Organic compound, preparation method of organic compound, thin film and photoelectric device

Abstract

The invention provides an organic compound, a preparation method of the organic compound, a thin film and a photoelectric device. The organic compound provided by the invention has relatively good heat resistance, hole migration capability and the like, and the performance of a device can be improved when the organic compound is used for preparing the photoelectric device.

Description

Technical Field

[0001] This application relates to the field of optoelectronic technology, specifically to an organic compound, a method for preparing the organic compound, a thin film, and an optoelectronic device. Background Technology

[0002] Hole transport materials are organic semiconductor materials that can achieve directional, orderly, and controllable migration of holes under the influence of an electric field, thereby enabling charge transport.

[0003] The hole transport materials that have been developed so far are still insufficient to meet the needs of different application scenarios, and more hole transport materials need to be developed to expand the types of hole transport materials. Summary of the Invention

[0004] This application provides an organic compound, a method for preparing the organic compound, a thin film, and an optoelectronic device, which can increase the application scenarios of hole transport materials.

[0005] In a first aspect, embodiments of this application provide an organic compound,

[0006] It has a structure as shown in general formula (1):

[0007]

[0008] Secondly, embodiments of this application provide a method for preparing an organic compound, comprising the following steps:

[0009] The first compound and the second compound were mixed and reacted in solution to obtain the first intermediate;

[0010] A third compound is provided, and the third compound is mixed and reacted with the first intermediate to obtain a first organic compound;

[0011] A halogenated reagent is provided, and the halogenated reagent is mixed with the first organic compound and reacted to obtain a second intermediate;

[0012] A fourth compound is provided, and the fourth compound is mixed and reacted with the second intermediate to obtain the organic compound.

[0013] Thirdly, embodiments of this application provide a thin film comprising the organic compound as described above, or an organic compound prepared by the method described above.

[0014] Fourthly, embodiments of this application provide an optoelectronic device, comprising:

[0015] The first and second electrodes are arranged opposite to each other; and

[0016] Multiple functional layers are disposed between the first electrode and the second electrode;

[0017] The material of at least one of the plurality of functional layers includes the organic compounds described above.

[0018] The beneficial effects of the embodiments of this application are as follows:

[0019] The organic compounds provided in this application have good heat resistance and hole migration ability, and their use in the preparation of optoelectronic devices can improve the performance of the devices. Attached Figure Description

[0020] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0021] Figure 1 This is a schematic diagram of the structure of the optoelectronic device embodiment 1 provided in the embodiments of this application.

[0022] Explanation of reference numerals in the attached figures:

[0023] 1. Anode; 2. Hole injection layer; 3. Hole transport layer; 4. Excitation layer; 5. Electron transport layer; 6. Cathode. Detailed Implementation

[0024] The technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of this application, and not all embodiments. Based on the embodiments of this application, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this application. Furthermore, it should be understood that the specific embodiments described herein are only for illustration and explanation of this application and are not intended to limit this application.

[0025] In this application, unless otherwise stated, directional terms such as "upper" and "lower" generally refer to the upper and lower positions of the device in its actual use or operating state, specifically the drawing directions in the accompanying drawings; while "inner" and "outer" refer to the outline of the device. Furthermore, in the description of this application, the term "comprising" means "including but not limited to". The terms first, second, third, etc., are used merely as illustrative purposes and do not impose numerical requirements or establish a numerical order.

[0026] In this application, "and / or" describes the relationship between related objects, indicating that three relationships can exist. For example, A and / or B can represent: A existing alone, A and B existing simultaneously, or B existing alone. A and B can be singular or plural.

[0027] In this application, "at least one" means one or more, and "more than one" means two or more. "At least one," "at least one of the following," or similar expressions refer to any combination of these items, including any combination of single or multiple items. For example, "at least one of a, b, or c," or "at least one of a, b, and c," can both mean: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, and c can be single or multiple.

[0028] In this application, the term "on" forming another layer on a certain layer is a broad concept. It can mean that the formed other layer is adjacent to a certain layer, or it can mean that there are other spacer structures between the other layer and the certain layer. For example, when a second electrode is formed "on" a first charge carrier functional layer, the term "on" can mean that the formed second electrode is adjacent to the first charge carrier functional layer, or it can mean that there are other spacer structures between the second electrode and the first charge carrier functional layer, such as a light-emitting layer.

[0029] Various embodiments of this application may exist in the form of a range; it should be understood that the description in the form of a range is merely for convenience and brevity and should not be construed as a hard limitation on the scope of this application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single numerical values ​​within that range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., and single numbers within the range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. Furthermore, whenever a numerical range is referred to herein, it means including any referenced number (fraction or integer) within the referred range.

[0030] The term "including" means "including but not limited to". The term "and / or" describes the relationship between related objects, indicating that three relationships can exist. For example, A and / or B can represent: A alone, A and B simultaneously, or B alone. A and B can be singular or plural. The term "at least one" means one or more, and "more than one" means two or more. The terms "at least one", "at least one of the following", or similar expressions refer to any combination of these items, including any combination of a single or plural type. 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 each be a single or multiple type.

[0031] The term "substitution" means that a hydrogen atom in a substituent is replaced by a substituent.

[0032] In this application, when the same substituent appears multiple times, each substituent can be independently selected from different groups. For example, if the general formula contains multiple R... 1 Then R 1 It can be independently selected from different groups.

[0033] The term "ring atom number" refers to the number of atoms in a ring-forming compound formed by atomic bonds, such as monocyclic compounds, fused-ring compounds, cross-linked compounds, carbocyclic compounds, and heterocyclic compounds. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" as described below unless otherwise specified. For example, the benzene ring has 6 ring atoms, the naphthalene ring has 10 ring atoms, and the thiophene group has 5 ring atoms.

[0034] The term "aliphatic chain hydrocarbon group" refers to an aliphatic straight-chain hydrocarbon group or an aliphatic branched hydrocarbon group. "C1-C30 aliphatic chain hydrocarbon group" can be, for example, an aliphatic chain hydrocarbon group of C1-C20, C1-C18, C1-C15, C1-C12, C1-C10, C1-C8, or C1-C6. The number of carbon atoms in the chain hydrocarbon group can be, for example, 1 to 3, 1 to 6, 1 to 8, 1 to 10, 1 to 12, or 1 to 15, with examples being 1, 3, 6, 8, 10, 15, 20, 25, 30, or any value between any two of the aforementioned values. For example, it can be C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, C9 alkyl, or C10 alkyl. Suitable examples of "chain hydrocarbon group" include, but are not limited to, methyl, ethyl, vinyl, ethynyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, n-nonyl, n-decyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, etc.

[0035] The term "aliphatic hydrocarbon oxy group" refers to a group with the general formula *-O-aliphatic hydrocarbon, where * indicates a bonding site and O represents an oxygen atom. Suitable examples include, but are not limited to, methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), tert-butoxy (-OC(CH3)3 or -OtBu), and n-hexyloxy (-O-C6H). 13 ), n-Decaalkoxy (-OC) 10 H 21 ), or n-dodecyloxy (-OC) 12 H 25 ).

[0036] The term "aliphatic hydrocarbon mercapto" refers to a group with the formula *-R s1 -SR s2 The structural features, * indicates a connection site, S represents a sulfur atom, and "R" indicates a linking site. s1 "is an aliphatic chain-like hydrocarbon group or an aliphatic cyclic hydrocarbon group," R s2 "is H, aliphatic chain hydrocarbon group or aliphatic cyclic hydrocarbon group;

[0037] The term "aliphatic chain alkylene group" refers to a group derived from an aliphatic chain hydrocarbon compound by removing two hydrogen atoms, such as -CH2-.

[0038] The term "chain alkylene" refers to a group derived from an alkane by removing two hydrogen atoms, such as -CH2-.

[0039] The term "chain alkylene" refers to a group derived from an alkane by removing two hydrogen atoms, such as -CH2-.

[0040] The term "chain alkoxide" refers to a group derived from an alkoxy group by removing two hydrogen atoms, such as -CH2-O-CH2-. The term "aliphatic cyclic hydrocarbon group" refers to an aliphatic cyclic hydrocarbon group. The number of ring atoms in an "aliphatic cyclic hydrocarbon group with 3 to 30 ring atoms" can be, for example, 3 to 5, 3 to 8, 3 to 10, 3 to 14, 3 to 20, or 5 to 10, with examples being 3, 5, 6, 8, 10, 14, 20, 24, 28, 30, or values ​​between any two of the aforementioned values. Suitable examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, or adamantyl.

[0041] The term "aliphatic heterocyclic hydrocarbon group" refers to an aliphatic cyclic hydrocarbon group in which at least one carbon atom is replaced by a non-carbon atom. The non-carbon atom can be one or more of N, O, S, Si, and P atoms, and the number of heteroatoms in the aliphatic heterocyclic hydrocarbon group is independently between 1 and 20. The number of ring atoms in "aliphatic heterocyclic hydrocarbon group with 3 to 30 ring atoms" can be, for example, 3 to 5, 3 to 8, 3 to 10, 3 to 14, 3 to 20, or 5 to 10, with examples being 3, 5, 6, 8, 10, 14, 20, 24, 28, 30, or values ​​between any two of the aforementioned values.

[0042] The term "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. This group can be monocyclic, fused-ring, or polycyclic, and in the case of a polycyclic ring, at least one ring is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 6-40 ring atoms" means an aryl group containing 6-40 ring atoms, preferably a substituted or unsubstituted aryl group having 6-30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6-18 ring atoms, and particularly preferably a substituted or unsubstituted aryl group having 6-14 ring atoms, with optional further substitution of the aryl group. Suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl, and their derivatives. It is understandable that multiple aryl groups can also be interrupted by short non-aromatic units (e.g., non-H atoms with a molar ratio of less than 10%, such as C, N, or O atoms). Specific examples such as acenaphthene, fluorene, 9,9-diarylfluorene, triarylamines, and diaryl ether systems should also be included in the definition of aryl groups.

[0043] The term "heteroaryl or heteroaromatic group" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, O atom, S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5-40 ring atoms" refers to a heteroaryl group having 5-40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6-30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6-18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl group having 6-14 ring atoms. The heteroaryl group may optionally be further substituted, and suitable examples include, but are not limited to: thiophene, furanyl, pyrrole, imidazolyl, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, and pyrimidine. Triazinyl, acridineyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidinyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienopyrrolyl, furanolyl, furanolyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridineyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0044] The term "alkyl" can refer to a straight-chain, branched, and / or cyclic alkyl group. The number of carbon atoms in an alkyl group can be 1-50, 1-30, 1-20, 1-18, 1-15, 1-12, 1-10, 1-8, 1-6, or 1-3. Phrases containing this term, such as "C1-9 alkyl," refer to alkyl groups containing 1-9 carbon atoms, and each time it appears, it can independently be C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, and 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, etc.

[0045] The term "aryloxy group" refers to a group with the general formula *-O-aryl, where * represents a linking site and O represents an oxygen atom. "Aryloxy group with 6 to 30 ring atoms" can be an aryloxy group with 6 to 20 ring atoms, an aryloxy group with 6 to 18 ring atoms, an aryloxy group with 6 to 16 ring atoms, an aryloxy group with 6 to 14 ring atoms, or an aryloxy group with 6 to 10 ring atoms. The number of ring atoms can be, for example, 6, 10, 12, 14, 16, 18, 20, 24, 26, 28, 30, or any two of the aforementioned values.

[0046] The term "arylamino" refers to the general formula... . group.

