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CN1600759A - PPV-like Luminescent Oligomer Containing Biphenyl Center - Google Patents

PPV-like Luminescent Oligomer Containing Biphenyl Center Download PDF

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CN1600759A
CN1600759A CNA031600190A CN03160019A CN1600759A CN 1600759 A CN1600759 A CN 1600759A CN A031600190 A CNA031600190 A CN A031600190A CN 03160019 A CN03160019 A CN 03160019A CN 1600759 A CN1600759 A CN 1600759A
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oligomer
ppv
light
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CN100491313C (en
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马於光
何凤
张海全
杨兵
郑岩
林栋�
唐诗
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Jilin University
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Abstract

本发明为含有联苯中心的PPV类发光齐聚物，制作步骤包括：1.中心单体的结构与合成，引入具有两个或多个联苯的多官能团结构中心物质类似于A，B，C，D，E，F；所述的化合物为具有扭曲度的共轭环；2、侧链单体的选择和合成；3、齐聚物的合成，将单体A，B，C，D，E，F分别与侧链单体H反应，得到由于两个或多个联苯中心的苯撑乙烯齐聚物体系(1)、(2)、(3)、(4)；本发明的PPV类发光齐聚物，可以其合成出一系列具有优良的蓝光发射性能的、固体状态的新型双(多)三聚苯撑乙烯及其衍生物；并用其制成高效的蓝色发光二极管。

The present invention is a PPV-type luminescent oligomer containing a biphenyl center. The production steps include: 1. The structure and synthesis of the center monomer, introducing a multifunctional structure center substance with two or more biphenyls similar to A, B, C, D, E, F; the compound is a conjugated ring with twist; 2, the selection and synthesis of side chain monomers; 3, the synthesis of oligomers, the monomers A, B, C, D , E, F react with side chain monomer H respectively, obtain the phenylene vinylene oligomer system (1), (2), (3), (4) because of two or more biphenyl centers; PPV-based light-emitting oligomers can be used to synthesize a series of new bis(poly)tripolyphenylene vinylene and its derivatives in solid state with excellent blue light emission properties; and use them to make efficient blue light-emitting diodes.

Description

The luminous oligopolymer of PPV class that contains the biphenyl center
Technical field
The present invention relates to a kind of PPV base polymer, particularly a kind of luminous oligopolymer of PPV class that contains the biphenyl center.
Background technology
Pi-conjugated organic polymer is because its wide application prospect aspect electronic conduction, nonlinear optics, electronics and photoelectronics has caused numerous scientists' very big interest.Particularly as luminophore in the application aspect the Organic Light Emitting Diode, obtained very deep research.They have following advantage as the base mateiral of Organic Light Emitting Diode: comparatively simple preparation method; The controllability of glow color.And, not only can provide the microtexture information of corresponding polymeric system, and itself often also can be used as active substance and be used for multiple scientific research for us as the oligopolymer of the model compound of phase emergencing copolymer.Benefit from the determinacy of oligopolymer structure, make that its conjugate length is single distribution, and can change the length of oligopolymer segment according to actual needs, to regulate its conjugate length and glow color.Trimerization phenylene ethylene (TPV) and its derivative are as the model compound of PPV base polymer, obtained people's broad research, what is more important trimerization phenylene ethylene (TPV) itself is exactly a kind of blue excitation material, makes phenylene ethylene class oligopolymer seem particularly important.Yet many advantageous properties (for example fluorescence efficiency is higher than 90%) of trimerization phenylene ethylene (TPV) can only obtain under solution state, and can not obtain in that the solid film state is next.People are owing to intermolecular aggregated forms by the quenching phenomenon of discovering this solid film, particularly intermolecular in harness arrangement mode.Illustrate that intermolecular stacked form is the determinative of this class material physical properties.In order to solve the emission efficiency problem of this class material under solid state, people have done a large amount of adjustment and improvement on the TPV basis, for example: in TPV, introduce various substituted radicals, four TPV are connected on the carbon atom (C ( tBuSSB) 4) and the combination of the ring-type covalency of a plurality of TPV molecules (calyx[4] arene core).Some materials in them (for example C ( tBuSSB) 4) also be used to make device, but its device does not obtain the luminous efficiency close with solid film.Therefore, the continuation of many advantageous properties of trimerization phenylene ethylene (TPV) exploitation, particularly the high blue fluorescent emission efficient under the solid film state is one of important topic of industry.
