Organic compound, composition and optoelectronic device

Abstract

The invention discloses an organic compound, a composition and a photoelectric device, the organic compound takes a # imgabs0 # ring as a core structure, and the organic compound comprises an electron donating group, can realize effective utilization of high-energy triplet excitons, activates a reverse intersystem crossing channel, breaks through the 25% exciton utilization rate limitation of a traditional organic fluorescent material, and has a good application prospect. The organic compound can make the exciton utilization rate reach 100%, can be used for preparing photoelectric devices, and can effectively improve the performance of the photoelectric devices.

Description

Technical Field

[0001] The present application relates to the technical field of organic materials, and in particular to an organic compound, a composition and a photoelectric device. Background Art

[0002] Organic Light-Emitting Diode (OLED) has the characteristics of self-luminescence, high brightness, wide viewing angle, high contrast, flexibility, low energy consumption, fast response speed, etc., and is widely used in display devices, lighting and other technical fields. In order to improve the device efficiency and device life of OLED, OLED generally has a multilayer structure. For example, OLED includes an anode, a hole functional layer, a light-emitting layer, an electronic functional layer and a cathode stacked in sequence. The light-emitting principle of OLED is: when a voltage is applied between the anode and the cathode, electrons are injected from the cathode to the light-emitting layer via the electronic functional layer, and holes are injected from the anode to the light-emitting layer via the hole functional layer. Electrons and holes recombine in the light-emitting area to form excitons, and the recombined excitons release photons in the form of radiation transition, thereby emitting light. After years of development, OLED has made great progress in performance indicators and has shown great potential for application development, but the performance of OLED needs to be further improved. Summary of the invention

[0003] In view of the deficiencies of the prior art, the present application provides an organic compound, a composition and a photoelectric device.

[0004] In a first aspect, the present application provides an organic compound having a structure shown in the following general formula (I):

[0005]

[0006] In the general formula (I), Ar 1 and Ar 2 are independently selected from aromatic rings having 6 to 30 ring atoms;

[0007] R 1 Selected from electron donating groups, R 2 An aryl group having 6 to 30 ring atoms which is unsubstituted or substituted by at least one substituent, and a heteroaryl group having 5 to 30 ring atoms which is unsubstituted or substituted by at least one substituent;

[0008] Wherein, each occurrence of the substituent is independently selected from -D, a halogen group, -OH, -NH 2 , -SH, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C1-C30 alkoxy, C1-C30 alkoxycarbonyl, C1-C30 alkylacyloxy, or a combination of these groups.

[0009] In a second aspect, the present application provides a method for preparing an organic compound, which is used to prepare the organic compound as described in the first aspect, and the method for preparing the organic compound comprises the following steps:

[0010] (A1) The general formula R 1 -X 1 The first compound and diboric acid pinacol ester are mixed to perform a first reaction to obtain a second compound;

[0011] (A2) The general formula is R 2 -X 2 The third compound and diboric acid pinacol ester are mixed to carry out a second reaction to obtain a fourth compound;

[0012] (A3) mixing the fourth compound and the fifth compound to perform a third reaction to obtain a sixth compound;

[0013] (A4) mixing the second compound and the sixth compound to carry out a fourth reaction to obtain an organic compound having a structure represented by the general formula (I);

[0014] Wherein, the second compound has the structure shown in the following formula (II):

[0015]

[0016] The fourth compound has a structure shown in the following formula (III):

[0017]

[0018] The fifth compound has a structure shown in the following formula (IV):

[0019]

[0020] The sixth compound has a structure shown by the following general formula (V):

[0021]

[0022] X 1 To X 4 are independently selected from F, Cl, Br or I.

[0023] In a third aspect, the present application provides a composition, comprising the organic compound as described in the first aspect, or the organic compound prepared by the preparation method as described in the second aspect.

[0024] In a fourth aspect, the present application provides an optoelectronic device, comprising:

[0025] an anode and a cathode disposed opposite to each other; and

[0026] A plurality of functional layers are disposed between the anode and the cathode;

[0027] Among them, the material of at least one of the multiple functional layers includes an organic compound as described in any one of the first aspects, or an organic compound prepared by any one of the preparation methods described in the second aspect, or at least one of the multiple functional layers is prepared using the composition described in the third aspect.

[0028] The organic compounds provided in this application can effectively improve the performance of optoelectronic devices. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] The technical solution and other beneficial effects of the present application will be made apparent by describing in detail the specific implementation methods of the present application in conjunction with the accompanying drawings.

[0030] Figure 1 A schematic diagram of a process for preparing a compound provided in an embodiment of the present application.

[0031] Figure 2 A schematic structural diagram of the first optoelectronic device provided in an embodiment of the present application.

[0032] Figure 3 A schematic diagram of the structure of a second optoelectronic device provided in an embodiment of the present application.

[0033] Figure 4 These are the ultraviolet absorption spectra of organic compounds M1 to M4.

[0034] Figure 5 Graphs showing fluorescence emission spectra of organic compounds M1 to M4.

[0035] Figure 6 It is the electrochemical-cyclic voltammetry characteristic curve of organic compound M1 to organic chemical M4.

[0036] Figure 7 These are the thermogravimetric analysis diagrams of organic compounds M1 to M4.

[0037] Figure 8 These are electroluminescence spectra of the optoelectronic devices in device examples 5 to 8.

[0038] The reference numerals are as follows:

[0039] 10: Photoelectric device, 101: anode, 102: cathode, 103: functional layer, 1031: light-emitting layer, 1032: hole functional layer, 1033: electron functional layer, 10321: hole injection layer, 10322: electron blocking layer, 10323: hole transport layer, 10331: electron transport layer, 10332: electron injection layer. DETAILED DESCRIPTION

[0040] The technical solutions in the embodiments of the present application will be described clearly and completely below in conjunction with the drawings in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, rather than all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present application.

[0041] Unless otherwise defined, all professional and scientific terms used herein have the same meanings as those familiar to those skilled in the art. In addition, any methods and materials similar or equivalent to those described herein may be applied to the present invention. The preferred implementation methods and materials described herein are for demonstration purposes only and are not intended to limit the content of this application.

[0042] It should be noted that the description order of the following embodiments is not intended to limit the preferred order of the embodiments. The 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 simplicity and should not be understood as a rigid limitation on the scope of the present invention; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single values ​​within the 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., as well as single numbers within the range, such as 1, 2, 3, 4, 5 and 6, which apply regardless of the range. In addition, whenever a numerical range is indicated in this article, it is meant to include any cited numbers (fractions or integers) within the indicated range.

[0043] In this application, unless otherwise stated, directional words such as "upper" and "lower" generally refer to the upper and lower parts of the optoelectronic device in actual use or working state, specifically the drawing direction in the attached drawings; while "inner" and "outer" refer to the outline of the optoelectronic device. The terms first, second, third, etc. are used only as labels and do not impose numerical requirements or establish a sequence.

[0044] In the present application, “layer A is formed on one side of layer B”, “layer A is formed on the side of layer B away from layer C” or similar descriptions can be expressed as layer A is directly formed on one side of layer B or on the side of layer B away from layer C, that is, layer A is in direct contact with layer B, or as layer A is indirectly formed on one side of layer B or on the side of layer B away from layer C, that is, other spacing structure layers can be formed between layer A and layer B. Similarly, “layer A is arranged on one side of layer B”, “layer A is arranged on the side of layer B away from layer C” can be expressed as layer A is in direct contact with layer B, or as other spacing structure layers are arranged between layer A and layer B; “layer A is arranged between layer B and layer C” can be expressed as layer A is in direct contact with layer B and layer A is in direct contact with layer C, or layer A is in direct contact with layer B and one or more spacing structure layers are arranged between layer A and layer C, or one or more spacing structure layers are arranged between layer A and layer B and one or more spacing structure layers are arranged between layer A and layer C, or one or more spacing structure layers are arranged between layer A and layer B and layer A is in direct contact with layer C.

[0045] The term "including" means "including but not limited to".

[0046] The term "and / or" is used to describe the association relationship of associated objects, indicating that there may be three relationships. 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.

[0047] The term "at least one" refers to one or more, and "more than one" refers to two or more. The term "at least one", "the following at least one" or similar expressions refer to any combination of these items, including any combination of a single or multiple. For example, "at least one of a, b or c" or "at least one of a, b and c" can be expressed as: a, b, c, ab (i.e. a and b), ac, bc or abc, where a, b and c can be single or multiple, respectively.

[0048] The term "alkyl" refers to an aliphatic straight chain alkyl, an aliphatic branched chain alkyl or an aliphatic cyclic alkyl. "C1-C30 alkyl" may be, for example, a straight chain alkyl having 1 to 30 carbon atoms, a branched chain alkyl having 3 to 30 carbon atoms, or a cyclic alkyl having 3 to 30 carbon atoms. The number of carbon atoms in the alkyl group can be, for example, 1 to 3, 1 to 5, 1 to 8, 1 to 10, 1 to 20, 2 to 5, 2 to 10, 3 to 6, 3 to 10, 4 to 8, 4 to 10, 8 to 20, 8 to 30, or 15 to 30, exemplified by 1, 2, 5, 8, 10, 20, 30 or a value between any two of the foregoing numbers, and can be a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, a C6 alkyl group, a C7 alkyl group, a C8 alkyl group, a C9 alkyl group or a C10 alkyl group. Suitable examples of “alkyl” include, but are not limited to, 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-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, or n-triacontyl.

[0049] The term "alkoxy" refers to a group of the general formula *-O-alkyl, where * represents the site of attachment and O represents an oxygen atom. Suitable examples of "alkoxy" include, but are not limited to, methoxy (-O-CH 3 or -OMe), ethoxy (-O-CH 2 CH 3 or -OEt), tert-butyloxy (-OC(CH 3 )3 or -OtBu), n-hexyloxy (-OC 6 H 13 ), n-decyloxy (-OC 10 H 21 ), or n-dodecyloxy (-OC 12 H 25 ).

