CN115785119B - Organic compound and application thereof in organic electronic device - Google Patents
Organic compound and application thereof in organic electronic device Download PDFInfo
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Abstract
The present application relates to an organic compound and its use in organic electronic devices. The organic compound is based on an A-pi-D-pi-A structure, the donor unit D has a larger conjugated system and plane symmetry and excellent charge transmission performance, the acceptor unit A can provide better photovoltaic performance, and the absorption, energy level and band gap of the compound can be regulated and controlled, so that the compound has a proper energy level. The organic compound provided by the application is applied to an organic solar cell device as a small molecular donor material, and can improve the photoelectric conversion efficiency of the device.
Description
Technical Field
The application relates to the field of organic device materials, in particular to an organic compound and application thereof in an organic electronic device.
Background
Organic solar cells (OPVs) are receiving global attention due to their low cost, light weight, simple manufacturing process, and flexible manufacturing over large areas. Organic solar cells in which the active layer has a polymer as an electron donor are conventionally referred to as polymer solar cells; organic solar cells having small molecules as electron donors are known as small molecule solar cells. Compared with polymers, the small molecular material has the advantages of adjustable energy level, simple synthesis, low processing cost, easy purification and the like, thereby avoiding the defect that the reproducibility of the device results cannot be ensured due to different synthesis batches. Thus, small molecule organic solar cells have received increasing attention in recent years.
Organic Photovoltaic (OPV) cells generally consist of five parts: anode, anode buffer layer, active layer, cathode buffer and cathode. Wherein the active layer generally comprises a donor material and a acceptor material. The working principle is as follows: when sunlight is incident on the active layer through the transparent substrate and the electrode, photons having energies greater than the band gap energy are absorbed by the acceptor material, and electrons are excited to transition from the Highest Occupied Molecular Orbital (HOMO) to the Lowest Unoccupied Molecular Orbital (LUMO), while corresponding holes are generated at the HOMO. Since the relative dielectric constant of the organic material is small, electrons and holes exist in an exciton state of a bound state. Then, the exciton diffuses to the interface of the donor and acceptor, and the exciton is dissociated under the drive of energy level difference, so that the charge separation is realized. Subsequently, under the action of the built-in electric field, free holes and electrons are transported along the continuous channels of the donor and acceptor materials to the anode and cathode, respectively, and collected by the electrodes to be output to an external circuit to form electric current. From the above, the choice of active layer material is critical to the efficiency of the organic solar cell device.
In 2014, university of south-opening Chen Yongsheng et al designed DR3TSBDT based on a benzodithiophene unit with an alkylthio side chain and blended it with PC71BM to achieve 9.95% efficiency. In 2015, chen Yongsheng and the like have performed systematic studies on the number of thiophenes to design DRCN5T of pentacene, which is blended with PC71BM to obtain an efficiency of 10.08%. These results demonstrate the great potential of small organic molecules as active layer donor materials for stacked devices. However, the light conversion efficiency of the organic solar cell device needs to be further improved, and the improvement of the small molecule donor material is important.
Disclosure of Invention
The invention aims to provide an organic compound which is used as a small molecular donor material and applied to an organic solar cell, and can improve the photoelectric conversion efficiency of the device.
In order to achieve the purpose of the invention, the technical solution is as follows:
an organic compound having a structure represented by the general formula (I):
wherein:
a is independently selected from the structural formula (A-1) for each occurrence:
* Represents a ligation site;
x is independently selected from O atom or C (CN) for each occurrence 2 ；
R 1 -R 10 Each independently selected from: -H, -D, having 1 to 20C atomsStraight-chain alkyl, straight-chain alkoxy having 1 to 20C atoms, straight-chain alkylthio having 1 to 20C atoms, branched or cyclic alkyl having 3 to 20C atoms, branched or cyclic alkoxy having 3 to 20C atoms, branched or cyclic alkylthio having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amino, -CF 3 -Cl, -Br, -F, -I, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6 to 50 ring atoms, substituted or unsubstituted heteroaryl having 5 to 50 ring atoms, aryloxy having 6 to 50 ring atoms, heteroaryloxy having 5 to 50 ring atoms, or a combination thereof; wherein R is 7 -R 10 Two adjacent groups of the two groups are mutually cyclic or not cyclic;
m is selected from 0, 1, 2, 3, 4, 5 or 6;
n is selected from 0, 1, 2, 3, 4, 5 or 6.
Accordingly, the present application also provides a mixture comprising the above-described organic compound and at least one organic functional material selected from the group consisting of an anode buffer layer material, a cathode buffer layer material, an active layer donor material, or an active layer acceptor material.
Accordingly, the present application also provides an electron donor material selected from the organic compounds or mixtures as described above.
Correspondingly, the application also provides an organic electronic device, which comprises at least one functional layer, wherein the material of the functional layer is selected from the organic compound or the mixture.
Compared with the prior art, the application has the remarkable advantages that: the small molecule donor material of the application is based on an A-pi-D-pi-A structure and a donor unit D Has the following characteristics ofGreater conjugated system and planar symmetry and excellent charge transport properties, acceptor unit A>The compound can provide better photovoltaic performance, and can regulate and control the absorption, energy level and band gap of the compound, so that the compound has proper energy level; the introduction of naphthyl into the linking unit pi increases the overlap of pi orbitals, thereby increasing charge mobility by maximizing electron coupling between adjacent molecules. The organic compound provided by the application is applied to an organic solar cell device as a small molecular donor material, and can improve the photoelectric conversion efficiency of the device.
Detailed Description
The application provides an organic compound, a mixture and application thereof in an organic electronic device, and the application is further described in detail below for the purpose, technical scheme and effect of the application to be clearer and clearer. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the application.
The term "and/or," "and/or," as used herein, includes any one of two or more of the listed items in relation to each other, as well as any and all combinations of the listed items in relation to each other, including any two of the listed items in relation to each other, any more of the listed items in relation to each other, or all combinations of the listed items in relation to each other. It should be noted that, when at least three items are connected by a combination of at least two conjunctions selected from the group consisting of "and/or", "and/or", it should be understood that, in the present application, the technical solutions include technical solutions that all use "logical and" connection, and also include technical solutions that all use "logical or" connection. For example, "a and/or B" includes three parallel schemes A, B and a+b. For another example, the technical schemes of "a, and/or B, and/or C, and/or D" include any one of A, B, C, D (i.e., the technical scheme of "logical or" connection), and also include any and all combinations of A, B, C, D, i.e., any two or three of A, B, C, D, and also include four combinations of A, B, C, D (i.e., the technical scheme of "logical and" connection).
