Organic compound, thin film preparation method, thin film, photoelectric device and electronic equipment

Abstract

The invention provides an organic compound, a thin film preparation method, a thin film, a photoelectric device and electronic equipment, an organic compound shown in a general formula (I) is subjected to spin coating and heat treatment, and then the thin film comprising the organic compound shown in a general formula (II) and the photoelectric device comprising the thin film are obtained. The organic compound shown in the general formula (II) is free of a long alkyl side chain, so that the conductivity of the device can be improved, and the technical problem of poor conductivity of a photoelectric device in the prior art is solved.

Description

Technical Field

[0001] The present application relates to the technical field of optoelectronic devices, and in particular to organic compounds, thin film preparation methods, thin films, optoelectronic devices and electronic devices. Background Art

[0002] Photoelectric devices refer to a class of devices made using the photoelectric effect of semiconductors, including but not limited to light-emitting devices, solar cells or photodetectors. Taking light-emitting devices as an example, light-emitting devices include but are not limited to organic light-emitting diodes 10 (Organic Light-Emitting Diode, OLED) and quantum dot light-emitting diodes (Quantum Dot Light-Emitting Diodes, QLED). OLED / QLED generally includes an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode arranged in sequence. Among them, the anode and the cathode are arranged opposite to each other, and the light-emitting layer is arranged between the anode and the cathode. The light-emitting principle of OLED / QLED is: electrons are injected from the cathode of the device into the light-emitting area, and holes are injected from the anode of the device into the light-emitting area. The electrons and holes recombine in the light-emitting area to form excitons, and the recombined excitons release photons in the form of radiative transitions, thereby emitting light.

[0003] After years of development, optoelectronic devices have made great progress in performance indicators and have shown great potential for application development. However, there are still shortcomings, and it is necessary to improve the conductive performance of optoelectronic devices. Summary of the Invention

[0004] The embodiments of the present application provide organic compounds, thin film preparation methods, thin films, optoelectronic devices, and electronic devices.

[0005] In a first aspect, the embodiments of the present application provide an organic compound having a structure as shown in the general formula (I):

[0006]

[0007] in:

[0008] R1 is selected from a straight or branched chain alkyl group containing 1 to 24 carbon atoms;

[0009] AR1 is selected from one or more of a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms;

[0010] AR2 is selected from: a substituted or unsubstituted aromatic amine group containing 6 to 60 ring atoms;

[0011] n is: 20-85.

[0012] In a second aspect, an embodiment of the present application provides a thin film, wherein the material of the thin film includes at least one organic compound having a structure such as the general formula (II):

[0013]

[0014] The organic compound represented by the general formula (II) is obtained by heat-treating the organic compound represented by the general formula (I);

[0015] in:

[0016] AR1 is selected from one or more of a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms;

[0017] AR2 is selected from: a substituted or unsubstituted aromatic amine group containing 6 to 60 ring atoms;

[0018] n is: 20-85.

[0019] In a third aspect, an embodiment of the present application provides a method for preparing a thin film, wherein the method comprises the following steps:

[0020] depositing a first functional fluid; and

[0021] heat-treating the deposited first functional liquid to obtain a thin film;

[0022] The first functional liquid includes an organic compound having a structure as shown in general formula (I):

[0023]

[0024] wherein R1 is selected from a straight or branched chain alkyl group containing 1 to 24 carbon atoms;

[0025] AR1 is selected from one or more of a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms;

[0026] AR2 is selected from substituted or unsubstituted aromatic amine groups containing 6 to 60 ring atoms;

[0027] n is: 20-85.

[0028] In a fourth aspect, an embodiment of the present application provides an optoelectronic device, comprising:

[0029] an anode and a cathode arranged opposite to each other;

[0030] a light-emitting layer disposed between the anode and the cathode; and

[0031] a hole functional layer, disposed between the anode and the light-emitting layer;

[0032] Wherein, the hole functional layer includes the above-mentioned thin film, or a thin film prepared by the above-mentioned thin film preparation method.

[0033] In a fifth aspect, an embodiment of the present application provides an electronic device, comprising a thin film produced by the above-mentioned thin film preparation method, or a photoelectric device as described above.

[0034] Beneficial effects of the embodiments of the present application:

[0035] The present application provides an organic compound having good hole mobility, making it more suitable for use as a hole functional layer material compared to other existing hole functional layer materials. Furthermore, the organic compound's longer side chains give it better solubility and processability, making it easier to use.

[0036] The present application provides a thin film, comprising an organic compound represented by general formula (II) obtained by spin coating and heat treating an organic compound represented by general formula (I). Since the organic compound represented by general formula (II) removes a longer side chain, the steric hindrance between the organic compounds is reduced, so that the organic compound represented by general formula (II) has a higher hole mobility, thereby improving the conductive properties of the film.

[0037] The present application provides a photoelectric device, which is obtained by spin coating and heat treating an organic compound represented by general formula (I) to obtain a thin film including an organic compound represented by general formula (II), and a photoelectric device including the above-mentioned thin film. Since the organic compound represented by general formula (II) has removed a longer side chain, the conductive performance of the device can be improved, thereby improving the technical problem of poor conductive performance of photoelectric devices in the prior art. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for use in the description of the embodiments. Obviously, the drawings described below are only some embodiments of the present application. For those skilled in the art, other drawings can be obtained based on these drawings without creative work.

[0039] Figure 1 It is a schematic structural diagram of the optoelectronic device provided in device embodiments 1-7 of the present application.

[0040] 1. Anode; 2. Cathode; 3. Electron injection layer; 4. Electron transport layer; 5. Hole transport layer; 6. Light-emitting layer. DETAILED DESCRIPTION

[0041] The following will be combined with the drawings in the embodiments of the present application to clearly and completely describe the technical solutions in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without making creative work are within the scope of protection of this application. In addition, it should be understood that the specific embodiments described herein are only used to illustrate and explain the present application and are not used to limit the present application.

[0042] In this application, unless otherwise indicated, directional terms such as "upper" and "lower" generally refer to the upper and lower positions of a device in actual use or operation, specifically in the drawing directions of the accompanying drawings; whereas "inner" and "outer" refer to the outline of the device. Furthermore, in the description of this application, the term "including" means "including but not limited to." Terms such as first, second, and third are used merely as labels and do not impose numerical requirements or establish a sequence.

[0043] In this application, "and / or" describes the association relationship between associated objects, indicating that three relationships can exist. For example, A and / or B can mean: A exists alone, A and B exist at the same time, and B exists alone. A and B can be singular or plural.

[0044] In this application, "at least one" means one or more, and "plurality" means two or more. "At least one", "at least one of the following" or similar expressions refer to any combination of these items, including any combination of single items or plural items. For example, "at least one of a, b, or c", or "at least one of a, b, and c" can all mean: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, and c can be single or multiple.

[0045] In the present application, when another layer is formed "on" a certain layer, the so-called "on" is a broad concept, which may indicate that the formed another layer is adjacent to a certain layer, or it may indicate that there are other spacing structural layers between the formed another layer and the certain layer. For example, when a second electrode is formed "on" the first carrier functional layer, the so-called "on" may indicate that the formed second electrode is adjacent to the first carrier functional layer, or it may indicate that there are other spacing structural layers between the second electrode and the first carrier functional layer, such as a light-emitting layer.

[0046] Various embodiments of the present application may be presented in the form of a range; it should be understood that the description in the form of a range is only for convenience and brevity and should not be understood as a hard limitation on the scope of the present application; therefore, the range description should be considered to have specifically disclosed all possible sub-ranges and single numbers within the range. For example, the description of a range from 1 to 6 should be considered to have 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., as well as single numbers within the range, such as 1, 2, 3, 4, 5 and 6, which applies regardless of the range. In addition, whenever a numerical range is indicated herein, it is meant to include any cited number (fractional or integer) within the indicated range.

[0047] The technical solution of this application is as follows:

[0048] In a first aspect, the present invention provides an organic compound having a structure as shown in general formula (I):

[0049]

[0050] in:

[0051] R1 is selected from a straight or branched chain alkyl group containing 1 to 24 carbon atoms;

[0052] AR1 is selected from one or more of a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms;

[0053] AR2 is selected from: a substituted or unsubstituted aromatic amine group containing 6 to 60 ring atoms;

[0054] n is: 20-85.