[0050] The term "aryl" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For a polycyclic ring, at least one is an aromatic ring system. "Aryl having 6 to 30 ring atoms" can be an aromatic group having 6 to 20 ring atoms, an aromatic group having 6 to 18 ring atoms, an aromatic group having 6 to 16 ring atoms, an aromatic group having 6 to 14 ring atoms, or an aromatic group having 6 to 10 ring atoms, and the number of ring atoms can be, for example, 6, 10, 12, 14, 16, 18, 20, 24, 26, 28, 30 or a value between any two of the foregoing values. Suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylenyl, naphthylene, fluorenyl, perylene, acenaphthene and derivatives thereof. It is understandable that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0051] The term "heteroaryl" means that at least one carbon atom on the basis of an aryl group is replaced by a non-carbon atom, and the non-carbon atom may be one or more of an N atom, an O atom, an S atom, an Si atom and a P atom, and the number of heteroatoms is, for example, 1 to 20. "Heteroaryl having 5 to 30 ring atoms" may be a heteroaryl having 5 to 20 ring atoms, a heteroaryl having 5 to 18 ring atoms, a heteroaryl having 5 to 16 ring atoms, a heteroaryl having 5 to 14 ring atoms, a heteroaryl having 5 to 12 ring atoms, or a heteroaryl having 5 to 10 ring atoms, and the number of ring atoms may be, for example, 5, 10, 12, 14, 18, 20, 24, 26, 28, 30 or a value between any two of the foregoing values. Suitable examples include, but are not limited to, thienyl, furanyl, pyrrolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furanofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primidyl, quinazolinonyl, dibenzothienyl, dibenzofuranyl, or carbazolyl.

[0052] In the present application, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring. Medium R 3 It can be connected to any substitutable site in the left benzene ring. Similarly, R 4 It can be connected to any substitutable position of the right benzene ring. Further, in the present application, when the same substituent appears multiple times, it can be independently selected from different groups; for example, the above general formula can contain n2 R 3 , then each R 3 Can be independently selected from different groups. In addition, * represents the connection site, the group shown in the general formula above (R 1 Any connectable sites on the two benzene rings in the main skeleton structure ( The carbon atoms in the ring are connected.

[0053] In the present application, "halogen group" or "halogen" represents -Cl, -Br, -F or -I; hydroxyl represents -OH; carboxyl represents -COOH; nitro represents -NO 2 ; Sulfonic acid group represents -SO 3 H; mercapto represents -SH; cyano represents *-C≡N.

[0054] The terms "combination thereof", "any combination thereof", "any combination thereof" and the like used in this application include all suitable combinations of any two or more of the listed items.

[0055] In this application, "electron donating group" refers to 1 After replacing the hydrogen on the benzene ring, the electron cloud density on the benzene ring increases.

[0056] The present application provides an organic compound having a structure shown in the following general formula (I):

[0057]

[0058] In the general formula (I), Ar 1 and Ar 2 Each of the amines is independently selected from an aromatic ring having 6 to 30 ring atoms, for example, 6, 10, 12, 14, 16, 18, 20, 22, 24, 26, 28 or 30 ring atoms.

[0059] R 1 Selected from electron donating groups, R 2 is selected from an aryl group having 6 to 30 ring atoms which is unsubstituted or substituted by at least one substituent, and a heteroaryl group having 5 to 30 ring atoms which is unsubstituted or substituted by at least one substituent. The substituents are each independently selected from -D, a halogen group, -OH, -NH 2 , -SH, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C1-C30 alkoxy, C1-C30 alkoxycarbonyl, C1-C30 alkylacyloxy, or a combination of these groups. 2 The number of ring atoms is, for example, 6, 10, 12, 14 or a value between any two of the foregoing values, R 2 An example is naphthyl.

[0060] In some embodiments of the present application, R 2 is selected from phenyl or substituted phenyl, naphthyl or substituted naphthyl, wherein each occurrence of the substituent is independently selected from -D, a halogen group, -OH, -NH 2 , -SH, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C1-C10 alkoxy, or a combination of these groups.

[0061] In some embodiments of the present application, the organic compound has a structure shown in the following formula (II):

[0062]

[0063] The organic compounds in the examples of this application are The ring is the core structure. The ring has a larger T1 and T2 energy level difference and a smaller S1 and T2 energy level difference, and the organic compound contains an electron-donating group, which can effectively utilize high-energy triplet excitons, activate the reverse intersystem crossing channel, break through the 25% exciton utilization limit of traditional organic fluorescent materials, and make the exciton utilization rate reach 100%; in addition, compared with the anthracene ring, The ring has a bluer light color, better color purity, and a bluer spectrum, so that the organic compound has more reverse intersystem crossing channels, which is more conducive to the preparation of high-efficiency, high-color purity blue light organic light-emitting diodes.

[0064] In some embodiments of the present application, R 1 and R 2 The same or different. 1 and R 2 When they are different, the organic compound has an asymmetric structure, so that the twisting between the donor and the acceptor and the π bridge can inhibit molecular aggregation, reduce exciton quenching, and is conducive to achieving high efficiency.

[0065] In order to further improve the antisystem crossing of the triplet exciton to the singlet state of the organic compound, in some embodiments of the present application, R 1 A group selected from the group represented by the following formula (1-1) or formula (1-2):

[0066]

[0067] In formula (1-1), X is selected from NR 5 , R 5 is selected from -H, -D, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C1-C30 alkoxy, 6-30 aryl, 5-30 heteroaryl, or a combination of these groups. When the organic compound is used as a light-emitting material of an organic light-emitting diode, in order to further promote the electron-hole transport balance in the light-emitting layer, thereby further improving the device efficiency and performance stability of the organic light-emitting diode, in some embodiments of the present application, R 5 Selected from -H, -D, C1-C10 alkyl or phenyl.

[0068] In formula (1-2), Y-* is selected from N-* or NR 6 -*, R 6is selected from C1-C30 alkylene, C2-C30 alkenylene, C2-C30 alkynylene, C1-C30 alkyleneoxy, 6-30 arylene, 5-30 heteroarylene, or a combination of these groups. When the organic compound is used as a light-emitting material of an organic light-emitting diode, in order to further promote the electron-hole transport balance in the light-emitting layer, thereby further improving the device efficiency and performance stability of the organic light-emitting diode, in some embodiments of the present application, R 6 Selected from C1-C10 alkylene or phenylene.

[0069] In formula (1-1) and formula (1-2), R 3 and R 4 Each occurrence is independently selected from -H, -D, -OH, -NH 2 、-SH、-NR 7 R 8 , C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C1-C30 alkoxy, or a combination of these groups; R 7 and R 8 Each of the following is independently selected from -H, -D, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C1-C30 alkoxy, 6-30 aryl, 5-30 heteroaryl, or a combination of these groups. 3 and R 4 Not connected, or adjacent R 3 and R 4 When the organic compound is used as a light-emitting material of an organic light-emitting diode, in order to further promote the electron-hole transfer balance in the light-emitting layer, thereby further improving the device efficiency and performance stability of the organic light-emitting diode, in some embodiments of the present application, R 3 and R 4 Each occurrence is independently selected from -H, -D or C1-C10 alkyl.

[0070] In formula (1-1) and formula (1-2), n1 and n2 are each independently selected from integers of 0 to 5, and n1 and n2 are each independently selected from 0, 1, 2, 3, 4 or 5, for example.

[0071] In order to further improve the electron mobility of the organic compound, in some embodiments of the present application, R 1 Select from any of the following groups:

[0072]

[0073] Among them, R 7 and R8 are independently selected from C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C1-C10 alkoxy or a combination of these groups; optionally, R 7 and R 8 Each is independently selected from methyl, ethyl, propyl, butyl, pentyl, methoxy, ethoxy, vinyl or ethynyl.

[0074] In some embodiments of the present application, the organic compound has a structure shown in any of the following structural formulas:

[0075]

[0076]

[0077] The present application also provides a method for preparing an organic compound, which can be used to prepare an organic compound having a structure shown in the general formula (I) above, such as Figure 1 As shown, the preparation method of the organic compound comprises the following steps:

[0078] (A1) The general formula is R 1 -X 1 The first compound and diboric acid pinacol ester are mixed to perform a first reaction to obtain a second compound;

[0079] (A2) The general formula is R 2 -X 2 The third compound and diboric acid pinacol ester are mixed to carry out a second reaction to obtain a fourth compound;

[0080] (A3) mixing the fourth compound and the fifth compound to perform a third reaction to obtain a sixth compound;

[0081] (A4) The second compound and the sixth compound are mixed to carry out a fourth reaction to obtain an organic compound having a structure represented by the general formula (I).

[0082] Wherein, in the first compound and the second compound, X 1 and X 2 are independently selected from F, Cl, Br or I.

[0083] The second compound has the structure shown in the following formula (II):

[0084]

[0085] In formula (II), R 1 The selection range is described above.

[0086] The fourth compound has the structure shown in the following formula (III):

[0087]

[0088] In formula (III), R 2 The selection range is described above.

[0089] The fifth compound has the structure shown in the following formula (IV):

[0090]

[0091] In formula (IV), X 3 and X 4 are independently selected from F, Cl, Br or I.

[0092] The sixth compound has a structure represented by the following general formula (V):

[0093]

[0094] In formula (V), X 3 and R 2 The selection ranges are described above.

[0095] In order to further improve the yield and purity of the second compound, in some embodiments of the present application, step (A1) includes: reacting a first reaction system comprising the first compound, bipyrazone, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium and potassium acetate under an atmosphere of a first inert gas to generate the second compound. Wherein, the molar ratio of the first compound to bipyrazone is 1:(1-1.2), for example, it can be 1:1, 1:1.1, 1:1.2 or a value between any two of the above values; and / or, the temperature of the first reaction is 80°C to 90°C, for example, it can be 80°C, 85°C, 90°C or a value between any two of the above values; and / or, the time of the first reaction is 11h to 13h, for example, it can be 11h, 12h, 13h or a value between any two of the above values. Optionally, the solvent of the first reaction system is 1,4-dioxane, and / or the first inert gas is selected from one or more of nitrogen, argon, helium, neon, krypton and xenon. It should be noted that [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride is used as a catalyst, and potassium acetate provides an alkaline environment.

