Organic composition and organic photoelectric component using same

Abstract

An organic composition comprising at least one donor material and at least one acceptor material. The donor material comprises at least one organic conjugated polymer or organic conjugated small molecule. The acceptor material comprises a first acceptor material, and the first acceptor material has a structure as shown in a formula I: # imgabs0 #, and a naphthalene ring group at the tail end of # imgabs0 # can effectively improve the stability of the material. R5, R6, R7 and R8 are substituted with at least one substituent group, so that the energy level of the material can be adjusted, and matching of different donor materials is facilitated. The invention also provides an organic photoelectric component which comprises a first electrode, an active layer and a second electrode. The active layer contains the organic composition. The organic photoelectric component has good light response, dark current, detection degree and photoelectric conversion efficiency, and the stability of the component is good.

Description

Technical Field

[0001] The present invention relates to an organic composition applied to an organic photoelectric component, in particular to an organic composition comprising a donor material and an acceptor material and an organic photoelectric component comprising the organic composition. Background Art

[0002] Compared with traditional inorganic optoelectronic components, organic optoelectronic components have a wide light absorption range, a large light absorption coefficient and an adjustable structure. Among them, the light absorption range, energy level and solubility can be adjusted according to the target requirements. In addition, organic materials have the advantages of low cost, flexibility, low toxicity and large-scale production in component manufacturing, making organic optoelectronic components have good competitiveness in various fields, such as organic field effect transistors (Organic field effect transistors, OFETs), organic light emitting diodes (Organic light emitting diodes, OLEDs), organic photovoltaic cells (Organic photovoltaics, OPVs) and organic photodetectors (Organic photodetectors, OPDs).

[0003] Organic light sensing components will have different material requirements depending on different applications, and the demand for applications in the invisible light band will increase significantly. For example, biometric technologies such as vein scanning and recognition, iris recognition, and facial recognition, as well as pulse oximetry measurement of physiological vital signs monitoring technology, which has increased demand due to the COVID-19 epidemic, or mechanical vision applications such as LiDAR and time of flight sensors required by current self-driving cars. Therefore, in the light absorption range of near infrared light or shortwave infrared light corresponding to the above applications, how to provide an organic light sensor with high performance and low cost is currently a very important issue.

[0004] Active layer materials play an important role in organic light sensors and directly affect the performance of components. Active layer materials are divided into two parts: donor and acceptor. For donor materials, the development of DA-type conjugated polymers is the mainstream. The push-pull electron effect performed by the multi-electron unit and the electron-deficient unit in the conjugated polymer can be used to regulate the energy level and energy gap of the polymer. The matching acceptor material is usually a fullerene derivative with high conductivity, and its absorption range is about 400-600nm. However, fullerene derivatives are not easy to adjust in structure, and their absorption and energy level are limited to a certain range, which limits the matching of the overall donor and acceptor materials. With the development of the market, the demand for materials in the near-infrared region is gradually increasing. Even if the absorption range of the conjugated polymer as a donor material can be adjusted to the near-infrared region, it may not be well matched due to the limitation of fullerene acceptors. Therefore, it is necessary to develop non-fullerene acceptors to replace traditional fullerene acceptors. The development of non-fullerene acceptor materials mainly forms ADA ladder molecules with multi-electron centers and electron-deficient units on both sides. D is usually a ladder molecule composed of a benzene ring and thiophene, and A is usually an indanone-cyano (IC) derivative. ITIC is a representative non-fullerene acceptor, which absorbs light at about 600-750nm and has good performance in organic light sensors. In addition to the ADA ladder molecule, in 2019, Yang's team used ladder molecules such as Y6 formed by the AD-A'-DA structure, which expanded the absorption range to 600-900nm, further expanding the absorption spectrum of non-fullerene acceptors to the near-infrared region. Therefore, how to develop an organic composite that is an absorbing material covering near-infrared light and has good component performance is currently a very important topic. Summary of the invention

[0005] Therefore, an object of the present invention is to provide an organic composition having good optical properties and appropriate energy levels, which can be used with suitable p-type materials to make organic optoelectronic components. According to one embodiment of the present invention, the organic composition comprises at least one donor material and at least one acceptor material. The donor material comprises at least one organic conjugated polymer or organic conjugated small molecule. The acceptor material comprises a first acceptor material having a structure as shown in Formula 1:

[0006]

[0007] The nucleus is a phenyl group. Ar1 is a five-membered or six-membered heterocyclic ring containing at least one heteroatom, and the heteroatom is independently selected from at least one of S, N, O and Se. R1, R2, R3 and R4 are independently selected from the following groups and one of their derivatives: C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 ester, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 silylaryl, C1-C30 silylheteroaryl, C1-C30 alkoxyaryl, C1-C30 alkoxyheteroaryl, C1-C30 alkylthioaryl, C1-C30 alkylthioheteroaryl, C1-C30 haloalkylaryl, C1-C30 haloalkylheteroaryl, C2-C30 esteraryl and C2-C30 esteraryl heteroaryl. R5, R6, R7 and R8 are independently selected from the following groups and one of their derivatives: C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, halogen, hydrogen atom and cyano, wherein R5, R6, R7 and R8 are not hydrogen atoms at the same time.

[0008] Wherein, Ar1 is independently selected from one of the following structures:

[0009]

[0010] Among them, R9 and R 10 is independently selected from the following groups and one of their derivatives: halogen, hydrogen atom, cyano, C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 ester, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 silylaryl, C1-C30 silylheteroaryl, C1-C30 alkoxyaryl, C1-C30 alkoxyheteroaryl, C1-C30 alkylthioaryl, C1-C30 alkylthioheteroaryl, C1-C30 haloalkylaryl, C1-C30 haloalkylheteroaryl, C2-C30 esteraryl and C2-C30 esterarylheteroaryl, wherein R9 and R 10 It can be two separate groups or connected to each other by a single bond.

[0011] Wherein, the donor material is further selected from at least one organic conjugated polymer.

[0012] Wherein, the organic conjugated polymer comprises one of the following structures:

[0013]

[0014] Among them, Ar2, Ar3, Ar4 and Ar5 are monocyclic or polycyclic structures each containing 4 to 30 ring atoms. n is the number of molecules, and n is a positive integer from 1 to 1000. x and y are mole fractions, where 0 < x < 1, 0 < y < 1 and x + y = 1.

[0015] Among them, Ar2 and Ar4 are independently selected from one of the following structures:

[0016]

[0017]

[0018] Among them, A1, A2, A3 and A4 are independently selected from one of O, S, Se and N-R, and R is selected from one of the following groups and their derivatives: alkyl with 1 to 30 carbon atoms, silyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, alkylthio with 1 to 30 carbon atoms, haloalkyl with 1 to 30 carbon atoms, ester group with 2 to 30 carbon atoms, alkylaryl with 1 to 30 carbon atoms, alkylheteroaryl with 1 to 30 carbon atoms, silylaryl with 1 to 30 carbon atoms, silylheteroaryl with 1 to 30 carbon atoms, alkoxyaryl with 1 to 30 carbon atoms, alkoxyheteroaryl with 1 to 30 carbon atoms, alkylthioaryl with 1 to 30 carbon atoms, alkylthioheteroaryl with 1 to 30 carbon atoms, haloalkylaryl with 1 to 30 carbon atoms, haloalkylheteroaryl with 1 to 30 carbon atoms, ester group aryl with 2 to 30 carbon atoms and ester group heteroaryl with 2 to 30 carbon atoms. R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 are independently selected from one of the following groups and their derivatives: hydrogen atom, halogen, cyano, alkyl with 1 to 30 carbon atoms, silyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, alkylthio with 1 to 30 carbon atoms, haloalkyl with 1 to 30 carbon atoms, ester group with 2 to 30 carbon atoms, alkylaryl with 1 to 30 carbon atoms, alkylheteroaryl with 1 to 30 carbon atoms, silylaryl with 1 to 30 carbon atoms, silylheteroaryl with 1 to 30 carbon atoms, alkoxyaryl with 1 to 30 carbon atoms, alkoxyheteroaryl with 1 to 30 carbon atoms, alkylthioaryl with 1 to 30 carbon atoms, alkylthioheteroaryl with 1 to 30 carbon atoms, haloalkylaryl with 1 to 30 carbon atoms, haloalkylheteroaryl with 1 to 30 carbon atoms, ester group aryl with 2 to 30 carbon atoms and ester group heteroaryl with 2 to 30 carbon atoms.