[0055] It should be noted that an aromatic amine group refers to an amine with an aromatic substituent, i.e., -NH2, -NH or a nitrogen-containing group connected to an aromatic hydrocarbon. The structure of the aromatic hydrocarbon usually contains one or more benzene rings, i.e., the nitrogen atom is directly connected to the carbon atom of the benzene ring by a chemical bond.

[0056] In some embodiments, R1 is selected from a linear or branched alkyl group containing 10-16 carbon atoms; and / or

[0057] AR1 is selected from one of substituted or unsubstituted fluorenyl, spirobifluorenyl, carbazole, thiophene, bithiophene, fused ring thiophene, benzofuran and pyrrole; and / or

[0058] AR2 is selected from one of substituted or unsubstituted triphenylamine, methoxytriphenylamine and diphenylamine.

[0059] In some embodiments, AR1 is selected from substituted or unsubstituted fluorenyl or pyrrole; and / or

[0060] AR2 is selected from substituted or unsubstituted triphenylamine.

[0061] In some embodiments, the organic compound has a structure represented by any of the following structural formulas:

[0062]

[0063]

[0064]

[0065]

[0066] In a second aspect, an embodiment of the present application provides a thin film, wherein the material of the thin film includes at least one organic compound having a structure such as the general formula (II):

[0067]

[0068] The organic compound represented by the general formula (II) is obtained by heat-treating the organic compound represented by the general formula (I);

[0069] in:

[0070] AR1 is selected from one or more of a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms;

[0071] AR2 is selected from: a substituted or unsubstituted aromatic amine group containing 6 to 60 ring atoms;

[0072] n is: 20-85.

[0073] It should be noted that an aromatic amine group refers to an amine with an aromatic substituent, i.e., -NH2, -NH or a nitrogen-containing group connected to an aromatic hydrocarbon. The structure of the aromatic hydrocarbon usually contains one or more benzene rings, i.e., the nitrogen atom is directly connected to the carbon atom of the benzene ring by a chemical bond.

[0074] In some embodiments, AR1 is selected from one of substituted or unsubstituted fluorenyl, spirobifluorenyl, carbazole, thiophene, bithiophene, fused ring thiophene, benzofuran and pyrrole; and / or

[0075] AR2 is selected from one of substituted or unsubstituted triphenylamine, methoxytriphenylamine and diphenylamine.

[0076] In some embodiments, AR1 is selected from substituted or unsubstituted fluorenyl or pyrrole; and / or

[0077] AR2 is selected from substituted or unsubstituted triphenylamine.

[0078] In some embodiments, the material of the thin film includes one or more of the following organic compounds:

[0079]

[0080]

[0081] In a third aspect, an embodiment of the present application provides a method for preparing a thin film, wherein the method comprises the following steps:

[0082] In some embodiments, depositing a first functional fluid; and

[0083] heat-treating the deposited first functional liquid to obtain a thin film;

[0084] The first functional liquid includes an organic compound having a structure as shown in general formula (I):

[0085]

[0086] wherein R1 is selected from a straight or branched chain alkyl group containing 1 to 24 carbon atoms;

[0087] AR1 is selected from one or more of a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms;

[0088] AR2 is selected from substituted or unsubstituted aromatic amine groups containing 6 to 60 ring atoms;

[0089] n is: 20-85.

[0090] It should be noted that an aromatic amine group refers to an amine with an aromatic substituent, i.e., -NH2, -NH or a nitrogen-containing group connected to an aromatic hydrocarbon. The structure of the aromatic hydrocarbon usually contains one or more benzene rings, i.e., the nitrogen atom is directly connected to the carbon atom of the benzene ring by a chemical bond.

[0091] In some embodiments, R1 is selected from a linear or branched alkyl group containing 10-16 carbon atoms; and / or

[0092] AR1 is selected from the group consisting of substituted or unsubstituted fluorenyl, spirobifluorenyl, carbazole, thiophene, bithiophene, fused ring thiophene, benzofuran and pyrrole; and / or

[0093] AR2 is selected from the group consisting of substituted or unsubstituted triphenylamine, methoxytriphenylamine and diphenylamine.

[0094] In some embodiments, R1 is selected from one of the following structures:

[0095]

[0096] and / or

[0097] AR1 is selected from substituted or unsubstituted: fluorenyl or pyrrole; and / or

[0098] AR2 is selected from substituted or unsubstituted: triphenylamine;

[0099] * indicates the attachment site.

[0100] In some embodiments, the heat treatment temperature is 150-300° C., and the heat treatment time is 30-60 min.

[0101] In a fourth aspect, an embodiment of the present application provides a method for preparing a photoelectric device, applying the above-mentioned thin film preparation method, comprising the following steps:

[0102] Depositing hole injection layer material on the anode to prepare a hole injection layer;

[0103] Depositing a first functional liquid on the hole injection layer, and heat-treating the deposited first functional liquid to obtain a thin film, which is the hole transport layer;

[0104] Depositing the material of the light-emitting layer on the hole transport layer to prepare the light-emitting layer;

[0105] Depositing an electron transport layer material on the light-emitting layer to prepare an electron transport layer;

[0106] Depositing an electron injection layer material on the electron transport layer to prepare an electron injection layer;

[0107] The cathode material is evaporated onto the electron injection layer to prepare the cathode.

[0108] Encapsulation.

[0109] In some embodiments, the method for preparing the optoelectronic device may also be:

[0110] Depositing electron injection layer material on the upper cathode to prepare an electron injection layer;

[0111] Depositing an electron transport layer material on the electron injection layer to prepare an electron transport layer;

[0112] Depositing the material of the light-emitting layer on the electron transport layer to prepare the light-emitting layer;

[0113] Depositing a first functional liquid on the light-emitting layer and heat-treating the deposited first functional liquid to obtain a thin film, which is a hole transport layer;

[0114] Depositing hole injection layer material on the hole transport layer to prepare a hole injection layer;

[0115] The anode material is evaporated onto the hole injection layer to prepare the anode.

[0116] Encapsulation.

[0117] The deposition method can be implemented by technical means well known in the art, including chemical or physical methods. Among them, chemical methods include chemical vapor deposition, continuous ion layer adsorption and reaction, anodic oxidation, electrolytic deposition, and coprecipitation. Physical methods can be selected from physical plating or solution processing. Specifically, physical plating methods include thermal evaporation, electron beam evaporation, magnetron sputtering, multi-arc ion plating, physical vapor deposition, atomic layer deposition, and pulsed laser deposition; solution processing methods include spin coating, printing, inkjet printing, doctor blade coating, printing, dip coating, immersion, spraying, roller coating, casting, slit coating, and strip coating. Specific processing methods and processing conditions can refer to common methods in the art and will not be repeated here.

[0118] In a fifth aspect, an embodiment of the present application provides a photoelectric device, which is manufactured using the above-mentioned method for manufacturing a photoelectric device, and includes: an anode and a cathode arranged opposite to each other;

[0119] a light-emitting layer disposed between the anode and the cathode; and

[0120] a hole functional layer, disposed between the anode and the light-emitting layer;

[0121] Wherein, the hole functional layer includes the above-mentioned film, or a film prepared by the above-mentioned film preparation method.

[0122] In some embodiments, an electronic functional layer is further included, which is disposed between the cathode and the light-emitting layer.

