CN109762006A - A kind of star-like non-fullerene small organic molecule acceptor material and preparation method thereof containing pyrene and imidodicarbonic diamide - Google Patents
A kind of star-like non-fullerene small organic molecule acceptor material and preparation method thereof containing pyrene and imidodicarbonic diamide Download PDFInfo
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Abstract
The invention discloses a kind of star-like non-fullerene small organic molecule acceptor material and preparation method thereof containing pyrene and imidodicarbonic diamide.Non- fullerene small organic molecule acceptor material has good thermal stability by three key bridging condensed ring pyrenes and acid imide unit, resulting materials, and raw material are commonly easy to get, can be by recrystallization purifying, and production cost is low.It is applied in polymer solar battery, it can get the effect of energy conversion efficiency 6~8% under conditions of optimised devices, it is added in ternary solar battery active layer as third component, its short-circuit current density can be dramatically increased, it can get the effect of energy conversion efficiency 8%~11%, there is certain practical application value.
Description
Technical field
The present invention relates to for the non-fullerene small organic molecule acceptor material of polymer solar battery and its preparation side
Method, and in particular to a kind of star-like non-fullerene small organic molecule acceptor material containing pyrene and imidodicarbonic diamide and its preparation side
Method.
Background technique
Conventional fossil fuel is non-renewable, and economic development surges to energy demand, the change of energy consumption structure, fossil combustion
Expect immoderate exploitation and utilize, results in the energy crisis broken out several times in world wide, the living environment of the mankind is brought
Unprecedented pressure and challenge.For the energy problem got worse, Novel clean renewable energy is researched and developed (too
Positive energy, wind energy, tide energy etc.) have become the major subjects that the mankind face at present.Solar energy as most abundant, the clean energy it
One, cause the concern of extensive researcher.The utilization of solar energy is concentrated mainly on the solar battery of design different configuration at present
The storage and conversion of energy are carried out, wherein organic polymer solar cell technology has swift and violent development.Too for polymer
Traditional fullerene acceptor material purifying difficulty, absorption spectrum ranges are narrow, compatible with organic polymer donor material in positive energy battery
Property it is bad the deficiencies of, non-fullerene small organic molecule acceptor material is a dark horse, and achieves proud progress recent years.
Chinese patent ZL201610765785.0 disclose a kind of non-fullerene solar battery based on multi-fused rings class by
Body material, is used in polymer solar battery, obtains 6.35% energy conversion efficiency.Chinese patent
ZL201710878172.2 discloses a kind of star-like non-fullerene small molecule receptor material of broad-band gap, is used for the polymer sun
In energy battery, energy conversion efficiency has reached 10.14%.They are equal to the incident photon-to-electron conversion efficiency for improving polymer solar battery
With positive directive significance.The exploitation of non-fullerene small organic molecule acceptor material compensates for the polymerization that fullerene is receptor
The critical defect that object solar battery is shown, however, the design and research of non-fullerene small molecule receptor be still faced with it is huge
Challenge: the electron mobility of 1. most of non-fullerene small molecule receptors be lower than typical fullerene acceptor material；2. many
It is a huge work that how known high-efficiency polymer donor material and non-fullerene small molecule receptor, which reasonably match, optimize,
Journey；3. the separation of charge of non-fullerene polymer solar battery, recombination mechanism may be different from traditional fullerene device, still
Wait explore.Novel non-fullerene small molecule receptor material is actively found and develops, to the practical application of polymer solar battery
It is of great significance.
Summary of the invention
The purpose of the present invention is to provide a kind of star-like non-fullerene small organic molecule containing pyrene and imidodicarbonic diamide by
Body material and preparation method thereof.The small molecule have wider absorption spectrum and with high-efficiency polymer donor material PTB7-Th,
The absorption spectrums such as PBDB-T are complementary.Pyrene and imidodicarbonic diamide class materials synthesis are at low cost, can largely be given birth to by recrystallization process
It produces, is had been widely used in pigmenting techniques based on imidodicarbonic diamide sill, before reflecting that this kind of material has good business
Scape.
The technical solution of the present invention is as follows:
A kind of star-like non-fullerene small organic molecule acceptor material containing pyrene and imidodicarbonic diamide, structural formula such as formula (I)
It is shown:
In formula (I), R is C1-C8Alkyl chain.
