CN104418856A - Octa-chloro-quaterrylenebisdicarboximide derivative, preparation method and application thereof - Google Patents
Octa-chloro-quaterrylenebisdicarboximide derivative, preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses an octa-chloro-quaterrylenebisdicarboximide derivative, a preparation method and an application thereof. With 1,6,7,12-tetrachloro-9,10-dibromoperylenebisimide as a raw material, the octa-chloro-quaterrylenebisdicarboximide derivative, represented as the following formula, is prepared through palladium as a catalyst in a one-steps coupling method through heating under protection of an inert gas. A product, after the reaction finished, is subjected to separation and purification to obtain the octa-chloro-quaterrylenebisdicarboximide derivative, which can be used as an organic n-type semiconductor electronic transport material in an organic electro-luminescence device, an organic thermal-chromic element, an organic field effect transistor an organic solar cell and the like.
Description
Technical field
The present invention relates to eight chlorine Quaterrylenebisdicarboximide derivatives and preparation method thereof and application.
Background technology
Rylenebisdicarboximide(comprises Naphthalenebisdiimide, Perylenebisdicarboximide, Terrylenebisdicarboximide, Quaterrylenebisdicarboximide) be the important organic functional molecular of a class; this is because this compounds has good chemical stability and excellent photoelectric characteristic; be widely used in functional materials; as as (J.Am.Chem.Soc. such as solar cell material, liquid crystal material, organic field-effect tube, luminescent materials; 2010; 132,3697 – 3699; J.Am.Chem.Soc., 2013,135,2338-2349; J.Am.Chem.Soc., 2012,134,5770 – 5773; Chem.Eur.J., 2007,13,6555 – 6561; Chem.Commun., 2012,48,9498 – 9500 etc.).But due to synthesis degree of difficulty increase along with the increase of conjugated degree, especially the application and development of Quaterrylenebisdicarboximide be seriously subject to its synthesis difficulty restriction.Therefore, obtain Quaterrylenebisdicarboximide derivative by simple synthetic method efficiently and there is important Research Significance and practical value.
Up to the present, a class report is only had to relate to Quaterrylenebisdicarboximide compounds: by closing the method synthesis Quaterrylenebisdicarboximide compounds (US5405962 of ring after first coupling, US5986099, but its synthesis step is more loaded down with trivial details US20060058330A1).Up to the present, eight chlorine Quaterrylenebisdicarboximide derivatives and simple preparation method efficiently thereof is not also seen.
Summary of the invention
The object of this invention is to provide a kind of eight chlorine Quaterrylenebisdicarboximide derivatives and preparation method thereof and application.
Eight chlorine Quaterrylenebisdicarboximide derivatives provided by the invention, its general structure such as formula shown in I,
In described formula I, R
1and R
2identical or different, be following group a or b:
A, be selected from the aryl of hydrogen, the alkyl of C1-30, the alkoxyl group of C1-30 and C5-30 any one;
B, containing substituent described group a; Described substituting group is selected from least one in halogen, the alkyl of C1-C30 and the alkoxyl group of C1-C30.
In group a described in compound shown in above-mentioned formula I, the aryl of C5-30 is phenyl, naphthyl, anthryl, phenanthryl, naphthacenyl, pentacenyl, hexacenyl, pyrenyl, indenyl, xenyl or fluorenyl;
The alkyl of described C1-30 be specially in C1-C24 alkyl, C18-C30 alkyl, C3-C24 alkyl, C3-C30 alkyl and C18-C24 alkyl any one;
The alkyl of described C1-30 is more specifically ethyl, propyl group, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, amyl group, hexyl, heptyl, octyl group, nonyl, decyl, hendecane base, 12 carbon alkyl, n-tridecane base, n-tetradecane base, pentadecane base, hexadecane base, heptadecane base, octadecyl, nonadecane base or petrosilane base;
The alkoxyl group of described C1-30 be methoxyl group, oxyethyl group, propoxy-, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert.-butoxy, pentyloxy, hexyloxy, heptan oxygen base, octyloxy, the ninth of the ten Heavenly Stems oxygen base, the last of the ten Heavenly stems oxygen base, hendecane oxygen base, 12 carbon alkoxyl groups, n-tridecane oxygen base, n-tetradecane oxygen base, pentadecane oxygen base, hexadecane oxygen base, heptadecane oxygen base, octodecane oxygen base, nonadecane oxygen base or petrosilane oxygen base;
More specifically, in described formula I, R
1and R
2all be selected from following group any one:
(being also the positive decyl tetradecyl of 2-),
(being also 2,6-diisopropyl phenyl),
(12-tricosyl) and--C
18h
37(being also Octadecane base).
