Organic compound, synthetic method of organic compound, photoelectric device and display device

Abstract

The invention provides an organic compound, a synthetic method of the organic compound, a photoelectric device and a display device. By using the film layer comprising the compound shown in the general formula (1) between the hole functional layer and the electronic functional layer of the photoelectric device, the luminous efficiency of the device can be improved, and the service life can be prolonged.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of optoelectronic devices, in particular to an organic compound, a synthesis method of the organic compound, an optoelectronic device and a display device. BACKGROUND

[0002] The currently widely used QLED has the advantages of saturated color of outgoing light, adjustable wavelength, low turn-on voltage, good solution processability, and easy fine control of quantum dots.

[0003] The traditional QLED device structure generally includes an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode. Under the action of an electric field, the holes generated by the anode of the optoelectronic device and the electrons generated by the cathode move and are injected into the hole transport layer and the electron transport layer, respectively, and finally migrate to the light-emitting layer. When the two meet in the light-emitting layer, an energy exciton is generated, thereby exciting the light-emitting molecules to finally produce visible light.

[0004] The existing optoelectronic device has a low light-emitting effect, which needs to be further improved. SUMMARY

[0005] Embodiments of the present application provide an organic compound, a synthesis method of the organic compound, an optoelectronic device and a display device, which can improve the technical problem of low light-emitting efficiency.

[0006] In a first aspect, embodiments of the present application provide an organic compound comprising a compound as shown in general formula (1)

[0007]

[0008]

[0009] wherein R z , R s and R t are each independently selected from

[0010] Ar1 is each independently selected from an unsubstituted or substituted with at least one R aryl group having 6 to 30 ring atoms, or an unsubstituted or substituted with at least one R heteroaryl group having 5 to 30 ring atoms, or a combination of these groups; the heteroatoms in the heteroaryl group are each independently selected from one or more of N, S, O, P and Si, and the number of heteroatoms in the heteroaryl group is each independently selected from 1 to 20;

[0011] L1 is each independently selected from a single bond, an unsubstituted or substituted with at least one R aliphatic chain having 1 to 30 carbon atoms, a hydroxyl group, an aldehyde group, a thiol group, an ether group, an ester group, an amino group, a carbonyl group, a nitro group, a halogen; ​

[0012] Each time L2 appears, it is independently selected from unsubstituted or C1-C30 aliphatic chain hydrocarbon group, hydroxyl group, aldehyde group, mercapto group, ether group, ester group, amino group, carbonyl group, or nitro group, either substituted with at least one R.

[0013] Each time R appears, it is independently selected from deuterium, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, aldehyde, or amide, or a combination of these groups.

[0014] Secondly, embodiments of this application provide a method for synthesizing an organic compound, comprising the following steps:

[0015] The first compound and the second compound are mixed and reacted in a first solvent to obtain an organic compound;

[0016] The structure of the first compound is shown in general formula (I):

[0017]

[0018] Among them, R m R n and R q Each time it appears, it is selected independently.

[0019] Each time Ar2 appears, it is independently selected from aryl groups having 6 to 30 unsubstituted or substituted ring atoms with at least one R, or heteroaryl groups having 5 to 30 unsubstituted or substituted ring atoms with at least one R, 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, and the number of heteroatoms in the heteroaryl groups is independently selected from 1 to 20.

[0020] Each time L3 appears, it is independently selected from single bonds, unsubstituted or substituted with at least one R, aliphatic chain hydrocarbon group, hydroxyl group, aldehyde group, mercapto group, ether group, ester group, amino group, carbonyl group, nitro group, halogen group;

[0021] Each time R appears, it is independently selected from deuterium, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, aldehyde, or amide, or a combination of these groups;

[0022] The structure of the second compound is shown in general formula (II):

[0023]

[0024] Wherein, L4 is selected from unsubstituted or C1-C30 aliphatic chain hydrocarbon group, hydroxyl group, aldehyde group, mercapto group, ether group, ester group, amino group, carbonyl group, or nitro group, which are either unsubstituted or substituted with at least one R.

[0025] L5is selected from halogen;

[0026] R is independently selected at each occurrence from deuterium, halogen, hydroxyl, carboxyl, nitro, sulfonic, thiol, cyano, aldehyde, or amide, or a combination of these groups.

[0027] In a third aspect, embodiments of the present application provide an optoelectronic device, comprising, which are stacked in sequence:

[0028] a first electrode;

[0029] a functional layer comprising the organic compound as described above, or the organic compound synthesized by the synthesis method of the organic compound as described above; and

[0030] a second electrode.

[0031] In a fourth aspect, embodiments of the present application provide a display device comprising the optoelectronic device as described above.

[0032] Advantages of embodiments of the present application:

[0033] In embodiments of the present application, by using a film layer comprising the compound as shown in general formula (1) between the hole functional layer and the electron functional layer of the optoelectronic device, the surface of the adjacent film layer can be improved, the light-emitting efficiency of the device can be improved, and the service life can be prolonged. BRIEF DESCRIPTION OF DRAWINGS

[0034] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings needed in the embodiment description will be briefly introduced as follows. Obviously, the drawings in the following description are only some embodiments of the present application, and other drawings can also be obtained according to these drawings without creative labor.

[0035] Figure 1 is a structural schematic diagram of the device QLED-1 provided by embodiments of the present application.

[0036] Explanation of reference signs:

[0037] 1, anode; 2, hole functional layer; 3, excitation layer; 4, modification layer; 5, electron transport layer; 6, cathode. DETAILED DESCRIPTION

[0038] With reference to the drawings, the technical solutions in the embodiments of the present application will be described clearly and completely. Obviously, the described embodiments are only a part of the embodiments of the present application, but not all the embodiments of the present application. Based on the embodiments in the present application, all the other embodiments obtained by a person of ordinary skill in the art without creative work are within the scope of the present application. In addition, it should be understood that the specific implementation described herein is only used to illustrate and explain the present application, and is not used to limit the present application.

[0039] In the present application, the orientation words such as "upper" and "lower" generally refer to the upper and lower in the actual use or working state of the device, and specifically refer to the direction of the drawing surface in the drawings. In addition, "inner" and "outer" refer to the outline of the device. In addition, in the description of the present application, the term "comprising" means "including but not limited to". The terms first, second, third, etc. are only used as labels, and do not impose numerical requirements or establish sequences.

[0040] In the present application, "and / or" describes the association relationship of the associated objects, which means that there can be three kinds of relationships, for example, A and / or B can represent the following three cases: A exists alone, A and B exist together, and B exists alone. Wherein A and B can be singular or plural.

[0041] In the present application, "at least one" means one or more, and "multiple" means two or more. "At least one", "at least one of the following" or the like means any combination of these items, including any combination of single item or multiple items. For example, "at least one of a, b, or c", or "at least one of a, b, and c", can represent a, b, c, a-b (i.e. a and b), a-c, b-c, or a-b-c, where a, b, and c can be single or multiple.

[0042] In the present application, in forming another layer "on" a certain layer, the so-called "on" is a broad concept, which can mean that the formed another layer is adjacent to the certain layer, or that there is another spacer structure layer between the another layer and the certain layer. For example, forming a second electrode "on" a first carrier functional layer, the so-called "on" can mean that the formed second electrode is adjacent to the first carrier functional layer, or that there is another spacer structure layer, such as a light-emitting layer, between the second electrode and the first carrier functional layer.

