Organic compounds, thin films and methods for their preparation, optoelectronic devices, display devices

Abstract

The application discloses an organic compound, a thin film and a preparation method thereof, an optoelectronic device and a display device, and relates to the technical field of display. A structural formula of the organic compound is shown in the following formula: the cross-linking temperature of the organic compound provided by the application is relatively low.

Description

Technical Field

[0001] This application relates to the field of display technology, and in particular to an organic compound, a thin film and its preparation method, an optoelectronic device, and a display apparatus. Background Technology

[0002] In related technologies, crosslinkable organic compounds have excellent thermal stability, solvent resistance, and easy solution handling. However, the crosslinking temperature of existing organic compounds is too high, which affects the performance of the organic compounds and still needs further improvement. Summary of the Invention

[0003] In view of this, this application provides an organic compound, a thin film and a method for preparing the same, an optoelectronic device, and a display device.

[0004] The embodiments of this application are implemented as follows: an organic compound, the structural formula of which is shown below:

[0005]

[0006] Among them, L1 and L2 are each independently selected from single-bonded, substituted, or unsubstituted C1 to C2 bonds. 40 Alkylene, substituted or unsubstituted C2-C 20 Etheryl group, substituted or unsubstituted arylene group, substituted or unsubstituted aryleneoxy group, substituted or unsubstituted arylene thio group, substituted or unsubstituted -(CH2) n1 CO(CH2) n2 -, substituted or unsubstituted -(CH2) n3 NHCO(CH2) n4 -, substituted or unsubstituted -(CH2) n5 CONH(CH2) n6 -, substituted or unsubstituted -(CH2) n7 COO(CH2) n8 -, substituted or unsubstituted -(CH2) n9 One or more combinations of C(NH)-; wherein n1 to n9 are each independently selected from integers from 1 to 20;

[0007] R1, R2, R3, and R4 are each independently selected from H, D, halogen, cyano, hydroxyl, carboxyl, aldehyde, nitro, unsubstituted or substituted with -D, -NH2, -F, -Cl, -Br, -I, -OH, -COOH, -NO2, -SO3H, -CHO, -SH, or -CN, belonging to the C1-C group. 10 alkyl.

[0008] Accordingly, embodiments of this application also provide a thin film, the material of which includes the aforementioned organic compounds.

[0009] Accordingly, embodiments of this application also provide a method for preparing a thin film, comprising the following steps:

[0010] Provide the aforementioned organic compounds;

[0011] The organic compound is deposited and heated to obtain a thin film.

[0012] Accordingly, this application also provides an optoelectronic device, comprising an anode, a hole-functional layer, an active layer, and a cathode stacked sequentially; wherein the hole-functional layer comprises the thin film described above, or a thin film prepared by the above-described preparation method.

[0013] Accordingly, this application also provides a display device, which includes the above-mentioned optoelectronic device.

[0014] The organic compounds provided in this application have a low crosslinking temperature. Attached Figure Description

[0015] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0016] Figure 1 This is a flowchart of a method for preparing an organic material provided in an embodiment of this application;

[0017] Figure 2 This is a flowchart of a method for preparing a thin film provided in an embodiment of this application;

[0018] Figure 3 This is a schematic diagram of the structure of an optoelectronic device provided in an embodiment of this application;

[0019] Figure 4 This is a schematic diagram of the structure of another optoelectronic device provided in the embodiments of this application.

[0020] Figure label:

[0021] Optoelectronic devices 100;

[0022] Anode 20; Hole functional layer 10; Hole injection layer 11; Hole transport layer 12; Active layer 30; Cathode 40; Electron functional layer 50. Detailed Implementation

[0023] The technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of this application, and not all embodiments. Based on the embodiments of this application, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this application. Furthermore, it should be understood that the specific embodiments described herein are only for illustration and explanation of this application and are not intended to limit this application.

[0024] In this application, unless otherwise stated, directional terms such as "upper" and "lower" generally refer to the upper and lower positions of the device in its actual use or operating state, specifically the orientation shown in the accompanying drawings; while "inner" and "outer" refer to the outline of the device. Furthermore, in the description of this application, the term "comprising" means "including but not limited to". The terms first, second, third, etc., are used merely as illustrative purposes and do not impose numerical requirements or establish a numerical order.

[0025] In this application, "and / or" describes the relationship between related objects, indicating that three relationships can exist. For example, A and / or B can represent: A existing alone, A and B existing simultaneously, or B existing alone. A and B can be singular or plural.

[0026] In this application, "at least one" means one or more, and "more than one" means two or more. "One or more", "at least one of the following", or similar expressions refer to any combination of these items, including any combination of single or multiple items. For example, "at least one of a, b, or c", or "at least one of a, b, and c", can both mean: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, and c can be single or multiple.

[0027] Various embodiments of this application may exist in the form of a range; it should be understood that the description in the form of a range is merely for convenience and brevity and should not be construed as a hard limitation on the scope of this application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single numerical values ​​within that range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., and single numbers within the range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. Furthermore, whenever a numerical range is referred to herein, it means including any referenced number (fraction or integer) within the referred range.

[0028] In this application, "substituted or unsubstituted" means that the defined group may or may not be substituted. It is understood that when the group is substituted by a substituent, the number of substituents may be one, two, three or more, and when the number of substituents is two or more, the substituents may be the same or different.

[0029] In this application, "alkyl" can mean straight-chain, branched, and / or cyclic alkyl. The number of carbon atoms in an alkyl group can be 1 to 30, 1 to 25, 1 to 20, 1 to 15, 1 to 10, or 1 to 6. Phrases containing this term, such as "C1-C", are also included. 10 "Alkyl" refers to an alkyl group containing 1 to 10 carbon atoms. Each time it appears, it can independently be C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, C9 alkyl, or C 10 Alkyl groups. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyl 2-Hexyldecyl, 2-Octylide, n-Undecyl, n-Dodecyl, 2-Ethyldodecyl, 2-Butyldodecyl, 2-Hexyldodecyl, 2-Octylide, n-Tridecyl, n-Tetradecyl, n-Pentadedecyl, n-Hexadecyl, 2-Ethylhexadecyl, 2-Butylhexadecyl, 2-Hexylhexadecyl, 2-Octylide, n-Heptadedecyl, n-Octadedecyl, n-Nondecyl, n-Eicosyl, 2-Ethyleicosyl, 2-Butyleicosyl, 2-Hexyleicosyl, 2-Octylide, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, etc.

[0030] Currently, optoelectronic devices are electron-injection-biased devices, meaning that electron injection is excessive. Improving the hole transport capability of hole transport materials is crucial for regulating the charge balance and improving the efficiency of optoelectronic devices. There are two main approaches to address this issue: firstly, providing hole transport materials with deeper HOMO levels that can effectively match the valence band of the emissive layer material, thus lowering the hole injection barrier and facilitating greater hole injection; secondly, providing materials with higher hole mobility to promote efficient hole transport. Existing hole transport materials require excessively high heat treatment temperatures for crosslinking, typically exceeding 200°C. However, materials for the hole injection layer, such as poly(3,4-ethylenedioxythiophene)-polystyrene sulfonic acid (PEDOT:PSS), located between the anode and hole transport layer, typically have a heat treatment temperature of only 150°C. Excessively high heat treatment temperatures for the hole transport layer can lead to instability or even decomposition of the hole injection layer material, causing carrier imbalance and energy level mismatch, resulting in decreased device performance.

[0031] 4,4'-Di(9-carbazole)biphenyl (CBP) is a hole transport material in the prior art. It has a deep HOMO energy level and a high hole mobility. However, its crosslinking temperature is around 210℃. This high crosslinking temperature will damage other film layers, and the density of the film after crosslinking treatment is poor, resulting in poor photoelectric efficiency and lifespan of optoelectronic devices.