Summary of the invention
The purpose of this invention is to provide a kind of luminous oligopolymer of PPV class that contains the biphenyl center, synthesize a series of have novel two (many) trimerization phenylene ethylenes and derivatives thereof good blue emission performance, solid state with it; And make blue LED efficiently with it.
The objective of the invention is to realize by following technical scheme.The present invention is the luminous oligopolymer of PPV class that contains the biphenyl center,
It is characterized in that it comprises following making step:
The structure of step 1, center monomer is introduced the polyfunctional group structure centre material type with two or more biphenyl and is similar to A, B, C, D, E, F with synthetic; This compounds is the conjugate ring with certain torsion resistance, for example, and for A:M 1=M 2=Br, the actual measurement distortion angle is 71.8 ° of (see figure 1)s:
Figure A0316001900071
Wherein, M 1, M 2, M 3, M 4Can be identical or different group :-PPh 3Br ,-PO (OC 2H 5) 2Br or-CN
Step 2, the monomeric selection of side chain and synthetic, the side chain monomer is selected H:
Described side chain monomer H is the material that a class contains single aldehyde functional group, wherein R 1, R 2, R 3, R 4, R 5(identical or different group) can be hydrogen atom, fluorine atom, phenyl ring, alkoxyl group (C1-C10), alkyl (C1-C10):
Synthesizing of step 3, oligopolymer, with monomer A, B, C, D, E, F react with side chain monomer H respectively, obtain because phenylene ethylene oligopolymer system (1), (2), (3), (4) at two or more biphenyl center:
Figure A0316001900081
Represent replacement situation on each end group phenyl ring with following formula: wherein, the former represents the replacement situation of phenylene ethylene oligopolymer system (1), (3), (4); The latter represents the replacement situation of phenylene ethylene oligopolymer system (2);
Phenyl ring in its Chinese style also can be: other aromatic nucleus such as naphthalene nucleus, pyridine
R 1, R 2, R 3, R 4, R 5, R 6(identical or different group) can be: hydrogen atom, fluorine atom, phenyl ring, alkoxyl group (C1-C10), alkyl (C1-C10 straight chain or branch chain), aromatic nucleus, pentanoic;
R (identical group) can be: hydrogen atom, cyano group are (CN);
X, Y, Z (can be identical or different atom) representative: C, O, S, Si, P, NO, S, N, C.
It has good emission efficiency in solid and organic electroluminescence device.
Described synthetic oligopolymer (1), (2), (3), (4) system be uncommon (Wittig reaction) route by loving and respect one's elder brother Wei or Wei Ti Xi-Huo Le (Wittig-Horner reaction) route or brain literary composition lattice (Knoevenagel condensation) route method synthetic.
Now with synthetic oligopolymer (1) system, with tetraphenyl ethylene base biphenyl TSB with and derivative CN-TSB be example, its synthetic method is described.Oligopolymer (1) system can be synthetic by above any method, and example is as follows: [the following document of synthesized reference (1) Z.Yang, B.Hu, F.E.Karasz, Macromolecules, 1995,28,6151. (2) H.-H.Horhold, M.Helbig, Makromol.Chem.Macromol.Symp., 1987,12,229. (3) ArnoKraft, Andrew C.Grimsdale, Andrew B.Holmes, Angew.Chem.Int.Ed.1998,37,402.]
