Organic compound, preparation method thereof and electronic device

Abstract

The invention discloses an organic compound, a preparation method thereof and an electronic device. The organic compound provided by the invention is a disulfuryl benzopyrrole organic compound, and has a good electron injection capability due to a plurality of electron-rich nitrogen atoms, and the introduction of sulfuryl can effectively adjust the LUMO energy level of the organic compound; and the large conjugated linear structure is beneficial to electron transmission.

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, and an electronic 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 inorganic nanomaterials, such as zinc oxide (ZnO) and titanium dioxide (TiO2).

[0003] However, inorganic materials such as ZnO also have limitations in their application. For example, they have high electron mobility, but some specific application scenarios require the use of electron transport materials with relatively low electron mobility. In this case, inorganic materials such as ZnO cannot be used as electron transport materials.

[0004] Therefore, in addition to research on adjusting applications based on existing electron transport materials, the development of new electron transport materials is also considered one of the research and development focuses in this field.

[0005] Application Contents

[0006] In view of this, the present application provides an organic compound and a preparation method thereof, and an electronic device, aiming to provide a new type of electron transport material

[0007] The embodiment of the present application is implemented as follows: the embodiment of the present application provides an organic compound having a structure shown in formula (I):

[0008]

[0009] wherein 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 Phenylalkyl, substituted or unsubstituted C7~C 36 One or more of phenylalkoxy groups;

[0010] Ar1 and Ar2 are each independently selected from the following structures:

[0011]

[0012] Wherein, D1, D3, D4, and D5 are selected from substituted or unsubstituted aryl groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaryl groups having 5 to 60 ring atoms, or a combination thereof;

[0013] D2 is selected from H, D, a substituted or unsubstituted aryl group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, or a combination thereof;

[0014] n1 and n2 are each independently selected from integers of 0-4.

[0015] Optionally, in some embodiments of the present application, the organic compound has a structure shown in formula (II):

[0016]

[0017] Optionally, in some embodiments of the present application, D1 and D3 are selected from one of the following substituted or unsubstituted structures:

[0018]

[0019] Among them, each Z 1 Each independently selected from C or N, Z 2 Selected from C, N, O, Si or S.

[0020] Optionally, in some embodiments of the present application, D1 and D3 are selected from one of the following substituted or unsubstituted structures:

[0021]

[0022] wherein R4 and R5 are each independently selected from substituted or unsubstituted C1-C6 alkyl or substituted or unsubstituted C7-C 12 One or more of the phenylalkyl groups, m1 is selected from any integer in the range of 0 to 8, m2 is selected from any integer in the range of 0 to 10, m3 is selected from any integer in the range of 0 to 7, and m4 is selected from any integer in the range of 0 to 6.

[0023] Optionally, in some embodiments of the present application, D1 and D3 are selected from any one of Formulas 1-1 to 1-22:

[0024]

[0025]

[0026] Optionally, in some embodiments of the present application, R1, R2, and R3 are selected from substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1~C 12 Alkoxy, substituted or unsubstituted C7~C 18 Phenylalkyl, substituted or unsubstituted C7~C 18 Any one of phenylalkoxy; and / or

[0027] D4 and D5 are independently selected from substituted or unsubstituted benzene, anthracene, naphthalene or biphenyl; and / or

[0028] D2 is selected from any one of formulas 2-1 to 2-33:

[0029]

[0030]

[0031] Optionally, in some embodiments of the present application, the organic compound includes one or more of the following structural formulas:

[0032]

[0033]

[0034]

[0035] Accordingly, the present invention also provides a method for preparing an organic compound, comprising: preparing the organic compound by the following synthetic route:

[0036]

[0037] Wherein, the organic compound is M1 or M2,

[0038] R1, R2, and R3 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted phenylalkyl, substituted or unsubstituted C7~C 36 One or more of phenylalkoxy groups;

[0039] Ar1 and Ar2 are each independently selected from the following structures:

[0040]

[0041] Wherein, D1, D2, D3, D4, and D5 are selected from substituted or unsubstituted aryl groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaryl groups having 5 to 60 ring atoms, or a combination thereof;

[0042] n1 and n2 are each independently selected from integers of 0-4.

[0043] Optionally, in some embodiments of the present application, the preparation method comprises: under inert gas protection conditions, mixing compound 1 with a first halogenated hydrocarbon under alkaline conditions to generate compound 2;

[0044] Under inert gas protection conditions, compound 2 is first mixed with a first halogenating agent for reaction, and then mixed with o-nitrophenylboric acid for reaction under palladium catalyst conditions to generate compound 3;

[0045] Under inert gas protection conditions, the compound 3, triethyl phosphite and o-dichlorobenzene are mixed and reacted to generate compound 4;

[0046] The compound 4 is mixed with a second halogenated hydrocarbon under alkaline conditions to react to generate a compound 5;

[0047] The compound 5 is mixed with an oxidant to react to generate a compound M1;

[0048] Wherein, the compound M1 is the organic compound, or the preparation method of the organic compound further comprises:

[0049] The compound M1 is first mixed with a second halogenating agent for reaction, and then mixed with an aromatic compound for reaction under palladium catalyst conditions to generate a compound M2, wherein M2 is the organic compound.

[0050] Optionally, in some embodiments of the present application, the molar ratio of the compound 1 to the first halogenated hydrocarbon is 1:(1-2); and / or

[0051] In the process of mixing compound 1 with the first halogenated hydrocarbon under alkaline conditions to generate compound 2 under inert gas protection conditions, the reaction temperature is 80-110° C.; and / or

[0052] In the process of mixing compound 1 with the first halogenated hydrocarbon under alkaline conditions to generate compound 2 under inert gas protection conditions, the reaction time is 6 to 24 hours; and / or

[0053] The molar ratio of the compound 2 to the first halogenating agent is 1:(2-4); and / or

[0054] The molar ratio of the compound 2 to the o-nitrobenzeneboric acid is 1:(2-4); and / or

[0055] In the process of mixing compound 2 with a first halogenating agent under inert gas protection and then mixing with o-nitrophenylboric acid under palladium catalyst to generate compound 3, the reaction temperature is 80-110° C.; and / or

[0056] In the process of first mixing compound 2 with a first halogenating agent under inert gas protection conditions and then mixing compound 2 with o-nitrophenylboric acid under palladium catalyst conditions to generate compound 3, the reaction time is 12 to 24 hours; and / or

[0057] The molar ratio of the compound 3 to the triethyl phosphite is 1:(40-60); and / or

[0058] In the process of mixing the compound 3, triethyl phosphite and o-dichlorobenzene to generate the compound 4 under the protection of inert gas, the reaction temperature is 140-170° C.; and / or

[0059] In the process of mixing the compound 3, triethyl phosphite and o-dichlorobenzene to generate the compound 4 under the protection of inert gas, the reaction time is 12 to 24 hours; and / or

[0060] The molar ratio of the compound 4 to the second halogenated hydrocarbon is 1:(2-4); and / or

[0061] In the process of mixing the compound 4 with the second halogenated hydrocarbon under alkaline conditions to generate the compound 5, the reaction temperature is 80-110° C.; and / or

[0062] In the process of mixing the compound 4 with the second halogenated hydrocarbon under alkaline conditions to generate the compound 5, the reaction time is 6 to 24 hours; and / or

[0063] The molar ratio of the compound 5 to the oxidant is 1:(40-80); and / or

[0064] In the process of mixing the compound 5 with an oxidant to generate the compound M1, the reaction temperature is 40 to 60° C.; and / or

[0065] In the process of mixing the compound 5 with the oxidant to generate the compound M1, the reaction time is 12 to 24 hours; and / or

[0066] The molar ratio of the compound M1 to the second halogenating agent is 1:(2-4); and / or

[0067] The molar ratio of the compound M1 to the aromatic compound is 1:(2-4); and / or

[0068] The compound M1 is first mixed with a second halogenating agent for reaction, and then mixed with an aromatic compound under palladium catalyst conditions to generate a compound M2, wherein M2 is the organic compound, and the reaction temperature is 80-110° C.; and / or

[0069] In the process of first mixing the compound M1 with the second halogenating agent for reaction, and then mixing with the aromatic compound for reaction under the condition of palladium catalyst to generate the compound M2, the reaction time is 12 to 24 hours.

[0070] Correspondingly, an embodiment of the present application further provides an electron transport material, including the above-mentioned organic compound, or an organic compound prepared by the above-mentioned method for preparing the organic compound.

[0071] Correspondingly, an embodiment of the present application also provides an electronic device, including the above-mentioned organic compound, or including an organic compound prepared by the above-mentioned method for preparing the organic compound, or including the above-mentioned electron transport material.

[0072] Optionally, in some embodiments of the present application, the electronic device is an organic electroluminescent device, a quantum dot electroluminescent device, an organic photovoltaic cell, an organic field effect transistor, an organic light-emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor, or an organic plasma laser emitting diode.

[0073] Optionally, in some embodiments of the present application, the electronic device includes an electronic functional layer, and the electronic functional layer includes the above-mentioned organic compound, or includes an organic compound prepared by the above-mentioned method for preparing the organic compound, or includes the above-mentioned electron transport material.

[0074] Optionally, in some embodiments of the present application, the electronic device is a photoelectric device, and the photoelectric device includes: a first electrode and a second electrode arranged opposite to each other; an electronic functional layer, arranged between the first electrode and the second electrode; wherein the material of the electronic functional layer includes the above-mentioned organic compound, or includes an organic compound obtained by the preparation method of the organic compound as mentioned above, or includes the above-mentioned electron transport material.

