Organic compound and preparation method thereof, electron transport material, photoelectric device and display device

Abstract

The invention discloses an organic compound and a preparation method thereof, an electron transport material, a photoelectric device and a display device. The organic compound provided by the invention is a disulfuryl benzopyrrole organic compound with a benzotriazole structure, and the compound has ultraviolet absorption performance, can absorb ultraviolet rays and avoid ultraviolet light damage, and has better light stability; in addition, the compound has good electron injection capability and charge transfer performance, and can effectively adjust the LUMO energy level of the compound.

Description

Technical Field

[0001] The present application relates to the field of organic materials, and in particular to an organic compound and a preparation method thereof, an electron transport material, an optoelectronic device and a display device. Background Art

[0002] Electron transport materials refer to materials that can accept negatively charged electron carriers and transport them. Semiconductor materials with high electron affinity and ionic potential (i.e., n-type semiconductors) are usually used as electron transport materials. Currently, electron transport materials mainly use n-type inorganic nanomaterials, such as zinc oxide (ZnO), zirconium dioxide (ZrO2), molybdenum disulfide (MoS), etc.

[0003] In actual applications, various application scenarios are often encountered. For example, some situations require the use of electron transport materials with relatively small electron mobility, or situations that require resistance to ultraviolet light exposure. Currently common electron transport materials are difficult to meet the needs of more and more application scenarios. Therefore, there is an urgent need to develop new electron transport materials and expand the types of electron transport materials. Summary of the invention

[0004] In view of this, the present application provides an organic compound and a preparation method thereof, an electron transport material, an optoelectronic device and a display device.

[0005] In a first aspect, the present invention provides an organic compound having a structure shown in formula (I):

[0006]

[0007] wherein R1, R2, and R3 are independently selected from H, D, a halogen atom, a substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C7~C 36 Alkylphenyl, substituted or unsubstituted C7~C 36 One or more of alkoxyphenyl;

[0008] Ar1 and Ar2 are each independently selected from the following structures:

[0009]

[0010] Wherein, X is CR6R7, S, NR8 or O; M is NR9, O, SiR 10 R 11 or S;

[0011] R4 and R5 are each independently selected from substituted or unsubstituted C1 to C 30 Alkyl, substituted or unsubstituted C1~C30 A combination of one or more of alkoxy;

[0012] R6 to R 11 Each independently selected from H, D, substituted or unsubstituted C1-C 30 A combination of one or more of an alkyl group, a substituted or unsubstituted aryl group having 6 to 60 ring atoms;

[0013] m is 0 or 1;

[0014] n1 and n2 are each independently selected from integers from 0 to 5;

[0015] n3 and n4 are each independently selected from integers of 0-4.

[0016] In a second aspect, the present invention also provides a method for preparing an organic compound, comprising the following steps:

[0017] Compound 1 and compound a are mixed and subjected to a first reaction to obtain compound 2;

[0018] The compound 2 is mixed with a reducing agent to carry out a second reaction to obtain a compound 3;

[0019] The compound 3 and the compound b are mixed and subjected to a third reaction to obtain a compound 4;

[0020] The compound 4 is mixed with an oxidant to carry out a fourth reaction to obtain a compound 5;

[0021] The compound 5 is mixed with the compound c to carry out a fifth reaction to obtain an organic compound 6;

[0022] Among them, compound 1, compound 2, compound 3, compound 4, compound 5, organic compound 6, compound a, compound b, and compound c have the following structural formulas respectively:

[0023]

[0024] wherein Y, at each occurrence, is independently selected from a halogen group;

[0025] R represents R2 or R3, Ar represents Ar1 or Ar2;

[0026] R1, R2, and R3 are each independently selected from H, D, a halogen atom, a substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C7~C 36 Alkylphenyl, substituted or unsubstituted C7~C 36 One or more of alkoxyphenyl;

[0027] Ar1 and Ar2 are each independently selected from the following structures:

[0028]

[0029] Wherein, X is CR6R7, S, NR8 or O; M is NR9, O, SiR 10 R 11 or S;

[0030] R4 and R5 are each independently selected from substituted or unsubstituted C1 to C 30 Alkyl, substituted or unsubstituted C1~C 30 A combination of one or more of alkoxy;

[0031] R6 to R 11 Each independently selected from H, D, substituted or unsubstituted C1-C 30 A combination of one or more of an alkyl group, a substituted or unsubstituted aryl group having 6 to 60 ring atoms;

[0032] m is 0 or 1;

[0033] n1 and n2 are each independently selected from integers from 0 to 5;

[0034] n3 and n4 are each independently selected from integers of 0-4.

[0035] In a third aspect, the present application further proposes an electron transport material, comprising the organic compound as described above, or an organic compound prepared by the method for preparing the organic compound as described above.

[0036] In a fourth aspect, an embodiment of the present application further provides a photoelectric device, comprising an anode, an electronic functional layer and a cathode, wherein the material of the electronic functional layer comprises the above-mentioned organic compound, or comprises an organic compound prepared by the above-mentioned method for preparing the organic compound, or comprises the above-mentioned electron transport material.

[0037] In a fifth aspect, an embodiment of the present application further provides a display device, comprising the above-mentioned optoelectronic device.

[0038] The present application provides an organic compound, which is a bissulfone benzopyrrole organic compound with a benzotriazole structure. The compound has ultraviolet absorption properties, can absorb ultraviolet rays, avoid ultraviolet light damage, and has good photostability; in addition, the compound has good electron injection ability and charge transfer performance, and can effectively adjust its own LUMO energy level. BRIEF DESCRIPTION OF THE DRAWINGS

[0039] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings required for use in the description of the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present application. For those skilled in the art, other drawings can be obtained based on these drawings without creative work.

[0040] Figure 1 It is a structural schematic diagram of an embodiment of a photoelectric device provided in the present application.

[0041] Reference numerals: 100 - optoelectronic device, 10 - anode, 20 - cathode, 30 - electron functional layer, 40 - light emitting layer, 50 - hole functional layer, 51 - hole injection layer, 52 - hole transport layer. DETAILED DESCRIPTION

[0042] The following will be combined with the drawings in the embodiments of the present application to clearly and completely describe the technical solutions in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative work belong to the scope of protection of the present application. In addition, it should be understood that the specific implementation methods described herein are only used to illustrate and explain the present application, and are not used to limit the present application. In the present application, unless otherwise specified, the directional words such as "upper" and "lower" used are specifically the directions of the drawings in the accompanying drawings. In addition, in the description of the present application, the term "including" means "including but not limited to". Various embodiments of the present application may exist in the form of a range; it should be understood that the description in the form of a range is only for convenience and simplicity, and should not be understood as a hard limit 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, description of a range from 1 to 6 should be considered to have specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the stated 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 numeral (fractional or integral) within the stated range.

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

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

[0045] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0046] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0047] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted and no additional definition is provided, "substituted" means that the hydrogen of the compound or group is replaced by the following substituents: a deuterium atom, a halogen, a hydroxyl group, a nitro group, a cyano group, an isocyano group, an amino group, an azido group, an amidino group, a hydrazine group, a hydrazone group, a carbonyl group, a carbamoyl group, a thiol group, an ester group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a silyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C30 aryl group, a C7-C30 aralkyl group, a C1-C30 alkoxy group, a C1-C20 heteroalkyl group, a C3-C20 heterocyclic group, a C3-C20 heteroaralkyl group, a C3-C30 cycloalkyl group, a C3-C15 cycloalkenyl group, a C6-C15 cycloalkynyl group, a C3-C30 heterocycloalkyl group, and a combination of one or more thereof.

[0048] In the present application, "ring atoms" means the number of atoms of the ring atoms constituting the ring itself in a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) formed by atoms bonding to form a ring, i.e., the number of atoms forming the ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same is true for the "ring atoms" described below, unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0049] In the present application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aromatic groups having 6 to 40 ring atoms" refers to aromatic groups containing 6 to 40 ring atoms, and the aromatic group can be optionally further substituted. Preferably, substituted or unsubstituted aromatic groups having 6 to 30 ring atoms are preferred, more preferably substituted or unsubstituted aromatic groups having 6 to 18 ring atoms are preferred, and particularly preferably substituted or unsubstituted aromatic groups having 6 to 14 ring atoms are preferred, and the aromatic group can be optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, naphthyl, fluorenyl, dinaphthylenyl, acenaphthene and derivatives thereof. It is understandable that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0050] In the present application, "heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aromatic group, and the non-carbon atom can be an N atom, an O atom, an S atom, an Si atom, a P atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted; suitable examples include, but are not limited to: thienyl, furanyl, pyrrolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, Triazine, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothiophenyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primary pyridyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0051] In the present application, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Phrases containing this term, such as "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence may 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, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl 2-Hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, 2-tridecyl, 2-tetradecyl, 2-pentadecyl, 2-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-octylhexadecyl, 2-octadecyl, 2-octadecyl, 2-nonadecyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, 2-heneicosyl, 2-heneicosyl, 2-heconicosyl, 2-docosyl, 2-tricosyl, 2-tetracosyl, 2-pentacosyl, 2-hexacosyl, 2-heptacosyl, 2-octacosyl, 2-nonacosyl, 2-triacontyl, etc.

[0052] In this application, “-C n H 2n+1 "Unless otherwise specified or limited, it means a straight-chain alkyl group. For example, -C4H9 means n-butyl.

[0053] In the present application, "alkoxy" refers to a group having a structure of "-O-alkyl", i.e., an alkyl group as defined above is connected to other groups via an oxygen atom. Phrases containing the term, suitable examples include, but are not limited to, methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt) and tert-butoxy (-OC(CH3)3 or -OtBu).

[0054] In the present application, "alkylphenyl" is a phenyl group substituted with an alkyl group, and its structural formula can be "-phenyl-alkyl", and the alkyl group can refer to the description above. Suitable examples include, but are not limited to, tolyl, ethylphenyl, etc. 36 C7~C 36 is the number of carbon atoms in the entire group.