In the present invention, the organic photovoltaic device and the organic solar cell have the same meaning and can be interchanged.
In the present invention, aromatic groups and aromatic ring systems have the same meaning and can be interchanged.
In the present invention, the heteroaromatic groups, heteroaromatic groups and heteroaromatic ring systems have the same meaning and can be interchanged.
In the present invention, the "heteroatom" is a non-carbon atom, and may be an N atom, an O atom, an S atom, or the like.
In the present invention, "substituted" means that one or more hydrogen atoms in the substituted group are substituted with the substituent.
In the present invention, the same substituent may be independently selected from different groups when it appears multiple times. If the general formula contains a plurality of R, R can be independently selected from different groups.
In the present invention, "substituted or unsubstituted" means that the defined group may or may not be substituted. When a defined group is substituted, it is understood that the defined group may be substituted with one or more substituents R selected from, but not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1 to 20C atoms, heterocyclyl containing 3 to 20 ring atoms, aromatic containing 6 to 20 ring atoms, heteroaromatic containing 5 to 20 ring atoms, -NR' R ", silane, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and which may be further substituted with substituents acceptable in the art; it is understood that R 'and R "in-NR' R" are each independently selected from, but not limited to: H. deuterium atoms, cyano groups, isocyano groups, nitro groups or halogen groups, alkyl groups containing 1 to 10C atoms, heterocyclic groups containing 3 to 20 ring atoms, aromatic groups containing 6 to 20 ring atoms, heteroaromatic groups containing 5 to 20 ring atoms. Preferably, R is selected from, but not limited to: deuterium atoms, cyano groups, isocyano groups, nitro groups or halogen groups, alkyl groups containing 1 to 10C atoms, heterocyclic groups containing 3 to 10 ring atoms, aromatic groups containing 6 to 20 ring atoms, heteroaromatic groups containing 5 to 20 ring atoms, silane groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, carbamoyl groups, haloformyl groups, formyl groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, trifluoromethyl groups, and which may be further substituted with substituents acceptable in the art.
In the present invention, the "number of ring atoms" means the number of atoms among atoms constituting the ring itself of a structural compound (for example, a monocyclic compound, a condensed ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below, unless otherwise specified. For example, the number of ring atoms of the benzene ring is 6, the number of ring atoms of the naphthalene ring is 10, and the number of ring atoms of the thienyl group is 5.
"aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removal of one hydrogen atom, which may be a monocyclic aryl group, or a fused ring aryl group, or a polycyclic aryl group, at least one of which is an aromatic ring system for a polycyclic species. For example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" means an aryl group having 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthryl, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, perylenyl, acenaphthylenyl and derivatives thereof. It will be appreciated that a plurality of aryl groups may also be interrupted by short non-aromatic units (e.g. <10% of non-H atoms, such as C, N or O atoms), such as acenaphthene, fluorene, or 9, 9-diaryl fluorene, triarylamine, diaryl ether systems in particular should also be included in the definition of aryl groups.
"heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, which may be an N atom, an O atom, an S atom, or the like. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" refers to heteroaryl having 5 to 40 ring atoms, preferably substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, particularly preferably substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted, suitable examples include, but are not limited to: thienyl, furyl, pyrrolyl, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiophenoyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, phthalazinyl, phenanthridinyl, primary pyridyl, quinazolinonyl, dibenzothienyl, dibenzofuranyl, carbazolyl, and derivatives thereof.
In the present invention, "alkyl" may denote a linear, branched and/or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 15, or 1 to 6. Phrases containing this term, e.g., "C 1-9 Alkyl "means an alkyl group containing 1 to 9 carbon atoms, and each occurrence may be, independently of the other, C 1 Alkyl, C 2 Alkyl, C 3 Alkyl, C 4 Alkyl, C 5 Alkyl, C 6 Alkyl, C 7 Alkyl, C 8 Alkyl or C 9 An alkyl group. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylThe present invention relates to a process for the preparation of a catalyst comprising the steps of (a) pentylphenyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentylmethyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-hexyloctyl, 3, 7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, and the like.
"amine group" refers to a derivative of an amine having the formula-N (X) 2 Wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, or the like. Non-limiting types of amine groups include-NH 2 -N (alkyl) 2 -NH (alkyl), -N (cycloalkyl) 2 -NH (cycloalkyl), -N (heterocyclyl) 2 -NH (heterocyclyl), -N (aryl) 2 -NH (aryl), -N (alkyl) (heterocyclyl), -N (cycloalkyl) (heterocyclyl), -N (aryl) (heteroaryl), -N (alkyl) (heteroaryl), and the like.
In the present invention, as defined herein, hydroxyl means-OH, carboxyl means-COOH, carbonyl means-C (=o) -, amino means-NH 2, formyl means-C (=o) H, haloformyl means-C (=o) Z (wherein Z represents halogen), carbamoyl means-C (=o) NH2, isocyanato means-NCO, isothiocyanato means-NCS.
The term "alkoxy" refers to a group of the structure "-O-alkyl", i.e. an alkyl group as defined above is attached to other groups via an oxygen atom. Phrases containing this term, suitable examples include, but are not limited to: methoxy (-O-CH) 3 or-OMe), ethoxy (-O-CH 2 CH 3 or-OEt) and t-butoxy (-O-C (CH) 3 ) 3 or-OtBu).
The term "alkylthio" refers to a group of the structure "-S-alkyl", i.e. an alkyl group as defined above is attached to other groups via a sulfur atom. Phrases containing this term, suitable examples include, but are not limited to: methylthio (-S-CH) 3 or-SMe), ethylthio (-S-CH) 2 CH 3 or-SEt) and t-butylsulfanyl (-S-C (CH) 3 ) 3 or-StBu).