[0123] and / or

[0124] The anode and cathode each independently include a doped metal oxide electrode, a composite electrode, a graphene electrode, a carbon nanotube electrode, a metal element electrode or an alloy electrode. The material of the doped metal oxide electrode includes one or more of indium-doped tin oxide, fluorine-doped tin oxide, antimony-doped tin oxide, aluminum-doped zinc oxide, gallium-doped zinc oxide, indium-doped zinc oxide, magnesium-doped zinc oxide, aluminum-doped magnesium oxide, and cadmium-doped zinc oxide. The composite electrode includes AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, TiO2 / Ag / TiO2, TiO2 / Al / TiO2, ZnS / Ag / ZnS, ZnS / Al / ZnS, Ca / Al, LiF / Ca, LiF / Al, BaF2 / Al, CsF / Al, CaCO3 / Al or BaF2 / Ca / Al, the material of the metal element electrode includes one or more of Ag, Ni, Pt, Au, Ir, Cu, Mo, Al, Ca, Mg and Ba, and the alloy electrode includes an Au:Mg alloy electrode or an Ag:Mg alloy electrode;

[0125] The material of the light-emitting layer includes one or more of an organic light-emitting material and a quantum dot light-emitting material, and the organic light-emitting material includes one or more of 4,4'-bis(N-carbazole)-1,1'-biphenyl:tris[2-(p-tolyl)pyridine iridium(III), 4,4',4"-tris(carbazole-9-yl)triphenylamine:tris[2-(p-tolyl)pyridine iridium, diarylanthracene derivatives, distyrene aromatic derivatives, pyrene derivatives, fluorene derivatives, TBPe fluorescent materials, TTPX fluorescent materials, TBRb fluorescent materials, DBP fluorescent materials, delayed fluorescence materials, TTA materials, thermally activated delay materials, polymers containing covalent bonding of BN, hybrid localized charge transfer excited state materials, exciplex light-emitting materials, polyacetylene and its derivatives, poly-p-phenylene and its derivatives, polythiophene and its derivatives, polyfluorene and its derivatives;The quantum dot luminescent material includes one or more of a single structure quantum dot, a core-shell structure quantum dot and a perovskite semiconductor material. 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 independently selected from one or more of group II-VI compounds, group IV-VI compounds, group III-V compounds and group I-III-VI compounds. The group II-VI compounds include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, Zn One or more of STe, 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 compound includes SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, One or more of PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, and SnPbSTe, and the III-V compounds include 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, GaAlN One or more of As, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs and InAlPSb, the I-III-VI group compound includes one or more of CuInS2, CuInSe2 and AgInS2; the perovskite semiconductor material includes a doped or undoped inorganic perovskite semiconductor or an organic-inorganic hybrid perovskite semiconductor, and the general structural formula of the inorganic perovskite semiconductor is AMX3, wherein A is Cs; + ions, M is a divalent metal cation, including Pb 2+ 、Sn 2+ 、Cu 2+ 、Ni2+ 、Cd 2+ Cr 2+ 、Mn 2+ 、Co 2+ 、Fe 2+ 、Ge 2+ 、Yb 2+ 、Eu 2+ One or more of, X is a halogen anion, including Cl - Br - , I - One or more of the following; the general structural formula of the organic-inorganic hybrid perovskite semiconductor is BMX3, wherein B is an organic amine cation, including CH3(CH2) n-2 NH3 + or [NH3(CH2) n NH3] 2+ , where n≥2, M is a divalent metal cation, including 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, X is a halogen anion, including Cl-, Br - , I - One or more of; and / or

[0126] The materials of the hole functional layer also include 4,4'-N,N'-dicarbazolyl-biphenyl, poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine], 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, poly(N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine), N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-spiro, N,N'-bis(4-(N,N'-diphenyl-amino)phenyl)-N,N'-bis(phenyl)-1,1'-biphenyl-4,4"-diamine. triphenylamine, 4,4',4'-tris(N-carbazolyl)-triphenylamine, 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(N-vinylcarbazole) and its derivatives, N,N'-di(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4-4'-diamine, spiro NPB, poly(phenylene vinylene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene], poly [2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylene vinylene], 2,2',7,7'-tetrakis[N,N-bis(4-methoxyphenyl)amino]-9,9'-spirobifluorene, 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline], 1,3-bis(carbazol-9-yl)benzene, polyaniline, polypyrrole, poly(p-)phenylene vinylene, aromatic tertiary amines, polynuclear aromatic tertiary amines, 4,4'-bis(p-carbazolyl)-1,1'-biphenyl compounds, N,N,N',N'-tetraarylbenzidine, PEDOT:PSS and its derivatives, polymethacrylate and its derivatives , poly (9,9-octylfluorene) and its derivatives, poly (spirofluorene) and its derivatives, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene, PEDOT, PEDOT:PSS, PEDOT:PSS doped with s-MoO3 derivatives, 4,4',4'-tris (N-3-methylphenyl-N-phenylamino) triphenylamine, tetracyanoquinodimethane, doped graphene, undoped graphene, C60, copper phthalocyanine, the second doped metal oxide particles, the second undoped metal oxide particles, the metal sulfide and the metal nitride one or more; and / or

[0127] The material of the electronic functional layer includes one or more of inorganic electronic functional materials and organic electronic functional materials. The inorganic electronic functional materials include one or more of the first doped metal oxide particles, the first undoped metal oxide particles, the IIB-VIA semiconductor material, the IIIA-VA semiconductor material and the IB-IIIA-VIA semiconductor material. The organic electronic functional materials include one or more of quinoxaline compounds, imidazole compounds, triazine compounds, fluorene-containing compounds, hydroxyquinoline compounds and fullerene derivatives.

[0128] In other embodiments, the hole functional layer includes a hole injection layer and / or a hole transport layer;

[0129] The electronic functional layer includes an electron injection layer and / or an electron transport layer.

[0130] It is understood that the optoelectronic device may be an upright optoelectronic device or an inverted optoelectronic device. The optoelectronic device may be a quantum dot optoelectronic device or an organic optoelectronic device.

[0131] In a sixth aspect, embodiments of the present application provide an electronic device comprising a film produced by the above-described film production method, or an optoelectronic device as described above. The electronic device can be any electronic product with a display function, including but not limited to smartphones, tablet computers, laptop computers, digital cameras, digital video cameras, smart wearable devices, smart weighing electronic scales, vehicle-mounted displays, televisions, or e-book readers. Examples of smart wearable devices include smart bracelets, smart watches, and virtual reality (VR) helmets.

[0132] Synthesis example 1

[0133] This synthesis example provides a method for synthesizing an organic compound HT-1.

[0134] HT-1 overall synthesis route:

[0135]

[0136] The synthesis method of HT-1 comprises the following steps:

[0137] (1) Synthesis of M3:

[0138] To a mixture of M1 (6.12 g, 29.1 mmol) and M2 (10.7 g, 37.7 mmol) in pyridine (100 mL) was added Pryride, 2-chloro-3,5-dinitropyridine (5.92 g, 29.1 mmol).

[0139] The substituent R1 in M2 is:

[0140]

[0141] The mixture was stirred at 115°C for 45 minutes, then cooled to room temperature. The solution was poured into a semi-saturated aqueous NaHCO₃ solution (250 mL) and extracted with ether (2 x 250 mL). The combined organic layers were washed with water (3 x 150 mL), dried over anhydrous sodium sulfate, filtered, and the solvent removed by rotary evaporation. The crude product was purified by column chromatography (silica gel, CH₂Cl₂, hexane) to yield 6.53 g of compound M3 (13.7 mmol, 47%).

[0142] (2) Synthesis of M4:

[0143] A THF solution (100 ml) of M3 (4.77 g, 10 mmol) was cooled to -78°C and protected from light. NBS (n-bromosuccinimide) (3.58 g, 20 mmol) was added over 5 minutes. The resulting suspension was stirred overnight, slowly warmed to room temperature, and concentrated under reduced pressure at room temperature. The crude product was purified by column chromatography and recrystallized from hot ethanol to yield 4.51 g of compound M4 (7.1 mmol, 71%) as pale yellow crystals.

[0144] (3) Synthesis of M5:

[0145] A 100 ml flask was charged with palladium catalyst Pd(dppf)Cl2 (0.15 mmol), KOAc (4.47 g, 15 mmol), and bis(pinacolato)diboron (3.17 g, 12.5 mmol), followed by purging with N2 three times. DMSO (50 ml) and M4 (3.17 g, 5.0 mmol) were then added. After stirring at 80°C for an appropriate period of time, the mixture was extracted with benzene, washed with water, and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography and recrystallized from ethyl acetate to yield 3.28 g of M5 (4.5 mmol, 90%) as a pale yellow powder.