[0096] In order to further improve the yield and purity of the fourth compound, in some embodiments of the present application, step (A2) includes: in the atmosphere of a second inert gas, reacting a second reaction system comprising a third compound, bipyraclostrobin, [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride and potassium acetate to generate the fourth compound. Wherein, the molar ratio of the third compound to bipyraclostrobin is 1:(1-1.2), for example, it can be 1:1, 1:1.1, 1:1.2 or a value between any two of the above values; and / or, the temperature of the second reaction is 80°C to 90°C, for example, it can be 80°C, 85°C, 90°C or a value between any two of the above values; and / or, the time of the second reaction is 11h to 13h, for example, it can be 11h, 12h, 13h or a value between any two of the above values. Optionally, the solvent of the second reaction system is 1,4-dioxane, and / or the second inert gas is selected from one or more of nitrogen, argon, helium, neon, krypton and xenon.

[0097] In order to further improve the yield and purity of the sixth compound, in some embodiments of the present application, step (A3) comprises: in the atmosphere of a third inert gas, reacting a third reaction system comprising a fourth compound, a fifth compound, tetrakis(triphenylphosphine)palladium, tetrabutylammonium halide and potassium carbonate to generate the sixth compound, wherein tetrakis(triphenylphosphine)palladium and potassium carbonate are used as catalysts, and the role of tetrabutylammonium halide is: a phase transfer agent, which can allow the organic phase and the aqueous phase to contact better. The molar ratio of the fourth compound to the fifth compound is 1: (1-1.2), for example, it can be 1: 1, 1: 1.1, 1: 1.2 or a value between any two of the above values; and / or, the temperature of the third reaction is 80°C-90°C, for example, it can be 80°C, 85°C, 90°C or a value between any two of the above values; and / or, the time of the third reaction is 11h-13h, for example, it can be 11h, 12h, 13h or a value between any two of the above values. Optionally, the solvent of the third reaction system is toluene, and / or the tetrabutylammonium halide is tetrabutylammonium bromide, and / or the third inert gas is selected from one or more of nitrogen, argon, helium, neon, krypton and xenon.

[0098] In order to further improve the yield and purity of the organic compound of the structure shown in the general formula (I), in some embodiments of the present application, step (A4) includes: in the atmosphere of a fourth inert gas, reacting a fourth reaction system comprising a second compound, a sixth compound, tetrakis(triphenylphosphine)palladium, tetrabutylammonium halide and potassium carbonate to generate an organic compound of the structure shown in the general formula (I). Wherein, the molar ratio of the second compound to the sixth compound is 1:(1-1.2), for example, it can be 1:1, 1:1.1, 1:1.2 or a value between any two of the above values; and / or, the temperature of the fourth reaction is 80°C-90°C, for example, it can be 80°C, 85°C, 90°C or a value between any two of the above values; and / or, the time of the fourth reaction is 11h-13h, for example, it can be 11h, 12h, 13h or a value between any two of the above values. Optionally, the solvent of the fourth reaction system is toluene, and / or the tetrabutylammonium halide is tetrabutylammonium bromide, and / or the fourth inert gas is selected from one or more of nitrogen, argon, helium, neon, krypton and xenon.

[0099] It should be noted that the organic compound represented by the general formula (I) is not limited to the one prepared by the method for preparing the organic compound provided in the present application. In addition, in steps (A1) to (A4), in order to further improve the purity of the product, the product generated by the reaction may be further separated and purified, and the separation and purification treatment includes but is not limited to one or more of extraction, drying and column chromatography.

[0100] In some embodiments of the present application, the fifth compound has a structure shown in the following formula (VI):

[0101]

[0102] In some embodiments of the present application, the sixth compound has a structure shown in the following formula (VII):

[0103]

[0104] An embodiment of the present application also provides a composition, which includes any one of the organic compounds described above.

[0105] In some embodiments of the present application, the composition further comprises at least one organic functional material, and the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials or light-emitting materials.

[0106] Among them, hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials and organic dyes can all be selected from conventional materials in the art, wherein the luminescent materials include but are not limited to one or more of singlet luminophores (fluorescent luminophores), triplet luminophores (phosphorescent luminophores) and organic thermally excited delayed fluorescent materials (TADF materials). Various organic functional materials are described in detail in patent documents WO2010135519A1, US20090134784A1 and WO2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0107] In some embodiments of the present application, the organic functional material is selected from organic light-emitting guest materials, such as organic blue light guest materials. The organic blue light guest material can be a common blue light dopant in the art.

[0108] In some embodiments of the present application, the composition further comprises at least one first organic solvent. The composition may be a solution or a suspension. Further, the composition may be an ink, and the first organic solvent may be a solvent having a Hansen solubility parameter within the following range:

[0109] δd (dispersion force) is in the range of 17.0 to 23.2 MPa1 / 2, especially in the range of 18.5 to 21.0 MPa1 / 2;

[0110] δp (polar force) is in the range of 0.2 to 12.5 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2;

[0111] δh (hydrogen bonding force) is in the range of 0.9 to 14.2 MPa1 / 2, and particularly in the range of 2.0 to 6.0 MPa1 / 2.

[0112] According to the composition of the present application, the first organic solvent needs to consider its boiling point parameter when selecting. In some embodiments of the present application, the boiling point of the first organic solvent is not less than 150°C, for example, not less than 180°C, not less than 200°C, not less than 250°C, not less than 275°C or not less than 300°C, which is beneficial to prevent the "nozzle clogging" problem of the inkjet print head and improve the film quality.

[0113] When the composition is used in a printing process, the viscosity and surface tension of the composition are important parameters. The surface tension parameters of a suitable composition are suitable for a specific substrate and a specific printing method. In some embodiments, the surface tension of the composition according to the embodiment of the present application at operating temperature or at 25°C ranges from 19dyne / cm to 50dyne / cm, for example, 22dyne / cm to 35dyne / cm, and for example, 25dyne / cm to 33dyne / cm. In some embodiments, the viscosity of the composition according to the embodiment of the present application at operating temperature or at 25°C ranges from 1cps to 100cps, for example, 1cps to 50cps, and for example, 1.5cps to 20cps, and for example, 4.0cps to 20cps. The composition so formulated will be beneficial to inkjet printing.

[0114] In some embodiments of the present application, the weight ratio of the organic compound in the composition is 0.3wt% to 30wt%, for example, 0.5wt% to 20wt%, 0.5wt% to 15wt%, 0.5wt% to 10wt% or 1wt% to 5wt%.

[0115] In some embodiments of the present application, the first organic solvent is selected from at least one of aromatic or heteroaromatic-based solvents, ester-based solvents, aromatic ketone-based solvents, aromatic ether-based solvents, aliphatic ketones, aliphatic ethers, alicyclic compounds, olefin compounds, borate ester compounds and phosphate ester compounds.

[0116] The aromatic or heteroaromatic solvent may be selected from, but not limited to, p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, di ... At least one of propylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate and ethyl 2-furoate.

[0117] The ester-based solvent may be selected from, but not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Preferably, the ester-based solvent may be selected from one or more of octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate.

[0118] The aromatic ketone-based solvent may be selected from, but not limited to, 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and derivatives of the above solvents. As an example, the derivative may be selected from, but not limited to, one or more of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, and 2-methylpropiophenone.

[0119] The aromatic ether-based solvent may be selected from, but is not limited to, one or more of 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether.

[0120] The aliphatic ketone-based solvent can be selected from, but is not limited to, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, one or more of amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether and tetraethylene glycol dimethyl ether.

[0121] In some embodiments of the present application, the composition may further include a second organic solvent, which may be selected from but not limited to methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin and one or more of indene.

[0122] It is understood that when the composition is a solution or a suspension, the composition may further include one or more additives, including but not limited to one or more of surfactants, lubricants, wetting agents, dispersants, hydrophobic agents and adhesives.

[0123] In some embodiments of the present application, when the composition includes one or more first organic solvents, the mass of the organic compound of the structure represented by the general formula (I) accounts for 0.01% to 10% of the total mass of the composition, for example, it can be 0.01%, 0.05%, 0.1%, 0.2%, 0.25%, 0.5%, 0.8%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10% or a value between any two of the foregoing values.

[0124] In some embodiments of the present application, when the composition includes one or more organic functional materials, in the composition, the mass ratio of the organic compound to the organic functional material is 1:99 to 30:70.

[0125] An embodiment of the present application also provides an optoelectronic device, which includes but is not limited to an organic light emitting diode, an organic photovoltaic cell, an organic light emitting cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor or an organic plasmon emission diode.

[0126] like Figure 2 and Figure 3 As shown, the photoelectric device 10 includes an anode 101, a plurality of functional layers and a cathode 102 which are stacked in sequence, wherein the anode 101 and the cathode 102 are arranged opposite to each other, and the plurality of functional layers are arranged between the anode 101 and the cathode 102. The material of at least one of the plurality of functional layers includes an organic compound having a structure shown in general formula (I), or an organic compound prepared by any one of the preparation methods described above, or at least one of the plurality of functional layers is prepared by using a composition as described above, so as to improve the device efficiency and performance stability of the photoelectric device 10.

[0127] In some embodiments of the present application, the multiple functional layers include a light-emitting layer 1031, and the material of the light-emitting layer 1031 includes an organic compound with a structure shown in general formula (I), or an organic compound prepared by any of the preparation methods described in the foregoing text, or the light-emitting layer 1031 is prepared using a composition as described in any of the foregoing text, which can improve the carrier mobility of the light-emitting layer 1031, promote the electron-hole transfer balance, achieve blue light emission, and improve the device efficiency, performance stability and luminescence purity of the optoelectronic device 10.

[0128] In some embodiments of the present application, the plurality of functional layers include a hole functional layer 1032, see Figure 2 and Figure 3 The hole function layer 1032 is disposed between the anode 101 and the light emitting layer 1031. The hole function layer 1032 may be a single layer structure or a multi-layer structure, and the thickness of the hole function layer 1032 is, for example, 10 nm to 100 nm.

[0129] When the hole functional layer 1032 is a multi-layer structure, the hole functional layer 1032, for example, includes one or more of a hole injection layer, a hole transport layer and an electron blocking layer. For the hole functional layer 1032 including the hole injection layer, the hole transport layer and the electron blocking layer, the hole transport layer is located between the hole injection layer and the electron blocking layer, and the hole injection layer is closer to the anode 101 than the electron blocking layer; for the hole functional layer 1032 including the hole transport layer and the electron blocking layer, the hole transport layer is closer to the anode 101 than the electron blocking layer; for the hole functional layer 1032 including the hole injection layer and the hole transport layer, the hole injection layer is closer to the anode 101 than the hole transport layer.

