Boron-nitrogen organic compound, preparation method and application thereof, composition and photoelectric device

Abstract

The invention discloses a boron-nitrogen organic compound as well as a preparation method and application thereof, a composition and a photoelectric device. The boron-nitrogen organic compound has a structure as shown in a formula (I): # imgabs0 #. The boron-nitrogen organic compound disclosed by the invention has relatively narrow half-peak width of an emission peak.

Description

Technical Field

[0001] The present application relates to the technical field of organic materials, and in particular to a boron-nitrogen organic compound and a preparation method and application, a composition, and a photoelectric device thereof. Background Art

[0002] Organic light-emitting materials refer to organic compounds or polymers that can emit visible light after absorbing energy. These materials are widely used in optoelectronic devices, fluorescent labels, display technology and other fields.

[0003] Guest materials play an important role in organic light-emitting materials. They can optimize the performance of light-emitting materials by adjusting the luminescence performance, lattice structure, carrier transport and energy level alignment. Boron-nitrogen organic compounds are commonly used guest materials.

[0004] However, the emission peak half-width of existing boron-nitrogen organic compounds is relatively wide. Summary of the invention

[0005] In view of this, the present application provides a boron-nitrogen organic compound and its preparation method and application, composition, and optoelectronic device.

[0006] In a first aspect, an embodiment of the present application provides a boron-nitrogen organic compound having a structure shown in formula (I):

[0007]

[0008] Wherein, n1 is independently any integer from 1 to 2 each time it appears, and n2 is independently any integer from 1 to 3 each time it appears;

[0009] L1 and L2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaryl group having 6 to 60 ring atoms, or a combination of these groups;

[0010] R1 and R2 are each independently selected from hydrogen, deuterium, cyano, isocyano, -Cl, -Br, -F, -I, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C1~C 20 Alkoxy, substituted or unsubstituted C1~C 20 Alkylthio, substituted or unsubstituted C1~C 20 Alkylcarbonyl, substituted or unsubstituted C1~C 20 alkoxycarbonyl, substituted or unsubstituted aryloxy having 6 to 30 ring atoms, substituted or unsubstituted aryloxycarbonyl having 6 to 30 ring atoms, substituted or unsubstituted C2 to C 20alkenyl, substituted or unsubstituted aryl having 6 to 60 ring atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, substituted or unsubstituted heteroaryloxy having 5 to 30 ring atoms, or a combination of these groups;

[0011] When substituted with a substituent, each occurrence of the substituent is independently selected from deuterium, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C 20 Alkyl, C1~C 30 A combination of one or more of an alkoxy group and an aryl group having 6 to 30 ring atoms.

[0012] In a second aspect, the present invention also provides a method for preparing a boron-nitrogen organic compound, comprising the following steps:

[0013] Mixing the first compound with a first halogenating agent to perform a first halogenation reaction to obtain a second compound;

[0014] subjecting the second compound to a coupling reaction to obtain a third compound;

[0015] mixing the third compound with the second halogenating agent to perform a first halogenation reaction to obtain a fourth compound; and

[0016] Under the conditions of lithium salt, boron halide, organic amine and Grignard reagent, the fourth compound is subjected to lithiation-boration-Grignard reaction through a one-pot method to obtain a boron-nitrogen organic compound.

[0017] In a third aspect, the embodiments of the present application also provide an application of the boron-nitrogen organic compound in the optoelectronic field.

[0018] In a fourth aspect, an embodiment of the present application further provides a composition, comprising a host material and a guest material, wherein the guest material is the boron-nitrogen organic compound.

[0019] In a fifth aspect, an embodiment of the present application also provides a photoelectric device, comprising the boron-nitrogen organic compound.

[0020] The boron-nitrogen organic compound described in the present application has a narrow emission peak half-width. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] 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 paying any creative work.

[0022] Figure 1 This is a flow chart of a method for preparing a boron-nitrogen organic compound provided in an embodiment of the present application;

[0023] Figure 2 is a schematic structural diagram of a photoelectric device provided in an embodiment of the present application;

[0024] Figure 3 It is a schematic diagram of the structure of another optoelectronic device provided in an embodiment of the present application.