[0075] Optionally, in some embodiments of the present application, the optoelectronic device includes a light-emitting layer, the light-emitting layer is arranged between the first electrode 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 a single structure quantum dot, a core-shell structure quantum dot, and a perovskite semiconductor material, and the single structure quantum dot is selected from II-VI group compounds, IV- At least one of a Group VI compound, a Group III-V compound, and a Group I-III-VI compound, wherein the Group II-VI compound is selected from 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, Cd At least one of HgSeTe, CdHgSTe, 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, 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 , at least one of 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, and the I-III-VI group compound is at least one selected from 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;

[0076] And / or, the first electrode and the second electrode 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, ITZO, ICO, AMO, SnO2, In2O3, Cd:ZnO, Ga:SnO2; the material of 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 and ZnS / Al / ZnS;

[0077] And / or, the photoelectric device further comprises a hole functional layer, the hole functional layer is arranged between the first electrode and the light-emitting layer, and the hole functional layer comprises a hole injection layer and / or a hole transport layer; wherein the material of the hole transport layer 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) 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, WSe3, CuS, CuSCN or one or more thereof; wherein the aromatic amine is selected from 4,4'-bis(9-carbazole)biphenyl, poly(9,9-dioctylfluorene-CO-N-(4-butylphenyl)diphenylamine), poly(N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)diphenylamine), N,N'-bis(4-(N,N'-diphenyl-amino) triphenylamine, 4,4',4"-tri(carbazol-9-yl)triphenylamine, 4,4',4"-tri(N-carbazolyl)triphenylamine, 4,4',4"-tri(N-3-methylphenyl-N-phenylamino)triphenylamine, 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, N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4'-diamine, -diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine, Spiro-NPB, Spiro-TPD, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-spiro, Spiro-NPB; the poly(p-)phenylene vinylene and its derivatives are selected from one or more of poly(phenylene vinylene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene] and poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylene vinylene];The material of the hole injection layer is selected from poly(ethylenedioxythiophene): polystyrene sulfonate, 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinone-dimethane, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene, copper phthalocyanine, poly(9,9-dioctyl-fluorene-co-N-(4-butylphenyl)-diphenylamine), polyarylamine, poly(N-vinylcarbazole), polyaniline, polypyrrole, N,N,N',N'-tetrakis(4-methoxyphenyl)-benzidine, 4-bis[N-(1-naphthyl)-N-phenyl-amino]biphenyl, 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine, 4,4' ,4"-tri(N-carbazolyl)-triphenylamine (TCTA), 1,1-bis[(di-4-tolylamino)phenylcyclohexane, 4,4',4"-tri(diphenylamino)triphenylamine doped with F4-TCNQ, p-doped phthalocyanine, F4-TCNQ doped N,N'-diphenyl-N,N'-di(1-naphthyl)-1,1'-biphenyl-4,4"-diamine, transition metal oxides, transition metal sulfur compounds; wherein the transition metal oxides include one or more of NiO, MoO2, WO3, and CuO; the metal sulfur compounds include one or more of MoS2, MoSe2, WS3, WSe3, and CuS.;

[0078] Correspondingly, an embodiment of the present application also provides an electronic device, comprising the above-mentioned optoelectronic device.

[0079] Optionally, in some embodiments of the present application, the electronic device includes a display device, and the display device includes the above-mentioned optoelectronic device.

[0080] The present application provides an organic compound, which is a bissulfone benzopyrrole organic compound. Since it has multiple electron-rich nitrogen atoms, it has good electron injection ability, and the introduction of sulfone groups can effectively adjust its own LUMO energy level; and its large conjugated linear structure is conducive to electron transmission. BRIEF DESCRIPTION OF THE DRAWINGS

[0081] 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.

[0082] Figure 1 It is a schematic flow chart of an embodiment of a method for preparing an organic compound provided in the present application;

[0083] Figure 2This is a schematic structural diagram of an embodiment of a photoelectric device provided by the present application.

[0084] Reference numerals: optoelectronic device 100 ; first electrode 10 ; second electrode 20 ; electronic functional layer 30 ; light emitting layer 40 ; hole functional layer 50 , hole injection layer 51 , hole transport layer 52 . DETAILED DESCRIPTION

[0085] 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.

[0086] 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.

[0087] 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.

[0088] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0089] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0090] 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 a substituent such as 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, or a combination thereof.

[0091] 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.

[0092] 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.

[0093] 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.

[0094] 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.

[0095] 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.

[0096] 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).

[0097] In the present application, "phenylalkyl" refers to phenyl substituted with an alkyl group, and the alkyl group may refer to the description above. Suitable examples include, but are not limited to, tolyl, ethylphenyl, etc. 30 The C1~C 30 is the number of carbon atoms in the alkyl group.

[0098] In the present application, "phenylalkoxy" 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.

[0099] In the present application, "*" indicates a connection site or a fusion site. When the connection site is not specified in the group, it indicates that an optional connection site in the group is used as the connection site. When the fusion site is not specified in the group, it indicates that an optional fusion site in the group is used as the fusion site, and preferably two or more sites in the ortho position in the group are fusion sites.

[0100] 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 position in the ring.

[0101] In the present application, when the same substituent appears multiple times, it can be independently selected from different groups. For example, the above general formula may contain m1 R4, and each R4 can be independently selected from different groups.

[0102] 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.

[0103] The present application provides an organic compound having a structure shown in formula (I):

[0104]

[0105] wherein 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 Phenylalkyl, substituted or unsubstituted C7~C 36 A combination of one or more of phenylalkoxy;

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

[0107]

[0108] Wherein, D1, D3, D4, and D5 are selected from substituted or unsubstituted aryl groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaryl groups having 5 to 60 ring atoms, or combinations thereof;

[0109] D2 is selected from H, D, a substituted or unsubstituted aryl group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, or a combination thereof;

[0110] n1 and n2 are each independently selected from integers of 0-4.

[0111] 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.

[0112] Furthermore, when the organic compound is used as an electronic functional material in a photoelectric device, it is beneficial to balance the injection balance of holes and electrons, thereby improving the luminous efficiency of the photoelectric device, and the stable molecular structure can increase the life of the photoelectric device.

[0113] In one embodiment, 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 Phenylalkyl, substituted or unsubstituted C7~C 36 A combination of one or more of the phenylalkoxy groups.

[0114] Understandable, C7~C 36 In the phenylalkyl group, the benzene ring itself has 6 carbon atoms, so the alkyl group is C1~C 30 Similarly, C7~C 36 In the phenylalkoxy group, the benzene ring itself has 6 carbon atoms, so the alkoxy group is C1~C 30 .

[0115] In one embodiment, R1, R2, and R3 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted C1-C 12 Alkyl, substituted or unsubstituted C1~C 12 Alkoxy, substituted or unsubstituted C1~C 18 Phenylalkyl, substituted or unsubstituted C7~C 18 Any of the phenylalkoxy groups.

[0116] In one embodiment, R1, R2, and R3 are selected from substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1~C 12Alkoxy, substituted or unsubstituted C1~C 18 Phenylalkyl, substituted or unsubstituted C7~C 18 Any of the phenylalkoxy groups.

[0117] In one embodiment, R1, R2, and R3 are linear or branched C1-C 12 Alkyl, straight chain or branched C1~C 12 Any of the alkoxy groups.

[0118] 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.

[0119] In one embodiment, R1, R2, and R3 are selected from the same substituent. In another embodiment, R1, R2, and R3 can also be selected from different substituents; or, any two of R1, R2, and R3 are selected from the same substituent.

[0120] In one embodiment, R1, R2, and R3 are all selected from C1 to C 12 Further, in one embodiment, R1, R2, and R3 are all selected from C1 to C 12 Alkyl and R1, R2, R3 are selected from the same substituent.

[0121] In one embodiment, n1 and n2 are each independently selected from integers of 1 to 4, such as each independently selected from 1, 2, 3 or 4.

[0122] In one embodiment, n1 is selected from 1, and n2 is selected from 1.

[0123] In one embodiment, n1 is selected from 1, and n2 is selected from 2, 3 or 4.

[0124] In one embodiment, n1 is selected from 2, 3 or 4, and n2 is selected from 1.

[0125] In one embodiment, n1 Ar1s may be connected at any one, any two, or any three sites of a1, b1, c1, and d1 in the following structure, or four Ar1s may be connected at the four sites of a1, b1, c1, and d1.

[0126] In one embodiment, n2 Ar2s can be connected at any one, any two, or any three sites among a2, b2, c2, and d2 in the following structure, or four Ar2s can be connected at the four sites of a2, b2, c2, and d2.

[0127]

[0128] In one embodiment, Ar1 is connected at the b1 site, Ar2 is connected at the b2 site, and the organic compound has a structure shown in formula (II):

[0129]

[0130] In one embodiment, Ar1 and Ar2 are each independently selected from different groups; in another embodiment, Ar1 and Ar2 are the same group. For example, Ar1 and Ar2 are both H; or one of Ar1 and Ar2 is H, and the other is selected from a substituted or unsubstituted aryl group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, or a combination thereof. For another example, Ar1 and Ar2 are both selected from a substituted or unsubstituted aryl group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, or a group selected from a combination thereof; or Ar1 and Ar2 are respectively selected from two different substituents selected from a substituted or unsubstituted aryl group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, or a combination thereof.

[0131] In one embodiment, D1 and D3 are selected from one of the following substituted or unsubstituted structures:

[0132]

[0133] Among them, each Z 1 Each independently selected from C or N, Z 2 Selected from C, N, O, Si or S.