[0130] The hole injection layer is a layer used to promote the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that can skillfully receive holes injected from the positive electrode at a low voltage. The highest occupied molecular orbital (HOMO) of the hole injection material is, for example, between the work function of the anode material and the HOMO of the surrounding organic material layer. In principle, all materials that can be used as hole injection layers of organic light-emitting diodes may be used as hole injection materials for the optoelectronic device in this application. Non-limiting examples of hole injection materials include one or more of NDP-2 (manufactured by Novaled), NDP-9 (manufactured by Novaled), F4-TCNQ, and F6-TCNNQ as p-type doping materials; tetrafluorotetracyanoquinodimethane, 7,7,8,8-tetracyanoquinodimethane, 4,4',4"-tris(2-naphthylphenylamino)triphenylamine (m-MTDATA), perylenetetracarboxylic dianhydride, pentacene, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), PEDOT, PEDOT:PSS, PEDOT:PSS doped with s-MoO 3 Derivatives (PEDOT:PSS:s-MoO 3 ), 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, tetracyanoquinodimethane (F4-TCQN), copper phthalocyanine, copper hexadecafluorophthalocyanine, nickel oxide, molybdenum oxide, tungsten oxide, vanadium oxide, molybdenum sulfide, tungsten sulfide and copper oxide.

[0131] The hole transport layer can be used to smoothly transport holes. The hole transport material known in the art for the hole transport layer is suitably a material with a high hole mobility, which can receive holes transmitted from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Non-limiting examples of hole transport materials are organic materials based on arylamines, organic materials based on carbazoles, conductive polymers, or block copolymers having both conjugated and non-conjugated parts. In principle, all materials that can be used as hole transport layers of organic light-emitting diodes may be used as hole transport materials for optoelectronic devices in this application.Non-limiting examples of hole transport materials include polyaniline (CAS No. 25233-30-1), polypyrrole (CAS No. 30604-81-0), 3-hexyl substituted polythiophene (CAS No. 104934-50-1), poly(9-vinylcarbazole) (abbreviated as PVK, CAS No. 25067-59-8), 4,4'-bis(9-carbazole)biphenyl (abbreviated as CBP, CAS No. 58328-31-7), poly[bis(4-phenyl)(4-butylphenyl)amine], 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (abbreviated as TAPC, CAS No. 58473-78-2), poly[(9,9-dioctylfluorene 9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)] (abbreviated as TFB, CAS No. 220797-16-0), poly[(N,N'-(4-n-butylphenyl)-N,N'-diphenyl-1,4-phenylenediamine)-ALT-(9,9-dioctylfluorenyl-2,7-diyl)] (CAS No. 223569-31-1), 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (CAS No. 124729-98-2), 4,4',4"-tris(carbazol-9-yl)triphenylamine (abbreviated as TCTA, CAS No. 139092-78-7), 4,4' ,4'-Tris(2-naphthylphenylamino)triphenylamine (CAS No. 185690-41-9), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (abbreviated as NPB, CAS No. 123847-85-8), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (abbreviated as TPD, CAS No. 65181-78-4), N,N'-bis[4-(diphenylamino)phenyl]-N,N'-diphenylbenzidine (CAS No. 209980-53-0), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-9 ,9-spirobifluorene-2,7-diamine (referred to as Spiro-TPD, CAS No. 1033035-83-4), N2,N7-di-1-naphthyl-N2,N7-diphenyl-9,9'-spirobi[9H-fluorene]-2,7-diamine (CAS No. 932739-76-9), poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (referred to as PTTA, CAS No. 1333317-99-9) and 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene (referred to as Spiro-omeTAD, CAS No. 207739-72-8) One or more of them.

[0132] The electron blocking layer is used to block the transfer of excitons and electrons to the hole transport layer and / or the hole injection layer. In principle, all materials that can be used as electron blocking layers of organic light-emitting diodes may be used as electron blocking materials for optoelectronic devices in this application. Electron blocking materials include, but are not limited to, TCTA.

[0133] In some embodiments of the present application, the plurality of functional layers include an electronic functional layer 1033, as described below. Figure 2 and Figure 3 As shown, the electronic functional layer 1033 is disposed between the light-emitting layer 1031 and the cathode 102. The electronic functional layer 1033 may be a single-layer structure or a multi-layer structure, and the thickness of the electronic functional layer 1033 is, for example, 10 nm to 100 nm. When the electronic functional layer 1033 is a multi-layer structure, the electronic functional layer 1033, for example, includes one or more of an electron injection layer, an electron transport layer, and a hole blocking layer. For the electronic functional layer 1033 including the electron injection layer, the electron transport layer, and the hole blocking layer, the electron transport layer is located between the electron injection layer and the hole blocking layer, and the electron injection layer is closer to the cathode 102 than the hole blocking layer; for the electronic functional layer 1033 including the electron transport layer and the hole blocking layer, the electron transport layer is closer to the cathode 102 than the hole blocking layer; for the electronic functional layer 1033 including the electron injection layer and the electron transport layer, the electron injection layer is closer to the cathode 102 than the electron transport layer. It should be noted that when the electronic functional layer 1033 includes multiple materials and has a multi-layer structure, the multiple materials may all be in the same layer, or respectively in different layers, or partially in the same layer.

[0134] The electron transport layer can be used to smoothly transport electrons. The electron transport material can be a material with high electron mobility, which can skillfully receive electrons injected from the cathode 102 and transfer the electrons to the light-emitting layer 1031. Non-limiting examples of electron transport materials are one or more of an Al complex of 8-hydroxyquinoline, a complex comprising Alq3, an organic free radical compound, a hydroxyflavone-metal complex, 8-hydroxyquinoline lithium (LiQ), or a benzimidazole-based compound. In principle, all materials that can be used as an electron transport layer of an organic light-emitting diode may be used as an electron transport material for an optoelectronic device in the present application. The electron transport material is selected from one or more of an inorganic electron transport material and an organic electron transport material.

[0135] The inorganic electron transport material includes but is not limited to one or more of doped metal oxide particles, undoped metal oxide particles, ceramic semiconductor materials, IIB-VIA semiconductor materials, IIIA-VA semiconductor materials and IB-IIIA-VIA semiconductor materials. The metal oxide in the undoped metal oxide particles includes but is not limited to ZnO, TiO 2SnO 2 、ZrO 2 、 2 O 5 The metal oxides in the doped metal oxides include but are not limited to ZnO, TiO 2 SnO 2 、ZrO 2 、 2 O 5 、Al 2 O 3 One or more of the doped metal oxides, the doping elements in the doped metal oxides include but are not limited to one or more of Al, Mg, Li, Mn, Y, La, Cu, Ni, Zr, Ce, In, Ga, Sn, as examples, the doped metal oxides may be aluminum zinc oxide (AZO), lithium-doped zinc oxide (LZO), magnesium-doped zinc oxide (MZO), tin-doped zinc oxide (Sn-ZnO), etc. The ceramic semiconductor materials include but are not limited to barium titanate. The IIB-VIA semiconductor materials include but are not limited to one or more of ZnS, ZnSe, and CdS. The IIIA-VA semiconductor materials include but are not limited to one or more of InP and GaP. The IB-IIIA-VIA semiconductor materials include but are not limited to one or more of CuInS and CuGaS.

[0136] Non-limiting examples of organic electron transport materials are NET-164 (manufactured by Novaled), NDN-87 (manufactured by Novaled), NDN-45 (manufactured by Novaled), NDN-18 (manufactured by Novaled), NDN-218 (manufactured by Novaled), ET093 (manufactured by Idemitsu Kosan), ETM020 (manufactured by Merck), ETM033 (manufactured by Merck), ETM034 (manufactured by Merck), ETM036 (manufactured by Merck), 4,6-bis(3,5-di(pyridin-3-yl)phenyl)-2-methylpyrimidine, 2,9-dimethyl-4,7-biphenyl-1,10-o-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, 1,3,5-tri(1-phenyl-1H-benzimidazol-2-yl)benzene, 8-hydroxyquinoline aluminum, 8-hydroxyquinoline lithium, bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum or more.

[0137] The electron injection layer can be used to smoothly inject electrons. The electron injection material is preferably: having the ability to transport electrons, having the effect of injecting electrons from the negative electrode, and having an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, preventing the excitons generated by the light-emitting layer from moving to the hole injection layer, and also having an excellent ability to form a thin film. Non-limiting examples of electron injection materials are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenyl methane, anthrone, etc. and one or more of their derivatives, metal complex compounds, or nitrogen-containing 5-membered ring derivatives. In principle, all materials that can be used as electron injection layers of organic light-emitting diodes may be used as electron injection materials for optoelectronic devices in this application. Non-limiting examples of electron injection materials are Yb (ytterbium), yttrium fluoride, Li, LiF, NaF, CsCO 3 , Cs and KBH 4 One or more of .

[0138] The hole blocking layer is a layer that blocks holes from reaching the cathode, and non-limiting examples of the hole blocking material are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, or aluminum complexes.

[0139] In the optoelectronic device 10 of the embodiment of the present application, the anode 101 is an electrode for injecting holes, and the anode 101 can easily inject holes into the hole injection layer, or the hole transport layer, or the light-emitting layer. The anode 101 may include one or more of a conductive metal, a conductive metal oxide, or a conductive polymer. In at least one embodiment of the present application, the absolute value of the difference between the work function of the anode 101 and the HOMO energy level or valence band energy level of the luminophore in the light-emitting layer 1031 is less than 0.5 eV, or the absolute value of the difference between the work function of the anode 101 and the HOMO energy level or valence band energy level of the P-type semiconductor material in the hole functional layer (one or more of the hole injection layer, the hole transport layer, or the electron blocking layer) is less than 0.5 eV. Non-limiting examples of the material of the anode 101 are Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, or aluminum-doped zinc oxide (AZO).