1) uncommon (Wittig reaction) route of loving and respect one's elder brother Wei:
Nineteen fifty-three Germanization scholar Witting has found a famous reaction (1)With two microcosmic salts and dialdehyde condensation, obtained phosphorus Ye Lide with haloalkane and triphenyl phosphorus reaction, can be converted into carbon-carbon double bond to the two keys of carbon oxygen easily, therefore this class reaction is widely used in increasing compound synthetic of carbon-carbon double bond, naturally also become the first-selected route of synthetic phenylene ethylene (PPV) oligopolymer, concrete reaction is as follows:
Figure A0316001900091
1) Ti Xi-Huo Le Wei (Wittig-Horner reaction) route:
Wei, Ti Xi-the Huo Le reaction was to replace triphenyl phosphorus with triethoxy phosphorus on the basis of wittig reaction, has further improved this reaction.
Figure A0316001900092
2) brain literary composition lattice (Knoevenagel condensation) route:
Brain literary composition reaction grid (2)Be based in the alkaline environment cyano group and can form carbon-carbon double bond, thereby can be widely used in synthetic cyanogen class PPV with the aldehyde radical effect.
3 make device, are luminescent layer with oligopolymer (1), (2), (3), (4) system, utilize the method film forming of vacuum evaporation or the spin coating of high speed sol evenning machine, can prepare blue efficiently or other colour light emitting device.
Polymkeric substance and device advantage by the present invention's acquisition:
(1) can regulation and control substance interaction between the molecule, thereby suppressed association between the molecule, improved the quantum yield of luminescent device.
(2) can be by changing end-group structure, adjustable effective conjugate length, thereby the luminosity of controlled material and device efficiency.(3) can also pass through R 1, R 2, R 3, R 4, R 5, R 6The variation solvability of regulating oligopolymer, can form solids, be easy to the thickness of control device luminescent layer.
(4) can obtain the luminescent device broad stopband, that purity of color is high.
In sum, oligopolymer of the present invention is to have novel two (many) trimerization phenylene ethylenes and derivative thereof good blue emission performance, solid state; Be applicable to semiconducter device such as preparation Organic Light Emitting Diode, optical pumping and electric pump laser, field-effect transistor.
Description of drawings
Fig. 1 records center cell 2,5 for utilizing Rigaku R-AXIS RAPID type single crystal diffractometer, 2 ', 5 '-the X-ray structure iron of tetrabromo methyl diphenyl, the twist angle that records two phenyl ring is 71.8 °.
Fig. 2 is the synthetic route chart of oligopolymer TSB and TBVB.
Fig. 3 is the synthetic route chart of oligopolymer TFB.
Fig. 4 is the synthetic route chart of terphenyl center oligopolymer.
Fig. 5 is the structure iron that utilizes the electroluminescent device of oligopolymer preparation of the present invention.
Specific embodiments
Further illustrate preparation, the character of monomer and oligopolymer among the present invention below by embodiment; And be the luminescent device that luminescent layer is made with these oligopolymers.
Embodiment 1 is oligopolymer system synthetic at center with biphenyl, synthetic route such as Fig. 2.
The structure of step 1, center monomer is with synthetic
Preparation 2; 5; 2 '; 5 '-tetramethyl biphenyl: with triphenyl phosphorus (4.012g, 14.4mmol); 2,2 '-dipyridyl (0.316g; 2mmol); Nickel Chloride (0.26g; 2mmol) and zinc powder (0.0052g 80mmol) joins at the bottom of the garden of 100mL in the flask, adds the anhydrous N of 20mL under the nitrogen protection again; N '-dimethyl formamide; reaction then adds the 2-bromo-1 of 5.5mL (40mmol), the 4-dimethyl benzene in 50 ℃ of oil baths after forming dark brown catalyzer; and temperature of reaction is elevated to 80 ℃; reacted again under the nitrogen protection 8 hours; reaction finishes after-filtration and removes residual solid matters such as zinc powder, and decompression is spin-dried for and uses column chromatography purification after the filtrate and can obtain 2,5; 2 '; 5 '-tetramethyl biphenyl, decompression is spin-dried for and obtains white solid, productive rate 70%.