[0134] In this embodiment, Ar1 and Ar2 are aromatic groups containing heteroatoms such as N, O, and S, which can provide additional electron clouds and improve the electron transport and injection properties of the organic compound.

[0135] In one embodiment, each Z 1 All selected from C, Z 2 Selected from C, N, O, Si or S.

[0136] In one embodiment, each Z 1 All selected from C, Z 2 Selected from N, O, Si or S.

[0137] In one embodiment, any Z 1 Select from N, the remaining Z 1 All selected from C.

[0138] In one embodiment, any two Z 1 Select from N, the remaining Z 1are all selected from C. Further, in the above structure, each of the two non-adjacent aromatic rings has a Z 1 Select from N, the remaining Z 1 All selected from C.

[0139] In one embodiment, D1 and D3 are selected from one of the following substituted or unsubstituted structures:

[0140]

[0141]

[0142] wherein R4 and R5 are each independently selected from a substituted or unsubstituted C1-C6 alkyl chain, or a substituted or unsubstituted C7-C 12 One or more of the phenylalkyl chains, m1 is selected from any integer from 0 to 8, m2 is selected from any integer from 0 to 10, m3 is selected from any integer from 0 to 7, and m4 is selected from any integer from 0 to 6.

[0143] Specifically, m1 is any integer selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, m2 is any integer selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, m3 is any integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and m4 is any integer selected from 0, 1, 2, 3, 4, 5, 6.

[0144] In one embodiment, D1 and D3 are selected from any one of Formulas 1-1 to 1-31:

[0145]

[0146] In one embodiment, D4 and D5 are independently selected from substituted or unsubstituted benzene, anthracene, naphthalene or biphenyl.

[0147] Further, D4 and D5 are independently selected from benzene, anthracene, naphthalene or biphenyl.

[0148] In one embodiment, D2 is selected from H, or any one of Formulas 2-1 to 2-33:

[0149]

[0150] In one embodiment, the organic compound comprises one or more of the following structural formulas:

[0151]

[0152]

[0153]

[0154] The present application provides a method for preparing an organic compound, and the organic compound can be prepared through the following synthetic route. or

[0155]

[0156] Wherein, the organic compound is M1 or M2,

[0157] R1, R2, and R3 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted phenylalkyl, substituted or unsubstituted C7~C 36 One or more of phenylalkoxy groups;

[0158] Ar1 and Ar2 are each independently selected from the following structures:

[0159]

[0160] Wherein, D1, D2, D3, D4, and D5 are selected from substituted or unsubstituted aryl groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaryl groups having 5 to 60 ring atoms, or a combination thereof;

[0161] n1 and n2 are each independently selected from integers of 0-4.

[0162] Further, the preparation method of the organic compound, see Figure 1 , Figure 1 1 is a flow chart of an embodiment of a method for preparing an organic compound provided in the present application, which specifically comprises the following steps:

[0163] Step S11: under inert gas protection conditions, compound 1 and a first halogenated hydrocarbon are mixed and reacted under alkaline conditions to generate compound 2;

[0164] Step S12: under inert gas protection, compound 2 is first mixed with a first halogenating agent to undergo a halogenation reaction, and then mixed with o-nitrophenylboric acid under palladium catalyst conditions to undergo a Suzuki coupling reaction to obtain compound 3;

[0165] Step S13: Under inert gas protection conditions, compound 3, triethyl phosphite and o-dichlorobenzene are mixed and reacted to generate compound 4;

[0166] Step S14: mixing compound 4 with a second halogenated hydrocarbon under alkaline conditions to generate compound 5 by carbon-carbon coupling reaction;

[0167] Step S15: Compound 5 is mixed with an oxidant to undergo an oxidation reaction to obtain compound M1;

[0168] Wherein, the compound M1 is the organic compound, or the preparation method of the organic compound further comprises:

[0169] Step S16: Compound 6 is first mixed with a second halogenating agent to undergo a halogenation reaction, and then mixed with a corresponding aromatic compound under palladium catalyst conditions to undergo a Suzuki coupling reaction to obtain compound M2, wherein M2 is the organic compound.

[0170] It can be understood that 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.

[0171] In the step S11:

[0172] In one embodiment, the molar ratio of compound 1 to the first halogenated hydrocarbon is 1:(1-2), specifically 1:(1-1.2), 1:(1.2-1.5), 1:(1.5-1.8), 1:(1.8-1.9), etc.

[0173] The first halogenated hydrocarbon may be selected from halogenated alkyl chains or halogenated aromatic hydrocarbons.

[0174] Furthermore, the reaction temperature of this step is 80-110° C., and the reaction time is 6-24 h.

[0175] In step S12:

[0176] The first halogenating agent may include N-bromosuccinimide (NBS), N-iodosuccinimide (NIS), and the like.

[0177] In one embodiment, the molar ratio of the compound 2 to the first halogenating agent is 1:(2-4), specifically 1:(2-3.5), 1:(2.5-3.5), 1:(2.5-3), etc.

[0178] In one embodiment, the molar ratio of compound 2 to o-nitrobenzene boronic acid is 1:(2-4), specifically 1:(2-3.5), 1:(2.5-3.5), 1:(2.5-3), etc. The molar ratio can connect two o-nitrophenyl groups to compound 2, and also avoid waste of materials caused by excessive o-nitrobenzene boronic acid.

[0179] Furthermore, the reaction temperature of this step is 80-110° C., and the reaction time is 12-24 h.

[0180] In step S13:

[0181] In one embodiment, the molar ratio of the compound 3 to triethyl phosphite is 1:(40-60), specifically 1:(40-55), 1:(45-55), 1:(45-50), 1:(40-45), 1:(55-60), etc.

[0182] Furthermore, the reaction temperature of this step is 140-170° C., and the reaction time is 12-24 h.

[0183] In step S14:

[0184] In one embodiment, the molar ratio of the compound 4 to the second halogenated hydrocarbon is 1:(2-4), specifically 1:(2-3.5), 1:(2.5-3.5), 1:(2.5-3), etc.

[0185] The second halogenated hydrocarbon may be selected from a halogenated alkyl chain or a halogenated aromatic hydrocarbon.

[0186] The second halogenated hydrocarbon includes R2-X and R3-X, wherein R2 and R3 may be the same or different.

[0187] Furthermore, the reaction temperature of this step is 80-110° C., and the reaction time is 6-24 h.

[0188] In one embodiment, R2 and R3 are selected from the same substituent.

[0189] In another embodiment, R2 and R3 are selected from different substituents, and the step S14 can be performed by directly mixing the compound 4 with the second halogenated hydrocarbon formed by mixing R2-X and R3-X to obtain the compound 5; or the compound 4 can be first mixed with one of R2-X and R3-X to obtain a mixture, and then the mixture is mixed with the other of R2-X and R3-X to obtain the compound 5.

[0190] In step S15:

[0191] In one embodiment, the oxidant may be selected from hydrogen peroxide. It is understandable that other oxidants capable of oxidizing sulfur to sulfone are also applicable to this step of the present application, which is not limited here.

[0192] In one embodiment, the molar ratio of compound 5 to the oxidant is 1:(40-80), specifically 1:(40-75), 1:(45-75), 1:(45-70), 1:(50-70), 1:(50-65), 1:(55-65), 1:(55-60), etc.

[0193] Furthermore, the reaction temperature of this step is 40-60° C., and the reaction time is 12-24 h.

[0194] In step S16:

[0195] The second halogenating agent may include N-bromosuccinimide (NBS), N-iodosuccinimide (NIS), and the like.

[0196] In one embodiment, the molar ratio of compound M1 to the second halogenating agent is 1:(2-4), specifically 1:(2-3.5), 1:(2.5-3.5), 1:(2.5-3), etc.

[0197] In one embodiment, the molar ratio of compound M1 to the aromatic compound is 1:(2-4), specifically 1:(2-3.5), 1:(2.5-3.5), 1:(2.5-3), etc.

[0198] Furthermore, the reaction temperature of this step is 80-110° C., and the reaction time is 12-24 h.

[0199] When Ar1 and Ar2 are the same group, compound M2 can be obtained by a single Suzuki coupling reaction. When Ar1 and Ar2 are independently selected from different groups, compound M2 can be obtained by a single Suzuki coupling reaction, and Ar1 and Ar2 can be connected to compound M1; or Ar1 and Ar2 can be connected to compound M1 by two Suzuki coupling reactions.

[0200] 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.

[0201] 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.

[0202] The present application provides an electron transport material, including the organic compound provided by the present application.

[0203] In one embodiment, the electron transport material, in addition to the organic compound, may also include other conductive materials or semiconductor materials, such as inorganic nanomaterials such as zinc oxide and titanium dioxide, and other organic conductive materials.

[0204] In another embodiment, the electron transport material consists of the organic compound.

[0205] The present application provides an electronic device, including the organic compound provided by the present application, or including the electron transport material provided by the present application.

[0206] In one embodiment, the electronic device is an organic electroluminescent device, a quantum dot electroluminescent device, an organic photovoltaic cell, a thin film solar cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor, or an organic plasma laser emitting diode.

[0207] In one embodiment, the electronic device includes an electronic functional layer, and the electronic functional layer includes the organic compound provided in the present application, or includes the electron transport material provided in the present application.

[0208] In one embodiment, the electronic device is the organic electroluminescent device or the quantum dot electroluminescent device, and the electronic device further includes a light-emitting layer.

