Compounds for electronic devices

A compound and atomic technology, applied in the field of compounds used in electronic devices, can solve problems such as high working voltage, blocking vapor deposition source, high working voltage, etc.

Active Publication Date: 2011-04-20
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 3. The operating voltage is quite high, especially in the case of fluorescent OLEDs, and should therefore be further reduced to improve power efficiency
However, this is almost impossible to achieve with state-of-the-art materials due to the concomitant voltage increase
[0007] 5. In state-of-the-art hole transport materials, there are often processability problems because these materials crystallize out at the edges of the vapor deposition source and thus block said vapor deposition source
However, it has been found that the latter leads to high operating voltages upon use in hole injection or hole transport layers, further implying that this type of material is often problematic as they block vapor deposition sources due to crystallization

Method used

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  • Compounds for electronic devices
  • Compounds for electronic devices
  • Compounds for electronic devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0149] Example 1: 4,6,6,10,12,12-hexamethyl-N,N,N',N'-tetraphenyl-6H,12H-indeno[1,2-b]fluorene-2 , 8-diamine

[0150] a) Diethyl 2,2″-dimethyl[1,1′; 4′,1″]terphenyl-2′,5′-dicarboxylate

[0151]

[0152] 60g (160mmol) of dibromodiethyl terephthalate, 43g (320mmol) of o-tolylboronic acid, 365mg (0.32mmol) of Pd (PPh 3 ) 4 and 92g (660mmol) of K 2 CO 3 Heated in 300ml of toluene and 300ml of water for 4h under boiling. The mixture was then partitioned between toluene and water, and the organic phase was washed three times with water and washed with Na 2 SO 4 dry. The remaining residue was recrystallized twice from heptane to yield colorless crystals. Yield is 51 g (127 mmol, 81%).

[0153] b) 2-[5′-(1-hydroxyl-1-methylethyl)-2,2″-dimethyl[1,1′; 4′,1″]terphenyl-2′-yl]propane -2-ol

[0154]

[0155] 39 g (97 mmol) of the diester were initially introduced into 500 ml of dry THF, 195 ml (580 mmol) of a 3 M solution of methylmagnesium chloride in THF were added to the...

Embodiment 2

[0165] Example 2: 5,6,11,11,12,12-hexamethyl-N,N,N',N'-tetraphenyl-11H,12H-indeno[2,1-a]fluorene-2 , 9-diamine

[0166] a) 1,4-dibromo-2,3-xylene

[0167]

[0168] The compound was prepared according to Cachia, Wahl, Bull. Soc. Chim. Fr. 1958, 1418-1420.

[0169] b) 2,3-xylene-1,4-bisboronic acid pinacyl ester

[0170]

[0171] 100g (380mmol) of 1,4-dibromo-2,3-xylene was dissolved in 1500ml of dry ether, and 420ml (840mmol) of 2M n-butyllithium in cyclohexane was added dropwise at -70°C, After 1 h, 130 ml of trimethyl borate (1140 mmol) were added dropwise, the mixture was brought to RT during 1 h, the solvent was removed, 90 g (76 mmol) of pinacol and 1000 ml of toluene were added, and the mixture was heated at boiling for 2 h , the solvent is removed again, and the 1 H-NMR showed a homogeneous residue which was used in the subsequent reaction without further purification.

[0172] c) 2′,3′-dimethyl[1,1′;4′,1″]terphenyl-2,2″-dicarboxylic acid dimethyl ester

[01...

Embodiment 3

[0187] Example 3: 4,7,11,11,12,12-hexamethyl-N,N,N',N'-tetraphenyl-11H,12H-indeno[2,1-a]fluorene-2 , 9-diamine

[0188]

[0189] a) o-methylcinnamaldehyde

[0190]

[0191] This compound was synthesized according to Battistuzzi et al., Organic Letters 2003, 5(5), 777-780.

[0192] b) Diethyl 2-methylbenzylphosphonate

[0193]

[0194] The compound was synthesized according to de Meijere et al., Eur. J. Org. Chem. 1998, 2289-2299.

[0195] c) 2,2'-Dimethyltransstilbene

[0196]

[0197] The compound was synthesized according to de Meijere et al., Eur. J. Org. Chem. 1998, 2289-2299.

[0198] 5.99 g (149.9 mmol, 60% suspension in paraffin oil) of NaH were suspended in 250 ml of THF under argon atmosphere. The mixture was cooled to 0° C. and 37.28 g (153.9 mmol) of diethyl 2-methylbenzylphosphonate in 20 ml THF were added during 15 min. 19.74 g (135.0 mmol) o-cinnamaldehyde dissolved in 20 ml of THF were then added. The reaction was then stirred at RT for severa...

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Abstract

The invention relates to the improvement of organic electroluminescent devices, in which compounds that are represented by formula (1) are used, in particular as hole injection materials or hole transport materials in a hole injection layer or hole transport layer.

Description

technical field [0001] The present invention describes novel compounds and their use in electronic devices. 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, these devices still have considerable issues that require urgent improvement: [0003] 1. The efficiency is still low, especially in the case of fluorescent OLEDs, and should be improved. [0004] 2. There is still a need to improve the operating lifetime, especially in the case of blue light emission. [0005] 3. The operating voltage is rather high, especially in the case of fluorescent OLEDs, and should therefore be further reduced to improve power efficiency. This is especially crucial for mobile applications. Further improvements are desired in this regard, especially in the case of charge transport materials. [0006] 4. In the case of the hole-transport materials of the prior art...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C09K11/06
CPCC09K2211/1096C09K11/06H01L51/006C09K2211/1029C09K2211/1044C09K2211/1088H01L51/5048H05B33/22C09K2211/1092H01L51/5088H01L51/5016Y02E10/549C07C2103/52C07C211/61C07C2603/52H10K85/633H10K50/14H10K50/17H10K50/11H10K2101/10C07D487/04C07D241/36
Inventor 克里斯托夫·普夫卢姆阿尔内·比辛埃米尔·侯赛因·帕勒姆罗科·福特霍尔格·海尔菲利普·施特塞尔
Owner MERCK PATENT GMBH
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