Shown in preparation formula I provided by the invention, the method for compound, comprises the steps:
1,6,7,12-tetra-chloro-9,10-bis-bromine perylene diimide compounds, catalyzer and reductive agent shown in formula II are mixed the ullmann reaction carrying out palladium chtalyst in organic solvent, reacts complete and obtain compound shown in described formula I;
In described formula II, R
3definition and R
1definition identical.
In aforesaid method, described catalyzer is palladium catalyst, is specifically selected from least one in four triphenylphosphines conjunction palladiums, two triphenylphosphine palladium, palladium charcoal, palladium, Palladous nitrate, Palladous chloride and three (dibenzalacetone) two palladium;
Described reductive agent is selected from least one in hydrogen, hydrazine hydrate, oxammonium hydrochloride, iron powder, zinc powder, formic acid, formaldehyde, methyl alcohol and carbon monoxide;
Described organic solvent is selected from least one in N-Methyl pyrrolidone, dimethyl formamide, N,N-DIMETHYLACETAMIDE, methyl-sulphoxide, hexamethylphosphoramide, tetramethylene sulfone, acetonitrile and cyanobenzene.
Shown in described formula II, the molar ratio of 1,6,7,12-tetra-chloro-9,10-bis-bromine perylene diimide compounds, catalyzer and reductive agent is 1:0.001-0.2:2-20, is specially 1:0.1:5;
Shown in described organic solvent and described formula II, the amount ratio of 1,6,7,12-tetra-chloro-9,10-bis-bromine perylene diimide compounds is 20 ~ 30ml:1mmol.
In the ullmann reaction step of described palladium chtalyst, temperature is-50-150 DEG C, is specially 60 DEG C;
Time is 0.5-24 hour, is specially 4 hours.
The ullmann reaction of described palladium chtalyst carries out in an inert atmosphere;
Described inert atmosphere is specially nitrogen atmosphere.
In addition; using compound shown in formula I as compound shown in light absorbing material and/or the organic electroluminescence device of electron transport material, organic thermic look dependent element, organic field effect tube or organic solar batteries and formula I preparing the application in organic electroluminescence device, organic thermic look dependent element, organic field effect tube or organic solar batteries, also belong to protection scope of the present invention.Described electron transport material is specially n-type electron transport material.
The compound that the present invention obtains through nuclear magnetic resonance map (
1h-NMR), mass spectrum (MS) confirmation, structure is errorless.
Eight chlorine Quaterrylenebisdicarboximide derivatives provided by the invention can be used as n-type electron transport material and are applied to solar cell material, liquid crystal material, organic field-effect tube, luminous organic material, industrial dye etc.
The invention has the advantages that:
1, synthesis step is brief, and mild condition is easy and simple to handle.
2, to be raw materials usedly conveniently easy to get in synthesis, to be easy to suitability for industrialized production.
3, this analog derivative has good chemical stability.
4, this analog derivative is n-type electron transport material.
5, eight chlorine atoms on this compounds parent nucleus can derive modification further.
Accompanying drawing explanation
Fig. 1 is the N of embodiment 1, N '-two (the positive decyl tetradecyl of 2-) eight chlorine Quaterrylenebisdicarboximide derivatives
1h-NMR schemes.