[0209] The present application also provides the use of the organic compound in a light emitting diode device, a field effect transistor or a thin film solar cell.

[0210] The present application also provides an electron transport layer comprising the organic compound, and application of the electron transport layer in a light emitting diode device, a field effect transistor or a thin film solar cell.

[0211] In one embodiment, the electronic device is a photoelectric device. Figure 2 , Figure 2 The present application provides a schematic structural diagram of an embodiment of a photoelectric device, wherein the photoelectric device 100 includes a first electrode 10 and a second electrode 20 that are relatively arranged, and an electronic functional layer 30 that is arranged between the first electrode 10 and the second electrode 20, and the material of the electronic functional layer 30 includes the organic compound provided in the present application, or includes an organic compound obtained by the preparation method of the organic compound provided in the present application.

[0212] In this embodiment, the material of the electronic functional layer 30 includes a bissulfone benzopyrrole organic compound. On the one hand, since it has multiple electron-rich nitrogen atoms, it has good electron injection ability, and the introduction of the sulfone group can effectively adjust its own LUMO energy level, and its large conjugated linear structure is conducive to electron transmission, thereby improving the performance of the optoelectronic device 100; on the other hand, the bissulfone benzopyrrole organic compound has a relatively stable molecular structure, which can improve the material stability of the electronic functional layer 30, thereby increasing the life of the optoelectronic device 100.

[0213] 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.

[0214] 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.

[0215] 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.

[0216] 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 first electrode 10 and the electronic functional layer 30 .

[0217] 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.

[0218] In one embodiment, the material of the light-emitting layer 40 is selected from organic light-emitting materials or quantum dot light-emitting materials.

[0219] The organic light-emitting material may 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;

[0220] 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 , 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 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;

[0221] 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+ 、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 - 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.

[0222] In one embodiment, the quantum dot luminescent material includes one or more of red quantum dots, green quantum dots, and blue quantum dots.

[0223] In one embodiment, the optoelectronic device 100 further includes a hole functional layer 50, and the hole functional layer 50 is disposed between the first electrode 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 first electrode 10, and the hole transport layer 52 is disposed close to the light-emitting layer 40.

[0224] 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).

[0225] 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.

[0226] In one embodiment, the first electrode 10 and the second electrode 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, I At least one of TZO, 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.

[0227] The first electrode 10 and the second electrode 20 form a pair of electrodes. In one embodiment, the first electrode 10 is an anode, and the second electrode 20 is a cathode.

[0228] 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.

[0229] 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 .

[0230] The optoelectronic device 100 further includes a substrate (not shown), which may also be referred to as a substrate. The substrate may be a rigid substrate or a flexible substrate. The rigid substrate may be a ceramic material or various glass materials. 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 glass, silicon wafer, polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate, polyamide, polyether sulfone, or a combination thereof.

[0231] It can be understood that the optoelectronic device 100 can be an upright optoelectronic device or an inverted optoelectronic device. When the optoelectronic device 100 is an upright optoelectronic device, the substrate is combined with the side of the first electrode 10 away from the light-emitting layer 40. When the optoelectronic device 100 is an inverted optoelectronic device, the substrate is combined with the side of the second electrode 20 away from the light-emitting layer 40.

[0232] 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.

[0233] 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 .

[0234] 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 first electrode 10, the second electrode 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 method, anodization method, electrolytic deposition method, and coprecipitation method. The physical method includes physical plating method and solution method, among which the physical plating method includes: thermal evaporation coating method, electron beam evaporation coating method, magnetron sputtering method, multi-arc ion plating method, physical vapor deposition method, atomic layer deposition method, pulsed laser deposition method, etc.; the solution method can be spin coating, printing method, inkjet printing method, doctor blade method, printing method, dip pulling method, immersion method, spraying method, roll coating method, casting method, slit coating method and strip coating method, etc.

[0235] 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.

[0236] The present application also relates to the application of the electronic device described in the present application in an electronic device. Specifically, the electronic device may include a display device, a battery device, a sensing device, etc.

[0237] 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.

[0238] 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.

[0239] Embodiment 1:

[0240] The synthetic route of the organic compound M1-1 in this example is as follows:

[0241]

[0242] Preparation of organic compound M1-1:

[0243] Step 1: Compound 1 (4 mmol, 716 mg) was added to a 100 mL two-necked bottle, and 1-bromooctane (10 mmol, 1930 mg) and potassium hydroxide (2.26 mmol, 557 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, and the reaction was continued for 24 hours. The reaction was stopped and cooled to room temperature, and the reaction solution was extracted, and 200 ml of water and 1500 ml of dichloromethane were used to extract repeatedly 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 and purified and separated using column chromatography. The eluent used petroleum ether, dichloromethane and ethyl acetate (volume ratio of 200:1:1), and finally compound 2 was obtained as a white solid of 140 mg with a yield of 90%; the melting point was 106 ° C.

[0244] Step 2: Add compound 2 (4mmol, 1055mg) to a 100mL two-necked bottle, dissolve in 40mL chloroform, dissolve N-bromosuccinimide (NBS) (8mmol, 1424mg) in 10mL chloroform, 40mL chloroform, stir for 3h in an ice bath, monitor the complete reaction of the raw materials by thin layer chromatography (TLC), and then stop the reaction. The reaction solution is distilled under reduced pressure to remove the solvent. The crude product is mixed with 200 to 300 mesh silica gel and separated by column chromatography. The mobile phase is petroleum ether: ethyl acetate (volume ratio is 20:1) to obtain the intermediate crude product; in a 100mL two-necked round-bottom flask, the intermediate product, 2-nitrophenylboronic acid (4mmol, 668mg), potassium phosphate aqueous solution (2M, 0.4mL), catalyst Pd(PPh3)4 (58mg, 0.05mmol), 30mL redistilled toluene and 5mL ethanol are added in sequence. Stir the reaction at 90°C for 24h under nitrogen atmosphere. After the reaction was completed, the reaction was quenched with deionized water, and then extracted three times with dichloromethane and water respectively, and then dried with a desiccant, and rotary evaporated to obtain a crude product. The crude product was purified by column chromatography using a silica gel column, and the eluent was ethyl acetate, dichloromethane and petroleum ether (volume ratio of 1:1:20), and finally compound 3 was obtained as a solid product of 1.4 g, with a total yield of 70% in two steps; melting point 152-155°C.

[0245] Step 2: Add compound 3 (1 mmol, 505 mg), PPh3 (10 mmol, 2.62 g) and 20 ml of ultra-dry o-dichlorobenzene (ODB) to a 100 mL single-mouth bottle, introduce nitrogen and use a vacuum pump to evacuate for 30 minutes, stir and heat to reflux, continue the reaction for 24 hours, stop the reaction, remove o-dichlorobenzene by vacuum distillation, and separate the crude product by column chromatography. The eluent used is petroleum ether, dichloromethane and ethyl acetate (volume ratio of 12:1:1), and finally obtain compound 4 as a solid product 88 mg, with a yield of 20%; melting point 173-176 ° C.

[0246] Step 3: Compound 4 (1 mmol, 441 mg) was added to a 100 ml two-necked bottle, and 1-bromohexane (2.26 mmol, 480 mg) and potassium hydroxide (2.26 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, and the reaction was continued for 24 hours. The reaction was stopped and cooled to room temperature, and 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), and finally compound 5 was obtained as a light yellow solid of 140 mg with a yield of 20%; the melting point was 106 ° C.

[0247] Step 4: Add compound 5 (1mmol, 609mg) 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 10:1) as the eluent; finally, 538mg of solid product, namely compound M1-1, is obtained with a yield of 80%. 1 H NMR(500MHz,Chloroform-d)δ8.15–8.10(m,2H),7.60–7.52(m,2H),7.39–7.33(m,2H),7.33–7.25(m,2 H),4.19–4.12(m,2H),4.07(t,J=6.2Hz,4H),1.76–1.64(m,6H),1.41–1.21(m,26H),0.94–0.85(m,9H).

[0248] Embodiment 2:

[0249] Preparation of organic compound M1-2:

[0250]

[0251] The synthesis of the organic compound M1-2 of this example is similar to that of M1-1, except that in Example 1, 1-bromooctane in step 1 is replaced with 1-butoxy-4-iodobenzene (CAS: 96693-04-8), and 1-bromohexane in step 4 is replaced with 1-bromoethane. The reaction conditions and the amount of substance are not changed, and a light yellow solid product M1-2 is finally obtained. 1HNMR(500MHz,Chloroform-d)δ8.17–8.11(m,2H),7.60–7.53(m,2H),7.50–7.44(m,2H),7.44–7.37(m,2H),7.38–7.31(m,2H),7.08–7 .02(m,2H),4.25(t,J=7.1Hz,4H),3.98(t,J=6.1Hz,2H),1.81–1.72(m,2H),1.55–1.44(m,2H),1.38–1.31(m,6H),1.01–0.94(m,3H).

[0252] Embodiment 3:

[0253] Preparation of organic compound M1-3:

[0254]

[0255] The synthesis of the organic compound M1-3 of this example is similar to that of M1-1, except that in Example 1, the 1-bromooctane in step 1 is replaced by 1-n-octyl-4-iodobenzene, and the 1-bromohexane in step 4 is replaced by 1-bromoheptane and 1-methoxy-4-iodobenzene (the amount of the substance is halved accordingly). The other reaction conditions and the amount of the substance are not changed, and finally a light yellow solid product M1-3 is obtained. 1 HNMR(500MHz,Chloroform-d)δ8.27–8.21(m,1H),8.15–8.09(m,1H),7.65–7.59(m,1H),7 .60–7.51(m,2H),7.41(ddd,J=7.9,1.3,0.5Hz,1H),7.37–7.34(m,2H),7.33–7.29(m,1H), 7.29–7.24(m,3H),7.21–7.14(m,2H),7.12–7.05(m,2H),4.09(t,J=6.3Hz,2H),3.78(s,2 H),2.64(tt,J=6.4,1.0Hz,2H),1.73–1.57(m,4H),1.38–1.25(m,18H),0.94–0.85(m,6H).