The preparation method of the above-mentioned star-like non-fullerene small organic molecule acceptor material containing pyrene and imidodicarbonic diamide, packet
Include following steps:
(1) 1,3,6,8- tetrabromo pyrene compounds and trimethylsilyl acetylene compound carry out coupling reaction, obtain intermediate chemical combination
Object a,
The structural formula of the 1,3,6,8- tetrabromo pyrene compound is
The structural formula of the trimethylsilyl acetylene compound is
The structural formula of the intermediate compound a is
(2) using tetrahydrofuran as solvent, intermediate compound a carries out desilication reaction under the action of potassium hydroxide, obtains
Between compound b,
The intermediate compound b structural formula is
(3) intermediate compound b and compound PDI-Br carries out Sonogashira coupling reaction, obtains shown in formula (I) eventually
Product；
The structural formula of the compound PDI-Br is
Wherein, R is C1-C8Alkyl.
Preferably, step (1) specifically: by 1,3,6,8- tetrabromo pyrene, trimethylsilyl acetylene compound, two (triphenylphosphines)
Palladium chloride and triphenylphosphine are mixed by the molar ratio of 1-10:6-60:0.2-2:0.2-2, and cuprous iodide is added, and are added after mixing
Enter in toluene solution, N270~90 DEG C of reactions 24-34 hours are heated under protection；It is cooled to room temperature, uses CH2Cl2It is extracted with water,
Anhydrous MgSO4It dries, filters, solvent is spin-dried for；It finally uses petroleum ether to carry out column chromatography as eluent, obtains orange-yellow solid
Body, as intermediate compound a.
Preferably, toluene solution and 1, the amount ratio of 3,6,8- tetrabromo pyrenes are 50~100ml:1-10mmol.
Preferably, step (2) specifically: intermediate compound a and potassium hydroxide are mixed by the molar ratio of 1-10:8-80,
And THF is added, it is added in reactor, N2Protection, which is placed under room temperature, stirs 12 hours or more, and end of reaction is poured into water
Middle sedimentation filters, obtains faint yellow solid particle, as intermediate compound b.
Preferably, step (3) specifically: by the resulting intermediate compound b of step (2), compound PDI-Br, four triphenyls
Phosphine palladium and diisopropylamine are mixed by 0.05-0.2mmol:0.3-1.2mmol:80~120mg:1~3ml amount ratio, and are added
Then they and toluene are added in eggplant shaped reaction device, N by cuprous iodide jointly2Protection is back flow reaction 30-48 hours lower；Stop
Only react, it is cooling, it is extracted with chloroform and water, anhydrous MgSO4It dries, filters, is spin-dried for solvent；Finally using chloroform as
Eluent carries out column chromatography, obtains black solid, as final product (I).
Preferably, the amount ratio of toluene and compound PDI-Br are 20-40mL:0.3-1.2mmol.
The beneficial effects of the present invention are:
(1) the star-like small molecule receptor of imidodicarbonic diamide class: firstly, passing through triple carbon-carbon bonds for electron unit and electrophilic list
Member connection, extends the conjugated system of the small molecule well, enhances Intramolecular electron transfer effect, is added significantly to be conjugated
System electronic cloud density；Secondly, hub-and-spoke configuration can effectively inhibit the trend of imidodicarbonic diamide micromolecular receptor clustering, really
Protect its with polymeric donor is good that pattern is blended.Therefore, based on the star-like small molecule of imidodicarbonic diamide class of this three keys bridging
Receptor has wider absorption spectrum, it is blended with polymeric donor and prepares solar battery by excellent charge transport properties
Higher short-circuit current density and good fill factor can be obtained.
(2) non-fullerene small organic molecule acceptor material of the invention is applied not only to binary polymer solar battery,
The effect that can get energy conversion efficiency 6~8% under conditions of optimised devices, classical height is added to as third component
It imitates in active layer, the ternary organic polymer solar cell of preparation can dramatically increase its short-circuit current density, can get energy
The effect of transfer efficiency 8%~11% is measured, there is certain practical application value.
(3) small molecule receptor material of the invention, thermal stability is good, and raw material are commonly easy to get, can be real by recrystallization
It now purifies, production cost significantly reduces.