Fig. 2 is the mass spectrum of the N of embodiment 1, N '-two (the positive decyl tetradecyl of 2-) eight chlorine Quaterrylenebisdicarboximide derivatives.
Fig. 3 is the mass spectrum of the eight chlorine Quaterrylenebisdicarboximide derivatives that the N of embodiment 2, N '-two (2,6-diisopropyl phenyl) replaces.
Fig. 4 is the N of embodiment 3, N '-two mass spectrum of eight chlorine Quaterrylenebisdicarboximide derivatives of replacing of Octadecane base.
Fig. 5 is the mass spectrum of the eight chlorine Quaterrylenebisdicarboximide derivatives that the N of embodiment 4, N '-two (12-tricosyl) replaces.
Fig. 6 is the concrete structure schematic diagram of embodiment 5 device.
Fig. 7 is the field-effect curve of output of embodiment 5 when thermal treatment temp 150 degrees Celsius.
Fig. 8 is the field-effect transition curve of embodiment 5 when thermal treatment temp 150 degrees Celsius.
Embodiment
Below in conjunction with specific embodiment, the present invention is further elaborated, but the present invention is not limited to following examples.Described method is ordinary method if no special instructions.Described starting material all can obtain from open commercial sources if no special instructions; 9,10-bis-bromine perylene diimides as chloro-in 1,6,7,12-4 synthesize by document (Org.Lett., 2012,14,5444 – 5447) report method.
Embodiment 4 12-bis-used tridecyl amine is according to document (J.Am.Chem.Soc., 2007,129,7234 – 7235) method be synthesized into, concrete grammar is as follows: by 4.3g(12.6mmol) 12-tricosanone, 10g (129mmol) ammonium acetate (NH
4and 0.56g (8.9mmol) sodium cyanoborohydride (NaBH OAc),
3cN) stirring at room temperature is dissolved in 38ml hplc grade methanol 56 hours, add 250ml water after the cancellation of reaction 2ml concentrated hydrochloric acid, be adjusted to pH=10 with potassium hydroxide, then use 150ml chloroform extraction twice, evaporate to dryness chloroform obtains the thick product of 12-bis-tridecyl amine, is directly used in subsequent reactions.
N, N '-two shown in embodiment 1, formula Ia (the positive decyl tetradecyl of 2-) eight chlorine Quaterrylenebisdicarboximide derivatives
Under nitrogen protection, to 950mg(1mmol is housed) N-(the positive decyl tetradecyl of 2-)-1 shown in formula IIa, 6, 7, 12-tetra-chloro-9, 91mg(0.1mmol is added in the reaction flask of 10-bis-Xiu perylene diimide) palladium catalyst three (dibenzalacetone) two palladium and 325mg(5mmol) after reductive agent zinc powder, inject 20ml anhydrous dimethyl formamide (DMF), 60 DEG C of stirrings carried out the ullmann reaction of palladium chtalyst after 4 hours, product cooling is poured into water filtration and obtains green thick product, thick product obtains green powder product 389mg through silica gel column chromatography separating-purifying, productive rate is 49%.
The structure confirmation data of this product is as follows:
1H NMR(C
6D
6,400MHz,298K):δ8.75(s,4H),7.78(s,4H),4.39(d,4H),2.41(s,2H),1.70–1.30(m,80H),0.96–0.90(m,12H).
13C NMR(CDCl
3,100MHz,298K):δ=162.88,136.01,133.84,132.97,132.12,129.40,129.23,125.28,124.96,123.31,122.40,45.22,36.87,32.09,31.85,30.21,29.89,29.84,29.53,26.64,26.59,22.86,22.84,14.29,14.27.
MS(MALDI-TOF):m/z(M+)=1586.7(calcd for C
92H
106Cl
8N
2O
4:1586.6).
N, N '-two (the positive decyl tetradecyl of 2-) eight chlorine Quaterrylenebisdicarboximide derivatives
1h-NMR figure as shown in Figure 1; Mass spectrum as shown in Figure 2.
