Low energy gap small molecule materials and organic optoelectronic components using the same

Abstract

An organic optoelectronic component includes a first electrode, a first carrier transport layer, an active layer, a second carrier transport layer, and a second electrode. The first electrode is a transparent electrode. The active layer contains a low-energy-gap small molecule material of Formula I: #imgabs0# where o, m, n, p, x, and y are independently selected from any integer from 0 to 2. Ar 0 , Ar 1 , and Ar 2 are electron-donating groups. A 0 is a tricyclic structure containing a heteroatom with or without substituents, and the heteroatom includes at least one of S, N, Si, and Se. A 1 is an electron-withdrawing group with or without substituents, and the structure of the electron-withdrawing group contains at least one of S, N, Si, Se, C═O, -CN, and SO2. The organic optoelectronic component of the present invention has good external quantum efficiency and dark current performance.

Description

Technical Field

[0001] The invention relates to a low energy gap small molecule material applied to an organic photoelectric component and an organic photoelectric component containing the low energy gap small molecule material. Background Art

[0002] As the world warms, climate change has become a common challenge faced by the international community. The Kyoto Protocol proposed by the United Nations Framework Convention on Climate Change (UNFCCC) in 1997 officially came into effect in 2005, with the goal of reducing carbon dioxide emissions. In response, all countries focus on the development of renewable energy to reduce the use of fossil fuels. Among them, solar power generation is highly valued among renewable energy sources because the sun provides more than enough energy to meet people's current and future energy needs. In solar power generation technology, organic photovoltaic components used to convert sunlight into electrical energy have become the primary development target.

[0003] At present, the mainstream strategy for preparing high-efficiency organic optoelectronic components is to use high-molecular polymer electron donor materials and non-fullerene electron acceptor materials to construct the active layer. However, during the preparation process, high-molecular polymer materials usually have problems such as difficulty in accurately controlling molecular weight and dispersion, difficulty in purification, and poor batch stability of materials, which makes the corresponding organic optoelectronic components have low repeatability in efficiency and are not conducive to large-scale commercial applications. In contrast, the molecular weight of small organic molecules is determined, which can be accurately synthesized, easy to purify, and has high batch stability, which is conducive to large-scale preparation. Therefore, organic optoelectronic components made of small organic molecule materials have high commercial application potential.

[0004] In recent years, organic small molecule materials, such as non-fullerene materials, have been used in organic solar cells and organic light sensors because of their adjustable structure, high extinction coefficient and other advantages, and have good performance. The wavelength of visible light is 400-700nm, while the absorption wavelength range of current solar cells is 320-1100nm, and it has no absorption capacity for infrared light exceeding 1200nm. It can be seen that there are still many photons of sunlight that have not been used and converted into current or signals in the infrared light. Therefore, the development of organic small molecule materials that can absorb infrared light and apply them to organic optoelectronic components is currently a very important topic.

[0005] On the other hand, the wavelength range that needs to be detected in organic light sensors is not limited to within 1000nm. For example, smart driving and drones require better penetration and long-distance detection, and the application wavelength needs to exceed 1000nm. Water absorbs at a wavelength of 1350nm, and detectors can be used to detect the moisture level of food or medicine to avoid accidental ingestion and affect the human body. Light with a wavelength of more than 1000nm has deeper tissue penetration for biological detection, which can improve the contrast of the image, and organic optoelectronic components have good flexibility, which is conducive to the production of wearable health detectors. At present, most organic small molecule materials can only absorb light up to 800nm ​​at most, so most of them still use organic polymer materials that can absorb wavelengths exceeding 1000nm as application materials. Based on the above two reasons, the development of organic small molecule materials with light response greater than 1000nm is another very important topic at present. Summary of the invention

[0006] In view of this, one of the scopes of the present invention is to provide a low energy gap small molecule material to break through the absorption capacity of the prior art in the infrared region. According to a specific embodiment of the present invention, there is a low energy gap small molecule material comprising a structure of formula 1:

[0007]

[0008] wherein o, m, n, p, x and y are independently selected from any integer between 0 and 2. 0 ,Ar 1 with Ar 2 A is an electron-pushing basis. 0 A is a tricyclic structure containing a heteroatom which may have a substituent, and the heteroatom includes at least one of S, N, Si and Se. 1 It is an electron-withdrawing group with or without a substituent, and the structure of the electron-withdrawing group contains at least one of S, N, Si, Se, C=O, -CN and SO2.

[0009] Among them, Ar 0 ,Ar 1 with Ar 2 is a heterocyclic ring containing a heteroatom, wherein the heteroatom includes at least one of S, N, Si and Se.

[0010] Among them, Ar in the structure of formula 1 0 ,Ar 1 with Ar 2 They may be the same or different from each other, and Ar 0 ,Ar 1 with Ar 2 Independently selected from one of the following groups:

[0011]

[0012] Among them, R in each structure 0 They can be the same or different from each other, and R 0 independently selected from one of the following groups: C1-C30 alkyl, C3-C30 branched alkyl, C1-C30 silyl, C2-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 olefin, C2-C30 alkyne, C2-C30 carbon chain containing cyano, C1-C30 carbon chain containing nitro, C1-C30 carbon chain containing hydroxyl, C3-C30 carbon chain containing keto, halogen, cyano, hydrogen, having one or more R 1 A substituted or unsubstituted aromatic ring having one or more R 1 A substituted or unsubstituted heterocyclic ring having one or more R 1 A fused ring having a substituent or no substituent, and having one or more R 1 A fused heterocyclic ring which may or may not have a substituent. 1 The substituents may be the same or different from each other, and R 1 The substituents are independently selected from one of the following groups: C1-C30 alkyl groups, C3-C30 branched alkyl groups, C1-C30 silyl groups, C2-C30 ester groups, C1-C30 alkoxy groups, C1-C30 alkylthio groups, C1-C30 haloalkyl groups, C2-C30 olefins, C2-C30 alkynes, C2-C30 carbon chains containing cyano groups, C1-C30 carbon chains containing nitro groups, C1-C30 carbon chains containing hydroxyl groups, C3-C30 carbon chains containing keto groups, halogens, cyano groups and hydrogen atoms.

[0013] Among them, A in the structure of formula 1 0 They can be the same or different from each other, and A 0 Independently selected from one of the following groups:

[0014] and

[0015] wherein z is any integer from 1 to 8. 3 with Ar 4 Independently selected from the following groups: having one or more R 2 A substituted or unsubstituted aromatic ring having one or more R 2 A substituted or unsubstituted heterocyclic ring having one or more R 2 A fused ring having a substituent or no substituent, and having one or more R 2A fused heterocyclic ring which may or may not have a substituent. 5 independently selected from one of the following groups: C1-C30 alkyl, C3-C30 branched alkyl, C1-C30 silyl, C2-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 olefin, C2-C30 alkyne, C2-C30 carbon chain containing cyano, C1-C30 carbon chain containing nitro, C1-C30 carbon chain containing hydroxyl, C3-C30 carbon chain containing keto, halogen, cyano, hydrogen, having one or more R 3 A substituted or unsubstituted aromatic ring having one or more R 3 A substituted or unsubstituted heterocyclic ring having one or more R 3 A fused ring having a substituent or no substituent, and having one or more R 3 A fused heterocyclic ring having a substituent or no substituent. 2 and R 3 They can be the same or different from each other, and R 2 and R 3 Independently selected from one of the following groups: C1-C30 alkyl, C3-C30 branched alkyl, C1-C30 silyl, C2-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 olefin, C2-C30 alkyne, C2-C30 carbon chain containing cyano, C1-C30 carbon chain containing nitro, C1-C30 carbon chain containing hydroxyl, C3-C30 carbon chain containing keto, halogen, cyano and hydrogen atoms.

