CN100491313C - PPV luminescence oligomer containing biphenyl center - Google Patents

PPV luminescence oligomer containing biphenyl center Download PDF

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CN100491313C
CN100491313C CNB031600190A CN03160019A CN100491313C CN 100491313 C CN100491313 C CN 100491313C CN B031600190 A CNB031600190 A CN B031600190A CN 03160019 A CN03160019 A CN 03160019A CN 100491313 C CN100491313 C CN 100491313C
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oligopolymer
center
side chain
monomer
biphenyl
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CN1600759A (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

A process for syntheszing PPV luminous polymer which contains symbenzene center includes such steps as 1. synthesizing center monomer by inducting multitude functional group structure center substance which contains two or many symbenzene or be similar to A, B, C, D, E, F; the compound is skewness conjugation ring; 2. Selecting and synthesizing side chain monomer; 3. synthesizing the polymer by taking reaction A, B, C, D, E, F with side chain monomer H separately to get polymers of styrene with two or many symbenzene center.

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 neat thing 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 is obtained by center monomer and side chain monomer reaction, wherein:
1), the structure of center monomer is the polyfunctional group structure centre compd A with two or more biphenyl, B, C, D, E, F; Described compound is the conjugate ring (for example for compd A: M1=M2=Br, distortion angle are 71.8 °) with certain torsion resistance:
Figure C03160019D00061
Wherein, M 1, M 2, M 3, M 4Be selected from identical or different group :-PPh 3Br ,-PO (OC 2H 5) 2Br or-CN
2), side chain monomer H:
Figure C03160019D00062
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 5Be identical or different group, be selected from one of hydrogen atom, fluorine atom, phenyl ring, alkoxy C 1-C10, alkyl C1-C10:
Figure C03160019D00071
3), synthetic oligopolymer the phenylene ethylene oligopolymer (1) with two or more biphenyl center, (2), (3), (4) system for monomer A, B, C, D, E, F are obtained with side chain monomer H reaction respectively,
Figure C03160019D00072
Represent replacement situation on each end group phenyl ring with following formula: in the following formula, the replacement situation of the expression phenylene ethylene oligopolymer system (1) in the upper left corner, (3), (4); The replacement situation of its excess-three expression phenylene ethylene oligopolymer system (2);
Figure C03160019D00081
R 1, R 2, R 3, R 4, R 5, R 6Be identical or different group, be selected from: one of hydrogen atom, fluorine atom, phenyl ring, alkoxy C 1-C10, alkyl C1-C10 straight chain or branch chain;
R is identical group, is selected from: one of hydrogen atom, cyano group;
X, Y are identical or different atom, are selected from: one of O, S;
Z is selected from: one of C, Si.
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 (Knoevenagelcondensation) 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) Arno Kraft, Andrew C.Grimsdale, Andrew B.Holmes, Angew.Chem.Int.Ed.1998,37,402.]
1) the uncommon route of loving and respect one's elder brother Wei:
Nineteen fifty-three Germanization scholar Love and respect one's elder brother uncommon WeiFound 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, specifically react as follows:
Figure C03160019D00091
2) Wei Ti Xi-Huo Le 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 C03160019D00092
3) brain literary composition lattice 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.
Figure C03160019D00093
Making device, is luminescent layer with oligopolymer (1), (2), (3), (4) system, utilizes 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 selection of side chain monomer 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, then at room temperature to wherein dripping 3mL 5% ground alcohol sodium alcohol solution, react water cancellation reaction after 12 hours, repeated precipitation can obtain flaxen powder mass in methyl alcohol, is 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 the 3mL5% 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 3mL5% 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 the uncommon route of loving and respect one's elder brother Wei), 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 (4)

1, a kind of luminous oligopolymer of PPV class that contains the biphenyl center, it is characterized in that: it is obtained by center monomer and side chain monomer reaction, wherein:
1), the structure of center monomer is the polyfunctional group structure centre compd A with two or more biphenyl, B, C, D, E, F; Described compound is the conjugate ring with certain torsion resistance:
Figure C03160019C00021
In the following formula, M 1,, M 2,, M 3,, M 4Be selected from identical or different group :-PPh 3Br ,-PO (OC 2H 5) 2Br or-CN,
2), side chain monomer H:
Figure C03160019C00022
Among the described side chain monomer H, R 1, R 2, R 3, R 4, R 5Be identical or different group, be selected from one of hydrogen atom, fluorine atom, phenyl ring, alkoxy C 1-C10, alkyl C1-C10:
3), the synthetic oligopolymer is for reacting monomer A, B, C, D, E, F to the phenylene ethylene oligopolymer (1) with two or more biphenyl center, (2) system that obtains with side chain monomer H respectively:
Figure C03160019C00031
Represent replacement situation on each end group phenyl ring with following formula: in the following formula, the replacement situation of the expression phenylene ethylene oligopolymer system (1) in the upper left corner; The replacement situation of all the other expression phenylene ethylene oligopolymer systems (2);
Figure C03160019C00032
R is identical group, is selected from: one of hydrogen atom, cyano group;
R6 is C 6H 13
Z is selected from C.
2, the synthetic method that contains the luminous oligopolymer of PPV class at biphenyl center according to claim 1 is characterized in that:
Described 2), among the side chain monomer H, described side chain monomer H is following one of various:
Figure C03160019C00041
3, the synthetic method that contains the luminous oligopolymer of PPV class at biphenyl center according to claim 1 and 2 is characterized in that:
Described oligopolymer is the tetraphenyl ethylene base biphenyl TSB in oligopolymer (1) system, and its synthetic method is:
(1) by the uncommon route of loving and respect one's elder brother Wei:
4,, it is characterized in that with according to the luminous oligopolymer of claim 1 or the preparation of 2 described methods blue luminescent device as luminescent layer:
Described luminescent device comprises compound ITO layer, NPB layer, luminescent layer, Alq successively 3Layer, LiF layer, A1 layer, the material of described luminescent layer adopt TSB or the TBVB in described oligopolymer (1) or (2) system:
Figure C03160019C00043
CNB031600190A 2003-09-22 2003-09-22 PPV luminescence oligomer containing biphenyl center Expired - Fee Related CN100491313C (en)

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CN100340582C (en) * 2005-08-12 2007-10-03 复旦大学 Fluorophenyl-containing PPV and its uses
CN102249944B (en) * 2009-12-08 2013-10-16 四川大学 Compound containing staggered biphenyl center and preparation method thereof
CN102533277B (en) * 2011-12-15 2014-10-08 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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CN101717374B (en) * 2009-12-08 2011-12-14 四川大学 Compound comprising fork biphenyl center and preparation method thereof

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