In the present invention "×" associated with a single bond represents a linking or fusing site;
in the present invention, when no linking site is specified in the group, an optionally-ligatable site in the group is represented as a linking site;
in the present invention, when the same group contains a plurality of substituents of the same symbol, each substituent may be the same or different from each other, for exampleThe 6R groups on the benzene ring may be the same or different from each other.
As used in the present invention, "a combination thereof", "any combination thereof", "combination", and the like include all suitable combinations of any two or more of the listed items.
In the present invention, "further", "still further", "particularly" and the like are used for descriptive purposes to indicate differences in content but should not be construed as limiting the scope of the invention.
In the present invention, "optional" means optional or not, that is, means any one selected from two parallel schemes of "with" or "without". If multiple "alternatives" occur in a technical solution, if no particular description exists and there is no contradiction or mutual constraint, then each "alternative" is independent.
In the invention, the technical characteristics described in an open mode comprise a closed technical scheme composed of the listed characteristics and also comprise an open technical scheme comprising the listed characteristics.
An organic compound having a structure represented by the general formula (I):
wherein:
a is independently selected from the structural formula (A-1) for each occurrence:
* Represents a ligation site;
x is independently selected from O atom or C (CN) for each occurrence 2 ；
R 1 -R 10 Each independently selected from: -H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain alkylthio having 1 to 20C atoms, branched or cyclic alkyl having 3 to 20C atoms, branched or cyclic alkoxy having 3 to 20C atoms, branched or cyclic alkylthio having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amino, -CF 3 -Cl, -Br, -F, -I, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6 to 50 ring atoms, substituted or unsubstituted heteroaryl having 5 to 50 ring atoms, aryloxy having 6 to 50 ring atoms, heteroaryloxy having 5 to 50 ring atoms, or a combination thereof A group formed by combination; wherein R is 7 -R 10 Two adjacent groups of the two groups are mutually cyclic or not cyclic;
m is selected from 0, 1, 2, 3, 4, 5 or 6;
n is selected from 0, 1, 2, 3, 4, 5 or 6.
In the present invention, preferably, "mutually cyclic or acyclic" means that two adjacent substituents are linked to each other to form a ring system or acyclic; preferably, "inter-cyclic" forms a 5-membered ring or a 6-membered ring; more preferably, a substituted or unsubstituted 6 membered aromatic or heteroaromatic ring or cyclohexyl is formed.
In one embodiment, R 1 -R 10 Each independently selected from: -H, -D, straight chain alkyl having 1 to 10C atoms, straight chain alkoxy having 1 to 10C atoms, straight chain alkylthio having 1 to 10C atoms, branched or cyclic alkyl having 3 to 10C atoms, branched or cyclic alkoxy having 3 to 20C atoms, branched or cyclic alkylthio having 3 to 10C atoms, cyano, isocyano, hydroxy, nitro, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, an aryloxy group having 6 to 30 ring atoms, a heteroaryloxy group having 5 to 30 ring atoms, or a combination thereof.
In one embodiment, each occurrence of A is independently selected from formulas (1-1) or (1-2) or (1-3):
in one embodiment, R 7 -R 10 Each independently selected from: -H, -D, straight-chain alkyl having 1 to 10C atoms, branched or cyclic alkyl having 3 to 10C atoms, cyano, isocyano, hydroxy, nitro, -CF 3 -Cl, -Br, -F, or-I, or a combination of the foregoing.
Preferably, R 7 -R 10 Each independently selected from: -H, -D, -F, -I, -Cl,Cyano, nitro, -CF 3 Methyl or tert-butyl; r is R 8 ,R 9 With or without each other being cyclic; when R is 8 ,R 9 When forming a ring, a six-membered benzene ring is formed.
In a specific embodiment, A is selected from any of formulas (2-1) to (2-69):
in one embodiment, R 1 -R 2 Each independently selected from: -H, -D, linear alkyl having 1 to 10C atoms, linear alkoxy having 1 to 10C atoms, linear alkylthio having 1 to 10C atoms, branched or cyclic alkyl having 3 to 10C atoms, branched or cyclic alkoxy having 3 to 10C atoms, branched or cyclic alkylthio having 3 to 10C atoms, -CF 3 -Cl, -Br, -F, -I, an aromatic group having 6 to 10 ring atoms, a heteroaromatic group having 5 to 10 ring atoms, or a combination of the foregoing.
In one embodiment, R 1 -R 2 Each independently selected from: -H, -D, a linear alkyl group having 1 to 10C atoms, a linear alkoxy group having 1 to 10C atoms, a linear alkylthio group having 1 to 10C atoms, a branched alkyl group having 3 to 10C atoms, a branched alkoxy group having 3 to 10C atoms, a branched alkylthio group having 3 to 10C atoms, structural formula (2-1), or a combination thereof;
wherein: r is R 11 Each occurrence is independently selected from the group consisting of-H, -D, a linear alkyl group having 1 to 10C atoms, a linear alkoxy group having 1 to 10C atoms, a branched alkyl group having 1 to 10C atoms, and a branched alkyl group having 1 to 10C atomsStraight-chain alkylthio having 1 to 10C atoms, branched alkyl having 3 to 10C atoms, branched alkoxy having 3 to 10C atoms, branched alkylthio having 3 to 10C atoms, -CF 3 -Cl, -Br, -F, -I, or a combination of the foregoing; r is R 11 The selected groups may be the same or different for each occurrence.
In one embodiment, R 1 And R is 2 Selected from the same structures.
In one embodiment, R 3 -R 6 Each independently selected from: -H, -D, linear alkyl having 1 to 10C atoms, linear alkoxy having 1 to 10C atoms, linear alkylthio having 1 to 10C atoms, branched or cyclic alkyl having 3 to 10C atoms, branched or cyclic alkoxy having 3 to 10C atoms, branched or cyclic alkylthio having 3 to 10C atoms, -CF 3 -Cl, -Br, -F, -I, or a combination of the foregoing.
In one embodiment, R 3 -R 4 Each independently selected from: -H, a linear alkyl group having 1 to 10C atoms, or a branched alkyl group having 3 to 10C atoms. Further, R 3 Each occurrence being selected from the same group; r is R 4 Each occurrence is selected from the same group.