[0146] (4) Synthetic polymers:

[0147] A 25 ml flask was charged with M5 (364 mg, 0.5 mmol), M6 (230 mg, 0.5 mmol) and 5 drops of Aliquat 336 phase transfer catalyst.

[0148] The substituent R2 in M6 is:

[0149]

[0150] The reaction flask was then purged with N2 three times, and 4 ml of tolulene in anhydrous toluene was added. Stirring was initiated, and the reaction mixture was heated to 95°C for 30 minutes. Then, under nitrogen protection, 4 mg of Pd(OAc)2 and 20 mg of Pd(PPh3)4 were rapidly added to the reaction mixture. After 30 minutes, 5 ml of a 2 mol / L aqueous solution of Na2CO3 was slowly added dropwise to the reaction mixture via syringe. The reaction mixture was then heated to 100°C for 4 hours. The reaction was terminated, and after cooling to room temperature, the reaction mixture was dripped dropwise into a stirred methanol solution to precipitate the polymer. The polymer solid was collected by filtration. The collected polymer solid was then extracted using a Soxhlet extractor with acetone and then hexane for 24 hours each to remove impurities and low-molecular-weight oligomers. Finally, the polymer was extracted with chlorobenzene, and the obtained polymer solution was concentrated using a rotary evaporator. The concentrated polymer chloroform solution was then added dropwise to a stirred methanol solution to reprecipitate. The polymer solid was collected by filtration and placed in a vacuum oven at 40°C for 24 hours. Depending on the substituents R1 and R2, the final desired polymer HT-1, HT-2, HT-3, HT-4 or HT-5 was obtained. In this synthesis example, polymer HT-1 (543 mg, 70%) was obtained. The number average molecular weight of polymer HT-1 was about 50,000, the molecular weight distribution was 1.51, and the degree of polymerization was 55-88.

[0151] The structural formula of polymer HT-1 is as follows:

[0152]

[0153] Synthesis example 2

[0154] This synthesis example provides a method for synthesizing an organic compound HT-2.

[0155] Compared with the synthesis method in Synthesis Example 1, the difference of this Synthesis Example is:

[0156] In Synthesis Example 1, the substituent R1 of M2 is replaced by:

[0157]

[0158] HT-2 was synthesized according to the other steps of Synthesis Example 1. The number average molecular weight of HT-2 was about 35,000, the molecular weight distribution was 1.60, and the degree of polymerization was 35-60;

[0159] The structural formula of polymer HT-2 is as follows:

[0160]

[0161] Synthesis example 3

[0162] This synthesis example provides a method for synthesizing an organic compound HT-3.

[0163] Compared with the synthesis method in Synthesis Example 1, the difference of this Synthesis Example is:

[0164] In Synthesis Example 1, the substituent R1 of M2 is replaced by:

[0165]

[0166] HT-3 was synthesized according to the other steps of Synthesis Example 1. The number average molecular weight of HT-3 was about 30,000, the molecular weight distribution was 1.82, and the degree of polymerization was 30-60;

[0167] The structural formula of polymer HT-3 is as follows:

[0168]

[0169] Synthesis example 4

[0170] This synthesis example provides a method for synthesizing an organic compound HT-4.

[0171] Compared with the synthesis method in Synthesis Example 1, the difference of this Synthesis Example is:

[0172] In Synthesis Example 1, the substituent R1 of M2 is replaced by:

[0173]

[0174] HT-4 was synthesized according to the other steps of Synthesis Example 1. The number average molecular weight of HT-4 was about 20,000, the molecular weight distribution was 1.45, and the degree of polymerization was 20-40;

[0175] The structural formula of polymer HT-4 is as follows:

[0176]

[0177] Synthesis example 5

[0178] This synthesis example provides a method for synthesizing an organic compound HT-5.

[0179] Compared with the synthesis method in Synthesis Example 1, the difference of this Synthesis Example is:

[0180] In Synthesis Example 1, the substituent R1 of M2 is replaced by:

[0181]

[0182] The substituent R2 in M6 is replaced by:

[0183] *-H,

[0184] HT-5 was synthesized according to the other steps of Synthesis Example 1. The number average molecular weight of HT-5 was about 20,000, the molecular weight distribution was 1.41, and the degree of polymerization was 25-35;

[0185] The structural formula of polymer HT-5 is as follows:

[0186]

[0187] Synthesis example 6

[0188] This synthesis example provides a method for synthesizing an organic compound HT-6.

[0189] The overall synthetic route of HT-6:

[0190]

[0191] The synthesis method of HT-6 comprises the following steps:

[0192] (1) Synthesis of M9:

[0193] A suspension of sodium hydride (0.42 g, 18 mmol) in THF (40 mL) was cooled to 0°C, and M7 pyrrole (1.34 g, 20 mmol) was added dropwise, followed by stirring for 5 min. After stirring for 25 min, a solution of M8 (6.46 g, 16.5 mmol) in THF (5 mL) was added dropwise to the reaction flask, forming a large amount of orange precipitate.

[0194] The substituent R3 in M8 is:

[0195]

[0196] The solution was then stirred overnight and slowly warmed to room temperature. After removing the solvent under reduced pressure, the resulting solid was suspended in ethyl acetate (100 mL) and subsequently extracted with diluted NaHCO₃ (100 mL), water (2 x 100 mL), and brine (100 mL). The organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The resulting oil was purified by column chromatography to yield 5.44 g (81%) of an oil.

[0197] (2) Synthesis of M10:

[0198] A solution of diisopropylamine (0.66 mL, 4.7 mmol) in THF (30 mL) was added to the reaction flask, which was cooled to -78°C. Butyllithium (2.5 mol / L in hexanes, 1.74 mL, 4.4 mmol) was then added dropwise. After stirring at -78°C for 5 minutes, the solution was slowly warmed to room temperature and reacted for 30 minutes. Subsequently, the reaction flask was cooled to -78°C again, and a solution of compound M9 (6.7 g, 2 mmol) in 20 mL of THF was added dropwise to the reaction flask. After 60 minutes, trimethyltin chloride (1.0 M in THF, 4.9 mL, 4.9 mmol) was added dropwise. The solution was slowly warmed to room temperature again and stirred overnight. The solution was concentrated under reduced pressure, and the resulting oil was filtered using a 30% solution of dichloromethane in hexanes. The product was quickly purified using a basic alumina silica gel column. Removal of the solvent yielded 12.1 g (91%) of an oil.

[0199] (3) Synthetic polymers:

[0200] Compound M10 (661 mg, 0.5 mmol), M6 (230 mg, 0.5 mmol), PdCl2(PPh3)2 (6.7 mg, 0.1 mmol), and toluene in anhydrous toluene were added to a reaction flask and heated at 120°C for 48 h. The color changed from light yellow to dark purple. The solution was poured into methanol (150 ml) and the precipitate was collected by filtration. The precipitate was extracted using a Soxhlet extractor with acetone and then hexane for 24 hours in each solvent to remove impurities and low-molecular-weight oligomers in the polymer. Finally, the polymer was extracted with chlorobenzene, and the obtained polymer solution was concentrated using a rotary evaporator. The concentrated polymer solution was added dropwise to a stirred methanol solution to reprecipitate, and the polymer solid was collected by filtration and placed in a vacuum oven at 40°C for 24 hours. Depending on the difference in R3, the final desired HT-6 or HT-7 polymer was obtained. In this synthesis example, polymer HT-6 (238 mg, 75%) was obtained. The number average molecular weight of polymer HT-6 was about 25,000, the molecular weight distribution was 1.79, and the degree of polymerization was 35-65.

[0201] The structural formula of polymer HT-6 is as follows:

[0202]

[0203] Synthesis Example 7

[0204] This synthesis example provides a method for synthesizing an organic compound HT-7.

[0205] Compared with the synthesis method in Synthesis Example 6, the difference of this Synthesis Example is:

[0206] In Synthesis Example 6, the substituent R3 in M8 is replaced by:

[0207]

[0208] HT-7 was synthesized according to the other steps of Synthesis Example 6. The number average molecular weight of HT-7 was about 40,000, the molecular weight distribution was 1.57, and the degree of polymerization was 60-85;

[0209] The structural formula of polymer HT-7 is as follows:

[0210]

[0211] The present application will be described in detail below through specific examples. The following examples are only some examples of the present application and are not limitations of the present application.