[0025] Reference numerals:

[0026] Photoelectric device 100; anode 10; light-emitting layer 20; cathode 30; electron transport layer 40; hole transport layer 50; hole injection layer 60; electron injection layer 70. DETAILED DESCRIPTION

[0027] The technical solutions in the embodiments of the present application will be clearly and completely described below in conjunction with the drawings in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, rather than all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without making 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.

[0028] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those generally understood by those skilled in the art of the present invention. The terms used herein in the specification of the present invention are only for the purpose of describing specific embodiments and are not intended to limit the present invention. The term "and / or" used herein includes any and all combinations of one or more related listed items.

[0029] In this application, unless otherwise stated, directional words such as "upper" and "lower" generally refer to the upper and lower parts of the device in actual use or working state, specifically the drawing direction in the accompanying drawings; while "inner" and "outer" refer to the outline of the device. In addition, in the description of this application, the term "including" means "including but not limited to". The terms first, second, third, etc. are used only as labels and do not impose numerical requirements or establish an order.

[0030] 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.

[0031] 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.

[0032] In the present application, when a layer is formed "on" another layer, the so-called "on" is a broad concept, which may mean that the formed another layer is adjacent to the certain layer, or that there are other spacing structural layers between the another layer and the certain layer. For example, when a cathode is formed "on" the first carrier functional layer, the so-called "on" may mean that the formed cathode is adjacent to the first carrier functional layer, or that there are other spacing structural layers between the cathode and the first carrier functional layer, such as a light-emitting layer.

[0033] Various embodiments of the present application may be presented in the form of a range; it should be understood that the description in the form of a range is only for convenience and brevity, and should not be understood as a rigid limitation on the scope of the present application; therefore, the range description should be considered to have specifically disclosed all possible sub-ranges and single numerical values ​​within the range. For example, the range description 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 range, such as 1, 2, 3, 4, 5 and 6, which apply regardless of the range. In addition, whenever a numerical range is indicated herein, it is meant to include any cited number (fractional or integer) within the indicated range.

[0034] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0035] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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).

[0041] In the present application, * indicates a ligatable site.

[0042] 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. R1 can be connected to any substitutable position in the benzene ring.

[0043] 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.

[0044] At present, after years of development, organic electroluminescent technology has entered the stage of commercial popularization, but blue light OLED still has many problems, such as poor device stability, poor performance, and especially the problem of short service life.

[0045] The technical solution of this application is as follows:

[0046] In a first aspect, an embodiment of the present application provides a boron-nitrogen organic compound, wherein the boron-nitrogen organic compound has a structure shown in formula (I):

[0047]

[0048] Wherein, n1 is independently any integer from 1 to 2 each time it appears, and n2 is independently any integer from 1 to 3 each time it appears;

[0049] L1 and L2 are each independently selected from but not limited to substituted or unsubstituted aryl groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaryl groups having 6 to 60 ring atoms, or combinations thereof;

[0050] R1 and R2 are each independently selected from hydrogen, deuterium, cyano, isocyano, -Cl, -Br, -F, -I, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C1~C 20 Alkoxy, substituted or unsubstituted C1~C 20 Alkylthio, substituted or unsubstituted C1~C 20 Alkylcarbonyl, substituted or unsubstituted C1~C 20 alkoxycarbonyl, substituted or unsubstituted aryloxy having 6 to 30 ring atoms, substituted or unsubstituted aryloxycarbonyl having 6 to 30 ring atoms, substituted or unsubstituted C2 to C 20 Alkenyl, substituted or unsubstituted aryl having 6 to 60 ring atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, substituted or unsubstituted heteroaryloxy having 5 to 30 ring atoms, or a combination of these groups.

[0051] It should be noted that, in some embodiments, when the above groups are substituted by substituents, each occurrence of the substituents is independently selected from deuterium, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C 20 Alkyl, C1~C 30 A combination of one or more of an alkoxy group and an aryl group having 6 to 30 ring atoms.

[0052] It should be noted that, in some embodiments, when the above groups are substituted by substituents, each occurrence of the substituents is independently selected from deuterium, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C 15 Alkyl, C1~C 15 A combination of one or more of an alkoxy group and an aryl group having 6 to 15 ring atoms.