In a preferred embodiment, R 5 -R 6 Each independently selected from: cyano, -CF 3 Or F. More preferably, m is selected from 1 or 2 and n is selected from 1 or 2.
In a more specific embodiment of the present application,and/or +.>Selected from the following structures:
more preferably, R 5 -R 6 Selected from the group consisting ofThe same groups. Most preferably, the first and second heat exchangers are arranged,selected from the same groups.
In the present application, "straight-chain alkyl group having 1 to 20C atoms" is preferably selected from methyl, ethyl, C 8 H 17 、C 6 H 13 、C 5 H 11 The method comprises the steps of carrying out a first treatment on the surface of the The "branched alkyl group having 3 to 20C atoms" is preferably selected from: t-butyl, isopropyl,
The organic compound according to the present application may be selected from, but is not limited to, the following structures:
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the organic compound can be used as an active layer material for organic electronic devices; preferably, the organic compounds according to the application can be used as active layer donor materials in organic solar devices.
The application further relates to a mixture comprising at least one organic compound as described above and at least one further organic functional material, which is selected from the group consisting of anode buffer layer material, cathode buffer layer material, active layer donor material, or active layer acceptor material. The weight ratio of the polymer to the other acceptor material is from 1:99 to 99:1. In one embodiment, the photoactive layer comprises a donor material and an acceptor material in a weight ratio of donor material/acceptor material = 1/1.2.
In an embodiment, the further organic functional material is selected from an active layer donor material or an active layer acceptor material.
The application further relates to an electron donor material selected from the group of organic compounds or mixtures as described above.
The application further relates to the use of an organic compound or mixture as described above in an organic electronic device. The organic electronic device may be selected from, but not limited to, organic solar cells (OPV), organic Light Emitting Diodes (OLED), organic light emitting cells (olec), organic Field Effect Transistors (OFET), organic light emitting field effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (Organic Plasmon Emitting Diode), etc., with OPV being particularly preferred.
The application also relates to an organic electronic device comprising at least one functional layer, wherein the functional layer comprises the organic compound or the mixture. Preferably, the functional layer is selected from an anode buffer layer, an active layer, or a cathode buffer layer.
In one embodiment, the organic electronic device includes at least a first electrode, a second electrode, and one or more functional layers between the first electrode and the second electrode. Preferably, the one or more functional layers are selected from active layers; more preferably, the one or more functional layers are selected from the group consisting of anode buffer layers, active layers, and cathode buffer layers.
Further, the organic solar cell further includes a substrate. In particular, the substrate may be disposed at a lower portion of the first electrode.
In one embodiment, the first electrode is an anode and the second electrode is a cathode; in another embodiment, the first electrode may be a cathode and the second electrode may be an anode.
In one embodiment, as the substrate, a substrate having excellent transparency, surface roughness, ease of handling, and water repellency may be used. Specifically, a glass substrate, a thin film glass substrate, or a transparent plastic substrate may be used. The plastic substrate may include a film in the form of a single layer or a plurality of layers, such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyetheretherketone (PEEK), polyimide (PI), etc., but is not limited thereto, and a substrate commonly used for an organic solar cell may be used.
The anode electrode may be made of a transparent or translucent material, but is not limited thereto. The anode electrode may comprise a metal such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO: al or SnO 2 Sb; and conductive polymers, such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxythiophene)](PEDOT), polypyrrole, polyaniline, and the like, but is not limited thereto.
The cathode electrode may be made of a low work function metal. The cathode electrode includes a metal such as silver (Ag), aluminum (Al), platinum (Pt), tungsten (W), copper (Cu), molybdenum (Mo), gold (Au), nickel (Ni), and palladium (Pd), or an alloy thereof; and materials having a multi-layer structure, e.g.LiF/Al、LiO 2 /Al、LiF/Fe、MoO 3 /Al、Al∶Li、Al∶BaF 2 Al: baF 2 ∶Ba。
The active layer includes an electron donor material and an electron acceptor material. In the present specification, the active layer material may mean an electron donor material and an electron acceptor material.
In particular, the electron acceptor material may be a fullerene derivative or a non-fullerene derivative. Fullerene molecules include hollow spheres, ellipsoids, or tubes. The fullerene acceptor may be a spherical C20 or C2n molecule, where n is an integer ranging from, for example, 12 to 100. In some examples, the fullerene receptor is C60 or C70 or a derivative thereof, such as PC 61 BM、PC 71 BM (BM). The non-fullerene acceptor material may be selected from Y6, EH-IDTBR, TTPBT-IC, IEICO-4F, HEICO-4F or the following structures, but is not limited thereto:
the photoactive layer may be formed by the following method: the photoactive material, such as an electron donor and/or electron acceptor, is dissolved in an organic solvent and then the resulting solution is coated by methods such as spin coating, dip coating, screen printing, gravure printing, spray coating, doctor blade, slot coating, and ink jet printing, but the method is not limited thereto.
The anode buffer layer is a high work function material, which may be selected from PEDOT of poly (styrenesulfonic acid): PSS (poly (3, 4-ethylenedioxythiophene)), molybdenum oxide (MoOx), vanadium oxide (V) 2 O 5 ) Nickel oxide (NiO), tungsten oxide (WO x ) And the like, preferably, x is selected from 2 or 3, but is not limited thereto.
The cathode buffer layer material can be metal oxide or polymer with low work function, and the metal oxide can be metal complex containing 8-hydroxyquinoline and Alq 3 Metal complex containing Liq, liF, ca, titanium oxide (TiOx), zinc oxide (ZnO), cesium carbonate (Cs 2 CO 3 ) And the like, the polymer may be PFN-Br, PFN or the like, but is not limited thereto.
The invention also relates to the use of the organic solar cell according to the invention in various devices including, but not limited to, automotive and Building Integrated Photovoltaics (BIPV), electronic price tags, indoor photovoltaics, internet of things, smart agriculture, and the like.
The invention will be described in connection with preferred embodiments, but the invention is not limited to the embodiments described below, it being understood that the appended claims outline the scope of the invention and those skilled in the art, guided by the inventive concept, will recognize that certain changes made to the embodiments of the invention will be covered by the spirit and scope of the claims.
