[4-(1-hydroxy-1-methylethyl)-2,5-bis(9-phenyl-9H-carbazol-3-yl)phenyl]propan-2 -The alcohol is dissolved in 30 ml of dichloromethane and cooled to 5°C, and a mixture of 4 g of polyphosphoric acid in 3 ml of methanesulfonic acid is added. After keeping at 5°C for 30 minutes, 50 ml of EtOH was added and the mixture was heated at boiling for 1 h. The colorless precipitate was filtered off, washed twice with EtOH and heptane, and recrystallized from chlorobenzene once to obtain a colorless solid product (2 g, 4 mmol) with a yield of 75% and a purity of >99.9% according to RP-HPLC.

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Abstract

The present invention describes indenocarbazole derivatives having electron and hole transport properties, especially for use in the emission layer and/or charge transport layer of electroluminescent devices or as matrix material. The invention further provides a process for preparing the compounds of the invention, and electronic devices comprising them.

Description

Technical field [0001] The present invention describes indenocarbazole derivatives with electron and hole transport properties, especially used in the light-emitting and / or charge transport layer of electroluminescent devices or as host materials. The present invention also relates to a method of preparing the compound of the present invention and an electronic device including the compound. Background technique [0002] The general structure of organic electroluminescent devices is described, for example, in US 4539507, US5151629, EP 0676461 and WO 98 / 27136. However, these devices still need improvement: [0003] 1. The efficiency in the case of fluorescent and phosphorescent OLEDs should be improved. [0004] 2. Usually the working life is still relatively short, especially in the case of blue light, so further improvement is needed here. [0005] 3. The operating voltage in the case of fluorescent and phosphorescent OLEDs should be reduced, which leads to an improvement in power ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/78C07D333/52C07D403/04C07D403/10C07D403/14C07D407/10C07D409/10C07D413/04C07D413/10C07D417/10C07D471/04C07D487/04C07D498/04C07D513/04C07F9/6506
CPCH05B33/10C09K2211/1011C07D209/82C07D471/04C07D407/10C07D307/78H01L51/5048C07D403/14H01L51/5096C09K2211/1033C07D403/04C09B57/00C07D413/04C07F9/65848C09K2211/1007C09K11/06C07D403/10C07F9/65685H01L2251/5384C09K2211/1014H01L2251/308C09K2211/1044H01L51/001C07D409/10H01L51/5016H05B33/00H01L51/0072H01L51/0067C09K2211/1029C09K2211/1092C07D513/04C07D498/04C09K2211/1037C07F15/0086C09B17/00C07F15/0033C07D413/10C09B15/00C07F9/65683C09K2211/1059C09K2211/1088C07D487/04C07D333/52C07D417/10H01L51/00Y02E10/549C09B19/00C07D209/70C07D401/14C07D493/04C09K11/025H10K71/164H10K85/654H10K85/6572H10K50/11H10K2101/10H10K50/14H10K50/18H10K2102/103H10K2101/90C07D265/38C07D241/36H10K85/633H10K50/15H10K50/16H10K85/636H10K85/657
Inventor 克里斯托夫·普夫卢姆阿尔内·比辛埃米尔·侯赛因·帕勒姆特雷莎·穆希卡-费尔瑙德霍尔格·海尔菲利普·施特塞尔
Owner MERCK PATENT GMBH
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