CN103739607A - Tri-carbazole multi-arm structural red-light--emitting material and preparation method and application thereof - Google Patents
Tri-carbazole multi-arm structural red-light--emitting material and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to a tri-carbazole multi-arm structural red-light-emitting material and a preparation method and application thereof, and in particular relates to a star-like oligomer which utilizes tri-carbazole as a core and a thiophene-diazosulfide derivate and other aryl compounds as arms, and an application of the star-like oligomer in the electro-optic field. The alkyl chain of the star-like oligomer is modified, and the star-like oligomer can be dissolved in a polar solvent. The tri-carbazole multi-arm structural red-light-emitting material has a general formula structure as shown in formula (b) I (/b) as shown in description. According to the preparation method, the materials are synthesized to be a monomer by Suzuki reaction; the raw materials are at low price; and the synthesis method is simple and convenient. Such material shows outstanding luminescence property, high thermal stability and spectral thermal stability, and has an important application potential in the organic electroluminescence, organic solar cells and other fields; an electroluminescent device manufactured through the material shows remarkable luminance, luminous efficiency, resistance to voltage stability, etc.
Description
Technical field
The present invention relates to photoelectric material and applied technical field, be specifically related to a kind of electroluminescent organic material, more specifically based on three and carbazole multi-arm structure red light material and methods for making and using same thereof, it take three and the carbazole multi-arm structured materials that are an arm as core, the thiophene-diazosulfide derivative of take, and carry out polar functional group modification at its side chain, be widely used in organic electro-optic device, particularly organic electroluminescent LED, organic solar batteries etc.
Background technology
Organic electroluminescent (OLED) refers under certain electric field, and organic materials is excited by corresponding electric energy, the luminescence phenomenon producing when excited state is got back to ground state.That OLED has advantages of is all solid state, spectral width, brightness are high, fast response time, that energy consumption is low, operating temperature range is wide etc. is very outstanding.Making aspect processing, because organic electroluminescence device is to utilize vapour deposition method or spin-coating method to carry out deposit film, big area manufacturing process is fairly simple, and cost is relatively low, therefore in demonstration, illumination and the field such as communicate by letter, has great application potential.
The research of organic electroluminescent starts from 1963, and early stage report comes from HeM. Pope study group of R.E. Visco study group, and specific experiment condition is to add high direct voltage in the anthracene single crystal sheet both sides of micron thickness, can observe blue emission; Afterwards, Tang etc. designed and produced organic electroluminescence device prepared by sandwich structure, and aryl diamine is as hole transmission layer, and 8-hydroxy-quinoline, as luminescent layer, has reported that the device brightness being less than under 10V voltage is up to 1000cd/m
2, the green organic electrofluorescence device that external quantum efficiency is 1%, this indicates that organic electroluminescent technology enters and breeds the practical epoch.
In recent years, due to the impact of global energy crisis, the research of white light OLED is more and more subject to related researcher's extensive attention, realize big area full color and show, the red, green, blue three primary colours of stability and high efficiency are indispensable.And ruddiness is as one of three primary colours, be the key of the efficient white light OLED of preparation, realize high stable, high efficiency red light material and device thereof and remain the challenging problem in organic electroluminescent field.For addressing this problem, people have carried out a lot of research work.Can there is intramolecular charge transfer process in DCM compounds, have long wavelength's fluorescent emission, is the good emitting red light dyestuff of a class, in OLED, be widely used, but this class luminescent dye still exists some shortcomings.Organic electroluminescence device performance is largely subject to the impact of purity and the luminous efficiency of this material, and the purifies and separates difficulty of DCM compounds material and emission wavelength are undesirable is comparison stubborn problem always.
Three and carbazole and thiophene-diazosulfide structural motif there is the two dimensional structure of rigidity, send blood orange light or ruddiness, and the lumo energy of this compounds is lower, so the injection of electronics and transmittability obtained effective raising, is the red light material that a class has application potential very much.They have clear and definite chemical structure, have moderate molecular weight and highly branched molecular structure, and can purify and obtain quite high chemical purity by easy column chromatography method, effectively avoid catalyst residue and other small molecular weight impurity for the impact of device performance; Overcome the intrinsic poor repeatability of red light material in the past simultaneously, be difficult to the shortcomings such as purification.These unique characteristics make this class multi-arm structured material have appreciable application prospect realizing aspect the organic film photoelectric device of stability and high efficiency.