[0053] It should be noted that, in some embodiments, when the above groups are substituted by substituents, each occurrence of the substituents is independently selected from deuterium, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C 10 Alkyl, C1~C 10 One or more of an alkoxy group and an aryl group having 6 to 10 ring atoms.

[0054] It should be noted that the heteroatom of the heteroaryl group in the present application is selected from one or more of O, N, S, P, and Si.

[0055] In some embodiments, L1 and L2 are each independently selected from but not limited to, a substituted or unsubstituted aryl group having 6 to 40 ring atoms, a substituted or unsubstituted heteroaryl group having 6 to 40 ring atoms, or a combination of these groups.

[0056] In some embodiments, L1 and L2 are each independently selected from but not limited to, a substituted or unsubstituted aryl group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, or a combination of these groups.

[0057] In some embodiments, L1 and L2 are each independently selected from but not limited to, a substituted or unsubstituted aryl group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryl group having 6 to 20 ring atoms, or a combination of these groups.

[0058] In some embodiments, L1 and L2 are each independently selected from but not limited to, a substituted or unsubstituted aryl group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryl group having 6 to 10 ring atoms, or a combination of these groups.

[0059] In some embodiments, each occurrence of R1 and R2 is independently selected from, but not limited to, hydrogen, deuterium, cyano, isocyano, -Cl, -Br, -F, -I, substituted or unsubstituted C1-C 18 Alkyl, substituted or unsubstituted C1~C 18 Alkoxy, substituted or unsubstituted C1~C 18 Alkylthio, substituted or unsubstituted C1~C 18 Alkylcarbonyl, substituted or unsubstituted C1~C 18alkoxycarbonyl, substituted or unsubstituted aryloxy having 6 to 20 ring atoms, substituted or unsubstituted aryloxycarbonyl having 6 to 20 ring atoms, substituted or unsubstituted C2 to C 18 Alkenyl, substituted or unsubstituted aryl having 6 to 50 ring atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, substituted or unsubstituted heteroaryloxy having 5 to 30 ring atoms, or a combination of these groups.

[0060] In some embodiments, each occurrence of R1 and R2 is independently selected from, but not limited to, hydrogen, deuterium, cyano, isocyano, -Cl, -Br, -F, -I, substituted or unsubstituted C1-C 15 Alkyl, substituted or unsubstituted C1~C 15 Alkoxy, substituted or unsubstituted C1~C 15 Alkylthio, substituted or unsubstituted C1~C 15 Alkylcarbonyl, substituted or unsubstituted C1~C 15 alkoxycarbonyl, substituted or unsubstituted aryloxy having 7 to 15 ring atoms, substituted or unsubstituted aryloxycarbonyl having 6 to 15 ring atoms, substituted or unsubstituted C2 to C 15 Alkenyl, substituted or unsubstituted aryl having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, substituted or unsubstituted heteroaryloxy having 5 to 30 ring atoms, or a combination of these groups, or a combination of these groups.

[0061] In some embodiments, each occurrence of R1 and R2 is independently selected from, but not limited to, hydrogen, deuterium, cyano, isocyano, -Cl, -Br, -F, -I, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Alkylthio, substituted or unsubstituted C1~C 10 Alkylcarbonyl, substituted or unsubstituted C1~C 10 alkoxycarbonyl, substituted or unsubstituted aryloxy having 7 to 10 ring atoms, substituted or unsubstituted aryloxycarbonyl having 6 to 15 ring atoms, substituted or unsubstituted C2 to C 10 Alkenyl, substituted or unsubstituted aryl having 6 to 20 ring atoms, substituted or unsubstituted heteroaryl having 5 to 20 ring atoms, substituted or unsubstituted heteroaryloxy having 5 to 20 ring atoms, or a combination of these groups.