[0140] The cathode 102 is an electrode for injecting electrons, and the cathode 102 can easily inject electrons into the electron injection layer, or the electron transport layer, or the light-emitting layer 1031. The cathode 102 may include one or more of a conductive metal, a conductive metal oxide, or a conductive polymer. In at least one embodiment of the present application, the absolute value of the difference between the work function of the cathode 102 and the LUMO energy level or the conduction band energy level of the luminophore in the light-emitting layer 1031 is less than 0.5 eV, or the absolute value of the difference between the work function of the cathode 102 and the LUMO energy level or the conduction band energy level of the N-type semiconductor material in the electron functional layer (one or more of the electron injection layer, the electron transport layer, or the hole blocking layer) is less than 0.5 eV. Non-limiting examples of cathode 102 materials are Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, or ITO.

[0141] It can be understood that the optoelectronic device 10 may also include a substrate, which is arranged on the side of the anode 101 away from the multiple functional layers or the side of the cathode 102 away from the multiple functional layers. The substrate can be a rigid substrate or a flexible substrate. The material of the rigid substrate includes but is not limited to one or more of glass, ceramic and silicon wafer, and the material of the flexible substrate includes but is not limited to one or more of polyimide, polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate and polyether sulfone.

[0142] It should be noted that the preparation methods of each functional layer in the optoelectronic device 10 include but are not limited to chemical methods and / or physical methods. Among them, the chemical method includes but is not limited to one or more of chemical vapor deposition, continuous ion layer adsorption and reaction, anodization, electrolytic deposition and coprecipitation. The physical method includes but is not limited to physical plating and solution method. The physical plating method includes but is not limited to one or more of thermal evaporation coating, electron beam evaporation coating, magnetron sputtering, multi-arc ion plating, physical vapor deposition, atomic layer deposition and pulsed laser deposition. The solution method includes but is not limited to spin coating, printing, inkjet printing, scraping, printing, dip pulling, immersion, spraying, rolling, casting, slit coating and strip coating. After the preparation of each functional layer of the optoelectronic device, a packaging process is required. The packaging process can be carried out by commonly used machine packaging or manual packaging. In the packaging process environment, the oxygen content and water content are both lower than 0.1ppm to ensure the stability of the optoelectronic device. Specifically, the packaging material used to form the packaging layer is selected from one or more of ultraviolet glue, metal film and glass glue. As an example, the packaging material is acrylic resin or epoxy resin.

[0143] Taking the preparation of the light-emitting layer by the solution method as an example, the preparation method of the light-emitting layer includes the steps of: depositing a solution containing an organic compound represented by the general formula (I), and then drying to solidify into a film to obtain the light-emitting layer. The deposition method includes but is not limited to one or more of spin coating, printing, inkjet printing, blade coating, printing, dip-coating, immersion, spraying, roll coating, casting, slit coating and strip coating, and the drying treatment includes but is not limited to one or more of heating and vacuum drying.

[0144] The present application also provides an electronic device, which includes any of the optoelectronic devices described above. The electronic device can be, for example, any electronic product with a display function, including but not limited to a smartphone, a tablet personal computer, a mobile phone, a video phone, an e-book reader, a laptop PC, a netbook computer, a workstation, a server, a personal digital assistant, a portable multimedia player, an MP3 player, a mobile medical machine, a camera, a game console, a digital camera, a car navigation system, an electronic billboard, an ATM, a smart bracelet, a smart watch, a virtual reality (VR) device or a wearable device.

[0145] The technical scheme and technical effects of the present application are described in detail below through specific embodiments, comparative examples and experimental examples. The following embodiments are only some embodiments of the present application and do not specifically limit the present application. It should be noted that the new substances involved in the specific embodiments and comparative examples are identified by combining 1HNMR, 13CNMR, MS and elemental analysis.

[0146] Organic Compound Example 1

[0147] This embodiment provides an organic compound M1 and a preparation method thereof. The synthesis route of the organic compound M1 is as follows:

[0148]

[0149] The preparation method of the organic compound M1 comprises the following steps:

[0150] S1.1. Under the protection of nitrogen atmosphere, add 48.29mmol of 2-bromonaphthalene (CAS No. 580-13-2) and 53.12mmol of biboric acid pinacol ester (CAS No. 78183-34-3) to a 250mL two-necked bottle, then add 100mL of 1,4-dioxane (CAS No. 123-91-1) to the two-necked bottle, stir until completely dissolved, then add 2.41mmol of [1,1'-bis(diphenylphosphino)ferrocene] dichloropalladium (CAS No. 72287-26-4) and 482 .93mmol of potassium acetate, heated to 80°C, stirred for reaction for 12h to obtain a reaction product; deionized water was added to the reaction product, and extracted with dichloromethane several times, the organic phase was collected, and then the organic phase was dried with anhydrous magnesium sulfate, and then the organic phase was distilled under reduced pressure to remove the solvent to obtain a crude product, and then a chromatography column (filler: silica gel) was used to separate and purify the crude product, and the mobile phase was composed of petroleum ether and dichloromethane (the volume ratio of petroleum ether to dichloromethane was 1:1) to obtain a purified product (white solid), the yield of organic compound M1-1 was 93.7%, and the nuclear magnetic resonance data were: 1 H NMR (500MHz, Chloroform-d) δ7.98-7.93(m,1H),7.88-7.81(m,2H),7.77-7.70(m,2H),7.57-7.47(m,2H),1.24(s,12H).

[0151] S1.2. Under the protection of nitrogen atmosphere, add 30.84mmol of 4-bromotriphenylamine (CAS No. 36809-26-4) and 33.93mmol of biboric acid pinacol ester to a 250mL two-necked bottle, then add 100mL of 1,4-dioxane (CAS No. 123-91-1) to the two-necked bottle, stir until completely dissolved, then add 1.54mmol of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride and 308.43mmol of potassium acetate, and heat to 400℃. 80°C, stirred for reaction for 12h to obtain a reaction product; deionized water was added to the reaction product, and extracted with dichloromethane several times, the organic phase was collected, and then the organic phase was dried with anhydrous magnesium sulfate, and then the organic phase was distilled under reduced pressure to remove the solvent to obtain a crude product, and then the crude product was separated and purified by a chromatography column (filler: silica gel), and the mobile phase consisted of petroleum ether and dichloromethane (the volume ratio of petroleum ether to dichloromethane was 1:1), and a purified product (white solid) was obtained. The yield of organic compound M1-2 was 94.31%, and the nuclear magnetic resonance data were: 1H NMR (500MHz, Chloroform-d) δ7.61-7.55(m,2H),7.32-7.25(m,4H),7.13-7.08(m,6H),7.04(m,2H),1.24(s,12H).

[0152] S1.3, under the protection of nitrogen atmosphere, 39.35mmol of compound M1-1 and 43.28mmol of 6,12-dibromo (CAS No. 131222-99-6) was added to a 250 mL two-necked bottle, and then 100 mL of toluene was added to the two-necked bottle, and stirred until completely dissolved. Then, 1.97 mmol of tetrakis(triphenylphosphine)palladium (CAS No. 14221-01-3), 3.93 mmol of tetrabutylammonium bromide (CAS No. 10549-76-5) and 393.49 mmol of potassium carbonate were added thereto, and the temperature was raised to 90°C, and the reaction was stirred for 12 hours to obtain the reaction product. deionized water was added to the reaction product, and the product was extracted with dichloromethane for several times, the organic phase was collected, and then the organic phase was dried with anhydrous magnesium sulfate, and the organic phase was distilled under reduced pressure to remove the solvent to obtain a crude product, and then the crude product was separated and purified by a chromatography column (filler: silica gel), and the mobile phase was composed of petroleum ether and dichloromethane (the volume ratio of petroleum ether to dichloromethane was 1:1), and a purified product (white solid) was obtained. The yield of organic compound M1-3 was 92.07%, and the nuclear magnetic resonance data were: 1 H NMR(500MHz,Chloroform-d)δ8.54(s,1H),8.41(s,1H),8.33(m,1H),8.24(s,1H),8.26-8.21(m,1H ),8.10-8.04(m,1H),8.07-7.96(m,2H),7.94-7.82(m,2H),7.68(m,2.2Hz,1H),7.59-7.47(m,6H).

[0153] S1.4. Under the protection of nitrogen atmosphere, 23.08 mmol of compound M1-2, 25.38 mmol of compound M1-3, 1.15 mmol of tetrakis(triphenylphosphine)palladium, 1.15 mmol of tetrabutylammonium bromide and 230.76 mmol of potassium carbonate were placed in a 250 mL round-bottom flask, and then 100 mL of toluene was added. The mixture was heated to 90° C. under stirring, and the reaction was stirred at 90° C. for 12 h. The reaction was cooled to room temperature to obtain the reaction product. deionized water was added to the reaction product, and the product was extracted with dichloromethane for several times, the organic phase was collected, and then the organic phase was dried with anhydrous magnesium sulfate, and the organic phase was distilled under reduced pressure to remove the solvent to obtain a crude product, and then the crude product was separated and purified by a chromatography column (filler: silica gel), and the mobile phase was composed of petroleum ether and dichloromethane (the volume ratio of petroleum ether to dichloromethane was 1:1), and a purified product (white solid) was obtained, and the yield of the organic compound M1 was 86.99%, and the nuclear magnetic resonance data were: 1 H NMR(500MHz,Chloroform-d)δ8.51(s,1H),8.44(s,1H),8.24(m,1H),8.10-8.03(m,2H),8.03-7.96(m,2H),7.94-7 .86(m,2H),7.89-7.82(m,1H),7.68(m,1H),7.55-7.47(m,8H),7.35-7.28(m,4H),7.22-7.14(m,6H),7.10(m,2H).