[0043] Various embodiments of the present application can exist in a range of forms; it should be understood that the description in a range form is merely for the convenience and brevity, and should not be construed as a hard limitation on the scope of the present application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single values within the range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single values within the range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. In addition, whenever a numerical range is indicated herein, it is meant to include any cited number (fraction or integer) within the indicated range.

[0044] The present application provides an organic compound, a synthesis method of an organic compound, and an optoelectronic device. In order to make the purpose, technical solutions and effects of the present application more clear and explicit, the present application is further described in detail below. It should be understood that the specific embodiments described herein are only used to explain the present application and not to limit the present application. The technical solutions of the present application are as follows:

[0045] In the present application, "substituted" means that the hydrogen atom in the substituent is replaced by the substituent.

[0046] In the present application, when the same substituent appears multiple times, it can be independently selected from different groups. For example, the general formula contains multiple R 1 , R 1 may be independently selected from different groups. For example, the general formula contains three R 1 , which can be the same or different from each other.

[0047] In the present application, "substituted or unsubstituted" means that the defined group can be substituted or unsubstituted. When the defined group is substituted, it is understood that the defined group can be substituted by one or more substituents R, which are selected from but not limited to: deuterium atom, cyano group, isocyano group, nitro group, halogen, alkyl group containing 1-30 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silyl group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, halogen formyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above-mentioned groups can be further substituted by acceptable substituents in the art; it can be understood that R' and R" in -NR'R" are independently selected from but not limited to: hydrogen atom, deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1-10 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms.

[0048] Preferably, R' and R" are independently selected from, but not limited to: a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen, an alkyl group containing 1-10 C atoms, a heterocyclic group containing 3-10 ring atoms, an aromatic group containing 6-20 ring atoms, a heteroaromatic group containing 5-20 ring atoms, a silyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a halogenformyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, and the aforementioned groups can also be further substituted with art-acceptable substituents.

[0049] In the present application, the "number of ring atoms" means the number of atoms in a compound of a structure in which atoms are bonded to form a ring, such as a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, and a heterocyclic compound. When the ring is substituted with a substituent, the atoms included in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below, unless otherwise specified. For example, the number of ring atoms in a benzene ring is 6, the number of ring atoms in a naphthalene ring is 10, and the number of ring atoms in a thiophene group is 5.

[0050] In the present application, "aryl group or aromatic group" means an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, and can be a monocyclic aryl group, or a fused ring aryl group or a polycyclic aryl group, and at least one of the rings in the polycyclic ring is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 6-40 ring atoms" means an aryl group having 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, particularly preferably a substituted or unsubstituted aryl group having 6-14 ring atoms, and the aryl group is optionally further substituted. Suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, rylene, acenaphthyl, and derivatives thereof. It is understood that multiple aryl groups can also be interrupted by short non-aromatic units (e.g. less than 10% of the non-H atoms, such as C atoms, N atoms or O atoms, are in a molar ratio), in particular acenaphthene, fluorene such as 9,9-dialkylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl groups.

[0051] In the present application, "heteroaryl or heteroaromatic group" means that at least one carbon atom of the aryl group is replaced by a non-carbon atom, which can be N atom, O atom, S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" means a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted, and suitable examples include, but are not limited to: thienyl, furanyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, perylenyl, phenanthridinyl, berberinyl, quinazolinonyl, dibenzothienyl, dibenzofuranyl, carbazolyl, and derivatives thereof.

[0052] In the present application, "alkyl" can mean straight chain, branched, and / or cyclic alkyl groups. The number of carbons in an alkyl group can be 1-50, 1-30, 1-20, 1-10, or 1-6. Phrases containing this term, for example, "C1-9 alkyl" means an alkyl group containing 1-9 carbon atoms, each occurrence of which can be independently 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, i-propyl, n-butyl, s-butyl, t-butyl, i-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethyihexadecyl, 2-butyihexadecyl, 2-hexyihexadecyl, 2-octyihexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyileicosyl, 2-hexyleicosyl, 2-octyleicosyl, n- heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, and the like.

[0053] In the present application, "amino" means a derivative of an amine, having the structural feature of the formula -N(X)2, where each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, and the like. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclyl)2, -NH(heterocyclyl), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), and the like.

[0054] In the present application, when no site of attachment is indicated in a radical, it is represented that any available site in the radical can serve as the site of attachment.

[0055] In the present application, the single bond to which the substituent is attached runs through the corresponding ring, indicating that the substituent can be connected to any optional position of the ring, for example R in the above formula (1) can be connected to any substitutable position of the benzene ring.

[0056] In the present application, the organic base refers to amine compounds and nitrogen-containing heterocyclic compounds, and the amine compounds refer to C8-C22 aliphatic amines and aromatic amines, and the aromatic amines refer to heteroaryl groups with 5 to 30 ring atoms, and at least one heteroatom is selected from N.

[0057] In a first aspect, the embodiments of the present application provide an organic compound, including a compound as shown in the general formula (1):

[0058]

[0059] wherein R z , R s and R t are each independently selected from

[0060] Ar1 is each independently selected from an unsubstituted or substituted with at least one R, 6-30 ring atom aryl group, or an unsubstituted or substituted with at least one R, 5-30 ring atom heteroaryl group, or a combination of these groups; the heteroatoms in the heteroaryl group are each independently selected from one or more of N, S, O, P and Si, and the number of heteroatoms in the heteroaryl group is each independently selected from 1-20;

[0061] L1 is each independently selected from a single bond, an unsubstituted or substituted with at least one R, C1-C30 aliphatic chain hydrocarbon group, a hydroxyl group, an aldehyde group, a thiol group, an ether group, an ester group, an amino group, a carbonyl group, a nitro group, a halogen;

[0062] L2 is each independently selected from an unsubstituted or substituted with at least one R, C1-C30 aliphatic chain hydrocarbon group, a hydroxyl group, an aldehyde group, a thiol group, an ether group, an ester group, an amino group, a carbonyl group, or a nitro group;

[0063] R is each independently selected from deuterium, halogen, hydroxyl, carboxyl, nitro, sulfonic acid group, thiol, cyano, aldehyde, or amide group, or a combination of these groups.

[0064] In the compound provided by the present application, the organic compound can play a role of chelating uncoordinated metal due to the amide group and the L2 group, and thus when the organic compound is applied to an optoelectronic device, the organic compound can play a role of modifying chelating uncoordinated metal on the surface of a hole functional layer and a quantum dot layer as a modification layer between the hole functional layer and the quantum dot layer, thereby improving surface defects of the film layer, improving carrier transport efficiency, and further improving luminous efficiency of the device and prolonging service life.

[0065] In some embodiments, Ar1is independently selected from the following groups:

[0066]

[0067] wherein X is independently selected from CR1or NR1at each occurrence, and R1is independently selected from hydrogen, deuterium, halogen, hydroxyl, carboxyl, nitro, sulfonic acid group, thiol, cyano, aldehyde, amide, C1-C30 aliphatic chain hydrocarbon group unsubstituted or substituted with at least one R, C1-C30 aliphatic chain hydrocarbon oxy group unsubstituted or substituted with at least one R, C3-C30 aliphatic cyclic hydrocarbon group unsubstituted or substituted with at least one R, C3-C30 aliphatic heterocyclic hydrocarbon group unsubstituted or substituted with at least one R, aryl group having 6 to 30 ring atoms unsubstituted or substituted with at least one R, aryloxy group having 6 to 30 ring atoms unsubstituted or substituted with at least one R, heteroaryl group having 5 to 30 ring atoms unsubstituted or substituted with at least one R, or heteroaryloxy group having 5 to 30 ring atoms unsubstituted or substituted with at least one R, or a combination thereof; the heteroatoms in the aliphatic heterocyclic hydrocarbon group, the heteroaryl group, and the heteroaryloxy group are independently selected from one or more of N, S, O, P, and Si, and the number of the heteroatoms in the aliphatic heterocyclic hydrocarbon group, the heteroaryl group, and the heteroaryloxy group is independently selected from 1 to 20;

[0068] Y is independently selected from S, N, O, C1-C30 aliphatic chain hydrocarbon group unsubstituted or substituted with at least one R, C3-C30 aliphatic cyclic hydrocarbon group unsubstituted or substituted with at least one R, or C3-C30 aliphatic heterocyclic hydrocarbon group unsubstituted or substituted with at least one R at each occurrence.