[0019] Among them, Ar3 and Ar5 are independently selected from one of the following structures:

[0020]

[0021]

[0022] A5, A6, A7 and A8 are independently selected from one of O, S, Se and NR, and R is selected from one of the following groups and their derivatives: C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 ester, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 silylaryl, C1-C30 silylheteroaryl, C1-C30 alkoxyaryl, C1-C30 alkoxyheteroaryl, C1-C30 alkylthioaryl, C1-C30 alkylthioheteroaryl, C1-C30 haloalkylaryl, C1-C30 haloalkylheteroaryl, C2-C30 esteraryl and C2-C30 esteraryl heteroaryl. 17 , R 18 , R 19 , R 20 , R 21 and R 22 Independently selected from the following groups and one of their derivatives: hydrogen atom, halogen, cyano, C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 ester, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 silylaryl, C1-C30 silylheteroaryl, C1-C30 alkoxyaryl, C1-C30 alkoxyheteroaryl, C1-C30 alkylthioaryl, C1-C30 alkylthioheteroaryl, C1-C30 haloalkylaryl, C1-C30 haloalkylheteroaryl, C1-C30 esteraryl and C2-C30 esterarylheteroaryl.

[0023] Wherein, the receptor material further comprises a second receptor material, and the second receptor material is an organic conjugated polymer or an organic conjugated small molecule.

[0024] Wherein, the second acceptor material includes a fullerene structure.

[0025] Another object of the present invention is to provide an organic optoelectronic component, which comprises a first electrode, an active layer and a second electrode. The active layer comprises at least one organic composition as described above. The active layer is located between the first electrode and the second electrode, and at least one of the first electrode and the second electrode is a transparent or semi-transparent electrode.

[0026] The organic photoelectric component further comprises a first carrier transfer layer and a second carrier transfer layer. The first carrier transfer layer is disposed between the first electrode and the active layer, and the first carrier transfer layer is used to transfer carriers in the first electrode and the active layer. The second carrier transfer layer is disposed between the active layer and the second electrode, and the second carrier transfer layer is used to transfer carriers in the active layer and the second electrode.

[0027] Compared with the prior art, the organic light sensor used in the organic photoelectric component of the present invention has good light response, dark current and detection performance, and the component has better stability. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] Figure 1 A structural schematic diagram of a specific embodiment of the organic optoelectronic component of the present invention is drawn.

[0029] Figure 2 The absorption spectra of the first receptor material comparative example 1 in the thin film state and the solution state are shown.

[0030] Figure 3 The absorption spectra of the first receptor material Example 1 of the present invention in the thin film state and the solution state are shown.

[0031] Figure 4 The absorption spectra of Example 2 of the first receptor material of the present invention in the thin film state and the solution state are shown.

[0032] Figure 5 The absorption spectra of Example 3 of the first receptor material of the present invention in the thin film state and the solution state are shown.

[0033] Figure 6 The absorption spectra of Example 4 of the first receptor material of the present invention in the thin film state and the solution state are shown.

[0034] Figure 7 The absorption spectra of Example 5 of the first receptor material of the present invention in the thin film state and the solution state are shown.

[0035] Figure 8 The results of the absorption thermal stability test of the mixed films 1-1 to 6-1 of the organic composition of the present invention and the mixed film C1 of the comparative example are shown.

[0036] Fig. 9 The results of the absorption thermal stability test of the mixed films 2-2 to 5-2 of the organic composition of the present invention and the mixed film C2 of the comparative example are shown.

[0037] Fig.10 The results of the absorption thermal stability tests of the mixed films 2-3 to 3-3 of the organic compositions of the present invention and the mixed film C3 of the comparative example are shown.

[0038] Fig.11 The detection test results of the active layers of the organic optoelectronic device of the present invention, which are the mixed films 4-3 to 4-5 and the mixed film C4 of the comparative example, are shown.

[0039] Description of reference numerals:

[0040] 1: Organic optoelectronic components

[0041] 10: Substrate

[0042] 11: First electrode

[0043] 12: First carrier transfer layer

[0044] 13: Active layer

[0045] 14: Second carrier transfer layer

[0046] 15: Second electrode DETAILED DESCRIPTION

[0047] In order to make the advantages, spirit and features of the present invention easier and more clearly understood, the following will be described and discussed in detail with reference to the accompanying drawings by way of embodiments. It is worth noting that these embodiments are only representative embodiments of the present invention. However, they can be implemented in many different forms and are not limited to the embodiments described in this specification. On the contrary, the purpose of providing these embodiments is to make the disclosure of the present invention more thorough and comprehensive.

[0048] The terms used in the various embodiments disclosed in the present invention are only used for the purpose of describing specific embodiments, and are not intended to limit the various embodiments disclosed in the present invention. As used herein, the singular form also includes the plural form, unless the context clearly indicates otherwise. Unless otherwise specified, all terms used in this specification (including technical terms and scientific terms) have the same meanings as those commonly understood by ordinary technicians in the field to which the various embodiments disclosed in the present invention belong. The above terms (such as those defined in generally used dictionaries) will be interpreted as having the same meanings as the contextual meanings in the same technical field, and will not be interpreted as having idealized meanings or overly formal meanings, unless clearly defined in the various embodiments disclosed in the present invention.

[0049] In the description of this specification, the description with reference to the terms "one embodiment", "a specific embodiment", etc. means that the specific features, structures, materials or characteristics described in conjunction with the embodiment are included in at least one embodiment of the present invention. In this specification, the schematic representation of the above terms does not necessarily refer to the same embodiment. Moreover, the specific features, structures, materials or characteristics described can be combined in any one or more embodiments in a suitable manner.

[0050] definition:

[0051] As used herein, a "donor" material, a "p-type" material, refers to a semiconductor material, such as an organic semiconductor material, that has holes as the primary current or charge carriers. In certain embodiments, when a p-type semiconductor material is deposited on a substrate, it can provide more than about 10 -5 cm 2 / Vs hole mobility.

[0052] As used herein, an "acceptor" material, an "n-type" material, refers to a semiconductor material, such as an organic semiconductor material, that has electrons as the primary current or charge carrier. In certain embodiments, when an n-type semiconductor material is deposited on a substrate, it can provide more than about 10 -5 cm 2 / Vs electron mobility.

[0053] The "electron-withdrawing group" used in this article is a group or atom that has a stronger electron-withdrawing ability than hydrogen, that is, it has an electron-withdrawing inductive effect. The "electron-pushing group" used in this article is a group or atom that has a stronger electron-pushing ability than hydrogen, that is, it has an electron-pushing inductive effect. The inductive effect is the effect that the bonding electron cloud moves in a certain direction on the atomic bond due to the different polarity (electron negativity) of atoms or groups in the molecule. The electron cloud tends to move toward the group or atom with stronger electronegativity.

[0054] The “*” or “*” in the structures listed herein represents the positions of the structures available for bonding, but is not limited thereto.