Preparation 2; 5,2 ', 5 '-the tetrabromo methyl diphenyl: 2; 5; 2 ', 5 '-tetramethyl biphenyl ((2.103g, 10mmol)), NBS (7.832g; 44mmol) and the benzoyl peroxide of catalytic amount add at the bottom of the garden of 100mL among the flask; the tetracol phenixin nitrogen protection that adds 40mL again refluxes down after 5 hours after-filtration remove solid residue, and decompression uses column chromatography after being spin-dried for filtrate, recrystallization is purified can obtain white product, and productive rate is 60%.
Preparation phosphonium salt: with compound 2,5,2 ', 5 '-the tetrabromo methyl diphenyl (0.5218g, 1mmol) and triphenyl phosphorus (1.154g 4.4mmol) is dissolved in anhydrous N, in N '-dimethyl formamide, behind the heating reflux reaction 18 hours, can obtain the white powder product, productive rate 60% with the filtration of anhydrous diethyl ether post precipitation.
Step 2, the monomeric selection of side chain and synthetic, the side chain monomer is selected H:
For simple side chain monomer, we can directly choose from existing aldehyde material, for example used phenyl aldehyde in the following steps, to the phenyl phenyl aldehyde.
And for comparatively complicated single aldehyde radical functional compounds, can be by first bromination, the reaction scheme of aldehyde radicalization obtains again.Below with synthetic 9,9 '-dihexyl-1-fluorenes formaldehyde is example, its concrete synthetic method is described, synthetic route such as Fig. 3:
Preparation 2-bromo fluorenes: successively with 5g (60mmol) fluorenes, 0.26g FeCl 3Be dissolved among the 50mlDMF, 6g (34mmol) NBS is dissolved among the 60mlDMF slowly splashes into reacting at normal temperature without light 24 hours.Reaction finishes the back and adds dilute hydrochloric acid to system, adds the saturated sodium carbonate neutralization again, chloroform extraction three times, and solvent evaporated normal hexane recrystallization gets white solid 4.18g, productive rate 56%.
Preparation 9,9 '-dihexyl-2-bromine fluorenes: add 1g (4.08mmol) 2-bromo fluorenes successively, 1.7ml (12mmol) C 6H 13Br, 0.129g (0.4mmol) TBABr, 0.48mlNaOH (50%W/W) is heated to 90 ℃ of reactions 24 hours.Reaction adds little water after finishing, and chloroform extraction three times is spin-dried for solvent and gets the 0.68g colourless viscous liquid with hexanaphthene developping agent column chromatography, productive rate 41%.
Preparation 9; 9 '-dihexyl-1-fluorenes formaldehyde: with 9; 9 '-dihexyl-1-bromine fluorenes (0.413g; 1mmol), tetrahydrofuran (THF) (15mL) joins at the bottom of the garden of 50mL in the flask; make temperature of reaction remain on-78 ℃ under the nitrogen protection, in reaction system, add the 0.7mL n-Butyl Lithium then, adding the anhydrous N of 0.4mL after 3 hours in reaction under this temperature; N '-dimethyl formamide (DMF) then reacted 12 hours.Reaction finishes the back decompression and is spin-dried for solvent, obtains faint yellow viscous liquid material, use column chromatography purification can obtain 9,9 '-dihexyl-1-fluorenes formaldehyde, decompression is spin-dried for and obtains colourless viscous liquid, productive rate 66%.
Synthesizing of step 3, oligopolymer.
Preparation 2,5,2 ', 5 '-tetraphenyl ethylene base biphenyl (TSB): the salt 4 of seeing (0.158g, 0.1mmol) and phenyl aldehyde (0.064g, 0.6mmol) be dissolved in isopyknic ethanol of 20mL and the tetrahydrofuran (THF) mixed solvent, at room temperature to wherein dripping 3mL 5% ground alcohol sodium alcohol solution, react water cancellation reaction after 12 hours then, repeated precipitation can obtain flaxen powder mass in methyl alcohol, be oligopolymer TSB, productive rate 84%.