The organic compound and the organic electronic device according to the present invention are exemplified herein, but the present invention is not limited to the following examples.
Example 1: synthesis of Compound 1
Synthesis of Compounds 1-2:
in a 250ml round bottom flask, starting materials 1-1 (14.4 g,40 mmol) and starting material A (10.16 g,20 mmol) were weighed and dissolved in 100ml tetrahydrofuran, and ditriphenylphosphine palladium dichloride (0.31 g,0.44 mmol) was added to the system under argon. The mixture was refluxed at 80℃for 14h. Cooling to room temperature, spin-drying tetrahydrofuran, extracting with dichloromethane, spin-drying solvent to obtain crude product, separating and purifying with silica gel column chromatography to obtain solid (11.9 g) which is compound 1-2; the yield thereof was found to be 80%. MS:748.62.
synthesis of Compounds 1-4:
in a 250ml round bottom flask, starting materials 1-3 (9.93 g,30 mmol) and compounds 1-2 (11.2 g,15 mmol) were weighed into 100ml tetrahydrofuran and bis triphenylphosphine palladium dichloride (0.63 g,0.9 mmol) was added to the system under argon. The mixture was refluxed at 80℃for 14h. Cooling to room temperature, steaming to remove tetrahydrofuran, extracting with dichloromethane, steaming to remove solvent to obtain crude product, and separating and purifying by silica gel column chromatography to obtain solid (12.7 g) which is compound 1-4; the yield thereof was found to be 83%. MS:1012.54.
Synthesis of Compounds 1-5:
accurately weighing the compounds 1-4 (10.1 g,10 mmol) in a 250ml three-mouth bottle, adding 100ml DMF, controlling the temperature to 0-5 ℃ by ice water bath, slowly dropwise adding a DMF solution of NBS (3.54 g, 20 mmol), heating to room temperature for reaction for 8 hours after the dropwise addition, pouring the reaction solution into 500ml water after the reaction is finished, extracting three times by using 200ml dichloromethane, merging organic phases, washing by saturated saline solution, drying by anhydrous sodium sulfate, filtering, and concentrating filtrate to obtain a crude product of the compounds 1-5. Yield: 90%. MS:1170.06.
Synthesis of Compounds 1-7:
accurately weighing 1-5 (9.33 g,8 mmol) of the compound, 1-6 (3.2 g,16 mmol) of the raw material, and tetra-triphenylphosphine palladium (0.46 g,0.4 mmol) of potassium carbonate (4.42 g,32 mmol) into a 1000mL three-necked flask, adding 100mL of toluene and 20mL of water, replacing nitrogen for three times, and heating to 80 ℃ for reaction overnight. After the raw materials are completely reacted, cooling to room temperature, adding water for dilution, extracting with ethyl acetate for three times, combining organic phases, removing redundant solvent by reduced pressure distillation, separating by silica gel column chromatography, wherein the eluting agent is PE:EA=10:1 (volume ratio) to obtain about 7.5g of compound 1-7, and the yield is: 70%. MS:1320.78.
synthesis of Compound 1:
accurately weighing 1-7 (6.6 g,5 mmol) of the compound, 1-8 (1.46 g,10 mmol) of the raw material, and sodium hydroxide (4 g,100 mmol) of the raw material, sequentially adding the raw material into a 250mL three-neck flask, adding 100mL of anhydrous o-dichlorobenzene, pumping and charging nitrogen three times, and heating to 120 ℃ for reaction for 12 hours. After the reaction is finished, cooling to room temperature, adding water for dilution, extracting with ethyl acetate for three times, distilling under reduced pressure to remove redundant solvent, separating by silica gel column chromatography, and obtaining about 5.1g of compound 1 by using petroleum ether as eluent. Yield: 65%, ms (MALDI-TOF MS): 1576.49.
Example 2: synthesis of Compound 13
Synthesis of Compound 13-1:
7-bromo-1-fluoronaphthalene (11.2 g,50 mmol) and 100ml phosphorus oxychloride were weighed in a 500ml round bottom flask and the mixture refluxed for 6 hours at 80℃under argon. After the reaction is finished, cooling to room temperature, slowly pouring the reaction solution into warm water, extracting with dichloromethane, combining organic phases, washing with saturated saline water, drying with anhydrous sodium sulfate, evaporating the solvent to obtain a crude product, and separating and purifying by silica gel column chromatography to obtain 13-1 about 12.7g of solid; the yield thereof was found to be 50%. MS:254.05.
Compound 13-2 synthesis:
accurately weighing compound 13-1 (9.33 g,25 mmol), pinacol biborate (7.6 g,30 mmol), tetraphenylphosphine palladium (0.23 g,0.5 mmol), potassium acetate (4.42 g,32 mmol) were sequentially added into a 250mL three-necked flask, 100mL of 1, 4-dioxane was added, nitrogen was replaced three times, and the temperature was raised to 90℃for reaction overnight. After the raw materials are completely reacted, cooling to room temperature, removing 1, 4-dioxane, methylene dichloride and water solution by reduced pressure distillation, combining organic phases, drying, concentrating to remove methylene dichloride, pulping by petroleum ether to obtain solid 13-2 about 6g, and obtaining the yield: 80%. MS 301.08
Synthesis of Compound 13-3:
specific methods reference the synthesis of compounds 1-7, differing in that: the raw material 1-6 is replaced by the raw material 13-2 to obtain the compound 13-3 with 75% yield. Ms (MALDI-TOF MS): 1356.17
Synthesis of Compound 13:
specific methods reference the synthesis of compound 1, differing in that: the replacement of compound 1-7 and starting material 1-8 with compound 13-3 and starting material 13-4 gave compound 13 in 60% yield, ms (MALDI-TOF MS): 1708.27.
