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Pyrrolepyrrolidine-diones-fluorene copolymer electroluminescent material and its preparation method

A technology of pyrrolopyrrole dilidone and pyrrolopyrrole dilidone, which is applied in the field of pyrrolopyrrole dilidone-fluorene copolymer electroluminescent materials and its preparation, can solve fluorescence quenching, intensify molecular aggregation, and luminescence Low efficiency and other issues, to achieve the effect of broad absorption

Inactive Publication Date: 2007-08-01
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The main reasons are: (1) The frequency difference between red light (700nm) and green light (510nm) and blue light (470nm) is relatively large, corresponding to the transition with a small energy gap of the polymer, which requires a special design of the molecular structure; ( 2) Although the commonly used doping technology can effectively adjust the luminescent color, it will inevitably produce impure luminescence (when the doping concentration is low) and low luminous efficiency (when the doping concentration is high), and it is necessary to strictly control the doping concentration, it is difficult to achieve mass production; (3) there are strong π-π interactions or strong charge transfer (Charge Transfer, CT) characteristics in the red light material system, which will aggravate molecular aggregation and lead to fluorescence quenching

Method used

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  • Pyrrolepyrrolidine-diones-fluorene copolymer electroluminescent material and its preparation method
  • Pyrrolepyrrolidine-diones-fluorene copolymer electroluminescent material and its preparation method
  • Pyrrolepyrrolidine-diones-fluorene copolymer electroluminescent material and its preparation method

Examples

Experimental program
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Embodiment 1

[0025] (1) Synthesis of 3,6-bis(4-bromophenyl)pyrrolo[3,4c]pyrrole-1,4-dione (DPP1):

[0026] 4.6 g of metallic sodium (0.2 mol) and a catalytic amount of FeCl 3 Add 100ml of tert-amyl alcohol, keep the temperature at 90°C, stir and reflux for about 1h, until the sodium metal is completely dissolved. After cooling to about 50°C, 18.2 g of 4-bromobenzonitrile (0.1 mol) was added, and the temperature was raised to 90°C again. 8.08 g of diisopropyl succinate (0.04 mol) was dissolved in about 30 ml of tert-amyl alcohol, and slowly dropped into the reaction system in about 3 hours. Subsequently, the reaction suspension continued to reflux and stir at 90° C. for 20 h. The reaction mixture was cooled to 50°C, about 40ml of glacial acetic acid was slowly added, and refluxed for 4h. Filter the reaction mixture through a fritted funnel. The resulting solid was filtered and washed repeatedly with methanol and water until the solution was almost colorless. Drying under vacuum at 80°C...

Embodiment 2

[0030] Synthesis of pyrrolopyrrolidone-fluorene copolymer (P1): the reaction system uses high-purity N 2 emptying. 0.201g (0.3mmol) and 0.151g of 2,5-dioctyl-3,6-di(4-bromophenyl)pyrrolo[3,4c]pyrrole-1,4-dione prepared in Example 1 2,7-bis(trimethylene borate)-9,9-dihexylfluorene (F1) (0.3mmol), 0.69g K 2 CO 3 (5mmol) and 0.007g tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 (0.006mmol) at N 2 Dissolve in a mixed solvent of 5mL tetrahydrofuran (THF) and 5mL water under protected conditions. Keep the temperature at 80°C and stir vigorously for 48h. Add 0.012g F1 (0.018mmol) to the reaction system, keep the temperature at 80°C, and stir for 6h; then add 0.008g of 2-bromo-9,9-dioctylfluorene (E) (0.018mmol), keep the temperature at 80°C, and stir for 6h . The reaction mixture was cooled and precipitated into methanol to give a solid. Filter, wash the solid with dilute hydrochloric acid, dissolve the solid again in chloroform, and precipitate in acetone. The prod...

Embodiment 3～9

[0032] The synthesis of pyrrolopyrrolidone-fluorene copolymer (P1): the preparation process is the same as in Example 2, the difference is to use NaHCO 3 , K 3 PO 4 , Na 2 CO 3 and Et 3 N as base instead of K 2 CO 3 , using different organic solvents and different solvent ratios, and different reaction times. Concrete alkali consumption, organic solvent and specific solvent proportion and reaction time are shown in Table 1 in each embodiment. The molecular weights of the obtained polymers are also different in each embodiment due to the difference in reaction conditions. The maximum photoluminescence wavelength λ of all the prepared copolymers in the film p1 It is 600-610nm; their luminescent wavelength is in the red light region, and they are good photoluminescent red light materials. The maximum electroluminescent wavelength λ of the copolymer in the device structure ITO / PEDOT / P1 / Ba / Al is 590-610nm, and their luminescent wavelength is in the red light region, so the...

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Abstract

The invention discloses pyrrolopyrrolidine-diones-fluorenyl copolymer electroluminescent material and the preparing method. Said electroluminescent material comprises two structural units: pyrrolopyrrolidine-diones and fluorenyl, and the weight average molecular weight is 10000- 100000. The preparing method comprises following steps: dissloving pyrrolopyrrolidine-diones monomer, fluorenes (trimethyleneboric acid ester), tetrapalladium (triphenylphosphine) and K2CO3 in organic solvent under protection of nitrogen gas, reacting at 50- 100 Deg. C; adding 2- bromine fluorenes colsing agent, reacting; cooling, depositing, filtering, washing, extracting and getting final product. The material can adsorb light with wave length being 300- 600 nm, and the maximium electroluminescence wave length is 590- 610 nm, and the light-emitting wave length is in red region.

Description

technical field [0001] The invention relates to an electroluminescence material, in particular to a pyrrolopyrrole dilidone-fluorene copolymer electroluminescence material and a preparation method thereof. Background technique [0002] Since no single polymer or small molecule material has been found to efficiently generate saturated white light, current OLED and PLED technologies can only use three primary colors (RGB) superposition schemes, whether for background lighting or full-color display. Practical three-primary-color materials should have these characteristics: high-efficiency fluorescence quantum efficiency, saturated color purity, narrow emission band, uniform and dense film formation and good thermal stability. [0003] High performance green light [Kido J., Lizumi Y.Appl.Phys.Lett.1998, 73:2721] and blue light [GaoZ.Q., Lee S.C., Bello I., et al.Appl.Phys.Lett.1999 , 74:865] materials have been practical, while red light materials are relatively backward. The ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06H05B33/14
Inventor 曹德榕刘其林
Owner SOUTH CHINA UNIV OF TECH
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