[0055] As used herein, "mobility" refers to a measure of the rate at which charge carriers, such as holes (positive charge) in a p-type semiconductor material and electrons (negative charge) in an n-type semiconductor material, move through a material under the influence of an electric field. This parameter depends on the device architecture and can be measured using field effect devices or space charge limited current.

[0056] As used herein, "polymer" refers to a very large molecule consisting of thousands or more covalently bonded atoms. A polymer is composed of many repeating units, i.e. monomers (composed of one or more atoms) bonded together by covalent bonds. From a physical property point of view, the number of repeating units should be so large that adding more repeating units will not significantly change the physical properties. Polymers are divided into copolymers and homopolymers. Homopolymers are polymerized from only one monomer. Copolymers are polymers formed by the polymerization of two or more monomers. Copolymers are divided into alternating copolymers, random copolymers, block copolymers, and graft copolymers.

[0057] As used herein, a component (eg, a thin film layer) may be considered "photoactive" if it includes one or more compounds that can absorb photons to generate excitons for generating photocurrent.

[0058] As used herein, "solution processing" refers to processes in which compounds (e.g., polymers), materials or compositions can be used in solution-state processes, such as spin coating, printing (e.g., inkjet printing, gravure printing, lithography, etc.), spraying, electrospraying, drop casting, dip coating and doctor blade coating.

[0059] As used herein, "annealing" refers to a post-deposition heat treatment of a semi-crystalline polymer film for a certain duration in an ambient or under reduced pressure or increased pressure, and "annealing temperature" refers to a temperature at which the polymer film or a mixed film of the polymer and other molecules can undergo small-scale molecular motion and rearrangement during the annealing process. Without being bound by any particular theory, it is said that annealing may lead to an increase in crystallinity in the polymer film, an increase in the material carrier mobility of the polymer film or a mixed film of the polymer and other molecules, and the formation of molecular interactive arrangements to achieve the effect of independent transfer paths for effective electrons and holes.

[0060] The dark current (J d or J dark ), also known as no-light current, refers to the current flowing in the photovoltaic component in the absence of light.

[0061] The responsivity (R) and detectivity (D) used in this article are calculated by measuring the dark current and external quantum efficiency (EQE) of the organic light sensing element using the following formula:

[0062]

[0063] Where λ is the wavelength and q is the elementary charge (1.602×10 -19 Coulombs, h is Planck's constant (6.626×10 -34 m 2 kg / s, c is the speed of light (3×10 8 m / sec), J d is the dark current.

[0064] In one embodiment, an organic composition of the present invention comprises at least one donor material and at least one acceptor material. The donor material comprises at least one organic conjugated polymer or organic conjugated small molecule. The acceptor material comprises a first acceptor material, and the first acceptor material has a structure as shown in Formula 1:

[0065]

[0066] wherein the nucleus is a phenyl group; Ar1 ​​is a five-membered or six-membered heterocyclic ring containing at least one heteroatom, and the heteroatom is independently selected from at least one of S, N, O and Se; R1, R2, R3 and R4 are independently selected from the following groups and one of their derivatives: C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 ester, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 silylaryl, C1-C30 silylheteroaryl, C1-C30 alkoxyaryl C1-C30 alkyl, C1-C30 alkoxy heteroaryl, C1-C30 alkylthio aryl, C1-C30 alkylthio heteroaryl, C1-C30 halogenated alkyl aryl, C1-C30 halogenated alkyl heteroaryl, C2-C30 ester aryl and C2-C30 ester heteroaryl; and R5, R6, R7 and R8 are independently selected from the following groups and one of their derivatives: C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 halogenated alkyl, halogen, hydrogen atom and cyano, wherein R5, R6, R7 and R8 are not hydrogen atoms at the same time. This structure has good optical properties and appropriate energy levels, and can be used with suitable p-type materials to make organic optoelectronic devices. Among them, this structure has the following characteristics: 1. The terminal naphthalene ring group can effectively improve the stability of the material; 2. Replacing R5, R6, R7 and R8 with at least one substituent can adjust the material energy level to facilitate the matching of different p-type materials; 3. The aforementioned substituents can also effectively change the intermolecular forces and improve the material arrangement, thereby improving the performance of the component.

[0067] In practical applications, Ar1 is independently selected from one of the following structures:

[0068]

[0069] Among them, R9 and R 10 is independently selected from the following groups and one of their derivatives: halogen, hydrogen atom, cyano, C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 ester, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 silylaryl, C1-C30 silylheteroaryl, C1-C30 alkoxyaryl, C1-C30 alkoxyheteroaryl, C1-C30 alkylthioaryl, C1-C30 alkylthioheteroaryl, C1-C30 haloalkylaryl, C1-C30 haloalkylheteroaryl, C2-C30 esteraryl and C2-C30 esterarylheteroaryl, wherein R9 and R 10 It can be two separate groups or connected to each other by a single bond.

[0070] Wherein, Ar1 is further preferably selected from one of the following structures:

[0071]

[0072] Among them, R9 and R 10 The definition of is the same as above.

[0073] In practical applications, R1 and R2 are further independently preferably selected from C1-C30 alkyl or C1-C30 alkylaryl. R3 and R4 are further independently preferably selected from one of the following groups and their derivatives: C1-C30 alkyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 alkoxyaryl, C1-C30 alkoxyheteroaryl, C1-C30 alkylthioaryl, C1-C30 alkylthioheteroaryl, C1-C30 halogenated alkylaryl, C1-C30 halogenated alkylheteroaryl. R5, R6, R7 and R8 are further independently preferably selected from the following groups and their derivatives: C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, halogen, hydrogen atom and cyano, wherein R5, R6, R7 and R8 are not hydrogen atoms at the same time.

[0074] In practical applications, R1 and R2 are more preferably independently selected from C1-C30 alkyl groups. R3 and R4 are more preferably independently selected from one of the following groups and their derivatives: C1-C30 alkyl groups, C1-C30 alkoxy groups, C1-C30 alkylaryl groups, and C1-C30 alkylheteroaryl groups. R5, R6, R7, and R8 are more preferably independently selected from one of the following groups and their derivatives: halogen, hydrogen atom, and cyano group, wherein R5, R6, R7, and R8 are not hydrogen atoms at the same time.

[0075] Specifically, the first receptor material may include the following embodiments 1 to 22:

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084] It should be understood that the above embodiments are representative examples for those skilled in the art to more clearly understand the structural composition of the present invention, and are not limited thereto.

[0085] In one embodiment, the donor material is further selected from at least one organic conjugated polymer. In practical applications, the organic conjugated polymer includes one of the following structures:

[0086]

[0087] Wherein, Ar2, Ar3, Ar4 and Ar5 are monocyclic or polycyclic structures respectively containing 4 to 30 ring atoms; n is the number of molecules, and n is a positive integer from 1 to 1000; and x and y are mole fractions, where 0 < x < 1, 0 < y < 1 and x + y = 1. In a preferred embodiment, at least one of the ring atoms contained in Ar2, Ar3, Ar4 and Ar5 is a heteroatom, and the heteroatom is independently selected from at least one of S, O, Se, N, F, Cl and Si.