[0032] The technical solution of this application is as follows:

[0033] In a first aspect, embodiments of this application provide an organic compound, the structural formula of which is shown below:

[0034]

[0035] Among them, L1 and L2 are each independently selected from single-bonded, substituted, or unsubstituted C1 to C2 bonds. 40 Alkylene, substituted or unsubstituted C2-C 20 Etheryl group, substituted or unsubstituted arylene group, substituted or unsubstituted aryleneoxy group, substituted or unsubstituted arylene thio group, substituted or unsubstituted -(CH2) n1 CO(CH2) n2 -, substituted or unsubstituted -(CH2) n3 NHCO(CH2) n4 -, substituted or unsubstituted -(CH2) n5 CONH(CH2) n6 -, substituted or unsubstituted -(CH2) n7 COO(CH2) n8 -, substituted or unsubstituted -(CH2) n9One or more combinations of C(NH)-; wherein n1 to n9 are each independently selected from integers from 1 to 20;

[0036] R1, R2, R3, and R4 are each independently selected from H, D, halogen, cyano, hydroxyl, carboxyl, aldehyde, nitro, unsubstituted or substituted with -D, -NH2, -F, -Cl, -Br, -I, -OH, -COOH, -NO2, -SO3H, -CHO, -SH, or -CN, belonging to the C1-C group. 10 alkyl.

[0037] It can be understood that the structural formula of CBP material is as follows: The organic compounds provided in this application are modified groups. The material obtained after modifying CBP material.

[0038] The organic compound provided in this application modifies 4,4'-bis(9-carbazole)biphenyl (CBP) material. The conjugation effect between the modified group and the original benzene ring in the CBP material allows the bond angle between the modified group and the benzene ring to vary within a certain range, increasing the flexibility of the organic compound. Furthermore, the modified group has a shorter chain length, weaker intermolecular interactions, and less steric hindrance, making the organic compound more prone to deformation and movement under external forces, thus exhibiting higher flexibility. After modification, the modified group allows the organic compound to maintain good flowability and solubility before the crosslinking reaction, helping to lower the temperature required for the crosslinking reaction. Simultaneously, since the crosslinking reaction mainly occurs between alkenyl groups connected to -R1, -R2, -R3, and -R4 in the organic compound, the rate and extent of the crosslinking reaction can be controlled by adjusting the length and properties of the modified group, further reducing the crosslinking temperature, increasing hole mobility, promoting hole-electron balance, and improving the uniformity and density of the film prepared from the organic compound.

[0039] In some embodiments, R1, R2, R3, and R4 may be the same or different.

[0040] In some embodiments, L1 and L2 may be the same or different.

[0041] Preferably, R1 and R3 are the same, R2 and R4 are the same, and L1 and L2 are the same. This facilitates the preparation of CBP materials modified by the modifying groups.

[0042] In some embodiments, L1 and L2 are each independently selected from single-bonded, substituted, or unsubstituted C1 to C2 bonds. 20 Alkylene, substituted or unsubstituted C2-C 10 Etheryl group, substituted or unsubstituted arylene group, substituted or unsubstituted aryleneoxy group, substituted or unsubstituted arylene thio group, substituted or unsubstituted -(CH2)n1 CO(CH2) n2 -, substituted or unsubstituted -(CH2) n3 NHCO(CH2) n4 -, substituted or unsubstituted -(CH2) n5 CONH(CH2) n6 -, substituted or unsubstituted -(CH2) n7 COO(CH2) n8 -, substituted or unsubstituted -(CH2) n9 One or more combinations of C(NH)-; wherein n1 to n9 are each independently selected from integers from 1 to 10.

[0043] In some embodiments, L1 and L2 are each independently selected from single-bonded, substituted, or unsubstituted C1 to C2 bonds. 10 Alkylene, substituted or unsubstituted C2–C8 etherene, substituted or unsubstituted arylene, substituted or unsubstituted aryleneoxy, substituted or unsubstituted arylenethio, substituted or unsubstituted -(CH2) n1 CO(CH2) n2 -, substituted or unsubstituted -(CH2) n3 NHCO(CH2) n4 -, substituted or unsubstituted -(CH2) n5 CONH(CH2) n6 -, substituted or unsubstituted -(CH2) n7 COO(CH2) n8 -, substituted or unsubstituted -(CH2) n9 One or more combinations of C(NH)-; wherein n1 to n9 are each independently selected from integers from 1 to 8.

[0044] In some embodiments, L1 and L2 are each independently selected from substituted or unsubstituted C1 to C5 alkylene groups.

[0045] In some embodiments, R1, R2, R3, and R4 are each independently selected from H, D, halogen, cyano, hydroxyl, carboxyl, aldehyde, nitro, unsubstituted or substituted C1-C8 alkyl groups with -D, -NH2, -F, -Cl, -Br, -I, -OH, -COOH, -NO2, -SO3H, -CHO, -SH, or -CN.

[0046] In some embodiments, R1, R2, R3, and R4 are each independently selected from H, D, halogen, cyano, hydroxyl, carboxyl, aldehyde, and nitro.

[0047] In some embodiments, R1 and R3 are selected from H. R2 and R4 are selected from hydroxyl groups.

[0048] In some embodiments, the crosslinking temperature of the organic compound is 130°C to 155°C, for example, it can be 132°C, 135°C, 138°C, 140°C, 142°C, 145°C, 148°C, 150°C, 152°C, or any range between two values. Within the range of the crosslinking temperature, it is beneficial for the organic compound to crosslink without damaging other film layers.

[0049] In some embodiments, the HOMO energy level of the organic compound is -6.35 eV to -6.20 eV, for example, it can be -6.35 eV, -6.32 eV, -6.30 eV, -6.28 eV, -6.25 eV, -6.22 eV, -6.20 eV, or any range between two values. The LUMO energy level of the organic compound is -2.97 eV to -2.90 eV, for example, it can be -2.97 eV, -2.96 eV, -2.95 eV, -2.94 eV, -2.96 eV, -2.92 eV, -2.91 eV, -2.90 eV, or any range between two values. Within the energy level range of the organic compound, it is beneficial for the organic compound to achieve energy level matching with the quantum dots in the active layer 30 when applied to the hole transport layer 12, thereby improving the hole injection efficiency.

[0050] In some embodiments, the organic compound is selected from compounds having the following structural formula:

[0051]

[0052] Please see Figure 1 This application also provides a method for preparing an organic compound, the synthetic route of which is as follows:

[0053]

[0054] The preparation method of organic compounds specifically includes the following steps:

[0055] S11. 4,4'-bis(9-carbazole)biphenyl and an amide compound are mixed and reacted to give a first intermediate product; the structural formula of the first intermediate product is shown below:

[0056]

[0057] S12. A reducing agent is provided, and the reducing agent and the first intermediate product are mixed and reacted to obtain a second intermediate product; the structural formula of the second intermediate product is shown below:

[0058]

[0059] S13. Provide a modifier, mix the modifier and the second intermediate product, and react to obtain an organic compound;

[0060] The structural formula of the modifier is shown below:

[0061]

[0062] The structural formula of the organic compound is shown below:

[0063]

[0064] Wherein, X1 and X2 are selected from halogen groups;

[0065] L1 and L2 are each independently selected from single-bonded, substituted, or unsubstituted C1 to C2. 40 Alkylene, substituted or unsubstituted C2-C 20 Etheryl group, substituted or unsubstituted arylene group, substituted or unsubstituted aryleneoxy group, substituted or unsubstituted arylene thio group, substituted or unsubstituted -(CH2) n1 CO(CH2) n2 -, substituted or unsubstituted -(CH2) n3 NHCO(CH2) n4 -, substituted or unsubstituted -(CH2) n5 CONH(CH2) n6 -, substituted or unsubstituted -(CH2) n7 COO(CH2) n8 -, substituted or unsubstituted -(CH2) n9 One or more combinations of C(NH)-; wherein n1 to n9 are each independently selected from integers from 1 to 20;

[0066] R1, R2, R3, and R4 are each independently selected from H, D, halogen, cyano, hydroxyl, carboxyl, aldehyde, nitro, unsubstituted or substituted with -D, -NH2, -F, -Cl, -Br, -I, -OH, -COOH, -NO2, -SO3H, -CHO, -SH, or -CN, belonging to the C1-C group. 10 alkyl.