[0212] Organic Compound Example 1

[0213] This example provides an organic compound HT-1 prepared by the above-mentioned Synthesis Example 1. The number average molecular weight of HT-1 is about 50,000, the molecular weight distribution is 1.51, and the degree of polymerization is 55-88. The structural formula of the organic compound HT-1 is as follows:

[0214]

[0215] Organic Compound Example 2

[0216] This example provides an organic compound HT-2 prepared by the above-mentioned Synthesis Example 2. The number average molecular weight of HT-2 is about 35,000, the molecular weight distribution is 1.60, and the degree of polymerization is 35-60. The structural formula of the organic compound HT-2 is as follows:

[0217]

[0218] Organic Compound Example 3

[0219] This example provides an organic compound HT-3 prepared by the above-mentioned Synthesis Example 3. The number average molecular weight of HT-3 is about 30,000, the molecular weight distribution is 1.82, and the degree of polymerization is 30-60. The structural formula of the organic compound HT-3 is as follows:

[0220]

[0221] Organic Compound Example 4

[0222] This example provides an organic compound HT-4 prepared by the above-mentioned Synthesis Example 4. The number average molecular weight of HT-4 is about 20,000, the molecular weight distribution is 1.45, and the degree of polymerization is 20-40. The structural formula of the organic compound HT-4 is as follows:

[0223]

[0224] Organic Compound Example 5

[0225] This example provides an organic compound HT-5 prepared by the above-mentioned Synthesis Example 5. The number average molecular weight of HT-5 is about 20,000, the molecular weight distribution is 1.41, and the degree of polymerization is 25-35. The structural formula of the organic compound HT-5 is as follows:

[0226]

[0227] Organic Compound Example 6

[0228] This example provides an organic compound HT-6 prepared by the above-mentioned Synthesis Example 6. The number average molecular weight of HT-6 is about 25,000, the molecular weight distribution is 1.79, and the degree of polymerization is 35-65. The structural formula of the organic compound HT-6 is as follows:

[0229]

[0230] Organic Compound Example 7

[0231] This example provides an organic compound HT-7 prepared by the above-mentioned Synthesis Example 7. The number average molecular weight of HT-7 is about 40,000, the molecular weight distribution is 1.57, and the degree of polymerization is 60-85. The structural formula of the organic compound HT-7 is as follows:

[0232]

[0233] Organic Compound Comparative Example 1

[0234] This comparative example provides a TFB material.

[0235] Performance Testing

[0236] 200 g of the polymers of Organic Compound Examples 1-7 and Organic Compound Comparative Example 1 were respectively weighed, and 20 ml of chlorobenzene was added to each of them. The mixture was stirred at 25° C. for 6 h until fully dissolved to obtain a polymer solution. The polymer solution was deposited on the hole injection layer of a single hole device. The structure of the single hole device is as follows:

[0237] ITO / PEDDOT:PSS / polymer / QD / MoO x / Ag, the hole mobility of the polymer was detected using a detection device, and the structure is shown in Table 1.

[0238] The hole mobility of the hole transport layer is recorded by the space charge limited current (SCLC) method, which can be described by the Mott-Gurney equation: J = 9με0ε r V 2 / (8d 3 ).

[0239] Where J is the current density, μ is the hole mobility, and ε0 is the vacuum dielectric constant (8.85×10 -12 F / m), ε r is the dielectric constant of the material (usually approximately taken as 3 for organic semiconductors), V is the applied bias voltage, and d is the film thickness.

[0240] Table 1

[0241] organic compounds Hole mobility Organic Compound Example 1 HT-1 <![CDATA[8.1ⅹ10 -4 ]]> Organic Compound Example 2 HT-2 <![CDATA[3.4ⅹ10 -3 ]]> Organic Compound Example 3 HT-3 <![CDATA[3.1ⅹ10 -3 ]]> Organic Compound Example 4 HT-4 <![CDATA[2.7ⅹ10 -3 ]]> Organic Compound Example 5 HT-5 <![CDATA[9.6ⅹ10 -4 ]]> Organic Compound Example 6 HT-6 <![CDATA[8.1ⅹ10 -4 ]]> Organic Compound Example 7 HT-7 <![CDATA[2.1ⅹ10 -3 ]]> Organic Compound Comparative Example 1 PTPB <![CDATA[5.4ⅹ10 -4 ]]>

[0242] From Table 1 we can see that:

[0243] The polymers of organic compound examples 1-7 exhibit significantly higher hole mobility than organic compound comparative example 1, demonstrating superior hole transport properties. In particular, the hole mobility of organic compound examples 2-4 and 7 is 10 times greater than that of the existing material PTPB, making them more suitable for use as hole transport layer materials compared to existing materials.

[0244] Film Example 1

[0245] This embodiment provides a film and a method for preparing the same. The film comprises a polymer HT-1A, the number average molecular weight of HT-1A being approximately 35,000, the molecular weight distribution being 1.51, and the structural formula of HT-1A being as follows:

[0246]

[0247] The method for preparing the film comprises the following steps:

[0248] S1.1. Weigh 200 g of organic compound HT-1, add 20 ml of chlorobenzene, and stir at 25°C for 6 h until fully dissolved to prepare a first functional liquid, and deposit the first functional liquid;

[0249] S1.2. Heat the deposited first functional liquid at 300° C. for 30 minutes to obtain a thin film including HT-1A.

[0250] Film Example 2

[0251] This embodiment provides a film and a preparation method thereof. Compared with the film in Film Example 1, the film in this embodiment is different in that the material of the film includes a polymer HT-2A. The number average molecular weight of HT-2A is about 24,000, the molecular weight distribution is 1.60, and the structural formula of HT-2A is as follows:

[0252]

[0253] Compared with the film preparation method in the film embodiment 1, the film preparation method in this embodiment is different in that:

[0254] Replace step S1.1 with “weigh 200 g of organic compound HT-2, add 20 ml of chlorobenzene, stir at 25° C. for 6 h until fully dissolved to prepare a first functional liquid, and deposit the first functional liquid.”

[0255] Film Example 3

[0256] This embodiment provides a film and a preparation method thereof. Compared with the film in Film Example 1, the film in this embodiment is different in that the material of the film includes a polymer HT-3A, the number average molecular weight of HT-3A is about 21,000, the molecular weight distribution is 1.82, and the structural formula of HT-3A is as follows:

[0257]

[0258] Compared with the film preparation method in film embodiment 1, the difference of the film preparation method in this embodiment is that: step S1.1 is replaced by "weighing 200g of organic compound HT-3, adding 20ml of chlorobenzene, stirring at 25°C for 6h until fully dissolved, preparing the first functional liquid, and depositing the first functional liquid".

[0259] Film Example 4

[0260] This embodiment provides a film and a preparation method thereof. Compared with the film in Film Example 1, the film in this embodiment is different in that the material of the film includes a polymer HT-4A, the number average molecular weight of HT-4A is about 15,000, the molecular weight distribution is 1.45, and the structural formula of HT-4A is as follows:

[0261]

[0262] Compared with the film preparation method in film example 1, the difference of the film preparation method in this embodiment is that: step S1.1 is replaced by "weighing 200g of organic compound HT-4, adding 20ml of chlorobenzene, stirring at 25°C for 6h until fully dissolved, preparing the first functional liquid, and depositing the first functional liquid".

[0263] Film Example 5

[0264] This embodiment provides a film and a method for preparing the same. Compared to the film in Film Example 1, the film in this embodiment differs in that the film comprises a polymer HT-5A, the number average molecular weight of HT-5A being approximately 13,000 and the molecular weight distribution being 1.41. The structural formula of HT-5A is as follows:

[0265]

[0266] Compared with the film preparation method in film embodiment 1, the difference of the film preparation method in this embodiment is that: step S1.1 is replaced by "weighing 200g of organic compound HT-5, adding 20ml of chlorobenzene, stirring at 25°C for 6h until fully dissolved, preparing the first functional liquid, and depositing the first functional liquid".