Detailed description of the invention
Fig. 1 is the J- of binary and ternary organic solar batteries prepared by the B-4TPDI acceptor molecule of the preparation of embodiment 1
V curve graph.
Specific embodiment
The present invention will be further described combined with specific embodiments below, but the present invention is not limited thereto.
Embodiment 1
The non-fullerene small organic molecule acceptor material that a kind of chemical structural formula is B-4TPDI, synthetic route are as follows:
(1) chemical structural formula is the synthesis of the intermediate of a:
By (517mg, 1mmol) 1,3,6,8- tetrabromo pyrenes, (588mg, 6mmol) trimethylsilyl acetylene compound, (140mg,
0.2mmol) two (triphenylphosphine) palladium chloride, (52mg, 0.2mmol) triphenylphosphine, suitable cuprous iodide, mixing are added
In 50mL toluene solution, N280 DEG C are heated under protection to react 24 hours；It is cooled to room temperature, uses CH2Cl2It is extracted with water, it is anhydrous
MgSO4It dries, filters, solvent is spin-dried for；It finally uses petroleum ether to carry out column chromatography as eluent, obtains orange/yellow solid, i.e.,
For intermediate compound a, yield 90%.1H NMR(400MHz,CDCl3, δ/ppm): 8.57 (s, 4H), 8.26 (s, 2H), 0.38
(s, 36H)
(2) chemical structural formula is the synthesis of the intermediate of b:
By (587mg, 1mmol) intermediate compound a, (448mg, 8mmol) potassium hydroxide, 50mLTHF is added to reaction flask
In, N2Protection, which is placed under room temperature, to be stirred overnight, and end of reaction is poured into 500mL water and settles, and is filtered, is obtained faint yellow
Solid particle, as intermediate compound b, yield 97%.1H NMR(400MHz,CDCl3, δ/ppm): 8.67 (s, 4H), 8.37
(s, 2H), 3.65 (s, 4H).
(3) chemical structural formula is the synthesis of the non-fullerene small organic molecule acceptor material of B-4TPDI:
By the resulting intermediate compound b (29.8mg, 0.1mmol) of step (2), PDI-Br compound (418mg,
0.6mmol), the tetra-triphenylphosphine palladium of 100mg, 2mL diisopropylamine, suitable cuprous iodide, the toluene of 20mL are added to eggplant shape
In reaction flask, N2It protects back flow reaction 48 hours lower；Stop reaction, it is cooling, it is extracted with chloroform and water, anhydrous MgSO4It is dry
Dry, filtering is spin-dried for solvent；Column chromatography is finally carried out using chloroform as eluent, obtains black solid, as small point of receptor
Sub- B-4TPDI, yield 75%.1H NMR(400MHz,CDCl3, δ/ppm): 10.49 (m, 4H), 8.75 (m, 30H), 5.02-
5.23 (m, 8H), 1.88-2.29 (m, 32H), 0.65-1.34 (m, 144H)13C NMR(100MHz,CDCl3,δ/ppm):
163.19,137.64,134.09,132.44,131.25,128.97,127.72,123.43,119.13,54.89,54.41,
32.28,31.76,31.57,29.72,26.67,26.52,22.57,22.44,14.03,13.88.MS(MALDI-TOF,m/
z):[M+Na+]calcd for C208H218N8O16Na+1,3107.07,
found,3107.67.
Embodiment 2
The preparation of binary solar battery based on non-fullerene small organic molecule B-4TPDI acceptor material and its photovoltaic
It can test:
The ITO electro-conductive glass purchased is cleaned first: according to this with cleaning solution, ultrapure water, acetone, ethyl alcohol, isopropanol
Each ultrasonic cleaning 15 to 30 minutes, it is then 10 minutes dry in 100 DEG C of drying oven, it takes out, after cooling at UV ozone
Reason 15 minutes spare.Then it configures ZnO precursor solution: weighing a certain amount of two water zinc acetate and ethanol amine, be dissolved in 2- methoxyl group
In ethyl alcohol, obtaining two water zinc acetate concentrations is 0.75mol L-1, ethanolamine concentration is 0.75mol L-1Solution, then by it
It is placed in glove box stirring at normal temperature 8 hours or more, it is spare.The ITO electro-conductive glass handled well before is put into water oxygen index to be less than
In the glove box of 1PPM, spin coating ZnO precursor solution takes out, makes annealing treatment 30 minutes under the conditions of 220 DEG C in atmospheric environment,
The ITO electrode (ZnO is with a thickness of 30nm) of ZnO modification is obtained, glove box is put into.It is respectively that ready 2 kinds of blendings active layer is molten
Liquid is spin-coated on ZnO electron transfer layer.2 kinds of active layer solution are respectively: (1) polymeric donor PTB7-Th and non-fullerene have
The blend solution (concentration 20mg/mL) of machine small molecule receptor B-4TPDI (mass ratio 1:1.5), and percent by volume is added
For 3% chloronaphthalene as additive；(2) polymeric donor PBDB-T and non-fullerene small organic molecule receptor B-4TPDI (quality
Than the blend solution (concentration 20mg/mL) for 1.5:1), and the chloronaphthalene that percent by volume is 3% is added as additive；?
