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Twist structured p-phenylene ethylene luminous polymer and use thereof

A technology of p-phenylene vinylene and light-emitting polymers, which is applied in the field of conjugated light-emitting polymers, can solve problems such as low carrier mobility, difficulty in blue light, and limited range of blue shift, so as to improve blue light-emitting performance, Effect of improving quantum efficiency and inhibiting association

Inactive Publication Date: 2004-06-09
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the methods for obtaining blue-emitting PPV are not very successful. For example, the PPV oligomers are connected by flexible chains. Although blue-emitting materials can be obtained, the device efficiency is very low due to very low carrier mobility; the use of side chains The steric hindrance effect of the substituent group reduces the planarity of the main chain, which can blue-shift the spectrum, but the blue-shift range is limited, and it is difficult to achieve pure blue light

Method used

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  • Twist structured p-phenylene ethylene luminous polymer and use thereof
  • Twist structured p-phenylene ethylene luminous polymer and use thereof
  • Twist structured p-phenylene ethylene luminous polymer and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0046]Embodiment 1 6-cyclohexyl-2, the synthesis of 10-dialdehyde-bisphenyl [d, f] [1,3] bisoxazepine (synthetic route sees figure 2 ) Dissolve compound 1 (2,2'-dihydroxybiphenyl) in dichloromethane, stir vigorously at room temperature, add equimolar bromine, stop the reaction when precipitation occurs, and obtain compound 2a, 5, 5 '-Dibromo-2,2'-dihydroxybiphenyl,

[0047] Dissolve compound 2a (5,5'-dibromo-2,2'-dihydroxybiphenyl) in benzene, add p-toluenesulfonic acid and equimolar 2,2'-dimethoxycyclohexane, heat, Remove the components at 57-59°C, stop the reaction, and neutralize with sodium methoxide. Extracted with ether, dried over anhydrous sodium sulfate, removed the solvent, and recrystallized from ethanol to obtain compound 3a (6,6-cyclohexyl-2,10-dibromo-bisphenyl[d,f][1,3]bisoxazene ),

[0048] Compound 3a (6,6-cyclohexyl-2,10-dibromo-bisbenzo[d,f][1,3]bisoxazepine) was added to 20 ml of dry tetrahydrofuran under nitrogen protection. Add n-BuLi (n-butyllithium)...

Embodiment 2

[0049] Example 2 Twisted monomer 2', 3 "-dialdehyde-5, the synthetic route of 7-diphenylthiatable table (route see image 3 ) Add NBS (N-bromosuccinimide) to 85% sulfuric acid solution of compound 1 and stir vigorously for 1 hour, add water and stir, extract with acetone, and recrystallize with DMSO (dimethyl sulfoxide) to obtain compound 2b;

[0050] In the presence of oxygen, the mixture of compound 2b and ketone chloride was dissolved in pyridine and stirred for 6 hours, extracted with ether, dried and recrystallized to obtain compound 3b,

[0051] NaBH 4 Slowly add to THF (tetrahydrofuran) and cool to -78°C, add SnCl under nitrogen 4 , vigorously stirred for 30min, and the temperature was raised to 0°C, the THF solution of compound 3b was added dropwise to the above solution once, slowly brought to room temperature and vigorously stirred for 48h, then poured into ice water, extracted with ether, dried, and column chromatographed to obtain the compound 4b; After acidific...

Embodiment 3

[0054] Example 3 Wide Bandgap Blue Light Emitting PPV-like Polymers

[0055] Synthesis of SCHDDBDOP-PPV (poly(2,10-(6-cyclohexyl-bisphenyl [d, f] [1,3] dioxazepine)-1,4 phenylene vinylene)) (route see Figure 4 )

[0056] The dried drug 2,5-dibromomethylbenzene and triphenylphosphine were distilled in DMF (N,N-dimethylformamide) for 14 hours at a molar ratio of 1:2.02, and the phosphine was filtered out after cooling. The salt precipitated, washed with p-xylene and dried. Under nitrogen protection conditions, in a fully dry reaction device, add phosphine salt, potassium tert-butoxide, and drug 4a in a molar ratio of 2:3:2.02, react in THF at 0°C for 6 hours, wash with methanol four times, Dry to obtain a polymer.

[0057] The optical properties of the above-mentioned blue light-emitting PPV polymers:

[0058] The absorption and emission spectra of the blue light-emitting polymer SCHDDDOP-PPV in solution and film (excitation light source is 350nm) such as Figure 5 As show...

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Abstract

The present invention relates to a p-phenylene ethylene luminous polymer with twisted structure. It is characterized by that it is made up by introducing the bridged heptatomic heterocyclic monomer into the main chain of P-phenylene ethylene (PPV) and its derivative. Said invention can obviously raise blue luminous capability, and is suitable for preparing polymer LRD, optical pump and electric pump laser and semiconductor device of field-effect transistor, etc.

Description

technical field [0001] The invention relates to a conjugated luminescent polymer, in particular to a twisted p-phenylene vinylene (hereinafter referred to as PPV)-based luminescent polymer and its application Background technique [0002] In 1990, the University of Cambridge reported the electroluminescent properties of conjugated polymer PPV, and many related π-conjugated polymers with luminescent properties were synthesized one after another, such as MEH-PPV (alkoxy-substituted PPV), CN-PPV (cyanide PPV) and so on. With the in-depth study of organic polymer semiconductors, the commercial application prospects of polymer semiconductors for display technology are becoming clearer. The world market for organic and polymer light-emitting materials for displays is enormous. PPV materials are the electroluminescent materials with the best performance at present, but according to the current situation, PPV and its derivatives that emit green light and orange-red light have exce...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F112/32H05B33/02
Inventor 马於光张海全何凤沈方中李昱鹏沈家骢
Owner JILIN UNIV
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