[0067] In S11:

[0068] In some embodiments, the structural formula of the amide compound is: R5 and R6 are each independently selected from H, D, halogen, cyano, hydroxyl, carboxyl, aldehyde, nitro, unsubstituted or substituted with -D, -NH2, -F, -Cl, -Br, -I, -OH, -COOH, -NO2, -SO3H, -CHO, -SH, -CN, C1-C 10 alkyl.

[0069] Specifically, the amide compound may be N,N-dimethylformamide (DMF).

[0070] In some embodiments, the molar ratio of the 4,4'-bis(9-carbazole)biphenyl to the amide compound is 1:(20-25), for example, it can be 1:20.5, 1:21, 1:21.5, 1:22, 1:22.5, 1:23, 1:23.5, 1:24, 1:24.5, or any range between two ratios. It should be noted that the benzene ring on the 4,4'-bis(9-carbazole)biphenyl has a stable structure and relatively low reactivity, requiring a larger amount of amide compound to improve reaction efficiency and yield.

[0071] In some embodiments, the mixing of the 4,4'-bis(9-carbazole)biphenyl and the amide compound further includes the addition of a first solvent.

[0072] Further, the first solvent includes one or more of chlorobenzene, tetrahydrofuran, n-octane, isooctane, n-hexane, cyclohexane, ethyl acetate, benzene, toluene, chloroform, carbon tetrachloride, dichloromethane, dimethyl ether, tetraethylene glycol dimethyl ether, N,N-dimethylformamide, ethyl acetate, pyrrole, butyric acid, and cresol.

[0073] The mass concentration of the 4,4'-bis(9-carbazole)biphenyl in the first solvent is 50 mg / mL to 80 mg / mL, for example, it can be 55 mg / mL, 60 mg / mL, 65 mg / mL, 70 mg / mL, 75 mg / mL, or any range between two values. Within this mass concentration range, the dissolution and dispersion of the 4,4'-bis(9-carbazole)biphenyl are favorable, and a suitable reaction environment is provided.

[0074] In some embodiments, the mixing of the 4,4'-bis(9-carbazole)biphenyl and the amide compound further includes the addition of a first catalyst.

[0075] Furthermore, the first catalyst includes one or more of POCl3, SOCl2, and ZnCl2.

[0076] The molar ratio of the amide compound to the first catalyst is (1-2):(1-2), for example, it can be 1:1, 1:1.2, 1:1.5, 1:1.8, 1:2, 1.2:1, 1.5:1, 1.8:1, 2:1, or any range between two ratios. The catalyst can promote the reaction between the amide compound and 4,4'-bis(9-carbazole)biphenyl.

[0077] In some embodiments, the reaction temperature of the mixture of 4,4'-bis(9-carbazole)biphenyl and the amide compound is 95°C to 100°C, for example, 96°C, 97°C, 98°C, 99°C, or any range between two values; the reaction time is 10h to 12h, for example, 10.5h, 11h, 11.5h, or any range between two values. Thus, under these reaction conditions, a formylation reaction is favored between the 4,4'-bis(9-carbazole)biphenyl and the amide compound, forming an aldehyde group on the benzene ring of the 4,4'-bis(9-carbazole)biphenyl.

[0078] In S12:

[0079] In some embodiments, the reducing agent includes NaBH4, LiAlH4, and NaHSO3.

[0080] In some embodiments, the molar ratio of the first intermediate product to the reducing agent is 1:(1.2 to 1.5), for example, it can be 1:1.25, 1:1.3, 1:1.35, or any range between two ratios. Under the conditions of the molar ratio, it is advantageous for the reducing agent to reduce the aldehyde group on the first intermediate product to a hydroxyl group.

[0081] In some embodiments, mixing the reducing agent and the first intermediate product further includes adding a second solvent.

[0082] Further, the second solvent includes one or more of chlorobenzene, tetrahydrofuran, n-octane, isooctane, n-hexane, cyclohexane, ethyl acetate, benzene, toluene, chloroform, carbon tetrachloride, dichloromethane, dimethyl ether, tetraethylene glycol dimethyl ether, N,N-dimethylformamide, ethyl acetate, pyrrole, butyric acid, and cresol.

[0083] The mass concentration of the first intermediate product in the second solvent is 20 mg / mL to 30 mg / mL, for example, it can be 22 mg / mL, 24 mg / mL, 25 mg / mL, 26 mg / mL, 28 mg / mL, or any range between two values. Within this mass concentration range, the dissolution and dispersion of the first intermediate product are favorable, and a suitable reaction environment is provided.

[0084] In some embodiments, the reaction temperature of the reducing agent and the first intermediate product is 25°C to 28°C, for example, 25.5°C, 26°C, 26.5°C, 27°C, 27.5°C, or any range between two values; the reaction time is 20h to 24h, for example, 21h, 22h, 23h, or any range between two values. Thus, under these reaction conditions, a reduction reaction is favored between the reducing agent and the first intermediate product, reducing the aldehyde group on the first intermediate product to a hydroxyl group.

[0085] It should be noted that during the reaction of the reducing agent and the first intermediate product, other reagents, such as hydroxyl protecting agents (e.g., ethanol), can be added as needed to protect the hydroxyl groups on the second intermediate product. After the reaction, a reagent (e.g., water) can be added to dissolve the byproducts (e.g., NaBO2) and a base (e.g., NaOH) can be added to adjust the pH of the solution to prevent the formation of boric acid solid under acidic conditions. This facilitates subsequent removal of impurities and purification of the second intermediate product.

[0086] In S13:

[0087] In some embodiments, the halogen group is selected from -Cl, -Br, and -I.

[0088] The selection of L1, L2, R1, R2, R3, and R4 can be found above and will not be repeated here.

[0089] In some embodiments, the modifier is selected from one or more compounds having the following structural formula:

[0090]

[0091] In some embodiments, the molar ratio of the second intermediate to the modifier is 1:(1-4), for example, it can be 1:1, 1:1.5, 1:2, 1:2.5, 1:3, 1:3.5, 1:4, or any range between two ratios. Under the conditions of the molar ratio described above, it is beneficial for the second intermediate to react with the modifier.

[0092] In some embodiments, mixing the modifier and the second intermediate product further includes adding a third solvent.

[0093] Further, the third solvent includes one or more of chlorobenzene, tetrahydrofuran, n-octane, isooctane, n-hexane, cyclohexane, ethyl acetate, benzene, toluene, chloroform, carbon tetrachloride, dichloromethane, dimethyl ether, tetraethylene glycol dimethyl ether, N,N-dimethylformamide, ethyl acetate, pyrrole, butyric acid, and cresol.

[0094] The second intermediate product has a mass concentration of 20 mg / mL to 40 mg / mL in the third solvent, for example, it can be 22 mg / mL, 25 mg / mL, 28 mg / mL, 30 mg / mL, 32 mg / mL, 35 mg / mL, 38 mg / mL, or any range between two values. Within this mass concentration range, the dissolution and dispersion of the second intermediate product are favorable, and a suitable reaction environment is provided.

[0095] In some embodiments, the mixing of the modifier and the second intermediate product further includes the addition of a second catalyst.

[0096] Furthermore, the second catalyst includes NaH.

[0097] The molar ratio of the second intermediate to the second catalyst is 1:(2-4), for example, it can be 1:2, 1:2.2, 1:2.5, 1:2.8, 1:3, 1:3.2, 1:3.5, 1:3.8, or any range between two ratios. The catalyst can promote the reaction between the modifier and the second intermediate.

[0098] In some embodiments, the reaction temperature of the modifier and the second intermediate product is 50°C to 70°C, for example, 52°C, 55°C, 58°C, 60°C, 62°C, 65°C, 68°C, or any range between two values; the reaction time is 20h to 28h, for example, 21h, 22h, 23h, 24h, 25h, 26h, 27h, or any range between two values. Thus, under these reaction conditions, it is beneficial for the reaction between the modifier and the second intermediate product to occur, thereby introducing the modifier onto the second intermediate product.

[0099] Secondly, embodiments of this application also provide a thin film, the material of which includes the above-mentioned organic compounds, or includes organic compounds prepared by the above-mentioned preparation method.