Summary of the invention
The object of this invention is to provide a kind of efficient stable red light material cheap and easy to get and preparation method thereof, this material synthesizes simply, is easy to volume production, is easy to purifying, can be used as luminescent material and be applied to organic luminescent device, be particularly applied to prepare the white light organic electroluminescence thin-film device of stability and high efficiency.
The present invention proposes a kind of based on three and carbazole multi-arm structure red light material and preparation method thereof and application, it is based on three and carbazole multi-arm structure red light material, this material take three and the carbazole multi-arm structural compounds that are an arm as core, the thiophene-diazosulfide derivative of take, and its formula is as shown in the formula shown in I:
Wherein, R is C
1c
12alkyl, Ar is thiophene-diazosulfide derivative.
Based on three and the preparation method of carbazole multi-arm structure red light material, adopt bromo thiophene-diazosulfide derivative with three and carbazole boric acid ester by Suzuki, react, preparation is based on three carbazole multi-arm structure red light materials also:
Wherein, R is C
1c
12alkyl, Ar is thiophene-diazosulfide derivative.
This reaction is at Pd (PPh
3)
4under katalysis there is Suzuki linked reaction in monomer 1 and 2.
Based on the three also application of carbazole multi-arm structure red light material, this material is applied to organic electroluminescence device, device architecture is anode/hole injection layer/luminescent layer/electron transfer layer/electron injecting layer/negative electrode, wherein three and carbazole multi-arm structure red light material as luminescent layer.
Three and the carbazole multi-arm structure red light material that the present invention proposes have clear and definite chemical structure, moderate molecular weight, synthesis technique simple, be easy to purifying, be easy to volume production, can purify and obtain quite high chemical purity by easy column chromatography method.The molecular structure of star-like branchedization, not only contribute to suppress the gathering of stiff molecule interchain, reduce crystallization tendency, improve the second-order transition temperature of material, reduce the cancellation effect of material when solid-state simultaneously, significantly strengthened the solid-state light emission performance of target material.Especially, thiophene is that common p-type is to electronic structure unit, diazosulfide is that typical N-shaped is subject to electronic structure primitive, and the band gap that the quantity by reasonable adjusting p, n primitive and content can Effective Regulation multi-arm structured materials, has obtained narrower gap structure and wider spectral absorption.Using this material can obtain efficient red electroluminescent transmitting and excellent spectrum and device stability energy as the organic electroluminescence device of luminescent layer, is a kind of electroluminescent organic material with important application prospect.
Accompanying drawing explanation
Fig. 1 is synthetic three and the carbazole multi-arm structure red light material P1's obtaining of the present invention
1h NMR figure;
Fig. 2 is the MALDI-TOF mass spectrum of synthetic three and the carbazole multi-arm structure red light material P2 obtaining of the present invention;
Fig. 3 is the MALDI-TOF mass spectrum of synthetic three and the carbazole multi-arm structure red light material P3 obtaining of the present invention;
Fig. 4 is the device Electroluminescence Properties chart of synthetic three and the carbazole multi-arm structure red light material P1-P3 obtaining of the present invention;
Fig. 5 is that the synthetic target compound P1-P3 obtaining of the present invention is at DCM solution UV and PL curve;
Fig. 6 is that the synthetic target compound P1-P3 obtaining of the present invention is at UV and the PL curve of film state;
Fig. 7 is building-up reactions route a of the present invention;
Fig. 8 is building-up reactions route b of the present invention;
Fig. 9 is building-up reactions route c of the present invention.
Embodiment
Below in conjunction with accompanying drawing, the present invention will be further described, and based on three and carbazole multi-arm structure red light material, this material take three and the carbazole multi-arm structural compounds that are an arm as core, the thiophene-diazosulfide derivative of take, and its formula is as shown in the formula shown in I:
Wherein, R is C
1c
12alkyl, Ar is thiophene-diazosulfide derivative.
