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Fluorenes and electronic devices containing them

A technology of atoms and groups, applied in the field of new organic compounds, can solve problems such as poor performance data and high working voltage

Inactive Publication Date: 2015-05-06
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In practice, hole transport layers are usually required to have larger layer thicknesses, but this often results in higher operating voltages and poorer performance data

Method used

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  • Fluorenes and electronic devices containing them
  • Fluorenes and electronic devices containing them
  • Fluorenes and electronic devices containing them

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0278] Synthesis of compound biphenyl-4-yl-(9,9-diphenyl-9H-fluoren-4-yl)amine (1-1) and compound (1-2) to (1-12)

[0279]

[0280] 4-bromo-9,9-diphenyl-9H-fluorene

[0281] 37 g (152 mmol) of 2,2'-dibromobiphenyl was dissolved in 300 ml of dry THF in a flask that had been dried by heating. The reaction mixture was cooled to -78°C. At this temperature, 75 ml of a 15% solution of n-BuLi (119 mmol) in hexane was slowly added dropwise (duration: about 1 hour). The batch was stirred for another hour at -70°C. Subsequently 21.8 g of benzophenone (119 mmol) was dissolved in 100 ml of THF and added dropwise at -70°C. When the addition is complete, slowly warm the reaction mixture to room temperature and use NH 4 Cl is quenched and then evaporated in a rotary evaporator. 510 ml of acetic acid was carefully added to the evaporated solution, and then 100 ml of fuming hydrochloric acid was added. The batch was heated to 75°C and held at this temperature for 4 hours. During this time a w...

Embodiment 2

[0293] Compound biphenyl-3-ylbiphenyl-4-yl-(9,9-dimethyl-9H-fluoren-3-yl)amine (2-1) and compounds (2-2) to (2-10) Synthesis

[0294]

[0295] 3-bromo-9,9-dimethyl-9H-fluorene

[0296] 29.5 g (120 mmol) of 3-bromo-9H-fluorene (Tetrahedron Letters, 51, 37, 4894-4897; 2010) was dissolved in 220 ml of dry DMSO in a flask that had been dried by heating. Add 34.7g (361mmol) NaO at room temperature t Bu. The suspension was brought to an internal temperature of 65°C. At this temperature, a solution of 22.5 ml (361 mmol) of methyl iodide in DMSO (50 ml) was added dropwise at a rate such that the internal temperature did not exceed 65° C. (duration: about 30 minutes). Keep the batch at an internal temperature of 65°C for another 30 minutes, then pour 400ml of ice-cold NH 4 OH aqueous solution (1 / 1, v / v) and stir for about 20 minutes. Suction to filter out the precipitated solid and use about 200ml H 2 O and methanol are washed sequentially. Yield: 31 g (114 mmol) (95% of theory).

[029...

Embodiment 3

[0305] Compound biphenyl-2-ylbiphenyl-4-yl-(9,9-diphenyl-9H-fluoren-3-yl)amine (3-1) and compounds (3-2) to (3-5) Synthesis

[0306]

[0307] 3-bromo-9,9-diphenyl-9H-fluorene

[0308] 50 g (193 mmol) of 3-bromo-9H-fluorenone (Tetrahedron (tetrahedron), 51, 7, 2039-54; 1995) was dissolved in 500 ml of dry THF in a flask dried by heating. The clear solution was cooled to -10°C and then 70.7 ml (212 mmol) of 3M phenyl magnesium bromide solution was added. The reaction mixture was slowly warmed to room temperature, and then NH 4 Cl (500ml) quenched. The mixture was then partitioned between ethyl acetate and water, and the organic phase was washed three times with water, 2 SO 4 Dry and evaporate in a rotary evaporator. The crude product was recrystallized from heptane / toluene. 400 ml of benzene was added to the residue. The batch was heated to 50°C, and then 18.6 ml of trifluoromethanesulfonic acid was added dropwise. After 30 minutes, the reaction mixture was cooled to room tempe...

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Abstract

The present invention concerns particular fluorenes, the use of the compound in an electronic device, and an electronic device containing at least one of these compounds. The present invention further concerns a method for producing the compound and a formulation and composition containing one or more of the compounds.

Description

Technical field [0001] The present invention relates to a novel organic compound, to the use of the compound in an electronic device, and to an electronic device containing at least one of the compounds. The present invention also relates to methods for preparing the compounds and to compositions and formulations containing at least one of the compounds. Background technique [0002] The development of functional compounds for use in electronic devices is currently the subject of intense research. The purpose here is in particular to develop compounds with which the performance of electroluminescent devices can be improved at one or more relevant points, such as the power efficiency, lifetime or color coordinates of the emitted light. [0003] According to the present invention, the term electronic device is considered to refer especially to organic integrated circuits (OIC), organic field effect transistors (OFET), organic thin film transistors (OTFT), organic light emitting tran...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/02C07D333/50C07C211/61C07D239/26C07C217/92C07D265/38C07D279/36C07F7/08C07D213/38C07D307/77C09K11/06H01L51/50H10K99/00
CPCC07C209/10C07C213/06C07D209/02C07D209/86C07D307/91C07D311/86C07D333/76C09K11/06C07C2603/18C09K2211/1014C09K2211/1029C09K2211/1092C09K2211/1088H10K85/633H10K85/6576H10K85/6574H10K85/6572H10K50/17H10K50/18H10K50/181H10K50/171C07C211/61C07C215/88C07D219/02C07C211/54C07C217/80C07C217/92C07F5/025C07D311/80C07D405/04C07D407/04C07D407/12H05B33/10C09K2211/1007C09K2211/1011C09K2211/1096Y02E10/549C07C2603/97C07D209/90H10K85/615H10K85/631H10K50/15C07C13/567C07D333/50H10K50/11H10K85/626C07C209/60
Inventor 特雷莎·穆希卡-费尔瑙德埃尔维拉·蒙特内格罗埃米尔·侯赛因·帕勒姆阿尔内·比辛弗兰克·福格斯
Owner MERCK PATENT GMBH
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