[0047] Ar5 and Ar6 are each independently selected from -H, -D, unsubstituted or substituted aryl groups having 6 to 30 ring atoms, or combinations thereof, and at least one of Ar5 and Ar6 is selected from unsubstituted or substituted aryl groups having 6 to 30 ring atoms; R 12 and R 13Ar7 is selected independently from -H, -D, unsubstituted or substituted with at least one R' C1-C30 aliphatic chain hydrocarbon group, unsubstituted or substituted with at least one R' C1-C30 aliphatic chain hydroxyl group, unsubstituted or substituted with at least one R' aryl group having 6 to 30 ring atoms, or combinations of the foregoing groups, wherein Ar7 is selected from unsubstituted or substituted with at least one R' substituted aryl group having 6 to 30 ring atoms. Each time R' appears, it is independently selected from -D, C1-C20 aliphatic chain hydrocarbon group, C1-C20 aliphatic chain hydroxyl group, aryl group having 6 to 30 ring atoms, or combinations of these groups. "Arylamino group with 6 to 30 ring atoms" can be an arylamino group with 6 to 20 ring atoms, an arylamino group with 6 to 18 ring atoms, an arylamino group with 6 to 16 ring atoms, an arylamino group with 6 to 14 ring atoms, or an arylamino group with 6 to 10 ring atoms. The number of ring atoms can be, for example, 6, 10, 12, 14, 16, 18, 20, 24, 26, 28, 30 or any two of the aforementioned values.

[0048] The term "arylthio" refers to a group with the general formula *-S-aryl, where * represents a linking site and S represents a sulfur atom. "Arylthio with 6 to 30 ring atoms" can be an arylthio with 6 to 20 ring atoms, an arylthio with 6 to 18 ring atoms, an arylthio with 6 to 16 ring atoms, an arylthio with 6 to 14 ring atoms, or an arylthio with 6 to 10 ring atoms. The number of ring atoms can be, for example, 6, 10, 12, 14, 16, 18, 20, 24, 26, 28, 30, or any two of the aforementioned values.

[0049] The term "heteroaryl group" refers to a group with the general formula *-O-heteroaryl, where * represents a linking site and O represents an oxygen atom. "Heteroaryl group with 5 to 30 ring atoms" can be a heteroaryl group with 5 to 20 ring atoms, a heteroaryl group with 5 to 18 ring atoms, a heteroaryl group with 5 to 16 ring atoms, a heteroaryl group with 5 to 14 ring atoms, a heteroaryl group with 5 to 12 ring atoms, or a heteroaryl group with 5 to 10 ring atoms. The number of ring atoms can be, for example, 5, 10, 12, 14, 18, 20, 24, 26, 28, 30, or any two of the aforementioned values.

[0050] The term "heteroaryl thio" refers to a group with the general formula *-S-heteroaryl, where * represents a linking site and S represents a sulfur atom. "Heteroaryl thio" having 5 to 30 ring atoms can be a heteroaryl thio with 5 to 20 ring atoms, a heteroaryl thio with 5 to 18 ring atoms, a heteroaryl thio with 5 to 16 ring atoms, a heteroaryl thio with 5 to 14 ring atoms, a heteroaryl thio with 5 to 12 ring atoms, or a heteroaryl thio with 5 to 10 ring atoms. The number of ring atoms can be, for example, 5, 10, 12, 14, 18, 20, 24, 26, 28, 30, or any two of the aforementioned values.

[0051] The term "heteroarylamino" refers to the general formula... . group.

[0052] Ar8 and Ar9 are each independently selected from -H, -D, unsubstituted or substituted with at least one R”, a heteroaryl group having 5 to 30 ring atoms, or a combination of these groups, and at least one of Ar8 and Ar9 is selected from an unsubstituted or substituted with at least one R”, a heteroaryl group having 5 to 30 ring atoms; R 14 and R 15 Ar is independently selected from -H, -D, unsubstituted or substituted with at least one R” C1-C30 aliphatic chain hydrocarbon group, unsubstituted or substituted with at least one R” C1-C30 aliphatic chain hydroxyl group, unsubstituted or substituted with at least one R” ring atom numbering 5 to 30 heteroaryl group, or a combination of the aforementioned groups. 10 Selected from unsubstituted or substituted with at least one R”, a heteroaryl group having 5 to 30 ring atoms. Each time R” appears, it is independently selected from -D, a C1 to C20 aliphatic chain hydrocarbon group, a C1 to C20 aliphatic chain hydroxyl group, a heteroaryl group having 5 to 30 ring atoms, or a combination of these groups. “A heteroarylamino group having 5 to 30 ring atoms” can be a heteroarylamino group having 5 to 20 ring atoms, a heteroarylamino group having 5 to 18 ring atoms, a heteroarylamino group having 5 to 16 ring atoms, a heteroarylamino group having 5 to 14 ring atoms, a heteroarylamino group having 5 to 12 ring atoms, or a heteroarylamino group having 5 to 10 ring atoms, the number of ring atoms being, for example, 5, 10, 12, 14, 18, 20, 24, 26, 28, 30, or any two of the foregoing values.

[0053] The term "arylene or arylene group" refers to a group derived from an aromatic ring compound by removing two hydrogen atoms, such as...

[0054] The term "heteroaryl or heteroaryl aromatic group" refers to a group derived from a heteroaryl ring compound by removing two hydrogen atoms, such as...

[0055] In this application, the single bond connecting the substituents extends through the corresponding ring, indicating that the substituent can be connected to any position on the ring. The terms "combinations thereof," "any combination thereof," and "any combination thereof" as used in this application include all suitable combinations of any two or more of the listed items.

[0056] The term "amino" refers to a derivative of an amine, characterized by the formula -N(X)2, where each "X" is independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic)2, -NH(heterocyclic), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic), -N(cycloalkyl)(heterocyclic), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0057] When no linking site is specified in the terminology group, it means that any linkable site in the group can be selected as the linking site.

[0058] The term "substituent-linked single bond piercing the corresponding ring" indicates that the substituent can be linked at any position on the pierced ring, for example... The R in the benzene ring can be attached to any substituted site on the benzene ring.

[0059] The term * indicates a linker site, where the single bond connecting the linker site traverses the corresponding loop, meaning that the linker site can be located anywhere on the traversed loop, for example... This indicates that all six C atoms on naphthalene can be connected.

[0060] the term This refers to cyclic compounds, which include aliphatic cyclic hydrocarbons, aliphatic heterocyclic hydrocarbons, aromatic compounds or heteroaromatic compounds, or combinations of these compounds; This indicates that two cyclic compounds are fused together, and one of the cyclic compounds can be fused at any position on the other cyclic compound.

[0061] The term # indicates a fusion site.

[0062] In this application, This indicates that the two C atoms on the benzene ring are fused sites.

[0063] The technical solution of this application is as follows:

[0064] In a first aspect, embodiments of this application provide an organic compound.

[0065] It has a structure as shown in general formula (1):

[0066]

[0067] Among them, R1, R x Each group is independently selected from one or more of the following: cyano, halogen, carboxyl, nitro, sulfonic acid, mercapto, aldehyde, or C1-C30 aliphatic hydrocarbon groups substituted with at least one R2.

[0068] Each time Ar1 appears, it is independently selected from aryl groups having 6 to 60 unsubstituted or substituted ring atoms with at least one R3, or heteroaryl groups having 5 to 60 unsubstituted or substituted ring atoms with at least one R3, or combinations of these groups; the heteroatoms in the heteroaryl groups are independently selected from one or more of N, S, O, P and Si.

[0069] Ar2 and Ar3 are each independently selected from the following groups:

[0070]

[0071] Where Y is independently selected from NR y S or O;

[0072] Ar4 is independently selected from unsubstituted or substituted Ar4 groups. z Substituted C1–C30 aliphatic chain hydrocarbon groups, unsubstituted or substituted with at least one R z The substituted aliphatic cyclic hydrocarbon group having 3 to 30 substituted ring atoms, either unsubstituted or substituted with at least one R z The substituted aliphatic heterocyclic hydrocarbon group having 3 to 30 ring atoms, either unsubstituted or substituted with at least one R z Substituted C1–C30 aliphatic chain alkyl oxygen, unsubstituted or substituted with at least one R z Substituted C1–C30 aliphatic chain hydrocarbon thiol group, unsubstituted or substituted with at least one R z Substituted C1–C30 aliphatic chain alkyl amino groups, unsubstituted or substituted with at least one R z The substituted aryl group has 6 to 60 cyclic atoms, and is either unsubstituted or substituted with at least one R group. z The substituted aryloxy group has 6 to 60 cyclic atoms, and is either unsubstituted or substituted with at least one R. z The substituted arylamino group has 6 to 60 ring atoms, and is either unsubstituted or substituted with at least one R. z The substituted aryl mercapto group has 6 to 60 cyclic atoms, and is either unsubstituted or substituted with at least one R group. z The substituted heteroaryl group has 5 to 60 cyclic atoms, is unsubstituted, or is substituted with at least one R zThe substituted heteroaryl groups having 5 to 60 cyclic atoms, are either unsubstituted or substituted with at least one R z The substituted heteroarylamino group has 5 to 60 ring atoms, or is unsubstituted or has at least one R z The substituted ring atoms are heteroaryl mercapto groups with a ring number of 5 to 60, or combinations of these groups;

[0073] R y Each occurrence is independently selected from H, D, unsubstituted, or by at least one R. w Substituted C1–C30 aliphatic chain hydrocarbon groups, unsubstituted or substituted with at least one R w The substituted aliphatic cyclic hydrocarbon group having 3 to 30 substituted ring atoms, either unsubstituted or substituted with at least one R w The substituted aliphatic heterocyclic hydrocarbon group having 3 to 30 ring atoms, either unsubstituted or substituted with at least one R w Substituted C1–C30 aliphatic hydrocarbon hydroxyl groups, unsubstituted or substituted with at least one R w Substituted C1-C30 alkyl mercapto groups, unsubstituted or with at least one R w The substituted ring atoms are 6 to 60 aryl groups, unsubstituted or substituted with at least one R group. w The substituted ring atoms are 6 to 60 aryloxy groups, unsubstituted or substituted with at least one R group. w The substituted heteroaryl group has 5 to 60 cyclic atoms, or is unsubstituted or has at least one R group. w The substituted heteroaryloxy group has a ring atom number of 5 to 60, or a combination of these groups;

[0074] R2, R3, R z and R w Each occurrence is independently selected from D, C1-C30 aliphatic chain hydrocarbon groups, C1-C30 aliphatic chain hydroxyl groups, aliphatic cyclic hydrocarbon groups with 3 to 30 ring atoms, aliphatic heterocyclic hydrocarbon groups with 3 to 30 ring atoms, aryl groups with 6 to 30 ring atoms, heteroaryl groups with 5 to 30 ring atoms, and -NR. N1 R N2 , halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, or aldehyde, or combinations of these groups; R N1 and R N2 Each of the following groups is independently selected from H, D, C1-C30 aliphatic chain hydrocarbon groups, C1-C30 aliphatic chain hydroxyl groups, aliphatic cyclic hydrocarbon groups with 3 to 30 ring atoms, aliphatic heterocyclic hydrocarbon groups with 3 to 30 ring atoms, aryl groups with 6 to 30 ring atoms, or heteroaryl groups with 5 to 30 ring atoms; n1 is an independent integer from 0 to 6 each time it appears;

[0075] # represents the fusion site. The above organic compounds have good molecular planarity, a rigid conjugated structure, good heat resistance, and are conducive to intramolecular charge transfer.