[0055] In the present application, "alkoxyphenyl" is a phenyl group substituted with an alkoxy group, and the alkoxy group can refer to the description above. Suitable examples include, but are not limited to: wait.

[0056] In the present application, "'*' connected to a single bond" indicates a connection site or a fusion site. When a connection site is not specified in a group, it indicates that an optional connection site in the group can be used as a connection site. For example, In the embodiment, any connectable sites on the two benzene rings and any connectable sites on M can be used as the connecting sites for connecting with the N atom in the main skeleton structure; it is understood that when M is used as the connectable site, M is N or SiR 10 In addition, it can also be when M is NR9, or SiR 10 R 11 When, R9, R 10 or R 11 as a connection site.

[0057] In the present application, when the fusion site is not specified in the group, it means that the fusion site in the group is optionally fused as the fusion site, and preferably two or more sites in the ortho position in the group are fused sites; for example, Representative: Any two sites in the ortho position on the benzene ring can serve as fusion sites and condense with the triazole ring containing three nitrogen atoms.

[0058] In the present application, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring. R4 can be connected to any substitutable site in the benzene ring. Further, in the present application, when the same substituent appears multiple times, it can be independently selected from different groups; if the above general formula can contain n1 R4, each R4 can be independently selected from different groups.

[0059] The terms "combination thereof", "any combination thereof", "any combination thereof" and the like used in this application include all suitable combinations of any two or more of the listed items.

[0060] The present application provides an organic compound having a structure shown in formula (I):

[0061]

[0062] wherein R1, R2, and R3 are independently selected from H, D, a halogen atom, a substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C7~C 36 Alkylphenyl, substituted or unsubstituted C7~C 36One or more of alkoxyphenyl;

[0063] Ar1 and Ar2 are each independently selected from the following structures:

[0064]

[0065] Wherein, X is CR6R7, S, NR8 or O; M is NR9, O, SiR 10 R 11 or S;

[0066] R4 and R5 are each independently selected from substituted or unsubstituted C1 to C 30 Alkyl, substituted or unsubstituted C1~C 30 A combination of one or more of alkoxy;

[0067] R6 to R 11 Each independently selected from H, D, substituted or unsubstituted C1-C 30 A combination of one or more of an alkyl group, a substituted or unsubstituted aryl group having 6 to 60 ring atoms;

[0068] m is 0 or 1; when m is 0, the two benzene rings are connected by a single bond, and the structural formula is as follows:

[0069]

[0070] n1 and n2 are each independently selected from integers of 0 to 5, for example, 0, 1, 2, 3, 4 or 5;

[0071] n3 and n4 are each independently selected from integers of 0 to 4, for example, 0, 1, 2, 3 or 4.

[0072] In this embodiment, the organic compound is a bissulfone benzopyrrole organic compound. Since it has multiple electron-rich nitrogen atoms and sulfur atoms, it has good electron injection ability. The introduction of the sulfone group can, on the one hand, effectively passivate the lone pair of electrons of the sulfur atom, reduce the influence of light and heat on the free electrons, and improve the stability of the material; on the other hand, it can reduce the LUMO energy level of the material, reduce the band gap difference between the electrode and the electron transport layer, and make electrons more effectively injected. At the same time, the band gap difference between the quantum dot and the electron transport layer increases, increasing the difficulty of injection, thereby reducing the efficiency and stability of the quantum dot due to excessive electron injection. Imbalance caused by carriers; in addition, its large conjugated linear structure itself is conducive to electron transport.

[0073] Furthermore, when the organic compound is used as an electronic functional material in the optoelectronic device 100, the organic compound has good matching with commonly used hole transport materials (such as TFB, PVK, etc.). When used together, the balance between hole injection and electron injection in the device is good, which is beneficial to improving the carrier balance of the device, thereby improving the luminous efficiency of the optoelectronic device 100; in addition, the organic compound of the present application has a stable molecular structure and good stability, which helps to improve the life of the optoelectronic device 100.

[0074] In addition, the organic compound of the present application has good ultraviolet absorption performance, which can absorb the ultraviolet rays generated during the device preparation process, reduce the damage of ultraviolet rays to the material, and improve the photostability of the device.

[0075] In some embodiments, the two connection sites a1 and b1 on the triazole can be used as fusion sites, and the corresponding connection sites on the benzene ring, such as any two adjacent sites among c1, d1, e1, and f1, can be used as fusion sites, and a1 and b1 are fused with the fusion sites on the benzene ring to form a fused structure; in other embodiments, the two connection sites a2 and b2 on the triazole can be used as fusion sites, and the corresponding connection sites on the benzene ring, such as any two adjacent sites among c2, d2, e2, and f2, can be used as fusion sites, and a2 and b2 are fused with the fusion sites on the benzene ring to form a fused structure.

[0076]

[0077] In some embodiments, a1, b1, d1, and e1 serve as fusion sites, and a2, b2, d2, and e2 serve as fusion sites. Accordingly, the organic compound has a structure shown in formula (II):

[0078]

[0079] Understandable, C7~C 36 In alkylphenyl, the benzene ring itself has 6 carbon atoms, and the alkyl group is 1 to 30. 36 In the alkoxyphenyl group, the benzene ring itself has 6 C atoms, and the number of carbon atoms in the alkoxy group is 1 to 30.

[0080] In some embodiments, R1, R2, and R3 are each independently selected from H, D, unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C7~C 36 Alkylphenyl, substituted or unsubstituted C7~C 36Further, in some embodiments, R1, R2, and R3 are each independently selected from substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1~C 12 Alkoxy, substituted or unsubstituted C7~C 18 Alkylphenyl, substituted or unsubstituted C7~C 18 A combination of one or more groups in alkoxyphenyl; further, in some embodiments, R1, R2, and R3 are each independently selected from C1 to C 12 Straight chain or branched alkyl, C7~C 18 A type of alkoxyphenyl.

[0081] In one embodiment, at least one of R1, R2, and R3 is selected from C n H 2n+1 Any one of the foregoing, wherein n is an integer of 6 to 12. A relatively long alkyl chain can improve the solubility of the organic compound to a certain extent.

[0082] In one embodiment, R1, R2, and R3 may be selected from the same substituent or may be selected from different substituents.

[0083] In another embodiment, among R1, R2, and R3, at least R2 and R3 are selected from the same substituent, which helps to reduce the difficulty of synthesizing the organic compound.

[0084] It is understood that in "substituted or unsubstituted", when substituted, the substituent may be any common substituent in the art, see the above term explanation for details. In some embodiments, the substituent is selected from a combination of one or more of hydrogen, deuterium, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, and cyano; further, the substituent is selected from hydrogen or deuterium.

[0085] In some embodiments, Ar1 and Ar2 are selected from one of the following substituted or unsubstituted structures:

[0086]

[0087] Further, in some embodiments, Ar1 and Ar2 are each independently selected from one of the following structural formulas (1-1) to (1-13):

[0088]

[0089] In one embodiment, n1 and n2 are each independently selected from integers of 0 to 1, for example, they can be selected from 0 or 1. For example, n1 is 0 and n2 is 1; or, n1 is 1 and n2 is 0; or, n1 is 0 and n2 is 0; or, n1 is 1 and n2 is 1. In one embodiment, n3 and n4 are each independently selected from integers of 0 to 1, for example, they can be selected from 0 or 1. For example, n3 is 0 and n4 is 1; or, n3 is 1 and n4 is 0; or, n3 is 0 and n4 is 0; or, n3 is 1 and n4 is 1.

[0090] In some embodiments, Ar1 and Ar2 are the same. In some embodiments, Ar1 and Ar2 are different.

[0091] In some embodiments, R4 and R5 are each independently selected from substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C1~C 10 In some other embodiments, R4 and R5 are each independently selected from one of C1-C4 alkyl and C1-C4 alkoxy.

[0092] In some embodiments, R6 to R 11 Each independently selected from H, D, substituted or unsubstituted C1-C 10 A combination of one or more of an alkyl group, a substituted or unsubstituted aryl group having 6 to 10 ring atoms. 11 Each independently selected from H, D, C1-C 10 A combination of one or more of an alkyl group and an aryl group having 6 to 10 ring atoms. 11 Each is independently selected from one of H, D, C1-C4 alkyl and phenyl.

[0093] In some specific embodiments, the organic compound includes one or more of the following structural formulas:

[0094]

[0095]

[0096] The present application provides a method for preparing an organic compound, and the organic compound can be prepared through the following synthetic route.

[0097]

[0098] The preparation method comprises the following steps:

[0099] S10, mixing compound 1 and compound a, performing a first reaction, and obtaining compound 2;

[0100] S20, mixing the compound 2 with a reducing agent to perform a second reaction to obtain a compound 3;

[0101] S30, mixing the compound 3 and the compound b, and performing a third reaction to obtain a compound 4;

[0102] S40, mixing the compound 4 with an oxidant to perform a fourth reaction to obtain a compound 5;

[0103] S50, mixing the compound 5 with the compound c, and performing a fifth reaction to obtain an organic compound 6;

[0104] Among them, compound 1, compound 2, compound 3, compound 4, compound 5, organic compound 6, compound a, compound b, and compound c respectively have the structural formulas shown in the above synthesis route.

[0105] Wherein, Y, when it appears, is independently selected from a halogen group, such as -Cl, -Br or -I; R represents R2 or R3, Ar represents Ar1 or Ar2; R1, R2, and R3 are independently selected from H, D, a halogen atom, a substituted or unsubstituted C1 to C 30 Alkyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C7~C 36 Alkylphenyl, substituted or unsubstituted C7~C 36 One or more of alkoxyphenyl;

[0106] Ar1 and Ar2 are each independently selected from the following structures:

[0107]

[0108] Wherein, X is CR6R7, S, NR8 or O; M is NR9, O, SiR 10 R 11 or S; R4, R5 are each independently selected from substituted or unsubstituted C1~C 30 Alkyl, substituted or unsubstituted C1~C 30 A combination of one or more of alkoxy; R6 to R 11 Each independently selected from H, D, substituted or unsubstituted C1-C 30 A combination of one or more of an alkyl group and a substituted or unsubstituted aryl group having 6 to 60 ring atoms; m is 0 or 1; n1 and n2 are each independently selected from integers of 0 to 5; n3 and n4 are each independently selected from integers of 0 to 4.