Less than 1.5 × 10-4The MoO of upper 5.0nm is deposited under Pa pressure according to this3Anode buffer layer and 100nm Al anode top electrode.Finally
It is 100mW/cm in light intensity-2Simulated solar light source under to device carry out photovoltaic performance test.
The molecular structural formula of polymeric donor PTB7-Th used in the present invention is as follows:
The molecular structural formula of polymeric donor PBDB-T used in the present invention is as follows:
Binary solar battery based on PTB7-Th:B-4TPDI active layer, test results are shown in figure 1: open-circuit voltage
For 0.78V, short-circuit current density is 18.13mA cm-2, fill factor 54.58%, energy conversion efficiency 7.71%.
Based on the solar battery of PBDB-T:B-4TPDI active layer, test results are shown in figure 1: open-circuit voltage is
0.86V, short-circuit current density are 13.15mA cm-2, fill factor 60.42%, energy conversion efficiency 6.84%.
Embodiment 3
The preparation of ternary solar battery based on non-fullerene small organic molecule B-4TPDI acceptor material and its photovoltaic
It can test:
The process and method of the preparation of solar battery and its photovoltaic performance test only difference is that, incite somebody to action with embodiment 2
Active layer is changed to: (1) polymeric donor PTB7-Th and 2 kinds of non-fullerene small organic molecule receptor B-4TPDI, ITIC (mass ratioes
For the blend solution (concentration 20mg/mL) of 0.66:0.05:0.95)；(2) polymeric donor PBDB-T and 2 kinds of non-fullerenes have
The blend solution (concentration 20mg/mL) of machine small molecule receptor B-4TPDI, ITIC (mass ratio 1:0.05:0.95), and be added
The 1,8- diiodo-octane that percent by volume is 0.5% is as additive.
The molecular structural formula of another small molecule receptor ITIC used in the present invention is as follows:
Based on the solar battery of PTB7-Th:ITIC:B-4TPDI active layer, test results are shown in figure 1: open-circuit voltage
For 0.79V, short-circuit current density is 18.18mA cm-2, fill factor 60.32%, energy conversion efficiency 8.76%.
Based on the solar battery of PBDB-T:ITIC:B-4TPDI active layer, test results are shown in figure 1: open-circuit voltage
For 0.88V, short-circuit current density is 18.50mA cm-2, fill factor 66.64%, energy conversion efficiency 10.93%.
Claims (7)
1. a kind of star-like non-fullerene small organic molecule acceptor material containing pyrene and imidodicarbonic diamide, which is characterized in that have
Structure shown in formula (I):
In formula (I), R is C1-C8Alkyl chain.
2. the preparation of the star-like non-fullerene small organic molecule acceptor material described in claim 1 containing pyrene and imidodicarbonic diamide
Method, which comprises the steps of:
(1) 1,3,6,8- tetrabromo pyrene compounds and trimethylsilyl acetylene compound carry out coupling reaction, obtain intermediate compound a:
The structural formula of the 1,3,6,8- tetrabromo pyrene compound is
The structural formula of the trimethylsilyl acetylene compound is
The structural formula of the intermediate compound a is
(2) using tetrahydrofuran as solvent, intermediate compound a carries out desilication reaction under the action of potassium hydroxide, obtains intermediateization
Close object b:
The structural formula of the intermediate compound b is
(3) intermediate compound b and compound PDI-Br carries out Sonogashira coupling reaction, obtains producing eventually shown in formula (I)
Object:
The structural formula of the compound PDI-Br is
Wherein, R is C1-C8Alkyl.