[0069] In some embodiments, further, the general formula (1) is selected from the general formula (2-1) or the general formula (2-2):

[0070]

[0071] In some embodiments, Ar1is independently selected from aryl group having 6 to 10 ring atoms unsubstituted or substituted with at least one R at each occurrence; and / or

[0072] L1is independently selected at each occurrence from a single bond, an unsubstituted or at least one R-substituted C1-C8linear alkyl group, an unsubstituted or at least one R-substituted C3-C8branched alkyl group; and / or

[0073] L2is independently selected at each occurrence from a C1-C30haloalkyl group.

[0074] In some embodiments, the organic compound is selected from any one of the following structures:

[0075]

[0076]

[0077] In a second aspect, embodiments of the present application provide a method for synthesizing an organic compound, comprising the following steps:

[0078] mixing and reacting the first compound and the second compound in a first solvent to obtain the organic compound; wherein the first compound has a structure as shown in the general formula (I):

[0079]

[0080] wherein R m , R n , and R q are each independently selected at each occurrence from

[0081] Ar2is independently selected at each occurrence from an unsubstituted or at least one R-substituted aryl group having 6 to 30 ring atoms, or an unsubstituted or at least one R-substituted heteroaryl group having 5 to 30 ring atoms, or a combination thereof; the heteroatoms in the heteroaryl group are independently selected at each occurrence from one or more of N, S, O, P, and Si, and the number of heteroatoms in the heteroaryl group is independently selected at each occurrence from 1 to 20;

[0082] L3is independently selected at each occurrence from a single bond, an unsubstituted or at least one R-substituted C1-C30aliphatic chain, a hydroxyl group, an aldehyde group, a thiol group, an ether group, an ester group, an amino group, a carbonyl group, a nitro group, a halogen;

[0083] R is independently selected at each occurrence from deuterium, a halogen, a hydroxyl group, a carboxyl group, a nitro group, a sulfonic acid group, a thiol group, a cyano group, an aldehyde group, or an amide group, or a combination thereof;

[0084] wherein the second compound has a structure as shown in the general formula (II):

[0085]

[0086] L4is selected from a C1-C30 aliphatic chain hydrocarbon group, which is unsubstituted or substituted with at least one R, a hydroxyl group, an aldehyde group, a thiol group, an ether group, an ester group, an amino group, a carbonyl group, or a nitro group;

[0087] L5is selected from a halogen;

[0088] R is independently selected at each occurrence from deuterium, a halogen, a hydroxyl group, a carboxyl group, a nitro group, a sulfonic acid group, a thiol group, a cyano group, an aldehyde group, or an amide group, or a combination of these groups.

[0089] In some embodiments, Ar2is independently selected at each occurrence from the following groups:

[0090]

[0091] wherein X is independently selected at each occurrence from CR1or NR1, and R1is independently selected at each occurrence from hydrogen, deuterium, a halogen, a hydroxyl group, a carboxyl group, a nitro group, a sulfonic acid group, a thiol group, a cyano group, an aldehyde group, an amide group, a C1-C30 aliphatic chain hydrocarbon group, which is unsubstituted or substituted with at least one R, a C1-C30 aliphatic chain hydroxyl group, which is unsubstituted or substituted with at least one R, a C3-C30 aliphatic cyclic hydrocarbon group, which is unsubstituted or substituted with at least one R, a C3-C30 aliphatic heterocyclic hydrocarbon group, which is unsubstituted or substituted with at least one R, an aryl group having 6 to 30 ring atoms, which is unsubstituted or substituted with at least one R, an aryloxy group having 6 to 30 ring atoms, which is unsubstituted or substituted with at least one R, a heteroaryl group having 5 to 30 ring atoms, which is unsubstituted or substituted with at least one R, or a heteroaryloxy group having 5 to 30 ring atoms, which is unsubstituted or substituted with at least one R, or a combination of these groups; the heteroatoms in the aliphatic heterocyclic hydrocarbon group, the heteroaryl group, and the heteroaryloxy group are independently selected from one or more of N, S, O, P, and Si, and the number of the heteroatoms in the aliphatic heterocyclic hydrocarbon group, the heteroaryl group, and the heteroaryloxy group is independently selected from 1 to 20;

[0092] Y is independently selected at each occurrence from S, N, O, a C1-C30 aliphatic chain hydrocarbon group, which is unsubstituted or substituted with at least one R, a C3-C30 aliphatic cyclic hydrocarbon group, which is unsubstituted or substituted with at least one R, or a C3-C30 aliphatic heterocyclic hydrocarbon group, which is unsubstituted or substituted with at least one R; and / or

[0093] The third compound is further mixed with the first compound and the second compound in the first solvent, and the third compound comprises an organic base; and / or

[0094] The first solvent comprises an organic solvent.

[0095] In some embodiments, further, the general formula (I) is selected from the general formula (I-1) or the general formula (I-2):

[0096] In some embodiments, Ar2is independently at each occurrence selected from an aryl group having from 6 to 10 ring atoms which is unsubstituted or substituted with at least one R; and / or

[0097] L3is independently at each occurrence selected from a single bond, a C1-C8straight chain alkyl group which is unsubstituted or substituted with at least one R, a C3-C8branched alkyl group which is unsubstituted or substituted with at least one R; and / or

[0098] L4is independently at each occurrence selected from a C1-C30halogenated alkyl group.

[0099] In some embodiments, the third compound is selected from NR1R2R3, R1, R2and R3are independently at each occurrence selected from hydrogen, deuterium, a C1-C30aliphatic chain which is unsubstituted or substituted with at least one R; preferably, the third compound is selected from a tertiary amine, such as triethylamine, to avoid by-products generated after the reaction is completed.

[0100] In some embodiments, the step of mixing the first compound and the second compound in the first solvent comprises: dissolving the first compound in the first solvent, then adding the third compound, slowly dropping the second compound at 0°C, and stirring at 25°C.

[0101] In some embodiments, the step of mixing the first compound and the second compound in the first solvent is preceded by a step of synthesizing the first compound:

[0102] A first precursor having a general formula (III) and a second precursor having a general formula (IV) are provided, the first precursor and the second precursor are dissolved in a precursor solvent, and heated to obtain a first intermediate product:

[0103] A fourth compound is selected from one or more of hydrazine hydrate, borane, diisobutylaluminum hydride, lithium aluminum hydride, sodium borohydride, and potassium borohydride, and the fourth compound and the first intermediate product are dissolved in a second intermediate solvent to obtain the first compound.