[0100] It should be noted that the organic compounds in the film are cross-linked.

[0101] In some embodiments, the thickness of the film is 10nm to 40nm, for example, it can be 15nm, 20nm, 25nm, 30nm, 35nm or any range between two values.

[0102] In some embodiments, the surface roughness of the thin film is 2.2 nm to 5.1 nm, for example, it can be 2.5 nm, 3 nm, 3.5 nm, 4 nm, 4.5 nm, or any range between two values. Within the range of surface roughness, the thin film has good film-forming properties and high density, which is beneficial to the continuity of electrical conductivity.

[0103] The thin film can be achieved using conventional techniques in the art, such as chemical or physical methods. Chemical methods include chemical vapor deposition, continuous ion layer adsorption and reaction, anodic oxidation, electrolytic deposition, and co-precipitation. Physical methods include physical deposition and solution methods. Physical deposition methods include thermal evaporation deposition, electron beam evaporation deposition, magnetron sputtering, multi-arc ion deposition, physical vapor deposition, atomic layer deposition, pulsed laser deposition, etc.; solution methods include spin coating, printing, inkjet printing, blade coating, dip coating, immersion coating, spraying, roller coating, casting, slot coating, and strip coating, etc.

[0104] Thirdly, please refer to Figure 2 This application also provides a method for preparing a thin film, comprising the following steps:

[0105] S21. Provide the organic compound;

[0106] S22. Deposit the organic compound; heat to obtain a thin film.

[0107] In some embodiments, depositing the organic compound includes: providing an organic compound dispersion comprising the organic compound, and depositing the organic compound dispersion.

[0108] In some embodiments, the organic compound dispersion has a mass concentration of 10 mg / mL to 60 mg / mL, for example, it can be 15 mg / mL, 20 mg / mL, 25 mg / mL, 30 mg / mL, 35 mg / mL, 40 mg / mL, 45 mg / mL, 50 mg / mL, 55 mg / mL, or any range between two values. Within this mass concentration range, the dissolution and dispersion of the organic compound are favorable.

[0109] In some embodiments, the organic compound dispersion further includes a solvent, which includes one or more of n-octane, isooctane, n-hexane, cyclohexane, ethyl acetate, benzene, toluene, chloroform, carbon tetrachloride, dichloromethane, dimethyl ether, and tetraethylene glycol dimethyl ether.

[0110] In some embodiments, the heating temperature is 130°C to 155°C, for example, it can be 132°C, 135°C, 138°C, 140°C, 142°C, 145°C, 148°C, 150°C, 152°C, or any range between two values; the heating time is 30 min to 40 min, for example, it can be 31 min, 32 min, 33 min, 34 min, 35 min, 36 min, 37 min, or any range between two values. Thus, under the heating conditions described above, it is beneficial to promote the cross-linking of the organic compound and to facilitate the film formation of the organic compound, thereby improving the density of the film.

[0111] Fourthly, please refer to Figure 3 This application also provides an optoelectronic device 100, comprising an anode 20, a hole functional layer 10, an active layer 30 and a cathode 40 stacked sequentially; wherein the hole functional layer 10 comprises the above-described thin film, or comprises a thin film prepared by the above-described preparation method.

[0112] In the optoelectronic device 100 provided in this application, organic compounds are applied to the hole functional layer 10 of the optoelectronic device 100. This reduces the crosslinking temperature, avoids the influence of the crosslinking of the hole functional layer 10 on other film layers, promotes hole injection and transport, and the organic compounds have high flexibility, making them suitable for flexible devices. Furthermore, it improves the density and uniformity of the hole functional layer 10. In summary, the optoelectronic device 100 provided in this application has high luminous efficiency and a long service life.

[0113] Please see Figure 3 The hole functional layer 10 includes one or more of a hole injection layer 11 and a hole transport layer 12, wherein the hole injection layer 11 is located between the anode 20 and the hole transport layer 12.

[0114] In some embodiments, the hole transport layer 12 comprises the thin film. In other words, the material of the hole transport layer 12 comprises the organic material.

[0115] In some embodiments, the thickness of the hole transport layer 12 is 10nm to 20nm, for example, it can be 12nm, 14nm, 15nm, 16nm, 18nm, etc.

[0116] In some embodiments, the hole injection layer 11 is made of an organic P-type semiconductor material or an inorganic P-type semiconductor material. The organic P-type semiconductor material includes 4,4'-N,N'-dicarbazolyl-biphenyl, N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4”-diamine, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-spiro, N,N'- bis(4-(N,N'-diphenyl-amino)phenyl)-N,N'-diphenylbenzidine, 4,4',4'-tris(N-carbazolyl)-triphenylamine, 4,4',4'-tris(carbazol-9-yl)triphenylamine, trichloroisocyanuric acid, terbium-doped phosphate-based green luminescent materials, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene, 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, poly[(9,9'-dioctylfluorene-2,7-diyl)-co-(4, 4'-(N-(4-sec-butylphenyl)diphenylamine)], poly(4-butylphenyl-diphenylamine), poly[bis(4-phenyl)(4-butylphenyl)amine], polyaniline, polypyrrole, poly(p-)phenylenevinylene, poly(phenylenevinylene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene], poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene], copper phthalocyanine, aromatic tertiary amines, polynuclear aromatic tertiary amines, 4,4'-bis(p-carbazolyl)-1, 1'-Biphenyl compounds, N,N,N',N'-tetraarylbenzidine, PEDOT, PEDOT:PSS and its derivatives, PEDOT:PSS derivatives doped with s-MoO3, poly(N-vinylcarbazole) and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, poly(spirofluorene) and its derivatives, N,N'-di(naphthyl-1-yl)-N,N'-diphenylbenzidine, spiron NPB, nanocrystalline diamond, microcrystalline cellulose and tetracyanoquinone dimethane, doped graphene, undoped graphene;The inorganic P-type semiconductor material comprises one or more of the following: first doped metal oxide particles, first undoped metal oxide particles, metal sulfides, metal selenides, and metal nitrides. The metal oxides in the first doped metal oxide particles and the first undoped metal oxide particles each independently comprise one or more of MoO3, WO3, NiO, CrO3, CuO, and V2O5. The doping element in the first doped metal oxide particles comprises one or more of Mo, W, Ni, Cr, Cu, and V. The metal sulfides comprise CuS, MoS3, and WS. One or more of the following three elements are present: the metal selenide includes one or more of MoSe3 and WSe3; the metal nitride includes p-type gallium nitride; and the doping amount of the dopant element in the first doped metal oxide particle is 0.1 wt% to 20 wt%, for example, it can be 1 wt%, 2 wt%, 3 wt%, 4 wt%, 5 wt%, 6 wt%, 7 wt%, 8 wt%, 9 wt%, 10 wt%, 11 wt%, 12 wt%, 13 wt%, 14 wt%, 15 wt%, 16 wt%, 17 wt%, 18 wt%, 19 wt%, or any range between two values.

[0117] In some embodiments, the anode 20 and the cathode 40 each independently comprise one or more of a metal, a carbon material, and a metal oxide; the metal comprises one or more of Al, Ag, Cu, Mo, Au, Ba, Ca, Yb, and Mg; the carbon material comprises one or more of graphite, carbon nanotubes, graphene, and carbon fibers; the metal oxide comprises a metal oxide electrode or a composite electrode in which a metal is disposed between doped or undoped transparent metal oxides, the material of the metal oxide electrode comprising one or more of ITO, FTO, ATO, AZO, GZO, IZO, MZO, MoO3, and AMO; the composite electrode comprises one or more of AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, ZnS / Ag / ZnS, ZnS / Al / ZnS, TiO2 / Ag / TiO2, and TiO2 / Al / TiO2. In this context, " / " indicates a stacked structure. For example, AZO / Ag / AZO represents a composite electrode consisting of sequentially stacked AZO, Ag, and AZO layers.

[0118] In some embodiments, the optoelectronic device 100 includes a light-emitting diode.

[0119] In some embodiments, the active layer 30 includes a light-emitting layer, and the material of the light-emitting layer includes one or more of organic light-emitting materials and quantum dot light-emitting materials.

