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Non-conjugated derivative material with fluorine-triphenylamine structure and synthesis method thereof

A synthesis method and technology of triphenylamine, which are applied in the field of synthesis of non-conjugated derivative materials, can solve the problems affecting the saturated color purity, efficiency and stability of devices, difficulty in injection of holes and electrons, mismatch of cathode work functions, etc. Achieve the effects of improving thermal stability and film-forming properties, cheap raw materials, and improving injection and transport capabilities

Inactive Publication Date: 2010-06-23
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the rigid planar biphenyl structure of fluorene makes it easy for the material to form intermolecular excimer associations (Surin M, Hennebicq E et al. Chem. Mater, 2004, 16 (6): 994-1001) or fluorenone ( List E J W, Guentner R.Adv Mater, 2002, 14 (5): 374-378) thus produces long-wave emission, which seriously affects the saturation color purity, efficiency and stability of the luminescence of the device
At the same time, the energy level of the conjugated derivatives of fluorene does not match the work function of the anode and cathode of the device, thus causing difficulties and imbalances in the injection of holes and electrons, and the formation of aggregation states and / or easy formation due to poor thermal stability. excimer

Method used

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  • Non-conjugated derivative material with fluorine-triphenylamine structure and synthesis method thereof
  • Non-conjugated derivative material with fluorine-triphenylamine structure and synthesis method thereof
  • Non-conjugated derivative material with fluorine-triphenylamine structure and synthesis method thereof

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Experimental program
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Effect test

Embodiment 1

[0033]

[0034] Step 1: Synthesis of Compound 9-p-tolyl-9H-fluoren-9-ol, PTF

[0035] p-Bromotoluene (40mmol, 6.8g) was dissolved in 15ml of anhydrous ether, magnesium powder (40mmol, 0.96g) and a little iodine to react to generate Grignard reagent, which was placed in an ice bath, and fluorenone (20mmol 3.6g) Dissolved in 20ml of anhydrous ether solution, added dropwise to Grignard reagent to react for 3h. Add saturated ammonium chloride solution dropwise to quench the reaction, add chloroform to extract, then use petroleum ether / ethyl acetate=20 / 1 as the eluent silica gel chromatography to obtain the crude product, and then pass through diethyl ether / n-hexane (5 / 1) Recrystallization obtained 4.3 g of the target product PTF with relatively high purity, and the yield was 79%.

[0036] 1 H NMR (CDCl 3500MHz) δ7.64(d, J=7.5Hz 2H), 7.31-7.29(m, 4H), 7.06-7.26(m, 4H), 7.05(d, J=8Hz 2H), 2.48(s, 1H), 2.28(s, 3H)

[0037] 12 C NMR (CDCl 3 500MHz) δ150.6, 140.3, 139.6, 136...

Embodiment 2

[0043]

[0044] Step 1: Synthesis of 9-(4-fluorophenyl)-9H-fluoren-9-ol, FPF

[0045] According to the operation of step 1 in Example 1, p-bromofluorobenzene (40mmol, 7g), magnesium powder (4mmol, 0.96g), and fluorenone (10mmol, 1.8g) gave the product FPF (2.42g, 87.6%).

[0046] 1 H NMR (CDCl 3 500MHz) δ7.83-7.82(m, 2H), 7.39-7.35(m, 2H), 7.29-7.25(m, 6H), 7.08-7.04(m, 2H), 6.40(s, 1H)

[0047] 12 C NMR (CDCl 3 500MHz) δ162.1, 160.1, 151.1, 141.3, 141.2, 139.1, 128.6, 128.1127.1, 124.6, 120.1, 114.8, 114.6, 82.2

[0048] Step 2: Compound 4-methyl-N, N-bis(4-(9-(4-fluor-ophenyl)-9H-fluoren-9-yl)-phenyl-)aniline, synthesized by MFFPA

[0049] According to the operation of step 2 in Example 1, 4-methyltriphenylamine (1 mmol, 0.26 g) and FPF (2.2 mmol, 0.61 g) were reacted for 3 h to obtain the target product MFFPA (0.72 g, 92.9%).

[0050] 1 H NMR (CDCl 3 500MHz) δ7.73(d, J=8.0, 4H), 7.36-7.32(m, 8H), 7.26-7.23(m, 4H), 7.15(dd, J=8.5, 4H), 7.02-6.93(m, 8H), 6.89-6...

Embodiment 3

[0053]

[0054] Step 1: Synthesis of Compound 9-(4-tert-butylphenyl)-9H-fluoren-9-ol, TBPF)

[0055] According to the operation of step 1 in Example 1, p-tert-butylbromobenzene (20mmol, 4.3g), magnesium powder (20mmol, 0.48g), fluorenone (10mmol, 1.8g) obtained product TBPF (2.91g, 92.7%) .

[0056] 1 H NMR (CDCl 3 500MHz ppm) δ7.63(dd, J=7.0, 2H), 7.34-7.31(m, 4H), 7.29-7.24(m, 4H), 7.23-7.20(m, 4H), 2.45(s, 1H), 1.26(s, 9H).

[0057] 12 C NMR (CDCl 3 500MHz ppm) δ150.4, 149.3, 140.1, 139.5, 128.9, 128.3, 125.1, 125.0, 124.8, 120.0, 83.5, 34.4, 31.3.

[0058] Step 2: Synthesis of compound 4-methyl-N, N-bis(4-(9-(4-tert-butylphenyl)-9H-fluoren-9-yl)phenyl)aniline, MTFPA

[0059] 4-Methyltriphenylamine (1mmol, 0.26g), TBPF (2.2mmol 0.69g) were dissolved in 80ml of dichloromethane, and then 20ml of dichloromethane dissolved with trifluoromethanesulfonic acid (5.5mol 0.82g) was slowly Added, reacted at room temperature for 1 h, washed three times with saturated sodiu...

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Abstract

The invention discloses a non-conjugated derivative material with a fluorine-triphenylamine structure and a synthesis method thereof; the non-conjugated derivative material with the fluorine-triphenylamine structure has the structure shown by the formula (I), in the formula (I), at least two of R1, R2 and R3 are chosen from the groups shown by a formula (II) independently, when only two groups of the R1, R2 and R3 are chosen from the groups shown by the formula (II) independently, the remaining groups are chosen from methyl, bromine, fluorine, nitrile group or methoxy group; in the formula (II), R4 and R5 are chosen from one of the following independently: H, Br or I; Ar is aryl group. The synthesis method of the non-conjugated derivative material with the fluorine-triphenylamine structure has the advantages that the energy level can be adjusted independently, the method is well matched with the work function of anode material, and the method has high heat and light stability and good molding performance.

Description

(1) Technical field [0001] The invention belongs to the technical field of organic information functional materials, and specifically relates to a synthesis method of a non-conjugated derivative material with a fluorene-triphenylamine structure. (2) Background technology [0002] Organic electroluminescent technology has shown great commercial prospects in the fields of communication, information, display and lighting, and has been one of the research hotspots in the field of optoelectronic information in recent years. Displays made of organic electroluminescent devices have the advantages of high image quality, adjustable screen size, low energy consumption, light weight and thinness, foldable flexible polymer substrates, and low processing costs, which represent the development trend of display technology. [0003] For luminescent materials, green light is relatively mature, while blue and red light materials still need to be improved. Fluorene has high thermal stability,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/56C07C211/54C07C209/68C09K11/06
Inventor 张诚项文勤张玉建胡斌欧阳密俞春辉余振伟马淳安
Owner ZHEJIANG UNIV OF TECH
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