Preparation 2,5,2 ', 5 '-tetrad styrylbiphenyl (TBVB): (0.158g is 0.1mmol) with to phenyl phenyl aldehyde (0.093g the salt 4 of seeing, 0.6mmol) be dissolved in isopyknic ethanol of 20mL and the tetrahydrofuran (THF) mixed solvent, at room temperature to wherein dripping 3mL5% ground alcohol sodium alcohol solution, react water cancellation reaction after 12 hours then, repeated precipitation can obtain jonquilleous powder mass in methyl alcohol, be oligopolymer TBVB, productive rate 86%.
Preparation 2,5,2 ', 5 '-four-(9,9 '-dihexyl-1-fluorenes) vinyl biphenyl (TFB): the salt 4 of seeing (0.158g, 0.1mmol) and 9,9 '-dihexyl-1-fluorenes formaldehyde (0.217g, 0.6mmol) be dissolved in isopyknic ethanol of 15mL and the tetrahydrofuran (THF) mixed solvent, at room temperature to wherein dripping 3mL 5% ground alcohol sodium alcohol solution, react water cancellation reaction after 12 hours then, repeated precipitation can obtain the xanchromatic powder mass in methyl alcohol, be oligopolymer TFB, productive rate 60%.
Through actual measurement, can find out the optical property of blue-light-emitting PPV oligopolymer, blue-light-emitting PPV oligopolymer TSB of the present invention, TBVB in solution, film absorption and the maximum absorption peak position of emmission spectrum (excitation light source is respectively 380nm and 395nm) respectively 360 and 376nm, the maximum absorption band of the two is red shift some (being about 356nm) than the trimerization PPV oligopolymer outline of strand all, and the introducing that has shown center biphenyl is not very big to the degree of gripping the altogether influence of each strand.In solution, two kinds of oligopolymers all show good blue-light-emitting, and photoluminescence efficiency is all more than 60%, and the emission maximum peak position is respectively 22nm (2.94eV) and 451nm (2.75eV).Compare with traditional strand PPV oligopolymer, the emission maximum peak position of two kinds of oligopolymer solid films of the present invention is compared the red shift of having only 20-30nm with its solution.In addition, PPV oligopolymer film of the present invention has not only shown blue-light-emitting character, and the fluorescence efficiency of its film also obtained large increase (for example TBVB is 34%), and usually typical PPV oligopolymer all is lower than 10% fluorescence efficiency φ＜10% of styryl benzene film (for example to).Therefore material of the present invention is liquid and solid-stately all have a high efficiency blue emission PPV class oligopolymer.
We can obtain (as Fig. 4) by the reaction similar with above-mentioned synthetic method for the oligopolymer system with santowax center more, final product is all fastened the product of stating several building-up reactionss (as wittig reaction), and this class material all has good electroluminescent character.
The preparation of embodiment 2 blue-light-emitting PPV oligopolymer electroluminescent devices
Be illustrated in figure 5 as the structure iron of multilayer organic light emitting diode device (OLEDs), described LED device comprises compound ITO layer, NPB layer, luminescent layer, Alq successively 3Layer, LiF layer, Al layer.In the present embodiment, the material of luminescent layer adopts the tetrad styrylbiphenyl TBVB of oligopolymer (1) system.This device is to handle 5 minutes with plasma oxygen with commercial ITO (scribbling the glass of tin indium oxide), on the evaporation behind the NPB, the oligopolymer of vacuum evaporation heat deposition again TBVB, and for the relatively large oligopolymer of molecular weight, then use the mode of sol evenning machine spin coating to make on the matrix of luminescent layer attached to ITO/NPB, so more help large-scale industrial production, at last vacuum evaporation lithium fluoride, aluminium electrode again.