[0088] In one embodiment, Ar2 and Ar4 are independently selected from one of the following structures:

[0089]

[0090]

[0091] Wherein A1, A2, A3 and A4 are independently selected from one of O, S, Se and N-R, and R is selected from one of the following groups and their derivatives: alkyl with 1 to 30 carbon atoms, silyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, alkylthio with 1 to 30 carbon atoms, haloalkyl with 1 to 30 carbon atoms, ester group with 2 to 30 carbon atoms, alkylaryl with 1 to 30 carbon atoms, alkylheteroaryl with 1 to 30 carbon atoms, silylaryl with 1 to 30 carbon atoms, silylheteroaryl with 1 to 30 carbon atoms, alkoxyaryl with 1 to 30 carbon atoms, alkoxyheteroaryl with 1 to 30 carbon atoms, alkylthioaryl with 1 to 30 carbon atoms, alkylthioheteroaryl with 1 to 30 carbon atoms, haloalkylaryl with 1 to 30 carbon atoms, haloalkylheteroaryl with 1 to 30 carbon atoms, ester group aryl with 2 to 30 carbon atoms and ester group heteroaryl with 2 to 30 carbon atoms; and R 11 , R 12 , R 13 , R 14 , R 15 , and R 16Independently selected from the following groups and one of their derivatives: hydrogen atom, halogen, cyano, C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 ester, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 silylaryl, C1-C30 silylheteroaryl, C1-C30 alkoxyaryl, C1-C30 alkoxyheteroaryl, C1-C30 alkylthioaryl, C1-C30 alkylthioheteroaryl, C1-C30 haloalkylaryl, C1-C30 haloalkylheteroaryl, C1-C30 esteraryl and C2-C30 esterarylheteroaryl.

[0092] In one embodiment, Ar3 and Ar5 are independently selected from one of the following structures:

[0093]

[0094]

[0095] wherein A5, A6, A7 and A8 are independently selected from one of O, S, Se and NR, R is selected from one of the following groups and derivatives thereof: C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 ester, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 silylaryl, C1-C30 silylheteroaryl, C1-C30 alkoxyaryl, C1-C30 alkoxyheteroaryl, C1-C30 alkylthioaryl, C1-C30 alkylthioheteroaryl, C1-C30 haloalkylaryl, C1-C30 haloalkylheteroaryl, C2-C30 esteraryl and C2-C30 esterarylheteroaryl; and R 17 , R 18 , R 19 , R 20 , R 21 and R 22 Independently selected from the following groups and one of their derivatives: hydrogen atom, halogen, cyano, C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 ester, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 silylaryl, C1-C30 silylheteroaryl, C1-C30 alkoxyaryl, C1-C30 alkoxyheteroaryl, C1-C30 alkylthioaryl, C1-C30 alkylthioheteroaryl, C1-C30 haloalkylaryl, C1-C30 haloalkylheteroaryl, C1-C30 esteraryl and C2-C30 esterarylheteroaryl.

[0096] Specifically, when the donor material is an organic conjugated polymer, it may include the following donors 1 to 36:

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] It should be understood that the above embodiments are representative examples to help those skilled in the art to more clearly understand the structural composition of the present invention, and are not limited thereto.

[0106] In one embodiment, the receptor material further comprises a second receptor material, and the second receptor material is an organic conjugated polymer or an organic conjugated small molecule. In practical applications, the second receptor material comprises a fullerene structure. Specifically, the fullerene structure may comprise the following embodiments of fullerene 1 to fullerene 10:

[0107]

[0108]

[0109] It should be understood that the above embodiments are representative examples to help those skilled in the art to more clearly understand the structural composition of the present invention, and are not limited thereto.

[0110] See also Figure 1 , Figure 1 A schematic diagram of the structure of an embodiment of an organic optoelectronic component 1 of the present invention is drawn. Figure 1As shown, in an embodiment, the present invention provides an organic photoelectric component 1, which includes a first electrode 11, a second electrode 15 and an active layer 13. The active layer 13 is located between the first electrode 11 and the second electrode 15. In one embodiment, the active layer 13 includes the aforementioned organic composition including a structure of formula 1. The organic photoelectric component 1 can be a stacked structure, further including a first carrier transfer layer 12 and a second carrier transfer layer 14, and is stacked with a substrate 10, a first electrode 11 (transparent or semi-transparent electrode), a first carrier transfer layer 12, an active layer 13, a second carrier transfer layer 14 and a second electrode 15 in sequence. The first carrier transfer layer 12 is used to transfer carriers in the first electrode 11 and the active layer 13, and the second carrier transfer layer 14 is used to transfer carriers in the active layer 13 and the second electrode 15. In detail, the first carrier transfer layer 12 is one of an electron transport layer and a hole transport layer, and the second carrier transfer layer 14 is the other. Specifically, when the first carrier transport layer 12 is an electron transport layer, the second carrier transport layer 14 is a hole transport layer, which is a reverse stack structure; when the first carrier transport layer 12 is a hole transport layer, the second carrier transport layer 14 is an electron transport layer, which is a regular stack structure. In practice, the organic optoelectronic component 1 may include an organic photovoltaic component, an organic light sensing component, and an organic light emitting diode.

[0111] In order to more clearly illustrate the organic composition of the present invention, the following experiments are conducted using Comparative Example 1 and the aforementioned Examples 1 to 5 of the present invention to illustrate the difference in efficacy, and further use it as the first receptor material to prepare an active layer and an organic optoelectronic component for material testing and component testing.

[0112] For the optical physical property quality measurement part of material testing and component testing, the UV absorption spectrum measurement instrument model is Hitachi UH5700, and the oxidation potential is measured using cyclic voltammetry with CH Instrument 611E.

[0113] First receptor material: Synthesis of Example 1:

[0114]

[0115] M1 (150 mg, 0.141 mmol), M2 (118 mg, 0.422 mmol) and chloroform (CF, 7.2 mL) were placed in a 100 ml three-necked flask and stirred with a magnet. Pyridine (0.08 mL) was added and the temperature was raised to 60°C for reaction for 6 hours. Methanol was added to precipitate the product and the solid was collected by vacuum filtration. The crude product was purified by silica gel column chromatography (eluting solvent: heptane / chloroform = 1 / 1) to obtain the product Example 1 as a blue-black solid (140 mg, yield 62%). 1H NMR (600MHz, CDCl3): δ9.27(s,2H),9.14(s,2H),8.34(s,2H),7.87-7.80(m,4H),4.80(d,J=4.2Hz,4H),3.27(t,J=9.0 Hz,4H),2.12(br,2H),1.92-1.88(m,4H),1.52-0.87(m,48H),0.78-0.77(m,6H),0.77-0.69(m,6H),0.68-0.67(m,6H).

[0116] Synthesis of Example 2:

[0117]

[0118]

[0119] M3 (357 mg, 0.275 mmol), M2 (308 mg, 1.099 mmol) and chloroform (CF, 10 mL) were placed in a 100 mL three-necked flask and stirred with a magnet. Pyridine (0.2 mL) was added and the temperature was raised to 60°C for 4 hours. Methanol was added to precipitate the product and the solid was collected by vacuum filtration. The crude product was purified by silica gel column chromatography (eluting solvent: heptane / chloroform = 1 / 1) to obtain the product Example 2 as a blue-black solid (410 mg, yield 82%). 1 H NMR (500MHz, CDCl3): δ9.26 (s, 2H), 9.14 (s, 2H), 8.32 (m, 2H), 7.87-7.78 (m, 4H), 4.74 (d, J = 12Hz, 4H), 3.26 (t ,J=7.5Hz,4H),2.16(br,2H),1.90(t,J=7.5Hz,4H),1.57-0.85(m,86H),0.79-0.76(m,6H),0.71-0.69(m,6H).