[0076] In some embodiments,

[0077] Each time Ar4 appears, it is independently selected from one or more of the following groups:

[0078]

[0079] In this case, X is selected independently from CR each time it appears. x1 Or N;

[0080] Z1 and Z2 are each selected independently from NR each time they appear. x2 CR x3 CR x4 R x5 , O or S;

[0081] Each occurrence of Z3 is independently selected from either N-* or NR. 10 -*;

[0082] R x1 R x2 R x3 R x4 and R x5 Each time it appears, it is independently selected from D, a substituted or at least R-substituted C1-C30 aliphatic chain hydrocarbon group, a substituted or at least R-substituted aliphatic cyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted aliphatic heterocyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted C1-C30 aliphatic hydrocarbon oxy group, a substituted or at least R-substituted C1-C30 aliphatic hydrocarbon thiol group, a substituted or at least R-substituted C1-C30 aliphatic hydrocarbon amino group, or a substituted or at least R-substituted aryl group having 6 to 30 ring atoms, or a combination of these groups; any two adjacent Rs x1 They can be connected to form a loop or not;

[0083] R4, R5, R6, R7, R8 and R9, each time appearing independently, are selected from a substituted or at least R-substituted C1 to C30 aliphatic chain hydrocarbon group, a substituted or at least R-substituted aliphatic cyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted aliphatic heterocyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted C1 to C30 aliphatic hydrocarbon oxy group, a substituted or at least R-substituted C1 to C30 aliphatic hydrocarbon thiol group, or a substituted or at least R-substituted C1 to C30 aliphatic hydrocarbon amino group, or a combination of these groups.

[0084] R 10 Selected from substituted or C1-C30 chain alkylene groups, substituted or C1-C30 chain alkene groups, substituted or C1-C30 chain alkene groups, substituted or C1-C30 aryl groups with 6 to 30 ring atoms, substituted or C1-C30 heteroaryl groups with 5 to 30 ring atoms, or combinations of these groups.

[0085] n2 and n3 are each independently selected from integers from 0 to 5;

[0086] n4 and n5 are each independently selected from integers from 0 to 4;

[0087] n6 and n7 are each independently selected from integers from 0 to 4;

[0088] When n2, n3, n4, n5, n6, and n7 are each independently selected from integers greater than or equal to 2, any two adjacent R4s can be connected to each other to form a cycle or not; any two adjacent R5s can be connected to each other to form a cycle or not; any two adjacent R6s can be connected to each other to form a cycle or not; any two adjacent R7s can be connected to each other to form a cycle or not; any two adjacent R8s can be connected to each other to form a cycle or not; any two adjacent R9s can be connected to each other to form a cycle or not.

[0089] Each time R appears, it is independently selected from one or more of H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C30 alkyl, C1-C30 alkoxy, and aryl with 6-30 ring atoms;

[0090] * indicates a connection point.

[0091] In some embodiments, R x1 R x2 R x3 R x4 and R x5Each time it appears, it is independently selected from H, D, a substituted or at least R-substituted C1-C20 aliphatic chain hydrocarbon group, a substituted or at least R-substituted aliphatic cyclic hydrocarbon group having 3 to 20 ring atoms, a substituted or at least R-substituted aliphatic heterocyclic hydrocarbon group having 3 to 20 ring atoms, a substituted or at least R-substituted C1-C20 aliphatic hydrocarbon oxy group, a substituted or at least R-substituted C1-C20 aliphatic hydrocarbon thiol group, a substituted or at least R-substituted C1-C20 aliphatic hydrocarbon amino group, or a substituted or at least R-substituted aryl group having 6 to 20 ring atoms, or a combination of these groups; any two adjacent Rs x1 Benzene rings or naphthalene rings are connected to each other;

[0092] And / or, each time R4, R5, R6, R7, R8 and R9 appear, they are independently selected from a substituted or at least R-substituted C1 to C20 aliphatic hydrocarbon group, a substituted or at least R-substituted aliphatic cyclic hydrocarbon group having 3 to 20 ring atoms, a substituted or at least R-substituted aliphatic heterocyclic hydrocarbon group having 3 to 20 ring atoms, a substituted or at least R-substituted C1 to C20 aliphatic hydrocarbon oxy group, a substituted or at least R-substituted C1 to C20 aliphatic hydrocarbon thiol group, or a substituted or at least R-substituted C1 to C20 aliphatic hydrocarbon amino group;

[0093] And / or, R 10 Selected from arylene groups having 6 to 20 ring atoms that are substituted or substituted with at least one R, heteroarylene groups having 5 to 20 ring atoms that are substituted or substituted with at least one R, or combinations thereof.

[0094] In some embodiments, n2 and n3 are each independently selected from 0 or 1; and / or n4 and n5 are each independently selected from 0 or 1; and / or n6 and n7 are each independently selected from 0 or 1; and / or n8 and n9 are each independently selected from 0 or 1.

[0095] In some embodiments, Ar4 is independently selected from groups (1-1) to (1-14):

[0096]

[0097] In some embodiments, the organic compound is selected from any of the following structures:

[0098]

[0099] Secondly, embodiments of this application also provide a method for preparing an organic compound, characterized by comprising the following steps:

[0100] The first compound and the second compound were mixed and reacted in solution to obtain the first intermediate;

[0101] A third compound is provided, and the third compound is mixed and reacted with the first intermediate to obtain a first organic compound;

[0102] A halogenated reagent is provided, and the halogenated reagent is mixed with the first organic compound and reacted to obtain a second intermediate;

[0103] A fourth compound is provided, and the fourth compound is mixed and reacted with the second intermediate to obtain the organic compound;

[0104] The first compound has the structure shown in general formula (2) below:

[0105]

[0106] In this context, Ar1 is independently selected each time it appears from an aryl group having 6 to 30 unsubstituted or substituted ring atoms with at least one R3, or a heteroaryl group having 5 to 30 unsubstituted or substituted ring atoms with at least one R3, or a combination of these groups; the heteroatoms in the heteroaryl group are independently selected from one or more of N, S, O, P, and Si, and the number of heteroatoms in the heteroaryl group is independently selected from 1 to 20; R3 is independently selected each time it appears from a D, C1 to C20 aliphatic chain hydrocarbon group, C1 to C20 aliphatic chain hydroxyl group, aliphatic cyclic hydrocarbon group having 3 to 30 ring atoms, aliphatic heterocyclic hydrocarbon group having 3 to 30 ring atoms, aryl group having 6 to 30 ring atoms, heteroaryl group having 5 to 60 ring atoms, and -NR. N1 R N2 , halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, or aldehyde, or combinations of these groups; R N1 and R N2 The groups are independently selected from H, D, C1-C20 aliphatic chain hydrocarbon groups, C1-C20 aliphatic chain hydroxyl groups, aliphatic cyclic hydrocarbon groups with 3 to 30 ring atoms, aliphatic heterocyclic hydrocarbon groups with 3 to 30 ring atoms, aryl groups with 6 to 30 ring atoms, or heteroaryl groups with 5 to 30 ring atoms, or combinations of these groups; R m Selected from halogens;

[0107] The second compound has the structure shown in the following general formula (3):

[0108]

[0109] R n Each time it appears, it is independently selected from at least one hydroxyl-substituted C1-C30 aliphatic chain hydrocarbon group, C1-C30 aliphatic chain hydrocarbon oxygen group, or hydroxyl group; Re Selected from hydroxyl, amino, or thiol groups; two R groups n They may form rings or not;

[0110] The third compound is selected from malononitrile;

[0111] The halogenated reagent includes one or more of N-bromosuccinimide, N-iodosuccinimide, liquid bromine, iodine powder, and chlorine water;

[0112] The fourth compound includes compounds having the following structure:

[0113]

[0114] In this case, X is selected independently from CR each time it appears. x1 Or N;

[0115] Z1 and Z2 are each selected independently from NR each time they appear. x2 CR x3 CR x4 R x5 , O or S;

[0116] Z3 is selected independently from NH or NR each time it appears. 10 ;

[0117] R x1 R x2 R x3 R x4 and R x5 Each time it appears, it is independently selected from D, a substituted or at least R-substituted C1-C30 aliphatic chain hydrocarbon group, a substituted or at least R-substituted aliphatic cyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted aliphatic heterocyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted C1-C30 aliphatic hydrocarbon oxy group, a substituted or at least R-substituted C1-C30 aliphatic hydrocarbon thiol group, a substituted or at least R-substituted C1-C30 aliphatic hydrocarbon amino group, or a substituted or at least R-substituted aryl group having 6 to 30 ring atoms, or a combination of these groups; any two adjacent Rs x1 They can be connected to form a loop or not;

[0118] R4, R5, R6, R7, R8 and R9, each time appearing independently, are selected from a substituted or at least R-substituted C1 to C30 aliphatic chain hydrocarbon group, a substituted or at least R-substituted aliphatic cyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted aliphatic heterocyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted C1 to C30 aliphatic hydrocarbon oxy group, a substituted or at least R-substituted C1 to C30 aliphatic hydrocarbon thiol group, or a substituted or at least R-substituted C1 to C30 aliphatic hydrocarbon amino group, or a combination of these groups.

[0119] R 10 Selected from substituted or C1-C30 chain alkylene groups, substituted or C1-C30 chain alkene groups, substituted or C1-C30 chain alkene groups, substituted or C1-C30 aryl groups with 6 to 30 ring atoms, substituted or C1-C30 heteroaryl groups with 5 to 30 ring atoms, or combinations of these groups.

[0120] n2 and n3 are each independently selected from integers from 0 to 5;

[0121] n4 and n5 are each independently selected from integers from 0 to 4;

[0122] n6 and n7 are each independently selected from integers from 0 to 4;

[0123] Each time R appears, it is independently selected from one or more of H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C30 alkyl, C1-C30 alkoxy, and aryl with 6-30 ring atoms.

[0124] In some embodiments, after obtaining the first organic compound, the structure of a fourth compound is further introduced into the structure of the first organic compound. By modifying the end groups on both sides of the first organic compound with the fourth compound, a second organic compound with a wider range of applications can be obtained.

[0125] In some embodiments, the step of obtaining the first intermediate specifically includes:

[0126] A first catalyst is provided, and a first compound, a second compound, and the first catalyst are mixed and reacted in solution; the first catalyst includes a palladium catalyst.

[0127] And / or, R x1 R x2 R x3 R x4 and R x5Each time it appears, it is independently selected from H, D, a substituted or at least R-substituted C1-C20 aliphatic chain hydrocarbon group, a substituted or at least R-substituted aliphatic cyclic hydrocarbon group having 3 to 20 ring atoms, a substituted or at least R-substituted aliphatic heterocyclic hydrocarbon group having 3 to 20 ring atoms, a substituted or at least R-substituted C1-C20 aliphatic hydrocarbon oxy group, a substituted or at least R-substituted C1-C20 aliphatic hydrocarbon thiol group, a substituted or at least R-substituted C1-C20 aliphatic hydrocarbon amino group, or a substituted or at least R-substituted aryl group having 6 to 20 ring atoms, or a combination of these groups; any two adjacent Rs x1 Benzene rings or naphthalene rings are connected to each other;

[0128] And / or, each of R4, R5, R6, R7, R8, and R9 is independently selected from substituted or at least R-substituted C1-C20 aliphatic hydrocarbon groups, substituted or at least R-substituted aliphatic cyclic hydrocarbon groups having 3 to 20 ring atoms, substituted or at least R-substituted aliphatic heterocyclic hydrocarbon groups having 3 to 20 ring atoms, substituted or at least R-substituted C1-C20 aliphatic hydrocarbon oxy groups, substituted or at least R-substituted C1-C20 aliphatic hydrocarbon thiol groups, or substituted or at least R-substituted C1-C20 aliphatic hydrocarbon amino groups; preferably, the fourth compound comprises one or more of compounds (1-1) to (1-14):

[0129]

[0130] Among them, R 11 Selected from halogens;

[0131] And / or, the step of obtaining the first intermediate specifically includes:

[0132] The first compound, the second compound, and the palladium catalyst were mixed and heated to obtain the initial product;

[0133] The primary product is mixed with the palladium catalyst and heated to obtain the first intermediate.

[0134] The palladium catalyst used before obtaining the primary product is different from the palladium catalyst used after obtaining the primary product.