[0256] Embodiment 4:

[0257] Preparation of organic compound M1-4:

[0258]

[0259] The synthesis of organic compound M1-4 in this example is similar to that of M1-1, except that 1-bromooctane in step 1 is replaced by 1-n-octyl-4-iodobenzene, and 1-bromohexane in step 4 is replaced by 1-methoxy-4-iodobenzene. The reaction conditions and the amount of substances remain unchanged, and a light yellow solid product M1-4 is finally obtained. 48 H 43 N3NaO6S2:860.2224.

[0260] Embodiment 5:

[0261] Preparation of organic compound M2-1:

[0262]

[0263] Compound M1-1 (1 mmol, 673 mg) was added to a 100 mL two-necked bottle and dissolved in 40 mL chloroform. N-bromosuccinimide (NBS) (3 mmol, 534 mg) was dissolved in 10 mL chloroform and 40 mL chloroform. The mixture was stirred for 3 h in an ice bath. The reaction was stopped when the raw materials were 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 10:1) to obtain a crude intermediate product. The intermediate product (1 mmol, 829 mg), phenoxazine (3 mmol, 501 mg), Pd2(dba)3(0 .05mmol, 50mg) and sodium tert-butoxide (5mmol, 480mg) and tert-butylphosphine (5mmol, 450mg), then add 40mL of redistilled toluene, pass nitrogen, use a vacuum pump to evacuate and replace with nitrogen for 15 minutes, cover the reaction bottle with tin foil to avoid light, stir and heat to 110°C for reaction for 24h, stop the reaction, and cool to room temperature, extract the reaction solution, use dichloromethane (1000mL) and water (250mL) to wash repeatedly 3 to 4 times, and the organic phase is dried with anhydrous magnesium sulfate, and crude separation is performed by column chromatography, the developing agent is petroleum ether: dichloromethane: acetone (volume ratio is 20:2:1), and the organic compound M1 is obtained as a white solid 702mg, and the yield is 70%. 1HNMR(500MHz,Chloroform-d)δ8.15–8.11(m,2H),7.59–7.54(m,1H),7.40–7. 36(m,1H),7.33–7.28(m,1H),7.24–7.20(m,1H),7.17–7.15(m,1H),7.13–7.0 6(m,6H),6.72–6.68(m,2H),4.15(t,J=6.3Hz,2H),4.11(t,J=6.2Hz,2H),4.0 7(t,J=6.2Hz,2H),1.74–1.65(m,6H),1.39–1.25(m,22H),0.92–0.87(m,9H).

[0264] Embodiment 6:

[0265] Preparation of organic compound M2-2:

[0266]

[0267] The synthesis of the organic compound M2-2 in this example is similar to that of M2-1, except that in Example 5, compound M1-1 is replaced by M1-2, and phenoxazine is replaced by dimethyldibenzo[b,e][1,4]nitrogen silanol. The reaction conditions and the amount of substance are not changed, and finally a light yellow solid product M2-2 is obtained. 1 HNMR(500MHz,Chloroform-d)δ8.07–8.05(m,1H),8.04–8.02(m,1H),7.57–7.52(m,2H),7.49–7.47(m,2H),7.46–7.32(m,11H),7.06–7.03(m,2H),4 .28–4.24(m,2H),4.23–4.18(m,2H),3.91(t,J=6.0Hz,2H),1.80–1.75(m, 2H),1.49–1.42(m,2H),1.41–1.37(m,6H),0.95–0.91(m,3H),0.53(s,6H).

[0268] Embodiment 7:

[0269] Preparation of organic compound M2-3:

[0270]

[0271] The synthesis of the organic compound M2-3 in this example is similar to that of M2-1, except that in Example 5, compound M1-1 is replaced by M1-4, and phenoxazine is replaced by 5-tert-butyl-5,10-dihydrophenazine. The reaction conditions and the amount of substance are not changed, and finally a light yellow solid product M2-3 is obtained.1 H NMR(500MHz,Chloroform-d)δ8.32–8.30(m,1H),8.20–8.17(m,1H),8.04–8.01(m,1H) ,7.77–7.74(m,2H),7.60–7.59(m,1H),7.45–7.41(m,1H),7.39–7.36(m,2H),7.36–7. 32(m,5H),7.23–7.19(m,3H),7.16–7.14(m,4H),7.09–7.05(m,6H),3.79(s,6H),2.66 –2.63(m,2H),1.66–1.61(m,2H),1.33(s,9H),1.30–1.24(m,10H),0.91–0.87(m,3H).

[0272] Embodiment 8:

[0273] Preparation of organic compound M2-4:

[0274]

[0275] The synthesis of the organic compound M2-3 in this example is similar to that of M2-1, except that phenoxazine is replaced by dimethylphenothiazine in Example 5 (the feed ratio is doubled), and the other reaction conditions and amounts of substances are not changed, and finally a light yellow solid product M2-4 is obtained. 1 H NMR(500MHz,Chloroform-d)δ8.13–8.11(m,2H),7.38–7.35(m,2H),7.17–7.16(m,2H),7.15–7.13(m,4H),7.11–7.10(m, 4H),7.07–7.05(m,4H),4.53–4.39(m,6H),2.22–2.19(m,12H),1.82–1.73(m,6H),1.44–1.25(m,23H),0.92–0.87(m,9H).

[0276] Embodiment 9:

[0277] Preparation of organic compound M2-5:

[0278]

[0279] The synthesis of organic compound M2-5 in this example is similar to that of M2-1, except that phenoxazine is replaced with 3,6-bis(4-methoxyphenyl)-9-hydrogen-carbazole (the feed ratio is doubled) in Example 5, and the other reaction conditions and the amount of substances are not changed, and finally a light yellow solid product M2-5 is obtained. C92H89N5O8S2: 1455.6153.

[0280] Embodiment 10:

[0281] Preparation of organic compound M2-6:

[0282]

[0283] The synthesis of organic compound M2-6 in this example is similar to that of M2-1, except that compound M1-1 is replaced by M1-4 in Example 5, and phenoxazine is replaced by 5-hydro-pyrrole [3,2-c:4,5-c'] bipyridine (the feed ratio is doubled), and the other reaction conditions and the amount of substances are not changed, and finally a light yellow solid product M2-6 is obtained. C58H48N6O6S2: 988.3077

[0284] Embodiment 11:

[0285] Preparation of organic compound M2-7:

[0286]

[0287] The synthesis of organic compound M2-7 in this example is similar to that of M2-1, except that compound M1-1 is replaced by M1-2 and phenoxazine is replaced by 9-(4-iodobenzene)-9-hydrogen-carbazole in Example 5. The other reaction conditions and the amount of substances remain unchanged, and a light yellow solid product M2-7 is finally obtained. C52H42N4O5S2: 866.2597

[0288] Embodiment 12:

[0289] Preparation of organic compound M2-8:

[0290]

[0291] The synthesis of organic compound M2-8 in this example is similar to that of M2-1, except that compound M1-1 is replaced by M1-2 and phenoxazine is replaced by diphenylamine in Example 5. The other reaction conditions and amounts of substances remain unchanged, and a light yellow solid product M2-8 is finally obtained. C46H40N4O5S2: 792.2440

[0292] Embodiment 13:

[0293] Preparation of organic compound M2-9:

[0294]

[0295] The synthesis of organic compound M2-9 in this example is similar to that of M2-1, except that compound M1-1 is replaced by M1-2 and phenoxazine is replaced by phenoxathiol in Example 5. The other reaction conditions and the amount of substances remain unchanged, and a light yellow solid product M2-9 is finally obtained. C46H37N3O6S3: 823.1844

[0296] Embodiment 14:

[0297] Preparation of organic compound M2-10:

[0298]

[0299] The synthesis of organic compound M2-10 in this example is similar to that of M2-1, except that compound M1-1 is replaced by M1-2 in Example 5, and phenoxazine is replaced by 10-methyl-10-hydrogen-phenothiazine (the feed ratio is doubled), and the other reaction conditions and the amount of substances are not changed, and finally a light yellow solid product M2-10 is obtained. C60H49N5O5S4: 1047.2617

[0300] Embodiment 15:

[0301] Preparation of organic compound M2-11:

[0302]

[0303] The synthesis of organic compound M2-11 in this example is similar to that of M2-1, except that compound M1-1 is replaced by M1-2 in Example 5, and phenoxazine is replaced by 1,2-dihydro-9,9'-spirodixanthene and 1,2-dihydro-9,9'-spirodithioanthene. The other reaction conditions and the amount of substances remain unchanged, and finally a light yellow solid product M2-11 is obtained. C84H63N3O7S4: 1353.3549

[0304] Embodiment 16:

[0305] Preparation of organic compound M2-12:

[0306]

[0307] The synthesis of organic compound M2-12 in this example is similar to that of M2-1, except that compound M1-1 is replaced by M1-2 in Example 5, phenoxazine is replaced by 10-(4-iodophenyl)-1',2'-dihydro-10H-spiro[acridine-9,9'-thioxanthene] and 10-(4-iodophenyl)-1',2'-dihydro-10H-spiro[acridine-9,9'-xanthene], and the other reaction conditions and the amount of substances are not changed, and finally a light yellow solid product M2-12 is obtained. C96H73N5O6S3: 1487.4723.