[0120] Synthesis of Example 3:

[0121] Synthetic M6:

[0122]

[0123] Take M4 (2.0 g, 1.67 mmol) and put it into a 100 ml three-necked flask, add anhydrous tetrahydrofuran (THF, 40 mL). Add lithium aluminum hydride (LiAlH4, 0.64 g, 16.7 mmol) under an ice bath. After the reaction stops bubbling, return to room temperature, react for 2 hours, and slowly drip deionized water to stop the reaction. Extract with heptane / water (Heptane / H2O), collect the organic layer and add magnesium sulfate (MgSO4) to remove water. After removing the solvent, the intermediate product is obtained. The intermediate product is placed in a 100 ml three-necked flask, dissolved with acetic acid (55 mL), and then M5 (0.78 g, 1.52 mmol) is weighed in, and the temperature is raised to 120 ° C for 2 hours. After the reaction is completed, the reaction is cooled to room temperature. Extract with dichloromethane / water (DCM / H2O) three times. Collect the organic layer, add magnesium sulfate (MgSO4) to remove water, and remove the solvent. The crude product was purified by silica gel column chromatography (eluting solvent: heptane) to obtain the product M6 (2.0 g, yield 86%) as a red oil. 1 H NMR (600MHz, CDCl3): δ7.33 (s, 2H), 7.02 (s, 2H), 4.52 (d, J = 7.8Hz, 4H), 2.85 -2.90(m,8H),1.81-1.92(m,6H),0.76-1.57(m,122H),0.70(t,J=6.6Hz,6H).

[0124] Synthetic M7:

[0125]

[0126] Phosphorus oxychloride (POCl3, 0.26 mL, 2.75 mmol) and dimethylformamide (DMF, 1.78 mL, 22.9 mmol) were mixed in a 100 mL double-necked flask in an ice bath and stirred with a magnet for 30 minutes to form a Vilsmeier reagent. Prepare another 100 mL double-necked flask, weigh M6 (756 mg, 0.46 mmol), add dichloroethane (DCE, 30 mL) and stir with a magnet. Then, add the Vilsmeier reagent, heat to 70°C and react for 18 hours. Cool the reaction to room temperature and extract three times with dichloromethane / water (DCM / H2O). Collect the organic layer, add magnesium sulfate (MgSO4) to remove water, and remove the solvent. The crude product was purified by silica gel column chromatography (eluting solvent: heptane / chloroform = 1 / 1) to obtain the product orange-red solid M7 (437 mg, yield 56%). 1H NMR (600MHz, CDCl3): δ10.15(s,2H),7.34(s,2H),4.66(d,J=7.8Hz,4H),3.23(t,J=7.8Hz,4H),2.85-2. 92(m,4H),2.09(m,2H),1.95(m,4H)1.80(d,J=12.6Hz,2H),0.76-1.43(m,120H),0.69(t,J=7.2Hz,6H).

[0127] Synthesis Example 3:

[0128]

[0129] M7 (200 mg, 0.12 mmol), M2 (98.7 mg, 0.36 mmol) and chloroform (CF, 6 mL) were placed in a 100 ml three-necked flask and stirred with a magnet. Pyridine (0.1 mL) was added and the temperature was raised to 60°C for 4 hours. Methanol was added to precipitate the product and the solid was collected by vacuum filtration. The crude product was chromatographed on a silica gel column (eluting solvent: heptane / chloroform = 1 / 2) to obtain the product Example 3 as a blue-black solid (190 mg, yield 73%). 1 H NMR (600MHz, CDCl3): δ9.29(s,2H),9.15(s,2H),8.32(s,2H),7.79-7.88(m,4H),7.43(s,2H),7.04(d,J=3.6Hz,2H),4.81(d,J=7.8Hz,4H),3.3 1(t,J=7.8Hz,4H),2.86-2.91(m,4H),2.18(m,2H),1.92(m,4H),1.72(m ,2H),1.42-0.74(m,112H),0.75(t,J=7.2Hz,6H),0.71(t,J=6.9Hz,6H).

[0130] Synthesis of Example 4:

[0131] Synthetic M10:

[0132]

[0133] Take M8 (2.0 g, 9.1 mmol) and M9 (4.3 g, 9.1 mmol) and put them into a 100 ml three-necked flask, add toluene (Toluene, 65 mL) and stir with a magnet. Deoxygenate at room temperature for 30 minutes. Add tri(dibenzylideneacetone)dipalladium (Pd2dba3, 333 mg, 0.36 mmol) and tri(o-methylphenyl)phosphine (P(o-tolyl)3, 443 mg, 1.45 mmol), heat to 80°C and react for 18 hours. Cool the reaction to room temperature. The crude product is purified by silica gel column chromatography (eluting solvent is heptane) to obtain the product oil M10 (3.6 g, 88%). 1 H NMR (600MHz, CDCl3): δ7.45(dd,J=5.1Hz,J=1.5Hz,1H),7.40(d,J=1.8Hz,1H),7.29(d,J=5.4Hz,1H),7.22(d,J =3.6Hz,1H),6.74(d,J=3.6Hz,1H),2.77(d,J=6.0Hz,2H),1.66(m,1H),1.32-1.27(m,24H),0.90-0.86(m,6H).

[0134] Synthetic M13:

[0135]

[0136] Take a 250 ml three-necked flask, weigh M10 (3.07 g, 6.87 mmol), add anhydrous tetrahydrofuran (THF, 60 mL) and place in a -60 ° C ice bath with a magnet. Slowly add lithium diisopropylamide (LDA, 2.0 M, 3.44 mL, 6.87 mmol) in an ice bath and react at -60 ° C for 30 minutes. Then, slowly add trimethyltin chloride (1.37 g, 6.87 mmol, completely dissolved in 5 mL THF) at -60 ° C, and return the reaction to room temperature for 30 minutes. Slowly add methanol (MeOH) to terminate the reaction until no more bubbling. Extract three times with heptane / water (Heptane / H2O). Collect the organic layer and add magnesium sulfate (MgSO4) to remove water to obtain the crude product M11, which is directly carried out to the next step without additional purification. The crude products M11 and M12 (0.82 g, 2.14 mmol) were placed in a 250 ml three-necked flask, and toluene (Toluene, 40 mL) was added and stirred with a magnet. Deoxygenation was carried out at room temperature for 30 minutes. Tris(dibenzylideneacetone)dipalladium (Pd2dba3, 34 mg, 0.038 mmol) and tris(o-methylphenyl)phosphine (P(o-tolyl)3, 46 mg, 0.152 mmol) were added, and the temperature was raised to 80°C for 4 hours. The reaction was cooled to room temperature, and methanol (MeOH, 40 mL) was added to precipitate the product. The product M13 (1.94 g, yield 81%) was obtained by vacuum filtration as a red solid. 1 H NMR (600MHz, CDCl3): δ7.70(s,2H),7.56(s,2H),7.24(d,J=3.0Hz,2H),6.78(d,J=3. 6Hz, 2H), 2.80 (d, J = 7.2Hz, 4H), 1.67 (m, 2H), 1.32-1.27 (m, 48H), 0.89-0.85 (m, 12H).