[0267] Film Example 6

[0268] This embodiment provides a film and a preparation method thereof. Compared with the film in Film Example 1, the film in this embodiment is different in that the material of the film includes a polymer HT-6A, the number average molecular weight of HT-6A is about 14,500, the molecular weight distribution is 1.79, and the structural formula of HT-6A is as follows:

[0269]

[0270] Compared with the film preparation method in film embodiment 1, the difference of the film preparation method in this embodiment is that: step S1.1 is replaced by "weighing 200g of organic compound HT-6, adding 20ml of chlorobenzene, stirring at 25°C for 6h until fully dissolved, preparing the first functional liquid, and depositing the first functional liquid".

[0271] Film Example 7

[0272] This embodiment provides a film and a preparation method thereof. Compared with the film in Film Example 1, the film in this embodiment is different in that the material of the film includes a polymer HT-7A, the number average molecular weight of HT-7A is about 25,000, the molecular weight distribution is 1.57, and the structural formula of HT-7A is as follows:

[0273]

[0274] Compared with the film preparation method in film embodiment 1, the difference of the film preparation method in this embodiment is that: step S1.1 is replaced by "weighing 200g of organic compound HT-7, adding 20ml of chlorobenzene, stirring at 25°C for 6h until fully dissolved, preparing the first functional liquid, and depositing the first functional liquid".

[0275] Film Comparative Example 1

[0276] This comparative example provides a thin film and a preparation method thereof. Compared with the thin film in thin film embodiment 1, the difference of the thin film in this embodiment is that: step 1 is replaced by "weighing 200g of organic compound PTPB, adding 20ml of chlorobenzene, stirring at 25°C for 6h until fully dissolved, preparing a first functional liquid, and depositing the first functional liquid".

[0277] Performance Testing

[0278] The film examples 1-7 and the film comparative example 1 were used as the hole transport layer of the single hole device. The structure of the single hole device was: ITO / PEDDOT:PSS / film / QD / MoO x / Ag, the hole mobility of the polymer was detected using a detection device, and the structure is shown in Table 2.

[0279] The hole mobility of the hole transport layer material is recorded by the space charge limited current (SCLC) method, which can be described by the Mott-Gurney equation: J = 9με0ε r V 2 / (8d 3 ).

[0280] Where J is the current density, μ is the hole mobility, and ε0 is the vacuum dielectric constant (8.85×10 -12 F / m), ε r is the dielectric constant of the material (usually approximately taken as 3 for organic semiconductors), V is the applied bias voltage, and d is the film thickness.

[0281] Table 2

[0282] Thin film material Hole mobility Film Example 1 HT-1A <![CDATA[4.6ⅹ10 -3 ]]> Film Example 2 HT-2A <![CDATA[8.4ⅹ10 -3 ]]> Film Example 3 HT-3A <![CDATA[7.5ⅹ10 -3 ]]> Film Example 4 HT-4A <![CDATA[6.3ⅹ10 -3 ]]> Film Example 5 HT-5A <![CDATA[5.2ⅹ10 -3 ]]> Film Example 6 HT-6A <![CDATA[4.3ⅹ10 -3 ]]> Film Example 7 HT-7A <![CDATA[5.8ⅹ10 -3 ]]> Film Comparative Example 1 PTPB <![CDATA[5.3ⅹ10 -4 ]]>

[0283] From Table 2 we can see that:

[0284] Compared to Comparative Example 1, the hole mobility of Film Examples 1-7 was significantly improved by an order of magnitude, demonstrating superior hole transport performance and enhancing the conductivity of the hole transport layer. Furthermore, the hole mobility of Film Examples 1-7 was approximately 50% higher than that of Organic Compound Examples 1-7. This is primarily due to the significant steric hindrance between polymers with long side chains, which, upon heating, removes the insulating long side chains, resulting in improved conductivity.

[0285] Device Example 1

[0286] Reference Figure 1This embodiment provides a photoelectric device and a method for preparing the same. The photoelectric device includes an anode 1, a hole transport layer 5, a light-emitting layer 6, an electron transport layer 4, an electron injection layer 3, and a cathode 2, which are arranged in sequence. The hole transport layer is an HT-1A thin film.

[0287] The method for preparing the optoelectronic device comprises the following steps:

[0288] S1.1. Provide an ITO anode substrate. Ultrasonic clean the anode substrate with acetone and ethanol for 15 minutes, then rinse again with deionized water. Dry on a hot plate at 150°C for 10 minutes, and irradiate with ultraviolet light for 20 minutes to increase the work function and surface energy of the anode substrate.

[0289] S1.2. Spin-coat the anode substrate with a first functional liquid containing 10 mg / ml of HT-1 at a speed of 2000 rpm for 30 seconds. Heat the solution at 300°C for 30 minutes to decompose and remove the HT-1 side chains. Then, evacuate the chamber for 15 minutes to obtain a 20 nm thick HT-1A thin film, i.e., the hole transport layer.

[0290] S1.3. Spin-coat a 40 mg / mL CdZnSe quantum dot solution on the hole transport layer at a speed of 1500 rpm for 30 s and anneal at 100°C for 5 min to obtain a light-emitting layer.

[0291] S1.4. Spin-coat a 20 mg / mL ZnO-ethanol solution on the light-emitting layer at a speed of 4000 rpm for 30 s, and anneal at 80°C for 10 min to obtain an electron transport layer with a thickness of 70 nm.

[0292] S1.5, spin coating the CsF material with a concentration of 20 mg / mL on the light-emitting layer at a spin coating speed of 3000 rpm for 30 min, and annealing at 150°C for 10 min to obtain an electron injection layer with a thickness of 10 nm;

[0293] S1.6. Vapor-deposit Ag material on the electron injection layer at a rate of 1 Å / s for 100 s to obtain a cathode with a thickness of 100 nm.

[0294] Encapsulation is performed to obtain a photoelectric device.

[0295] Device Example 2

[0296] This embodiment provides a photoelectric device and a preparation method thereof. Compared with the photoelectric device in Example 1, the photoelectric device in this embodiment is different in that the hole transport layer is an HT-2A thin film.

[0297] Compared with the preparation method of the optoelectronic device in Example 1, the difference of the preparation method of the optoelectronic device in this embodiment is that: step S1.2 is replaced by: "Spin-coat the first functional liquid including 10 mg / ml of HT-2 on the anode substrate at a spin coating speed of 2000 rpm for 30 seconds, and heat at 230°C for 30 minutes to decompose and remove the HT-2 side chain, and then evacuate the vacuum chamber for 15 minutes to obtain a HT-2A thin film with a thickness of 20 nm, i.e., the hole transport layer."

[0298] Device Example 3

[0299] This embodiment provides a photoelectric device and a preparation method thereof. Compared with the photoelectric device in Example 1, the photoelectric device in this embodiment is different in that the hole transport layer is an HT-3A thin film.

[0300] Compared with the preparation method of the optoelectronic device in Example 1, the difference of the preparation method of the optoelectronic device in this embodiment is that: step S1.3 is replaced by: "Spin-coat the first functional liquid including 10 mg / ml of HT-3 on the anode substrate at a spin coating speed of 2000 rpm for 30 seconds, and heat at 230°C for 30 minutes to decompose and remove the HT-3 side chain, and then evacuate the vacuum chamber for 15 minutes to obtain a HT-3A thin film with a thickness of 20 nm, i.e., the hole transport layer."

[0301] Device Example 4

[0302] This embodiment provides a photoelectric device and a preparation method thereof. Compared with the photoelectric device in Example 1, the photoelectric device in this embodiment is different in that the hole transport layer is an HT-4A thin film.

[0303] Compared with the preparation method of the optoelectronic device in Example 1, the difference of the preparation method of the optoelectronic device in this embodiment is that: step S1.2 is replaced by: "Spin-coat the first functional liquid including 10 mg / ml of HT-4 on the anode substrate at a spin coating speed of 2000 rpm for 30 seconds, and heat at 200°C for 30 minutes to decompose and remove the HT-4 side chain, and then evacuate the vacuum chamber for 15 minutes to obtain a HT-4A thin film with a thickness of 20 nm, i.e., the hole transport layer."