As from the foregoing, this product structure is correct, is compound N shown in the formula Ia of ownership formula I, N '-two (the positive decyl tetradecyl of 2-) eight chlorine Quaterrylenebisdicarboximide derivatives.
The eight chlorine Quaterrylenebisdicarboximide derivatives that N, N '-two shown in embodiment 2, formula Ib (2,6-diisopropyl phenyl) replace
Under nitrogen protection, to 780mg(1mmol is housed) compound N-2 shown in formula IIb, 6-diisopropyl phenyl-1, 6, 7, 12-tetra-chloro-9, 91mg(0.1mmol is added in the reaction flask of 10-bis-Xiu perylene diimide) palladium catalyst three (dibenzalacetone) two palladium and 325mg(5mmol) after reductive agent zinc powder, inject 20ml anhydrous dimethyl formamide (DMF), 60 DEG C of stirrings carried out the ullmann reaction of palladium chtalyst after 4 hours, product cooling is poured into water filtration and obtains green thick product, thick product obtains the 154mg of green powder through silica gel column chromatography separating-purifying, productive rate is 25%.
The structure confirmation data of this product is as follows:
MS (MALDI-TOF): m/z (M
+)=1234.2 (calcd for C
68h
42cl
8n
2o
4: 1234.1), mass spectrum is as shown in Figure 3.
As from the foregoing, this product structure is correct, is compound N shown in the formula Ib of ownership formula I, N '-two (2,6-diisopropyl phenyl) eight chlorine Quaterrylenebisdicarboximide derivative.
The eight chlorine Quaterrylenebisdicarboximide derivatives that the Octadecane of N, N '-two shown in embodiment 3, formula Ic base replaces
Under nitrogen protection; to 870mg(1mmol is housed) compound N-Octadecane base-1 shown in formula IIc; 6; 7; 12-tetra-chloro-9; 91mg(0.1mmol is added in the reaction flask of 10-bis-Xiu perylene diimide) three (dibenzalacetone) two palladium and 325mg(5mmol) after zinc powder; inject 20ml anhydrous dimethyl formamide (DMF); 60 DEG C of ullmann reactions carrying out palladium chtalyst are after 4 hours; product cooling is poured into water filtration and obtains green thick product; thick product obtains green powder product 247mg through silica gel column chromatography separating-purifying, and productive rate is 34%.
The structure confirmation data of this product is as follows:
MS (MALDI-TOF): m/z (M
+)=1416.4 (calcd for C
80h
82cl
8n
2o
4: 1416.7), mass spectrum is as shown in Figure 4.
As from the foregoing, this product structure is correct, is compound N shown in the formula Ic of ownership formula I, N '-two Octadecane base eight chlorine Quaterrylenebisdicarboximide derivative.
The eight chlorine Quaterrylenebisdicarboximide derivatives that N, N '-two shown in embodiment 4, formula Id (12-tricosyl) replace
Under nitrogen protection; to 940mg(1mmol is housed) compound N-12-tricosyl-1 shown in formula IId; 6; 7; 12-tetra-chloro-9; 91mg(0.1mmol is added in the reaction flask of 10-bis-Xiu perylene diimide) three (dibenzalacetone) two palladium and 325mg(5mmol) after zinc powder; inject 20ml anhydrous dimethyl formamide (DMF); 60 DEG C of stirrings carried out the ullmann reaction of palladium chtalyst after 4 hours; product cooling is poured into water filtration and obtains green thick product; thick product obtains green powder product 172mg through silica gel column chromatography separating-purifying, and productive rate is 22%.
The structure confirmation data of this product is as follows:
MS (MALDI-TOF): m/z (M
+)=1558.5 (calcd for C
90h
102c
l8n
2o
4: 1558.5), mass spectrum is as shown in Figure 5.