[0137] Synthetic M14:

[0138]

[0139] M13 (1.9 g, 1.7 mmol) and triphenylphosphine (PPh3, 4.46 g, 17 mmol) were placed in a 250 ml three-necked flask, and o-dichlorobenzene (o-DCB, 48 mL) was added. Deoxygenate with argon at room temperature for 30 minutes. Heat to 180°C and reflux for 4.5 hours. After the reaction is completed, remove the casserole and return to room temperature, and distill off o-DCB. The product was precipitated with tetrahydrofuran (THF, 15 mL) and methanol (MeOH, 40 mL). The solid was collected by vacuum filtration to obtain 1.39 g of crude product. The next step was carried out directly without additional purification. The crude product (1.39 g, 1.32 mmol) and potassium hydroxide (KOH, 0.59 g, 10.6 mmol) were placed in a 100 ml three-necked flask. Dimethyl sulfoxide (DMSO, 13.9 mL) and toluene (Toluene, 9.5 mL) were added and stirred at room temperature for 30 minutes. 1-iodo-2-hexyldecane (2.8 g, 7.9 mmol) was added, and the temperature was raised to 80°C for 18 hours. The reaction was cooled to room temperature. The mixture was extracted three times with ethyl acetate / water (EA / H2O), and the organic layer was collected and magnesium sulfate (MgSO4) was added to remove water, and the solvent was removed. The crude product was purified by silica gel column chromatography (eluent: heptane / dichloromethane (Heptane / DCM) = 3 / 1)) to obtain the product M14 (1.23 g, yield 86%) as an orange-red oil. 1 H NMR (600MHz, CDCl3): δ7.40 (s, 2H), 7.38 (d, J = 3.6Hz, 2H), 6.81 (d, J = 3.6Hz 2H), 4.62 (d, J = 7.8Hz, 4H), 2.81 (d, J = 6.6Hz 4H),2.09-2.07(m,2H),1.69(m,2H),1.26-0.83(m,102H),0.83-0.78(m,12H),0.77-0.67(m,6H).

[0140] Synthetic M15:

[0141]

[0142] Phosphorus oxychloride (POCl3, 0.79 mL, 4.92 mmol) and dimethylformamide (DMF, 3.17 mL, 41.0 mmol) were mixed in a 100 mL double-necked flask in an ice bath and stirred with a magnet for 30 minutes to form a Vilsmeier reagent. Prepare another 100 mL double-necked flask, weigh M14 (1.23 g, 0.82 mmol), add dichloroethane (DCE, 50 mL) and stir with a magnet. Then, add the Vilsmeier reagent, heat to 70°C and react for 3 hours. Cool the reaction to room temperature and extract three times with dichloromethane / water (DCM / H2O). Collect the organic layer, add magnesium sulfate (MgSO4) to remove water, and remove the solvent. The crude product was purified by silica gel column chromatography (eluting solvent: heptane / chloroform = 1 / 1) to obtain the product M15 (1.01 g, yield 79%) as an orange-red oil. 1 H NMR (600MHz, CDCl3): δ10.26(s,2H),7.44(d,J=3.6Hz,2H),6.93(d,J=3.6Hz,2H),4.65(d,J=7.8Hz,4H),2. 88(d,J=6.6Hz,4H),2.05(m,2H),1.75(m,2H),1.43-0.86(m,102H),0.80-0.78(m,12H),0.70-0.07(m,6H).

[0143] Synthesis Example 4:

[0144]

[0145] M15 (300 mg, 0.2 mmol), M2 (168 mg, 0.6 mmol) and chloroform (CF, 9 mL) were placed in a 100 ml three-necked flask and stirred with a magnet. Pyridine (0.15 mL) was added and the temperature was raised to 60°C for 3 hours. Methanol was added to terminate the reaction and the product was precipitated. The solid was collected by vacuum filtration. The crude product was purified by silica gel column chromatography (eluting solvent: heptane / chloroform = 1 / 2) to obtain the product Example 4 as a blue-black solid (180 mg, yield 43%). 1H NMR (600MHz, CDCl3): δ9.24(s,2H),9.10(s,2H),8.33(s,2H),7.87-7.84(m,2H),7.83-7.80(m,2H),7.41(d,J=3.6Hz 2H),7.04(d,J=3.6Hz,2H),4.79(d,J=7.2Hz,4H),2.93(d,J=6.0Hz,4H),2.16-2.1 5(m,2H),1.78(m,2H),1.53-0.85(m,102H),0.76-0.75(m,9H),0.73-0.70(m,9H).

[0146] Synthesis of Example 5:

[0147] Synthetic M18:

[0148]

[0149] Take M16 (4.2g, 15.90mmol), M17 (2.7g, 39.74mmol), piperidine (4.2mL), acetic acid (12.6mL) and dimethylformamide (DMF, 92.4mL) and put them into a 250ml double-necked flask and stir with a magnet. React at room temperature for 18 hours. Add 1M hydrochloric acid (HCl, 252mL) and stir at room temperature for 1 hour. Collect the solid by vacuum filtration and rinse with water and heptane. Dissolve the crude product in ethanol (EtOH, 40mL) and slowly add water (200mL) to precipitate the product. Collect the solid by vacuum filtration to obtain the product, a light brown solid M18 (4.9g, yield 99%). 1 H NMR confirmed that the mixture ratio was approximately 1:0.8. 1 H NMR (600MHz, CDCl3): δ9.30(s,1H),9.25(s,1H),8.60(s,1H),8.55(s,1H),8.45(s,1H),8. 41(s,1H),8.29(d,J=10.2Hz,1H),8.25(d,J=10.2Hz,1H),7.95-7.94(m,2H),3.90(s,4H).

[0150] Synthesis Example 5:

[0151]

[0152]

[0153] M19 (300 mg, 0.240 mmol), M18 (374 mg, 1.198 mmol) and chloroform (CF, 9 mL) were placed in a 100 ml three-necked flask and stirred with a magnet. Pyridine (0.25 mL) was added and the temperature was raised to 60°C for 6 hours. Methanol was added to terminate the reaction and the product was precipitated. The solid was collected by vacuum filtration. The crude product was purified by silica gel column chromatography (eluting solvent: heptane / chloroform = 1 / 1) to obtain the product Example 5 as a blue-black solid (340 mg, yield 77%). 1 H NMR confirmed that the mixture ratio was approximately 1:0.8. 1 H NMR (600MHz, CDCl3): δ9.32(s,2H),9.31(s,4H),9.29(s,2H),8.48(s,2H),8.4 5(s,2H),8.41(s,2H),8.35(s,2H),8.24(d,J=9.0Hz,2H),8.19(d,J=9.0Hz,2H) ,7.88-7.87(m,4H),4.80(d,J=7.8Hz,8H),3.29(t,J=7.5,8H),2.16(br,4H),1 .90-1.89(m,8H),1.55-0.81(m,172H),0.79-0.76(m,12H),0.71-0.69(m,12H).

[0154] Synthesis of Comparative Example 1:

[0155]

[0156]

[0157] M19 (300 mg, 0.240 mmol), M20 (118 mg, 0.422 mmol) and chloroform (CF, 9.0 mL) were placed in a 100 ml three-necked flask and stirred with a magnet. Pyridine (0.15 mL) was added and the temperature was raised to 60°C for 18 hours. Methanol was added to precipitate the product and the solid was collected by vacuum filtration. The crude product was purified by silica gel column chromatography (eluting solvent: heptane / chloroform = 2 / 1) to obtain the product of blue-black solid Comparative Example 1 (362 mg, yield 90%). 1H NMR (500MHz, CDCl3): δ9.16(s,2H),8.57-8.57(m,2H),7.71-7.68(m,2H),4.76(d,J=7.5Hz,4H),3.23(t,J= 8.0Hz,4H),2.13-2.10(m,2H),1.91-1.85(m,4H),1.56-1.49(m,4H),1.39-0.77(m,88H),0.69-0.67(m,6H).

[0158] The material tests of the first receptor material Examples 1 to 5 and Comparative Example 1 include material optical property and electrochemical property tests:

[0159] See also Figures 2 to 7 And Table 1. Figure 2 The absorption spectra of the first receptor material comparative example 1 in the thin film state and the solution state are shown. Figure 3 The absorption spectra of the first receptor material Example 1 of the present invention in the thin film state and the solution state are shown. Figure 4 The absorption spectra of the first receptor material Example 2 of the present invention in the thin film state and the solution state are shown. Figure 5 The absorption spectra of the first receptor material Example 3 of the present invention in the thin film state and the solution state are shown. Figure 6 The absorption spectra of the first receptor material Example 4 of the present invention in the thin film state and the solution state are shown. Figure 7 The absorption spectra of the first receptor material Example 5 of the present invention in the thin film state and the solution state are shown in Table 1. The material tests of the first receptor material Examples 1 to 5 and Comparative Example 1 (including Figures 2 to 7 data results).