[0016] Among them, A in the structure of formula 1 1 They may be the same or different from each other, and A1 is independently selected from one of the following groups:

[0017]

[0018]

[0019] R 4 They can be the same or different from each other, and R 4Independently selected from one of the following groups: C1-C30 alkyl, C3-C30 branched alkyl, C1-C30 silyl, C2-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 olefin, C2-C30 alkyne, C2-C30 carbon chain containing cyano, C1-C30 carbon chain containing nitro, C1-C30 carbon chain containing hydroxyl, C3-C30 carbon chain containing keto, halogen, cyano and hydrogen atoms.

[0020] Wherein, in the structure of Formula 1, m=n, o=p, and x=y.

[0021] Among them, Ar in the structure of formula 1 1 =Ar 2 .

[0022] Among them, in the structure of formula 1, m+n+o+p≠0.

[0023] Among them, x+y≠0 in the structure of formula 1.

[0024] Another scope of the present invention is to provide an organic optoelectronic component, comprising a first electrode, a first carrier transfer layer, an active layer, a second carrier transfer layer and a second electrode. The first electrode is a transparent electrode. The active layer comprises at least one of the aforementioned low energy gap small molecule materials. The first carrier transfer layer is located between the first electrode and the active layer, the active layer is located between the first carrier transfer layer and the second carrier transfer layer, and the second carrier transfer layer is located between the active layer and the second electrode.

[0025] Compared with the prior art, the organic optoelectronic device made of the low energy gap small molecule material of the present invention has good absorption in the infrared region, and also has good performance in EQE and dark current. BRIEF DESCRIPTION OF THE DRAWINGS

[0026] Figure 1 A structural schematic diagram of a specific embodiment of an organic optoelectronic component of the present invention is depicted.

[0027] Figure 2 The UV-Vis-NIR absorption spectra of specific embodiments Q1 to Q4 of the low energy gap small molecule material of the present invention dissolved in chloroform solution are shown.

[0028] Figure 3 The UV-Vis-NIR absorption spectra of specific embodiments Q1 to Q4 of the low energy gap small molecule material of the present invention in the thin film are shown.

[0029] Figure 4 A schematic diagram showing the energy level positions of specific embodiments Q1 to Q4 of the low energy gap small molecule material of the present invention is shown.

[0030] Figure 5 Schematic diagrams of material energy levels of specific embodiments P1, P2, Q2, and Q3 of the organic optoelectronic components of the present invention are shown.

[0031] Figure 6 The EQE test results of the specific embodiment P2:Q2 of the organic optoelectronic component of the present invention are shown.

[0032] Figure 7 The dark current test results of the specific embodiment P2:Q2 of the organic optoelectronic component of the present invention are shown.

[0033] Figure 8 The EQE test results of the specific embodiment P1:Q3 of the organic optoelectronic component of the present invention are shown.

[0034] Fig. 9 The dark current test results of the specific embodiment P1:Q3 of the organic optoelectronic component of the present invention are shown. DETAILED DESCRIPTION

[0035] 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 and 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.

[0036] 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.

[0037] 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.

[0038] definition:

[0039] As used herein, a compound is considered "environmentally stable" or "stable under environmental conditions" when a transistor incorporating the compound as its semiconductor material exhibits carrier mobility maintained at its initial value after the compound is exposed to environmental conditions, such as air, ambient temperature and humidity for a period of time. For example, a compound may be considered environmentally stable if a transistor incorporating the compound exhibits a carrier mobility that changes by no more than 20% or by no more than 10% of the initial value after exposure to environmental conditions including air, humidity and temperature for 3 days, 5 days or 10 days.

[0040] The external quantum efficiency (EQE) used in this article refers to the quantum efficiency obtained by converting the spectral response unit Amp / Watt, converting amperes Amp into electrons per unit time (electron / sec), and converting watts Watt into photons per unit time (Photons / sec) into the above formula. Generally speaking, quantum efficiency (QE) refers to external quantum efficiency (EQE), also known as incident photon-electron conversion efficiency (IPCE).

[0041] 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.

[0042] 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.

[0043] As used herein, "annealing" refers to a post-deposition heat treatment of a semi-crystalline polymer film for a certain duration in an ambient environment 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 believed that annealing may lead to an increase in crystallinity in the polymer film, improve the material carrier mobility of the polymer film or the mixed film of the polymer and other molecules, and form an interactive molecular arrangement to achieve an effect of independent transfer paths for effective electrons and holes.

[0044] In the current technology, the ability to absorb near-infrared light is mostly achieved by designing an organic polymer structure of "electron donor-π-electron acceptor". Other technologies use the design of an organic small molecule structure of "electron donor-electron acceptor-electron donor" to achieve the ability to absorb 600-800nm ​​light. The present invention provides a low-energy gap small molecule material. The concept of molecular structure design is that the outer structure of this low-energy gap small molecule material has two strong electron-pulling groups, and the connected central structure is a system with π electrons or multiple electrons. Further, the molecular structure of the present invention is designed as A 1 -A 0 -Ar 0 -A 0 -A 1 , where Ar is located in the central structure 0 It can be π or a condensed ring with strong electron-donating ability, A 0 A is a polycondensed ring located on the outermost structure 1 The present invention uses multiple electron-withdrawing functional groups in the structure, and such a design is easier to achieve near-infrared light absorption than a design using a single strong electron-withdrawing group.

[0045] In one embodiment, the low energy gap small molecule material of the present invention comprises a structure of Formula 1:

[0046]

[0047] wherein o, m, n, p, x and y are independently selected from any integer between 0 and 2. 0 ,Ar 1 with Ar 2 A is an electron-pushing basis. 0 A is a tricyclic structure containing heteroatoms with or without substituents, wherein the heteroatoms include at least one of S, N, Si and Se. The light absorption properties and solubility can be adjusted by adjusting the heteroatoms. 1 It is an electron-withdrawing group with or without a substituent, and the structure of the electron-withdrawing group contains at least one of S, N, Si, Se, C=O, -CN and SO2. In practical applications, the double bond in Formula 1 may be a double bond with or without a substituent, and is not limited to this. Among them, the electron-withdrawing group is a group or atom with stronger electron-withdrawing ability than hydrogen, that is, it has an electron-withdrawing inductive effect; and the electron-pushing group is a group or atom with 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 (electronegativity) of atoms or groups in the molecule. The electron cloud tends to move toward the group or atom with stronger electronegativity.

[0048] In a specific embodiment, Ar 0 ,Ar 1with Ar 2 is a heterocyclic ring containing a heteroatom, and the heteroatom includes at least one of S, N, Si and Se.