As from the foregoing, this product structure is correct, is compound N shown in the formula Id of ownership formula I, the eight chlorine Quaterrylenebisdicarboximide derivatives that N '-two (12-tricosyl) replaces.
Embodiment 5, compound shown in embodiment 1 gained formula Ia is utilized to prepare organic field effect tube device
The structure of this device is bottom gate-top contact, and this device is made up of grid layer, insulation layer, active coating, source electrode and drain electrode;
As shown in Figure 6, insulation layer 4 is positioned on grid layer 5 particular location relation between device layers, and active coating 3 is positioned on insulation layer 4, and source electrode 1 and drain electrode 2 are positioned at same layer, and are all positioned on active coating 3;
Grid layer to be thickness the be Si of 400 μm;
Insulation layer is the thickness that OTS modifies is the SiO of 300nm
2in/Si substrate;
Active coating is compound shown in embodiment 1 gained formula Ia, thickness is 60nm, its preparation method is spin-coating method, be specially compound N shown in formula Ia, N '-two (the positive decyl tetradecyl of 2-) eight chlorine Quaterrylenebisdicarboximide derivatives are dissolved in chloroform, concentration is 10mg/mL, adopts spin-coating method to be coated in OTS(octadecyltrichlorosilane) thickness modified is the SiO of 300nm
2in/Si substrate;
The thickness that source-drain electrode is evaporation and obtains is the Au layer of 25nm.
Under different thermal treatment temps, measure the field-effect mobility of this device, test result is as shown in table 1:
The field-effect mobility of device at table 1, different heat treatment temperature
| Thermal treatment temp/DEG C | Mobility [mu]/cm 2·V -1·s -1 | Threshold voltage V T/V |
| 25 | 2.14×10 -3 | 23.1 |
| 100 | 2.06×10 -3 | 16.0 |
| 150 | 1.51×10 -2 | 20.2 |
| 200 | 9.87×10 -3 | 25.0 |
| 250 | 8.77×10 -3 | 10.8 |
As shown in Figure 6, field-effect transition curve as shown in Figure 7 for field-effect curve of output during thermal treatment temp 150 DEG C.
As from the foregoing, the mobility of device reaches optimum value 1.51 × 10 when thermal treatment temp 150 degrees Celsius
-2μ/cm
2v
-1s
-1.
When compound shown in embodiment 2-4 gained formula I is used as organic field effect tube device, obtained device performance and upper without substantive difference, repeats no more.
Claims (10)
1. compound shown in formula I,
In described formula I, R
1and R
2identical or different, be following group a or b:
A, be selected from the aryl of hydrogen, the alkyl of C1-30, the alkoxyl group of C1-30 and C5-30 any one;
B, containing substituent described group a; Described substituting group is selected from least one in halogen, the alkyl of C1-C30 and the alkoxyl group of C1-C30.
2. compound according to claim 1, is characterized in that: in described group a, and the aryl of C5-30 is phenyl, naphthyl, anthryl, phenanthryl, naphthacenyl, pentacenyl, hexacenyl, pyrenyl, indenyl, xenyl or fluorenyl;
The alkyl of described C1-30 is ethyl, propyl group, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, amyl group, hexyl, heptyl, octyl group, nonyl, decyl, hendecane base, 12 carbon alkyl, n-tridecane base, n-tetradecane base, pentadecane base, hexadecane base, heptadecane base, octadecyl, nonadecane base or petrosilane base;
The alkoxyl group of described C1-30 be methoxyl group, oxyethyl group, propoxy-, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert.-butoxy, pentyloxy, hexyloxy, heptan oxygen base, octyloxy, the ninth of the ten Heavenly Stems oxygen base, the last of the ten Heavenly stems oxygen base, hendecane oxygen base, 12 carbon alkoxyl groups, n-tridecane oxygen base, n-tetradecane oxygen base, pentadecane oxygen base, hexadecane oxygen base, heptadecane oxygen base, octodecane oxygen base, nonadecane oxygen base or petrosilane oxygen base.