[0135] And / or, the palladium catalyst is selected from one or more of tetra(triphenylphosphine)palladium, palladium trifluoroacetate, palladium acetate, dichlorodi(triphenylphosphine)palladium, and palladium dichloride, wherein the first palladium catalyst and the second palladium catalyst are different;

[0136] And / or, the molar ratio of the first compound to the second compound is 1:(2-4);

[0137] And / or, the molar ratio of the first intermediate to the third compound is 1:(2-6);

[0138] And / or, the molar ratio of the second intermediate to the fourth compound is 1:(2-4).

[0139] It should be noted that palladium catalysts refer to various catalysts made with metallic palladium as the main active component, using palladium or palladium salts supported on supports such as alumina and zeolites, and salts such as sodium, cadmium, and lead as co-catalysts. By selecting different palladium catalysts in the reactions before and after the preparation of the primary product, the purpose of catalyzing different reactions can be achieved.

[0140] In some specific embodiments, the step of obtaining the first intermediate specifically includes:

[0141] The first compound, the second compound, and the palladium catalyst were mixed and heated to obtain the initial product;

[0142] The primary product is mixed with the palladium catalyst and heated to obtain the first intermediate.

[0143] The palladium catalyst used before obtaining the primary product is different from the palladium catalyst used after obtaining the primary product.

[0144] And / or, the palladium catalyst is selected from one or more of tetra(triphenylphosphine)palladium, palladium trifluoroacetate, palladium acetate, dichlorodi(triphenylphosphine)palladium, and palladium dichloride, wherein the first palladium catalyst and the second palladium catalyst are different;

[0145] In some specific embodiments, the palladium catalyst used in the reaction step to obtain the initial product is palladium trifluoroacetate, palladium acetate, palladium dichlorobis(triphenylphosphine)dichloro, or palladium dichloride; the palladium catalyst used in the reaction step to obtain the first intermediate is tetra(triphenylphosphine)palladium.

[0146] In some embodiments, in the reaction step to obtain the initial product, the reaction temperature is 90–120°C and the reaction time is 12–24 h.

[0147] In the reaction step to obtain the first intermediate, the molar ratio of the initial product to the palladium catalyst is 1:(0.05~0.2), the reaction temperature is 120~150℃, and the reaction time is 10~24h;

[0148] In the reaction step to obtain the first organic compound, the reaction temperature is 20–60 °C and the reaction time is 1–6 h;

[0149] In the reaction step to obtain the second organic compound, the reaction temperature is 100–130 °C and the reaction time is 12–24 h.

[0150] In some specific embodiments, n2 and n3 may be independently selected from 0 or 1; and / or n4 and n5 may be independently selected from 0 or 1; and / or n6 and n7 may be independently selected from 0 or 1; and / or n8 and n9 may be independently selected from 0 or 1.

[0151] In some embodiments, R n Each time it appears, it is independently selected from a hydroxylated C1-C20 aliphatic chain hydrocarbon group, a C1-C20 aliphatic chain hydrocarbon oxygen group, or a hydroxyl group; when two Rs n When the radicals are selected from aliphatic chain hydrocarbons from C1 to C20, the two Rs... n Forming a ring.

[0152] Thirdly, embodiments of this application also provide a thin film comprising the organic compound as described above, or an organic compound prepared by the method described above. By using the above-described organic compound as a thin film material, a thin film with good hole mobility can be provided.

[0153] Fourthly, embodiments of this application also provide an optoelectronic device, comprising:

[0154] The first and second electrodes are arranged opposite to each other; and

[0155] Multiple functional layers are disposed between the first electrode and the second electrode;

[0156] The material of at least one of the multiple functional layers includes the organic compounds described above.

[0157] By using the aforementioned organic compounds as materials, or by using thin films containing the aforementioned organic compounds as functional layers, the maximum luminous brightness, lifespan, and luminous efficiency of optoelectronic devices are significantly improved, thereby comprehensively enhancing the luminous performance of optoelectronic devices.

[0158] By using the aforementioned organic compounds as hole functional layer materials, or by using thin films containing the aforementioned organic compounds as hole functional layers, the maximum luminous brightness, lifespan, and luminous efficiency of optoelectronic devices are significantly improved, thereby comprehensively enhancing the luminous performance of optoelectronic devices.

[0159] In some embodiments, the functional layer includes a hole functional layer, and the material of the hole functional layer includes organic compounds as described above;

[0160] Optionally, the hole functional layer includes a hole injection layer and a hole transport layer stacked together, wherein the hole injection layer is closer to the anode than the hole transport layer, and the material of the hole transport layer includes organic compounds as described above.

[0161] And / or, the functional layer includes an electronic functional layer, the material of which includes one or more of inorganic electronic functional materials and organic electronic functional materials. The inorganic electronic functional materials include one or more of first doped metal oxide particles, first undoped metal oxide particles, IIB-VIA group semiconductor materials, IIIA-VA group semiconductor materials and IB-IIIA-VIA group semiconductor materials. The organic electronic functional materials include one or more of quinoxaline compounds, imidazole compounds, triazine compounds, fluorene-containing compounds, hydroxyquinoline compounds, and fullerene derivatives.

[0162] And / or, the functional layer includes an excitation layer, the material of which includes one or more of single-structure quantum dots, core-shell quantum dots, and perovskite semiconductor materials. The materials of the single-structure quantum dots, the core material of the core-shell quantum dots, and the shell material of the core-shell quantum dots are each independently selected from one or more of group II-VI compounds, group IV-VI compounds, group III-V compounds, and group I-III-VI compounds. Group II-VI compounds include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, and ZnO. One or more of the following compounds: SeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and HgZnSTe; and group IV-VI compounds including SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe. One or more of PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, and SnPbSTe, and III-V compounds including GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, and GaAlNP. One or more of the following compounds are included: GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and InAlPSb; Group I-III-VI compounds include one or more of CuInS2, CuInSe2, and AgInS2; perovskite semiconductor materials include doped or undoped inorganic perovskite semiconductors or organic-inorganic hybrid perovskite semiconductors, with the general structural formula of inorganic perovskite semiconductors being AMX3, where A is Cs. + Ions, where M is a divalent metal cation, including Pb 2+ Sn 2+ Cu 2+ Ni2+ Cd 2+ Cr 2+ Mn 2+ Co 2+ Fe 2+ 、Ge 2+ Yb 2+ Eu 2+ One or more of them, where X is a halide anion, including Cl. - ,Br - I - One or more of the following; the general structural formula of organic-inorganic hybrid perovskite semiconductors is BMX3, where B is an organic amine cation, including CH3(CH2). n-2 NH3 + Or [NH3(CH2)] n NH3] 2+ Where n≥2, M is a divalent metal cation, including Pb 2+ Sn 2+ Cu 2+ Ni 2+ Cd 2+ Cr 2+ Mn 2+ Co 2+ Fe 2+ 、Ge 2+ Yb 2+ Eu 2+ One or more of them, where X is a halide anion, including Cl. - ,Br - I - One or more of them.

[0163] In some embodiments, the hole injection layer material includes 4,4'-N,N'-dicarbazolyl-biphenyl, poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine], N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4”-diamine, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine, poly(N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine), N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)spiro, N,N'-bis(4-(N,N'-diphenyl)benzidine), N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)spiro, N,N'-bis(4-(N,N'-diphenyl) (-amino)phenyl)-N,N'-diphenylbenzidine, 4,4',4'-tris(N-carbazolyl)-triphenylamine, 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, poly[(9,9'-dioctylfluorene-2,7-diyl)co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))], poly(N-vinylcarbazole) and its derivatives, N,N'-di(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4-4'-diamine, spiron NPB, poly(phenylenevinylene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene] [Base], poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene], 2,2',7,7'-tetratetra[N,N-di(4-methoxyphenyl)amino]-9,9'-spirodifluorene, 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline], 1,3-di(carbazole-9-yl)benzene, polyaniline, polypyrrole, poly(p)phenylenevinylene, aromatic tertiary amines, polynuclear aromatic tertiary amines, 4,4'-bis(p-carbazole)-1,1'-biphenyl compounds, N,N,N',N'-tetraarylbenzidine, PEDOT:PSS and its derivatives, polymethacrylates and their derivatives Derivatives, poly(9,9-octylfluorene) and its derivatives, poly(spirofluorene) and its derivatives, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene, PEDOT, PEDOT:PSS, PEDOT:PSS derivatives doped with s-MoO3, 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, tetracyanoquinone dimethane, doped graphene, undoped graphene, C60, copper phthalocyanine, the second doped metal oxide particles, the second undoped metal oxide particles, the metal sulfide and the metal nitride, or one or more of these.

[0164] By using the aforementioned organic compounds as hole functional layer materials, or by using thin films containing the aforementioned organic compounds as hole functional layers, the maximum luminous brightness, lifespan, and luminous efficiency of optoelectronic devices are significantly improved, thereby comprehensively enhancing the luminous performance of optoelectronic devices.

[0165] Fifthly, embodiments of this application also provide a method for fabricating an optoelectronic device, which includes the following steps:

[0166] A hole injection layer material is deposited on the first electrode to obtain a hole injection layer;

[0167] The above-mentioned organic compound is deposited on the hole injection layer to obtain the hole transport layer;

[0168] An excitation layer is prepared by depositing quantum dot material on the hole transport layer;

[0169] An electron transport layer material is deposited on the excitation layer to obtain an electron transport layer;

[0170] The material of the second electrode is deposited onto the modification layer by vapor deposition to obtain the second electrode.

[0171] Encapsulation.

[0172] In some embodiments, the method for fabricating optoelectronic devices may also be:

[0173] An electron transport layer material is deposited on the upper first electrode to obtain an electron transport layer.

[0174] A quantum dot material is deposited on the electron transport layer to form an excitation layer;

[0175] The above-mentioned organic compounds are deposited on the excitation layer to obtain a hole transport layer;

[0176] A hole injection layer material is deposited on the hole transport layer to form a hole injection layer;

[0177] The material of the second electrode is vapor-deposited onto the hole injection layer to obtain the second electrode.

[0178] Encapsulation.

[0179] The deposition method can be implemented using techniques well-known in the art, specifically:

[0180] The excitation layer can be generated using chemical vapor deposition, continuous ion layer adsorption and reaction, anodic oxidation, coprecipitation, and solution processing. Among these, chemical methods include, for example, chemical vapor deposition, continuous ion layer adsorption and reaction, anodic oxidation, electrolytic deposition, and coprecipitation.

[0181] Hole transport layers can be achieved using physical deposition methods, such as thermal evaporation deposition, electron beam evaporation deposition, magnetron sputtering, multi-arc ion deposition, physical vapor deposition, atomic layer deposition, and pulsed laser deposition. Solution processing methods include spin coating, printing, inkjet printing, blade coating, dip coating, immersion coating, spraying, roller coating, casting, slot coating, and strip coating.

[0182] Electron transport layers can be constructed using chemical vapor deposition, continuous ion layer adsorption and reaction, anodic oxidation, coprecipitation, and solution processing.

[0183] When the hole injection layer is an organic molecular compound, all the methods listed above can be used; when it is an inorganic molecular compound, solution processing can be used.

[0184] For specific processing methods and conditions, please refer to common practices in this field, which will not be elaborated here.

[0185] Sixthly, embodiments of this application also provide a display device, including the aforementioned optoelectronic devices. The display device can be any electronic product with display functionality, including but not limited to smartphones, tablets, laptops, digital cameras, digital camcorders, smart wearable devices, smart weighing scales, in-vehicle displays, televisions, or e-book readers. Smart wearable devices can be, for example, smart bracelets, smartwatches, virtual reality (VR) headsets, etc.