[0120] The organic light-emitting material may be selected from, but is not limited to, one or more of the following: CBP:Ir(mppy)3(4,4'-bis(N-carbazole)-1,1'-biphenyl:tris[2-(p-tolyl)pyridinium(III)]), TCTX:Ir(mmpy)(4,4',4”-tris(carbazole-9-yl)triphenylamine:tris[2-(p-tolyl)pyridinium(III)]), diaromatic anthracene derivatives, stilbene aromatic derivatives, pyrene derivatives, fluorene derivatives, TBPe fluorescent materials, TTPX fluorescent materials, TBRb fluorescent materials, DBP fluorescent materials, delayed fluorescent materials, TTA materials, TADF (thermally activated delayed) materials, polymers containing BN covalent bonds, HLCT (hybrid local charge transfer excited state) materials, and Exciplex (excitoplex) light-emitting materials.

[0121] The quantum dot luminescent material may be selected from, but is not limited to, one or more of single-structure quantum dots, core-shell structure quantum dots, and perovskite semiconductor materials.

[0122] The materials for the single-structure quantum dots, the core material of the core-shell quantum dots, and the shell material of the core-shell quantum dots can be selected from, but are not limited to, one or more compounds from group II-VI, group IV-VI, group III-V, and group I-III-VI. The shell of the core-shell quantum dots may consist of one or more layers. The group II-VI compounds may be selected from, but are not limited to, one or more of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and HgZnSTe. The IV-VI group compounds may be selected from, but are not limited to, one or more of SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, and SnPbSTe. The group III-V compounds may be selected from, but are not limited to, one or more of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and InAlPSb. The group I-III-VI compounds may be selected from, but are not limited to, one or more of CuInS2, CuInSe2, and AgInS2.

[0123] As an example, the core-shell structured quantum dots can be selected from, but are not limited to, one or more of CdSe / CdSeS / CdS, InP / ZnSeS / ZnS, CdZnSe / ZnSe / ZnS, CdSeS / ZnSeS / ZnS, CdSe / ZnS, CdSe / ZnSe / ZnS, ZnSe / ZnS, ZnSeTe / ZnS, CdSe / CdZnSeS / ZnS, and InP / ZnSe / ZnS. In the above descriptions of CdSe / ZnS, etc., the " / " indicates that the material after the " / " (as the shell) covers the material before the " / " (as the core).

[0124] The perovskite semiconductor material can be selected from, but is not limited to, doped or undoped inorganic perovskite semiconductors, or organic-inorganic hybrid perovskite semiconductors. The general structural formula of the inorganic perovskite semiconductor is AMX3, where A is Cs. + Ion, M is a divalent metal cation selected from Pb 2+ Sn 2+ Cu 2+ Ni 2+ Cd 2+ Cr 2+ Mn 2+ Co 2+ Fe 2+ 、Ge 2+ Yb 2+ Eu 2+ One or more of the following, where X is a halide anion selected from Cl... - ,Br - I - One or more of the following. The general structural formula of the organic-inorganic hybrid perovskite semiconductor is BMX3, where B is an organic amine cation selected from CH3(CH2). n-2 NH3 + Or [NH3(CH2)] n NH3] 2+ Where n≥2, M is a divalent metal cation selected from Pb 2+ Sn 2+ Cu 2+ Ni 2+ Cd 2+ Cr 2+ Mn 2+ Co 2+ Fe 2+ 、Ge 2+ Yb 2+ Eu 2+ One or more of the following, where X is a halide anion selected from Cl... - ,Br - I -One or more of them.

[0125] In some embodiments, the optoelectronic device 100 further includes an electronic functional layer 50 located between the active layer 30 and the cathode 40.

[0126] The electronic functional layer 50 includes one or more of an electron injection layer and an electron transport layer.

[0127] In some embodiments, the material of the electronic functional layer 50 includes one or more of the following: second doped metal oxide particles, second undoped metal oxide particles, group IIB-VIA semiconductor materials, group IIIA-VA semiconductor materials, and group IB-IIIA-VIA semiconductor materials. The material of the second undoped metal oxide particles includes one or more of ZnO, TiO2, SnO2, ZrO2, and Ta2O5. The metal oxide in the second doped metal oxide particles includes one or more of ZnO, TiO2, SnO2, ZrO2, Ta2O5, and Al2O3. The doping element in the second doped metal oxide particles includes one or more of Al, Mg, Li, Mn, Y, La, Cu, Ni, Zr, Ce, In, and Ga. The semiconductor materials are of various types, including one or more of ZnS, ZnSe, and CdS; one or more of InP and GaP; and one or more of CuInS and CuGaS. The doping amount of the dopant element in the second doped metal oxide particle is 0.1 wt% to 20 wt%, for example, it can be 1 wt%, 2 wt%, 3 wt%, 4 wt%, 5 wt%, 6 wt%, 7 wt%, 8 wt%, 9 wt%, 10 wt%, 11 wt%, 12 wt%, 13 wt%, 14 wt%, 15 wt%, 16 wt%, 17 wt%, 18 wt%, 19 wt%, or any range between two values.

[0128] Fifthly, embodiments of this application also provide a display device, the display device including the above-described optoelectronic device 100.

[0129] The display device can be any electronic product with display function, including but not limited to smartphones, tablets, laptops, digital cameras, digital camcorders, smart wearable devices, smart weighing scales, in-vehicle displays, televisions, or e-book readers. Among them, smart wearable devices can be, for example, smart bracelets, smartwatches, virtual reality (VR) headsets, etc.

[0130] The present application will be specifically described below through specific embodiments. The following embodiments are only some embodiments of the present application and are not intended to limit the present application.

[0131] Example 1

[0132] This embodiment provides an organic compound and a thin film thereof. The method for preparing the organic compound is as follows:

[0133] 10 g (21.1 mmol) of 4,4'-bis(9-carbazole)biphenyl (CBP), 40 mL (0.547 mol) of amide compound DMF, and 150 mL of solvent chlorobenzene were weighed and placed in a flask. Then, under a nitrogen atmosphere, 47 mL (0.562 mol) of catalyst POCl3 was added dropwise to the flask at room temperature. The reaction was carried out at 95 °C for 10 h. The mixture was then poured into a beaker containing crushed ice, neutralized with K2CO3, and the aqueous layer was extracted three times with 100 mL of dichloromethane. The organic layer was then dried with sodium sulfate. Finally, the mixture was purified on a silica gel column (dichloromethane:ethyl acetate = 95:5) to obtain the first intermediate product. The structural formula of the first intermediate product is shown below.

[0134]

[0135] The first intermediate (5 g, 9.3 mmol) was mixed with 200 mL of tetrahydrofuran solvent, 100 mL of ethanol (hydroxyl protecting agent), and 12 mmol of NaBH4 reducing agent. The mixture was reacted at 27 °C for 24 h. Water was then slowly added, and after the solvent evaporated, 0.1 mol of NaOH and dichloromethane were added. The mixture was stirred and filtered under vacuum to obtain the second intermediate. The structural formula of the second intermediate is shown below:

[0136]

[0137] Under a nitrogen atmosphere and at room temperature, the catalyst NaH (0.25 g, 5.4 mmol) was added to a DMF (30 mL) dispersion of the second intermediate (1.0 g, 1.8 mmol), and the reaction mixture was stirred for 3 h, then cooled to 0 °C; then 5.4 mmol of the modifier 4-chloromethylstyrene was added dropwise. The reaction was carried out at 60℃ for 24 hours, then cooled with water, the aqueous layer was extracted with dichloromethane, the organic layer was dried with sodium sulfate, and finally purified by silica gel column chromatography (dichloromethane:polyethylene = 7:3) to obtain the organic compound. The structural formula of the organic compound is shown below:

[0138]

[0139] The method for preparing the thin film includes: dissolving the above-mentioned organic compound in dichloromethane solvent to obtain an organic compound dispersion of 10 mg / mL, spin-coating the organic compound dispersion at a spin speed of 3000 rpm, and then heating at 155°C for 30 min to obtain a thin film with a thickness of 30 nm.