[0154] Organic Compound Example 2

[0155] This embodiment provides an organic compound M2 and a preparation method thereof. The synthesis route of the organic compound M2 is as follows:

[0156]

[0157] Compared with the preparation method of organic compound M1, the difference of the preparation method of organic compound M2 is that: the "30.84mmol of 4-bromotriphenylamine" in step S1.2 is replaced by "30.84mmol of 3-bromotriphenylamine (CAS No. 78600-33-6)", and the "43.28mmol of 6,12-dibromotriphenylamine" in step S1.3 is replaced by "43.28mmol of 6,12-dibromotriphenylamine (CAS No. 78600-33-6)". " is replaced by "43.28mmol of 3,9-dibromo (CAS No. 2169233-99-0)", and replace "23.08 mmol of compound M1-2" in step S1.4 with "23.08 mmol of compound M2-2", and replace "25.38 mmol of compound M1-3" in step S1.4 with "25.38 mmol of compound M2-3", and finally obtain white solid M2, the yield of organic compound M2 is 89.89%, and the NMR data is: 1 H NMR(500MHz,Chloroform-d)δ8.51(d,1H),8.38(d,1H),8.22(m,1H),8.16-8.11(m,2H),8.03-7.96(m,2H), 7.94-7.87(m,3H),7.59-7.48(m,9H),7.30-7.26(m,4H),7.23-7.20(m,2H),7.13-7.09(m,4H),7.04(m,2H).

[0158] Organic Compound Example 3

[0159] This embodiment provides an organic compound M3 and a preparation method thereof. The synthesis route of the organic compound M3 is as follows:

[0160]

[0161] The preparation method of the organic compound M1 comprises the following steps:

[0162] S3.1. Under the protection of nitrogen atmosphere, add 48.29mmol of 1-bromonaphthalene (CAS No. 90-11-9) and 53.12mmol of biboric acid pinacol ester (CAS No. 78183-34-3) to a 250mL two-necked bottle, then add 100mL of 1,4-dioxane (CAS No. 123-91-1) to the two-necked bottle, stir until completely dissolved, then add 2.41mmol of [1,1'-bis(diphenylphosphino)ferrocene] dichloropalladium (CAS No. 72287-26-4) and 482 .93mmol of potassium acetate, heated to 90°C, stirred for reaction for 12h to obtain a reaction product; deionized water was added to the reaction product, and extracted with dichloromethane several times, the organic phase was collected, and then the organic phase was dried with anhydrous magnesium sulfate, and then the organic phase was distilled under reduced pressure to remove the solvent to obtain a crude product, and then a chromatography column (filler: silica gel) was used to separate and purify the crude product, and the mobile phase was composed of petroleum ether and dichloromethane (the volume ratio of petroleum ether to dichloromethane was 1:1) to obtain a purified product (white solid), the yield of organic compound M3-1 was 93.7%, and the nuclear magnetic resonance data were: 1H NMR (500MHz, Chloroform-d) δ7.93-7.81(m,3H),7.57(m,1H),7.49(m,1H),7.44-7.35(m,2H),1.24(s,12H).

[0163] S3.2. Under the protection of nitrogen atmosphere, add 27.45mmol of 10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydroacridine (CAS No. 1342892-15-2) and 30.20mmol of diboric acid pinacol ester to a 250mL two-necked bottle, then add 100mL of 1,4-dioxane to the two-necked bottle, stir until completely dissolved, then add 1.37mmol of [1,1'-bis(diphenylphosphino)ferrocene] dichloropalladium and 274.51mmol of potassium acetate. , heating to 90°C, stirring for reaction for 12h to obtain a reaction product; deionized water was added to the reaction product, and dichloromethane was used for extraction several times, the organic phase was collected, and then the organic phase was dried with anhydrous magnesium sulfate, and then the organic phase was distilled under reduced pressure to remove the solvent to obtain a crude product, and then a chromatography column (filler: silica gel) was used to separate and purify the crude product, and the mobile phase was composed of petroleum ether and dichloromethane (the volume ratio of petroleum ether to dichloromethane was 1:1), and a purified product (white solid) was obtained, and the yield of the organic compound M3-2 was 90.33%, and the nuclear magnetic resonance data were: 1 H NMR (500MHz, Chloroform-d) δ7.61-7.57(m,2H),7.29-7.25(m,2H),7.16-7.07(m,6H),6.96(m,2H),1.62(s,6H),1.24(s,12H).

[0164] S3.3, under the protection of nitrogen atmosphere, 39.35mmol of compound M3-1 and 43.28mmol of 6,12-dibromo Add to a 250mL two-necked bottle, then add 100mL of toluene to the two-necked bottle, stir until completely dissolved, then add 1.97mmol of tetrakis(triphenylphosphine)palladium (CAS No. 14221-01-3), 1.973mmol of tetrabutylammonium bromide and 393.49mmol of potassium carbonate, heat to 90°C, stir and react for 12h to obtain a reaction product; add deionized water to the reaction product, extract with dichloromethane several times, collect the organic phase, then dry the organic phase with anhydrous magnesium sulfate, and then distill the organic phase under reduced pressure to remove the solvent to obtain a crude product, then separate and purify the crude product with a chromatography column (filler is silica gel), the mobile phase consists of petroleum ether and dichloromethane (the volume ratio of petroleum ether to dichloromethane is 1:1), and obtain a purified product (white solid), the yield of organic compound M3-3 is 90.31%, and the nuclear magnetic resonance data are: 1 HNMR(500MHz,Chloroform-d)δ8.55-8.47(m,2H),8.31-8.27(m,1H),8.09-7.99(m,3H),7.95-7.88(m,3H),7.63-7.53(m,6H),7.53-7.46(m,2H).

[0165] S3.4. Under the protection of nitrogen atmosphere, 23.08 mmol of compound M3-2, 25.38 mmol of compound M3-3, 1.15 mmol of tetrakis(triphenylphosphine)palladium, 1.15 mmol of tetrabutylammonium bromide and 230.76 mmol of potassium carbonate were placed in a 250 mL round-bottom flask, and then 100 mL of toluene was added. The mixture was heated to 90° C. under stirring, and the reaction was stirred at 90° C. for 12 h. The reaction was cooled to room temperature to obtain the reaction product. deionized water was added to the reaction product, and the product was extracted with dichloromethane for several times, the organic phase was collected, and then the organic phase was dried with anhydrous magnesium sulfate, and the organic phase was distilled under reduced pressure to remove the solvent to obtain a crude product, and then the crude product was separated and purified by a chromatography column (filler: silica gel), and the mobile phase was composed of petroleum ether and dichloromethane (the volume ratio of petroleum ether to dichloromethane was 1:1), and a purified product (white solid) was obtained, and the yield of the organic compound M3 was 93.56%, and the nuclear magnetic resonance data were: 1 H NMR(500MHz,Chloroform-d)δ8.50(d,2H),8.20-8.17(m,1H),8.08-8.00(m,3H),7.94-7.88(m,3H),7 .63-7.53(m,8H),7.51-7.48(m,2H),7.29-7.25(m,2H),7.20-7.06(m,6H),6.96(m,2H),1.62(s,6H).

[0166] Organic Compound Example 4

[0167] This embodiment provides an organic compound M4 and a preparation method thereof. The synthesis route of the organic compound M4 is as follows:

[0168]

[0169] Compared with the preparation method of organic compound M3, the preparation method of organic compound M4 is different in that: in step S3.3, "43.28 mmol of 6,12-dibromo " replaced by "43.28mmol of 2,8-dibromo (CAS No. 50637-63-3)", and replace "25.38 mmol of compound M3-3" in step S3.4 with "25.38 mmol of 4-3", and replace "1.15 mmol of tetrabutylammonium bromide" in step S3.4 with "1.55 mmol of tetrabutylammonium bromide", and finally obtain a white solid. The yield of organic compound M4 is 92.40%, and the NMR data are: 1 H NMR(500MHz,Chloroform-d)δ8.64(m,2H),8.49-8.43(m,2H),8.29(m,1H),8.24-8.20(m,1H),8.09(m,2H),8.03-7.90(m ,6H),7.60-7.53(m,4H),7.49(m,1H),7.29-7.25(m,2H),7.22-7.18(m,2H),7.16-7.07(m,4H),6.96(m,2H),1.62(s,6H).

[0170] Organic compound comparative example 1

[0171] This comparative example provides an organic compound P1, which has a structure shown in the following formula (B-1):

[0172]

[0173] Organic compound comparative example 2

[0174] This comparative example provides an organic compound P2, which has a structure shown in the following formula (B-2):

[0175]

[0176] Composition Example 1

[0177] This embodiment provides a composition, which is composed of 98% of an organic compound M1 (having a structure shown in formula (A-1)) and 2% of an organic compound BD, calculated by mass percentage, wherein the organic compound BD has a structure shown in formula (B-3) below:

[0178]

[0179] Composition Example 2

[0180] This embodiment provides a composition, which is composed of 98% of an organic compound M2 (having a structure shown in formula (A-2)) and 2% of an organic compound BD (having a structure shown in formula (B-3)) calculated by mass percentage.

[0181] Composition Example 3

[0182] This embodiment provides a composition, which is composed of 98% of an organic compound M3 (having a structure shown in formula (A-3)) and 2% of an organic compound BD (having a structure shown in formula (B-3)) calculated by mass percentage.

[0183] Composition Example 4

[0184] This embodiment provides a composition, which is composed of 98% of an organic compound M4 (having a structure shown in formula (A-4)) and 2% of an organic compound BD (having a structure shown in formula (B-3)) calculated by mass percentage.

[0185] Composition Comparative Example 1

[0186] This embodiment provides a composition, which is composed of 98% of an organic compound P1 (having a structure shown in formula (B-1)) and 2% of an organic compound BD (having a structure shown in formula (B-3)) calculated by mass percentage.

[0187] Composition Comparative Example 2

[0188] This embodiment provides a composition, which is composed of 98% of an organic compound P2 (having a structure shown in formula (B-2)) and 2% of an organic compound BD (having a structure shown in formula (B-3)) calculated by mass percentage.

[0189] Device Example 1

[0190] This embodiment provides a photoelectric device and a method for preparing the same. The photoelectric device is an organic light emitting diode having a positive structure, such as Figure 2As shown, in the direction from bottom to top, the optoelectronic device 10 includes an anode 101, a plurality of functional layers and a cathode 102 stacked in sequence, wherein the plurality of functional layers include a hole functional layer 1032, a light-emitting layer 1031 and an electron functional layer 1033 stacked in sequence, wherein the electron functional layer 1033 is closer to the cathode 102 than the hole functional layer 1032. The hole functional layer 1032 is composed of a hole injection layer 10321 and an electron blocking layer 10322 stacked in sequence, wherein the electron blocking layer 10322 is closer to the light-emitting layer 1031 than the hole injection layer 10321; the electron functional layer 1033 is composed of an electron transport layer 10331 and an electron injection layer 10332 stacked in sequence, wherein the electron injection layer 10332 is closer to the cathode 102 than the electron transport layer 10331. The light-emitting area of ​​the optoelectronic device 10 is 0.04 cm 2 .