[0160] Table 1: Material tests of first receptor material Examples 1 to 5 and Comparative Example 1 (including Figures 2 to 7 Data results)

[0161]

[0162]

[0163] like Figures 2 to 7 As shown in Table 1, the maximum absorption value of the thin film state of Examples 1 to 5 falls within 833-872nm, and the initial absorption value falls within 892-958nm. From the thin film state absorption spectrum, it can be seen that the film state has good absorption properties in the range of 300-900nm, and the extinction coefficient falls within 1.72-2.02x10 5 cm -1 M -1The maximum absorption value of the thin film of Comparative Example 1 is 822nm, and the initial absorption value is at 918nm. From the absorption spectrum of the thin film, it can be seen that it has good absorption properties in the range of 300-900nm, and the extinction coefficient is 1.86x10 5 cm -1 M -1 The application range of the above-mentioned embodiments 1 to 5 and comparative example 1 can all be from visible light to infrared light.

[0164] Active layer organic composition mixed material absorption thermal stability performance test:

[0165] See also Figures 8 to 10 And Table 2. Figure 8 The results of the absorption thermal stability test of the mixed films 1-1 to 6-1 of the organic composition of the present invention and the mixed film C1 of the comparative example are shown. Fig. 9 The results of the absorption thermal stability test of the mixed films 2-2 to 5-2 of the organic composition of the present invention and the mixed film C2 of the comparative example are shown. Fig.10 The results of the absorption thermal stability test of the mixed films 2-3 to 3-3 of the organic composition of the present invention and the mixed film C3 of the comparative example are shown in Table 2. Figures 8 to 10 The mixed material absorption thermal stability performance test.

[0166] Table 2: Figures 8 to 10 Thermal stability performance test of mixed materials

[0167]

[0168] Under the atmosphere, the first acceptor material embodiment and the comparative example are combined with different donor materials (p-type materials) or further added with the fullerene material of the second acceptor material to form an organic composition. The aforementioned organic composition is made into a mixed film, and the absorption peak (maximum value between 750 and 950 nm) of the acceptor material (n-type material) is paid attention to. Figures 8 to 10 As shown in Table 2, comparative example 1 is respectively combined with donor 31, donor 24 and donor 9 to form mixed film C1, mixed film C2 and mixed film C3. After the mixed film C1, mixed film C2 and mixed film C3 are gradually heated and calcined, the initial absorption peak is 100%, and the relative intensity of the absorption spectrum after heating is only 52-75%. Relatively speaking, the three different p-type materials are combined in examples 1-5, and the intensity is still maintained at 91-146% after the gradual heating and calcination. In addition, ternary mixing is also carried out to form mixed film 6-1 and mixed film 3-3, and the intensity is still maintained at 117-118% after the gradual heating and calcination. It can be seen that examples 1-5 of the present invention still maintain good thermal stability after being combined with p-type materials and fullerene materials, while comparative example 1 cannot maintain good thermal stability.

[0169] Preparation and performance testing of organic light sensing components of organic optoelectronic components:

[0170] Pre-patterned indium tin oxide (ITO) coated glass with a sheet resistance of ~15Ω / sq was used as the substrate. Ultrasonication was sequentially performed in deionized water containing soap, deionized water, acetone, and isopropanol, with cleaning for 15 minutes in each step. The washed substrate was further treated with a UV-ozone cleaner for 15 minutes. A top coating of aluminum doped zinc oxide nanoparticles (AZO) was spin-coated on the ITO substrate at a rotation rate of 2000 rpm for 40 seconds, and then baked at 120°C in air for 5 minutes to form an electron transporting layer (ETL). Active layer solution (donor material: acceptor material weight ratio of 1:1~2). The concentration of the donor material was 20 mg / mL. The donor material and the acceptor material were as described above. After the active layer material was completely dissolved, it was filtered with a PTFE filter membrane (pore size 0.45~1.2 mm), and the active layer solution was heated for 1 hour. Then the active layer material is cooled to room temperature for spin coating, and the film thickness is controlled by the coating speed to be around 100-800nm. Finally, the film formed by the coated active layer material is thermally annealed at 100℃ for 5 minutes and then transferred to the thermal evaporation machine. -6 A thin layer (8 nm) of molybdenum trioxide (MoO3) was deposited as a hole transporting layer (HTL) under a vacuum of 1000 Torr. TM The 2400 source meter instrument records the dark current (J) in the absence of light. dark The external quantum efficiency (EQE) is measured using an external quantum efficiency meter with a measurement range of 300 to 1000 nm (bias voltage is 0 to -8 V), and silicon (300 to 1100 nm) is used for light source calibration.

[0171] It should be noted that in practical applications, the first electrode preferably has good light transmittance. The first electrode is often made of a transparent conductive material, preferably one of the following conductive material groups: indium oxide, tin oxide, fluorine-doped tin oxide derivatives (Florine Doped Tin Oxide, FTO), or composite metal oxides, such as indium tin oxide (Indium Tin Oxide, ITO) and indium zinc oxide (Indium Zinc Oxide, IZO). The material of the second electrode is a conductive metal, preferably silver or aluminum, more preferably silver. Suitable and preferred materials for the electron transport layer include, but are not limited to, metal oxides, such as ZnO x , aluminum-doped ZnO (AZO), TiO x or nanoparticles thereof, salts (e.g., LiF, NaF, CsF, Cs2CO3), amines (e.g., primary amines, secondary amines, or tertiary amines), conjugated polymer electrolytes (e.g., polyethyleneimine), conjugated polymers (e.g., poly[3-(6-trimethylammoniohexyl)thiophene], poly(9,9)-bis(2-ethylhexyl-fluorene)-b-poly[3-(6-trimethylammoniohexyl)thiophene], or poly[(9,9-bis(3′-(N,N-dimethylamino)propyl)-2,7-fluorene)-alt-2,7-(9,9-dioctylfluorene)]), and organic compounds (e.g., tris(8-quinolyl)-aluminum(III) (Al q3 ), 4,7-diphenyl-1,10-phenanthroline), or a combination of one or more of the above substances. Suitable and preferred materials for the hole transport layer include, but are not limited to, metal oxides, such as ZTO (Zinc Tin Oxide), MoO x , WO x 、NiO x SnO x Or its nanoparticles, containing metal salts, such as copper sulfide, cuprous thiocyanate, copper iodide, copper indium sulfide, lead sulfide, cobalt acetate, tungsten disulfide, etc., conjugated polymer electrolytes, such as PEDOT:PSS, polymer acids, such as polyacrylates, conjugated polymers, such as polytriarylamine (PTAA), insulating polymers, such as Nafion films, polyethyleneimine or polystyrene sulfonate, organic compounds, such as N,N'-diphenyl-N,N'-bis(1-naphthyl)(1,1'-biphenyl)-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), or a combination of one or more of the above materials.

[0172] See also Fig.11 And Table 3, Fig.11The detection test results of the active layer of the organic optoelectronic device of the present invention are the mixed films 4-3 to 4-5 and the comparative mixed film C4. Table 3 shows Fig.11 The test data results.