[0062] In some embodiments, each occurrence of R1 and R2 is independently selected from but not limited to hydrogen, deuterium, cyano, isocyano, -Cl, -Br, -F, -I, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C1-C8 alkoxy, substituted or unsubstituted C1-C8 alkylthio, substituted or unsubstituted C1-C8 alkylcarbonyl, substituted or unsubstituted C1-C8 alkoxycarbonyl, substituted or unsubstituted aryloxy having 7-10 ring atoms, substituted or unsubstituted aryloxycarbonyl having 6-10 ring atoms, substituted or unsubstituted C2-C8 alkenyl, substituted or unsubstituted aryl having 6-10 ring atoms, substituted or unsubstituted heteroaryl having 5-10 ring atoms, substituted or unsubstituted heteroaryloxy having 5-10 ring atoms, or a combination of these groups.

[0063] In some embodiments, each occurrence of R1 and R2 is independently selected from, but not limited to, hydrogen, deuterium, cyano, isocyano, -Cl, -Br, -F, -I, substituted or unsubstituted C1-C 15 Straight chain alkyl, substituted or unsubstituted C1~C 15 Straight chain alkoxy, substituted or unsubstituted C1~C 15 Straight chain alkylthio, substituted or unsubstituted C3~C 15 Branched alkyl, substituted or unsubstituted C3~C 15 Branched alkoxy, substituted or unsubstituted C3~C 15 Branched alkylthio, substituted or unsubstituted C3~C 15 Cyclic alkyl, substituted or unsubstituted C3~C 15 Cyclic alkoxy, substituted or unsubstituted C3~C 15 Cyclic alkylthio, substituted or unsubstituted C1~C 15 Alkylcarbonyl, substituted or unsubstituted C1~C 15 alkoxycarbonyl, substituted or unsubstituted aryloxy having 6 to 15 ring atoms, substituted or unsubstituted aryloxycarbonyl having 7 to 15 ring atoms, substituted or unsubstituted C2 to C 15 Alkenyl, substituted or unsubstituted aryl having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, substituted or unsubstituted heteroaryloxy having 5 to 30 ring atoms, or a combination of these groups.

[0064] In some embodiments, each occurrence of R1 and R2 is independently selected from, but not limited to, hydrogen, deuterium, cyano, -Cl, -Br, -F, -I, substituted or unsubstituted C1-C 10 Straight chain alkyl, substituted or unsubstituted C1~C 10 Straight chain alkoxy, substituted or unsubstituted C1~C 10 Straight chain alkylthio, substituted or unsubstituted C3~C 10Branched alkyl, substituted or unsubstituted C3~C 10 Branched alkoxy, substituted or unsubstituted C3~C 10 Branched alkylthio, substituted or unsubstituted C3~C 10 Cyclic alkyl, substituted or unsubstituted C3~C 10 Cyclic alkoxy, substituted or unsubstituted C3~C 10 Cyclic alkylthio, substituted or unsubstituted C1~C 10 Alkylcarbonyl, substituted or unsubstituted C1~C 10 alkoxycarbonyl, substituted or unsubstituted aryloxy having 6 to 10 ring atoms, substituted or unsubstituted aryloxycarbonyl having 7 to 10 ring atoms, substituted or unsubstituted C2 to C 10 Alkenyl, substituted or unsubstituted aryl having 6 to 20 ring atoms, substituted or unsubstituted heteroaryl having 5 to 20 ring atoms, substituted or unsubstituted heteroaryloxy having 5 to 20 ring atoms, or a combination of these groups.

[0065] In some embodiments, L1 and L2 are each independently selected from but not limited to any one of the following groups:

[0066]

[0067]

[0068] Wherein, m1 is any integer from 0 to 5, m2 is any integer from 0 to 3, m3 is any integer from 0 to 9, m4 and m5 are each independently any integer from 0 to 7, m6, m7, and m8 are each independently any integer from 0 to 4, and m6, m7, and m8 are not 4 at the same time;

[0069] Each occurrence of M is independently selected from O, S, CR 11 R 12 or NR 13 ;

[0070] M' is selected from N or phenyl;

[0071] L3 is selected from a single bond or is absent;

[0072] R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 Each occurrence is independently selected from halogen, cyano, substituted or unsubstituted C1-C 20 Straight chain alkyl, substituted or unsubstituted C3~C 20 Branched alkyl, substituted or unsubstituted C1~C 20 Straight chain alkoxy, substituted or unsubstituted C3~C20 branched alkoxy, or a combination of these groups.