3. compound according to claim 1 and 2, is characterized in that: in described formula I, R
1and R
2all be selected from the positive decyl tetradecyl of 2-, 2,6-diisopropyl phenyls, 12-tricosyl and Octadecane base any one.
4. prepare a method for compound shown in the arbitrary described formula I of claim 1-3, comprise the steps:
1,6,7,12-tetra-chloro-9,10-bis-bromine perylene diimide compounds, catalyzer and reductive agent shown in formula II are mixed the ullmann reaction carrying out palladium chtalyst in organic solvent, reacts complete and obtain compound shown in described formula I;
In described formula II, R
3definition and claim 1 in R
1definition identical.
5. method according to claim 4, it is characterized in that: described catalyzer is palladium catalyst, be specifically selected from least one in four triphenylphosphines conjunction palladiums, two triphenylphosphine palladium, palladium charcoal, palladium, Palladous nitrate, Palladous chloride and three (dibenzalacetone) two palladium;
Described reductive agent is selected from least one in hydrogen, hydrazine hydrate, oxammonium hydrochloride, iron powder, zinc powder, formic acid, formaldehyde, methyl alcohol and carbon monoxide;
Described organic solvent is selected from least one in N-Methyl pyrrolidone, DMF, N,N-dimethylacetamide, dimethyl sulfoxide (DMSO), hexamethylphosphoramide, tetramethylene sulfone, acetonitrile and cyanobenzene.
6. the method according to claim 4 or 5, is characterized in that: shown in described formula II, the molar ratio of 1,6,7,12-tetra-chloro-9,10-bis-bromine perylene diimide compounds, catalyzer and reductive agent is 1:0.001-0.2:2-20, is specially 1:0.1:5;
Shown in described organic solvent and described formula II, the amount ratio of 1,6,7,12-tetra-chloro-9,10-bis-bromine perylene diimide compounds is 20 ~ 30ml:1mmol.
7., according to the arbitrary described method of claim 4-6, it is characterized in that: in the ullmann reaction step of described palladium chtalyst, temperature is-50-150 DEG C, is specially 60 DEG C;
Time is 0.5-24 hour, is specially 4 hours.
8., according to the arbitrary described method of claim 4-7, it is characterized in that: the ullmann reaction of described palladium chtalyst carries out in an inert atmosphere;
Described inert atmosphere is nitrogen.
9. using compound shown in the arbitrary described formula I of claim 1-3 as light absorbing material and/or the organic electroluminescence device of electron transport material, organic thermic look dependent element, organic field effect tube or organic solar batteries.
10. compound shown in the arbitrary described formula I of claim 1-3 is preparing the application in organic electroluminescence device, organic thermic look dependent element, organic field effect tube or organic solar batteries.
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| CN104603112A (en) * | 2012-08-30 | 2015-05-06 | 巴斯夫欧洲公司 | Double donor functionalisation of the peri-positions of perylene and naphthalene monoimide via versatile building blocks |
| EP3816238A1 (en) | 2019-11-04 | 2021-05-05 | Textilchemie Dr. Petry Gmbh | Polyparaperylene derivatives and methods for making same |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104603112A (en) * | 2012-08-30 | 2015-05-06 | 巴斯夫欧洲公司 | Double donor functionalisation of the peri-positions of perylene and naphthalene monoimide via versatile building blocks |
| US9630973B2 (en) | 2012-08-30 | 2017-04-25 | Basf Se | Double donor functionalisation of the peri-positions of perylene and naphthalene monoimide via versatile building blocks |
| CN104603112B (en) * | 2012-08-30 | 2017-06-16 | 巴斯夫欧洲公司 | Via the double donor Guan Nengization perylenes of multifunction structure unit and the imido peri-position of naphthalene list |
| EP3816238A1 (en) | 2019-11-04 | 2021-05-05 | Textilchemie Dr. Petry Gmbh | Polyparaperylene derivatives and methods for making same |
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