The character of above-mentioned LED device: device shows blue emission, and recording cut-in voltage is 3V; Electroluminescent emission peak is: 440nm and 460nm; The CIE coefficient is: x=0.1726, y=0.1689; When voltage was 15V, maximum brightness was 2510cd/m 2Luminous efficiency is 1.62cd/A (luminous efficiency is 1.02lm/W).And existing PPV oligopolymer efficient is generally all less than 0.1cd/A, PPV oligopolymer LED device of the present invention has not only shown good blue-light-emitting, and its efficient also is greatly improved, can match in excellence or beauty with typical blue-light-emitting small molecules device (DPVBi, its efficient is about 1-4lm/W).

Claims (3)

1、一种含有联苯中心的PPV类发光齐聚物，其特征是：它包括如下制作步骤：1. A PPV-type luminescent oligomer containing a biphenyl center, characterized in that: it comprises the following manufacturing steps: 步骤1、中心单体的结构与合成，引入具有两个或多个联苯的多官能团结构中心物质类似于A，B，C，D，E，F；所述的化合物为具有一定扭曲度的共轭环，例如，对于化合物A：M1＝M2＝Br，扭曲角度为71.8°：Step 1, the structure and synthesis of the central monomer, the introduction of a multifunctional structural central substance with two or more biphenyls is similar to A, B, C, D, E, F; the compound is a compound with a certain twist For a conjugated ring, for example, for compound A: M 1 =M 2 =Br, the twist angle is 71.8°: 其中，M1、M2、M3、M4可以为相同或不同基团：-PPh3Br、-PO(OC2H5)2Br或-CNAmong them, M 1 , M 2 , M 3 , and M 4 can be the same or different groups: -PPh 3 Br, -PO(OC 2 H 5 ) 2 Br or -CN 步骤2、侧链单体的选择和合成，侧链单体选择H：Step 2. Selection and synthesis of side chain monomers, side chain monomer selection H: 所述侧链单体H是一类含有单醛官能团的物质，其中R1、R2、R3、R4、R5可为相同或不同基团，可以是氢原子、氟原子、苯环、烷氧基(C1-C10)、烷基(C1-C10)：The side chain monomer H is a type of substance containing a single aldehyde functional group, wherein R 1 , R 2 , R 3 , R 4 , and R 5 can be the same or different groups, and can be hydrogen atoms, fluorine atoms, benzene rings , Alkoxy (C1-C10), Alkyl (C1-C10):
Figure A031600190002C3
Figure A031600190002C3
 步骤3、齐聚物的合成，将单体A，B，C，D，E，F分别与侧链单体H反应，得到由于两个或多个联苯中心的苯撑乙烯齐聚物(1)、(2)、(3)、(4)体系：Step 3, the synthesis of oligomer, monomer A, B, C, D, E, F are reacted with side chain monomer H respectively, obtain the phenylene vinylene oligomer ( 1), (2), (3), (4) systems:
Figure A031600190003C1
Figure A031600190003C1
 以下式代表每个端基苯环上取代情况：其中，前者表示苯撑乙烯齐聚物体系(1)、(3)、(4)的取代情况；后者表示苯撑乙烯齐聚物体系(2)的取代情况： The following formula represents the substitution situation on each end group benzene ring: wherein, the former represents the substitution situation of the phenylene vinylene oligomer system (1), (3), (4); the latter represents the phenylene vinylene oligomer system ( 2) Replacement situation: 其中式中的苯环还可为：萘环、吡啶等其它芳香环The benzene ring in the formula can also be: naphthalene ring, pyridine and other aromatic rings R1、R2、R3、R4、R5、R6(相同或不同基团)可以是：氢原子、氟原子、苯环、烷氧基(C1-C10)、烷基(C1-C10直链或枝链)、芳香环、二苯胺；R 1 , R 2 , R 3 , R 4 , R 5 , R 6 (same or different groups) can be: hydrogen atom, fluorine atom, benzene ring, alkoxy group (C1-C10), alkyl group (C1- C10 straight chain or branched chain), aromatic ring, diphenylamine; R(相同基团)可以是：氢原子、氰基(-CN)；R (the same group) can be: hydrogen atom, cyano group (-CN); X、Y(可以为相同或不同原子)：O、S、N、CX, Y (can be the same or different atoms): O, S, N, C Z代表：C、O、S、Si、PZ stands for: C, O, S, Si, P 2、根据权利要求1所述的含有联苯中心的PPV类发光齐聚物，其特征是：所述的合成齐聚物(1)、(2)、(3)、(4)体系是通过魏悌希(Wittig reaction)路线或魏悌希-霍勒(Wittig-Horner reaction)路线或脑文格(Knoevenagel condensation)路线方法合成的。