[0186] Organic compound Example 1

[0187] This application provides an organic compound and its preparation method. The synthetic route of the organic compound in this application is as follows:

[0188]

[0189] The preparation method of organic compounds includes the following steps:

[0190] S1. In a 100 mL two-necked reaction flask, add 30 mL of toluene, 1 mmol of compound M1-1 (CAS: 14348-75-5), 3 mmol of 3-mercaptophenylboronic acid (CAS: 352526-00-2), and 0.1 mmol of tetra(triphenylphosphine)palladium (CAS: 14221-01-3), and purge with nitrogen. Use a vacuum pump to purge the mixture with nitrogen for 15 minutes. Cover the two-necked reaction flask with aluminum foil to protect it from light, stir, and heat to 110 °C for 24 h. Stop the reaction and cool to 25 °C. Extract the reaction solution and wash repeatedly 3 to 4 times with 1000 mL of dichloromethane and 250 mL of water. Dry the organic phase with anhydrous magnesium sulfate. Perform crude separation by column chromatography with petroleum ether:dichloromethane:ethyl acetate (volume ratio 10:1:1) as the developing solvent. Finally, compound M1-2 is obtained with a yield of 68%.

[0191] S2. Add 30 mL of dimethyl sulfoxide (DMSO), 1 mmol of compound M1-2, and 0.2 mmol of palladium dichloride (CAS: 7647-10-1) to a 100 mL two-necked reaction flask. Purge with nitrogen and purge with a vacuum pump for 15 minutes. Stir the two-necked reaction flask and heat to 140 °C for 12 h. Stop the reaction and cool to 25 °C. Extract the reaction solution and wash repeatedly 3 to 4 times with 300 mL of dichloromethane and 20 mL of water. Dry the organic phase with anhydrous magnesium sulfate. Perform crude separation by column chromatography with petroleum ether:dichloromethane:ethyl acetate (volume ratio 25:1:1) as the developing solvent. The final product is compound M1-3 with a yield of 95%.

[0192] S3. Add 30 mL of toluene, 1 mmol of compound M1-3 and 2 mmol of malononitrile to a 100 mL two-necked reaction flask. Stir the reaction flask at 25 °C for 1 h, stop the reaction, and cool it down to 25 °C. Extract the reaction solution and perform crude separation by column chromatography to obtain the crude product.

[0193] S4. Add the crude product to 30 mL of chloroform solution. Dissolve 2 mmol of N-bromosuccinimide (NBS) in 10 mL of chloroform and add it dropwise to the reaction solution under ice bath conditions. After the addition is complete, continue stirring at 25 °C for 30 min. Extract the reaction solution and wash repeatedly 3 to 4 times with 1000 mL of dichloromethane and 250 mL of water. Dry the organic phase with anhydrous magnesium sulfate. Perform crude separation by column chromatography with petroleum ether:dichloromethane:ethyl acetate (volume ratio 20:1:1) as the developing solvent. Finally, compound M1-4 is obtained with a yield of 85%.

[0194] S5. In a 100 mL two-necked reaction flask, add 40 mL of toluene, 1 mmol of compound M1-4, 3 mmol of diphenylamine (CAS: 122-39-4), and 0.5 mmol of CuCl. Purge with nitrogen gas and purge for 15 minutes using a vacuum pump. Stop the reaction and cool to 25 °C. Extract the reaction solution, washing repeatedly 3-4 times with dichloromethane (1000 mL) and water (250 mL). Dry the organic phase with anhydrous magnesium sulfate. Perform crude separation using column chromatography with petroleum ether:dichloromethane:ethyl acetate (volume ratio 150:1:1) as the developing solvent. The final product is organic compound M1, with a yield of 70%. The NMR data for organic compound M1 are as follows:

[0195] 1 HNMR(500MHz,Chloroform-d)δ8.87(s,2H),8.74(s,2H),8.21-8.18(m,2H),7.85-7.8 2(m,2H),7.30-7.27(m,2H),7.27-7.23(m,8H),7.11-7.08(m,8H),7.05-7.01(m,4H).

[0196] Organic compound Example 2

[0197] The organic compound and its preparation method provided in this application differ from those in Organic Compound Example 1 in that:

[0198] Replace the molar ratio of compound M1-1 and 3-mercaptophenylboronic acid in step S1 with 1 mmol: 4 mmol, and replace "stir the two-necked reaction flask with tin foil to protect it from light and heat it to 110°C for 24 h" in step S1 with "stir the two-necked reaction flask with tin foil to protect it from light and heat it to 90°C for 12 h".

[0199] Replace "stir the two-necked reaction flask and heat it to 140°C for 12 hours" in step S2 with "stir the two-necked reaction flask and heat it to 120°C for 10 hours".

[0200] Replace NBS in step S4 with liquid bromine;

[0201] In step S5, the diphenylamine was replaced with 2,2-dinaphthylamine (CAS: 532-18-3). Organic compound M2 was obtained, and its NMR data are as follows:

[0202] 1HNMR(500MHz,Chloroform-d)δ9.44(s,2H),9.24(s,2H),8.40-8.36(m,2H),7.80-7.76(m,6H),7.74-7.7 1(m,4H),7.50-7.48(m,4H),7.47-7.45(m,2H),7.37-7.28(m,8H),7.27-7.24(m,4H),7.21-7.19(m,4H).

[0203] Organic compound Example 3

[0204] The organic compound and its preparation method provided in this application differ from those in Organic Compound Example 1 in that:

[0205] Replace the molar ratio of compound M1-1 and 3-mercaptophenylboronic acid in step S1 with 1 mmol: 2 mmol, and replace "stir the two-necked reaction flask in the dark with tin foil and heat it to 110°C for 24 h" in step S1 with "stir the two-necked reaction flask in the dark with tin foil and heat it to 120°C for 24 h".

[0206] Replace “stir the two-necked reaction flask and heat it to 140°C for 12 hours” in step S2 with “stir the two-necked reaction flask and heat it to 150°C for 12 hours”.

[0207] Replace NBS with NIS in step S4;

[0208] In step S5, the diphenylamine was replaced with N,N-diphenylnaphth-2-amine (CAS: 6940-30-3). Organic compound M3 was obtained, and its NMR data are as follows:

[0209] 1 HNMR(500MHz,Chloroform-d)δ9.59(s,2H),9.31(s,2H),8.81-8.78(m,2H),8.14-8.10(m,2H),7.83-7.79(m,4H), 7.77-7.71(m,12H),7.66-7.62(m,2H),7.44-7.43(m,4H),7.42-7.39(m,4H),7.37-7.28(m,8H),6.99-6.95(m,4H).

[0210] Organic compound Example 4

[0211] This application provides an organic compound and its preparation method, which differs from Organic Compound Example 1 in that: the molar ratio of compound M1-2 to palladium dichloride in step S2 is replaced with 1 mmol:0.05 mmol; CuCl in step S5 is replaced with CuI; and diphenylamine in step S4 is replaced with phenoxathia-2-boronic acid (CAS: 2304440-01-3). Organic compound M4 is obtained, and its NMR data are as follows: 1 HNMR(500MHz,Chloroform-d)δ8.96-8.93(m,2H),8.81-8.79(m,2H),8.46-8.43(m,2H),8.29-8.25(m,2H),8.07-8.03(m,2H),7.6 8-7.65(m,2H),7.44-7.39(m,2H),7.31-7.27(m,2H),7.13-7.10(m,2H),7.10-7.08(m,2H),7.05-7.01(m,2H),7.00-6.98(m,2H).

[0212] Organic compound Example 5

[0213] This application provides an organic compound and its preparation method, which differs from Organic Compound Example 1 in that: the molar ratio of compound M1-2 to palladium dichloride in step S2 is replaced with 1 mmol:0.1 mmol; and the diphenylamine in step S5 is replaced with 10-(4-boronic acid phenyl)-10H-phenoxazine (CAS: 1246021-62-4). Organic compound M5 is obtained, and its NMR data are as follows:

[0214] 1 HNMR(500MHz,Chloroform-d)δ9.58-9.57(m,2H),9.37-9.36(m,2H),8.55-8.54(m,2H),8.4 3-8.40(m,2H),7.57-7.54(m,2H),7.43-7.40(m,4H),7.21-7.17(m,4H),7.03-6.92(m,16H).

[0215] Organic compound Example 6

[0216] The organic compound and its preparation method provided in this application differ from those in Organic Compound Example 1 in that:

[0217] Replace the molar ratio of compound M1-3 and malononitrile in step S3 with 1 mmol: 6 mmol;

[0218] In step S5, the diphenylamine was replaced with 9-(4-boronic acid phenyl)-9H-carbazole (CAS: 419536-33-7). Organic compound M6 was obtained, and its NMR data are as follows:

[0219] 1 HNMR(500MHz,Chloroform-d)δ8.95-8.94(m,2H),8.81-8.79(m,2H),8.48-8.45(m,2H),8.26-8.23(m,2H),8.16-8.12(m ,4H),8.06-8.02(m,2H),7.77-7.74(m,4H),7.63-7.58(m,4H),7.43-7.39(m,4H),7.35-7.30(m,6H),7.27-7.22(m,2H).

[0220] Organic compound Example 7

[0221] The organic compound and its preparation method provided in this application differ from those in Organic Compound Example 1 in that:

[0222] Replace the molar ratio of compound M1-3 and malononitrile in step S3 with 1 mmol: 4 mmol;

[0223] In step S5, the diphenylamine was replaced with bis(4-boronicophenyl)-4-methoxy-N-(4-methylbenzene)aniline (CAS: 201802-29-1). Organic compound M7 was obtained, and its NMR data are as follows:

[0224] 1 HNMR(500MHz,Chloroform-d)δ8.95-8.93(m,2H),8.80-8.79(m,2H),8.43-8.42(m,2H),8.25-8.21(m,2H),8 .02-7.98(m,2H),7.59-7.56(m,4H),7.28-7.25(m,4H),7.13-7.10(m,8H),6.85-6.81(m,8H),3.78(s,12H).

[0225] Organic compound Example 8

[0226] The organic compound and its preparation method provided in this application differ from those in Organic Compound Example 1 in that:

[0227] In step S5, diphenylamine was replaced with 2-bromodibenzothiophene (CAS: 108847-24-1), and the molar ratio of compound M1-4 to 2-bromodibenzothiophene was set to 1 mmol: 8 mmol.

[0228] Replace "stir the reaction flask with tin foil to protect it from light and heat it to 105℃ for 20 h" in step S5 with "stir the reaction flask with tin foil to protect it from light and heat it to 100℃ for 12 h"; the organic compound M8 is obtained, and the NMR data are as follows:

[0229] 1 HNMR(500MHz,Chloroform-d)δ8.60-8.58(m,2H),8.44-8.42(m,2H),8.35-8.33(m,2H),8.31-8.28(m ,2H),8.24-8.18(m,4H),8.16-8.12(m,2H),7.92-7.89(m,2H),7.71-7.67(m,4H),7.53-7.45(m,4H).

[0230] Organic compound Example 9

[0231] The organic compound and its preparation method provided in this application differ from those in Organic Compound Example 1 in that:

[0232] In step S5, the diphenylamine was replaced with 10-(4-boronic acid phenyl)-10H-phenthiazine (CAS: 1246021-63-5), and the molar ratio of compound M1-4 and 10-(4-boronic acid phenyl)-10H-phenthiazine was set to 1 mmol: 9 mmol.

[0233] Replace "stir the reaction flask in the dark with tin foil and heat to 105℃ for 20h" in step S5 with "stir the reaction flask in the dark with tin foil and heat to 130℃ for 24h"; the organic compound M9 is obtained, and the NMR data are as follows:

[0234] 1 HNMR(500MHz,Chloroform-d)δ8.60-8.58(m,2H),8.44-8.42(m,2H),8.37-8.35(m,2H),8.3 0-8.27(m,2H),7.64-7.59(m,6H),7.43-7.31(m,12H),7.26-7.21(m,4H),7.18-7.15(m,4H).