[0104] wherein the general formula (III) is:

[0105]

[0106] wherein Z m , Z n and Z q are independently at each occurrence selected from Ar2-L3;

[0107] wherein the general formula (IV) is:

[0108]

[0109] In some embodiments, the step of mixing the first precursor and the second precursor specifically comprises: mixing the first precursor, the second precursor, CuI, a strong base weak acid salt and dissolved in the precursor solvent; and / or

[0110] The first solvent comprises dichloromethane; and / or

[0111] The precursor solvent is selected from one or more of dioxane, dimethyl sulfoxide, toluene, xylene; and / or

[0112] The boiling point of the second intermediate solvent is less than or equal to 100°C; preferably, the second intermediate solvent is acetonitrile. In this way, a second intermediate solvent with a lower boiling point is selected to facilitate removal under vacuum.

[0113] wherein R4and R5are each independently selected from a C1-C30 aliphatic chain hydrocarbon group which is unsubstituted or substituted with at least one R.

[0114] In the embodiments of the present application, the strong base weak acid salt refers to a salt generated by the reaction of a strong base and a weak acid, and is alkaline in water. The cation in the strong base weak acid salt is selected from Na + , K + , Ca 2+ or Ba 2+ , but is not limited thereto. The anion is selected from carbonate ions, sulfite ions, bisulfite ions, silicate ions, metavanadate ions, hypochlorite ions or acetate ions, but is not limited thereto.

[0115] In a third aspect, the embodiments of the present application provide an optoelectronic device, comprising, which are arranged in layers:

[0116] a first electrode;

[0117] a functional layer comprising the organic compound as described above, or the organic compound synthesized by the synthesis method of the organic compound as described above; and

[0118] a second electrode.

[0119] In some embodiments, the material of the first electrode and the second electrode respectively and independently comprises a doped metal oxide electrode, a composite electrode, a graphene electrode, a carbon nanotube electrode, a metal element electrode or an alloy electrode, the material of the doped metal oxide electrode comprises one or more of indium-doped tin oxide, fluorine-doped tin oxide, antimony-doped tin oxide, aluminum-doped zinc oxide, gallium-doped zinc oxide, indium-doped zinc oxide, magnesium-doped zinc oxide, aluminum-doped magnesium oxide, cadmium-doped zinc oxide, the composite electrode comprises AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, TiO2 / Ag / TiO2, TiO2 / Al / TiO2, ZnS / Ag / ZnS, ZnS / Al / ZnS, Ca / Al, LiF / Ca, LiF / Al, BaF2 / Al, CsF / Al, CaCO3 / Al or BaF2 / Ca / Al, the material of the metal element electrode comprises one or more of Ag, Ni, Pt, Au, Ir, Cu, Mo, Al, Ca, Mg and Ba, and the alloy electrode comprises an Au:Mg alloy electrode or an Ag:Mg alloy electrode; and / or

[0120] The functional layer further comprises a hole functional layer, a modification layer, an excitation layer and an electron functional layer which are stacked; the material of the hole functional layer comprises one or more of 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'-di(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)benzidine)], poly(N-vinylcarbazole) and derivatives thereof, N,N'-di(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4-4'-diamine, spiro NPB, poly(phenylenevinylene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene], poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene], 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene, 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)benzidine], 1,3-bis(carbazol-9-yl)benzene, polyaniline, polypyrrole, poly(p)phenylenevinylene, aromatic tertiary amine, polynuclear aromatic tertiary amine, 4,4'-bis(p-carbazolyl)-1,1'-biphenyl compound, N,N,N',N'-tetraarylbenzidine, PEDOT:PSS and derivatives thereof, polymethacrylate and derivatives thereof, poly(9,9-octylfluorene) and derivatives thereof, poly(spirofluorene) and derivatives thereof, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene, PEDOT, PEDOT:PSS, derivatives of PEDOT:PSS doped with s-MoO3, 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, tetracyanoquinodimethane, doped graphene, non-doped graphene, C60, copper phthalocyanine, second doped metal oxide particles, second non-doped metal oxide particles, metal sulfides and metal nitrides; and / or

[0121] The modification layer comprises an organic compound as described above, or an organic compound synthesized by a synthesis method of an organic compound as described above; and / or

[0122] The material of the excitation layer 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 independently selected from one or more of II-VI compounds, IV-VI compounds, III-V compounds and I-III-VI compounds, the II-VI compounds include one or more of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and HgZnSTe, the IV-VI compounds include one or more of SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, SnPbSTe, the III-V compounds include one or more of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs and InAlPSb, the I-III-VI compounds include one or more of CuInS2, CuInSe2 and AgInS2; the perovskite semiconductor material includes doped or non-doped inorganic perovskite semiconductor or organic-inorganic hybrid perovskite semiconductor, the general structure of the inorganic perovskite semiconductor is AMX3, wherein A is Cs + ion, M is a divalent metal cation, including Pb 2+ , Sn 2+ , Cu 2+ , Ni 2+ , Cd2+ Cr 2+ Mn 2+ Co 2+ Fe 2+ Ge 2+ Yb 2+ Eu 2+ one or more of Cr - , Br - , I - ; the structure general formula of the organic-inorganic hybrid perovskite type semiconductor is BMX3, wherein B is an organic amine cation, including CH3(CH2) n- 2NH3 + or [NH3(CH2) n NH3] 2+ , wherein 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 Cr - , Br - , I - ; and / or

[0123] The material of the electronic functional layer includes one or more of inorganic electronic functional materials and organic electronic functional materials, the inorganic electronic functional materials include one or more of first doped type metal oxide particles, first non-doped type metal oxide particles, IIB-VIA group semiconductor materials, IIIA-VA group semiconductor materials and IB-IIIA-VIA group semiconductor materials, and the organic electronic functional materials include one or more of quinoxaline compounds, imidazole compounds, triazine compounds, fluorene-containing compounds, hydroxyquinoline compounds and fullerene derivatives.

[0124] In a fourth aspect, an embodiment of the present application provides a preparation method of the photoelectric device, and the photoelectric device is prepared by the method, and the method includes the following steps:

[0125] depositing a hole injection layer material on the first electrode to prepare a hole injection layer;

[0126] depositing a hole transport layer material on the hole injection layer to prepare a hole transport layer;

[0127] depositing a quantum dot material on the hole transport layer to form an excitation layer;

[0128] depositing an organic compound on the excitation layer to form a modification layer;

[0129] depositing an electron transport layer material on the modification layer to form an electron transport layer;

[0130] depositing a material of the second electrode on the modification layer to form the second electrode.

[0131] encapsulating.

[0132] In some embodiments, the method for preparing the optoelectronic device can also be:

[0133] depositing an electron transport layer material on the first electrode to form an electron transport layer;

[0134] depositing an organic compound on the electron transport layer to form a modification layer;

[0135] depositing a quantum dot material on the electron transport layer to form an excitation layer;

[0136] depositing a hole transport layer material on the excitation layer to form a hole transport layer;

[0137] depositing a hole injection layer material on the hole transport layer to form a hole injection layer;

[0138] depositing a material of the anode on the hole injection layer to form the anode.

[0139] encapsulating.

[0140] The deposition method can be achieved by using techniques well known in the art, specifically:

[0141] The excitation layer can be formed by chemical vapor deposition, successive ionic layer adsorption and reaction, anodic oxidation, coprecipitation, and solution processing. The chemical methods include, for example, chemical vapor deposition, successive ionic layer adsorption and reaction, anodic oxidation, electrolytic deposition, and coprecipitation.