[0073] In some embodiments, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 Each occurrence is independently selected from halogen, cyano, substituted or unsubstituted C1-C 15 Straight chain alkyl, substituted or unsubstituted C3~C 15 Branched alkyl, substituted or unsubstituted C1~C 15 Straight chain alkoxy, substituted or unsubstituted C3~C 15 branched alkoxy, or a combination of these groups.

[0074] In some embodiments, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 Each occurrence is independently selected from halogen, cyano, substituted or unsubstituted C1-C 10 Straight chain alkyl, substituted or unsubstituted C3~C 10 Branched alkyl, substituted or unsubstituted C1~C 10 Straight chain alkoxy, substituted or unsubstituted C3~C 10 branched alkoxy, or a combination of these groups.

[0075] In some embodiments, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 Each occurrence is independently selected from halogen, cyano, substituted or unsubstituted C1-C8 straight chain alkyl, substituted or unsubstituted C3-C8 branched chain alkyl, substituted or unsubstituted C1-C8 straight chain alkoxy, substituted or unsubstituted C3-C8 branched chain alkoxy, or a combination of these groups.

[0076] As an example, in some embodiments, L1 and L2 are each independently selected from but not limited to any one of the following groups:

[0077]

[0078] It should be noted that: represents the connection site, "Throughout a benzene ring" means that B in formula (I) can be connected to any connectable site on the benzene ring. Penetrating two benzene rings means that B in formula (I) can be connected to any connectable site on the two benzene rings.

[0079] As an example, the boron-nitrogen organic compound may be selected from but not limited to any one of the compounds represented by Formula M1 to Formula M24:

[0080]

[0081]

[0082] The boron nitrogen organic compound described in the present application has an aromatic amine heteroatom fused ring structure. The heavy atom Se is introduced into the fused ring structure, which can enhance the spin coupling between S1 (ground state singlet) and T1 (excited triplet), improve the reverse intersystem transition rate, and improve the triplet utilization rate, thereby increasing the PLQY of the boron nitrogen organic compound, so that the singlet exciton can quickly realize the radiative transition, avoid the exciton transfer process, the high-energy state exciton accumulation causes the luminescent material to decompose, thereby avoiding the triplet annihilation of the boron nitrogen organic compound in the luminescent layer, and improving the device stability. Further, the boron nitrogen organic compound has a narrower emission peak half-peak width, and when it is used for the luminescent layer of an optoelectronic device, the luminous efficiency of the optoelectronic device can be effectively improved. In addition, the boron nitrogen organic compound described in the present application has a deeper LUMO energy level, which can effectively avoid the formation of electron traps in the boron nitrogen organic compound, and improve the device stability and efficiency.

[0083] In a second aspect, the present application also provides a method for preparing a boron-nitrogen organic compound, wherein the synthesis route of the boron-nitrogen organic compound is as follows:

[0084]

[0085] In the above synthesis route, R1, R2, n1 and n2 are as described above and will not be described in detail here.

[0086] In the above synthesis route, X1 and X2 are independently selected from but not limited to one or more of F, Cl, Br and I each time they appear.

[0087] Please refer to Figure 1 , the preparation method of the boron-nitrogen organic compound comprises the following steps:

[0088] Step S11, mixing the first compound with a first halogenating agent, performing a first halogenation reaction, and obtaining a second compound;

[0089] Step S12, subjecting the second compound to a coupling reaction to obtain a third compound;

[0090] Step S13, mixing the third compound with the second halogenating agent, performing a first halogenation reaction, and obtaining a fourth compound;

[0091] Step S14, under the conditions of lithium salt, boron halide, organic amine and Grignard reagent, subjecting the fourth compound to lithiation-boration-Grignard reaction by a one-pot method to obtain a boron-nitrogen organic compound.

[0092] In the step S11:

[0093] The first compound includes, but is not limited to, one or more of 10H-phenoselenazines.