Example 3: synthesis of Compound 27
Synthesis of Compound 27:
synthesis of Compound 27-2:
specific methods reference the synthesis of compounds 1-2, differing in that: the difference is that: the raw material 1-1 is replaced by the raw material 27-1 to obtain a compound 27-2 with a yield of 78%; MS:748.72.
synthesis of Compound 27-4:
specific methods reference the synthesis of compounds 1-4, differing in that: replacing raw material 1-3 with raw material 27-3 and replacing compound 1-2 with compound 27-2 to obtain compound 27-4 with a yield of 72%; MS:1068.56.
synthesis of Compound 27-5:
specific methods reference the synthesis of compounds 1-5, differing in that: replacement of compound 1-4 with compound 27-4 gives compound 27-5. The yield thereof was found to be 81%. MS (MALDI-TOF MS): 1226.38.
synthesis of Compound 27-6:
specific methods reference the synthesis of compounds 1-7, differing in that: replacement of compound 1-5 with compound 27-5 gives compound 27-6. The yield thereof was found to be 85%. MS (MALDI-TOF MS): 1376.57.
Synthesis of Compound 27:
specific methods reference the synthesis of compound 1, differing in that: replacement of compounds 1-7 with compounds 27-6 and starting materials 1-8 with starting materials 27-7 gave compound 27 in 67% yield, ms (MALDI-TOF MS): 1732.54.
Example 4: synthesis of Compound 43
Synthesis of Compound 43-1:
specific methods reference the synthesis of compounds 1-4, differing in that: the compound 1-2 was replaced with the starting material B to give the compound 43-1 in a yield of 72.5%. MS:623.71.
synthesis of Compound 43-2:
specific methods reference the synthesis of compounds 1-5, differing in that: replacement of compound 1-4 with compound 43-1 gave compound 43-2 in 82.1% yield. MS:781.59.
synthesis of intermediate 43-4:
specific methods reference the synthesis of compounds 1-7, differing in that: replacement of compound 1-5 with compound 43-2 and starting material 1-6 with starting material 43-3 gives compound 43-4 in 77.5% yield. MS:932.05.
synthesis of Compound 43:
specific methods reference the synthesis of compound 1, differing in that: replacement of compound 1-7 with compound 43-4 and starting material 1-8 with starting material 43-5 gives compound 43 in 45.5% yield, ms (MALDI-TOF MS): 1380.07.
Example 5: synthesis of Compound 46
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Synthesis of Compound 46-1:
in a 250ml round bottom flask, raw material C (16.3 g,50 mmol) and 2-ethylhexanol are dissolved in 100ml NMP, 32.5g cesium carbonate is added, the mixture is refluxed under the protection of argon for 20 hours, after the reaction is completed, the mixture is cooled to room temperature, poured into 500ml water, and suction filtration is carried out to obtain a crude product, and the crude product is separated and purified by silica gel column chromatography to obtain 46-1 about 20.5 g, and the yield is: 75.2%. MS:547.71.
synthesis of Compound 46-2:
specific methods reference the synthesis of compounds 1-5, differing in that: replacement of compound 1-4 with compound 46-1 gives compound 46-2 in a yield of 84.5%. MS:705.43.
synthesis of Compound 46-4:
specific methods reference the synthesis of compounds 1-4, differing in that: replacement of compound 1-2 with compound 46-2 and starting 1-3 with starting 46-3 gives compound 46-4 in 67.2% yield. MS:935.40.
synthesis of Compound 46-5:
specific methods refer to the synthesis of compound 1-5, except that compound 1-4 was replaced with compound 46-4 to give compound 46-5 in 78.5% yield. MS:1093.98.
synthesis of Compound 46-6:
specific methods refer to the synthesis of compound intermediate 1-7, except that compound 1-5 was replaced with intermediate 46-5 and starting material 1-6 was replaced with compound 43-3, yielding compound 46-6 in a yield of 72.4%. MS:1244.07.
Synthesis of Compound 46:
specific methods reference the synthesis of compound 1, differing in that: replacement of compound 1-7 with compound 46-6 and starting material 1-8 with starting material 46-7 gives compound 46 in 40.1% yield, ms (MALDI-TOF MS): 1572.19.
Example 6: synthesis of Compound 50
Synthesis of Compound 50-1:
specific methods reference the synthesis of compounds 1-4, differing in that: replacing the compound 1-2 with the compound 46-2 and replacing the raw material 1-3 with the raw material 27-3 to obtain a compound 50-1 with a yield of 72%; MS:936.27.
synthesis of Compound 50-2:
specific methods reference the synthesis of compounds 1-5, differing in that: replacement of compound 1-4 with compound 50-1 gives compound 50-2 in 81% yield. MS:1094.06.
synthesis of Compound 50-3:
the specific method refers to the synthesis of the compound 1-7, and the difference is that the compound 1-5 is replaced by the compound 50-2 and the raw material 1-6 is replaced by the compound 13-2, so that the compound 50-3 is obtained, and the yield is 72%. MS:1280.71.
synthesis of Compound 50:
specific methods reference the synthesis of compound 1, differing in that: replacement of compound 1-7 with compound 50-3 and starting material 1-8 with starting material 13-4 gives compound 50 in 52% yield, ms (MALDI-TOF MS): 1632.78.
Example 7: synthesis of Compound 52
Synthesis of Compound 52-2:
specific methods reference the synthesis of compound 46-1, differing in that: the starting material 2-ethylhexanol was replaced with 52-1 to give compound 52-2, yield: 77%. MS:579.62.
synthesis of Compound 52-3:
specific methods reference the synthesis of compounds 1-5, differing in that: replacement of compound 1-4 with compound 52-2 gives compound 52-3 in 86% yield. MS:737.48.
synthesis of Compound 52-5:
specific methods reference the synthesis of compounds 1-4, differing in that: the compound 52-5 was obtained in 82% yield by substituting the compound 1-2 with the compound 52-3 and substituting the raw material 1-3 with the raw material 52-4. MS:743.91.
synthesis of Compound 52-6:
specific methods reference the synthesis of compounds 1-5, differing in that: replacement of compound 1-4 with compound 52-5 gave compound 52-6 in 74% yield. MS:901.74.
synthesis of Compound 52-7:
the specific method refers to the synthesis of compound 1-7, except that compound 1-5 is replaced with raw material 52-6 and raw material 1-6 is replaced with 43-3, to obtain compound 52-7 with a yield of 62%. MS:1052.49.
synthesis of compound 52:
specific methods reference the synthesis of compound 1, differing in that: replacement of compound 1-7 with compound 52-7 and starting material 1-8 with starting material 52-8 gives compound 52 in 59% yield, ms (MALDI-TOF MS): 1541.81.