[0142] The hole transport layer can be formed by physical vapor deposition, such as thermal evaporation, electron beam evaporation, magnetron sputtering, multi-arc ion plating, physical vapor deposition, atomic layer deposition, and pulsed laser deposition; or solution processing, such as spin coating, printing, inkjet printing, blade coating, printing, dip-coating, immersion, spraying, roll coating, casting, slot coating, and stripe coating.

[0143] The electron transport layer can be formed by chemical vapor deposition, successive ionic layer adsorption and reaction, anodic oxidation, coprecipitation, and solution processing.

[0144] When the hole injection layer is an organic molecular compound, all the above-mentioned methods can be used; when the hole injection layer is an inorganic molecular compound, a solution processing method can be used.

[0145] The specific treatment method and treatment condition can refer to the common method in the art, which is not described here.

[0146] In a fifth aspect, the embodiments of the present application provide a display device comprising the optoelectronic device as described above. The display device can be any electronic product with display function, including but not limited to a smart phone, a tablet computer, a notebook computer, a digital camera, a digital camcorder, a smart wearable device, a smart weighing electronic scale, a vehicle-mounted display, a television or an electronic book reader, wherein the smart wearable device can be a smart bracelet, a smart watch, a virtual reality (VR) helmet, etc.

[0147] Embodiment 1

[0148] The embodiments of the present application provide an organic compound and a synthesis method thereof. The synthesis method of the organic compound comprises the following steps:

[0149] S1, 9.83 g of tri-(4-bromophenyl)amine, 1 g of phthalimide, 0.387 g of CuI, 2.16 g of K3PO4 and 0.3 mL of N,N-dimethylacetamide are dissolved in 20 mL of dioxane and stirred sufficiently, then refluxed at 110°C for 24 h. After the reaction is completed, the mixture is dried into a powder. The initial product is obtained by silica gel column chromatography with dichloromethane and petroleum ether in a volume ratio of 2.5:1 as eluent;

[0150] S2, 1.6 mL of 35% hydrazine hydrate is slowly dropped into 60 mL of acetonitrile, and then 408.5 mg of the initial product is added. The mixture is stirred at 25°C for 2 h, and then acetonitrile is removed under vacuum. The crude product is further purified by silica gel column chromatography with CH2Cl2 as eluent to obtain an intermediate product;

[0151] S3, 0.112 mg of the intermediate product is dissolved in 5 mL of CH2Cl2, 36 μL of triethylamine is added, and then 20 μL of chloroacetyl chloride is slowly dropped at 0°C. The mixture is stirred at 25°C for 15 min. After the reaction is completed, CH2Cl2 is removed under vacuum to obtain a product to be purified. The product to be purified is further purified by silica gel column chromatography with CH2Cl2 as eluent. The obtained crude substance is dissolved in CH2Cl2, and then recrystallized in n-hexane. After filtration and washing with n-hexane, the obtained organic compound M1 is:

[0152] The molecular formula of the organic compound M1 is: 24 H21 N4O3Cl3, the nuclear magnetic hydrogen spectrum parameters of the organic compound M1 are: 1 H NMR (500 MHz, Chloroform-d) δ 9.18 (s, 3H), 7.83-7.77 (m, 6H), 7.24-7.19 (m, 6H), 4.21 (s, 6H).

[0153] Example 2

[0154] The embodiment of the present application provides an organic compound and a synthesis method thereof, and the synthesis method of the organic compound is different from that of the embodiment 1, wherein the dioxane in the step S1 is replaced by DMSO; the chloroacetyl chloride in the step S3 is replaced by 3-chloropropionyl chloride.

[0155] The obtained organic compound M2 is:

[0156] The molecular formula of the organic compound M2 is: 27 H 27 N4O3Cl3, the nuclear magnetic hydrogen spectrum parameters of the organic compound M2 are: 1 H NMR (500 MHz, Chloroform-d) δ 8.87 (s, 3H), 7.80-7.74 (m, 6H), 7.24-7.19 (m, 6H), 3.86 (t, J=3.1 Hz, 6H), 2.81 (t, J=3.1 Hz, 6H).

[0157] Example 3

[0158] The embodiment of the present application provides an organic compound and a synthesis method thereof, and the synthesis method of the organic compound is different from that of the embodiment 1, wherein the hydrazine in the step S2 is replaced by borane, the chloroacetyl chloride in the step S3 is replaced by 3-bromopropionyl chloride, and the triethylamine in the step S3 is replaced by tripropylamine. The organic compound M2 is obtained.

[0159] Example 4

[0160] The embodiment of the present application provides an organic compound and a synthesis method thereof, and the synthesis method of the organic compound is different from that of the embodiment 1, wherein the hydrazine in the step S2 is replaced by sodium borohydride, the chloroacetyl chloride in the step S3 is replaced by 4-chloroheptanoyl chloride, and the triethylamine in the step S3 is replaced by tri-n-butylamine; the organic compound M3 is obtained:

[0161] The molecular formula of the organic compound M3 is: 39 H 51 N4O3Cl3, the nuclear magnetic hydrogen spectrum parameters of the organic compound M3 are: 1H NMR (500 MHz, Chloroform-d) δ 8.57 (s, 3H), 7.77-7.73 (m, 6H), 7.24-7.19 (m, 6H), 3.90 (p, J = 6.1 Hz, 3H), 2.57-2.49 (m, 6H), 1.92-1.83 (m, 12H), 1.47 (dqt, J = 13.0, 7.7, 5.3 Hz, 6H), 0.93 (t, J = 7.6 Hz, 9H).

[0162] Example 5

[0163] The embodiment of the present application provides an organic compound and a synthesis method thereof, and the synthesis method of the organic compound is different from that of the embodiment 1, wherein the chloroacetyl chloride in step S3 is replaced by 4-chlorobutyryl chloride, so as to obtain the organic compound M4.

[0164] The molecular formula of the organic compound M4 is C 30 H 33 N4O3Cl3, and the nuclear magnetic hydrogen spectrum parameters of the organic compound M4 are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 8.61 (s, 3H), 7.78-7.72 (m, 6H), 7.24-7.19 (m, 6H), 3.67 (t, J = 3.5 Hz, 6H), 2.39 (t, J = 7.3 Hz, 6H), 2.17 (tt, J = 7.1, 3.5 Hz, 6H).

[0165] Example 6

[0166] The embodiment of the present application provides an organic compound and a synthesis method thereof, and the synthesis method of the organic compound is different from that of the embodiment 1, wherein the chloroacetyl chloride in step S3 is replaced by 4-chlorobutyryl chloride, so as to obtain the organic compound M4.

[0167] Example 7

[0168] The embodiment of the present application provides an organic compound and a synthesis method thereof, and the synthesis method of the organic compound is different from that of the embodiment 1, wherein the chloroacetyl chloride in step S3 is replaced by 2-bromoisobutyryl bromide, so as to obtain the organic compound M5.

[0169] The molecular formula of the organic compound M5 is C 30 H 21 N4O3Cl3, and the nuclear magnetic hydrogen spectrum parameters of the organic compound M5 are as follows: 1H NMR (500 MHz, Chloroform-d) δ 7.84-7.78 (m, 6H), 7.48 (s, 3H), 7.24-7.19 (m, 6H), 1.82 (s, 18H).

[0170] Example 8

[0171] The embodiment of the present application provides an organic compound and a synthesis method thereof, and the synthesis method of the organic compound is different from that of the embodiment 1, wherein the chloroacetyl chloride in the step S3 is replaced by bromoacetyl bromide to obtain the organic compound M6.