[0304] Device Example 5

[0305] This embodiment provides a photoelectric device and a preparation method thereof. Compared with the photoelectric device in Example 1, the photoelectric device in this embodiment is different in that the hole transport layer is an HT-5A thin film.

[0306] Compared with the preparation method of the optoelectronic device in Example 1, the difference of the preparation method of the optoelectronic device in this embodiment is that: step S1.2 is replaced by: "Spin-coat the first functional liquid including 10 mg / ml of HT-5 on the anode substrate at a spin coating speed of 2000 rpm for 30 seconds, and heat at 200°C for 30 minutes to decompose and remove the HT-5 side chain, and then evacuate the vacuum chamber for 15 minutes to obtain a HT-5A thin film with a thickness of 20 nm, i.e., the hole transport layer."

[0307] Device Example 6

[0308] This embodiment provides a photoelectric device and a preparation method thereof. Compared with the photoelectric device in Example 1, the photoelectric device in this embodiment is different in that the hole transport layer is an HT-6A thin film.

[0309] Compared with the preparation method of the optoelectronic device in Example 1, the difference of the preparation method of the optoelectronic device in this embodiment is that: step S1.2 is replaced by: "Spin-coat the first functional liquid including 10 mg / ml of HT-6 on the anode substrate at a spin coating speed of 2000 rpm for 30 seconds, and heat at 230°C for 30 minutes to decompose and remove the HT-6 side chain, and then evacuate the vacuum chamber for 15 minutes to obtain a HT-6A thin film with a thickness of 20 nm, i.e., the hole transport layer."

[0310] Device Example 7

[0311] This embodiment provides a photoelectric device and a preparation method thereof. Compared with the photoelectric device in Example 1, the photoelectric device in this embodiment is different in that the hole transport layer is an HT-7A thin film.

[0312] Compared with the preparation method of the optoelectronic device in Example 1, the difference of the preparation method of the optoelectronic device in this embodiment is that: step S1.2 is replaced by: "Spin-coat the first functional liquid including 10 mg / ml of HT-7 on the anode substrate at a spin coating speed of 2000 rpm for 30 seconds, and heat at 230°C for 30 minutes to decompose and remove the HT-7 side chain, and then evacuate the vacuum chamber for 15 minutes to obtain a HT-7A thin film with a thickness of 20 nm, i.e., the hole transport layer."

[0313] Device Comparative Example 1

[0314] This embodiment provides a photoelectric device and a preparation method thereof. Compared with the photoelectric device in Example 1, the photoelectric device in this embodiment is different in that the hole transport layer is a TFB thin film.

[0315] This embodiment provides a photoelectric device and a preparation method thereof. Compared with the preparation method of the photoelectric device in Example 1, the difference in the preparation method of the photoelectric device in this embodiment is that: step S1.2 is replaced by: "Spin-coat 10 mg / ml TFB solution on the anode substrate at a spin-coating speed of 2000 rpm for 30 seconds, and anneal at 230°C for 20 minutes to obtain a hole transport layer with a thickness of 20 nm."

[0316] TFB:

[0317]

[0318] Device Comparative Example 2

[0319] Compared with the optoelectronic device in Example 1, the optoelectronic device in this embodiment is different in that the hole transport layer is a PTPB thin film.

[0320] Compared with the preparation method of the optoelectronic device in Example 1, the difference of the preparation method of the optoelectronic device in this embodiment is that: step S1.2 is replaced by: "Spin coat 10 mg / ml PTPB solution on the anode substrate at a spin coating speed of 2000 rpm for 30 seconds, and anneal at 200°C for 20 minutes to obtain a hole transport layer with a thickness of 20 nm."

[0321] PTPB:

[0322]

[0323] Performance Testing

[0324] The current efficiency and lifespan T95@1000nit tests were performed on the optoelectronic devices of device examples 1 to 7 and device comparative examples 1 to 2.

[0325] The test method for current efficiency is:

[0326] The wavelength was scanned from 0V to 7V at 0.2V, and the current (A) and brightness (nit / m 2 ), and obtain the current efficiency test value.

[0327] Device life (τ95@L 1000 )The test method is:

[0328] Device τ95@L 1000 The lifespan is measured by accelerated life test, measuring and recording the device brightness and lighting time at a constant current of 2mA, and the corresponding lifespan of the device is obtained. The τ95@L is calculated by the formula 1000 .

[0329] Place the device in the life tester, set the device current to 2mA, and measure the brightness of the device; perform life test using the life test system, collect light intensity through silicon photodiodes, power the device through Keithley3706A, and start the test by controlling the test software. The test interval is 1min; read the maximum brightness L on the life curve max , the measured value of device life τ95@L max , put it into the accelerated life test formula and calculate τ95@L 1000 .

[0330] The life acceleration formula is:

[0331]

[0332] Among them, T max is the maximum brightness value L on the curve max Corresponding time; T 95 is the maximum brightness value L on the curve max The time corresponding to 95% of the brightness of the device. in and time T in Draw a time-brightness curve for the starting point. According to the QLED display life estimation formula, the brightness is calculated to be 1000cd / m 2 Device lifetime τ95@L 1000 :

[0333]

[0334] Where L0 is the initial brightness; τ is the brightness decay life; α is the acceleration coefficient, which is taken as 1.7 in this case; C is a constant. In QLED display devices, when the maximum brightness values ​​are L max and L 1000 =1000cd / cm2, the corresponding lifetimes when the decay reaches 95% are τ95@L max and τ95@L 1000 ,Right now

[0335]

[0336] See Table 3 for test results.

[0337] Table 3:

[0338]

[0339] From Table 3 we can see that:

[0340] Compared with the devices of Comparative Examples 1 and 2, the devices of Examples 1-7 have all had significant improvements in current efficiency to varying degrees, and the difference in number average molecular weight leads to different current efficiencies of the devices. The devices of Examples 1-7 have improved lifespans by 15-67, respectively. On the basis of the existing technology, the lowest lifespan increase is 29.4%, and the highest increase is 129%; and there is a slight improvement in lifespan. The reason is that Examples 1-7 decompose the ester groups on the side chains of the organic compounds in the first functional liquid by heating, removing longer side chains. These longer side chains have insulating properties, thereby improving the conductivity of the hole transport layer; and, thin film Examples 1-7 are all improved by an order of magnitude on the basis of existing materials, overcoming the problem that the mobility of the existing organic hole transport layer is one order of magnitude lower than that of the inorganic electron transport layer, reducing the imbalance of carriers in the optoelectronic device, balancing the carriers, reducing the accumulation of electrons between the hole transport layer and the light-emitting layer, and reducing damage to the hole transport layer material.

[0341] At the same time, according to Examples 1-7, it can be seen that the current efficiency and the device service life have the same change trend. As the current efficiency increases, the device service life is also correspondingly increased.

[0342] The above is a detailed introduction to the embodiments of the present application. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the method and core idea of ​​the present application. At the same time, for those skilled in the art, based on the ideas of the present application, there may be changes in the specific implementation methods and application scope. In summary, the content of this specification should not be understood as a limitation on the present application.

Claims

1. An organic compound, characterized in that It has a structure as shown in general formula (I): in: R1 is selected from a straight or branched chain alkyl group containing 1 to 24 carbon atoms; AR1 is selected from one or more of a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms; AR2 is selected from: a substituted or unsubstituted aromatic amine group containing 6 to 60 ring atoms; n is: 20-85.

2. The organic compound according to claim 1, characterized in that R1 is selected from a straight chain or branched chain alkyl group containing 10 to 16 carbon atoms; and / or AR1 is selected from the group consisting of substituted or unsubstituted fluorenyl, spirobifluorenyl, carbazole, thiophene, bithiophene, condensed ring thiophene, benzofuran and pyrrole; and / or AR2 is selected from one of substituted or unsubstituted triphenylamine, methoxytriphenylamine and diphenylamine.