[0109] In some embodiments, step S10 specifically includes: under the protection of an inert gas, mixing compound 1, compound a and a palladium catalyst under alkaline conditions, performing a first reaction, and obtaining compound 2.

[0110] Compound 1, compound A and palladium catalyst can undergo a Heck reaction under alkaline conditions, so that the benzotriazole structure is connected to pyrrolodithiophene to generate compound 2. It can be understood that the inert gas generally refers to protective gases such as nitrogen, helium, argon, etc., which can isolate or reduce water and oxygen in the reaction system.

[0111] The alkaline condition can be achieved by adding strong alkaline substances such as sodium hydroxide and potassium hydroxide. The alkaline condition can be that the pH of the entire solution system is greater than or equal to 9, for example, it can be pH9.0, pH9.3, pH9.5, pH9.8, pH10.0, pH10.5, pH11.0, etc. In some embodiments, the base is sodium hydroxide, and the molar ratio of the base to the compound 1 is 1: (2.2-4), for example, it can be 1:2.2, 1:2.5, 1:2.7, 1:3, 1:3.5, 1:3.8, 1:4 and values ​​between any two of the above values.

[0112] In the above steps, the palladium catalyst used can be a palladium catalyst commonly used in the art, such as tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), tetrakis(triphenylphosphine)palladium (pd(pph3)4), etc.

[0113] In some embodiments, the molar ratio of the compound 1 to the compound a is 1:(2.2-4); for example, it can be 1:2.2, 1:2.5, 1:2.7, 1:3, 1:3.5, 1:3.8, 1:4, and values ​​between any two of the above values. In some embodiments, the molar ratio of the compound 1 to the palladium catalyst is 1:(0.1-0.2); for example, it can be 1:0.1, 1:0.12, 1:0.15, 1:0.17, 1:0.18, 1:0.19, 1:0.2, and values ​​between any two of the above values.

[0114] In some embodiments, the reaction temperature of the first reaction is 150-170°C; for example, it can be 150°C, 155°C, 160°C, 165°C, 170°C, and values ​​between any two of the above values. In some embodiments, the reaction time of the first reaction is 8-12h; for example, it can be 8h, 8.5h, 9h, 9.5h, 10h, 10.5h, 11h, 12h, and values ​​between any two of the above values.

[0115] In step S20, the reducing agent may include, but is not limited to, one or more of trimethyl phosphite, triethyl phosphite, and tripropyl phosphite.

[0116] In some embodiments, the molar ratio of the compound 2 and the reducing agent is 1:(40-60); for example, it can be 1:(40-55), 1:(45-55), 1:(45-50), 1:(40-45), 1:(55-60); specifically, it can be 1:40, 1:45, 1:50, 1:55, 1:60 and values ​​between any two of the above values.

[0117] In some embodiments, the reaction temperature of the second reaction is 140-170°C; for example, it can be 140°C, 145°C, 150°C, 155°C, 160°C, 165°C, 170°C, and values ​​between any two of the above values.

[0118] In some embodiments, the reaction time of the second reaction is 12 to 24 hours; for example, it can be 12 hours, 15 hours, 18 hours, 20 hours, 22 hours, 24 hours, and a value between any two of the above values.

[0119] In order to further promote the reaction, the second reaction can be carried out in a solvent, and the solvent can be o-dichlorobenzene; in order to avoid affecting the reaction and reduce side reactions, the second reaction can be carried out under the protection of an inert gas.

[0120] In step S30, compound 3 and compound b undergo a carbon-carbon coupling reaction under alkaline conditions to generate compound 4.

[0121] Among them, the molar ratio of the compound 3 and the compound b can be 1:(2-4); for example, it can be 1:(2-3.5), 1:(2.5-3.5), 1:(2.5-3), 1:(3.5-4), etc.; specifically, it can be 1:2, 1:2.2, 1:2.5, 1:2.7, 1:3, 1:3.5, 1:3.8, 1:4 and values ​​between any two of the above values.

[0122] In some embodiments, the reaction temperature of the third reaction is 80-110°C; for example, it can be 80°C, 85°C, 90°C, 95°C, 100°C, 105°C, 110°C, and values ​​between any two of the above values. In some embodiments, the reaction time of the third reaction is 6-24h; for example, it can be 6h, 12h, 15h, 18h, 20h, 22h, 24h, and values ​​between any two of the above values.

[0123] In step S40: In some embodiments, the oxidant includes peroxide, and the peroxide includes one or more of hydrogen peroxide, potassium persulfate, and sodium persulfate.

[0124] In some embodiments, the molar ratio of the compound 4 to the oxidant is 1:(40-80); for example, it can be 1:(40-55), 1:(45-55), 1:(45-50), 1:(40-45), 1:(55-60), 1:(60-70), 1:(75-80); specifically, it can be 1:40, 1:45, 1:50, 1:55, 1:60, 1:65, 1:70, 1:75, 1:80 and values ​​between any two of the above values.

[0125] In some embodiments, the reaction temperature of the fourth reaction is 40-60°C; for example, it can be 40°C, 45°C, 50°C, 55°C, 60°C, and values ​​between any two of the above values. In some embodiments, the reaction time of the fourth reaction is 12-24h; for example, it can be 12h, 15h, 18h, 20h, 22h, 24h, and values ​​between any two of the above values.

[0126] In step S50:

[0127] In some embodiments, the molar ratio of compound 5 to compound c is 1:(2-4); for example, it can be 1:(2-3.5), 1:(2.5-3.5), 1:(2.5-3), 1:(3.5-4), etc.; specifically, it can be 1:2, 1:2.2, 1:2.5, 1:2.7, 1:3, 1:3.5, 1:3.8, 1:4 and values ​​between any two of the above values.

[0128] In some embodiments, the reaction temperature of the fifth reaction is 80-110°C; for example, it can be 80°C, 85°C, 90°C, 95°C, 100°C, 105°C, 110°C, and values ​​between any two of the above values. In some embodiments, the reaction time of the fifth reaction is 12-24h; for example, it can be 12h, 15h, 18h, 20h, 22h, 24h, and values ​​between any two of the above values.

[0129] In some embodiments, when the organic compound to be prepared has a structure represented by formula (II), correspondingly, in step S10, the compound a used may be a compound having the following structure (a-1);

[0130]

[0131] In some specific embodiments, the compound having structure (a-1) can be synthesized by the following steps:

[0132]

[0133] The synthesis steps are as follows:

[0134] 34mmol 1-bromo-2,4,5-trinitroamine (CAS: 89464-07-3) and 60ml acetic acid were added to a two-necked bottle, and then sodium nitrite (37mmol) was dissolved in 55ml water and added to the bottle, and then stirred at room temperature for 30 minutes, and then washed with deionized water, and the solvent was removed by vacuum centrifugation to obtain an off-white solid powder.

[0135] It is understandable that the organic compound provided in the present application is not limited to being prepared by the preparation method of the organic compound provided in the present application.

[0136] Based on the above organic compound embodiment, the present application also proposes an electron transport material, which includes the above organic compound. In one embodiment, in addition to the organic compound, the electron transport material may also include other conductive materials or semiconductor materials, such as inorganic nanomaterials such as zinc oxide and titanium dioxide, such as other organic conductive materials. In another embodiment, the electron transport material consists of the organic compound.

[0137] The electron transport material has good electron injection ability and charge transport performance, and can effectively adjust its own LUMO energy level; it not only has good energy level matching with commonly used luminescent materials, but also when used with commonly used organic hole transport materials, the electron injection level and the hole injection level are relatively matched, which is beneficial to the carrier balance of the device; in addition, the electron transport material also has ultraviolet absorption performance, can absorb ultraviolet rays, avoid ultraviolet light damage, and has better photostability.

[0138] Furthermore, the present application also proposes an optoelectronic device 100, which includes but is not limited to an organic light emitting diode, a quantum dot light emitting diode, a photovoltaic cell and a photodetector. Figure 1 The optoelectronic device 100 includes an anode 10, an electronic functional layer 30 and a cathode 20. The material of the electronic functional layer 30 includes the organic compound described above, or includes an organic compound prepared by the preparation method of the organic compound described above, or includes the electron transport material described above.

[0139] The electronic functional layer 30 of the optoelectronic device 100 includes an organic compound, which is a bissulfone benzopyrrole organic compound. Since it has multiple electron-rich nitrogen atoms and sulfur atoms, it has good electron injection ability. The introduction of the sulfone group can, on the one hand, effectively passivate the lone pair electrons of the sulfur atom, reduce the influence of light and heat on the free electrons, and improve the stability of the material; on the other hand, it can reduce the LUMO energy level of the material, reduce the band gap difference between the electrode and the electron transport layer, and make the electron injection more effective. At the same time, the band gap difference between the quantum dot and the electron transport layer is increased, which increases the injection difficulty, thereby reducing the efficiency and stability of the quantum dot due to excessive electron injection. Imbalance caused by carriers. In addition, its large conjugated linear structure itself is conducive to electron transmission.

[0140] Furthermore, when the organic compound is used as an electronic functional material in the optoelectronic device 100, the organic compound has good matching with commonly used hole transport materials (such as TFB, PVK, etc.). When used together, the balance between hole injection and electron injection in the device is good, which is beneficial to improving the carrier balance of the device, thereby improving the luminous efficiency of the optoelectronic device 100; in addition, the organic compound of the present application has a stable molecular structure and good stability, which helps to improve the life of the optoelectronic device.