[0191] The materials and thicknesses of the various layers in the optoelectronic device 10 are as follows:

[0192] The material of the anode 101 is ITO, and the average thickness of the anode 101 is 50 nm;

[0193] The material of cathode 102 is Al, and the average thickness of cathode 102 is 100 nm;

[0194] The material of the hole injection layer 10321 is PEDOT:PSS, and the average thickness of the hole injection layer 10321 is 40 nm;

[0195] The material of the electron blocking layer 10322 is 4,4',4"-tri(carbazole-9-yl)triphenylamine (TCTA, CAS No. 139092-78-7), and the average thickness of the electron blocking layer 10322 is 40 nm;

[0196] The material of the light-emitting layer 1031 is an organic compound M1 (having a structure shown in formula (A-1)), and the average thickness of the light-emitting layer 1031 is 20 nm;

[0197] The material of the electron transport layer 10331 is 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi for short, CAS No. 192198-85-9), and the average thickness of the electron transport layer 10331 is 30 nm;

[0198] The material of the electron injection layer 10332 is lithium fluoride (LiF), and the average thickness of the electron injection layer 10332 is 1 nm.

[0199] The method for preparing the optoelectronic device in this embodiment comprises the following steps:

[0200] S10.1, providing an ITO conductive glass substrate with a sheet resistance of 15Ω, and sequentially performing acetone ultrasonic cleaning for 15 minutes, Lanju detergent ultrasonic cleaning for 15 minutes, deionized water ultrasonic cleaning for 15 minutes, and isopropanol ultrasonic cleaning for 15 minutes on the ITO conductive glass substrate, and then plasma treating for 10 minutes to obtain a substrate including an anode;

[0201] S10.2, in a clean room, spin-coating a PEDOT:PSS aqueous solution on one side of an ITO conductive glass substrate, and then heat-treating it at a constant temperature of 180° C. to solidify it into a film, thereby obtaining a hole injection layer;

[0202] S10.3, in a nitrogen glove box, spin-coating a 5 mg / mL TCTA-toluene solution on the side of the hole injection layer away from the anode, and then heat-treating at 180° C. in a nitrogen atmosphere to cure the film to obtain an electron blocking layer;

[0203] S10.4, in a nitrogen glove box, spin-coat a 15 mg / mL solution of an organic compound M1-methyl benzoate on the side of the electron blocking layer away from the hole injection layer, and then heat-treat at a constant temperature of 140° C. in a nitrogen atmosphere to solidify the film to obtain a light-emitting layer;

[0204] S10.5, forming an electron transport layer and an electron injection layer in sequence on the side of the light-emitting layer away from the electron blocking layer, and then placing the obtained stacked structure in a vacuum of not more than 3×10 -4 In the Pa evaporation chamber, Al is thermally evaporated on the side of the electronic functional layer away from the light-emitting layer by a thermal evaporation process to obtain a cathode;

[0205] S10.6. In a nitrogen glove box, encapsulate the organic light emitting diode with ultraviolet curing resin.

[0206] Device Example 2

[0207] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the material of the light-emitting layer is replaced by "organic compound M2 (having the structure shown in formula (A-2))".

[0208] Device Example 3

[0209] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the material of the light-emitting layer is replaced by "organic compound M3 (having the structure shown in formula (A-3))".

[0210] Device Example 4

[0211] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the material of the light-emitting layer is replaced by "organic compound M4 (having the structure shown in formula (A-4))".

[0212] Device Example 5

[0213] This embodiment provides a photoelectric device and a method for preparing the same. The photoelectric device is an organic light emitting diode having a positive structure, such as Figure 3 As shown, in the direction from bottom to top, the optoelectronic device 10 includes an anode 101, a plurality of functional layers and a cathode 102 stacked in sequence, wherein the plurality of functional layers include a hole functional layer 1032, a light-emitting layer 1031 and an electron functional layer 1033 stacked in sequence, wherein the electron functional layer 1033 is closer to the cathode 102 than the hole functional layer 1032. The hole functional layer 1032 is composed of a hole injection layer 10321, a hole transport layer 10323 and an electron blocking layer 10322 stacked in sequence, wherein the electron blocking layer 10322 is closer to the light-emitting layer 1031 than the hole injection layer 10321; the electron functional layer 1033 is composed of an electron transport layer 10331 and an electron injection layer 10332 stacked in sequence, wherein the electron injection layer 10332 is closer to the cathode 102 than the electron transport layer 10331. The light-emitting area of ​​the optoelectronic device 10 is 0.04 cm 2 .

[0214] The materials and thicknesses of the various layers in the optoelectronic device 10 are as follows:

[0215] The material of the anode 101 is ITO, and the average thickness of the anode 101 is 50 nm;

[0216] The material of cathode 102 is Al, and the average thickness of cathode 102 is 100 nm;

[0217] The material of the hole injection layer 10321 is 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (CAS No. 105598-27-4), and the average thickness of the hole injection layer 10321 is 5 nm;

[0218] The material of the hole transport layer 10323 is N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (abbreviated as NPB, CAS No. 123847-85-8), and the average thickness of the hole transport layer 10323 is 40 nm;

[0219] The material of the electron blocking layer 10322 is 4,4',4"-tri(carbazole-9-yl)triphenylamine (TCTA, CAS No. 139092-78-7), and the average thickness of the electron blocking layer 10322 is 5 nm;

[0220] The material of the light-emitting layer 1031 is the composition in Composition Example 1, and the average thickness of the light-emitting layer 1031 is 20 nm;

[0221] The material of the electron transport layer 10331 is 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi for short, CAS No. 192198-85-9), and the average thickness of the electron transport layer 10331 is 40 nm;

[0222] The material of the electron injection layer 10332 is lithium fluoride (LiF), and the average thickness of the electron injection layer 10332 is 1 nm.

[0223] Device Example 6

[0224] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 5, the difference of the photoelectric device in this embodiment is that the material of the light-emitting layer is replaced by "the composition in composition embodiment 2".

[0225] Device Example 7

[0226] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 5, the difference of the photoelectric device in this embodiment is that the material of the light-emitting layer is replaced by "the composition in composition embodiment 3".

[0227] Device Example 8

[0228] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 5, the difference of the photoelectric device in this embodiment is that the material of the light-emitting layer is replaced by the "composition in composition embodiment 4".

[0229] Device Comparative Example 1

[0230] This comparative example provides a photoelectric device. Compared with the photoelectric device in device example 1, the photoelectric device in this comparative example is different in that the material of the light-emitting layer is replaced by "organic compound P1 (having the structure shown in formula (B-1))".

[0231] Device Comparison Example 2

[0232] This comparative example provides a photoelectric device. Compared with the photoelectric device in device example 1, the difference of the photoelectric device in this comparative example is that the material of the light-emitting layer is replaced by "organic compound P2 (having the structure shown in formula (B-2))".

[0233] Device Comparison Example 3

[0234] This comparative example provides a photoelectric device. Compared with the photoelectric device in device example 5, the photoelectric device in this comparative example is different in that the material of the light-emitting layer is replaced with the "composition in composition comparative example 1".

[0235] Device Comparison Example 4

[0236] This comparative example provides a photoelectric device. Compared with the photoelectric device in device example 5, the photoelectric device in this comparative example is different in that the material of the light-emitting layer is replaced with the "composition in composition comparative example 2".

[0237] Experimental Example 1

[0238] The organic compounds M1 to M4 were subjected to performance tests, and the performance test items included: ultraviolet absorption and fluorescence emission spectra, electrochemical-cyclic voltammetry characteristic curves, and thermogravimetric analysis.

[0239] The detection method of ultraviolet absorption and fluorescence emission spectrum includes the steps of: dissolving a single organic compound to be detected in toluene to prepare an organic compound-toluene solution (the concentration of the organic compound is 10 -5 mol / L), and the organic compound-toluene solution was tested by UV absorption and fluorescence emission spectra. Figure 4 and Figure 5 As shown by Figure 4 and Figure 5 It can be seen that the organic compounds M1 to M4 have good ultraviolet absorption characteristics and blue light fluorescence emission characteristics.

[0240] Electrochemical-cyclic voltammetry was used to detect the HOMO energy level and LUMO energy level of the organic compound to be tested, and organic compound P1 was used as a reference. The test results are as follows Figure 6 As shown in Table 1 below:

[0241] Table 1

[0242]

[0243] It can be seen from Table 1 that the LUMO energy levels of organic compounds M1 to M4 are between -2.41eV and -2.24eV, and the HOMO energy levels of organic compounds M1 to M4 are between -5.40eV and -5.23eV, and the energy level differences are greater than 3eV, and they can be used as blue light emitting host materials.

[0244] The thermogravimetric analysis results of organic compounds M1 to M4 are as follows: Figure 7As shown, the thermal decomposition temperatures of organic compounds M1 to M4 (corresponding to 5 wt% weight loss of organic compounds) are all over 400° C., indicating that organic compounds M1 to M4 have good thermal stability and meet the needs of practical applications.

[0245] Experimental Example 2

[0246] The performance of the optoelectronic devices in device examples 1 to 4, device comparative examples 1 and device comparative examples 2 was tested. The current-voltage (JV) characteristics of each optoelectronic device were tested using IVL optical property measurement equipment, and important parameters were recorded: CIE color coordinates (x, y), turn-on voltage (U T ,V), maximum brightness (L max ,cd / m 2 ) and the maximum current efficiency (CE max , cd / A). The performance test was carried out in an environment with a temperature of 25°C and a humidity of 40%. The performance test results are shown in Table 2 below:

[0247] Table 2

[0248]

[0249]

[0250] It can be seen from Table 2 that compared with the comprehensive performance of the optoelectronic devices in device comparative examples 1 and 2, the comprehensive performance of the optoelectronic devices in device examples 1 to 4 has significant advantages, which are specifically manifested as follows: the optoelectronic devices in device examples 1 to 4 have good color purity, and the emission spectrum peaks are all around 460nm, showing pure blue light emission; the optoelectronic devices in device examples 1 to 4 have lower turn-on voltages, which are all less than 4V; the optoelectronic devices in device examples 1 to 4 have higher brightness, which is greater than 15000cd / m 2 ; and, the optoelectronic devices in device examples 1 to 4 have higher device efficiencies, all of which are greater than 7 cd / A, which indicates that the organic compound represented by general formula (I) is conducive to the preparation of high-efficiency and high-color-purity blue light-emitting organic diodes.