3. The organic compound according to claim 1, characterized in that The organic compound has a structure shown in any of the following structural formulas:

4. A film, characterized in that: The material of the film includes at least one organic compound having a structure such as general formula (II): in: AR1 is selected from: one or more of a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms; AR2 is selected from: a substituted or unsubstituted aromatic amine group containing 6 to 60 ring atoms; n is: 20-85.

5. The film according to claim 5, characterized in that AR1 is selected from the group consisting of substituted or unsubstituted fluorenyl, spirobifluorenyl, carbazole, thiophene, bithiophene, condensed ring thiophene, benzofuran and pyrrole; and / or AR2 is selected from one of substituted or unsubstituted triphenylamine, methoxytriphenylamine and diphenylamine.

6. The film according to claim 4, characterized in that The material of the film includes one or more of the organic compounds shown below:

7. A method for preparing a thin film, characterized in that: Includes steps: depositing a first functional liquid; as well as thermally treating the deposited first functional liquid to obtain a thin film; The first functional liquid includes an organic compound having a structure as shown in general formula (I): Wherein, R1 is selected from a straight chain or branched chain alkyl group containing 1 to 24 carbon atoms; AR1 is selected from one or more of a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms; AR2 is selected from substituted or unsubstituted aromatic amine groups containing 6 to 60 ring atoms; n is: 20-85.

8. The method for preparing a thin film according to claim 7, characterized in that: R1 is selected from a straight chain or branched chain alkyl group containing 10 to 16 carbon atoms; and / or AR1 is selected from the group consisting of substituted or unsubstituted fluorenyl, spirobifluorenyl, carbazole, thiophene, bithiophene, fused-ring thiophene, benzofuran and pyrrole; and / or AR2 is selected from the group consisting of substituted or unsubstituted triphenylamine, methoxytriphenylamine and diphenylamine.

9. The method for preparing a thin film according to claim 7, characterized in that: R1 is selected from one of the following structures: and / or AR1 is selected from substituted or unsubstituted: fluorenyl or pyrrole; and / or AR2 is selected from substituted or unsubstituted: triphenylamine; * indicates the attachment site.

10. The thin film preparation method according to claim 7, characterized in that: The temperature of the heat treatment is 150-300° C., and the time of the heat treatment is 30-60 minutes.

11. A photoelectric device, characterized in that: include: An anode and a cathode arranged opposite to each other; An excitation layer, disposed between the anode and the cathode; as well as A hole functional layer is disposed between the anode and the light-emitting layer; Wherein, the hole functional layer comprises a film as described in any one of claims 4-6, or a film prepared by a film preparation method as described in any one of claims 7-10.

12. The optoelectronic device according to claim 11, characterized in that: It also includes an electronic functional layer, which is arranged between the cathode and the light-emitting layer; and / or The anode and cathode each independently include a doped metal oxide electrode, a composite electrode, a graphene electrode, a carbon nanotube electrode, a metal single substance electrode or an alloy electrode. The material of the doped metal oxide electrode includes one or more of indium-doped tin oxide, fluorine-doped tin oxide, antimony-doped tin oxide, aluminum-doped zinc oxide, gallium-doped zinc oxide, indium-doped zinc oxide, magnesium-doped zinc oxide, aluminum-doped magnesium oxide, and cadmium-doped zinc oxide. The composite electrode includes AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, TiO2 / Ag / TiO2, TiO2 / Al / TiO2, ZnS / Ag / ZnS, ZnS / Al / ZnS, Ca / Al, LiF / Ca, LiF / Al, BaF2 / Al, CsF / Al, CaCO3 / Al or BaF2 / Ca / Al, the material of the metal single substance electrode includes one or more of Ag, Ni, Pt, Au, Ir, Cu, Mo, Al, Ca, Mg and Ba, and the alloy electrode includes Au:Mg alloy electrode or Ag:Mg alloy electrode; The material of the excitation layer includes one or more of an organic light-emitting material and a quantum dot light-emitting material, and the organic light-emitting material includes one or more of 4,4'-bis(N-carbazole)-1,1'-biphenyl:tri[2-(p-tolyl)pyridine iridium(III), 4,4',4"-tri(carbazole-9-yl)triphenylamine:tri[2-(p-tolyl)pyridine iridium, diaromatic anthracene derivatives, distilbene aromatic derivatives, pyrene derivatives, fluorene derivatives, TBPe fluorescent materials, TTPX fluorescent materials, TBRb fluorescent materials, DBP fluorescent materials, delayed fluorescent materials, TTA materials, thermally activated delayed materials, polymers containing covalent bonds of BN, hybrid localized charge transfer excited state materials, exciplex light-emitting materials, polyacetylene and its derivatives, polyparaphenylene and its derivatives, polythiophene and its derivatives, polyfluorene and its derivatives;The quantum dot luminescent material includes one or more of a single structure quantum dot, a core-shell structure quantum dot and a perovskite semiconductor material. 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 independently selected from one or more of II-VI group compounds, IV-VI group compounds, III-V group compounds and I-III-VI group compounds. The II-VI group compounds include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, Zn STe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and HgZnSTe, and the IV-VI group compound includes SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, One or more of PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, SnPbSTe, the III-V group compound includes 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, GaAlN As, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs and InAlPSb, the I-III-VI group compound includes one or more of CuInS2, CuInSe2 and AgInS2; the perovskite semiconductor material includes a doped or undoped inorganic perovskite semiconductor or an organic-inorganic hybrid perovskite semiconductor, and the general structural formula of the inorganic perovskite semiconductor is AMX3, wherein A is Cs; + ions, M is a divalent metal cation, including 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, X is a halogen anion, including Cl - Br - ,I - One or more of; the general structural formula of the organic-inorganic hybrid perovskite semiconductor is BMX3, wherein B is an organic amine cation, including CH3(CH2) n-2 NH3 + or [NH3(CH2) n NH3] 2+ , where n≥2, M is a divalent metal cation, including 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, X is a halogen anion, including Cl - Br - ,I - One or more of; and / or The material of the hole functional layer also includes 4,4'-N,N'-dicarbazolyl-biphenyl, poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine], 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, poly(N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine), N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-spiro, N,N'-bis(4-(N,N'-diphenyl-amino)phenyl triphenylamine, 4,4',4'-tri(N-carbazolyl)-triphenylamine, 4,4',4'-tri(N-3-methylphenyl-N-phenylamino)triphenylamine, poly[(9,9'-dioctylfluorene-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))], poly(N-vinylcarbazole) and its derivatives, N,N'-di(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4-4'-diamine, spiro NPB, poly(phenylene vinylene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene], poly [2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylene vinylene], 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene, 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline], 1,3-bis(carbazol-9-yl)benzene, polyaniline, polypyrrole, poly(p-)phenylene vinylene, aromatic tertiary amine, polynuclear aromatic tertiary amine, 4,4'-bis(p-carbazyl)-1,1'-biphenyl compound, N,N,N',N'-tetraarylbenzidine, PEDOT:PSS and its derivatives, polymethacrylate and its derivatives , poly (9,9-octylfluorene) and its derivatives, poly (spirofluorene) and its derivatives, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene, PEDOT, PEDOT:PSS, PEDOT:PSS doped with s-MoO3 derivatives, 4,4',4'-tris (N-3-methylphenyl-N-phenylamino) triphenylamine, tetracyanoquinodimethane, doped graphene, undoped graphene, C60, copper phthalocyanine, the second doped metal oxide particles, the second undoped metal oxide particles, the metal sulfide and the metal nitride one or more; and / or The material of the electronic functional layer includes one or more of inorganic electronic functional materials and organic electronic functional materials. The inorganic electronic functional materials include one or more of the first doped metal oxide particles, the first undoped metal oxide particles, the IIB-VIA semiconductor materials, the IIIA-VA semiconductor materials and the IB-IIIA-VIA semiconductor materials. The organic electronic functional materials include one or more of quinoxaline compounds, imidazole compounds, triazine compounds, fluorene-containing compounds, hydroxyquinoline compounds and fullerene derivatives.

13. An electronic device, characterized in that: It comprises a film prepared by the film preparation method according to any one of claims 7 to 10, or a photoelectric device according to any one of claims 11 or 12.

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