[0141] In addition, the organic compound of the present application has good ultraviolet absorption performance and can absorb ultraviolet rays generated during the device preparation process. In this way, when preparing the device, the damage to the material caused by ultraviolet rays involved in the device preparation process is reduced, and the photostability of the device is improved.

[0142] In one embodiment, the material of the electronic functional layer 30 is composed of the organic compound. In other embodiments, the material of the electronic functional layer 30 may include inorganic n-type semiconductor materials or other organic n-type semiconductor materials, such as zinc oxide, in addition to the organic compound.

[0143] In one embodiment, the material of the electronic functional layer 30 may include the organic compound and the inorganic n-type semiconductor material. Further, the material of the electronic functional layer 30 may be a mixture of the organic compound and the inorganic n-type semiconductor material, or the electronic functional layer 30 is a stacked structure, including a film layer formed by the organic compound and a film layer formed by the inorganic n-type semiconductor material.

[0144] In one embodiment, the thickness of the electronic functional layer 30 may be, for example, 20-45 nm, 25-45 nm, 25-40 nm, 30-40 nm, or 30-35 nm.

[0145] Furthermore, in one embodiment, the optoelectronic device 100 may further include a light-emitting layer 40 , and the light-emitting layer 40 is disposed between the anode 10 and the electronic functional layer 30 .

[0146] In this embodiment, the optoelectronic device 100 is a light-emitting device, and the material of the electronic functional layer 30 includes a bissulfone benzopyrrole organic compound, which can help balance the injection of holes and electrons and improve the light-emitting efficiency of the optoelectronic device.

[0147] In one embodiment, the material of the light-emitting layer 40 is selected from organic light-emitting materials or quantum dot light-emitting materials.

[0148] The organic light-emitting material can be selected from at least one of diaromatic anthracene derivatives, distilbene aromatic derivatives, pyrene derivatives or fluorene derivatives, TBPe fluorescent materials emitting blue light, TTPA fluorescent materials emitting green light, TBRb fluorescent materials emitting orange light, and DBP fluorescent materials emitting red light.

[0149] The quantum dot luminescent material can be selected from at least one of a single structure quantum dot, a core-shell structure quantum dot and a perovskite semiconductor material. The single structure quantum dot is selected from at least one of a II-VI group compound, a IV-VI group compound, a III-V group compound and a I-III-VI group compound. The II-VI group compound is selected from CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdS At least one of dZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and HgZnSTe, and the IV-VI group compound is selected from SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, Sn At least one of PbTe, SnPbSSe, SnPbSeTe, and SnPbSTe, and the III-V compound is selected from 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 , at least one of GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs and InAlPSb, the I-III-VI group compound is selected from at least one of CuInS, CuInSe and AgInS; the core of the quantum dots with core-shell structure is selected from any one of the above-mentioned single-structure quantum dots, and the shell material of the quantum dots with core-shell structure is selected from at least one of CdS, CdTe, CdSeTe, CdZnSe, CdZnS, CdSeS, ZnSe, ZnSeS and ZnS.

[0150] As an example, the core-shell structured quantum dots may be selected from but not limited to at least one of CdZnSe / CdZnSe / ZnSe / CdZnS / ZnS, CdZnSe / CdZnSe / CdZnS / ZnS CdSe / CdSeS / CdS, InP / ZnSeS / ZnS, CdZnSe / ZnSe / ZnS, CdSeS / ZnSeS / ZnS, CdSe / ZnS, CdSe / ZnSe / ZnS, ZnSe / ZnS, ZnSeTe / ZnS, CdSe / CdZnSeS / ZnS and InP / ZnSe / ZnS.

[0151] It should be noted that, for the material of the aforementioned single structure quantum dot, or the material of the core of the core-shell structure quantum dot, or the material of the shell of the core-shell structure quantum dot, the chemical formula provided only indicates the elemental composition, but does not indicate the content of each element. For example, CdZnSe only indicates that it is composed of three elements, Cd, Zn and Se. If the content of each element is indicated, it corresponds to Cd x Zn 1-x Se,0 <x<1。

[0152] The perovskite semiconductor material is selected from doped or undoped inorganic perovskite semiconductors, or organic-inorganic hybrid perovskite semiconductors; the inorganic perovskite semiconductor has a general structural formula of AMX3, wherein A is Cs + ion, M is a divalent metal cation selected from Pb 2+ Sn 2+ , Cu 2+ 、Ni 2+ 、Cd 2+ Cr 2+ , Mn 2+ 、Co 2+ , Fe 2+ ,Ge 2+ , Yb 2+ 、Eu 2+ At least one of, X is a halogen anion selected from Cl - Br - ,I - At least one of the following; the general structural formula of the organic-inorganic hybrid perovskite semiconductor is BMX3, wherein B is an organic amine cation selected from CH3(CH2) n-2 NH3 + or [NH3(CH2) n NH3] 2+ , where n≥2, M is a divalent metal cation selected from Pb 2+ Sn 2+ , Cu 2+ 、Ni 2+ 、Cd2+ Cr 2+ , Mn 2+ 、Co 2+ , Fe 2+ ,Ge 2+ , Yb 2+ 、Eu 2+ At least one of, X is a halogen anion selected from Cl - Br - ,I - When n=2, the inorganic metal halide octahedron MX6 4- The metal cation M is located at the center of the halogen octahedron, and the organic amine cation B fills the gap between the octahedrons to form an infinitely extended three-dimensional structure. When n>2, the inorganic metal halide octahedron MX6 connected by the top-sharing method 4- It extends in two dimensions to form a layered structure, with an organic amine cation bilayer (protonated monoamine) or an organic amine cation monolayer (protonated diamine) inserted between the layers, and the organic layer and the inorganic layer overlap to form a stable two-dimensional layered structure.

[0153] In one embodiment, the quantum dot luminescent material includes one or more of red quantum dots, green quantum dots, and blue quantum dots.

[0154] In one embodiment, the optoelectronic device 100 further includes a hole functional layer 50, and the hole functional layer 50 is disposed between the anode 10 and the light-emitting layer 40. The hole functional layer 50 may include a hole injection layer 51 and / or a hole transport layer 52. When the hole functional layer 50 includes two layers, the hole injection layer 51 and the hole transport layer 52, the hole injection layer 51 is disposed close to the anode 10, and the hole transport layer 52 is disposed close to the light-emitting layer 40.

[0155] The material of the hole transport layer 52 is selected from arylamine, polyaniline, polypyrrole, poly(p-phenylene vinylene) and its derivatives, 4,4'-bis(p-carbazolyl)-1,1'-biphenyl compound, N,N,N',N'-tetraarylbenzidine, PEDOT:PSS and its derivatives, poly(N-vinylcarbazole) (PVK) and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, poly(spirofluorene) and its derivatives, doped or undoped NiO, MoO3, WO3, V2O5, CrO3, CuO, MoS2, MoSe2, WS3, WS e3, CuS, CuSCN; wherein the aromatic amine is selected from 4,4'-di(9-carbazole)biphenyl (CBP), poly(9,9-dioctylfluorene-CO-N-(4-butylphenyl)diphenylamine) (TFB), poly(N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine) (poly-TPD), N,N'-di(4-(N,N'-diphenyl-amino)phenyl)-N,N'-diphenylbenzidine (DNTPD), poly(9,9-dioctylfluorene-co-bis-N,N-phenyl-1,4-phenylenediamine) (PFB), 4,4' ,4"-tri(carbazol-9-yl)triphenylamine (TCATA), 4,4',4"-tri(N-carbazol-9-yl)triphenylamine (TCTA), 4,4',4"-tri(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4"-diamine (α-NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (TPD), ,4'-diamine (NPB), Spiro-NPB, Spiro-TPD, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-spiro(spiro-TPD), spiro-NPB or one or more thereof; the poly(p-)phenylene vinylene and its derivatives are selected from one or more of poly(phenylene vinylene) (PPV), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene] (MEH-PPV) and poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylene vinylene] (MOMO-PPV).

[0156] The material of the hole injection layer 51 is a material having hole injection capability, selected from poly(ethylenedioxythiophene):polystyrene sulfonate (PEDOT:PSS), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinone-dimethane (F4-TCNQ), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HATCN), copper phthalocyanine (CuPc ), poly(9,9-dioctyl-fluorene-co-N-(4-butylphenyl)-diphenylamine) (TFB), polyarylamine, poly(N-vinylcarbazole), polyaniline, polypyrrole, N,N,N',N'-tetrakis(4-methoxyphenyl)-benzidine (TPD), 4-bis[N-(1-naphthyl)-N-phenyl-amino]biphenyl (α-NPD), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 4,4',4"-tri(N-carbazolyl)-triphenylamine (TCTA), 1,1-bis[(di-4-tolylamino)phenylcyclohexane (TAPC), 4,4',4"-tri(diphenylamino)triphenylamine (TDATA) doped with F4-TCNQ, p-doped phthalocyanine (e.g., F4-TCNQ-doped zinc phthalocyanine (ZnPc)), F4-TCNQ-doped N,N'-diphenyl-N,N'-di(1-naphthyl)-1,1'-biphenyl-4,4"-diamine (α-NPD), transition metal oxides, transition metal sulfur compounds; wherein the transition metal oxides include one or more of NiO, MoO2, WO3, CuO; the metal sulfur compounds include one or more of MoS2, MoSe2, WS3, WSe3, CuS.