[0049] In a specific embodiment, Ar in the structure of Formula 1 0 , multiple Ar 1 With multiple Ar 2 They may be the same or different from each other, and Ar 0 , each Ar 1 With each Ar 2 Independently selected from one of the following groups:

[0050]

[0051] The multiple R 0 They can be the same or different from each other, and each R 0 independently selected from one of the following groups: C1-C30 alkyl, C3-C30 branched alkyl, C1-C30 silyl, C2-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 olefin, C2-C30 alkyne, C2-C30 carbon chain containing cyano, C1-C30 carbon chain containing nitro, C1-C30 carbon chain containing hydroxyl, C3-C30 carbon chain containing keto, halogen, cyano, hydrogen, having one or more R 1 A substituted or unsubstituted aromatic ring having one or more R 1 A substituted or unsubstituted heterocyclic ring, a fused ring having one or more R1 substituents or no substituents, and a fused ring having one or more R 1 A fused heterocyclic ring having a substituent or no substituent. 1 The substituents may be the same or different from each other, and each R 1 The substituents are independently selected from one of the following groups: C1-C30 alkyl groups, C3-C30 branched alkyl groups, C1-C30 silyl groups, C2-C30 ester groups, C1-C30 alkoxy groups, C1-C30 alkylthio groups, C1-C30 haloalkyl groups, C2-C30 olefins, C2-C30 alkynes, C2-C30 carbon chains containing cyano groups, C1-C30 carbon chains containing nitro groups, C1-C30 carbon chains containing hydroxyl groups, C3-C30 carbon chains containing keto groups, halogens, cyano groups and hydrogen atoms.

[0052] In one embodiment, multiple A in the structure of Formula 1 0 They can be the same or different from each other, and each A 0 Independently selected from one of the following groups:

[0053] and

[0054] Wherein z is any integer from 1 to 8. 3 with Ar 4 Independently selected from the following groups: having one or more R 2 A substituted or unsubstituted aromatic ring having one or more R 2 A substituted or unsubstituted heterocyclic ring having one or more R 2 A fused ring having a substituent or no substituent, and having one or more R 2 A fused heterocyclic ring which may or may not have a substituent. 5 independently selected from one of the following groups: C1-C30 alkyl, C3-C30 branched alkyl, C1-C30 silyl, C2-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 olefin, C2-C30 alkyne, C2-C30 carbon chain containing cyano, C1-C30 carbon chain containing nitro, C1-C30 carbon chain containing hydroxyl, C3-C30 carbon chain containing keto, halogen, cyano, hydrogen, having one or more R 3 A substituted or unsubstituted aromatic ring having one or more R 3 A substituted or unsubstituted heterocyclic ring having one or more R 3 A fused ring having a substituent or no substituent, and having one or more R 3 A fused heterocyclic ring having a substituent or no substituent. 2 and multiple R 3 They can be the same or different from each other, and each R 2 and each R 3 Independently selected from one of the following groups: C1-C30 alkyl, C3-C30 branched alkyl, C1-C30 silyl, C2-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 olefin, C2-C30 alkyne, C2-C30 carbon chain containing cyano, C1-C30 carbon chain containing nitro, C1-C30 carbon chain containing hydroxyl, C3-C30 carbon chain containing keto, halogen, cyano and hydrogen atoms.

[0055] In one embodiment, multiple A in the structure of Formula 1 1 They can be the same or different from each other, and each A 1 Independently selected from one of the following groups:

[0056]

[0057]

[0058] Among them, multiple R 4 They can be the same or different from each other, and each R 4 Independently selected from one of the following groups: C1-C30 alkyl, C3-C30 branched alkyl, C1-C30 silyl, C2-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 olefin, C2-C30 alkyne, C2-C30 carbon chain containing cyano, C1-C30 carbon chain containing nitro, C1-C30 carbon chain containing hydroxyl, C3-C30 carbon chain containing keto, halogen, cyano and hydrogen atoms.

[0059] In a specific embodiment, the low energy gap small molecule material of the present invention may include the following structure:

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070] The above embodiments include at least one of the following conditions: m=n, o=p, and x=y; at least one of m≠n, o≠p, and x≠y; Ar 1 =Ar 2 ;Ar 1 ≠Ar 2In addition, in practical applications, at least one of the following conditions is included: m+n+o+p≠0 and x+y≠0. It should be understood that the above-listed embodiments are only for the purpose of allowing ordinary technicians in the field to more clearly understand the structural composition of the present invention, and are not limited thereto.

[0071] See also Figure 1 , Figure 1 FIG. 1 is a schematic structural diagram of a specific embodiment of an organic optoelectronic component 1 of the present invention. Figure 1 As shown, in another embodiment, the present invention further provides an organic optoelectronic 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, wherein the active layer 13 includes the aforementioned low energy gap small molecule material. In this specific embodiment, the organic optoelectronic component 1 can be a stacked structure, which sequentially includes a substrate 10, a first electrode 11 (transparent electrode), a first carrier transfer layer 12, an active layer 13, a second carrier transfer layer 14 and a second electrode 15. In practice, the organic optoelectronic component 1 can include an organic photovoltaic component, an organic light sensing component, an organic light emitting diode and an organic thin film transistor (OTFT).

[0072] In practical applications, the active layer 13 of the organic optoelectronic device 1 of the present invention includes the aforementioned low energy gap small molecule material of Formula 1.

[0073] In order to more clearly illustrate the low energy gap small molecule material of the present invention, four specific embodiments Q1 to Q4 are used to use the low energy gap small molecule material of the present invention as the N-type material of the active layer and further prepared into an organic optoelectronic component for experiment.

[0074] Preparation of active layer:

[0075] Synthesis of C3:

[0076]

[0077] Take C1 (10g, 86.3mmol) and put it into a 500mL four-necked reaction bottle. Under stirring, add 50mL of anhydrous THF to dissolve and cool to 15℃. Slowly drip 34.5mL n-BuLi (n-butyl lithium), the process is about 60 minutes, the solution is light orange, and the temperature does not exceed 17℃. Return to room temperature and stir for 1 hour. At 15℃, drip C2 (19.81g, 5.62mmol), the process is about 2 minutes, and the solution is light yellow and clear. Return to room temperature and stir for 20 hours. Add 5mL of water to stop the reaction, vacuum rotary concentrate to remove the organic solvent, add 100mL of Heptane (heptane), and extract three times with 20mL of water. Take the organic layer to remove water, vacuum rotary concentrate to remove the organic solvent to obtain a crude product of about 20g. Remove the starting material and impurities by reduced pressure distillation (0.25torr, 80-100℃). The residue (about 10 g) was purified by silica gel column, and the eluent was heptane (about 150 mL). The main fraction was collected, the organic solvent was removed, and the product was dried at 50°C in vacuum to obtain a light yellow oil C3. Yield: 9.3 g, 51%. 1 H NMR (500MHz, CDCl3) δ7.09 (d, J = 6.5 Hz, 1H), 6.85 (d, J = 6.5 Hz, 1H), 2.72 (d, J = 7.0 Hz, 2H), 1.68 (m, 1H), 1.27 (m, 24H), 0.88 (m, 6H).