Embodiment 1:
According to reaction scheme a, compound 1 mixes in tetrahydrofuran solvent with salt of wormwood and TBAB, and 80
ounder C condition, slowly add bromo normal hexane, reaction obtains 2.Be dissolved in phosphorus oxychloride 2,100
othe condition of C, reaction obtains 3.By 3, mix in new steaming dioxane solvent with two boric acid esters and potassium acetate, at Pd (dppf
2) Cl
2make catalyzer, 100
ounder the condition of C, reaction obtains 4.Compound 5 is dissolved in new steaming tetrahydrofuran solvent ,-78
oafter reacting with butyllithium under the condition of C, add Virahol tetramethyl ethylene ketone boric acid ester, obtain 6.By 6, mix in solution of potassium carbonate and toluene solvant with dibromo diazosulfide, at four triphenyl phosphorus palladiums, make catalyzer, 95
othe conditioned response of C, reaction obtains 7.By 7,4 and potassium hydroxide and TBAB in tetrahydrofuran solvent, mix, at Pd (PPh
3)
4do under the condition of catalyzer, Suzuki linked reaction occurs and make target compound P1, its reaction scheme a as shown in Figure 7.Accompanying drawing 1 is for its three and carbazole multi-arm structure red light material P1's obtaining in synthetic
1h NMR figure.
Target compound P1 is as the preparation of the organic electroluminescence device D1 of luminescent layer:
The structure of device is ITO/PEDOT:PSS (20 nm)/P1:MADN=1%/BCP (30 nm)/LiF (1.2 nm)/Al (80 nm); Wherein P1 is three and carbazole multi-arm structure red light material, as luminescent layer, and prepares for vapour deposition method.
Embodiment 2:
-------target compound P2
According to reaction scheme b, compound 8 is dissolved in new steaming tetrahydrofuran solvent ,-78
oafter reacting with butyllithium under the condition of C, add Virahol tetramethyl ethylene ketone boric acid ester, obtain 9.By 9, mix in solution of potassium carbonate and toluene solvant with dibromo diazosulfide, at four triphenyl phosphorus palladiums, make catalyzer, 95
othe conditioned response of C, reaction obtains 10.By 10,4 and potassium hydroxide and TBAB in tetrahydrofuran solvent, mix, at Pd (PPh
3)
4do under the condition of catalyzer, Suzuki linked reaction occurs and make target compound P2, its reaction scheme b as shown in Figure 8.Accompanying drawing 2 is the MALDI-TOF mass spectrum of its three and carbazole multi-arm structure red light material P2 obtaining in synthetic.
Target compound P2 is as the preparation of the organic electroluminescence device D2 of luminescent layer:
The structure of device is ITO/PEDOT:PSS (20 nm)/P2:MADN=0.5%/BCP (30 nm)/LiF (1.2 nm)/Al (80 nm); Wherein P2 is three and carbazole multi-arm structure red light material, as luminescent layer, and prepares for vapour deposition method.
Embodiment 3:
By 9, mix in solution of potassium carbonate and toluene solvant with dibromo diazosulfide, at four triphenyl phosphorus palladiums, make catalyzer, 95
othe conditioned response of C, reaction obtains 11.By 11, mix in DMF solvent with NBS, reaction obtains 12.By 12,4 and potassium hydroxide and TBAB in tetrahydrofuran solvent, mix, at Pd (PPh
3)
4do under the condition of catalyzer, Suzuki linked reaction occurs and make target compound P3, its reaction scheme c as shown in Figure 9.Accompanying drawing 3 is the MALDI-TOF mass spectrum of its three and carbazole multi-arm structure red light material P3 obtaining in synthetic.
Target compound P3 is as the preparation of the organic electroluminescence device D3 of luminescent layer:
The structure of device is ITO/PEDOT:PSS (2 nm)/P3:MADN=0.5%/BCP (30 nm)/LiF (1.2 nm)/Al (80 nm); Wherein P3 is three and carbazole multi-arm structure red light material, as luminescent layer, and prepares for vapour deposition method.
The device Electroluminescence Properties chart that accompanying drawing 4 is three and the carbazole multi-arm structure red light material P1-P3 that obtain in synthetic example 4-6, accompanying drawing 5 is that compound P1-P3 is at DCM solution UV and PL curve, accompanying drawing 6 be compound P1-P3 at UV and the PL curve of film state, result shows it is the good red light material of a class.
Three and the carbazole multi-arm structure red light material that the present invention proposes have clear and definite chemical structure, moderate molecular weight, synthesis technique simple, be easy to purifying, be easy to volume production, can purify and obtain quite high chemical purity by easy column chromatography method.The molecular structure of star-like branchedization, not only contribute to suppress the gathering of stiff molecule interchain, reduce crystallization tendency, improve the second-order transition temperature of material, reduce the cancellation effect of material when solid-state simultaneously, significantly strengthened the solid-state light emission performance of target material.Especially, thiophene is that common p-type is to electronic structure unit, diazosulfide is that typical N-shaped is subject to electronic structure primitive, and the band gap that the quantity by reasonable adjusting p, n primitive and content can Effective Regulation multi-arm structured materials, has obtained narrower gap structure and wider spectral absorption.Using this material can obtain efficient red electroluminescent transmitting and excellent spectrum and device stability energy as the organic electroluminescence device of luminescent layer, is a kind of electroluminescent organic material with important application prospect.