[0157] In one embodiment, the anode 10 and the cathode 20 are independently selected from metal electrodes, carbon electrodes, doped or undoped metal oxide electrodes and composite electrodes; wherein the material of the metal electrode is selected from at least one of Al, Ag, Cu, Mo, Au, Ba, Ca, Ni, Ir and Mg; the material of the carbon electrode is selected from at least one of graphite, carbon nanotubes, graphene and carbon fiber; the material of the doped or undoped metal oxide electrode is selected from ITO, FTO, ATO, AZO, GZO, IZO, MZO, IT At least one of ZO, ICO, AMO, SnO2, In2O3, Cd:ZnO, F:SnO2, In:SnO2, and Ga:SnO2; the material of the composite electrode is selected from at least one of 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, and ZnS / Al / ZnS. Wherein, " / " represents a stacked structure, for example, the composite electrode AZO / Ag / AZO represents an electrode of a composite structure of three stacked layers consisting of an AZO layer, an Ag layer, and an AZO layer.

[0158] It is understandable that, in addition to the above-mentioned functional layers, the optoelectronic device 100 may also be provided with some functional layers conventionally used in optoelectronic devices to help improve the performance of the optoelectronic device, such as an electron blocking layer, an electron injection layer, a hole blocking layer and / or an interface modification layer.

[0159] It can be understood that the material and thickness of each layer of the optoelectronic device 100 can be set and adjusted accordingly according to the light emitting requirements of the optoelectronic device 100 .

[0160] In some embodiments, the optoelectronic device 100 further includes a substrate (not shown), which may also be referred to as a substrate, and the above-mentioned film layer structure is arranged on one side of the substrate. The substrate may be a rigid substrate or a flexible substrate. The rigid substrate may be a ceramic material or various glass materials, etc. The flexible substrate may be a substrate formed of materials such as polyimide film (PI) and its derivatives, polyethylene naphthalate (PEN), phosphoenolpyruvic acid (PEP) or diphenylene ether resin. In one embodiment, the material of the substrate includes a combination of one or more of glass, silicon wafer, polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate, polyamide, and polyether sulfone.

[0161] It can be understood that the photoelectric device 100 can be an upright photoelectric device or an inverted photoelectric device. When the photoelectric device 100 is an upright photoelectric device, the substrate is combined with the side of the anode 10 away from the light-emitting layer 40. When the photoelectric device 100 is an inverted photoelectric device, the substrate is combined with the side of the cathode 20 away from the light-emitting layer 40.

[0162] It can be understood that the preparation methods of the various film layers in the optoelectronic device 100 provided in the present application, including the anode 10, the cathode 20, the light-emitting layer 40, the hole functional layer 50, the electronic functional layer 30 and other film layers, can be implemented by conventional techniques in the art, such as chemical methods or physical methods. Among them, the chemical method includes chemical vapor deposition, continuous ion layer adsorption and reaction, anodization, electrolytic deposition, and coprecipitation. The physical method includes physical plating and solution method, wherein the physical plating method includes: thermal evaporation coating, electron beam evaporation coating, magnetron sputtering, multi-arc ion plating, physical vapor deposition, atomic layer deposition, pulsed laser deposition, etc.; the solution method can be spin coating, printing, inkjet printing, blade coating, printing, dip pulling, immersion, spraying, rolling, casting, slit coating, and strip coating.

[0163] It is understandable that the optoelectronic device 100 may further include an encapsulation layer (not shown) to isolate water and oxygen (for example, to make the concentration of oxygen and water less than 0.1ppm) and improve the performance stability of the optoelectronic device 100. Specifically, the encapsulation material used to form the encapsulation layer may be selected from at least one of UV glue, metal film, and glass glue. In a specific embodiment, the encapsulation material may be acrylic resin or epoxy resin.

[0164] The present application also relates to a display device, which includes the optoelectronic device provided in the present application. The display device can be any electronic product with a display function, including but not limited to smart phones, tablet computers, laptop computers, digital cameras, digital video cameras, smart wearable devices, smart weighing electronic scales, car displays, televisions or e-book readers, wherein the smart wearable device can be, for example, a smart bracelet, a smart watch, a virtual reality (VR) helmet, etc.

[0165] The present application is described in detail below by means of specific examples, which are only partial examples of the present application and are not intended to limit the present application. The raw materials used in the following examples are all commercially available products unless otherwise specified.

[0166] The structural formulas of compounds M1 to M10 mentioned in the following examples are as follows:

[0167]

[0168]

[0169] Example 1: The synthesis route of the organic compound M1 in this example is as follows:

[0170]

[0171] Step 1: Add 34 mmol 1-bromo-2,4,5-trinitroamine (CAS: 89464-07-3) and 60 ml acetic acid into a two-necked bottle, then dissolve sodium nitrite (37 mmol) in 55 ml water, add it into the bottle, and then stir at room temperature for 30 minutes, then wash with deionized water, and remove the solvent by vacuum centrifugation to obtain an off-white solid powder compound M1-6. Compound M1-1 (CAS: 427875-87-4) (4 mmol, 1052 mg) was added to a 100 mL two-necked bottle. Compound M1-6 (8 mmol, 1936 mg) and tetrakistriphenylphosphine palladium (0.4 mmol, 462 mg) were added and dissolved in 30 mL of toluene solvent. The mixture was heated to 110° C. and reacted for 10 h. The reaction was stopped when the raw material was completely reacted by monitoring by thin layer chromatography (TLC). The reaction solution was distilled under reduced pressure to remove the solvent. The crude product was mixed with 200 to 300 mesh silica gel and separated by column chromatography. The mobile phase was petroleum ether:ethyl acetate (volume ratio of 15:1). Compound M1-2 was finally obtained as a yellow solid product (1409 mg) with a yield of 60%.

[0172] Step 2: Compound M1-2 (1 mmol, 587 mg), PPh3 (10 mmol, 2.62 g) (CAS: 603-35-0) were added to a 100 mL two-necked bottle, and 20 ml of ultra-dry o-dichlorobenzene (ODB) was added. Nitrogen was introduced and vacuum pumped for 30 minutes. Stir and heat to reflux. The reaction was continued for 24 hours. The reaction was stopped, and o-dichlorobenzene was removed by vacuum distillation. The crude product was separated by column chromatography. The eluent used was petroleum ether, dichloromethane and ethyl acetate (volume ratio of 12:1:1). Finally, compound M1-3 was obtained as a solid product of 157 mg with a yield of 30%.

[0173] Step 3: Compound M1-3 (1 mmol, 523 mg) was added to a 100 ml two-necked bottle, and 1-bromohexane (2 mmol, 330 mg) (compound M1-7, CAS: 111-25-1), potassium hydroxide (2 mmol, 126 mg) were weighed and added, 40 ml of dimethyl sulfoxide was added, nitrogen was introduced and vacuumed for 15 minutes using a vacuum pump, stirred and heated to 85 ° C, the reaction was continued for 24 hours, the reaction was stopped and cooled to room temperature, the reaction solution was extracted, and 200 ml of water and 1500 ml of dichloromethane were used for repeated extraction 3 to 4 times. The obtained organic extract was dried using anhydrous magnesium sulfate, and the filtrate was collected and mixed with 200 to 300 mesh silica gel for purification and separation using column chromatography. The eluent used petroleum ether, dichloromethane and ethyl acetate (volume ratio of 200:1:1) to finally obtain compound M1-4 as a light yellow solid 672 mg with a yield of 90%.

[0174] Step 4: Add compound M1-4 (1mmol, 747mg) to a 50ml single-mouth bottle, and add 5ml of glacial acetic acid and 10ml of CHCl3 solvent; then add 2.5ml of 30% H2O2 aqueous solution in an ice bath; heat to 60°C and react for 24h; after the reaction, pour the reaction solution into a separatory funnel and extract with dichloromethane and water 3 to 4 times, collect the organic phase, dry it with anhydrous magnesium sulfate and filter and collect the filtrate, and separate the filtrate by silica gel column chromatography, and use petroleum ether and ethyl acetate (volume ratio of 40:1) as the eluent; finally, 649mg of solid product, namely intermediate M1-5, is obtained with a yield of 80%.

[0175] Step 5: Add compound M1-5 (1 mmol, 811 mg), 4-iodotriphenylamine (3 mmol, 1113 mg) (compound M1-8, CAS: 38257-52-2), Pd2(dba)3 (0.05 mmol, 50 mg) and sodium tert-butoxide (5 mmol, 480 mg) and tert-butylphosphine (5 mmol, 450 mg) (CAS No.: 2501-94-2) to a 100 mL two-necked bottle, then add 40 mL of redistilled toluene, introduce nitrogen, and The reaction was evacuated with a vacuum pump and replaced with nitrogen for 15 minutes. The reaction flask was protected from light by tin foil, stirred and heated to 110°C for 24 hours. The reaction was stopped and cooled to room temperature. The reaction solution was extracted and repeatedly washed with dichloromethane (1000 mL) and water (250 mL) for 3 to 4 times. The organic phase was dried with anhydrous magnesium sulfate and crudely separated by column chromatography. The developing agent was petroleum ether: dichloromethane: acetone (volume ratio of 20:2:1). The organic compound M1 was obtained as a yellow solid of 702 mg with a yield of 70%.

[0176] The NMR data are as follows: 1H NMR(500MHz,Chloroform-d)δ8.60(s,2H),8.06(s,2H),7.75-7.72(m,4H),7.27-7.23(m,8H),7.17-7.14(m,4H),7.11-7.07(m,8H),7.05 -7.01(m,4H),4.50(t,J=6.3Hz,2H),4.46(t,J=6.2Hz,4H),1.82-1.73(m,6H),1.48-1.41(m,6H),1.34-1.25(m,12H),0.92-0.87(m,9H).

[0177] Example 2: Preparation of organic compound M2:

[0178]

[0179] The synthesis of organic compound M2 in this example is similar to that of M1, except that 1-bromo-n-hexane (compound M1-7) in step 3 is replaced by 1-bromo-n-octane (compound M2-7, CAS: 111-83-1) in Example 1, and 4-iodotriphenylamine (compound M1-8) in step 5 is replaced by 3-bromo-10-methyl-10H-phenothiazine (compound M2-8, CAS: 52853-38-0), and the reaction conditions and the amount of substance are not changed, and a yellow solid product M2 is finally obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.63(s,2H),8.11(s,2H),7.91-7.89(m,2H),7.70-7.69(m,2H),7.29-7.27(m,2H),7.24-7.18(m,4H),7.12-7.10 (m,2H),7.02-6.98(m,2H),4.50(t,J=6.2Hz,2H),4.47(t,J=6.3Hz,4H) ,3.44(s,6H),1.79-1.73(m,6H),1.49-1.25(m,26H),0.91-0.87(m,9H).