[0235] Organic Compound Example 10

[0236] The organic compound and its preparation method provided in this application differ from those in Organic Compound Example 1 in that:

[0237] Replace tetra(triphenylphosphine)palladium in step S1 with triphenylarsine; replace palladium dichloride in step S2 with palladium trifluoroacetate; omit steps S4 and S5; the organic compound M10 is obtained, and its NMR data are as follows:

[0238] 1 HNMR(500MHz,Chloroform-d)δ8.56(s,2H),8.40(s,2H),8.24-8.20(m,2H),7.92-7.89(m,2H),7.52-7.44(m,4H).

[0239] Organic compound Example 11

[0240] This application provides an organic compound and its preparation method, which differs from Organic Compound Example 1 in that: compound M1-1 in step S1 is replaced with 3-bromobenzofluorenone (CAS: 1674334-51-0); DMSO in step S2 is replaced with N,N-dimethylformamide (DMF); and steps S4 and S5 are omitted. Organic compound M11 is obtained, and its NMR data are as follows:

[0241] 1 HNMR(500MHz,Chloroform-d)δ8.77(s,1H),8.50(s,1H),8.45(s,1H),8.32(d,J=2.3 Hz,1H),8.25-8.19(m,3H),8.18-8.13(m,1H),7.93-7.88(m,2H),7.53-7.44(m,4H).

[0242] Organic compound Example 12

[0243] This application provides an organic compound and its preparation method, which differs from Organic Compound Example 1 in that: compound M1-1 in step S1 is replaced with 12H-dibenzo[B,H]fluorene-12-one (CAS: 53223-75-9); steps S4 and S5 are omitted. Organic compound M12 is obtained, and its NMR data are as follows:

[0244] 1 HNMR(500MHz,Chloroform-d)δ8.50-8.46(m,4H),8.31-8.28(m,4H),8.24-8.20(m,2H),7.92-7.89(m,2H),7.52-7.44(m,4H).

[0245] Organic compound Example 13

[0246] The organic compound and its preparation method provided in this application differ from those in Organic Compound Example 1 in that: the 3 mmol of 3-mercaptophenylboronic acid in step S1 is replaced with 1.5 mmol of 3-mercaptophenylboronic acid and 1.5 mmol of 2-(4,4,5,5-tetramethyl-1,3,2-dihexopentiborane-2-yl)phenol (CAS: 269409-97-4); steps S4 and S5 are omitted. Organic compound M13 is obtained, and its NMR data are as follows: 1 HNMR(500MHz,Chloroform-d)δ8.55(s,1H),8.43(s,1H),8.24-8.20(m,2H),8.01-7.9 7(m,1H),7.93-7.88(m,2H),7.59-7.56(m,1H),7.53-7.45(m,3H),7.41-7.35(m,1H).

[0247] Organic compound Example 14

[0248] This application provides an organic compound and its preparation method, which differs from Organic Compound Example 1 in that: 3-mercaptophenylboronic acid in step S1 is replaced with 2-(4,4,5,5-tetramethyl-1,3,2-diaxopentabolane-2-yl)phenol (CAS: 269409-97-4); steps S4 and S5 are omitted. Organic compound M14 is obtained, and its NMR data are as follows:

[0249] 1 HNMR(500MHz,Chloroform-d)δ8.21(s,2H),8.00-7.97(m,4H),7.59-7.55(m,2H),7.50-7.45(m,2H),7.41-7.35(m,2H).

[0250] Organic Compound Example 15

[0251] This application provides an organic compound and its preparation method, which differs from Organic Compound Example 1 in that: 3-mercaptophenylboronic acid in step S1 is replaced with 2-aminophenylboronic acid (CAS: 5570-18-3); steps S4 and S5 are omitted. Organic compound M15 is obtained, and its NMR data are as follows:

[0252] 1 HNMR(500MHz,Chloroform-d)δ9.79(s,2H),8.57(s,2H),8.18-8.11(m,4H),7.62-7.58(m,2H),7.30-7.19(m,4H).

[0253] Organic compound Example 16

[0254] This application provides an organic compound and its preparation method, which differs from Organic Compound Example 1 in that: 3-mercaptophenylboronic acid in step S1 is replaced with 2-aminophenylboronic acid (CAS: 5570-18-3); step S4 is omitted; and diphenylamine in step S5 is replaced with 1-chlorobenzene (CAS: 108-90-7). Organic compound M16 is obtained, and its NMR data are as follows:

[0255] 1 HNMR(500MHz,Chloroform-d)δ8.31(s,2H),8.26(s,2H),8.23-8.20(m,2H), 7.72-7.69(m,2H),7.51-7.46(m,4H),7.42-7.33(m,8H),7.31-7.27(m,2H).

[0256] Organic compound comparative example 1

[0257] This application provides an organic compound and its preparation method in a comparative example. The synthetic route of the organic compound in this application is as follows:

[0258]

[0259] The preparation method of organic compounds includes the following steps:

[0260] S1. Add 30 mL of toluene, 2 mmol of compound M1-1 (CAS: 14348-75-5), and 2 mmol of malononitrile to a 100 mL two-necked reaction flask. Stir the reaction flask at 25 °C for 1 h, stop the reaction, and cool the temperature to 25 °C. Extract the reaction solution and perform crude separation by column chromatography. The developing solvent is petroleum ether:dichloromethane:ethyl acetate (volume ratio 20:1:1). The final product is organic compound P1-2 with a yield of 96%.

[0261] S2. Add 30 mL of toluene, 1 mmol of organic compound P1-2, and 2 mmol of malononitrile to a 100 mL two-necked reaction flask. Stir the reaction flask at 25 °C for 1 h, stop the reaction, and cool to 25 °C. Extract the reaction solution and perform crude separation using column chromatography. The NMR data of organic compound P1 are as follows: 1 HNMR(500MHz,Chloroform-d)δ7.98-7.96(m,2H),7.65-7.64(m,2H),7.33-7.29(m,8H),7.21-7.17(m,8H),7.12-7.04(m,6H).

[0262] Organic compound comparative example 2

[0263] The organic compound and its preparation method provided in this application differ from the organic compound comparative example 1 in that: in step S2, diphenylamine is replaced with 4-phenylboronic acid-9H-carbazole (CAS:419536-33-7).

[0264] The organic compound P2 was obtained, with the following structural formula:

[0265]

[0266] The NMR data for organic compound P2 are as follows:

[0267] 1 HNMR(500MHz,Chloroform-d)δ8.39-8.37(m,2H),8.18-8.15(m,2H),8.11-8.08(m ,4H),7.71-7.67(m,10H),7.47-7.43(m,4H),7.37-7.33(m,4H),7.30-7.26(m,4H).

[0268] Organic compound comparative example 3

[0269] The organic compound and its preparation method provided in this application differ from the organic compound comparative example 1 in that: in step S2, diphenylamine is replaced with 4-10H-benzoxazine-10-phenylboronic acid (CAS:1246021-62-4).

[0270] The organic compound P3 was obtained, with the following structural formula:

[0271]

[0272] The NMR data for organic compound P3 are as follows:

[0273] 1 HNMR(500MHz,Chloroform-d)δ8.39-8.37(m,2H),8.18-8.15(m,2H),7.71-7.67(m,6H),7.34-7.29(m,4H),7.24-7.17(m,12H),6.96-6.89(m,4H).

[0274] Organic compound comparative example 4

[0275] The organic compound and its preparation method provided in this application differ from organic compound comparative example 1 in that: compound M1-1 in step S1 is replaced with 3-bromofluorene-9-one (CAS:2041-19-2);

[0276] Replace step S2 with: add 30 mL of toluene, 1 mmol of compound 3-bromofluorene-9-one, 3 mmol of 2-(4,4,5,5-tetramethyl-1,3,2-diaxopentabolane-2-yl)phenol (CAS: 269409-97-4), and 0.1 mmol of tetra(triphenylphosphine)palladium (CAS: 14221-01-3) to a 100 mL two-necked reaction flask, and purge with nitrogen. Use a vacuum pump to evacuate the flask for 15 minutes to purge with nitrogen. Cover the two-necked reaction flask with aluminum foil to protect it from light, stir, and heat to 110 °C for 24 h. Stop the reaction and cool to 25 °C to obtain organic compound P4.

[0277] The structural formula of organic compound P4 is:

[0278]

[0279] The NMR data for organic compound P4 are as follows:

[0280] 1 HNMR(500MHz,Chloroform-d)δ8.33(s,1H),8.01-7.97(m,1H),7.96(s,1H), 7.83-7.79(m,2H),7.59-7.51(m,3H),7.50-7.45(m,1H),7.40-7.35(m,1H).

[0281] Thin film examples and characterization

[0282] The following specific examples illustrate in detail the method for preparing thin films using the organic compounds described in this application.

[0283] Taking the preparation method of thin film using organic compound M1 as the thin film material as an example, and the prepared thin film is referred to as "Thin Film Example 1", the preparation method of Thin Film Example 1 includes the following steps:

[0284] S1. Provide a substrate and spin-coat an organic compound M1 onto it at a speed of 3000 r / min for 30 seconds. After spin-coating, anneal the substrate in a glove box at a temperature of 120°C for 10 minutes to obtain a thin film.

[0285] Thin film Examples 2-16 and Thin film Comparative Examples 1-4

[0286] The difference between the thin film preparation methods in Thin Film Examples 2-16 and Thin Film Comparative Examples 1-4 and Thin Film Example 1 is that the organic compound M1 in step S1 is replaced with organic compound M2-organic compound M16 and organic compound P1-organic compound P4.

[0287] It is understood that in the preparation methods of the above-mentioned thin film Examples 2-16 and Thin film Comparative Examples 1-4, all experimental conditions are the same except for the thin film materials.

[0288] Thin film performance testing

[0289] The hole mobility of the above-mentioned thin film was tested using the following method: the hole mobility of the hole transport material was recorded using the space charge confinement current method, which can be described by the Mott-Gurney equation: J = 9με0ε r V 2 / (8d 3 );

[0290] Where J is the current density, μ is the hole mobility, and ε0 is the vacuum permittivity (8.85 × 10⁻⁶). -12 F / m), ε r V is the dielectric constant of the material, V is the applied bias voltage, and d is the film thickness; the structure of the device used for hole mobility testing is: anode (material is ITO) / thin film / light-emitting layer (material is CdZnSe) / electron transport layer (material is ZnMgO) / cathode (material is Ag);

[0291] Furthermore, in the hole mobility test described above, the device was placed in a sealed environment at 80°C for 100 hours, and the change in hole mobility after placement at 80°C was recorded, and the mobility decay rate was calculated; the test results are shown in Table 1.

[0292] Table 1

[0293]

[0294]

[0295] As shown in Table 1:

[0296] Compared with comparative examples 1-4, the thin film examples 1-16 all showed significant improvements in hole mobility to varying degrees, and the mobility decay was reduced under high temperature and high humidity conditions, indicating that the thin films using the above-mentioned organic compounds have high hole mobility and good heat resistance.

[0297] Compared to Thin Film Examples 10-16, Thin Film Examples 1-9 show a slight improvement in hole mobility and mobility decay. This is because end groups were further added to the organic compound used in Thin Film Example 10.

[0298] Fabrication and characterization of QLED devices

[0299] The following detailed examples illustrate the fabrication method of QLED devices using the organic compounds described in this application.

[0300] Taking the fabrication method of QLED devices using organic compound M1 as the hole transport layer material as an example, and the prepared QLED device is referred to as "Optoelectronic Device Example 1", the structure of Optoelectronic Device Example 1 is as follows. Figure 1 As shown, the fabrication method of the optoelectronic device in Example 1 includes the following steps:

[0301] S1. Place the ITO glass slide in a glass dish containing an ethanol solution, and sonicate it with acetone, deionized water, and ethanol for 20 minutes each in sequence, then dry it with a nitrogen gun; then place the cleaned ITO glass slide in oxygen plasma for 10 minutes; continue to treat the surface of the ITO substrate with ultraviolet-ozone for 15 minutes to obtain anode 1.