3. the star-like non-fullerene small organic molecule acceptor material according to claim 2 containing pyrene and imidodicarbonic diamide
Preparation method, which is characterized in that step (1) specifically:
By 1,3,6,8- tetrabromo pyrene, trimethylsilyl acetylene compound, two (triphenylphosphine) palladium chlorides and triphenylphosphine by 1~
The mixing of 10:6~60:0.2~2:0.2~2 molar ratio, and cuprous iodide is added, it is added in toluene solution after mixing, N2Protection
Under be heated to 70~90 DEG C react 24~34 hours；It is cooled to room temperature, uses CH2Cl2It is extracted with water, anhydrous MgSO4It dries, filters,
Solvent is spin-dried for；It finally uses petroleum ether to carry out column chromatography as eluent, obtains orange/yellow solid, as intermediate compound a.
4. the star-like non-fullerene small organic molecule acceptor material according to claim 3 containing pyrene and imidodicarbonic diamide
Preparation method, which is characterized in that toluene solution and 1, the amount ratio of 3,6,8- tetrabromo pyrenes are 50~100ml:1-10mmol.
5. the star-like non-fullerene small organic molecule acceptor material according to claim 2 containing pyrene and imidodicarbonic diamide
Preparation method, which is characterized in that step (2) specifically: intermediate compound a and potassium hydroxide are pressed to the molar ratio of 1-10:8-80
Mixing, and THF is added, it is added in reactor, N2Protection, which is placed under room temperature, stirs 12 hours or more, end of reaction, by it
It is poured into water sedimentation, filters, obtains faint yellow solid particle, as intermediate compound b.
6. the star-like non-fullerene small organic molecule acceptor material according to claim 2 containing pyrene and imidodicarbonic diamide
Preparation method, which is characterized in that step (3) specifically: by the resulting intermediate compound b of step (2), compound PDI-Br, four
Triphenylphosphine palladium and diisopropylamine are mixed by 0.05-0.2mmol:0.3-1.2mmol:80~120mg:1~3ml amount ratio,
Cuprous iodide is added, then they and toluene are added to jointly in eggplant shaped reaction device, N2Protect lower back flow reaction 30-48 small
When；Stop reaction, it is cooling, it is extracted with chloroform and water, anhydrous MgSO4It dries, filters, is spin-dried for solvent；Finally with three chloromethanes
Alkane carries out column chromatography as eluent, obtains black solid, as final product (I).
7. the star-like non-fullerene small organic molecule acceptor material according to claim 6 containing pyrene and imidodicarbonic diamide
Preparation method, which is characterized in that the amount ratio of toluene and compound PDI-Br are 20-40mL:0.3-1.2mmol.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110931644A (en) * | 2019-12-10 | 2020-03-27 | 东华大学 | Ternary organic solar cell and preparation method thereof |
| CN113045590A (en) * | 2021-04-01 | 2021-06-29 | 四川大学 | Perylene diimide non-fullerene acceptor material and application thereof |
| CN115043856A (en) * | 2022-07-13 | 2022-09-13 | 陕西师范大学 | Pyrene fused ring nucleus type non-fullerene organic small molecule receptor material and preparation method and application thereof |
-
2019
- 2019-01-09 CN CN201910021278.XA patent/CN109762006A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110931644A (en) * | 2019-12-10 | 2020-03-27 | 东华大学 | Ternary organic solar cell and preparation method thereof |
| CN110931644B (en) * | 2019-12-10 | 2021-07-20 | 东华大学 | Ternary organic solar cell and preparation method thereof |
| CN113045590A (en) * | 2021-04-01 | 2021-06-29 | 四川大学 | Perylene diimide non-fullerene acceptor material and application thereof |
| CN115043856A (en) * | 2022-07-13 | 2022-09-13 | 陕西师范大学 | Pyrene fused ring nucleus type non-fullerene organic small molecule receptor material and preparation method and application thereof |
| CN115043856B (en) * | 2022-07-13 | 2023-07-04 | 陕西师范大学 | Pyrene condensed ring nucleus non-fullerene organic small molecule receptor material and preparation method and application thereof |
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Application publication date: 20190517 |