[0308] Embodiment 17:

[0309] Preparation of organic compound M2-13:

[0310]

[0311] The synthesis of organic compound M2-13 in this example is similar to that of M2-1, except that compound M1-1 is replaced by M1-2 and phenoxazine is replaced by

[0312] 10-(4-iodophenyl)-1',2'-dihydro-10H,10"H-dispiro[acridine-9,9'-anthracene-10',9"-anthracene], the other reaction conditions and the amount of substances did not change, and finally a light yellow solid product M2-13 was obtained. C79H62N4O5S2: 1210.4162.

[0313] Embodiment 18:

[0314] Preparation of organic compound M2-14:

[0315]

[0316] The synthesis of organic compound M2-14 in this example is similar to that of M2-1, except that compound M1-1 is replaced by M1-2 in Example 5, and phenoxazine is replaced by triphenylamine (the feed ratio is doubled), and the other reaction conditions and amounts of substances are not changed, and finally a light yellow solid product M2-14 is obtained. C70H57N5O5S2: 1111.3801.

[0317] Embodiment 19:

[0318] Preparation of organic compound M2-15:

[0319]

[0320] The synthesis of organic compound M2-15 in this example is similar to that of M2-14, except that the substitution site is changed from meta to para, and the other reaction conditions and the amount of substances remain unchanged, and finally a light yellow solid product M2-15 is obtained. C70H57N5O5S2: 1111.3801.

[0321] Embodiment 20:

[0322] Preparation of organic compound M2-16:

[0323]

[0324] The synthesis of organic compound M2-16 in this example is similar to that of M2-1, except that compound M1-1 is replaced by M1-2 and phenoxazine is replaced by triphenylamine in Example 5, and the other reaction conditions and amounts of substances are unchanged, and finally a light yellow solid product M2-16 is obtained. C52H44N4O5S2: 868.2753.

[0325] Embodiment 21:

[0326] Preparation of organic compound M2-17:

[0327]

[0328] The synthesis of organic compound M2-17 in this example is similar to that of M2-1, except that phenoxazine is replaced by carbazole in Example 5 (the feed ratio is doubled), and the other reaction conditions and amounts of substances remain unchanged, and finally a light yellow solid product M2-17 is obtained. C64H65N5O4S2: 1031.4478.

[0329] Embodiment 22:

[0330] Preparation of organic compound M2-18:

[0331]

[0332] The synthesis of organic compound M2-18 in this example is similar to that of M2-1, except that phenoxazine is replaced by phenothiazine in Example 5, and the other reaction conditions and amounts of substances remain unchanged, and finally a light yellow solid product M2-18 is obtained. C52H58N4O4S3: 898.3620.

[0333] Embodiment 23:

[0334] Preparation of organic compound M2-19:

[0335]

[0336] The synthesis of organic compound M2-19 in this example is similar to that of M2-1, except that phenoxazine is replaced by diphenylamine and 9,9-dimethyl-9,10-dihydroacridine in Example 5, and the other reaction conditions and amounts of substances are unchanged, and finally a light yellow solid product M2-19 is obtained. C67H73N5O4S2: 1075.5104.

[0337] Embodiment 24:

[0338] Preparation of organic compound M2-20:

[0339]

[0340] The synthesis of organic compound M2-20 in this example is similar to that of M2-1, except that phenoxazine is replaced with 4-iodo-N,N-bis(4-methoxyphenyl)aniline and 9,9-bis(4-methoxyphenyl)-9,10-dihydroacridine in Example 5, and the other reaction conditions and the amount of substances are unchanged, and finally a light yellow solid product M2-20 is obtained. C87H89N5O8S2: 1395.6153.

[0341] Embodiment 25:

[0342] Preparation of organic compound M3-1:

[0343]

[0344]

[0345] Step 1: Add compound 1-1 (4mmol, 1055mg) to a 100mL two-necked bottle, dissolve in 40mL chloroform, dissolve N-bromosuccinimide (NBS) (8mmol, 1424mg) in 10mL chloroform, 40mL chloroform, stir for 3h in an ice bath, monitor the complete reaction of the raw materials by thin layer chromatography (TLC), and then stop the reaction. The reaction solution is distilled under reduced pressure to remove the solvent. The crude product is mixed with 200 to 300 mesh silica gel and separated by column chromatography. The mobile phase is petroleum ether: ethyl acetate (volume ratio is 20:1) to obtain the intermediate crude product; in a 100mL two-necked round-bottom flask, the intermediate product, 2-nitrophenylboronic acid (4mmol, 668mg), potassium phosphate aqueous solution (2M, 0.4mL), catalyst Pd(PPh3)4 (58mg, 0.05mmol), 30mL redistilled toluene and 5mL ethanol are added in sequence. Stir the reaction at 90°C for 24h under nitrogen atmosphere. After the reaction was completed, the reaction was quenched with deionized water, and then extracted three times with dichloromethane and water respectively, and then dried with a desiccant, and rotary evaporated to obtain a crude product. The crude product was purified by column chromatography using a silica gel column, and the eluent was ethyl acetate, dichloromethane and petroleum ether (volume ratio of 1:1:20), and finally compound 1-2 was obtained as a solid product of 1.4 g, with a total yield of 70% in two steps; melting point 152-155°C.

[0346] Step 2: Add compound 1-2 (1 mmol, 505 mg), PPh3 (10 mmol, 2.62 g) and 20 ml of ultra-dry o-dichlorobenzene (ODB) to a 100 mL single-mouth bottle, introduce nitrogen and use a vacuum pump to evacuate for 30 minutes, stir and heat to reflux, continue the reaction for 24 hours, stop the reaction, remove o-dichlorobenzene by vacuum distillation, and separate the crude product by column chromatography. The eluent used is petroleum ether, dichloromethane and ethyl acetate (volume ratio of 12:1:1), and finally obtain compound 1-3 as a solid product 88 mg, with a yield of 20%; melting point 173-176 ° C.

[0347] Step 3: Add compound 1-3 (1 mmol, 441 mg) to a 100 ml two-necked bottle, and weigh and add 1-bromohexane (2.26 mmol, 480 mg), potassium hydroxide (2.26 mmol, 126 mg), add 40 ml of dimethyl sulfoxide, introduce nitrogen and use a vacuum pump to evacuate for 15 minutes, stir and heat to 85 ° C, continue the reaction for 24 hours, stop the reaction and cool to room temperature, extract the reaction solution, use 200 ml of water and 1500 ml of dichloromethane to extract repeatedly 3 to 4 times, and the obtained organic extract is dried with anhydrous magnesium sulfate, and the filtrate is collected and mixed with 200 to 300 mesh silica gel and purified and separated by column chromatography. The eluent uses petroleum ether, dichloromethane and ethyl acetate (volume ratio of 200:1:1), and finally obtains compound M1-4 as a light yellow solid 140 mg, with a yield of 20%; the melting point is 106 ° C.

[0348] Step 4: Add compound 1-4 (1mmol, 609mg) 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 10:1) as the eluent; finally, 538mg of solid product, namely intermediate 1-5, is obtained with a yield of 80%.

[0349] Step 5: Add compound 1-5 (1 mmol, 673 mg) to a 100 mL two-necked bottle, dissolve in 40 mL chloroform, dissolve N-bromosuccinimide (NBS) (3 mmol, 534 mg) in 10 mL chloroform, 40 mL chloroform, stir for 3 h in an ice bath, monitor the complete reaction of the raw materials by thin layer chromatography (TLC), stop the reaction, distill the reaction solution under reduced pressure to remove the solvent, mix the crude product with 200 to 300 mesh silica gel, and separate by column chromatography. The mobile phase is petroleum ether: ethyl acetate (volume ratio of 10:1) to obtain the intermediate crude product M1-6; Add compound M1-6 (1 mmol, 829 mg), 9H-carbazole (3 mmol, 501 mg), Pd2 (db a) 3 (0.05mmol, 50mg) and sodium tert-butoxide (5mmol, 480mg) and tert-butylphosphine (5mmol, 450mg), then add 40mL of redistilled toluene, pass nitrogen, use a vacuum pump to evacuate and replace with nitrogen for 15 minutes, cover the reaction bottle with tin foil to avoid light, stir and heat to 110°C for reaction for 24h, stop the reaction, and cool to room temperature, extract the reaction solution, use dichloromethane (1000mL) and water (250mL) to wash repeatedly 3 to 4 times, and dry the organic phase with anhydrous magnesium sulfate, use column chromatography for crude separation, the developing agent is petroleum ether: dichloromethane: acetone (volume ratio is 20:2:1), and the organic compound M3-1 is obtained as a white solid 702mg, and the yield is 70%. The nuclear magnetic resonance data are as follows: 1H NMR (400 MHz, CDCl3) δ8.21-8.19 (m, 2H), 8.02-7.99 (m, 4H), 7.51-7.48 (m, 8H), 7.27-7.23 (m, 4H), 7.20-7.16 (m, 4H), 4.17 (t, J = 6.3 Hz, 2H), 4.10 (t, J = 6.2 Hz, 4H), 1.73-1.65 (m, 6H), 1.40-1.26 (m, 18H), 0.92-0.87 (m, 9H).