[0140] Example 2

[0141] This embodiment is basically the same as Embodiment 1, except that the modifier 4-chloromethylstyrene is replaced with: The structural formula of the obtained organic compound is:

[0142] Example 3

[0143] This embodiment is basically the same as Embodiment 1, except that the modifier 4-chloromethylstyrene is replaced with: The structural formula of the obtained organic compound is:

[0144] Example 4

[0145] This embodiment is basically the same as Embodiment 1, except that the modifier 4-chloromethylstyrene is replaced with: The structural formula of the obtained organic compound is:

[0146] Example 5

[0147] This embodiment is basically the same as Embodiment 1, except that the reaction temperature of the modifier and the second intermediate product in this embodiment is 70°C.

[0148] Example 6

[0149] This embodiment is basically the same as Embodiment 1, except that the reaction temperature of the modifier and the second intermediate product in this embodiment is 50°C.

[0150] Example 7

[0151] This embodiment is basically the same as Embodiment 1, except that the reaction time of the modifier and the second intermediate product in this embodiment is 28 hours.

[0152] Example 8

[0153] This embodiment is basically the same as Embodiment 1, except that the reaction time of the modifier and the second intermediate product in this embodiment is 20 hours.

[0154] Example 9

[0155] This embodiment is basically the same as Embodiment 1, except that the heating temperature during film preparation in this embodiment is 145°C.

[0156] Example 10

[0157] This embodiment is basically the same as Embodiment 1, except that the heating temperature during film preparation in this embodiment is 130°C.

[0158] Comparative Example 1

[0159] This comparative example is basically the same as Example 1, except that the organic compound is replaced with 4,4'-bis(9-carbazole)biphenyl CBP; the annealing temperature of the film is 210°C.

[0160] Comparative Example 2

[0161] This comparative example is basically the same as Example 1, except that the organic compound in this comparative example is replaced with:

[0162]

[0163] The annealing temperature of the film is 210℃.

[0164] Comparative Example 3

[0165] This comparative example is basically the same as Example 1, except that the organic compound in this comparative example is replaced with:

[0166]

[0167] The annealing temperature of the film is 210℃.

[0168] The 1H and 1C NMR spectra of the organic compound from Example 1 were tested, and the results are as follows:

[0169] 1H NMR (400MHz, CDCl3): δ=8.22-8.11(m,4H),7.93(d,4H),7.71(d,4H),7.59-7. 29(m,18H),6.74(dd,2H),5.76(d,2H),5.25(d,2H),4.77(s,4H),4.62(s,4H).

[0170] 13C NMR (400MHz, CDCl3): δ=141.14,140.52,139.29,138.09,137.25,136.99,136.59,129.98,128.52,128.08,127.42,127 .17,126.49,126.40,126.27,126.09,123.54,123.42,120.45,120.24,120.16,113.75,109.89,109.79,72.62,71.56.

[0171] The crosslinking temperatures of the organic compounds in Examples 1-10 and Comparative Examples 1-3 were tested, and the hole mobility, surface roughness, and flexural strength of the films were measured. The results are shown in Table 1.

[0172] The crosslinking temperature was measured by differential scanning calorimetry (DSC), a commonly used thermal analysis technique that can be used to measure the thermal properties of materials, including glass transition temperature, melting temperature, and crosslinking temperature. The temperature of the crosslinking reaction can be determined by monitoring the heat change of organic compounds during the heating process.

[0173] The hole mobility test method is as follows: The current density-voltage curve of the optoelectronic device (single carrier transport thin-film device, HOD) is measured. The HOD structure is anode / hole transport layer / quantum dot light-emitting layer / cathode, and the hole transport layer material is the organic compound used in Examples 1-8 and Comparative Examples 1-3, respectively. The space charge confinement current (SCLC) region in the current density-voltage curve is obtained, and then the value is calculated according to the formula J = (9 / 8)ε. r ε0μ e V 2 / d 3 Calculate hole mobility; where J represents current density in mA / cm². -2 ;ε r ε₀ represents the relative permittivity, and μ represents the vacuum permittivity. e This represents hole mobility, expressed in cm. 2 V -1 s -1 V represents the driving voltage, with units of V; d represents the film thickness, with units of m.

[0174] Surface roughness was measured using atomic force microscopy (AFM).

[0175] Table 1

[0176]

[0177]

[0178] As shown in Table 1:

[0179] As shown in Examples 1-4 and Comparative Example 1, the thermal crosslinking temperature of the organic compound obtained after CBP modification is reduced from about 200°C to about 150°C, with the thermal crosslinking temperature of Example 3 being reduced to 142°C. This can be achieved by adjusting the chain length of the flexible modifier. At the same time, the migration rate of the film prepared by the organic compound is also significantly improved. The surface roughness is also significantly reduced compared with CBP, indicating that the film prepared by the modified CBP has better density.

[0180] As can be seen from Examples 1, 5-10 and Comparative Examples 1-3, modifying CBP at the suitable reaction and crosslinking temperatures provided in this application can reduce the crosslinking temperature of organic compounds, increase the hole mobility of films prepared from organic compounds, and reduce the surface roughness of films. In Comparative Examples 2-3, methyl groups or O=S=O bonds exist on the benzene ring host. Methyl groups can cause changes in the electron cloud of carbons on adjacent benzene rings, reducing the conjugation effect of the benzene ring. This leads to a weakening of the conjugation effect between the benzene ring and the alkenyl group, and the flexibility of the structure will be greatly reduced. Furthermore, the methyl group on biphenyl is an electron-donating group, which may generate free radicals and undergo reactions such as electrophilic substitution and oxidation reactions under high temperature conditions. These reactions may damage the film or generate a large number of defects during film formation. The electronegativity of O=S=O bonds is stronger than that of carbons on the benzene ring, which can also cause electron cloud rearrangement and weaken the conjugation effect of the host. Therefore, the performance of the organic compounds in Comparative Examples 2-3 is still inferior to that of the examples.

[0181] Device Example 1

[0182] This embodiment provides an optoelectronic device, the fabrication method of which is as follows:

[0183] The ITO conductive glass was cleaned with a cleaning agent to initially remove the stains on the surface. Then, it was ultrasonically cleaned for 20 minutes each in deionized water, acetone, anhydrous ethanol, and deionized water to remove the impurities on the surface. Finally, it was dried with high-purity nitrogen to form an ITO anode with a thickness of 100 nm.

[0184] PEDOT:PSS was spin-coated onto an ITO anode at 3500 rpm, followed by heating at 150°C for 20 min to form a hole injection layer with a thickness of 25 nm.

[0185] The method for preparing the thin film as described in Example 1 forms a hole transport layer on the hole injection layer;

[0186] CdSe / ZnS quantum dots were dissolved in n-octane solvent and spin-coated onto the hole transport layer at a speed of 3000 rpm for 30 s. The mixture was then heated at 100 °C for 5 min to form a light-emitting layer with a thickness of 15 nm.

[0187] ZnO was dissolved in ethanol and spin-coated onto the light-emitting layer at a speed of 4000 rpm for 30 seconds. Then it was heated at 100°C for 10 minutes to form an electron transport layer with a thickness of 35 nm.

[0188] Ag is deposited on the electron transport layer by thermal evaporation, with a vacuum level not exceeding 3 x 10⁻⁶. -4 Pa, velocity of 0.8 angstroms / second, time of 1000 s, forming a cathode with a thickness of 100 nm;

[0189] Optoelectronic devices are obtained by encapsulating with acrylic resin.

[0190] Device Examples 2-10

[0191] Device Examples 2-10 are basically the same as Device Example 1, except that hole transport layers are formed in Device Examples 2-10 using the same method as in Examples 2-10 for preparing thin films.

[0192] Device Comparison Examples 1-3

[0193] The devices in Comparative Examples 1 to 3 are basically the same as those in Device Example 1, except that the hole transport layer is formed in Comparative Examples 1 to 3 by the same method used to prepare the thin film as in Comparative Examples 1 to 3.