[0172] The molecular formula of the organic compound M6 is C 24 H 21 N4O3Br3, and the nuclear magnetic hydrogen spectrum parameters of the organic compound M6 are as follows. 1 H NMR (500 MHz, Chloroform-d) δ 7.84-7.78 (m, 6H), 7.48 (s, 3H), 7.24-7.19 (m, 6H), 1.82 (s, 18H).

[0173] Example 9

[0174] The embodiment of the present application provides an organic compound and a synthesis method thereof, and the synthesis method of the organic compound is different from that of the embodiment 1, wherein the chloroacetyl chloride in the step S3 is replaced by bromoacetyl bromide to obtain the organic compound M6. CAS: 100693-36-5, to obtain the organic compound M7.

[0175] The molecular formula of the organic compound M7 is C 27 H 27 N4O3Br3, and the nuclear magnetic hydrogen spectrum parameters of the organic compound M7 are as follows. 1 H NMR (500 MHz, Chloroform-d) δ 7.84-7.78 (m, 6H), 7.48 (s, 3H), 7.24-7.19 (m, 6H), 1.82 (s, 18H).

[0176] Example 10

[0177] The embodiment of the present application provides an organic compound and a synthesis method thereof, and the synthesis method of the organic compound is different from that of the embodiment 1, wherein the chloroacetyl chloride in the step S3 is replaced by bromoacetyl bromide to obtain the organic compound M6.

[0178] The molecular formula of the organic compound M8 is C 24 H21 N4O3BrCl2, the nuclear magnetic hydrogen spectrum parameters of the organic compound M8 are: 1 H NMR (500 MHz, Chloroform-d) δ 9.18 (s, 3H), 7.83-7.77 (m, 6H), 7.24-7.19 (m, 6H), 4.21 (s, 6H).

[0179] Example 11

[0180] The embodiment of the present application provides an organic compound and a synthesis method thereof, and the synthesis method of the organic compound is different from that of the embodiment 1 in that 20 uL of chloroacetyl chloride in step S3 is replaced by 5 uL of 2-bromoisobutyryl bromide and 10 uL of 2-bromoisobutyryl chloride, so that the organic compound M9 is obtained.

[0181] The molecular formula of the organic compound M9 is: 24 H 21 N4O3Br2Cl, the nuclear magnetic hydrogen spectrum parameters of the organic compound M9 are: 1 H NMR (500 MHz, Chloroform-d) δ 7.84-7.78 (m, 6H), 7.48 (s, 3H), 7.24-7.19 (m, 6H), 1.82 (s, 18H).

[0182] Example 12

[0183] The embodiment of the present application provides an organic compound and a synthesis method thereof, and the synthesis method of the organic compound is different from that of the embodiment 1 in that the tri-(4-bromophenyl) amine in step S1 is replaced by CAS: 72393-15-8, 20 uL of chloroacetyl chloride in step S3 is replaced by 5 uL of bromoacetyl bromide and 10 uL of chloroacetyl chloride, so that the organic compound M10 is obtained.

[0184] The molecular formula of the organic compound M10 is: 27 H 27 N4O3BrCl2, the nuclear magnetic hydrogen spectrum parameters of the organic compound M10 are: 1 H NMR (500 MHz, Chloroform-d) δ 7.38-7.30 (m, 9H), 7.02-6.96 (m, 6H), 4.46 (dt, J=5.5, 0.9 Hz, 6H), 3.83 (s, 6H).

[0185] Example 13

[0186] The embodiment of the present application provides an organic compound and a synthesis method thereof, and the synthesis method of the organic compound is different from that of the embodiment 1, wherein the chloroacetyl chloride in the step S3 is replaced by N-chlorotrichloroacetamide to obtain the organic compound M11:

[0187] The molecular formula of the organic compound M11 is C 30 H 21 N4O3Cl9, and the nuclear magnetic hydrogen spectrum parameters of the organic compound M11 are: 1 H NMR (500 MHz, Chloroform-d) δ 7.84-7.78 (m, 6H), 7.48 (s, 3H), 7.24-7.19 (m, 6H), 1.82 (s, 18H).

[0188] Preparation and characterization of the QLED device

[0189] The preparation method of the QLED device using the organic compound is described in detail below by means of a specific device embodiment.

[0190] The preparation method of the QLED device using the organic compound M1 as the modification layer material is taken as an example, and the prepared QLED device is denoted as "device embodiment 1", and the structure of the device embodiment 1 is as shown in the figure. Figure 1 The preparation method of the device embodiment 1 comprises the following steps.

[0191] S1, a substrate with an ITO anode with a thickness of 80 nm is provided, the ITO plated substrate is ultrasonically cleaned with acetone and ethanol for 15 min, then cleaned with deionized water again, then dried on a heating plate at 150 DEG C for 10 min, and finally subjected to ultraviolet irradiation for 20 min to improve the ITO work function and surface energy, to obtain an anode 1;

[0192] S2, spin 8 mg / mL TFB at a speed of 3000 rpm for 30 seconds, and then heat at 120 DEG C for 10 min to obtain a hole functional layer 2;

[0193] S3, spin the CdZnSe quantum dot material with a concentration of 10 mg / mL at a speed of 1500 rpm for 30 s, and then anneal at 100 DEG C for 5 min to obtain an excitation layer 3;

[0194] S4, the organic compound M1 is dissolved in 1,1-dichloroethane, ultrasonically dispersed for 10 min to prepare a solution with a concentration of 10 mg / ml, the solution is spin-coated at a speed of 4000 rpm to form a thickness of 8 nm, and then subjected to UV irradiation for 10 min to obtain a modification layer 4;

[0195] S5, spin-coating 30 mg / mL ZnO-ethanol solution at 3000 rpm for 30 seconds, followed by heating at 100°C for 15 minutes to obtain an electron transport layer 5;

[0196] S6, by thermal evaporation, vacuum degree less than or equal to 3x10 -4 Pa, evaporating Ag at a speed of 1 angstrom / second for 200 seconds to obtain a cathode 6 with a thickness of 20 nm.

[0197] QLED-1 was prepared.

[0198] Further, referring to the preparation method of device embodiment 1, compounds M2-M11 were respectively used as the modification layer material in the QLED device to correspondingly prepare device embodiments 2-11; again, referring to the preparation method of device embodiment 1, step S4 was omitted to correspondingly prepare device comparative example 1. It can be understood that in the preparation methods of device embodiments 1-8, the experimental conditions are the same except that the materials of the modification layers are different; in the preparation method of device comparative example 1, the experimental conditions are the same except that step S4 is not included.

[0199] In this application, the characteristics of device embodiments 1-11 and device comparative example 1 were characterized, and the corresponding luminous efficiency CE (cd / A) and T95 lifetime (1000 nit) of the devices were measured, as shown in Table 1.

[0200] Table 1:

[0201] CE (cd / A) T95 lifetime (1000 nit) Device Example 1 203.7 7.31 Device Example 2 154.0 6.24 Device Example 3 144.3 6.06 Device Example 4 127.6 5.53 Device Example 5 141.2 6.03 Device Example 6 195.4 7.09 Device Example 7 180.5 6.88 Device Example 8 198.4 7.11 Device Example 9 140.7 5.87 Device Example 10 181.4 7.01 Device Example 11 129.4 5.43 Device Comparative Example 1 87.3 4.53

[0202] As can be seen from Table 1, device embodiments 1-11 have different degrees of significant improvement in luminous efficiency and lifetime compared to device comparative example 1, and the main reason may be that the organic compounds in this application have a good planar structure, and the presence of amide groups and L2 groups such as halogenated hydrocarbons can chelate adjacent film layer surface uncoordinated metals, improve film layer surface defects, and thus improve device luminous efficiency and service life.