[0078] Synthesis of C4:

[0079]

[0080] Take C3 (20g, 58.31mmol) and place it in a 250mL three-necked reaction bottle. Add 160mL THF (tetrahydrofuran). Add n-BuLi (23.32mL, 58.31mmol) in an ice bath (<10℃). Keep stirring for one hour in an ice bath (<10℃). Take CuBr (cuprous bromide) (8.36g, 58.31mmol) and LiBr (lithium bromide) (5.06g, 58.31mmol) and place them in another 500mL three-necked reaction bottle, and add 160mL THF in an ice bath. Mix and stir the two reaction mixtures in an ice bath for 1 hour. Add oxalyl chloride (3.36g, 2.27mL, 26.5mmol) in an ice bath, return to room temperature and stir for 18 hours. Add 100 mL of water to terminate the reaction, remove most of the THF by vacuum rotary concentrator, add 200 mL of heptane, and extract three times with 100 mL of water. Collect the organic layer, remove water and concentrate. Purify with a silica gel column, the eluent is Hep / DCM (n-heptane / dichloromethane) = 4 / 1. Collect the main fraction and concentrate to obtain orange-yellow oily liquid C4. Yield: 12 g, 61.2%. 1 H NMR (500MHz, CDCl3) δ7.88 (s, 2H), 2.80 (d, J = 7.0Hz, 4H), 1.76 (m, 2H), 1.29 (m, 48H), 0.88 (m, 12H).

[0081] Synthesis of C7:

[0082]

[0083] Take C5 (2g, 5.21mmol) and put it into a 100mL three-necked reaction bottle. Add 60mL glacial acetic acid. Add iron powder (5.83g, 104.4mmol) under vigorous stirring with a magnet. Heat to 80℃ and react for 16 hours. Cool to room temperature, pour the reaction mixture into 200mL ice water and filter, rinse the solid with distilled water and drain. Dissolve the crude product with 200mL THF and filter to remove the iron powder. Concentrate the organic solution under reduced pressure to obtain C6, and dry it in vacuum. Obtain C6 intermediate, yield: 1.35g, 80%. Add C4 (2.7g, 3.65mmol) and 40mL glacial acetic acid. Heat to 120℃ and react for 16 hours under vigorous stirring with a magnet. Cool to room temperature, pour the reaction mixture into 50mL ice water. Extract with DCM (dichloromethane), and wash the organic layer three times with 50mL distilled water. The organic layer is dehydrated with anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a crude product. Purify with silica gel column, eluent Hep / DCM (n-heptane / dichloromethane) = 4 / 1. Collect the main fraction, concentrate to obtain dark red solid, and dry in vacuo to obtain C7, yield: 2.4 g, 61.6%. 1H NMR (500MHz, CDCl3) δ7.45 (s, 2H), 2.83 (d, J = 7.0Hz, 4H), 1.83 (m, 2H), 1.30 (m, 48H), 0.89 (m, 12H).

[0084] Synthesis of C9:

[0085]

[0086] Take C7 (1 g, 0.97 mmol) and C8 (1.05 g, 2.52 mmol) in a 100 mL three-necked reaction bottle, add 30 mL THF. Deoxygenate for 15 minutes under argon. Add Pd2(dba)3 (tri(dibenzylideneacetone)dipalladium) (0.036 g, 0.039 mmol) and P(o-tolyl)3 (tri(2-methylphenyl)phosphine) (0.048 g, 0.158 mmol), heat to 66°C, and stir for 2 hours. After cooling, filter with Celite, rinse with Heptane, and remove the organic solution by vacuum rotary concentration. Chromatography with silica gel column, the eluent is DCM / Hep=1 / 9. Collect the main fraction and concentrate to obtain brown viscous liquid C9. Yield: 1.23 g, 92.2%. 1 H NMR (500MHz, CDCl3) δ 8.70 (s, 2H), 7.40 (s, 2H), 7.29 (s, 2H), 2.83 (d, J = 7.0Hz, 4H), 2.76 (t, J = 7.0Hz, 4H), 1.76 (m, 6H), 1.42 (m, 84H), 0.85 (m, 18H).

[0087] Synthetic C10:

[0088]

[0089] Take C9 (1.23g, 0.90mmol) and put it into a 100mL three-necked reaction bottle. Under nitrogen, add 61.5mL DCE (1,2-dichloroethane). Under nitrogen, mix POCl3 (phosphorus oxychloride) (0.503mL, 5.38mmol) and DMF (dimethylformamide) (3.47mL, 4.5mmol) and stir at room temperature for 10 minutes. Mix the above two mixture solutions and stir and heat to 60℃ for 15 hours. Add 100mL water to terminate the reaction, and then add 200mL DCM. The organic layer is extracted three times with 100mL water, and the organic layer is filtered and concentrated by dehydrating with anhydrous magnesium sulfate. Chromatography is performed on a silica gel column, and the eluent is DCM / Hep=5 / 5. The main segment is collected and concentrated to obtain a dark brown viscous liquid C10. Yield: 1.17g, 93.2%. 1H NMR (500MHz, CDCl3) δ10.19(s,1H),8.80(s,1H),8.77(s,1H),7.47(s,1H),7.46(s,1 H),7.37(s,1H),3.11(m,2H),2.80(m,6H),1.80(m,6H),1.30(m,84H),0.85(m,18H).

[0090] Synthesis of C11:

[0091]

[0092] Take C10 (1.17 g, 0.84 mmol) and put it into a 100 mL three-necked reaction bottle. Under nitrogen, add 35 mL CF. Under ice bath (<10°C), add NBS (N-bromosuccinimide) (0.193 g, 1.08 mmol). Stir at room temperature for 18 hours. Remove the organic solvent by vacuum rotary concentration. Chromatography on silica gel column, eluent DCM / Hep = 5 / 5. Collect the main segment and concentrate to obtain dark brown viscous liquid C11. Yield: 1.22 g, 98.7%. 1 H NMR (500MHz, CDCl3) δ10.19(s,1H),8.79(s,1H),8.76(s,1H),7.46(s,1H),7.44(s,1 H),3.10(m,2H),2.87(m,4H),2.76(m,2H),1.80(m,6H),1.30(m,84H),0.86(m,18H).

[0093] Synthesis of C13:

[0094]

[0095] Take C11 (0.18 g, 0.12 mmol) and C12 (0.028 g, 0.06 mmol) and place them in a 100 mL three-necked reaction bottle. Under argon, add 2 mL of THF and deoxygenate for 15 minutes. Add Pd2(dba)3 (0.002 g, 0.0024 mmol) and P(o-tolyl)3 (0.003 g, 0.0096 mmol), heat to 66°C, and stir for 2 hours. After cooling, filter with Celite, rinse with DCM, and remove the organic solution by vacuum rotary concentration. Chromatography with a 100 g silica gel column, the eluent is DCM / Hep=5 / 5. Collect the main segment and concentrate to obtain a brown viscous liquid C13. Yield: 0.14 g, 82.3%. 1H NMR (500MHz, CDCl3) δ10.18(s,2H),8.90(s,2H),8.72(s,2H),7.59(s,2H),7.47(s,2H),7.4 4(s,2H),3.10(m,4H),2.87(m,8H),2.76(m,4H),1.80(m,12H),1.30(m,168H),0.84(m,36H).