[0094] In some embodiments, the first halogenating agent includes but is not limited to N-halosuccinimide. Further, the N-halosuccinimide includes but is not limited to one or more of N-bromosuccinimide (NBS), N-iodosuccinimide (NCS), and N-iodosuccinimide.

[0095] In some embodiments, the molar ratio of the first compound to the first halogenating agent is 1:(1-1.5), for example, 1:1, 1:1.1, 1:1.15, 1:1.2, 1:1.25, 1:1.3, 1:1.35, 1:1.4, 1:1.45, 1:1.5, etc. Within the ratio range, the first halogenation reaction can be fully and effectively carried out.

[0096] In some embodiments, the temperature of the first halogenation reaction is 50-75°C, for example, 50°C, 52°C, 55°C, 57°C, 60°C, 63°C, 65°C, 68°C, 70°C, 72°C, 75°C, etc., and the time of the first halogenation reaction is 1-4h, for example, 1h, 1.5h, 2h, 2.5h, 3h, 3.5h, 4h, etc. Within the temperature and time range, it is beneficial for the first halogenation reaction to be fully and effectively carried out.

[0097] In step S12:

[0098] In some embodiments, the coupling reaction is carried out under an inert atmosphere. Further, the inert atmosphere includes, but is not limited to, one or more of nitrogen, helium, argon, neon, krypton, and xenon.

[0099] In some embodiments, a base and a catalyst are added during the coupling reaction, which is beneficial to the coupling reaction.

[0100] In some embodiments, the base includes but is not limited to one or more of potassium carbonate, potassium phosphate, and cesium carbonate.

[0101] In some embodiments, the catalyst includes, but is not limited to, one or more of cuprous iodide, cuprous bromide, and cuprous chloride.

[0102] In some embodiments, the molar ratio of the second compound to the base is 1:(1-2), for example, 1:1, 1:1.1, 1:1.2, 1:1.3, 1:1.4, 1:1.5, 1:1.6, 1:1.7, 1:1.8, 1:1.9, 1:2, etc.

[0103] In some embodiments, the molar ratio of the second compound to the catalyst is 1:(0.15-0.25), for example, 1:0.15, 1:0.16, 1:0.17, 1:0.18, 1:0.19, 1:0.2, 1:0.21, 1:0.22, 1:0.23, 1:0.24, 1:0.25, etc.

[0104] In some embodiments, a ligand is added during the coupling reaction to increase the yield.

[0105] In some embodiments, the ligand includes but is not limited to one or more of 18-crown-6 (18-crown-6) and 12-crown-4 (12-crown-4).

[0106] In some embodiments, the molar ratio of the second compound to the ligand is 1:(0.15-0.25), for example, 1:0.15, 1:0.16, 1:0.17, 1:0.18, 1:0.19, 1:0.2, 1:0.21, 1:0.22, 1:0.23, 1:0.24, 1:0.25, etc.

[0107] In some embodiments, the coupling reaction temperature is 160-190° C., for example, 160° C., 165° C., 170° C., 175° C., 180° C., 185° C., 190° C., and the time is 12-24 h, 12 h, 13 h, 15 h, 18 h, 20 h, 22 h, 24 h, etc. Within the temperature and time range, the coupling reaction is conducive to rapid, sufficient and effective progress.

[0108] In step S13:

[0109] In some embodiments, the second halogenating agent includes but is not limited to N-halosuccinimide. Further, the N-halosuccinimide includes but is not limited to one or more of N-bromosuccinimide (NBS), N-iodosuccinimide (NCS), and N-iodosuccinimide.

[0110] In some embodiments, the molar ratio of the third compound to the second halogenating agent is 1:(2-4.5), for example, 1:2, 1:2.3, 1:2.5, 1:2.6, 1:2.8, 1:3, 1:3.2, 1:3.4, 1:3.5, 1:3.6, 1:3.8, 1:4, 1:4.1, 1:4.3, 1:4.5, etc. Within the ratio range, the second halogenation reaction can be fully and effectively carried out.

[0111] In some embodiments, the temperature of the second halogenation reaction is 50-75°C, for example, 50°C, 52°C, 55°C, 57°C, 60°C, 63°C, 65°C, 68°C, 70°C, 72°C, 75°C, etc., and the time of the second halogenation reaction is 1-4h, for example, 1h, 1.5h, 2h, 2.5h, 3h, 3.5h, 4h, etc. Within the temperature and time range, it is beneficial for the first halogenation reaction to be fully and effectively carried out.