[0203] The above has described the embodiments of the present application in detail, and the specific examples have been applied to the principles and implementation modes of the present application. The above description of the embodiments is only used to help understand the method and core idea of the present application; at the same time, for those skilled in the art, according to the idea of the present application, the specific implementation mode and application range will be changed, and the above description should not be understood as limiting the present application.

Claims

1. An organic compound, characterized by, comprising a compound as represented by the general formula (1): wherein R z , R s and R t are each independently at each occurrence selected from Ar1is independently selected at each occurrence from an unsubstituted or at least one R-substituted aryl group having 6 to 30 ring atoms, or an unsubstituted or at least one R-substituted heteroaryl group having 5 to 30 ring atoms, or a combination thereof; the heteroatoms in the heteroaryl group are independently selected at each occurrence from one or more of N, S, O, P, and Si, and the number of heteroatoms in the heteroaryl group is independently selected at each occurrence from 1 to 20; L1is independently selected at each occurrence from a single bond, an unsubstituted or at least one R-substituted C1-C30 aliphatic chain, a hydroxyl group, an aldehyde group, a thiol group, an ether group, an ester group, an amino group, a carbonyl group, a nitro group, a halogen; L2is independently selected at each occurrence from an unsubstituted or at least one R-substituted C1-C30 aliphatic chain, a hydroxyl group, an aldehyde group, a thiol group, an ether group, an ester group, an amino group, a carbonyl group, or a nitro group; R is independently selected at each occurrence from hydrogen, deuterium, a halogen, a hydroxyl group, a carboxyl group, a nitro group, a sulfonic acid group, a thiol group, a cyano group, an aldehyde group, or an amide group, or a combination thereof.

2. The organic compound according to claim 1, characterized by Ar1is independently selected at each occurrence from the following groups: wherein X is independently selected at each occurrence from CR1or NR1, R 11 each occurrence is independently selected from hydrogen, deuterium, halogen, hydroxyl, carboxyl, nitro, sulfonic acid group, thiol, cyano, aldehyde, amido, C1-C30 aliphatic chain hydrocarbyl unsubstituted or substituted with at least one R, C1-C30 aliphatic chain hydrocarbyloxy unsubstituted or substituted with at least one R, C3-C30 aliphatic cyclic hydrocarbyl unsubstituted or substituted with at least one R, C3-C30 aliphatic heterocyclic hydrocarbyl unsubstituted or substituted with at least one R, ring atom number 6 to 30 aryl unsubstituted or substituted with at least one R, ring atom number 6 to 30 aryloxy unsubstituted or substituted with at least one R, ring atom number 5 to 30 heteroaryl unsubstituted or substituted with at least one R, or ring atom number 5 to 30 heteroaryloxy unsubstituted or substituted with at least one R, or a combination thereof; the heteroatoms in the aliphatic heterocyclic hydrocarbyl, the heteroaryl, and the heteroaryloxy are independently selected from one or more of N, S, O, P, and Si, and the number of the heteroatoms in the aliphatic heterocyclic hydrocarbyl, the heteroaryl, and the heteroaryloxy are independently selected from 1 to 20; Y is independently selected at each occurrence from S, N, O, an unsubstituted or at least one R-substituted C1-C30 aliphatic chain, an unsubstituted or at least one R-substituted C3-C30 aliphatic cyclic group, or an unsubstituted or at least one R-substituted C3-C30 aliphatic heterocyclic group.

3. The organic compound according to claim 2, characterized by Further, the general formula (1) is selected from the general formula (2-1) or the general formula (2-2):

4. The organic compound according to claim 3, characterized by Ar1is independently selected at each occurrence from an unsubstituted or at least one R-substituted aryl group having 6 to 10 ring atoms; and / or L1is independently selected at each occurrence from a single bond, an unsubstituted or at least one R-substituted C1-C8 linear alkyl group, an unsubstituted or at least one R-substituted C3-C8 branched alkyl group; and / or L2is independently selected at each occurrence from a C1-C30 halogenated alkyl group.

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

6. A method of synthesizing an organic compound, characterized by, comprising the following steps: mixing and reacting the first compound and the second compound in a first solvent to obtain the organic compound; wherein the structure of the first compound is represented by the general formula (I): wherein R m , R n , and R q are each independently selected at each occurrence from Ar2is independently selected at each occurrence from an unsubstituted or at least one R-substituted aryl group having 6 to 30 ring atoms, or an unsubstituted or at least one R-substituted heteroaryl group having 5 to 30 ring atoms, or a combination thereof; the heteroatoms in the heteroaryl group are independently selected at each occurrence from one or more of N, S, O, P, and Si, and the number of heteroatoms in the heteroaryl group is independently selected at each occurrence from 1 to 20; L3is independently selected at each occurrence from a single bond, an unsubstituted or at least one R-substituted C1-C30 aliphatic chain, a hydroxyl group, an aldehyde group, a thiol group, an ether group, an ester group, an amino group, a carbonyl group, a nitro group, a halogen; R is independently selected at each occurrence from deuterium, a halogen, a hydroxyl group, a carboxyl group, a nitro group, a sulfonic acid group, a thiol group, a cyano group, an aldehyde group, or an amide group, or a combination thereof. wherein the second compound has a structure according to Formula (II): wherein L4 is selected from a C1-C30 aliphatic chain hydrocarbon group that is unsubstituted or substituted with at least one R, a hydroxyl group, an aldehyde group, a thiol group, an ether group, an ester group, an amino group, a carbonyl group, or a nitro group; L5 is selected from a halogen; R is independently selected at each occurrence from deuterium, a halogen, a hydroxyl group, a carboxyl group, a nitro group, a sulfonic acid group, a thiol group, a cyano group, an aldehyde group, or an amide group, or a combination of these groups.

7. The method for synthesizing an organic compound according to claim 6, characterized in that, Ar2 is independently selected at each occurrence from the following groups: wherein X is independently selected at each occurrence from CR1 or NR1, and R1 is independently selected at each occurrence from hydrogen, deuterium, a halogen, a hydroxyl group, a carboxyl group, a nitro group, a sulfonic acid group, a thiol group, a cyano group, an aldehyde group, an amide group, a C1-C30 aliphatic chain hydrocarbon group that is unsubstituted or substituted with at least one R, a C1-C30 aliphatic chain hydroxyl group that is unsubstituted or substituted with at least one R, a C3-C30 aliphatic cyclic hydrocarbon group that is unsubstituted or substituted with at least one R, a C3-C30 aliphatic heterocyclic hydrocarbon group that is unsubstituted or substituted with at least one R, an aryl group having 6 to 30 ring atoms that is unsubstituted or substituted with at least one R, an aryloxy group having 6 to 30 ring atoms that is unsubstituted or substituted with at least one R, a heteroaryl group having 5 to 30 ring atoms that is unsubstituted or substituted with at least one R, or a heteroaryloxy group having 5 to 30 ring atoms that is unsubstituted or substituted with at least one R, or a combination of these groups; the heteroatoms in the aliphatic heterocyclic hydrocarbon group, the heteroaryl group, and the heteroaryloxy group are independently selected from one or more of N, S, O, P, and Si, and the number of heteroatoms in the aliphatic heterocyclic hydrocarbon group, the heteroaryl group, and the heteroaryloxy group are independently selected from 1 to 20; Y is independently selected at each occurrence from S, N, O, a C1-C30 aliphatic chain hydrocarbon group that is unsubstituted or substituted with at least one R, a C3-C30 aliphatic cyclic hydrocarbon group that is unsubstituted or substituted with at least one R, or a C3-C30 aliphatic heterocyclic hydrocarbon group that is unsubstituted or substituted with at least one R; and / or a third compound is also provided, the third compound is mixed with the first and second compounds in the first solvent, the third compound comprises an organic base; and / or the first solvent comprises an organic solvent. 8.The method of claim 7, wherein the organic compound is selected from the group consisting of: and . Further, the Formula (I) is selected from Formula (I-1) or Formula (I-2):