Although we are in conjunction with exemplary embodiment, the present invention has been described particularly, but it will be appreciated by those skilled in the art that in the situation that do not depart from the spirit and scope of the present invention that the claims limit, can make in form and details various modifications and change.
Claims (3)
1. based on three and carbazole multi-arm structure red light material and preparation method thereof and application, it is characterized in that, this material based on three and carbazole structure primitive be core, and there is following chemical structure of general formula:
Wherein, R is C
1c
12alkyl, Ar is thiophene-diazosulfide derivative, can be following several functional group.
2. according to claim 1 based on three and the preparation method of carbazole multi-arm structure red light material, it is characterized in that, this material is as the luminescent layer of organic electroluminescence device, and design device architecture is anode/hole injection layer/luminescent layer/electron transfer layer/electron injecting layer/negative electrode.
3. according to claim 1 based on three and the preparation method of carbazole multi-arm structure red light material, it is characterized in that, adopt bromo thiophene-diazosulfide derivative with three and carbazole boric acid ester by Suzuki, react, preparation is based on three carbazole multi-arm structure red light materials also:
Wherein, R is C
1c
12alkyl, Ar is thiophene-diazosulfide derivative, this reaction is at Pd (PPh
3)
4under katalysis there is Suzuki linked reaction in monomer 1 and 2.
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| US20200181157A1 (en) * | 2018-12-05 | 2020-06-11 | Lg Display Co., Ltd. | Organic compound, light emitting diode and light emitting device having the compound |
| CN111875607A (en) * | 2016-06-16 | 2020-11-03 | 正大天晴药业集团股份有限公司 | Preparation method of chiral pyrrolopyrimidine compound |
| CN112079840A (en) * | 2020-08-03 | 2020-12-15 | 浙江工业大学 | Indole derivative-thiophene compound and preparation and application thereof |
| CN112079849A (en) * | 2020-08-14 | 2020-12-15 | 浙江工业大学 | Indole derivative-proEDOT compound and preparation and application thereof |
| CN112094282A (en) * | 2020-08-03 | 2020-12-18 | 浙江工业大学 | Indole derivative-EDOT compound and preparation and application thereof |
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| CN105949205A (en) * | 2016-05-11 | 2016-09-21 | 南京邮电大学 | Nitrogen-atom-doped condensed-nucleus aromatic hydrocarbon compounds as well as preparation method and application thereof |
| CN111875607A (en) * | 2016-06-16 | 2020-11-03 | 正大天晴药业集团股份有限公司 | Preparation method of chiral pyrrolopyrimidine compound |
| CN111875607B (en) * | 2016-06-16 | 2021-12-03 | 正大天晴药业集团股份有限公司 | Preparation method of chiral pyrrolopyrimidine compound |
| US20200181157A1 (en) * | 2018-12-05 | 2020-06-11 | Lg Display Co., Ltd. | Organic compound, light emitting diode and light emitting device having the compound |
| US11673895B2 (en) * | 2018-12-05 | 2023-06-13 | Lg Display Co., Ltd. | Organic compound, light emitting diode and light emitting device having the compound |
| CN112079840A (en) * | 2020-08-03 | 2020-12-15 | 浙江工业大学 | Indole derivative-thiophene compound and preparation and application thereof |
| CN112094282A (en) * | 2020-08-03 | 2020-12-18 | 浙江工业大学 | Indole derivative-EDOT compound and preparation and application thereof |
| CN112094282B (en) * | 2020-08-03 | 2023-06-09 | 浙江工业大学 | Indole derivative-EDOT compound and preparation and application thereof |
| CN112079840B (en) * | 2020-08-03 | 2023-06-27 | 浙江工业大学 | Indole derivative-thiophene compound and preparation and application thereof |
| CN112079849A (en) * | 2020-08-14 | 2020-12-15 | 浙江工业大学 | Indole derivative-proEDOT compound and preparation and application thereof |
| CN112079849B (en) * | 2020-08-14 | 2023-06-27 | 浙江工业大学 | Indole derivative-proEDOT compound and preparation and application thereof |
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Application publication date: 20140423 |