2. The PPV-based luminescent oligomer containing biphenyl center according to claim 1, characterized in that: the synthetic oligomer (1), (2), (3), (4) system is obtained by Synthesized by Wittig reaction route or Wittig-Horner reaction route or Knoevenagel condensation route method. 所述的齐聚物(1)体系的四苯乙烯基联苯TSB及其衍生物CN-TSB，其合成方法为：Tetrastyryl biphenyl TSB and derivative CN-TSB of described oligomer (1) system, its synthetic method is: (1)魏悌希(Wittig reaction)路线：(1) Wittig reaction route: 或为or for (2)魏悌希-霍勒(Wittig-Horner reaction)路线：(2) Wittig-Horner reaction route: 或为or for (3)脑文格(Knoevenagel condensation)路线：(3) Knoevenagel condensation route: 3、根据权利要求1所述的含有联苯中心的PPV类发光齐聚物为发光层的蓝色发光器件，其特征是：可利用真空蒸镀或高速匀胶机旋涂的方法成膜，制备高效的蓝色或其它颜色发光器件；3. The blue light-emitting device in which the PPV-type light-emitting oligomer containing biphenyl center is the light-emitting layer according to claim 1, which is characterized in that: the film can be formed by vacuum evaporation or spin coating with a high-speed coating machine, Preparation of highly efficient blue or other color light-emitting devices; 所述的发光器件包括依次复合的ITO层、NPB层、发光层、Alq3层、LiF层、Al层，所述的发光层的材料采用所述的齐聚物(1)或(2)或(3)或(4)体系。The light-emitting device comprises an ITO layer, an NPB layer, a light-emitting layer, an Alq3 layer, a LiF layer, and an Al layer compounded in sequence, and the material of the light-emitting layer adopts the oligomer (1) or (2) or (3) or (4) system.
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Cited By (5)

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CN100340582C (en) * 2005-08-12 2007-10-03 复旦大学 Fluorophenyl-containing PPV and its uses
CN102249944A (en) * 2009-12-08 2011-11-23 四川大学 Compound containing staggered biphenyl center and preparation method thereof
CN102533277A (en) * 2011-12-15 2012-07-04 石家庄诚志永华显示材料有限公司 Poly-fluorine polycyclic liquid crystal compound as well as preparation method and application thereof
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CN102249944A (en) * 2009-12-08 2011-11-23 四川大学 Compound containing staggered biphenyl center and preparation method thereof
CN102249944B (en) * 2009-12-08 2013-10-16 四川大学 Compound containing staggered biphenyl center and preparation method thereof
CN102533277A (en) * 2011-12-15 2012-07-04 石家庄诚志永华显示材料有限公司 Poly-fluorine polycyclic liquid crystal compound as well as preparation method and application thereof
CN102977341A (en) * 2012-11-15 2013-03-20 南京邮电大学 Preparation method and application of multiblock conjugated polymer containing phenylene ethylene skeleton
CN113735671A (en) * 2020-05-31 2021-12-03 首都师范大学 Bistyryl derivative molecule, synthetic method, single crystal and organic light-emitting field effect transistor device based on single crystal

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