[0302] S2. Spin-coat the cleaned ITO glass slides with a thickness of 25nm onto PEDOT:PSS in air at a speed of 5000r / min for 30 seconds. After spin-coating, place them in air for annealing at a temperature of 150℃ for 30 minutes to obtain a hole injection layer 2 with a thickness of 40nm.

[0303] S3. Spin-coat organic compound M1 onto the hole transport layer at a speed of 3000 r / min for 30 seconds. After spin-coating, anneal in a glove box at a temperature of 120℃ for 10 minutes to obtain hole transport layer 3.

[0304] S4. Spin-coat 20 mg / mL CdZnSe quantum dot material onto the luminescent layer at a spin speed of 2000 r / min for 30 seconds; then... -2 After standing for 15 minutes under MPa, an excitation layer 4 with a thickness of 30 nm was obtained;

[0305] S5. Spin-coat ZnMgO (30 mg / mL) onto the luminescent layer at 3000 r / min for 30 seconds, then... -2 After standing for 15 minutes under MPa, electron transport layer 5 was obtained;

[0306] S6. Through thermal evaporation, the vacuum degree is less than or equal to 33*10. -4 Pa, Ag was vaporized at a rate of 1 angstrom / second for 200 seconds to form a top silver electrode with a thickness of 20 nm on the electron transport layer, resulting in cathode 6, which was then encapsulated with epoxy resin.

[0307] Example 1 of the preparation of optoelectronic devices.

[0308] Furthermore, referring to the preparation method of optoelectronic device Example 1, organic compounds M2-M16 and organic compounds P1-P4 were used as hole transport layer materials in the optoelectronic device, respectively, to prepare optoelectronic devices Examples 2-16 and Comparative Examples 1-4. It can be understood that, except for the hole transport layer materials, all other experimental conditions were the same.

[0309] In this application, the characteristics of optoelectronic devices in Examples 2-16 and Comparative Examples 1-4 are characterized, and the L values ​​corresponding to the above devices are measured. max (cd / m 2 ), measured lifetime T95, CE decay rate, luminous efficiency CE (cd / A) and T95 lifetime (1000nit);

[0310] The test method for lifetime T95@1000nit is as follows: Under constant current or voltage drive, the time required for the brightness of the device to decrease to a certain percentage of its maximum brightness is defined as T95. This lifetime is the measured lifetime. To shorten the testing cycle, device lifetime testing is usually performed at high brightness by accelerating device aging, and the lifetime at high brightness is obtained by fitting the extended exponential decay brightness decay fitting formula. For example, the lifetime at 1000nit is measured as T95@1000nit. The specific calculation formula is as follows:

[0311]

[0312] Among them, T95 L For longer lifespan at low brightness, T95 H For the measured lifetime under high brightness, L H To accelerate the device to its maximum brightness, L L The value is 1000 nits, and A is the acceleration factor.

[0313] The method for testing heat resistance performance is as follows: the initial current efficiency (CE) of optoelectronic devices in Examples 2-16 and Comparative Examples 1-4 is tested, the initial data is recorded, and then the devices are placed in a closed environment at 80°C for 100 hours. The CE values ​​after placement at 80°C and 80% humidity are recorded, and the CE decay rate is calculated. The above results are shown in Table 2.

[0314] Table 2

[0315]

[0316] As shown in Table 2:

[0317] Compared with comparative examples 1-4, optoelectronic devices 1-16 show significant improvements in maximum brightness, T95, T95@1000nit, and current efficiency to varying degrees. Furthermore, the current decay rate is reduced under high temperature and high humidity conditions, indicating that using organic compounds with specific structures as hole transport layer materials can improve the luminescence performance of the devices in multiple ways.

[0318] Compared to optoelectronic device examples 10-16, optoelectronic device examples 1-9 show slight improvements in all the above-mentioned performance tests. This is because end groups were further added to the organic compound used in optoelectronic device example 10.

[0319] The embodiments of this application have been described in detail above. Specific examples have been used to illustrate the principles and implementation methods of this application. The description of the above embodiments is only for the purpose of helping to understand the method and core ideas of this application. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of this application. Therefore, the content of this specification should not be construed as a limitation of this application.

Claims

1. An organic compound, characterized in that, It has a structure as shown in general formula (1): Among them, R1, R x Each group is independently selected from one or more of the following: cyano, halogen, carboxyl, nitro, sulfonic acid, mercapto, aldehyde, or C1-C30 aliphatic hydrocarbon groups substituted with at least one R2. Each time Ar1 appears, it is independently selected from aryl groups having 6 to 60 unsubstituted or substituted ring atoms with at least one R3, or heteroaryl groups having 5 to 60 unsubstituted or substituted ring atoms with at least one R3, or combinations of these groups; the heteroatoms in the heteroaryl groups are independently selected from one or more of N, S, O, P and Si. Ar2 and Ar3 are each independently selected from the following groups: Where Y is independently selected from NR y S or O; Ar4 is independently selected from unsubstituted or substituted Ar4 groups. z Substituted C1–C30 aliphatic chain hydrocarbon groups, unsubstituted or substituted with at least one R z The substituted aliphatic cyclic hydrocarbon group having 3 to 30 substituted ring atoms, either unsubstituted or substituted with at least one R z The substituted aliphatic heterocyclic hydrocarbon group having 3 to 30 ring atoms, either unsubstituted or substituted with at least one R z Substituted C1–C30 aliphatic chain alkyl oxygen, unsubstituted or substituted with at least one R z Substituted C1–C30 aliphatic chain hydrocarbon thiol group, unsubstituted or substituted with at least one R z Substituted C1–C30 aliphatic chain alkyl amino groups, unsubstituted or substituted with at least one R z The substituted aryl group has 6 to 60 cyclic atoms, and is either unsubstituted or substituted with at least one R group. z The substituted aryloxy group has 6 to 60 cyclic atoms, and is either unsubstituted or substituted with at least one R. z The substituted arylamino group has 6 to 60 ring atoms, and is either unsubstituted or substituted with at least one R. z The substituted aryl mercapto group has 6 to 60 cyclic atoms, and is either unsubstituted or substituted with at least one R group. z The substituted heteroaryl group has 5 to 60 cyclic atoms, is unsubstituted, or is substituted with at least one R z The substituted heteroaryl groups having 5 to 60 cyclic atoms, are either unsubstituted or substituted with at least one R z The substituted heteroarylamino group has 5 to 60 ring atoms, or is unsubstituted or has at least one R z The substituted ring atoms are heteroaryl mercapto groups with a ring number of 5 to 60, or combinations of these groups; R y Each occurrence is independently selected from H, D, unsubstituted, or by at least one R. w Substituted C1–C30 aliphatic chain hydrocarbon groups, unsubstituted or substituted with at least one R w The substituted aliphatic cyclic hydrocarbon group having 3 to 30 substituted ring atoms, either unsubstituted or substituted with at least one R w The substituted aliphatic heterocyclic hydrocarbon group having 3 to 30 ring atoms, either unsubstituted or substituted with at least one R w Substituted C1–C30 aliphatic hydrocarbon hydroxyl groups, unsubstituted or substituted with at least one R w Substituted C1-C30 alkyl mercapto groups, unsubstituted or with at least one R w The substituted ring atoms are 6 to 60 aryl groups, unsubstituted or substituted with at least one R group. w The substituted ring atoms are 6 to 60 aryloxy groups, unsubstituted or substituted with at least one R group. w The substituted heteroaryl group has 5 to 60 cyclic atoms, or is unsubstituted or has at least one R group. w The substituted heteroaryloxy group has a ring atom number of 5 to 60, or a combination of these groups; R2, R3, R z and R w Each occurrence is independently selected from D, C1-C30 aliphatic chain hydrocarbon groups, C1-C30 aliphatic chain hydroxyl groups, aliphatic cyclic hydrocarbon groups with 3 to 30 ring atoms, aliphatic heterocyclic hydrocarbon groups with 3 to 30 ring atoms, aryl groups with 6 to 30 ring atoms, heteroaryl groups with 5 to 30 ring atoms, and -NR. N1 R N2 , halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, or aldehyde, or combinations of these groups; R N1 and R N2 The aliphatic chain hydrocarbon group selected independently from H, D, C1 to C30, aliphatic chain hydrocarbon oxygen group selected from C1 to C30, aliphatic cyclic hydrocarbon group with 3 to 30 ring atoms, aliphatic heterocyclic hydrocarbon group with 3 to 30 ring atoms, aryl group with 6 to 30 ring atoms, or heteroaryl group with 5 to 30 ring atoms. Each occurrence of n1 is an independent integer from 0 to 6; # represents the fusion site.

2. The organic compound according to claim 1, characterized in that, Each time Ar4 appears, it is independently selected from one or more of the following groups: In this case, X is selected independently from CR each time it appears. x1 Or N; Z1 and Z2 are each selected independently from NR each time they appear. x2 CR x3 CR x4 R x5 , O or S; Each occurrence of Z3 is independently selected from either N-* or NR. 10 -*; R x1 R x2 R x3 R x4 and R x5 Each time it appears, it is independently selected from D, a substituted or at least R-substituted C1-C30 aliphatic chain hydrocarbon group, a substituted or at least R-substituted aliphatic cyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted aliphatic heterocyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted C1-C30 aliphatic hydrocarbon oxy group, a substituted or at least R-substituted C1-C30 aliphatic hydrocarbon thiol group, a substituted or at least R-substituted C1-C30 aliphatic hydrocarbon amino group, or a substituted or at least R-substituted aryl group having 6 to 30 ring atoms, or a combination of these groups; any two adjacent Rs x1 They can be connected to form a loop or not; R4, R5, R6, R7, R8 and R9, each time appearing independently, are selected from a substituted or at least R-substituted C1 to C30 aliphatic chain hydrocarbon group, a substituted or at least R-substituted aliphatic cyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted aliphatic heterocyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted C1 to C30 aliphatic hydrocarbon oxy group, a substituted or at least R-substituted C1 to C30 aliphatic hydrocarbon thiol group, or a substituted or at least R-substituted C1 to C30 aliphatic hydrocarbon amino group, or a combination of these groups. R 10 Selected from substituted or C1-C30 chain alkylene groups, substituted or C1-C30 chain alkene groups, substituted or C1-C30 chain alkene groups, substituted or C1-C30 aryl groups with 6 to 30 ring atoms, substituted or C1-C30 heteroaryl groups with 5 to 30 ring atoms, or combinations of these groups. n2 and n3 are each independently selected from integers from 0 to 5; n4 and n5 are each independently selected from integers from 0 to 4; n6 and n7 are each independently selected from integers from 0 to 4; When n2, n3, n4, n5, n6, and n7 are each independently selected from integers greater than or equal to 2, any two adjacent R4s can be connected to each other to form a cycle or not; any two adjacent R5s can be connected to each other to form a cycle or not; any two adjacent R6s can be connected to each other to form a cycle or not; any two adjacent R7s can be connected to each other to form a cycle or not; any two adjacent R8s can be connected to each other to form a cycle or not; any two adjacent R9s can be connected to each other to form a cycle or not. Each time R appears, it is independently selected from one or more of H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C30 alkyl, C1-C30 alkoxy, and aryl with 6-30 ring atoms; * indicates a connection point.