[0096] Synthesis of Q1:

[0097]

[0098] Take C13 (0.14 g, 0.047 mmol) and C14 (0.043 g, 0.188 mmol) and put them into a 100 mL three-necked reaction bottle. Under argon, add 2.8 mL CF (chloroform). Add pyridine (0.07 mL, 0.5 V). Stir and heat to 65 ° C for 2 hours. Add 5 mL MeOH (methanol) to terminate the reaction, and let the crude product precipitate and filter. The crude product solid is chromatographed on a silica gel column, and the eluent is CF / Hep = 1 / 1. Collect the main segment, concentrate to obtain a black solid, and use Acetone (acetone) and MeOH ultrasonic vibration to clean, and filter to obtain a black solid Q1. Yield: 0.135 g, 84.2%. 1 H NMR (600MHz, TCE-d2, 100℃) δ8.69(br,6H),8.60(s,2H),8.09(s,2H),7.78(s, 2H),7.60(br,4H),2.95(br,12H),1.95(m,16H),1.40(m,168H),0.89(m,36H).

[0099] Synthetic C16:

[0100]

[0101] Take C15 (0.356g, 0.53mmol) and put it into a 100mL three-necked reaction bottle, add 7mL of anhydrous THF. Under an ice bath (<10℃), drop n-BuLi (0.96mL, 2.39mmol) and stir for 1 hour. Add Me3SnCl (trimethyltin chloride) (0.53g, 2.66mmol) dissolved in 2mL of anhydrous THF and return to room temperature. After stirring for two hours, add 10mL of water to terminate the reaction, and add 20mL of Heptane. Extract three times with 10mL of water. Collect the organic layer, remove water and concentrate to obtain a yellow-orange oily liquid C16. Yield: 0.52g, 97.4%. 1H NMR (500MHz, CDCl3) δ7.00 (s, 2H), 6.81 (s, 6H), 2.46 (t, J = 7.5Hz, 8H), 1.50 (br, 8H), 1.26 (br, 24H), 0.86 (m, 12H), 0.35 (m, 18H).

[0102] Synthesis of C17:

[0103]

[0104] Take C11 (0.98 g, 0.66 mmol) and C16 (0.328 g, 0.33 mmol) and place them in a 100 mL three-necked reaction bottle. Under argon, add 30 mL THF and deoxygenate for 15 minutes. Add Pd2(dba)3 (0.012 g, 0.013 mmol) and P(o-tolyl)3 (0.016 g, 0.052 mmol), heat to 66°C, and stir for 6 hours. After cooling, filter with Celite, rinse with DCM, and remove the organic solution by vacuum rotary concentration. Chromatography on a silica gel column, the eluent is DCM / Hep = 5 / 5. Chromatography on a silica gel column, the eluent is Toluene (toluene) / Hep = 4 / 6. Collect the main segment and concentrate to obtain a brown viscous liquid. Yield: 0.9 g, 78.4%. 1 HNMR(500MHz, CDCl3)δ10.19(s,2H),8.94(s,2H),8.80(s,2H),7.60(s,2H),7.48(s,2H),7.31(s,2H),6.97(s,4 H),6.95(s,2H),3.10(m,4H),2.97(m,8H),2.83(m,4H),2.52(m,8H),1.95(m,16H),1.30(m,196H),0.80(m,48H).

[0105] Synthesis of Q2:

[0106]

[0107] Take C17 (0.9 g, 0.26 mmol) and C18 (0.274 g, 1.04 mmol) and place them in a 100 mL three-necked reaction bottle. Under argon, add 18 mL of CF. Add pyridine (0.45 mL, 0.5 V). Stir and heat to 65 ° C for 1.5 hours. Add 36 mL of MeOH to terminate the reaction, and filter the crude product. Wash it with EA (ethyl acetate) twice and Acetone ultrasonic shock, and filter to obtain a black solid. Yield: 0.91 g, 88.1%. 1H NMR (600MHz, TCE-d2, 100℃) δ9.10(br,6H),8.81(s,2H),8.08(s,2H),8.03(s,2H),7.63(s,2H),7.42(s,2H), 7.04(s,4H),6.96(s,2H),3.14(m,4H),2.87(m,8H),2.59(m,8H),1.90(m,20H),1.30(m,196H),0.85(m,48H).

[0108] Synthesis of C20:

[0109]

[0110] Take C11 (0.5 g, 0.49 mmol) and C19 (0.121 g, 0.32 mmol) and place them in a 100 mL three-necked reaction bottle, and add 25 mL of THF. Under argon, deoxygenate for 15 minutes. Add Pd2(dba)3 (0.006 g, 0.007 mmol) and P(o-tolyl)3 (0.008 g, 0.026 mmol), heat to 66°C, and stir for 2 hours. After cooling, filter with Celite, rinse with Heptane, and remove the organic solution by vacuum rotary concentration. Collect the main intermediate segment, concentrate to obtain a brown viscous liquid, and vacuum dry to obtain 0.21 g. Under nitrogen, add 10.5 mL of DCE. Under nitrogen, mix POCl3 (0.114 mL, 1.22 mmol) and DMF (0.79 mL, 10.2 mmol). Mix the above two mixture solutions, and stir and heat to 60°C for 48 hours. Add 10 mL of water to terminate the reaction, then add 20 mL of DCM. Extract the organic layer three times with 10 mL of water, remove the water with anhydrous magnesium sulfate, filter and concentrate. Chromatography is performed on a silica gel column, and the eluent is DCM / Hep = 1 / 1. Collect the main fraction and concentrate to obtain a dark brown viscous liquid C20. Yield: 0.14 g, 40.8%. 1 H NMR (500MHz, CDCl3) δ10.08(s,1H),8.94(d,J=4.0Hz,1H),7.92(d,J=4.0Hz,1H),7.48(s,1H),7. 47(s,1H),2.88(d,J=7.0Hz,2H),2.85(d,J=7.0Hz,2H),1.83(m,2H),1.29(m,48H),0.84(m,12H).

[0111] Synthesis of C21:

[0112]

[0113] Take C20 (0.14 g, 0.132 mmol) and C16 (0.07 g, 0.066 mmol) and place them in a 100 mL three-necked reaction bottle. Under argon, add 4.2 mL THF and deoxygenate for 15 minutes. Add Pd2(dba)3 (0.003 g, 0.003 mmol) and P(o-tolyl)3 (0.004 g, 0.012 mmol), heat to 66°C, and stir for 2 hours. After cooling, filter with Celite, rinse with DCM, and remove the organic solution by vacuum rotary concentration. Chromatography with silica gel column, the eluent is DCM / Hep=1 / 1. Collect the main segment and concentrate to obtain brown viscous liquid C21. Yield: 0.145 g, 79.4%. 1 H NMR (500MHz, CDCl3) δ10.07(s,2H),9.28(s,2H),8.99(d,J=4.0Hz,2H),7.96(d,J=4.0Hz,2H),7.51(s,2H),7.45(s,2H),7 .16(s,4H),7.16(s,2H),2.94(m,4H),2.78(m,4H),2.50(m,8H),1.81(m,4H),1.30(m,16H),0.85(m,124H),0.73(m,24H).