[0173] Table 3: Fig.11 Test data results

[0174]

[0175] like Fig.11 As shown in Table 3, in the component test, donor 21 was used as the donor material, and active layer mixed film C4, mixed film 4-3, mixed film 4-4 and mixed film 4-5 were formed in combination with comparative example 1 and examples 3 to 5. 850nm was used as the observation wavelength to explore the initial performance of the component and the performance of the component after annealing at 160℃. In terms of initial component performance, the performance of the four active layers was not much different. After annealing at 160℃, in the trend of dark current density at -8V, the dark current density of mixed film C4 increased from 7.5x10 -9 A / cm 2 Gradually increase to 2.3x10 -8 A / cm 2 . The dark current density of hybrid film 4-3, hybrid film 4-4 and hybrid film 4-5 all decreased to varying degrees. It should be understood that the decrease in dark current density is very significant for the efficiency improvement of organic light sensors. It is worth noting that in terms of EQE performance at -8V, the hybrid film C4 declined from 64.9% to 14.3%. The hybrid film 4-3 was almost maintained, only from 64.2% to 64.8%. The hybrid film 4-4 declined slightly from 64.7% to 30.9%. Although the hybrid film 4-5 also declined from 65.5% to 21.1%, it was still higher than the 14.3% of the hybrid film C4. In terms of the detection maintenance rate of the active layer at -8V, the hybrid film C4 was only 15.1%, the hybrid film 4-3 was 175.8%, the hybrid film 4-4 was 117.6%, and the hybrid film 4-5 was 54.9%. Overall, the overall detection rate maintenance rate of the active layer of Examples 3 to 5 at -8V is at least 3.6 times higher than that of the active layer of the comparative example, and can be as high as 11.6 times higher.

[0176] Based on the above experimental results, the organic composition of Formula 1 and the organic optoelectronic device using the organic composition of the present invention have good photoresponse, dark current and detection performance when used as an organic light sensor, and the device has good stability.

[0177] According to the detailed description of the above specific embodiments, it is hoped that the features and spirit of the present invention can be more clearly described, and the scope of the present invention is not limited by the above disclosed specific embodiments. On the contrary, its purpose is to cover various changes and arrangements with equivalents within the scope of the patent that the present invention hopes to apply for.

Claims

1. An organic composition, comprising: At least one donor material, which comprises at least one organic conjugated polymer or organic conjugated small molecule; and At least one acceptor material, which comprises a first acceptor material having a structure as shown in Formula I: Wherein the core is phenyl; Ar1 is a five- or six-membered heterocyclic ring containing at least one heteroatom, and the heteroatom is independently selected from at least one of S, N, O, and Se; R1, R2, R3, and R4 are independently selected from one of the following groups and their derivatives: C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 ester group, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 silylaryl, C1-C30 silylheteroaryl, C1-C30 alkoxyaryl, C1-C30 alkoxyheteroaryl, C1-C30 alkylthioaryl, C1-C30 alkylthioheteroaryl, C1-C30 haloalkylaryl, C1-C30 haloalkylheteroaryl, C2-C30 ester group aryl, and C2-C30 ester group heteroaryl; and R5, R6, R7, and R8 are independently selected from one of the following groups and their derivatives: C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, halogen, hydrogen atom, and cyano group, where R5, R6, R7, and R8 are not simultaneously hydrogen atoms.

2. The organic composition according to claim 1, wherein Ar1 is selected from one of the following structures: Among them, R9 and R 10 is independently selected from the following groups and one of their derivatives: halogen, hydrogen atom, cyano, C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 ester, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 silylaryl, C1-C30 silylheteroaryl, C1-C30 alkoxyaryl, C1-C30 alkoxyheteroaryl, C1-C30 alkylthioaryl, C1-C30 alkylthioheteroaryl, C1-C30 haloalkylaryl, C1-C30 haloalkylheteroaryl, C2-C30 esteraryl and C2-C30 esterarylheteroaryl, wherein R9 and R 10 It can be two separate groups or connected to each other by a single bond.

3. The organic composition according to claim 1, wherein the donor material is further selected from at least one organic conjugated polymer.

4. The organic composition according to claim 3, wherein the organic conjugated polymer is selected from one of the following structures: in, Ar2, Ar3, Ar4, and Ar5 are monocyclic or polycyclic structures respectively containing C4-C30 ring atoms; n is the number of molecules, and n is a positive integer from 1 to 1000; and x and y are mole fractions, where 0 < x < 1, 0 < y < 1, and x + y = 1.

5. The organic composition according to claim 4, wherein Ar2 and Ar4 are independently selected from one of the following structures: wherein A1, A2, A3 and A4 are independently selected from one of O, S, Se and NR, and R is selected from one of the following groups and derivatives thereof: C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 ester, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 silylaryl, C1-C30 silylheteroaryl, C1-C30 alkoxyaryl, C1-C30 alkoxyheteroaryl, C1-C30 alkylthioaryl, C1-C30 alkylthioheteroaryl, C1-C30 haloalkylaryl, C1-C30 haloalkylheteroaryl, C2-C30 esteraryl and C2-C30 esteraryl heteroaryl; and R 11 , R 12 , R 13 , R 14 , R 15 and R 16 Independently selected from the following groups and one of their derivatives: hydrogen atom, halogen, cyano, C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 ester, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 silylaryl, C1-C30 silylheteroaryl, C1-C30 alkoxyaryl, C1-C30 alkoxyheteroaryl, C1-C30 alkylthioaryl, C1-C30 alkylthioheteroaryl, C1-C30 haloalkylaryl, C1-C30 haloalkylheteroaryl, C1-C30 esteraryl and C2-C30 esterarylheteroaryl.

6. The organic composition according to claim 4, wherein Ar3 and Ar5 are independently selected from one of the following structures: wherein A5, A6, A7 and A8 are independently selected from one of O, S, Se and NR, and R is selected from one of the following groups and derivatives thereof: C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 ester, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 silylaryl, C1-C30 silylheteroaryl, C1-C30 alkoxyaryl, C1-C30 alkoxyheteroaryl, C1-C30 alkylthioaryl, C1-C30 alkylthioheteroaryl, C1-C30 haloalkylaryl, C1-C30 haloalkylheteroaryl, C2-C30 esteraryl and C2-C30 esterarylheteroaryl; and R 17 , R 18 , R 19 , R 20 , R 21 and R 22 Independently selected from the following groups and one of their derivatives: hydrogen atom, halogen, cyano, C1-C30 alkyl, C1-C30 silyl, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 ester, C1-C30 alkylaryl, C1-C30 alkylheteroaryl, C1-C30 silylaryl, C1-C30 silylheteroaryl, C1-C30 alkoxyaryl, C1-C30 alkoxyheteroaryl, C1-C30 alkylthioaryl, C1-C30 alkylthioheteroaryl, C1-C30 haloalkylaryl, C1-C30 haloalkylheteroaryl, C1-C30 esteraryl and C2-C30 esterarylheteroaryl. 7 . The organic composition according to claim 1 , wherein the receptor material further comprises a second receptor material, and the second receptor material is an organic conjugated polymer or an organic conjugated small molecule.

8. The organic composition according to claim 7, wherein the second acceptor material comprises a fullerene structure.

9. An organic optoelectronic component, comprising: a first electrode; An active layer comprising at least one organic composition as claimed in claim 1; and The second electrode, wherein the active layer is located between the first electrode and the second electrode, and at least one of the first electrode and the second electrode is a transparent or semi-transparent electrode.

10. The organic photoelectric component according to claim 9, wherein the organic photoelectric component further comprises a first carrier transfer layer and a second carrier transfer layer, the first carrier transfer layer is arranged between the first electrode and the active layer, and the first carrier transfer layer is used to transfer carriers in the first electrode and the active layer; the second carrier transfer layer is arranged between the active layer and the second electrode, and the second carrier transfer layer is used to transfer carriers in the active layer and the second electrode.

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