Compounds for electronic devices

A compound and atomic technology, applied in the field of electronic devices, can solve problems such as high technical complexity, industrial process complexity, thermal instability, etc.

Active Publication Date: 2012-10-10
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The indenofluorenamines described above suffer from processability disadvantages: during the vapor deposition or coating process, premature deposition occurs, thus complicating the industrial process
However, these compounds are thermally unstable and cannot be evaporated without decomposition, which requires high technical complexity for OLED production and thus represents a technical disadvantage

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 to 30

[0306] A) Synthesis of the compounds of the present invention from Examples 1 to 30

[0307] Unless otherwise noted, the following syntheses were carried out under a protective gas atmosphere. This starting material can be purchased from ALDRICH or ABCR (palladium(II) acetate, tri-o-tolylphosphine, inorganics, solvents). According to the literature, 8,8-dimethylindolo[3,2,1-de]acridine and 7,7,11,11-tetramethyl-7H,11H-benzo[1,8]indole can be synthesized Indo[2,3,4,5,6-de]acridine (Chemische Berichte 1980, 113(1), 358-84). 8H-indolo[3,2,1-de]phenazine (Journal of the Chemical Society 1958, 4492-4) and B-[4-(1-phenyl-1H-benzimidazol-2-yl) phenyl]boronic acid (Advanced Functional Materials 2008, 18(4), 584-590), 2-bromoindolo[3,2,1-jk]carbazole and indolo[3,2,1-jk] Carbazoleboronic acid (Chemistry A European Journal, 2009, 15(22), 5482-5490), N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-9H-fluorene-2 -amine (WO 2006073054) and 7-bromo-2,12-dimethyl-10-phenyl-10,12-dihydro-10-azaideno[...

Embodiment 1

[0308] Example 1: 3-bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine

[0309]

[0310] Methyl 2-(3-bromo-9H-carbazole)benzoate:

[0311]In 2000ml of DMF, 62g (207mmol) of methyl 2-(9H-carbazole)benzoate was cooled to -10°C, 37.3g (207mmol) of NBS was added in portions, and the mixture was stirred at room temperature for 6h. Subsequently, 500 ml of water was added to the mixture, followed by CH 2 Cl 2 extract. The organic phase was dried using magnesium sulfate and the solvent was removed under vacuum. The product is washed with hot toluene by stirring and filtered with suction.

[0312] Yield: 72 g (190 mmol), 92% of theory, according to 1 The purity by H-NMR is about 98%.

[0313] 2-[2-(3-Bromocarbazol-9-yl)phenyl]propan-2-ol:

[0314] 81 g (213 mmol) of methyl 2-(3-bromo-9H-carbazole)benzoate were dissolved in 1500 ml of dry tetrahydrofuran and degassed. The mixture was cooled to -78°C and 569 ml (854 mmol) of methyllithium were added over a period of 40 minutes. T...

Embodiment 2

[0318] Example 2: 6-bromo-8,8-dimethyl-3-phenyl-8H-indolo[3,2,1-de]acridine

[0319]

[0320] Methyl 2-(3-phenyl-9H-carbazole)benzoate:

[0321] 85g (350mmol) 3-phenyl-9H-carbazole, 63ml (262mmol) methyl 2-iodobenzoate, 87g (631mmol) potassium carbonate and 9.3g (35mmol) 18-crown-6 were first under protective gas Introduce into 1200ml of DMF and heat at 130°C for 86h. The mixture was then evaporated, washed with hot heptane by stirring, chromatographed (heptane / CH 2 Cl 2 1:1) for purification. The product was washed with hot hexane with stirring and filtered with suction.

[0322] Yield: 82 g (219 mmol), 62% of theory, according to 1 The purity by H-NMR is about 97%.

[0323] Methyl 2-(3-bromo-6-phenyl-9H-carbazole)benzoate:

[0324] Cool 78.4g (207mmol) of methyl 2-(3-phenyl-9H-carbazole)benzoate in 2000ml of DMF to -10°C, add 37.3g (207mmol) of NBS in portions, and stir the mixture at room temperature 6h. Subsequently, 500 ml of water was added to the mixture, fo...

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Abstract

The present invention relates to compounds according to formula (I), to the use thereof in organic electronic devices, and to organic electronic devices that contain compounds according to formula (I), preferably as hole transport materials and/or as matrix materials, in particular in combination with a further matrix material.

Description

technical field [0001] The present invention relates to compounds of general formula (I), and their use in electronic devices, and electronic devices comprising these compounds. Background technique [0002] Organic semiconducting materials, such as the compounds of the present invention, are being developed for many different electronic device applications. [0003] Structures of organic electroluminescent devices (OLEDs) in which the compounds according to the invention can be used as functional materials are described, for example, in US 4539507, US 5151629, EP 0676461 and WO 98 / 27136. [0004] Regarding the performance data of organic electroluminescent devices, there is still a need for further improvement, especially for broad commercial use. Of particular importance in this connection are the lifetime, efficiency and operating voltage of the organic electroluminescent device, and the achieved color value. Especially in the case of blue-emitting electroluminescent de...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D265/34C07D413/14C07D401/14C07D403/14H01L51/00
CPCC09B57/008H01L51/0072C07D413/14H01L51/0061H01L51/006C07D403/14C07D265/34C09B17/00C07D401/14C09B57/00C09B15/00C09B21/00C07D209/86H01L2251/5384H01L51/0058Y02E10/549C07D471/06C07D498/06C07D519/00H10K85/657H10K85/6572C09K11/06H10K85/636H10K85/626H10K85/633H10K50/15H10K2101/90C09K2211/1029C09K2211/1011C09K2211/1007H10K10/00H10K30/00H10K50/17
Inventor 埃米尔·侯赛因·帕勒姆克里斯托夫·普夫卢姆康斯坦策·布罗克
Owner MERCK PATENT GMBH
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