Example 8: synthesis of Compound 60
Synthesis of Compound 60-1:
specific methods reference the synthesis of compounds 1-4, differing in that: the compound 1-2 was replaced with the raw material D and the raw material 1-3 was replaced with the raw material 46-3 to obtain the compound 60-1 in 80% yield. MS:904.47.
synthesis of Compound 60-2:
specific methods reference the synthesis of compounds 1-5, differing in that: the difference is that compound 1-4 was replaced with compound 60-1 in 85% yield. MS:1062.03.
synthesis of Compound 60-3:
the specific method refers to the synthesis of the compound 1-7, and the difference is that the compound 1-5 is replaced by the compound 60-2 and the raw material 1-6 is replaced by the raw material 43-3, so that the compound 60-3 is obtained with the yield of 60%. MS:1212.25.
synthesis of Compound 60:
specific methods reference the synthesis of compound 1, differing in that: replacement of compound 1-7 with starting material 60-4 and starting material 1-8 with compound 60-3 gives compound 60 in 42% yield, ms (MALDI-TOF MS): 1568.29.
Example 9: synthesis of Compound 66
Synthesis of Compound 66-2:
specific methods reference the synthesis of compounds 1-4, differing in that: the compound 1-2 was replaced with the raw material D and the raw material 1-3 was replaced with the raw material 66-1, to obtain the compound 66-2 in 82% yield. MS:848.32.
Synthesis of Compound 66-3:
specific methods reference the synthesis of compounds 1-5, differing in that: the difference is that compound 1-4 was replaced with compound 66-2 in 77% yield. MS:1006.03.
synthesis of Compound 66-4:
specific methods refer to the synthesis of compound 1-7, except that compound 1-5 was replaced with compound 66-3 and starting material 1-6 was replaced with starting material 43-3, yielding compound 66-4 in 66% yield. MS:1156.61.
synthesis of compound 66:
specific methods reference the synthesis of compound 1, differing in that: replacement of compound 1-7 with starting material 66-5 and starting material 1-8 with compound 66-4 gives compound 67 in 57% yield, ms (MALDI-TOF MS): 1592.27.
Example 10: synthesis of Compound 70
Synthesis of Compound 70:
specific methods referring to the synthesis of Compound 1, the substitution of Compound 1-7 with Material 70-1 and of Material 1-8 with Compound 66-4 gave Compound 70 in 61% yield, ms (MALDI-TOF MS): 1876.27.
OPV device preparation:
the process of preparing OPV devices comprising the above compounds is described in detail below by means of specific examples. The OPV device structure is as follows: indium tin oxide ITO/PEDOT PSS/active layer/PFN-Br/Ag.
The device 1 was prepared as follows:
1) Cleaning an ITO substrate:
the ITO conductive glass layer is cleaned by a detergent, then is ultrasonically cleaned by deionized water, acetone and isopropanol for 15 minutes, and is treated in a plasma cleaner for 5 minutes after being dried by nitrogen or oven drying so as to improve the work function of the electrode and the surface wettability.
2) Preparation of anode buffer layer
The PEDOT and PSS are uniformly spin-coated on the ITO in air, the spin-coating speed is 3000-4000rpm, and the anode modification layer with the thickness of 20nm is obtained by drying for 15min at 150 ℃.
3) Photoactive layer preparation
Uniformly spin-coating a photoactive layer material on an anode buffer layer at a rotating speed of 1800-4000rpm in a glove box (inert gas atmosphere) to obtain an active material layer with a total thickness of 100 nm; wherein the donor material in the photoactive layer material is selected from compound 1; the acceptor material is selected from the group consisting of compound Y6; the mass ratio of the donor material to the acceptor material is 1:1.2.
4) Cathode buffer layer preparation
After thermal annealing for 10min on a hot bench at 100 ℃, the cathode buffer layer material PFN-Br is uniformly spin-coated on the active layer, and the spin-coating speed is 1800-4000rpm, so as to obtain the cathode buffer layer with the thickness of 5 nm.
5) Cathode layer preparation
In high vacuum (1X 10) -6 Millibar) Ag was evaporated onto the cathode buffer layer to form a cathode layer with a thickness of 100 nm.
6) Packaging
The device was encapsulated with an ultraviolet curable resin in a nitrogen glove box.
The molecular formula of acceptor Y6 is as follows:
the comparative compound structure ref is as follows:
compound ref synthesis is described in Chemistry of Materials,2013,25 (11): 2274-2281.
Device 2:
the same method as the device 1 is prepared, except that: the donor material in the active layer is compound 13.
Device 3:
the same method as the device 1 is prepared, except that: the donor material in the active layer is selected from compound 27.
Device 4:
the same method as the device 1 is prepared, except that: the donor material in the active layer is selected from compound 43.
Device 5:
the same method as the device 1 is prepared, except that: the donor material in the active layer is selected from compound 46.
Device 6:
the same method as the device 1 is prepared, except that: the donor material in the active layer is selected from compound 50.
Device 7:
the same method as the device 1 is prepared, except that: the donor material in the active layer is selected from compound 52.
Device 8:
the same method as the device 1 is prepared, except that: the donor material in the active layer is selected from compound 60.
Device 9:
the same method as the device 1 is prepared, except that: the donor material in the active layer is selected from compound 66.
Device 10:
the same method as the device 1 is prepared, except that: the donor material in the active layer is selected from compound 70.
Device ref:
the same method as the device 1 is prepared, except that: the donor material in the active layer is selected from compound ref.
Performance test is carried out on the prepared organic solar cell device, a cell current-voltage curve is tested under the irradiation of standard light of a sunlight simulator (SS-F5-3A) AM 1.5G, and photoelectric conversion efficiency is calculated as shown in table 1:
TABLE 1
As can be seen from the device characterization of the device examples described above, the device effect prepared from the compounds protected by the present application is far better than device ref, because: the small molecule donor material of the application is based on an A-pi-D-pi-A structure and a donor unit DHas a large conjugated system and plane symmetry and excellent charge transport properties, and the acceptor unit A>The compound can provide better photovoltaic performance, and can regulate and control the absorption, energy level and band gap of the compound, so that the compound has proper energy level; the introduction of naphthyl into the linking unit pi increases the overlap of pi orbitals, thereby increasing charge mobility by maximizing electron coupling between adjacent molecules. The reason that the photoelectric conversion effect of the device 2 and the device 6 is better is that the pulling electron F is substituted on the connecting group, so that the compound obtains better appearance of the active layer. The organic compound can be used as a small molecular donor material to be applied to an organic solar cell device, so that the photoelectric conversion efficiency of the device is improved.