[0350] Embodiment 26:

[0351] Preparation of organic compound M3-2:

[0352]

[0353] Compound 1-5 (1 mmol, 673 mg) was added to a 100 mL two-necked bottle and dissolved in 40 mL chloroform. N-bromosuccinimide (NBS) (1 mmol, 178 mg) was dissolved in 10 mL chloroform and 40 mL chloroform. The mixture was stirred for 3 h in an ice bath. 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 10:1) to obtain the intermediate crude product 1-7. Compound 1-7 (1 mmol, 751 mg), phenothiazine (1.5 mmol, 298.5 mg), Pd2(dba)3 (0.05mmol, 50mg) and sodium tert-butoxide (5mmol, 480mg) and tert-butylphosphine (5mmol, 450mg), then add 40mL of redistilled toluene, pass nitrogen, use vacuum pump to evacuate and ventilate for 15 minutes, cover the reaction bottle with tin foil to avoid light, stir and heat to 110℃ for 24h, stop the reaction, cool to room temperature, extract the reaction solution, use dichloromethane (1000mL) and water (250mL) to wash repeatedly 3 to 4 times, and dry the organic phase with anhydrous magnesium sulfate to collect the filtrate, use column chromatography for rough separation, the developing agent is petroleum ether: dichloromethane: acetone (volume ratio is 25:2:1), and obtain organic compound M3-2, 635mg of white solid, with a yield of 73%. The melting point is 235.1~236.3℃. The NMR data are as follows: 1H NMR (500 MHz, Chloroform-d) δ 8.15–8.10 (m, 2H), 7.57 (m, J = 8.1, 7.2, 1.3 Hz, 1H), 7.40–7.37 (m, 3H), 7.32–7.26 (m, 3H), 7.22–7.19 (m, 1H), 7.19–7.18 (m, 1H), 7.17–7.13 (m, 4H), 4.15 (t, J = 6.3 Hz, 2H), 4.10 (t, J = 6.2 Hz, 2H), 4.07 (t, J = 6.2 Hz, 2H), 1.73–1.65 (m, 6H), 1.40–1.26 (m, 18H), 0.91–0.88 (m, 9H).

[0354] Embodiment 27:

[0355] Preparation of organic compound M3-3:

[0356]

[0357] Compound 1-6 (1 mmol, 751 mg), 9,9-dimethyl-9,10-dihydroacridine (1.5 mmol, 316.5 mg), diphenylamine (1.5 mmol, 253.5 mg), Pd2(dba)3 (0.05 mmol, 50 mg), sodium tert-butoxide (5 mmol, 480 mg) and tert-butylphosphine (5 mmol, 450 mg) were added to a 100 mL two-necked bottle, and then 40 mL of redistilled toluene was added, nitrogen was introduced, and a vacuum pump was used to evacuate the mixture. The mixture was ventilated for 15 minutes, the reaction bottle was protected from light by tin foil, stirred and heated to 110°C for 24 hours, the reaction was stopped, and the temperature was cooled to room temperature. The reaction solution was extracted and washed repeatedly with dichloromethane (1000 mL) and water (250 mL) for 3 to 4 times, and the organic phase was dried over anhydrous magnesium sulfate. The filtrate was collected and crudely separated by column chromatography. The developing agent was petroleum ether: dichloromethane: acetone (volume ratio of 25:2:1). The organic compound M3-3 was 681 mg of a white solid with a yield of 65%. The NMR data are as follows: 1H NMR (500 MHz, Chloroform-d) δ 8.14–8.12 (m, 1H), 7.98–7.96 (m, 1H), 7.28–7.23 (m, 9H), 7.22–7.19 (m, 1H), 7.19–7.15 (m, 4H), 7.14–7.09 (m, 5H), 7.05–7.01 (m, 3H), 4.17 (t, J=6.3 Hz, 2H), 4.12–4.09 (m, 4H), 1.73–1.64 (m, 6H), 1.53 (s, 6H), 1.40–1.26 (m, 18H), 0.91–0.88 (m, 9H).

[0358] Embodiment 28:

[0359] Preparation of organic compound M3-4:

[0360]

[0361] Compound 1-6 (1 mmol, 751 mg), methoxytriphenylamine boric acid (1.5 mmol, 526.7 mg), 9,9-di(4-methoxyphenyl)-9,10-dihydroacridine (1.5 mmol, 590.4 mg), Pd2(dba)3 (0.05 mmol, 50 mg), sodium tert-butoxide (5 mmol, 480 mg) and tert-butylphosphine (5 mmol, 450 mg) were added to a 100 mL two-necked bottle, and then 40 mL of redistilled toluene was added and nitrogen was introduced to allow the mixture to react. Use a vacuum pump to evacuate and ventilate for 15 minutes, protect the reaction bottle from light with tin foil, stir and heat to 110°C for 24 hours, stop the reaction, and cool to room temperature. Extract the reaction solution, use dichloromethane (1000mL) and water (250mL) to wash repeatedly 3 to 4 times, and dry the organic phase with anhydrous magnesium sulfate. Collect the filtrate and use column chromatography for crude separation. The developing solvent is petroleum ether: dichloromethane: acetone (volume ratio is 25:2:1). The organic compound M3-4 is 834 mg of white solid, and the yield is 61%. The NMR data are as follows: 1HNMR (500MHz, Chloroform-d) δ8.17–8.13 (m, 2H), 7.66–7.65 (m, 1H), 7.52–7.49 (m, 3H), 7.32–7.29 (m, 1H), 7.27–7.24 (m, 2H), 7.15–7.12 (m, 3H), 7.11–7.08 (m, 2H), 7. 05–7.00(m,10H),6.95–6.93(m,2H),6.89–6.82(m,8H),4.15(t,J=6.3Hz,2H),4.10(s,4 H),3.78(s,6H),3.76(s,6H),1.73–1.65(m,6H),1.40–1.26(m,18H),0.91–0.88(m,9H).

[0362] Comparative Example 1:

[0363] Preparation of organic compound P1:

[0364]

[0365] Compound M1-4 (1 mmol, 609 mg) was added to a 100 mL two-necked bottle and dissolved in 40 mL chloroform. N-bromosuccinimide (NBS) (3 mmol, 534 mg) was dissolved in 10 mL chloroform and 40 mL chloroform. The mixture was stirred for 3 h in an ice bath. The reaction was stopped when the raw materials were 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 20:1) to obtain the intermediate crude product P1-1. Compound P1-1 (1 mmol, 765 mg), 9H-carbazole (3 mmol, 501 mg), Pd2 (dba )3 (0.05mmol, 50mg) and sodium tert-butoxide (5mmol, 480mg) and tert-butylphosphine (5mmol, 450mg), then add 40mL of redistilled toluene, pass nitrogen, use a vacuum pump to evacuate and replace with nitrogen for 15 minutes, cover the reaction bottle with tin foil to avoid light, stir and heat to 110℃ for 24h, stop the reaction, and cool to room temperature, extract the reaction solution, use dichloromethane (1000mL) and water (250mL) to wash repeatedly 3 to 4 times, and the organic phase is dried with anhydrous magnesium sulfate, and crude separation is performed by column chromatography, the developing agent is petroleum ether: dichloromethane: acetone (volume ratio is 25:2:1), and the organic compound P1 is obtained as a white solid of 676mg, with a yield of 72%. The NMR data are as follows: 1H NMR (500 MHz, Chloroform-d) δ 8.16–8.13 (m, 4H), 7.98–7.95 (m, 2H), 7.62–7.58 (m, 4H), 7.36–7.30 (m, 6H), 7.29–7.28 (m, 2H), 7.26–7.22 (m, 2H), 7.14–7.10 (m, 2H), 4.04 (t, J=6.3 Hz, 6H), 1.79–1.72 (m, 6H), 1.47–1.40 (m, 6H), 1.34–1.26 (m, 12H), 0.91–0.88 (m, 9H).

[0366] Device Example 1

[0367] The device embodiment provides a quantum dot light emitting diode and a method for preparing the same, which specifically includes the following steps.

[0368] 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;

[0369] Step 2: Spin-coat the cleaned ITO glass sheet with PEDOT:PSS (thickness of about 25 nm) in air at a speed of 5000 r / min for 30 seconds; after spin coating, place it in air for annealing at 150°C for 30 minutes to obtain a hole injection layer with a thickness of 40 nm;

[0370] 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;

[0371] 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;

[0372] Step 5: Spin the organic compound M1-1 (30 mg / mL) in 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 an electron transport layer;

[0373] 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.

[0374] The device structure is: ITO / PEDOT:PPS (40nm) / TFB (8wt%) / QD (30nm) / M1 (1nm) / Ag (20nm).

[0375] Device Examples 2-28

[0376] Device Example 2-28 is substantially the same as Device Example 1, except that in step 5, organic compounds M1-2 to M1-4, organic compounds M2-1 to M2-20, and organic compounds M3-1 to M3-4 of Example 2-28 are used respectively.

[0377] Device Comparison Example 1

[0378] This device embodiment is basically the same as device embodiment 1, and the only difference is that zinc oxide is used to prepare the electron transport layer in step 5.

[0379] Device Comparison Example 2

[0380] This device example is substantially the same as device example 1, except that the organic compound P1 of comparative example 1 is used in step 5.

[0381] Test 1:

[0382] The quantum dot light-emitting diodes of device examples 1-28 and device comparative examples 1-2 were tested for photoelectric efficiency and working life, and the data are shown in Tables 1 and 2. Specific test items include maximum current efficiency C.Emax, turn-on voltage, maximum external quantum efficiency EQEmax, chromaticity coordinates, lifespan T95@1000nit, etc.