[0112] In step S14:

[0113] In some embodiments, the lithiation-boration-Grignard reaction is carried out in an inert atmosphere, and the inert atmosphere includes but is not limited to one or more of nitrogen, helium, argon, neon, krypton, and xenon.

[0114] In some embodiments, the lithium salt includes but is not limited to an organic lithium salt, and the organic lithium salt includes but is not limited to an alkyl lithium salt. The alkyl lithium salt includes but is not limited to one or more of n-butyl lithium and tert-butyl lithium.

[0115] In some embodiments, the boron halide includes, but is not limited to, one or more of boron tribromide and boron triiodide.

[0116] In some embodiments, the organic amine includes, but is not limited to, one or more of 1,2,2,6,6-pentamethylpiperidine and N,N-diisopropylethylamine. The organic amine promotes the ring-closing reaction during the reaction.

[0117] In some embodiments, the Grignard reagent includes but is not limited to organic magnesium bromide, and the organic magnesium bromide includes but is not limited to one or more of 4-tert-butylphenylmagnesium bromide (CAS: 63488-10-8), 4-diphenylmagnesium bromide (CAS: 3315-91-1), 2-naphthylmagnesium bromide (CAS: 21473-01-8), 2-trifluoromethylphenylmagnesium bromide (CAS: 395-47-1), 2-mesitylmagnesium bromide (CAS: 2633-66-1), p-phenylnitrilemagnesium bromide (CAS: 412044-48-5), 3-thienylmagnesium bromide (CAS: 106032-16-0), 2-furylmagnesium bromide (CAS: 98754-48-4), 3,5-diphenylmagnesium bromide (CAS: 34696-73-6), and 4-methylphenylmagnesium bromide (CAS: 4294-57-9).

[0118] In some embodiments, the molar ratio of the fourth compound to the lithium salt is 1:(2-6), for example, 1:2, 1:2.2, 1:2.3, 1:2.5, 1:2.6, 1:2.8, 1:3, 1:3.2, 1:3.3, 1:3.5, 1:3.6, 1:3.8, 1:4, 1:4.2, 1:4.5, 1:4.8, 1:5, 1:5.2, 1:5.3, 1:5.4, 1:5.5, etc. Within the range, it is beneficial for the lithiation reaction to be fully and effectively carried out.

[0119] In some embodiments, the molar ratio of the fourth compound to the boron halide is 1:(2-6.5), for example 1:2, 1:2.2, 1:2.3, 1:2.5, 1:2.6, 1:2.8, 1:3, 1:3.2, 1:3.3, 1:3.5, 1:3.6, 1:3.8, 1:4, 1:4.2, 1:4.5, 1:4.8, 1:5, 1:5.2, 1:5.3, 1:5.4, 1:5.5, 1:5.8, 1:6, 1:6.1, 1:6.3, 1:6.5, etc. Within the above range, the borylation reaction is conducive to being fully and effectively carried out.

[0120] In some embodiments, the molar ratio of the fourth compound to the organic amine is 1:(2-5), for example, 1:2, 1:2.2, 1:2.3, 1:2.5, 1:2.6, 1:2.8, 1:3, 1:3.2, 1:3.3, 1:3.5, 1:3.6, 1:3.8, 1:4, 1:4.2, 1:4.5, 1:4.8, 1:5, etc. Within the range...

[0121] In some embodiments, the molar ratio of the fourth compound to the Grignard reagent is 1:(2-10), for example, 1:2, 1:2.5, 1:3, 1:3.5, 1:4, 1:4.5, 1:5, 1:5.5, 1:6, 1:6.2, 1:6.5, 1:7, 1:7.5, 1:8, 1:8.25, 1:8.5, 1:9, 1:9.3, 1:9.5, 1:10, etc. Within the above range, the Grignard reaction is facilitated to proceed quickly and efficiently.