[0194] The external quantum efficiency (EQE) and lifetime (T95@1000nit) of the optoelectronic devices in Device Examples 1-10 and Device Comparative Examples 1-3 were tested respectively, and the results are shown in Table 2.

[0195] The start-up voltage was measured using an efficiency testing system built with Keithley 6485.

[0196] External quantum efficiency (EQE) is measured as the ratio of electron-hole pairs injected into a quantum dot to the number of emitted photons, expressed as a percentage (%). It is an important parameter for evaluating the quality of electroluminescent devices and can be obtained using an EQE optical testing instrument. The specific calculation formula is as follows:

[0197]

[0198] Where, η e For optical output coupling efficiency, η r χ is the ratio of recombination carriers to injected carriers, and K is the ratio of excitons producing photons to the total number of excitons. R K is the radiation process rate. NR This represents the rate of a non-radiative process.

[0199] Test conditions: Conducted at room temperature with an air humidity of 30-60%.

[0200] The measurement method for lifetime T95@1000nit is as follows: Under constant current or voltage drive, the time required for the brightness of the device to decrease to a certain percentage of its maximum brightness is defined as T95. This lifetime is the measured lifetime. To shorten the testing cycle, device lifetime testing is usually performed at high brightness by accelerating device aging, and the lifetime at high brightness is obtained by fitting an extended exponential decay brightness decay fitting formula. For example, the lifetime at 1000nit is measured as T95@1000nit. The specific calculation formula is as follows:

[0201]

[0202] Among them, T95 L For longer lifespan at low brightness, T95 H For the measured lifetime under high brightness, L H To accelerate the device to its maximum brightness, L L The value is 1000 nits, and A is the acceleration factor. In this experiment, the lifetime of several groups of QLED devices under rated brightness was measured, and the value of A was found to be 1.7.

[0203] Table 2

[0204]

[0205]

[0206] As shown in Table 2:

[0207] As can be seen from Device Examples 1-4 and Device Comparative Example 1, when the organic compound provided in this application is used as the material for the hole transport layer to prepare the optoelectronic device, due to the significant improvement in the quality of the hole transport layer, the holes and electrons of the optoelectronic device are more balanced, its external quantum efficiency is significantly improved, and the lifetime of the optoelectronic device is also significantly extended.

[0208] As can be seen from device examples 1, 5-10 and device comparative examples 1-3, within the CBP modification conditions provided in this application, the prepared organic compounds all have lower crosslinking temperatures and higher hole mobility. Furthermore, the hole transport layer prepared by the organic compounds has better film-forming performance and higher density, which further promotes hole transport, thereby improving the external quantum efficiency of optoelectronic devices and extending the service life of optoelectronic devices.

[0209] The technical solutions provided by the embodiments of this application have been described in detail above. Specific examples have been used to illustrate the principles and implementation methods of this application. The description of the above embodiments is only for the purpose of helping to understand the method and core ideas of this application. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of this application. Therefore, the content of this specification should not be construed as a limitation of this application.

Claims

1. An organic compound, characterized in that, The structural formula of the organic compound is shown below: Among them, L1 and L2 are each independently selected from single-bonded, substituted, or unsubstituted C1 to C2 bonds. 40 Alkylene, substituted or unsubstituted C2-C 20 Etheryl group, substituted or unsubstituted arylene group, substituted or unsubstituted aryleneoxy group, substituted or unsubstituted arylene thio group, substituted or unsubstituted -(CH2) n1 CO(CH2) n2 -, substituted or unsubstituted -(CH2) n3 NHCO(CH2) n4 -, substituted or unsubstituted -(CH2) n5 CONH(CH2) n6 -, substituted or unsubstituted -(CH2) n7 COO(CH2) n8 -, substituted or unsubstituted -(CH2) n9 One or more combinations of C(NH)-; wherein n1 to n9 are each independently selected from integers from 1 to 20; R1, R2, R3, and R4 are each independently selected from H, D, halogen, cyano, hydroxyl, carboxyl, aldehyde, nitro, unsubstituted or substituted with -D, -NH2, -F, -Cl, -Br, -I, -OH, -COOH, -NO2, -SO3H, -CHO, -SH, or -CN, belonging to the C1-C group. 10 alkyl.

2. The organic compound according to claim 1, characterized in that, The crosslinking temperature of the organic compound is 130℃~155℃; and / or The HOMO energy level of the organic compound is -6.35 eV to -6.20 eV; and / or The LUMO energy level of the organic compound is -2.97 eV to -2.90 eV; and / or R1, R2, R3, and R4 may be the same or different; and / or L1 and L2 may be the same or different.

3. The organic compound according to claim 1, characterized in that, It also includes at least one of the following features (1) to (4): (1) L1 and L2 are each independently selected from single-bonded, substituted, or unsubstituted C1 to C2 bonds. 20 Alkylene, substituted or unsubstituted C2-C 10 Etheryl group, substituted or unsubstituted arylene group, substituted or unsubstituted aryleneoxy group, substituted or unsubstituted arylene thio group, substituted or unsubstituted -(CH2) n1 CO(CH2) n2 -, substituted or unsubstituted -(CH2) n3 NHCO(CH2) n4 -, substituted or unsubstituted -(CH2) n5 CONH(CH2) n6 -, substituted or unsubstituted -(CH2) n7 COO(CH2) n8 -, substituted or unsubstituted -(CH2) n9 One or more combinations of C(NH)-; wherein n1 to n9 are each independently selected from integers from 1 to 10; (2) L1 and L2 are each independently selected from single-bonded, substituted, or unsubstituted C1 to C2 bonds. 10 Alkylene, substituted or unsubstituted C2–C8 etherene, substituted or unsubstituted arylene, substituted or unsubstituted aryleneoxy, substituted or unsubstituted arylenethio, substituted or unsubstituted -(CH2) n1 CO(CH2) n2 -, substituted or unsubstituted -(CH2) n3 NHCO(CH2) n4 -, substituted or unsubstituted -(CH2) n5 CONH(CH2) n6 -, substituted or unsubstituted -(CH2) n7 COO(CH2) n8 -, substituted or unsubstituted -(CH2) n9 One or more combinations of C(NH)-; wherein n1 to n9 are each independently selected from integers from 1 to 8; (3) L1 and L2 are each independently selected from substituted or unsubstituted C1 to C5 alkylene groups; (4) L1 and L2 are the same.

4. The organic compound according to claim 1, characterized in that, It also includes at least one of the following features (1) to (3): (1) R1, R2, R3, and R4 are each independently selected from H, D, halogen, cyano, hydroxyl, carboxyl, aldehyde, nitro, unsubstituted or substituted by -D, -NH2, -F, -Cl, -Br, -I, -OH, -COOH, -NO2, -SO3H, -CHO, -SH, and -CN C1-C8 alkyl groups; (2) R1, R2, R3, and R4 are each independently selected from H, D, halogen, cyano, hydroxyl, carboxyl, aldehyde, and nitro groups; (3) R1 and R3 are the same, and R2 and R4 are the same.

5. The organic compound according to claim 1, characterized in that, The organic compound is selected from compounds having the following structural formula:

6. A thin film, characterized in that, The material of the film includes the organic compounds as described in any one of claims 1 to 5.

7. The thin film as claimed in claim 6, characterized in that, The thickness of the thin film is 10 nm to 40 nm; and / or The surface roughness of the film is 2.2 nm to 5.1 nm.

8. A method for preparing a thin film, characterized in that, Includes the following steps: Provide an organic compound as described in any one of claims 1 to 5; The organic compound is deposited and heated to obtain a thin film.

9. The preparation method according to claim 8, characterized in that, Depositing the organic compound includes: providing an organic compound dispersion comprising the organic compound, and depositing the organic compound dispersion; Optionally, the organic compound dispersion contains an organic compound with a mass concentration of 10 mg / mL to 60 mg / mL. Optionally, the organic compound dispersion further includes a solvent, which includes one or more of the following: n-octane, isooctane, n-hexane, cyclohexane, ethyl acetate, benzene, toluene, chloroform, carbon tetrachloride, dichloromethane, dimethyl ether, and tetraethylene glycol dimethyl ether.