[0383] The test method for the lifespan T95@1000nit is: the time required for the device to reduce its brightness to a certain percentage of the maximum brightness under constant current or voltage drive. The time when the brightness drops to 95% of the maximum brightness is defined as T95, and this lifespan is the measured lifespan. In order to shorten the test cycle, the device lifespan test is usually carried out at high brightness by accelerating device aging, and the lifespan at high brightness is obtained by fitting the extended exponential decay brightness attenuation fitting formula. For example, the lifespan at 1000nit is calculated as T95@1000nit. The specific calculation formula is as follows:

[0384]

[0385] 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.

[0386] Table 1

[0387] <![CDATA[Chromaticity coordinates (CIE x , CIE y )]]> Device Example 25 (0.235,0.746) Device Example 26 (0.230,0.750) Device Example 27 (0.219,0.758) Device Example 28 (0.210,0.764) Device Comparison Example 1 (0.213,0.762) Device Comparison Example 2 (0.210,0.764)

[0388] Table 2

[0389]

[0390]

[0391] From Tables 1 and 2, we can see that:

[0392] The organic compound provided in the present application is used as a material for the organic electron transport layer. Compared with the comparative example 1 in which zinc oxide is used as a material for the inorganic electron transport layer, the organic compound has good electroluminescent efficiency and effectively improves the photoelectric performance and life of the QLED device.

[0393] The organic compound provided in the present application is used as a material for an organic electron transport layer. Compared with the material for the electron transport layer using the organic compound P1 in Comparative Example 2, the organic compound has good electroluminescent efficiency and effectively improves the photoelectric performance and life of the QLED device.

[0394] The organic compounds and preparation methods thereof, 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 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 Phenylalkyl, substituted or unsubstituted C7~C 36 One or more of phenylalkoxy; Ar1 and Ar2 are each independently selected from the following structures: *-D2； Wherein, D1, D3, D4, and D5 are selected from substituted or unsubstituted aryl groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaryl groups having 5 to 60 ring atoms, or a combination thereof; D2 is selected from H, D, a substituted or unsubstituted aryl group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, or a combination thereof; n1 and n2 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 D1 and D3 are selected from one of the following substituted or unsubstituted structures: Among them, each Z 1 Each independently selected from C or N, Z 2 Selected from C, N, O, Si or S.

4. The organic compound according to claim 3, characterized in that D1 and D3 are selected from one of the following substituted or unsubstituted structures: wherein R4 and R5 are each independently selected from substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C7-C 12 One or more of the phenylalkyl groups, m1 is selected from any integer in the range of 0 to 8, m2 is selected from any integer in the range of 0 to 10, m3 is selected from any integer in the range of 0 to 7, and m4 is selected from any integer in the range of 0 to 6.

5. The organic compound according to claim 4, characterized in that D1 and D3 are selected from any one of Formulas 1-1 to 1-31:

6. The organic compound according to claim 1 or 2, characterized in that R1, R2, and R3 are selected from substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1~C 12 Alkoxy, substituted or unsubstituted C7~C 18 Phenylalkyl, substituted or unsubstituted C7~C 18 Any one of phenylalkoxy; and / or D4 and D5 are independently selected from substituted or unsubstituted benzene, anthracene, naphthalene or biphenyl; and / or D2 is selected from any one of formulas 2-1 to 2-33:

7. The organic compound according to claim 1, 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: Prepared by the following synthetic route: or Wherein, the organic compound is M1 or M2, R1, R2, and R3 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted phenylalkyl, substituted or unsubstituted C7~C 36 One or more of phenylalkoxy; Ar1 and Ar2 are each independently selected from the following structures: *-D2； Wherein, D1, D2, D3, D4, and D5 are selected from substituted or unsubstituted aryl groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaryl groups having 5 to 60 ring atoms, or a combination thereof; n1 and n2 are each independently selected from integers of 0-4.

9. The preparation method according to claim 8, characterized in that: The preparation method comprises: Under inert gas protection conditions, compound 1 is mixed with a first halogenated hydrocarbon under alkaline conditions to react to generate compound 2; Under inert gas protection conditions, compound 2 is first mixed with a first halogenating agent for reaction, and then mixed with o-nitrophenylboric acid for reaction under palladium catalyst conditions to generate compound 3; Under inert gas protection conditions, the compound 3, triethyl phosphite and o-dichlorobenzene are mixed and reacted to generate compound 4; The compound 4 is mixed with a second halogenated hydrocarbon under alkaline conditions to react to generate a compound 5; The compound 5 is mixed with an oxidant to react to generate a compound M1; Wherein, the compound M1 is the organic compound, or the preparation method of the organic compound further comprises: The compound M1 is first mixed with a second halogenating agent for reaction, and then mixed with an aromatic compound for reaction under palladium catalyst conditions to generate a compound M2, wherein M2 is the organic compound.

10. The preparation method according to claim 9, characterized in that: The molar ratio of the compound 1 to the first halogenated hydrocarbon is 1:(1-2); and / or In the process of mixing compound 1 with the first halogenated hydrocarbon under alkaline conditions to generate compound 2 under inert gas protection conditions, the reaction temperature is 80-110° C.; and / or In the process of mixing compound 1 with the first halogenated hydrocarbon under alkaline conditions to generate compound 2 under inert gas protection conditions, the reaction time is 6 to 24 hours; and / or The molar ratio of the compound 2 to the first halogenating agent is 1:(2-4); and / or The molar ratio of the compound 2 to the o-nitrobenzeneboric acid is 1:(2-4); and / or In the process of mixing compound 2 with a first halogenating agent under inert gas protection and then mixing with o-nitrophenylboric acid under palladium catalyst to generate compound 3, the reaction temperature is 80-110° C.; and / or In the process of first mixing compound 2 with a first halogenating agent under inert gas protection conditions and then mixing compound 2 with o-nitrophenylboric acid under palladium catalyst conditions to generate compound 3, the reaction time is 12 to 24 hours; and / or The molar ratio of the compound 3 to the triethyl phosphite is 1:(40-60); and / or In the process of mixing the compound 3, triethyl phosphite and o-dichlorobenzene to generate the compound 4 under the protection of inert gas, the reaction temperature is 140-170° C.; and / or In the process of mixing the compound 3, triethyl phosphite and o-dichlorobenzene to generate the compound 4 under the protection of inert gas, the reaction time is 12 to 24 hours; and / or The molar ratio of the compound 4 to the second halogenated hydrocarbon is 1:(2-4); and / or In the process of mixing the compound 4 with the second halogenated hydrocarbon under alkaline conditions to generate the compound 5, the reaction temperature is 80-110° C.; and / or In the process of mixing the compound 4 with the second halogenated hydrocarbon under alkaline conditions to generate the compound 5, the reaction time is 6 to 24 hours; and / or The molar ratio of the compound 5 to the oxidant is 1:(40-80); and / or In the process of mixing the compound 5 with an oxidant to generate the compound M1, the reaction temperature is 40 to 60° C.; and / or In the process of mixing the compound 5 with an oxidant to generate the compound M1, the reaction time is 12 to 24 hours; and / or The molar ratio of the compound M1 to the second halogenating agent is 1:(2-4); and / or The molar ratio of the compound M1 to the aromatic compound is 1:(2-4); and / or In the process of first mixing the compound M1 with the second halogenating agent and then mixing with the aromatic compound under the condition of a palladium catalyst to generate the compound M2, the reaction temperature is 80-110° C.; and / or The compound M1 is first mixed with a second halogenating agent for reaction, and then mixed with an aromatic compound under palladium catalyst conditions to generate a compound M2, wherein M2 is the organic compound, and the reaction time is 12 to 24 hours.

11. 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 10.

12. An electronic device, characterized in that: The organic compound comprises the organic compound according to any one of claims 1 to 7, or the organic compound prepared by the method for preparing the organic compound according to any one of claims 8 to 10, or the electron transport material according to claim 11.

13. The electronic device according to claim 12, characterized in that The electronic device is an organic electroluminescent device, a quantum dot electroluminescent device, an organic photovoltaic cell, an organic field effect transistor, an organic light-emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor, or an organic plasma laser emitting diode.

14. The electronic device according to claim 12, wherein: The electronic device comprises an electronic functional layer, wherein the electronic functional layer comprises the organic compound according to any one of claims 1 to 7, or comprises an organic compound prepared by the method for preparing an organic compound according to any one of claims 8 to 10, or comprises the electron transport material according to claim 11.

15. The electronic device according to claim 12, wherein: The electronic device is a photoelectric device, and the photoelectric device comprises: A first electrode and a second electrode arranged opposite to each other; An electronic functional layer, disposed between the first electrode and the second electrode; The material of the electronic functional layer includes the organic compound described in any one of claims 1 to 7, or includes the organic compound prepared by the method for preparing the organic compound described in any one of claims 8 to 10, or includes the electron transport material described in claim 11.

16. The electronic device according to claim 15, characterized in that The optoelectronic device comprises a light-emitting layer, wherein the light-emitting layer is arranged between the first electrode and the electronic functional layer or the light-emitting layer is arranged between the second electrode 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 group The compound is at least one of a group IV-VI compound, a group III-V compound and a group I-III-VI compound, wherein the group II-VI compound is selected from 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, CdHgS 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, SnPbSTe, and the III-V group compound is selected from at least one of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, Ga at least one of aNP, 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, and the Group I-III-VI compound is selected from 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; And / or, the first electrode and the second electrode 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, ITZO, 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.

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