[0180] Example 3: Preparation of organic compound M3:

[0181]

[0182] The synthesis of organic compound M3 in this example is similar to that of M1, except that compound M1-1 is replaced with 4-(4-hexyloxybenzene)-4H-dithienopyrrole (compound M3-1, CAS: 1572185-73-9) in Example 1, 1-bromo-n-hexane is replaced with 1-bromo-n-octane (compound 2-7) in step 3, and 4-iodotriphenylamine is replaced with 3-bromo-9-methyl-9H-carbazole (compound 3-8, CAS: 91828-08-9) in step 5, and the reaction conditions and the amount of substance are not changed, and a yellow solid product M3 is finally obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.91-8.89(m,1H),8.63(s,2H),8.36-8.34(m,1H),8.09(s,2 H),7.96-7.92(m,2H),7.80-7.77(m,2H),7.75-7.72(m,2H),7.61-7.59(m,2H),7.43-7.36 (m,4H),7.30-7.27(m,2H),7.16-7.13(m,2H),4.43(t,J=6.2Hz,4H),4.01(t,J=6.1Hz,2H) ,3.80(s,6H),1.82-1.73(m,6H),1.47-1.41(m,2H),1.35-1.25(m,24H),0.92-0.87(m,9H).

[0183] Example 4: Preparation of organic compound M4:

[0184]

[0185] The synthesis of organic compound M4 in this example is similar to that of M3, except that compound 3-8 in step 5 of Example 3 is replaced by 2-bromothianthrene (compound 4-8, CAS: 53455-06-4) and 2-bromo-dibenzodioxabenzene (compound 4-9, CAS: 105906-36-3) (the amount of each compound is halved accordingly), and the other reaction conditions and the amount of the substance are not changed, and finally a yellow solid product M4 is obtained. The NMR data are as follows: 1H NMR(500MHz,Chloroform-d)δ8.76(s,1H),8.59(s,1H),8.10(d,J=19.8Hz,2H),7.83-7.81(m,1H), 7.76-7.72(m,1H),7.71-7.69(m,1H),7.62-7.59(m,1H),7.58-7.55(m,1H),7.39-7.33(m,4H),7.2 6-7.22(m,2H),7.15-7.11(m,3H),7.06-6.98(m,4H),4.46(t,J=6.3Hz,2H),4.41(t,J=6.3Hz,2H), 4.01(t,J=6.1Hz,2H),1.82-1.73(m,6H),1.47-1.41(m,2H),1.35-1.25(m,22H),0.93-0.87(m,9H).

[0186] Example 5: Preparation of organic compound M5:

[0187]

[0188] The synthesis of organic compound M5 in this example is similar to that of M3, except that compound 2-7 in step 3 is replaced with 1-butoxy-4-iodobenzene (compound 5-7, CAS: 20651-67-6) in Example 3, and compound 3-8 in step 5 is replaced with 9-(4-iodobenzene)-9H-carbazole (compound 5-8, CAS: 57103-15-8) and 10-(4-iodobenzene)-10H-phenothiazine (compound 5-9, CAS: 262861-84-7) respectively (the amount of each compound is halved accordingly), and the other reaction conditions and the amount of the substance are not changed, and a yellow solid product M5 is finally obtained. The NMR data are as follows: 1H NMR(500MHz,Chloroform-d)δ8.28-8.25(m,2H),8.16-8.13(m,2H),7.95-7.93(m,2H),7.90-7.87(m,2 H),7.87-7.84(m,4H),7.78-7.74(m,2H),7.64-7.60(m,4H),7.57-7.53(m,2H),7.35-7.30(m,2H),7.3 0-7.27(m,2H),7.26-7.22(m,4H),7.21-7.19(m,2H),7.19-7.16(m,2H),7.11-7.03(m,8H),4.02-3.97 (m,6H),1.80-1.73(m,6H),1.53-1.41(m,6H),1.34-1.28(m,4H),0.99-0.95(m,6H),0.93-0.89(m,3H).

[0189] Example 6: Preparation of organic compound M6:

[0190]

[0191] The synthesis of organic compound M6 in this example is similar to that of M1, except that compound M1-1 is replaced by M6-1 in Example 1, M1-7 is replaced by M6-7 in step 3, and M1-8 is replaced by 4-iodo-N,N-di(4-methoxyphenyl)aniline (M6-8, CAS: 201808-15-5) and 10-(4-iodophenyl)-9,9-methyl-9,10-dihydroacridine (M6-9, CAS: 1323330-73-9) in step 5, respectively (the amount of each compound is halved accordingly), and the other reaction conditions and the amount of the substance are not changed, and finally a yellow solid product M6 is obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.26-8.24(m,2H),7.94-7.92(m,2H),7.86-7.83(m,4H),7.64-7.58(m,4H),7.19-7.00(m,20H),6.86-6.83(m,4H),4 .25(t,J=6.3Hz,2H),4.00(t,J=6.1Hz,4H),3.78(s,6H),1.83-1.74(m,6 H),1.56(s,6H),1.37-1.26(m,8H),1.10-1.06(m,6H),0.91-0.87(m,3H).

[0192] Example 7: Preparation of organic compound M7:

[0193]

[0194] The synthesis of the organic compound M7 in this example is similar to that of M1, except that the compound M1-1 is replaced with 4-n-pentadecane-4H-dithienopyrrole (M7-1, CAS: 141029-77-8) in Example 1, 1-bromohexane in step 3 is replaced with 1-bromododecane (M7-7, CAS: 143-15-7), and 4-iodotriphenylamine in step 5 is replaced with 4,4'-dimethoxydiphenylamine (M7-8, CAS: 101-70-2), and the other reaction conditions and the amount of substances are not changed, and finally a yellow solid product M7 is obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ7.98-7.96(m,2H),7.94-7.92(m,2H),7.06-7.02(m,8H),6.84-6.79( m,8H),4.26-4.21(m,6H),3.79(s,12H),1.83-1.76(m,6H),1.31-1.22(m,60H),0.91-0.86(m,9H).

[0195] Example 8: Preparation of organic compound M8:

[0196]

[0197] The synthesis of organic compound M8 in this example is similar to that of M7, except that in Example 7, M7-7 in step 3 is replaced by 4-bromododecyloxybenzene (M8-7, CAS: 123883-51-2), and M7-8 in step 5 is replaced by 4-bromo-4',4"-dimethoxytriphenylamine (M8-8, CAS: 194416-45-0), respectively. The other reaction conditions and the amount of substances are not changed, and a yellow solid product M8 is finally obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.34-8.31(m,2H),7.86-7.81(m,4H),7.47-7 .45(m,4H),7.41-7.38(m,2H),7.17-7.13(m,4H),7.09-7.06(m,12H),6.86 -6.82(m,8H),4.25(t,J=6.3Hz,2H),4.02(t,J=6.1Hz,4H),3.78(s,12H),1 .83-1.73(m,6H),1.44-1.38(m,4H),1.30-1.22(m,52H),0.91-0.86(m,9H).

[0198] Example 9: Preparation of organic compound M9:

[0199]

[0200] The synthesis of the organic compound M9 in this example is similar to that of M1, except that the compound M1-1 is replaced with 4-n-octyloxybenzene-4H-dithienopyrrole (M9-1, CAS: 2601398-74-5) in Example 1, 1-bromo-n-hexane is replaced with 1-bromo-n-pentadecane (M9-7, CAS: 629-72-1) in step 3, and 4-iodotriphenylamine is replaced with 2-bromo-thiophene (M9-8, CAS: 10230-35-0) in step 5, and the other reaction conditions and the amount of substances are not changed, and a yellow solid product M9 is finally obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.24-8.22(m,2H),7.90-7.86(m,2H),7.63-7.59(m,2H),7.17(dd,J=6.8,1.9Hz,4H),7.11-7.01(m,8H),6.9 0-6.84(m,4H),4.23(t,J=6.3Hz,4H),4.02(t,J=6.1Hz,2H),1.82-1.74(m,6H),1.45-1.39(m,2H),1.32-1.23(m,54H),0.91-0.87(m,9H).

[0201] Example 10: Preparation of organic compound M10:

[0202]

[0203] The synthesis of the organic compound M10 in this example is similar to that of M1, except that the compound M1-1 is replaced with 4-n-octylbenzene-4H-dithienopyrrole (M10-1, CAS: 141029-75-6) in Example 1, the 1-bromohexane M1-7 in step 3 is replaced with 4-bromohexane (M10-7, CAS: 30752-20-6), and the 4-iodotriphenylamine M1-8 in step 5 is replaced with 10-(4-bromobenzene)-phenoxazine (M10-8, CAS: 71041-21-9). The other reaction conditions and the amount of substances are not changed, and a yellow solid product M10 is finally obtained. 1H NMR(500MHz,Chloroform-d)δ8.26-8.24(m,2H),7.94-7.92(m,2H),7.86-7.83(m,4H),7.64-7.60(m,4H),7.19-7.15(m,4H),7.12-6.97(m,16H ),6.74-6.72(m,4H),4.25(t,J=6.3Hz,2H),4.02(t,J=6.1Hz,4H),1.82 -1.73(m,6H),1.45-1.39(m,4H),1.30-1.23(m,34H),0.91-0.87(m,9H).