10. The preparation method according to claim 8, characterized in that, The heating temperature is 130℃~155℃; and / or The heating time is 30 to 40 minutes.

11. An optoelectronic device, characterized in that, It includes an anode, a hole-functional layer, an active layer, and a cathode stacked sequentially; wherein the hole-functional layer includes the thin film as described in any one of claims 6 to 7, or includes the thin film prepared by the preparation method as described in any one of claims 8 to 10.

12. The optoelectronic device as described in claim 11, characterized in that, The hole functional layer includes one or more of a hole injection layer and a hole transport layer, wherein the hole injection layer is located between the anode and the hole transport layer; and the hole transport layer includes the thin film.

13. The optoelectronic device as described in claim 12, characterized in that, The hole injection layer is made of organic or inorganic P-type semiconductor materials. The organic P-type semiconductor materials include 4,4'-N,N'-dicarbazolyl-biphenyl, N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4'-diamine, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-spiro, and N,N'-bis(4-(N,N) '-Diphenyl-amino)phenyl)-N,N'-diphenylbenzidine, 4,4',4'-tris(N-carbazolyl)-triphenylamine, 4,4',4'-tris(carbazol-9-yl)triphenylamine, trichloroisocyanuric acid, terbium-doped phosphate-based green luminescent materials, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzphenanthrene, 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, poly[(9,9'-dioctylfluorene-2,7-diyl)-co-(4,4'-(N -(4-sec-butylphenyl)diphenylamine), poly(4-butylphenyl-diphenylamine), poly[bis(4-phenyl)(4-butylphenyl)amine], polyaniline, polypyrrole, poly(p-)phenylenevinylene, poly(phenylenevinylene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene], poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene], copper phthalocyanine, aromatic tertiary amines, polynuclear aromatic tertiary amines, 4,4'-bis(p-carbazole)-1,1' -Biphenyl compounds, N,N,N',N'-tetraarylbenzidine, PEDOT, PEDOT:PSS and its derivatives, PEDOT:PSS derivatives doped with s-MoO3, poly(N-vinylcarbazole) and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, poly(spirofluorene) and its derivatives, N,N'-di(naphthyl-1-yl)-N,N'-diphenylbenzidine, spironolactone (NPB), nanocrystalline diamond, microcrystalline cellulose and tetracyanoquinone dimethane, doped graphene, undoped graphene;The inorganic P-type semiconductor material comprises one or more of the following: first doped metal oxide particles, first undoped metal oxide particles, metal sulfide, metal selenide, and metal nitride. The metal oxides in the first doped metal oxide particles and the first undoped metal oxide particles each independently comprise one or more of MoO3, WO3, NiO, CrO3, CuO, and V2O5. The doping element in the first doped metal oxide particles comprises one or more of Mo, W, Ni, Cr, Cu, and V. The metal sulfide comprises one or more of CuS, MoS3, and WS3. The metal selenide comprises one or more of MoSe3 and WSe3. The metal nitride comprises P-type gallium nitride. The doping amount of the doping element in the first doped metal oxide particles is 0.1 wt% to 20 wt%. The anode and the cathode each independently comprise one or more of a metal, a carbon material, and a metal oxide; the metal comprises one or more of Al, Ag, Cu, Mo, Au, Ba, Ca, Yb, and Mg; the carbon material comprises one or more of graphite, carbon nanotubes, graphene, and carbon fibers; the metal oxide comprises a metal oxide electrode or a composite electrode in which a metal is disposed between doped or undoped transparent metal oxides; the material of the metal oxide electrode comprises one or more of ITO, FTO, ATO, AZO, GZO, IZO, MZO, MoO3, and AMO; the composite electrode comprises one or more of AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, ZnS / Ag / ZnS, ZnS / Al / ZnS, TiO2 / Ag / TiO2, and TiO2 / Al / TiO2; and / or The active layer includes a light-emitting layer, the material of which includes one or more organic light-emitting materials and quantum dot light-emitting materials; the organic light-emitting material is selected from 4,4'-bis(N-carbazole)-1,1'-biphenyl:tris[2-(p-tolyl)pyridinium(III)], 4,4',4”-tris(carbazole-9-yl)triphenylamine:tris[2-(p-tolyl)pyridinium], diaromatic anthracene derivatives, stilbene aromatic derivatives, pyrene derivatives, fluorene derivatives, TBPe fluorescent materials, TTPX fluorescent materials, TBRb fluorescent materials, DBP fluorescent materials, delayed fluorescence materials, etc. The quantum dot luminescent material is selected from one or more of the following: fluorescent materials, TTA materials, TADF materials, polymers containing BN covalent bonds, HLCT materials, and Exciplex luminescent materials; the quantum dot luminescent material is selected from one or more of the following: single-structure quantum dots, core-shell structure quantum dots, and perovskite quantum dots; the material of the single-structure quantum dot, the core material of the core-shell structure quantum dot, and the shell material of the core-shell structure quantum dot are respectively selected from one or more of the following: group II-VI compounds, group IV-VI compounds, group III-V compounds, and group I-III-VI compounds; the core-shell structure quantum dot... The shell comprises one or more layers; the II-VI group compounds are selected from CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnS eTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and HgZnSTe; wherein the IV-VI compound is selected from one or more of SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, and SnPbSTe;The III-V compounds are selected from one or more of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and InAlPSb. Multiple types; the I-III-VI group compounds are selected from one or more of CuInS2, CuInSe2, and AgInS2; the core-shell structured quantum dots are selected from one or more of CdSe / CdSeS / CdS, InP / ZnSeS / ZnS, CdZnSe / ZnSe / ZnS, CdSeS / ZnSeS / ZnS, CdSe / ZnS, CdSe / ZnSe / ZnS, ZnSe / ZnS, ZnSeTe / ZnS, CdSe / CdZnSeS / ZnS, and InP / ZnSe / ZnS; the perovskite quantum dots are made of doped or undoped inorganic perovskite semiconductors or organic-inorganic hybrid perovskite semiconductors; the inorganic perovskite semiconductor has the general structural formula AMX3, where A is Cs; + Ion, M is a divalent metal cation selected from Pb 2 + Sn 2+ Cu 2+ Ni 2+ Cd 2+ Cr 2+ Mn 2+ Co 2+ Fe 2+ 、Ge 2+ Yb 2+ Eu 2+ One or more of the following, where X is a halide anion selected from Cl... - ,Br - I - One or more of the following; the general structural formula of the organic-inorganic hybrid perovskite semiconductor is BMX3, where B is an organic amine cation selected from CH3(CH2). n-2 NH3 + Or [NH3(CH2)] n NH3] 2+ Where n≥2, M is a divalent metal cation selected from Pb 2+ Sn 2+ Cu 2+ Ni 2+ Cd 2+ Cr 2+ Mn 2+ Co 2+ Fe 2+ 、Ge 2+ Yb 2+ Eu 2+ One or more of the following, where X is a halide anion selected from Cl... - ,Br - I - One or more of the following; and / or The optoelectronic device further includes an electronic functional layer located between the active layer and the cathode; the material of the electronic functional layer includes one or more of the following: second doped metal oxide particles, second undoped metal oxide particles, IIB-VIA group semiconductor materials, IIIA-VA group semiconductor materials, and IB-IIIA-VIA group semiconductor materials; the material of the second undoped metal oxide particles includes one or more of ZnO, TiO2, SnO2, ZrO2, and Ta2O5; the metal oxide in the second doped metal oxide particles includes ZnO, TiO2, SnO2, ZrO2, Ta2O5, and Al. The second doped metal oxide particle contains one or more of Al, Mg, Li, Mn, Y, La, Cu, Ni, Zr, Ce, In, and Ga; the IIB-VIA group semiconductor material contains one or more of ZnS, ZnSe, and CdS; the IIIA-VA group semiconductor material contains one or more of InP and GaP; and the IB-IIIA-VIA group semiconductor material contains one or more of CuInS and CuGaS. The doping amount of the second doped metal oxide particle is 0.1 wt% to 20 wt%.

14. A display device, characterized in that, Including the optoelectronic device as described in any one of claims 11 to 13.

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