Thermal-activation delayed fluorescence material based on 4-fluorophenylacetonitrile, and preparation and application thereof

A technology of delayed fluorescence and fluorobenzene acetonitrile, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve problems such as difficulty in achieving blue light emission

Active Publication Date: 2016-05-25
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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Method used

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  • Thermal-activation delayed fluorescence material based on 4-fluorophenylacetonitrile, and preparation and application thereof
  • Thermal-activation delayed fluorescence material based on 4-fluorophenylacetonitrile, and preparation and application thereof
  • Thermal-activation delayed fluorescence material based on 4-fluorophenylacetonitrile, and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] Add 703 mg of carbazole and 25 mL of N,N-dimethylformamide (DMF) into a three-neck flask with a stirring bar, gradually add 5 mL of DMF solution containing 150 mg of NaH at room temperature, stir for 30 minutes, and then add 193 mg of pentafluorobenzene Acetonitrile in DMF solution 5mL, stirred for 3h.

[0034] After the reaction, pour the reaction mixture into 50 mL of ice water, filter the precipitate, use silica gel as the stationary phase, and use a mixed solution of petroleum ether and dichloromethane with a volume ratio of 1 to 3:1 as the eluent, and separate it by column chromatography to obtain Compound CyFbCz yellow solid 327mg, yield 42%.

[0035] figure 1 In the H NMR spectrum, the chemical shifts at 7.84-7.59ppm, 7.49-7.28ppm, 7.15-6.99ppm, and 6.65-6.57ppm are aromatic hydrogens on the carbazole ring. Since the product is a symmetrical structure, the carbazole ring has a total of Four groups of hydrogens appeared, and the number of hydrogens i...

Embodiment 2

[0043]

[0044] Add 824 mg of phenoxazine and 30 mL of DMF into a three-necked flask with a stirring bar, gradually add 5 mL of DMF solution containing 170 mg of NaH at room temperature, stir for 40 min, then add 5 mL of DMF solution containing 193 mg of pentafluorophenylacetonitrile, and stir for 4.5 h.

[0045] After the reaction, pour the reaction mixture into 40 mL of ice water, filter the precipitate, use silica gel as the stationary phase, and use a mixed solution of petroleum ether and dichloromethane with a volume ratio of 1 to 4:1 as the eluent, and separate it by column chromatography to obtain Compound CyFbPOZ yellow solid 313mg, yield 37%.

[0046] 1 HNMR (500MHz, DMSO- d 6 )δ(ppm):7.33-7.29(m,8H),6.98(d, J =7.2Hz, 4H), 6.95-6.91(m, 4H), 6.75-6.70(m, 8H), 6.75-6.71(m, 8H).

[0047] The compound CyFbPOZ prepared in this example was doped in the mCP host material by vacuum evaporation to form a thin film, and the transient fluorescence decay curve at room temp...

Embodiment 3

[0050]

[0051] Add 856 mg of phenothiazine and 35 mL of DMF into a three-neck flask with a stirring bar, gradually add 7 mL of DMF solution containing 190 mg of NaH at room temperature, stir for 1 h, then add 5 mL of DMF solution containing 193 mg of pentafluorophenylacetonitrile, and stir for 7 h.

[0052] After the reaction, pour the reaction mixture into 60 mL of ice water, filter the precipitate, use silica gel as the stationary phase, and use a mixed solution of petroleum ether and methylene chloride with a volume ratio of 1 to 2:1 as the eluent. After separation by column chromatography, Obtained compound CyFbPTZ brown yellow solid 409mg, yield 45%.

[0053] 1 HNMR (500MHz, DMSO- d 6 )δ(ppm):7.69-7.63(m,8H),7.55-7.52(m,4H),7.50-7.46(m,4H),7.41(d, J =7.2Hz, 4H), 7.36-7.33(m, 4H), 7.29-7.25(m, 8H).

[0054] The compound CyFbPTZ prepared in this example is doped into the mCP host material to make a thin film, and the transient fluorescence decay curve at room temper...

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Abstract

The invention discloses a thermal-activation delayed fluorescence material with blue light emission wavelength. By using 4-fluorophenylacetonitrile as an electron acceptor unit, electron donors are connected to 2, 3, 5 and 6 sites of the central benzene ring to obtain the thermal-activation delayed fluorescence material. The thermal-activation delayed fluorescence material is the compound represented by the structural general formula (I), wherein R represents N-carbazolyl, N-phenothiazinyl or N-phenoxazinyl. Different electronegative functional groups are introduced into the 2, 3, 5 and 6 sites of the parent benzene ring of the 4-fluorophenylacetonitrile electron acceptor to perform chemical modification, thereby implementing blue light emission. The prepared fluorescent material has typical thermal-activation delayed fluorescence effects, can delay the fluorescence life by 10-60 microseconds, and is applicable to organic electroluminescent devices.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, and relates to a heat-activated delayed fluorescent material, a preparation method of the fluorescent material and its application in organic electroluminescent devices. technical background [0002] Organic electroluminescent devices are light in weight, fast in response, low in cost, and low in energy consumption, and have attracted widespread attention in the fields of flat-panel displays and solid-state lighting. According to quantum spin statistics, electrons and holes in organic electroluminescent devices are respectively injected from the two poles, migrate and recombine to generate 25% singlet excitons and 75% triplet excitons. [0003] Thermally Activated Delayed Fluorescence (TADF) materials can convert triplet excitons into singlet excitons through thermally excited antisystem crossing, thereby breaking through the theoretical limit of 25% of the exci...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D209/86C07D265/38C07D279/22H01L51/54
CPCC09K11/06C07D209/86C07D265/38C07D279/22C09K2211/1037C09K2211/1033C09K2211/1029H10K85/657H10K85/6572
Inventor 李洁侯文娟许慧侠张洁王华许并社
Owner TAIYUAN UNIV OF TECH
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