[0114] Synthesis Q3:

[0115]

[0116] Take C21 (0.145g, 0.055mmol) and C18 (0.058g, 0.22mmol) and put them into a 100mL three-necked reaction bottle. Under argon, add 2.9mL CF. Add pyridine (0.072mL, 0.5V). Stir and heat to 65℃ for 1.5 hours. Add 10mL MeOH to terminate the reaction, and let the crude product precipitate and filter. The crude product solid is chromatographed on a silica gel column with an eluent of CF / Hep=8 / 2. Collect the main segment, concentrate to obtain a black solid, and wash it with EA ultrasonic vibration, and filter to obtain a black solid Q3. Yield: 0.154g, 89.5%. 1 H NMR (600MHz, TCE-d2, 100℃) δ9.36(s,2H),9.23(s,2H),8.93(s,2H),8.78(s,2H),8.35(s,2H),8.07(s,2H),7.91(s,2H),7 .63(s,2H),7.24(br,4H),6.97(s,2H),2.95(m,4H),2.85(s,4H),2.59(br,8H),1.91(m,4H),1.40(m,140H),0.91(m,24H).

[0117] Synthesis of C23:

[0118]

[0119] Take C22 (1 g, 2.23 mmol) and C8 (2.4 g, 5.79 mmol) and place them in a 100 mL three-necked reaction bottle, and add 45 mL of THF. Deoxygenate under argon for 15 minutes. Add Pd2(dba)3 (0.082 g, 0.089 mmol) and P(o-tolyl)3 (0.108 g, 0.355 mmol), heat to 66°C, and stir for 2 hours. After cooling, filter with Celite, rinse with Heptane, and remove the organic solution by vacuum rotary concentration. Chromatography with silica gel column, the eluent is DCM / Hep = 1 / 4. Collect the main segment and concentrate to obtain blue solid C23. Yield: 1.64 g, 93.2%. 1 H NMR (500MHz, CDCl3) δ 8.69 (s, 2H), 7.23 (s, 2H), 4.91 (d, J = 6.0Hz 2H), 2.76 (m, 4H), 1.74 (m, 5H), 1.36 (m, 44H), 1.07 (m, 3H), 0.87 (m, 9H).

[0120] Synthetic C24:

[0121]

[0122] Take C23 (0.2g, 0.25mmol) and put it into a 100mL three-necked reaction bottle. Under nitrogen, add 10mL DCE. Under nitrogen, mix POCl3 (0.0234mL, 0.25mmol) and DMF (0.155mL, 2mmol) and stir at room temperature for 10 minutes. At <10°C, mix the above two mixture solutions and stir for 1 hour. Add 20mL of water to terminate the reaction, and then add 40mL of DCM. The organic layer is extracted three times with 20mL of water, and the organic layer is dehydrated with anhydrous magnesium sulfate, filtered and concentrated. Chromatography is performed on a silica gel column, and the eluent is DCM / Hep=1 / 1. Collect the main segment and concentrate to obtain a blue viscous liquid. Yield: 0.14g, 67.6%. 1 H NMR (500MHz, CDCl3) δ10.16(s,1H),8.77(s,2H),7.31(s,1H),4.94(d,J=6.5Hz,2H ),3.10(s,2H),2.78(s,2H),1.77(m,5H),1.40(m,44H),1.11(m,3H),0.91(m,9H).

[0123] Synthesis of C25:

[0124]

[0125] Take C24 (0.14 g, 0.17 mmol) and put it into a 100 mL three-necked reaction bottle. Under nitrogen, add 7 mL of THF. Under ice bath (<10°C), add NBS (0.030 g, 0.17 mmol). Stir at room temperature for 18 hours. Remove the organic solvent by vacuum rotary concentration. Chromatography on silica gel column, eluent DCM / Hep = 1 / 1. Collect the main fraction and concentrate to obtain dark blue solid C25. Yield: 0.15 g, 99.1%. 1 H NMR (500MHz, CDCl3) δ10.16(s,1H),8.77(s,1H),8.63(s,1H),4.93(d,J=6.5Hz,2H ),3.09(s,2H),2.72(s,2H),1.77(m,5H),1.40(m,44H),1.07(m,3H),0.88(m,9H).

[0126] Synthesis of C26:

[0127]

[0128] Take C25 (0.15 g, 0.167 mmol) and C16 (0.083 g, 0.084 mmol) and place them in a 100 mL three-necked reaction bottle. Under argon, add 30 mL of THF and deoxygenate for 15 minutes. Add Pd2(dba)3 (0.0031 g, 0.0033 mmol) and P(o-tolyl)3 (0.0041 g, 0.0134 mmol), heat to 66°C, and stir for 17 hours. After cooling, filter with Celite, rinse with DCM, and remove the organic solution by vacuum rotary concentration. Chromatography with silica gel column, the eluent is EA:Hep=1:9. Collect the main segment and concentrate to obtain black solid C26. Yield: 0.14 g, 75.5%. 1 H NMR (500MHz, CDCl3) δ10.16(s,2H),8.80(s,2H),8.75(s,2H),7.30(s,2H),6.95(s,4H),6.92(s,2H),4.94(m,4 H),3.09(m,4H),2.94(m,4H),2.53(m,8H),2.02(m,2H),1.85(m,8H),1.28(m,120H),1.10(m,6H),0.85(m,30H).

[0129] Synthesis Q4:

[0130]

[0131] Take C26 (0.9 g, 0.26 mmol) and C14 (0.274 g, 1.04 mmol) and place them in a 100 mL three-necked reaction bottle. Under argon, add 18 mL of CF. Add pyridine (0.45 mL, 0.5 V). Stir and heat to 65 ° C for 1.5 hours. Add 36 mL of MeOH to terminate the reaction, and filter the crude product. Wash with EA twice and Acetone ultrasonic shock, and filter to obtain a black solid. Yield: 0.91 g, 88.1%. 1 H NMR (600MHz, TCE-d2, 100℃) δ9.06(s,2H),8.95(m,4H),8.56(m,2H),7.76(s,2H),7.41(s,2H),7.04(s,4H),6.98(s,2H),5 .05(m,4H),3.15(br,4H),3.02(br,4H),2.64(m,8H),2.46(m,2H),1.93(m,8H),1.40(m,120H),1.19(m,6H),0.91(m,30H).

[0132] Characteristic test of low energy gap small molecule materials Q1, Q2, Q3 and Q4:

[0133] See also Figures 2 to 4 And Table 1, Figure 2 The UV-Vis-NIR absorption spectra of the specific embodiments Q1 to Q4 of the low energy gap small molecule material of the present invention dissolved in chloroform solution are shown. Figure 3 The UV-Vis-NIR absorption spectra of the specific embodiments Q1 to Q4 of the low energy gap small molecule material of the present invention in the film are shown. Figure 4 The schematic diagram of the energy level position of the specific embodiments Q1 to Q4 of the low energy gap small molecule material of the present invention is shown in Table 1. Figures 2 to 4 The data results.

[0134] Table 1: Figures 2 to 4 The data results

[0135]

[0136] Depend on Figure 2 , Figure 3 As can be seen from Table 1, the low energy gap small molecule material designed by the present invention effectively extends the absorption peak to after 1000nm, and the absorption coefficients of the maximum absorption of Q2-Q4, except Q1, exceed 100,000. Figure 3), the absorption peak is red-shifted due to the intermolecular stacking. Taking Q2 as an example, the maximum absorption peak of Q2 film is red-shifted by about 200nm. It can be predicted that the EQE of the material in the organic light sensor can respond to 1600nm. Figure 4 , Examples Q1 to Q4 used cyclic voltammetry to measure the oxidation properties, and calculated (HOMO = -|4.71 + E ox -E ferroncene |eV) to obtain the highest occupied molecular orbital (HOMO), and then the absorption onset position (λ film onset ), we can know the optical energy gap (E g =1241 / λ film onset eV) and the lowest unoccupied molecular orbital (LUMO, LUMO = HOMO + E g The energy gap of the embodiments of the present invention is less than 0.9 eV, and the absorption response position is more than 1000 nm.