[0204] Comparative Example 1: Preparation of organic compound P1:

[0205]

[0206] The synthesis of organic compound P1 in this example is similar to that of M1, except that M1-6 is replaced with 5-bromo-6-nitro-benzene (CAS: 1020720-09-5) in step 1, and the other reaction conditions and the amount of substances are unchanged, and finally a yellow solid product P1 is obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.20-8.18(m,2H),7.87-7.84(m,2H),7.80-7.79(m,2H),7.58-7.56(m,4H),7.28-7.23(m,12H),7.11-7.08(m ,8H),7.06-7.02(m,4H),4.41-4.38(m,4H),4.17-4.14(m,2H),1.79-1 .73(m,6H),1.45-1.39(m,6H),1.34-1.27(m,12H),0.92-0.88(m,9H).

[0207] Comparative Example 2: Preparation of organic compound P2:

[0208]

[0209] The synthesis of organic compound P2 in this example is similar to that of M2, except that M1-6 is replaced with 5-bromo-6-nitro-benzene in step 1, and the other reaction conditions and the amount of substances remain unchanged, and finally a yellow solid product P2 is obtained. The NMR data are as follows: 1HNMR(500MHz,Chloroform-d)δ8.21-8.18(m,2H),7.90-7.87(m,2H),7.80-7.78(m,2H),7.49-7.46(m,4H),7.35-7.32(m,2H),7.25-7.19(m,4H),7. 13-7.10(m,2H),7.03-6.98(m,2H),4.40(t,J=6.2Hz,4H),4.17-4.14(m,2 H),3.44(s,6H),1.80-1.73(m,6H),1.46-1.25(m,26H),0.91-0.87(m,9H).

[0210] Comparative Example 3: Preparation of organic compound P3:

[0211]

[0212] The synthesis of the organic compound P3 in this example is similar to that of the compound M1-3 in Example 1, except that M1-6 is replaced with 5-bromo-6-nitro-benzene in step 1, and the other reaction conditions and the amount of substances are unchanged, and finally a yellow solid product P3 is obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ7.99-7.96(m,2H),7.60-7.58(m,2H),7.42-7.38(m,2H),7.32-7.28(m,2H),4.47(t, J=6.3Hz,2H),4.37(t,J=6.3Hz,4H),1.83-1.75(m,6H),1.46-1.38(m,6H),1.35-1.27(m,12H),0.91-0.88(m,9H).

[0213] Comparative Example 4: Preparation of organic compound P4:

[0214]

[0215] The synthesis of the organic compound P4 in this example is similar to that of the compound M1-3 in Example 1, except that M1-6 is replaced with 5-bromo-6-nitro-benzopyrrole (104447-74-7) in step 1, and the other reaction conditions and the amount of substances are unchanged, and finally a yellow solid product P4 is obtained. The NMR data are as follows: 1H NMR(500MHz,Chloroform-d)δ9.65-9.62(m,2H),8.70-8.66(m,2H),7.81-7.77(m,2H),7.30-7.26(m,2H),6.62-6.58(m,2H) ,4.49(t,J=6.2Hz,2H),4.43(t,J=6.3Hz,4H),1.83-1.75(m,6H),1.47-1.40(m,6H),1.34-1.26(m,12H),0.92-0.87(m,9H).

[0216] Device Example 1

[0217] The device embodiment provides a quantum dot light emitting diode and a method for preparing the same, which specifically includes the following steps.

[0218] Step 1: Place the ITO glass sheet in a glass dish filled with ethanol solution, and ultrasonicate with acetone, deionized water, and ethanol for 20 minutes respectively, and then blow dry with a nitrogen gun; then place the cleaned ITO glass sheet in oxygen plasma for further cleaning for 10 minutes; continue to use UV-ozone to treat the surface of the ITO substrate for 15 minutes;

[0219] Step 2: Spin-coat the cleaned ITO glass sheet with PEDOT:PSS in air at a speed of 5000 r / min for 30 seconds; after spin coating, place it in air for annealing at a temperature of 150°C for 30 minutes to obtain a hole injection layer with a thickness of 40 nm;

[0220] Step 3: Spin-coat TFB (8 mg / mL) on the hole injection layer at a rotation speed of 3000 r / min for 30 seconds; after spin coating, anneal in a glove box at a temperature of 120° C. for 10 minutes to obtain a hole transport layer;

[0221] Step 4: Spin-coat quantum dots QD (20 mg / mL) on the hole transport layer at a speed of 2000 r / min for 30 seconds; then -2 MPa environment for 15 min to obtain a luminescent layer with a thickness of 30 nm;

[0222] Step 5: Spin the organic compound M1 (30 mg / mL) in Material Example 1 onto the light-emitting layer at a speed of 3000 r / min for 30 seconds, and then -2 MPa environment for 15 min to obtain a 30-50 nm electron transport layer;

[0223] Step 6: Through thermal evaporation, the vacuum degree is not higher than 3*10-4 Pa, evaporate Ag at a rate of 1 angstrom / s for 200 seconds to form a top silver electrode with a thickness of 20 nm on the electron transport layer, and then perform epoxy resin encapsulation.

[0224] The device structure is: ITO / PEDOT:PPS (40nm) / TFB (8wt%) / QD (30nm) / M1 (1nm) / Ag (20nm).

[0225] Device Examples 2-10

[0226] Device Example n is basically the same as Device Example 1, with the only difference being that in Device Example n: when preparing the electron transport layer in step 5, the organic compound M1 is replaced with the organic compound of Material Example n, n is an integer from 2 to 10, and the organic compound of Material Example n is M2 to M10.

[0227] Device Comparative Examples 1 to 4

[0228] The device comparison example m of the present invention is basically the same as the device embodiment 1, and the only difference is that in the device comparison example m: when preparing the electron transport layer in step 5, the organic compound M1 is replaced by the organic compound of the material comparison example 1, m is an integer from 1 to 4, and the organic compound of the material comparison example m is P1 to P4.

[0229] Device Comparison Example 5

[0230] This device embodiment is basically the same as device embodiment 1, and the only difference is that when preparing the electron transport layer in step 5, the organic compound M1 is replaced by PCBM (fullerene derivative C70, CAS: 609771-63-3).

[0231] Experimental example

[0232] The maximum brightness L of the quantum dot light-emitting diodes of device examples 1-10 and device comparison examples 1-5 was measured. max Test, life T95 test, life T95@1000nit test, current efficiency CE test, light stability test, electron mobility test. The test results are shown in Table 1.

[0233] Among them, the maximum brightness L max The test method of current efficiency CE is as follows: using FPD optical property measurement equipment from Foster, controlling the efficiency test system built by QE PRO spectrometer, Keithley 2400, and Keithley 6485 through LabView, measuring parameters such as voltage, current, brightness, and luminous spectrum, and calculating the current efficiency CE;

[0234] The test method for the life span T95@1000nit is: the time required for the device to reduce its brightness to a certain proportion of the maximum brightness under constant current or voltage driving. The time when the brightness drops to 95% of the maximum brightness is defined as T95, and this life span is the measured life span. In order to shorten the test cycle, the device life span test is usually carried out at high brightness by accelerating device aging, and the life span at high brightness is obtained by fitting the extended exponential decay brightness attenuation fitting formula. For example, the life span at 1000nit is calculated as T95@1000nit. The specific calculation formula is as follows:

[0235]

[0236] Among them, T95 L For lifespan at low brightness, T95 H is the measured lifetime under high brightness, L H To accelerate the device to the highest brightness, L L is 1000nit, A is the acceleration factor, and this experiment measured the lifespan of several groups of green QLED devices at rated brightness and found that the A value was 1.7.

[0237] The method for photostability testing is: testing the initial current efficiency CE of the optoelectronic devices of device examples 1-10 and device comparative examples 1-4, recording their initial data, and then placing them in a closed environment under a standard ultraviolet light source (350nm) at 100mW / cm 2 The device was irradiated with a power of 100 nm for 6 h, the current efficiency CE after UV irradiation was recorded, and the decay rate was calculated.

[0238] The method for testing electron mobility is as follows: using the above device preparation process for material examples 1-10 and material comparative examples 1-4, the device structure constructed is: ITO / M (20nm) / Ag (20nm); wherein M refers to the electron transport material prepared in material examples 1-6 and material comparative examples 1-3. Then the electron mobility is tested using the space charge limited current method (SCLC).

[0239] Table 1

[0240]

[0241]

[0242] Table 2

[0243]

[0244] It can be seen from Tables 1 and 2 that the electron mobility of the organic compound provided in this application is 5×10 -5 cm 2 V -1 s -1 ~9×10 -5 cm 2 V -1 s -1 Although it is lower than the electron mobility of ZnO nanoparticles or doped ZnO nanoparticles (about 0.5×10 -3 ~1×10 -3 cm 2 / Vs range), but higher than fullerene electron transport material PCBM, and the organic compound of the present application has good compatibility with commonly used hole transport materials, and is suitable for application scenarios with low electron mobility requirements. As shown in the above device embodiments 1 to 6, each device embodiment has a high maximum brightness L max , lifespan T95, lifespan T95@1000nit, current efficiency CE, and lower CE decay rate indicate that the device has a good balance between hole injection and electron injection, so that the device has higher photoelectric performance and lifespan; in addition, the organic compound of the present application has better tolerance to ultraviolet light and is not easily damaged by ultraviolet light, so that the device has higher light stability, which is reflected in the lower CE decay rate of the device embodiment;

[0245] In addition, by comparing device example 1 with device comparison examples 1, 3 and 4, and comparing device example 2 with device comparison example 2, it can be found that the device example has a significantly lower CE decay rate, indicating that the organic compound proposed in the present application has high photostability. This may be because in the molecular structure of the compound of the present application, triazole and benzene form a fused structure, and Ar1 / Ar2 is connected to the triazole rather than directly to the benzene ring.

[0246] The organic compounds and preparation methods thereof, electron transport materials, optoelectronic devices, and display devices provided in the embodiments of the present application are introduced in detail above. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the methods and core ideas of the present application. At the same time, for technicians in this field, according to the ideas of the present application, there will be changes in the specific implementation methods and application scopes. In summary, the content of this specification should not be understood as a limitation on the present application.