3. The organic compound according to claim 2, characterized in that, R x1 R x2 R x3 R x4 and R x5 Each time it appears, it is independently selected from H, D, a substituted or at least R-substituted C1-C20 aliphatic chain hydrocarbon group, a substituted or at least R-substituted aliphatic cyclic hydrocarbon group having 3 to 20 ring atoms, a substituted or at least R-substituted aliphatic heterocyclic hydrocarbon group having 3 to 20 ring atoms, a substituted or at least R-substituted C1-C20 aliphatic hydrocarbon oxy group, a substituted or at least R-substituted C1-C20 aliphatic hydrocarbon thiol group, a substituted or at least R-substituted C1-C20 aliphatic hydrocarbon amino group, or a substituted or at least R-substituted aryl group having 6 to 20 ring atoms, or a combination of these groups; any two adjacent Rs x1 Benzene rings or naphthalene rings are connected to each other; And / or, each time R4, R5, R6, R7, R8 and R9 appear, they are independently selected from a substituted or at least R-substituted C1 to C20 aliphatic hydrocarbon group, a substituted or at least R-substituted aliphatic cyclic hydrocarbon group having 3 to 20 ring atoms, a substituted or at least R-substituted aliphatic heterocyclic hydrocarbon group having 3 to 20 ring atoms, a substituted or at least R-substituted C1 to C20 aliphatic hydrocarbon oxy group, a substituted or at least R-substituted C1 to C20 aliphatic hydrocarbon thiol group, or a substituted or at least R-substituted C1 to C20 aliphatic hydrocarbon amino group; And / or, R 10 Selected from arylene groups having 6 to 20 ring atoms that are substituted or substituted with at least one R, heteroarylene groups having 5 to 20 ring atoms that are substituted or substituted with at least one R, or combinations thereof.

4. The organic compound according to claim 3, characterized in that, Ar4 is selected independently from groups (1-1) to (1-14) each time it appears:

5. The organic compound according to claim 4, characterized in that, The organic compound is selected from any of the following structures:

6. A method for preparing an organic compound, characterized in that, Includes the following steps: The first compound and the second compound were mixed and reacted in solution to obtain the first intermediate; A third compound is provided, and the third compound is mixed and reacted with the first intermediate to obtain a first organic compound; A halogenated reagent is provided, and the halogenated reagent is mixed with the first organic compound and reacted to obtain a second intermediate; A fourth compound is provided, and the fourth compound is mixed and reacted with the second intermediate to obtain the organic compound; The first compound has the structure shown in general formula (2) below: In this context, Ar1 is independently selected each time it appears from an aryl group having 6 to 30 unsubstituted or substituted ring atoms with at least one R3, or a heteroaryl group having 5 to 30 unsubstituted or substituted ring atoms with at least one R3, or a combination of these groups; the heteroatoms in the heteroaryl group are independently selected from one or more of N, S, O, P, and Si, and the number of heteroatoms in the heteroaryl group is independently selected from 1 to 20; R3 is independently selected each time it appears from a D, C1 to C20 aliphatic chain hydrocarbon group, C1 to C20 aliphatic chain hydroxyl group, aliphatic cyclic hydrocarbon group having 3 to 30 ring atoms, aliphatic heterocyclic hydrocarbon group having 3 to 30 ring atoms, aryl group having 6 to 30 ring atoms, heteroaryl group having 5 to 60 ring atoms, and -NR. N1 R N2 , halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, or aldehyde, or combinations of these groups; R N1 and R N2 Each group is independently selected from H, D, C1-C20 aliphatic chain hydrocarbon groups, C1-C20 aliphatic chain hydroxyl groups, aliphatic cyclic hydrocarbon groups with 3 to 30 ring atoms, aliphatic heterocyclic hydrocarbon groups with 3 to 30 ring atoms, aryl groups with 6 to 30 ring atoms, or heteroaryl groups with 5 to 30 ring atoms; R m Selected from halogens; The second compound has the structure shown in the following general formula (3): R n Each time it appears, it is independently selected from at least one hydroxyl-substituted C1-C30 aliphatic chain hydrocarbon group, C1-C30 aliphatic chain hydrocarbon oxygen group, or hydroxyl group; R e Selected from hydroxyl, amino, or thiol groups; two R groups n They may form rings or not; The third compound is selected from malononitrile; The halogenated reagent includes one or more of N-bromosuccinimide, N-iodosuccinimide, liquid bromine, iodine powder, and chlorine water; The fourth compound includes compounds having the following structure: In this case, X is selected independently from CR each time it appears. x1 Or N; Z1 and Z2 are each selected independently from NR each time they appear. x2 CR x3 CR x4 R x5 , O or S; Z3 is selected independently from NH or NR each time it appears. 10 ; R x1 R x2 R x3 R x4 and R x5 Each time it appears, it is independently selected from D, a substituted or at least R-substituted C1-C30 aliphatic chain hydrocarbon group, a substituted or at least R-substituted aliphatic cyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted aliphatic heterocyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted C1-C30 aliphatic hydrocarbon oxy group, a substituted or at least R-substituted C1-C30 aliphatic hydrocarbon thiol group, a substituted or at least R-substituted C1-C30 aliphatic hydrocarbon amino group, or a substituted or at least R-substituted aryl group having 6 to 30 ring atoms, or a combination of these groups; any two adjacent Rs x1 They can be connected to form a loop or not; R4, R5, R6, R7, R8 and R9, each time appearing independently, are selected from a substituted or at least R-substituted C1 to C30 aliphatic chain hydrocarbon group, a substituted or at least R-substituted aliphatic cyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted aliphatic heterocyclic hydrocarbon group having 3 to 30 ring atoms, a substituted or at least R-substituted C1 to C30 aliphatic hydrocarbon oxy group, a substituted or at least R-substituted C1 to C30 aliphatic hydrocarbon thiol group, or a substituted or at least R-substituted C1 to C30 aliphatic hydrocarbon amino group, or a combination of these groups. R 10 Selected from substituted or C1-C30 chain alkylene groups, substituted or C1-C30 chain alkene groups, substituted or C1-C30 chain alkene groups, substituted or C1-C30 aryl groups with 6 to 30 ring atoms, substituted or C1-C30 heteroaryl groups with 5 to 30 ring atoms, or combinations of these groups. n2 and n3 are each independently selected from integers from 0 to 5; n4 and n5 are each independently selected from integers from 0 to 4; n6 and n7 are each independently selected from integers from 0 to 4; Each time R appears, it is independently selected from one or more of H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C30 alkyl, C1-C30 alkoxy, and aryl with 6-30 ring atoms.

7. The method for preparing the organic compound according to claim 6, characterized in that, The steps for obtaining the first intermediate specifically include: A first catalyst is provided, and a first compound, a second compound, and the first catalyst are mixed and reacted in solution; the first catalyst includes a palladium catalyst. And / or, R x1 R x2 R x3 R x4 and R x5 Each time it appears, it is independently selected from H, D, a substituted or at least R-substituted C1-C20 aliphatic chain hydrocarbon group, a substituted or at least R-substituted aliphatic cyclic hydrocarbon group having 3 to 20 ring atoms, a substituted or at least R-substituted aliphatic heterocyclic hydrocarbon group having 3 to 20 ring atoms, a substituted or at least R-substituted C1-C20 aliphatic hydrocarbon oxy group, a substituted or at least R-substituted C1-C20 aliphatic hydrocarbon thiol group, a substituted or at least R-substituted C1-C20 aliphatic hydrocarbon amino group, or a substituted or at least R-substituted aryl group having 6 to 20 ring atoms, or a combination of these groups; any two adjacent Rs x1 Benzene rings or naphthalene rings are connected to each other; And / or, each time R4, R5, R6, R7, R8 and R9 appear, they are independently selected from a substituted or at least R-substituted C1 to C20 aliphatic hydrocarbon group, a substituted or at least R-substituted aliphatic cyclic hydrocarbon group having 3 to 20 ring atoms, a substituted or at least R-substituted aliphatic heterocyclic hydrocarbon group having 3 to 20 ring atoms, a substituted or at least R-substituted C1 to C20 aliphatic hydrocarbon oxy group, a substituted or at least R-substituted C1 to C20 aliphatic hydrocarbon thiol group, or a substituted or at least R-substituted C1 to C20 aliphatic hydrocarbon amino group; And / or, R 10 Selected from 6 to 20 aryl groups that are substituted or substituted with at least one R, 5 to 20 heteroaryl groups that are substituted or substituted with at least one R, or combinations thereof; Preferably, the fourth compound comprises one or more of compounds (1-1) to (1-14): Among them, R 11 Selected from halogens; And / or, the reaction temperature in the step of obtaining the first intermediate is 90–150°C; And / or, the reaction temperature in the step of obtaining the first organic compound is 20–60°C; And / or, the reaction temperature in the step of obtaining the organic compound is 100–130°C; And / or, the molar ratio of the first compound to the second compound is 1:(2-4); And / or, the molar ratio of the first intermediate to the third compound is 1:(2-6); And / or, the molar ratio of the second intermediate to the fourth compound is 1:(2-4).

8. A thin film, characterized in that, This includes organic compounds as described in any one of claims 1-5, or organic compounds prepared by the method described in claim 6 or 7.

9. An optoelectronic device, characterized in that, include: The first and second electrodes are positioned relative to each other; as well as Multiple functional layers are disposed between the first electrode and the second electrode; Wherein, the material of at least one of the plurality of functional layers comprises an organic compound as described in any one of claims 1-5.

10. The optoelectronic device according to claim 9, characterized in that, The functional layer includes a hole functional layer, and the material of the hole functional layer includes an organic compound as described in any one of claims 1-5; Optionally, the hole functional layer includes a stacked hole injection layer and a hole transport layer, wherein the hole injection layer is closer to the anode than the hole transport layer, and the material of the hole transport layer includes an organic compound as described in any one of claims 1-5; And / or, the functional layer includes an electronic functional layer, the material of which includes one or more of inorganic electronic functional materials and organic electronic functional materials. The inorganic electronic functional material includes one or more of the first doped metal oxide particles, the first undoped metal oxide particles, the IIB-VIA group semiconductor material, the IIIA-VA group semiconductor material, and the IB-IIIA-VIA group semiconductor material. The organic electronic functional material includes one or more of quinoxaline compounds, imidazole compounds, triazine compounds, fluorene-containing compounds, hydroxyquinoline compounds, and fullerene derivatives. And / or, the functional layer includes an excitation layer, the material of which includes one or more of single-structure quantum dots, core-shell quantum dots, and perovskite semiconductor materials. The material of the single-structure quantum dots, the core material of the core-shell quantum dots, and the shell material of the core-shell quantum dots are each independently selected from one or more of group II-VI compounds, group IV-VI compounds, group III-V compounds, and group I-III-VI compounds. The group II-VI compounds include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, and ZnSeS. One or more of the following compounds: ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and HgZnSTe, wherein the group IV-VI compounds include SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, and SnSTe. PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, SnPbSTe, and the III-V compound includes one or more of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, and G. One or more of aAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and InAlPSb are selected, and the I-III-VI group compounds include one or more of CuInS2, CuInSe2, and AgInS2. The perovskite semiconductor material includes doped or undoped inorganic perovskite semiconductors or organic-inorganic hybrid perovskite semiconductors, and the general structural formula of the inorganic perovskite semiconductor is AMX3, where A is Cs. + Ions, where M is a divalent metal cation, including Pb 2+ Sn 2+ Cu 2+ Ni 2+ Cd 2+ Cr 2+ Mn 2+ Co 2+ Fe 2+ 、Ge 2+ Yb 2+ Eu 2+ One or more of them, where X is a halide anion, including Cl. - ,Br - I - One or more of the following; the general structural formula of the organic-inorganic hybrid perovskite semiconductor is BMX3, where B is an organic amine cation, including CH3(CH2). n-2 NH3 + Or [NH3(CH2)] n NH3] 2+ Where n≥2, M is a divalent metal cation, including Pb 2+ Sn 2+ Cu 2+ Ni 2+ Cd 2+ Cr 2+ Mn 2+ Co 2+ Fe 2+ 、Ge 2+ Yb 2+ Eu 2+ One or more of them, where X is a halide anion, including Cl. - ,Br - I - One or more of them.

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