[0251] Experimental Example 3

[0252] The performance of the optoelectronic devices in device examples 5 to 8, device comparative examples 3 and device comparative example 4 was tested. The current-voltage (JV) characteristics of each optoelectronic device were tested using IVL optical property measurement equipment, and important parameters were recorded: CIE color coordinates (x, y), turn-on voltage (U T ,V), maximum brightness (L max ,cd / m2 ) and the maximum current efficiency (CE max , cd / A). The performance test was carried out in an environment with a temperature of 25°C and a humidity of 40%. The electroluminescence spectra of device embodiments 5 to 8 are shown in FIG. Figure 8 The performance test results are shown in Table 3 below:

[0253] Table 3

[0254]

[0255] It can be seen from Table 3 that compared with the comprehensive performance of the optoelectronic devices in device examples 3 and 4, the comprehensive performance of the optoelectronic devices in device examples 5 to 8 has significant advantages, which are specifically manifested as follows: the optoelectronic devices in device examples 5 to 8 have good color purity, and the emission spectrum peaks are all around 460nm, showing pure blue light emission; the optoelectronic devices in device examples 1 to 4 have lower turn-on voltages, which are all less than 4.5V; the optoelectronic devices in device examples 1 to 4 have higher brightness, which is greater than 16800cd / m 2 ; and, the optoelectronic devices in device embodiments 1 to 4 have higher device efficiency, and the device efficiency is greater than 8.9 cd / A, which shows that the organic compound represented by general formula (Ⅰ) can be used as the main light-emitting material of the blue light organic light-emitting diode, which is beneficial to improve the color purity and device efficiency of the blue light organic light-emitting diode.

[0256] The above is a detailed introduction to an organic compound, a composition, and an optoelectronic device provided in 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 technical solutions and core ideas of the present application; ordinary technicians in this field should understand that they can still modify the technical solutions recorded in the aforementioned embodiments, or replace some of the technical features therein by equivalents; and these modifications or replacements do not make the corresponding technical solutions deviate from the scope of the technical solutions of the embodiments of the present application.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in the following general formula (I): In the general formula (I), Ar1 and Ar2 are independently selected from aromatic rings having 6 to 30 ring atoms; R1 is selected from an electron-donating group, and R2 is selected from an aryl group having 6 to 30 ring atoms which is unsubstituted or substituted by at least one substituent, and a heteroaryl group having 5 to 30 ring atoms which is unsubstituted or substituted by at least one substituent; Wherein, each time the substituent appears, it is independently selected from -D, a halogen group, -OH, -NH2, -SH, a C1-C30 alkyl group, a C2-C30 alkenyl group, a C2-C30 alkynyl group, a C1-C30 alkoxy group, a C1-C30 alkoxycarbonyl group, a C1-C30 alkylacyloxy group or a combination of these groups.

2. The organic compound according to claim 1, characterized in that The R1 and the R2 are the same or different; And / or, the R1 is selected from the group represented by the following formula (1-1) or formula (1-2): In formula (1-1), X is selected from NR5, R5 is selected from -H, -D, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C1-C30 alkoxy, aryl having 6 to 30 ring atoms, heteroaryl having 5 to 30 ring atoms, or a combination of these groups; In formula (1-2), Y-* is selected from N-* or N-R6-*, and R6 is selected from C1-C30 alkylene, C2-C30 alkenylene, C2-C30 alkynylene, C1-C30 alkyleneoxy, arylene having 6 to 30 ring atoms, heteroarylene having 5 to 30 ring atoms, or a combination of these groups; In formula (1-1) and formula (1-2), R3 and R4, when they appear each time, are independently selected from -H, -D, -OH, -NH2, -SH, -NR7R8, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C1-C30 alkoxy, or a combination of these groups; R7 and R8 are independently selected from -H, -D, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C1-C30 alkoxy, aryl with 6 to 30 ring atoms, heteroaryl with 5 to 30 ring atoms, or a combination of these groups; Adjacent R3 and R4 are not connected, or adjacent R3 and R4 are connected to form a ring structure with X or Y; n1 and n2 are each independently selected from integers of 0-5.

3. The organic compound according to claim 1, characterized in that The R1 is selected from any one of the following groups: wherein R7 and R8 are independently selected from C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C1-C10 alkoxy or a combination of these groups; optionally, R7 and R8 are independently selected from methyl, ethyl, propyl, butyl, pentyl, methoxy, ethoxy, vinyl or ethynyl; And / or, R2 is selected from phenyl or substituted phenyl, naphthyl or substituted naphthyl, and each time the substituent appears, it is independently selected from -D, a halogen group, -OH, -NH2, -SH, a C1-C10 alkyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, a C1-C10 alkoxy group or a combination of these groups.

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

5. A method for preparing an organic compound, characterized in that: For preparing the organic compound as claimed in any one of claims 1 to 4, the preparation method of the organic compound comprises the following steps: (A1) mixing a first compound of the general formula R1-X1 and biboric acid pinacol ester to carry out a first reaction to obtain a second compound; (A2) mixing a third compound of the general formula R2-X2 and biboric acid pinacol ester to carry out a second reaction to obtain a fourth compound; (A3) mixing the fourth compound and the fifth compound to perform a third reaction to obtain a sixth compound; (A4) mixing the second compound and the sixth compound to carry out a fourth reaction to obtain an organic compound having a structure represented by the general formula (I); Wherein, the second compound has the structure shown in the following formula (II): The fourth compound has a structure shown in the following formula (III): The fifth compound has a structure shown in the following formula (IV): The sixth compound has a structure shown in the following general formula (V): X1 to X4 are each independently selected from F, Cl, Br or I.

6. The preparation method according to claim 5, characterized in that: Step (A1) comprises: in an atmosphere of a first inert gas, reacting a first reaction system comprising the first compound, bipyraclostrobin, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride and potassium acetate to generate the second compound; wherein the molar ratio of the first compound to bipyraclostrobin is 1:(1-1.2), and / or the temperature of the first reaction is 80° C.-90° C., and / or the time of the first reaction is 11 h-13 h; optionally, the solvent of the first reaction system is 1,4-dioxane, and / or the first inert gas is selected from one or more of nitrogen, argon, helium, neon, krypton and xenon; And / or, step (A2) comprises: in an atmosphere of a second inert gas, reacting a second reaction system comprising the third compound, bipyraclostrobin, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride and potassium acetate to generate the fourth compound; wherein the molar ratio of the third compound to bipyraclostrobin is 1:(1-1.2), and / or the temperature of the second reaction is 80°C-90°C, and / or the time of the second reaction is 11h-13h; optionally, the solvent of the second reaction system is 1,4-dioxane, and / or the second inert gas is selected from one or more of nitrogen, argon, helium, neon, krypton and xenon; And / or, step (A3) comprises: in an atmosphere of a third inert gas, reacting a third reaction system comprising the fourth compound, the fifth compound, tetrakis(triphenylphosphine)palladium, tetrabutylammonium halide and potassium carbonate to generate the sixth compound; wherein the molar ratio of the fourth compound to the fifth compound is 1:(1-1.2), and / or the temperature of the third reaction is 80°C-90°C, and / or the time of the third reaction is 11h-13h; optionally, the solvent of the third reaction system is toluene, and / or the tetrabutylammonium halide is tetrabutylammonium bromide, and / or the third inert gas is selected from one or more of nitrogen, argon, helium, neon, krypton and xenon; And / or, step (A4) comprises: in an atmosphere of a fourth inert gas, reacting a fourth reaction system comprising the second compound, the sixth compound, tetrakis(triphenylphosphine)palladium, tetrabutylammonium halide and potassium carbonate to generate an organic compound having a structure represented by general formula (I); wherein the molar ratio of the second compound to the sixth compound is 1:(1-1.2), and / or the temperature of the fourth reaction is 80°C-90°C, and / or the time of the fourth reaction is 11h-13h; optionally, the solvent of the fourth reaction system is toluene, and / or the tetrabutylammonium halide is tetrabutylammonium bromide, and / or the fourth inert gas is selected from one or more of nitrogen, argon, helium, neon, krypton and xenon; And / or, the fifth compound has a structure shown in the following formula (VI): And / or, the sixth compound has a structure shown in the following formula (VII):

7. A composition, characterized in that The composition comprises the organic compound as described in any one of claims 1 to 4, or the organic compound prepared by the preparation method as described in claim 5 or 6.

8. The composition according to claim 7, characterized in that The composition further comprises at least one organic functional material, wherein the organic functional material is selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material or a light emitting material; And / or, the composition further comprises at least one first organic solvent; optionally, the first organic solvent is selected from at least one of aromatic or heteroaromatic-based solvents, ester-based solvents, aromatic ketone-based solvents, aromatic ether-based solvents, aliphatic ketones, aliphatic ethers, alicyclic compounds, olefin compounds, borate ester compounds and phosphate ester compounds.

9. A photoelectric device, characterized in that: include: An anode and a cathode arranged opposite to each other; as well as A plurality of functional layers are disposed between the anode and the cathode; Among them, the material of at least one of the multiple functional layers includes the organic compound described in any one of claims 1 to 4, or the organic compound prepared by the preparation method described in claim 5 or 6, or at least one of the multiple functional layers is prepared using the composition described in claim 7 or 8.

10. The optoelectronic device according to claim 9, characterized in that: The multiple functional layers include a light-emitting layer, the material of the light-emitting layer includes the organic compound described in any one of claims 1 to 4, or the organic compound prepared by the preparation method described in claim 5 or 6, or the light-emitting layer is prepared using the composition described in claim 7 or 8.

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