9. The method for synthesizing an organic compound according to claim 8, characterized in that, Ar2 is independently selected at each occurrence from an aryl group having 6 to 10 ring atoms that is unsubstituted or substituted with at least one R; and / or L3 is independently selected at each occurrence from a single bond, a C1-C8 straight chain hydrocarbon group that is unsubstituted or substituted with at least one R, or a C3-C8 branched chain hydrocarbon group that is unsubstituted or substituted with at least one R; and / or L4 is independently selected at each occurrence from a C1-C30 halogenated hydrocarbon group.

10. The method for synthesizing an organic compound according to claim 7, characterized in that, the third compound is selected from NR1R2R3, R1, R2, and R3 are independently selected at each occurrence from hydrogen, deuterium, a C1-C30 aliphatic chain hydrocarbon group that is unsubstituted or substituted with at least one R.

11. The method for synthesizing an organic compound according to claim 6, characterized in that, Before the step of mixing and reacting the first compound and the second compound in the first solvent, further comprising a step of synthesizing the first compound: A first precursor having a general formula (III) and a second precursor having a general formula (IV) are provided, the first precursor and the second precursor are dissolved in a precursor solvent, and heated to obtain a first intermediate product: The fourth compound and the first intermediate product are dissolved in a second intermediate solvent to obtain the first compound; the fourth compound is selected from one or more of hydrazine hydrate, borane, diisobutylaluminum hydride, lithium aluminum hydride, sodium borohydride, and potassium borohydride; The general formula (III) is: wherein Z m , Z n , and Z q are each independently selected at each occurrence from Ar2-L3; The general formula (IV) is:

12. The method for synthesizing an organic compound according to claim 11, characterized in that, The step of mixing the first precursor and the second precursor specifically comprises: mixing the first precursor, the second precursor, CuI, a strong base weak acid salt and dissolved in the precursor solvent; and / or The first solvent includes dichloromethane; and / or The precursor solvent is selected from one or more of dioxane, dimethyl sulfoxide, toluene, and xylene; and / or The boiling point of the second intermediate solvent is less than or equal to 100°C; R4 and R5 are each independently selected from a C1-C30 aliphatic chain hydrocarbon group that is unsubstituted or substituted with at least one R.

13. An optoelectronic device, characterized in that Comprise a first electrode, a functional layer, and a second electrode, which are arranged in a stack; The first electrode and the second electrode are each independently selected from a doped metal oxide electrode, a composite electrode, a graphene electrode, a carbon nanotube electrode, a metal element electrode, or an alloy electrode, the doped metal oxide electrode is selected from one or more of indium-doped tin oxide, fluorine-doped tin oxide, antimony-doped tin oxide, aluminum-doped zinc oxide, gallium-doped zinc oxide, indium-doped zinc oxide, magnesium-doped zinc oxide, aluminum-doped magnesium oxide, and cadmium-doped zinc oxide, the composite electrode is selected from AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, TiO2 / Ag / TiO2, TiO2 / Al / TiO2, ZnS / Ag / ZnS, ZnS / Al / ZnS, Ca / Al, LiF / Ca, LiF / Al, BaF2 / Al, CsF / Al, CaCO3 / Al, or BaF2 / Ca / Al, the metal element electrode is selected from one or more of Ag, Ni, Pt, Au, Ir, Cu, Mo, Al, Ca, Mg, and Ba, and the alloy electrode is selected from an Au:Mg alloy electrode or an Ag:Mg alloy electrode; and / or The functional layer further comprises a hole functional layer, an excitation layer, a modification layer, and an electron functional layer arranged in a stack. ​ ​ 14. An optoelectronic device according to claim 13, wherein, ​ ​ The material of the hole functional layer includes one or more of 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'-di(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)benzidine)], poly(N-vinylcarbazole) and derivatives thereof, N,N'-di(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4-4'-diamine, spiro NPB, poly(phenylenevinylene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene], poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene], 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene, 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)benzidine], 1,3-bis(carbazol-9-yl)benzene, polyaniline, polypyrrole, poly(p)phenylenevinylene, aromatic tertiary amine, polynuclear aromatic tertiary amine, 4,4'-bis(p-carbazolyl)-1,1'-biphenyl compound, N,N,N',N'-tetraarylbenzidine, PEDOT:PSS and derivatives thereof, polymethacrylate and derivatives thereof, poly(9,9-octylfluorene) and derivatives thereof, poly(spirofluorene) and derivatives thereof, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene, PEDOT, PEDOT:PSS, derivatives of PEDOT:PSS doped with s-MoO3, 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, tetracyanoquinodimethane, doped graphene, non-doped graphene, C60, copper phthalocyanine, the second doped metal oxide particles, the second non-doped metal oxide particles, the metal sulfide, and the metal nitride; and / or The modification layer includes the organic compound of any one of claims 1-5, or an organic compound synthesized by the synthetic method of the organic compound of any one of claims 6-12; and / or The material of the excitation layer comprises 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 independently selected from one or more of II-VI compounds, IV-VI compounds, III-V compounds and I-III-VI compounds, the II-VI compounds comprise one or more of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and HgZnSTe, the IV-VI compounds comprise one or more of SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, SnPbSTe, the III-V compounds comprise one or more of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs and InAlPSb, the I-III-VI compounds comprise one or more of CuInS2, CuInSe2 and AgInS2; the perovskite semiconductor material comprises doped or non-doped inorganic perovskite semiconductor or organic-inorganic hybrid perovskite semiconductor, the general structure of the inorganic perovskite semiconductor is AMX3, wherein A is Cs + ion, M is a divalent metal cation, comprising 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 Cl - , Br - , I - ; the structure general formula of the organic-inorganic hybrid perovskite type semiconductor is BMX3, wherein B is an organic amine cation, including CH3(CH2) n-2 NH3 + or [NH3(CH2) n NH3] 2+ , wherein n≥2, M is a divalent metal cation, including one or more of 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 Cl - , Br - , I - ; and / or The material of the electronic functional layer includes one or more of an inorganic electronic functional material including one or more of the first doped metal oxide particles, the first non-doped metal oxide particles, the Group IIB-VIA semiconductor material, the Group IIIA-VA semiconductor material, and the Group IB-IIIA-VIA semiconductor material, and an organic electronic functional material including one or more of a quinoxaline compound, an imidazole compound, a triazine compound, a fluorene-containing compound, a hydroxyquinoline compound, and a fullerene derivative.

15. A display device comprising: A photoelectric device produced by a production method of a photoelectric device as claimed in claim 13 or 14.

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