[0137] In order to confirm whether an environmentally friendly solvent can be used for coating, the solubility measurement in Table 1 is based on whether a sample of 8 mg can be completely dissolved in 1 mL of o-xylene. Among them, "O" means complete dissolution, and "X" means incomplete dissolution. It can be understood from Table 1 that Examples Q1 to Q4 of the low-energy gap small molecule material of the present invention can all be completely dissolved in o-xylene, thus proving that the low-energy gap small molecule material of the present invention can be coated using o-xylene. In this field, the use of green solvents that are non-halogen solvents is an industry trend. Green solvents generally come from renewable resources or can be degraded by soil organisms or other substances, have a short half-life, and can easily decay into low-toxic, non-toxic substances. Therefore, compared with general solvents that are easily chlorinated or have higher toxicity, green solvents are generally less harmful to biological health and the environment. Green solvents are also called environmentally friendly solvents. And o-xylene is a non-halogen green solvent.

[0138] Preparation and testing of organic optoelectronic components:

[0139] Pre-patterned indium tin oxide (ITO) coated glass with a sheet resistance of ~15Ω / sq was used as the substrate. Ultrasonic shock treatment was carried out in deionized water containing soap, deionized water, acetone and isopropanol in sequence, and cleaning was carried out for 15 minutes in each step. The washed substrate was further treated with a UV-ozone cleaner for 30 minutes. A top coating of AZO (Aluminum-doped zinc oxide) solution was coated on the ITO substrate at a rate of 3000rpm for 40 seconds and then baked at 120°C in air for 5 minutes. An active layer solution was prepared in o-xylene. The active layer contains the aforementioned organic semiconductor material. In order to completely dissolve the active layer, the active layer solution needs to be stirred at 100°C on a hot plate for at least 1 hour. The active layer is then returned to room temperature for spin coating. Finally, the film formed by the coated active layer is thermally annealed at 100°C for 5 minutes and then transferred to a thermal evaporator. At 3×10 -6 Under a vacuum of 100 torr, a thin layer of MoO3 (8 nm) was deposited as the anode intermediate layer, followed by a 100 nm thick silver as the top electrode. All cells were encapsulated with epoxy resin in a glove box to form an organic electronic component (ITO / ETL / active layer / MoO3 / Ag).

[0140] See also Figure 5 , Figure 5 The material energy level diagram of the specific embodiment P1, P2, Q2, Q3 of the organic optoelectronic component of the present invention is shown. In the preparation of the organic optoelectronic component, P1 or P2 is used as a P-type polymer material in combination with the low energy gap small molecule materials Q2 and Q3 of the present invention. The structures of P1 and P2 are as follows:

[0141]

[0142] Depend on Figure 5 As shown, for the test of organic optoelectronic components, P2 can be matched with Q2 and P1 can be matched with Q3. Because, when matched with P-type polymer material P2 at the energy level of Q2, the difference between the HOMO and LUMO energy levels of P2 and Q2 is sufficient to drive the exciton to disassemble the electron-hole pair. P1 and Q3 are also matched in this principle.

[0143] Among them, in the preparation of the organic optoelectronic component of P2:Q2, P2:Q2=1:1, the concentration is 14mg / mL in o-xylene, and in the preparation of the organic optoelectronic component of P1:Q3, P1:Q3=1:1, the concentration is 10mg / mL in o-xylene. The thickness of the active layer is about 100nm, and the structures of the organic optoelectronic components are glass / ITO / AZO / P2:Q2 / MoO3 / Ag and glass / ITO / AZO / P1:Q3 / MoO3 / Ag respectively.

[0144] Performance analysis of organic optoelectronic components:

[0145] The performance analysis of the organic optoelectronic device of the present invention is mainly focused on the external quantum efficiency (EQE) and the dark current (J d ) for analysis.

[0146] Generally speaking, quantum efficiency (QE) refers to external quantum efficiency (EQE). Quantum efficiency / spectral response reflects the photoelectric conversion efficiency of organic optoelectronic components for different wavelengths, that is, the ability to effectively convert photons into electrons when illuminated. The conversion efficiency of organic optoelectronic components is affected by factors such as its own materials, processes, and structures, resulting in different conversion efficiencies for different wavelengths. In organic light sensor applications, the greater the external quantum efficiency (EQE), the better the signal of the organic light sensor.

[0147] Dark current (J d ), also known as dark current, refers to the current flowing in the optoelectronic component when there is no light. In the dark current test, when the organic optoelectronic component is biased without light. In the application of organic light sensors, the larger the current generated, the greater the noise in the organic light sensor.

[0148] See also Figure 6 and Figure 7 , Figure 6 The EQE test results of the specific embodiment P2:Q2 of the organic optoelectronic component of the present invention are shown. Figure 7 The dark current test results of the specific embodiment P2:Q2 of the organic optoelectronic component of the present invention are shown. Figure 6 As shown, the EQE response of the organic optoelectronic component prepared by P2:Q2 is 3.7% at 1050nm under -2V bias and 12.0% at -10V bias; 2.3% at 1350nm under -2V bias and 7.9% under -10V bias. Figure 7 As shown, the dark current of the specific embodiment P2:Q2 of the organic optoelectronic device of the present invention is within 10 -4A / cm 2 grade.

[0149] See also Figure 8 and Fig. 9 , Figure 8 The EQE test results of the specific embodiment P1:Q3 of the organic optoelectronic component of the present invention are shown. Fig. 9 The dark current test results of the specific embodiment P1:Q3 of the organic optoelectronic component of the present invention are shown. Figure 8 As shown, the EQE response of the organic photoelectric component prepared by P1:Q3 can reach 2.4% at 1050nm under -5V bias and 40.4% at -20V bias; 2.1% at 1350nm under -5V bias and 37.5% under -20V bias. It can be seen that the organic photoelectric component prepared by P1:Q3 has the phenomenon that the EQE increases with the increase of bias. This phenomenon means that the organic photoelectric component prepared by P1:Q3 has the effect of photomultiplication. Fig. 9 As shown, the dark current is shown at -1V at 10 -7 A / cm 2 Level, -2V to -2.5V performance is 10 -6 A / cm 2 grade.

[0150] Table 2: Comparison of specific embodiments P2:Q2 and P1:Q3 of the organic optoelectronic components of the present invention with the prior art

[0151]

[0152]

[0153] Please refer to Table 2. Compared with the EQE response performance reported in the current literature at 1050nm, at 1350nm, the EQE response of the organic optoelectronic device prepared by P2:Q2 can reach 12.0%, and the dark current is 10 -5 A / cm 2 Level; P1:Q3 The EQE response of the organic photoelectric component prepared has a photomultiplier effect of up to 40.4% and a dark current of 10 -6 A / cm 2 Level. It can be seen that, compared with the prior art, the specific embodiments P2:Q2 and P1:Q3 of the organic optoelectronic components of the present invention have good performance in EQE and dark current. Furthermore, the EQE of the organic optoelectronic components of the present invention can also respond at -10V and -20V, which means that the organic optoelectronic components of the present invention have a wide range of voltage tolerance. In addition, compared with the prior art, the low energy gap small molecule material developed by the present invention has good solubility in non-halogen solvents, and non-halogen solvents (environmentally friendly solvents) can be used for coating processes.