The above examples further illustrate the content of the application but should not be construed as limiting the application. Modifications and substitutions to the method, steps or conditions of the application without departing from the spirit and nature of the application are intended to be within the scope of the application. The technical means used in the examples are conventional means well known to those skilled in the art unless otherwise indicated.
Claims (10)
1. An organic compound characterized by: has a structure shown in a general formula (I):
wherein:
a is independently selected from the structural formula (A-1) for each occurrence:
* Represents a ligation site;
x is independently selected from O atom or C (CN) for each occurrence 2 ；
R 1 -R 10 Each independently selected from: -H, -D, a linear alkyl group having 1 to 20C atoms, a linear alkoxy group having 1 to 20C atoms, a linear alkyl group having 1 to 20C atomsStraight-chain alkylthio groups of 3 to 20C atoms, branched or cyclic alkyl groups of 3 to 20C atoms, branched or cyclic alkoxy groups of 3 to 20C atoms, branched or cyclic alkylthio groups of 3 to 20C atoms, silyl groups, keto groups of 1 to 20C atoms, alkoxycarbonyl groups of 2 to 20C atoms, aryloxycarbonyl groups of 7 to 20C atoms, cyano groups, carbamoyl groups, haloformyl groups, formyl groups, isocyano groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, nitro groups, amine groups, -CF groups 3 -Cl, -Br, -F, -I, alkenyl having 2-20 carbon atoms, aryl having 6 to 50 ring atoms, heteroaryl having 5 to 50 ring atoms, aryloxy having 6 to 50 ring atoms, heteroaryloxy having 5 to 50 ring atoms; wherein R is 7 -R 10 Two adjacent groups of the two groups are mutually cyclic or not cyclic;
m is selected from 0, 1, 2, 3, 4, 5 or 6.
2. The organic compound according to claim 1, wherein: a is independently selected from the formula (1-1) or (1-2) or (1-3) for each occurrence:
wherein R is 7 -R 10 Each independently selected from: -H, -D, straight-chain alkyl having 1 to 10C atoms, branched or cyclic alkyl having 3 to 10C atoms, cyano, isocyano, hydroxy, nitro, -CF 3 -Cl, -Br, -F, or-I.
3. The organic compound according to claim 1, wherein: a is independently selected from any one of formulae (2-1) to (2-69) for each occurrence:
4. the organic compound according to claim 1, wherein: r is R 1 -R 2 Each independently selected from: -H, -D, linear alkyl having 1 to 10C atoms, linear alkoxy having 1 to 10C atoms, linear alkylthio having 1 to 10C atoms, branched or cyclic alkyl having 3 to 10C atoms, branched or cyclic alkoxy having 3 to 10C atoms, branched or cyclic alkylthio having 3 to 10C atoms, -CF 3 -Cl, -Br, -F, -I, an aromatic group having 6 to 10 ring atoms, a heteroaromatic group having 5 to 10 ring atoms.
5. The organic compound according to claim 1, wherein: r is R 1 -R 2 Each independently selected from: -H, -D, a linear alkyl group having 1 to 10C atoms, a linear alkoxy group having 1 to 10C atoms, a linear alkylthio group having 1 to 10C atoms, a branched alkyl group having 3 to 10C atoms, a branched alkoxy group having 3 to 10C atoms, a branched alkylthio group having 3 to 10C atoms, structural formula (2-1):
R 11 each occurrence is independently selected from: -H, -D, a linear alkyl group having 1 to 10C atoms, a linear alkoxy group having 1 to 10C atoms, a linear alkylthio group having 1 to 10C atoms, a branched alkyl group having 3 to 10C atoms, a branched alkoxy group having 3 to 10C atoms, a branched alkylthio group having 3 to 10C atoms, -CF 3 、-Cl、-Br、-F、-I。
6. The organic compound according to claim 1, wherein: r is R 3 -R 6 Each independently selected from: -H,-D, a linear alkyl group having 1 to 10C atoms, a linear alkoxy group having 1 to 10C atoms, a linear alkylthio group having 1 to 10C atoms, a branched or cyclic alkyl group having 3 to 10C atoms, a branched or cyclic alkoxy group having 3 to 10C atoms, a branched or cyclic alkylthio group having 3 to 10C atoms, -CF 3 、-Cl、-Br、-F、-I。
7. The organic compound according to claim 1, wherein: the organic compound is selected from the following structures:
8. a mixture characterized by: the mixture comprising the organic compound according to any one of claims 1 to 7 and at least one organic functional material selected from the group consisting of anode buffer layer material, cathode buffer layer material, active layer donor material, or active layer acceptor material.
9. An electron donor material characterized by: the electron donor material is selected from the group consisting of the organic compounds according to any of claims 1 to 7 or the mixtures according to claim 8.
10. An organic electronic device comprising at least one functional layer, characterized in that: the functional layer material is selected from the group consisting of the organic compounds according to any of claims 1 to 7 or the mixtures according to claim 8.
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| CN114656489A (en) * | 2022-03-09 | 2022-06-24 | 南方科技大学 | Oligomer receptor, preparation method thereof and photovoltaic device |
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| CN106084186A (en) * | 2016-08-16 | 2016-11-09 | 西安近代化学研究所 | One class solar cell interface based on indenofluorene derivant material |
| CN110776620A (en) * | 2018-07-31 | 2020-02-11 | 华南理工大学 | D-pi-A polymer containing S, S-dioxo-dibenzothiophene derivative unit and preparation method and application thereof |
| CN109134513A (en) * | 2018-09-10 | 2019-01-04 | 中南大学 | A kind of non-fullerene acceptor material of condensed ring diazosulfide base and its preparation method and application |
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