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Phenanthrene compounds for organic electronic devices

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

Active Publication Date: 2015-02-18
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In practice, a greater thickness of the hole transport layer is often desired, but this usually results in higher operating voltages and poorer performance data

Method used

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  • Phenanthrene compounds for organic electronic devices
  • Phenanthrene compounds for organic electronic devices
  • Phenanthrene compounds for organic electronic devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0205] Synthesis of biphenyl-4-yl-(9,9-dimethyl-9H-fluoren-2-yl)phenanthrene-3-ylamine (1-1)

[0206]

[0207] Synthesis of raw material 3-bromophenanthrene

[0208]

[0209] Synthesis of 3-Aminophenanthrene

[0210] 50 g (227 mmol) of 3-acetylphenanthrene and 63.8 ml (790 mmol) of pyridine and 42 g (592 mmol) of hydroxyammonium chloride were dissolved in 300 mL of EtOH. The batch was heated to 75°C. After 1 hour of reaction the batch was cooled. The mixture was then partitioned between ethyl acetate and water, the organic phase was washed three times with water and washed with Na 2 SO 4 Dry and concentrate on a rotary evaporator. 300 ml of polyphosphoric acid was carefully added to the concentrated solution, and the mixture was heated at 75°C for 1 hour. The batch was then cooled to room temperature and poured carefully into ice water (300ml). The precipitated solid was filtered off with suction and rinsed with methanol. Finally, 800ml MeOH and 70ml concentrated...

Embodiment 13

[0226] Compound N*4'*-biphenyl-4-yl-N*4'*-dibenzofuran-4-yl-N*4*-phenanthrene-3-yl-N*4*-phenylbiphenyl- Synthesis of 4,4'-diamine (2-1)

[0227]

[0228] Dissolve 10g phenanthrene-3-ylphenylamine (37mmol), 21g biphenyl-4-yl-(4'-bromobiphenyl-4-yl)dibenzofuran-4-ylamine (37mol) in 500ml toluene Middle: degas the solution and wash with N 2 saturation. Then 1.5 ml (1.5 mmol) of tri-tert-butylphosphine solution and 0.17 g (0.74 mmol) of palladium(II) acetate were added, and thereafter 5.6 g of sodium tert-butoxide (56 mmol) were added. The reaction mixture was heated at boiling for 3 hours under a protective atmosphere. Thereafter the mixture was partitioned between toluene and water, the organic phase was washed three times with water and washed with Na 2 SO 4 Dry and evaporate on a rotary evaporator. After filtration of the crude product through silica gel with toluene, the remaining residue was recrystallized from heptane / toluene and finally sublimed under high vacuum,...

Embodiment 19

[0237] Synthesis of Compound Biphenyl-4-ylbiphenyl-2-yl-(9,9-Dimethyl-7-phenanthrene-3-yl-9H-fluoren-2-yl)amine (3-1)

[0238]

[0239] 3-(7-Bromo-9,9-dimethyl-9H-fluoren-2-yl)phenanthrene

[0240] Mix 52g (164mmol) of 7-bromo(9,9-dimethylfluoren-2-yl)boronic acid (CAS number: 1213768-48-9), 50g (164mmol) of 3-iodophenanthrene and 205ml of 2M NaHCO 3 The aqueous solution (327 mmol) was suspended in 800 ml of dimethoxyethane. 3.8 g (3.3 mmol) tetrakis(triphenyl)phosphine palladium(0) were added to the suspension, and the reaction mixture was heated under reflux for 16 hours. After cooling, the organic phase was separated, filtered through silica gel, washed 3 times with 300 mL of water and then evaporated to dryness. The crude product was filtered through silica gel with heptane / ethyl acetate (20:1) to afford 55 g (75%) of 3-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)phenanthrene .

[0241] Biphenyl-4-ylbiphenyl-2-yl-(9,9-dimethyl-7-phenanthrene-3-yl-9H-fluoren-2-yl)amine

...

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Abstract

The invention relates to specific phenanthrenes, the use of the compound in an electronic device, and an electronic device containing at least one of said compounds. The invention further relates to 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 said compound in an electronic device, and to an electronic device comprising at least one of said compound. The invention also relates to processes for the preparation of said compounds and to compositions and formulations comprising at least one of said compounds. Background technique [0002] The development of functional compounds for use in electronic devices is currently the subject of intense research. The aim here is in particular to develop compounds with which improvements in the properties of electronic devices can be achieved in one or more relevant points, such as performance efficiency, lifetime or color coordinates of luminescence. [0003] According to the present invention, the term electronic device is in particular taken to mean organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic light-emi...

Claims

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Application Information

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IPC IPC(8): C07D311/82C07D219/02C07D221/18C07D223/26C07D333/76C07C211/61C07D407/04C07C217/92C07D265/38C07D279/36C07F7/08C07D213/38C07D307/91C09K11/06H01L51/00
CPCC07C2103/54C09K2211/1011H01L51/5012C07D279/22C07D213/16C07D219/02C07C2103/52H01L51/5096C07C211/61C09K2211/1007C07C217/80C09K11/06C07C2103/94H01L51/0073C07D223/26C07D209/94C07C2101/14C09K2211/1014C07D471/06C07D311/80H01L51/0072C07D209/86C09K2211/1092C07C2103/26C09K2211/1029H01L51/006H01L51/0061C07D307/93C07D405/12C07D405/04C07D407/12C07D213/06C07D307/91C07D265/38C07D333/76H01L51/0074C09K2211/1088C07D487/04C07C2103/18Y02E10/549C07D221/08C07F7/0803C07F7/0816C07C217/92C07D209/88C07D213/38C07D219/08C07D223/14C07D279/28C07D311/82C07F7/081C07C2603/54C07C2603/52C07C2603/94C07C2601/14C07C2603/26C07C2603/18C09K2211/1096C09K2211/1037C09K2211/1033C09K2211/104C09K2211/1022H10K85/624H10K85/626H10K85/636H10K85/633H10K85/615H10K85/631H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K85/40H10K50/11H10K50/181H10K50/17C09B19/00C09B21/00C09B57/008C09B69/008C07C2603/97C07C211/54H10K50/00H10K50/15H10K50/18C07C209/60
Inventor 特雷莎·穆希卡-费尔瑙德阿尔内·比辛弗兰克·福格斯乔纳斯·瓦伦丁·克罗巴
Owner MERCK PATENT GMBH
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