[0154] Table 3: Comparison of specific embodiments P2:Q2 and P1:Q3 of the organic optoelectronic components of the present invention with the prior art

[0155]

[0156]

[0157] Please refer to Table 3. Compared with the EQE response performance reported in the current literature at 1350nm, the EQE response of the organic optoelectronic device prepared by P2:Q2 can reach 7.9% at 1350nm, and the dark current is 10 -5 A / cm 2 Grade; P1:Q3 The EQE response of the organic photoelectric component prepared has a photomultiplier effect of up to 37% and a dark current of 10 -6 A / cm 2 Level. It can be seen that, compared with the prior art, the specific embodiments P2:Q2 and P1:Q3 of the organic optoelectronic components of the present invention have good performance in EQE and dark current. Furthermore, the EQE of the organic optoelectronic components of the present invention can also respond at -10V and -20V, which means that the organic optoelectronic components of the present invention have a wide range of voltage tolerance. In addition, compared with the prior art, the low energy gap small molecule material developed by the present invention has good solubility in non-halogen solvents, and non-halogen solvents (environmentally friendly solvents) can be used for coating processes.

[0158] Based on the above experimental results, the low energy gap small molecule material of the present invention is not only soluble in non-halogen solvents (environmentally friendly solvents), but also has a light absorption range of more than 1000nm. In addition, the organic optoelectronic device prepared with this low energy gap small molecule material has good EQE and dark current performance at 1050nm and 1350nm.

[0159] It should be noted that if the substituents in the above specification are not explicitly stated, the substituents are independently selected from one of the following groups: C1-C30 alkyl, C3-C30 branched alkyl, C1-C30 silyl, C2-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 olefin, C2-C30 alkyne, C2-C30 carbon chain containing cyano, C1-C30 carbon chain containing nitro, C1-C30 carbon chain containing hydroxyl, C3-C30 carbon chain containing keto, halogen, cyano and hydrogen atom.

[0160] Through 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 scope that the present invention intends to apply for.

[0161] Explanation of symbols

[0162] 1: Organic optoelectronic components

[0163] 10: Substrate

[0164] 11: First electrode

[0165] 12: First carrier transfer layer

[0166] 13: Active layer

[0167] 14: Second carrier transfer layer

[0168] 15: Second electrode

Claims

1. A low energy gap small molecule material comprising a structure of formula 1: wherein m and n are independently selected from any integer between 0 and 2, x and y are 0, and o and p are 1; Ar 0 ,Ar 1 with Ar 2 They may be the same or different from each other, and the Ar 0 , each Ar 1 With each Ar 2 Independently selected from one of the following groups: The R 0 They can be the same or different from each other, and each R 0 independently selected from one of the following groups: C1-C30 alkyl, C3-C30 branched alkyl, C1-C30 silyl, C2-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 olefin, C2-C30 alkyne, C2-C30 carbon chain containing cyano, C1-C30 carbon chain containing nitro, C1-C30 carbon chain containing hydroxyl, C3-C30 carbon chain containing keto, halogen, cyano, hydrogen, having one or more R 1 Substituents and unsubstituted aromatic rings, having one or more R 1 Substituted and unsubstituted heterocyclic rings, having one or more R 1 A fused ring having a substituent and no substituent, having one or more R 1 Substituted and unsubstituted fused heterocyclic rings, these R 1 The substituents may be the same or different from each other, and each R 1 The substituents are independently selected from one of the following groups: C1-C30 alkyl groups, C3-C30 branched alkyl groups, C1-C30 silyl groups, C2-C30 ester groups, C1-C30 alkoxy groups, C1-C30 alkylthio groups, C1-C30 haloalkyl groups, C2-C30 olefins, C2-C30 alkynes, C2-C30 carbon chains containing cyano groups, C1-C30 carbon chains containing nitro groups, C1-C30 carbon chains containing hydroxyl groups, C3-C30 carbon chains containing keto groups, halogens, cyano groups and hydrogen atoms; Each A 0 They can be the same or different from each other, and each A 0 Independently selected from one of the following groups: and Where z is any integer from 1 to 8; Ar 3 with Ar 4 Independently selected from the following groups: having one or more R 2 A substituted or unsubstituted aromatic ring having one or more R 2 A substituted or unsubstituted heterocyclic ring having one or more R 2 A fused ring having a substituent or no substituent, and having one or more R 2 a substituted or unsubstituted fused heterocyclic ring; and Ar 5 Independently selected from one of the following groups: C1-C30 alkyl, C3-C30 branched alkyl, C1-C30 silyl group, C2-C30 ester group, C1-C30 alkoxy group, C1-C30 alkylthio group, C1-C30 haloalkyl group, C2-C30 olefin, C2-C30 alkyne, C2-C30 carbon chain containing cyano group, C1-C30 carbon chain containing nitro group, C1-C30 carbon chain containing hydroxyl group, C3-C30 carbon chain containing keto group, halogen, cyano group, hydrogen atom, one or more R 3 A substituted or unsubstituted aromatic ring having one or more R 3 A substituted or unsubstituted heterocyclic ring having one or more R 3 A fused ring having a substituent or no substituent, and having one or more R 3 a fused heterocyclic ring which may or may not have a substituent; in, These R in each structure 2 And these R 3 They can be the same or different from each other, and each R 2 And each R 3 One independently selected from the following groups: C1-C30 alkyl, C3-C30 branched alkyl, C1-C30 silyl, C2-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 olefin, C2-C30 alkyne, C2-C30 carbon chain containing cyano, C1-C30 carbon chain containing nitro, C1-C30 carbon chain containing hydroxyl, C3-C30 carbon chain containing keto, halogen, cyano and hydrogen atom; as well as Among these A in the structure of formula 1 1 They can be the same or different from each other, and each A 1 Independently selected from one of the following groups: These R 4 They can be the same or different from each other, and each R 4 Independently selected from one of the following groups: C1-C30 alkyl, C3-C30 branched alkyl, C1-C30 silyl, C2-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C2-C30 olefin, C2-C30 alkyne, C2-C30 carbon chain containing cyano, C1-C30 carbon chain containing nitro, C1-C30 carbon chain containing hydroxyl, C3-C30 carbon chain containing keto, halogen, cyano and hydrogen atom. 2 . The low energy gap small molecule material as claimed in claim 1 , wherein m=n, o=p, and x=y in the structure of formula 1.

3. The low energy gap small molecule material as claimed in claim 1, wherein Ar in the structure of formula 1 1 =Ar 2 . The low energy gap small molecule material as claimed in claim 1 , wherein m+n+o+p≠0 in the structure of formula 1.

5. An organic optoelectronic component, comprising: A first electrode comprising a transparent electrode; a first carrier transport layer; An active layer comprising at least one low energy gap small molecule material as claimed in claim 1; a second carrier transport layer; and The second electrode, wherein the first carrier transfer layer is located between the first electrode and the active layer, the active layer is located between the first carrier transfer layer and the second carrier transfer layer, and the second carrier transfer layer is located between the active layer and the second electrode.

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