Claims

1. An organic compound, characterized in that It has the structure shown in formula (I): wherein R1, R2, and R3 are independently selected from H, D, a halogen atom, a substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C7~C 36 Alkylphenyl, substituted or unsubstituted C7~C 36 One or more of alkoxyphenyl; Ar1 and Ar2 are each independently selected from the following structures: Wherein, X is CR6R7, S, NR8 or O; M is NR9, O, SiR 10 R 11 or S; R4 and R5 are each independently selected from substituted or unsubstituted C1 to C 30 Alkyl, substituted or unsubstituted C1~C 30 A combination of one or more of alkoxy; R6 to R 11 Each independently selected from H, D, substituted or unsubstituted C1-C 30 A combination of one or more of an alkyl group, a substituted or unsubstituted aryl group having 6 to 60 ring atoms; m is 0 or 1; n1 and n2 are each independently selected from integers from 0 to 5; n3 and n4 are each independently selected from integers of 0-4.

2. The organic compound according to claim 1, characterized in that The organic compound has a structure shown in formula (II):

3. The organic compound according to claim 1 or 2, characterized in that Ar1 and Ar2 are selected from one of the following substituted or unsubstituted structures:

4. The organic compound according to claim 3, characterized in that Ar1 and Ar2 are each independently selected from one of the following structural formulas (1-1) to (1-13):

5. The organic compound according to claim 3, characterized in that R4 and R5 are each independently selected from substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C1~C 10 One or more combinations of alkoxy; and / or, R6 to R 11 Each independently selected from H, D, substituted or unsubstituted C1-C 10 A combination of one or more of an alkyl group and a substituted or unsubstituted aryl group having 6 to 10 ring atoms; and / or, n1 and n2 are each independently selected from 0 or 1; and / or, n3 and n4 are each independently selected from 0 or 1.

6. The organic compound according to claim 1 or 2, characterized in that R1, R2, and R3 are each independently selected from substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1~C 12 Alkoxy, substituted or unsubstituted C7~C 18 Alkylphenyl, substituted or unsubstituted C7~C 18 One or more of alkoxyphenyl; and / or, The substituent is selected from one or more combinations of hydrogen, deuterium, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, and cyano.

7. The organic compound according to claim 1 or 2, characterized in that The organic compound includes one or more of the following structural formulas:

8. A method for preparing an organic compound, characterized in that: The following steps are involved: Compound 1 and compound a are mixed and subjected to a first reaction to obtain compound 2; The compound 2 is mixed with a reducing agent to carry out a second reaction to obtain a compound 3; The compound 3 and the compound b are mixed and subjected to a third reaction to obtain a compound 4; The compound 4 is mixed with an oxidant to carry out a fourth reaction to obtain a compound 5; The compound 5 is mixed with the compound c to carry out a fifth reaction to obtain an organic compound 6; Among them, compound 1, compound 2, compound 3, compound 4, compound 5, organic compound 6, compound a, compound b, and compound c have the following structural formulas respectively: wherein Y, at each occurrence, is independently selected from a halogen group; R represents R2 or R3, Ar represents Ar1 or Ar2; R1, R2, and R3 are each independently selected from H, D, a halogen atom, a substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C7~C 36 Alkylphenyl, substituted or unsubstituted C7~C 36 One or more of alkoxyphenyl; Ar1 and Ar2 are each independently selected from the following structures: Wherein, X is CR6R7, S, NR8 or O; M is NR9, O, SiR 10 R 11 or S; R4 and R5 are each independently selected from substituted or unsubstituted C1 to C 30 Alkyl, substituted or unsubstituted C1~C 30 A combination of one or more of alkoxy; R6 to R 11 Each independently selected from H, D, substituted or unsubstituted C1-C 30 A combination of one or more of an alkyl group, a substituted or unsubstituted aryl group having 6 to 60 ring atoms; m is 0 or 1; n1 and n2 are each independently selected from integers from 0 to 5; n3 and n4 are each independently selected from integers of 0-4.

9. The preparation method according to claim 8, characterized in that: When the organic compound has a structure represented by formula (II), the compound a includes a compound having the following structure (a-1); 10. The preparation method according to claim 8, characterized in that: The step of mixing compound 1 and compound a and performing a first reaction to obtain compound 2 comprises: mixing compound 1, compound a and a palladium catalyst under alkaline conditions under the protection of an inert gas and performing a first reaction to obtain compound 2; wherein: The molar ratio of the compound 1 to the compound a is 1:(2.2-4); and / or, The molar ratio of the compound 1 to the palladium catalyst is 1:(0.1-0.2); and / or, The reaction temperature of the first reaction is 150-170° C.; and / or, The reaction time of the first reaction is 8 to 12 hours.

11. The preparation method according to claim 8, characterized in that: The reducing agent comprises one or more of trimethyl phosphite, triethyl phosphite and tripropyl phosphite; and / or, The oxidant comprises peroxide, and the peroxide comprises one or more of hydrogen peroxide, potassium persulfate, and sodium persulfate; and / or, The molar ratio of the compound 2 to the reducing agent is 1:(40-60); and / or, The reaction temperature of the second reaction is 140-170° C.; and / or, The reaction time of the second reaction is 12 to 24 hours; and / or, The molar ratio of the compound 3 to the compound b is 1:(2-4); and / or, The reaction temperature of the third reaction is 80-110° C.; and / or, The reaction time of the third reaction is 6 to 24 hours; and / or, The molar ratio of the compound 4 to the oxidant is 1:(40-80); and / or, The reaction temperature of the fourth reaction is 40-60° C.; and / or, The reaction time of the fourth reaction is 12 to 24 hours; and / or, The molar ratio of the compound 5 to the compound c is 1:(2-4); and / or, The reaction temperature of the fifth reaction is 80-110° C.; and / or, The reaction time of the fifth reaction is 12 to 24 hours.

12. An electron transport material, characterized in that The organic compound comprises the organic compound described in any one of claims 1 to 7, or the organic compound prepared by the method for preparing the organic compound described in any one of claims 8 to 11.

13. A photoelectric device, characterized in that: It comprises an anode, an electronic functional layer and a cathode, wherein the material of the electronic functional layer comprises the organic compound described in any one of claims 1 to 7, or comprises an organic compound prepared by the method for preparing the organic compound described in any one of claims 8 to 11, or comprises the electron transport material described in claim 12.

14. The optoelectronic device according to claim 13, wherein: The anode and the cathode are independently selected from metal electrodes, carbon electrodes, doped or undoped metal oxide electrodes and composite electrodes; wherein the material of the metal electrode is selected from at least one of Al, Ag, Cu, Mo, Au, Ba, Ca, Ni, Ir and Mg; the material of the carbon electrode is selected from at least one of graphite, carbon nanotubes, graphene and carbon fiber; the material of the doped or undoped metal oxide electrode is selected from ITO, FTO, ATO, AZO, GZO, IZO, MZO, I At least one of TZO, ICO, AMO, SnO2, In2O3, Cd:ZnO, Ga:SnO2; the material of the composite electrode is selected from one of 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 and ZnS / Al / ZnS; and / or, The optoelectronic device comprises a light-emitting layer, which is arranged between the anode and the electronic functional layer, and the material of the light-emitting layer is selected from an organic light-emitting material or a quantum dot light-emitting material; the organic light-emitting material is selected from at least one of diaromatic anthracene derivatives, distilbene aromatic derivatives, pyrene derivatives or fluorene derivatives, TBPe fluorescent materials emitting blue light, TTPA fluorescent materials emitting green light, TBRb fluorescent materials emitting orange light and DBP fluorescent materials emitting red light; the quantum dot light-emitting material is selected from at least one of single-structure quantum dots, core-shell structure quantum dots and perovskite semiconductor materials, and the single-structure quantum dots are selected from II-VI compounds, IV-VI compounds, III-V compounds. The compound is selected from the group consisting 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, CdHgSe, Cd At least one of HgSTe, HgZnSeS, HgZnSeTe and HgZnSTe, the IV-VI group compound is selected from at least one of SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe and SnPbSTe, the III-V group compound is selected from at least one of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaN At least one of As, 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, and the Group I-III-VI compound is at least one of CuInS, CuInSe and AgInS;The core of the quantum dots of the core-shell structure is selected from any one of the above-mentioned single-structure quantum dots, and the shell material of the quantum dots of the core-shell structure is selected from at least one of CdS, CdTe, CdSeTe, CdZnSe, CdZnS, CdSeS, ZnSe, ZnSeS and ZnS; the perovskite semiconductor material is selected from doped or undoped inorganic perovskite semiconductors, or organic-inorganic hybrid perovskite semiconductors; the general structural formula of the inorganic perovskite semiconductor is AMX3, wherein A is Cs; + ion, M is a divalent metal cation selected from Pb 2+ Sn 2+ , Cu 2+ 、Ni 2+ 、Cd 2 + Cr 2+ , Mn 2+ 、Co 2+ , Fe 2+ ,Ge 2+ , Yb 2+ 、Eu 2+ At least one of, X is a halogen anion selected from Cl - Br - ,I - At least one of the following; the general structural formula of the organic-inorganic hybrid perovskite semiconductor is BMX3, wherein B is an organic amine cation selected from CH3(CH2) n-2 NH3 + or [NH3(CH2) n NH3] 2+ , where n≥2, M is a divalent metal cation selected from Pb 2+ Sn 2+ , Cu 2+ 、Ni 2+ 、Cd 2+ Cr 2+ , Mn 2+ 、Co 2+ , Fe 2+ ,Ge 2+ , Yb 2+ 、Eu 2+ At least one of, X is a halogen anion selected from Cl - Br - ,I - At least one of .

15. A display device, characterized in that: The optoelectronic device comprising claim 13 or 14.

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