[0122] In some embodiments, the temperature of the lithiation reaction is -50 to 0°C, for example, -50°C, -45°C, -40°C, -35°C, -30°C, -25°C, -20°C, -15°C, -10°C, -5°C, 0°C, etc. Within the above range, the lithiation reaction is conducive to being fully and effectively carried out.

[0123] In some embodiments, the temperature of the borylation reaction is -50 to 120°C, for example, -50°C, -45°C, -40°C, -35°C, -30°C, -25°C, -20°C, -15°C, -10°C, -5°C, 0°C, 10°C, 20°C, 30°C, 40°C, 50°C, 60°C, 70°C, 80°C, 90°C, 100°C, 110°C, 120°C, etc. Within the above range, the borylation reaction is conducive to being fully and effectively carried out.

[0124] In some embodiments, the temperature of the Grignard reaction is 10-50° C., for example, 10° C., 15° C., 20° C., 25° C., 30° C., 35° C., 40° C., 45° C., 50° C., etc. Within the above range, the Grignard reaction is conducive to being fully and effectively carried out.

[0125] In a third aspect, an embodiment of the present application provides a mixture, including a host material and a guest material, wherein the guest material is the boron-nitrogen organic compound described above.

[0126] In some embodiments, the mixture may contain one boron-nitrogen organic compound, or may contain two or more boron-nitrogen organic compounds.

[0127] The host material may be a material known to be used for luminescent materials. As an example, the host material includes but is not limited to one or more of the compounds shown in the following structures:

[0128]

[0129] In some embodiments, the molar ratio of the host material to the guest material ranges from (85 to 99):(1 to 15), for example, 85:1, 85:3, 85:5, 85:6, 85:8, 85:10, 85:12, 85:13, 85:15, 88:1, 88:3, 88:5, 88:6, 88:8, 88:10, 88:12, 88:13, 88:15, 90:1, 90:3, 90:5, 90:6, 90:8, 90:10, 90:12, 90:13, 90:15, 90:1. : 3:1, 93:3, 93:5, 93:6, 93:8, 93:10, 93:12, 93:13, 93:15, 95:1, 95:3, 95:5, 95:6, 95:8, 95:10, 95:12, 95:13, 95:15, 97:1, 97:3, 97:5, 97:6, 97:8, 97:10, 97:12, 97:13, 97:15, 99:1, 99:3, 99:5, 99:6, 99:8, 99:10, 99:12, 99:13, 99:15, etc. Within the above range, it is beneficial to fully transfer the FRET (fluorescence resonance energy transfer) energy between the host material and the guest material, and it is beneficial to improve the luminous efficiency and life of the device.

[0130] In a fourth aspect, an embodiment of the present application further provides a composition, comprising the mixture described above and an organic solvent.

[0131] In some embodiments, the concentration of the composition is in the range of 10 to 30 mg / mL. Within the concentration range, it is beneficial to achieve uniformity of film formation, thereby improving the luminous uniformity, efficiency and life performance of the device.

[0132] The organic solvent is selected from at least one of aromatic or heteroaromatic based solvents, ester based solvents, aromatic ketone based solvents, aromatic ether based solvents, aliphatic ketones, aliphatic ethers, alicyclic compounds, olefin compounds, borate ester compounds and phosphate ester compounds.

[0133] In at least one embodiment, in the composition, the organic solvent is selected from aromatic or heteroaromatic solvents.

[0134] The aromatic or heteroaromatic based solvent may be selected from, but not limited to, p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropyl At least one of biphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate and ethyl 2-furoate.

[0135] The ester-based solvent may be selected from, but not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. At least one of octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate is particularly preferred.

[0136] The aromatic ketone-based solvent may be selected from, but not limited to, 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof. As an example, the derivative may be selected from, but not limited to, at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, and 2-methylpropiophenone.

[0137] The aromatic ether-based solvent may be selected from, but is not limited to, at least one of 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether.

[0138] The aliphatic ketone-based solvent can be selected from, but not limited to, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or an aliphatic ether, for example, at least one of amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether and tetraethylene glycol dimethyl ether.

[0139] It is understood that the organic solvent may be used alone or as a mixed solvent of two or more organic solvents.

[0140] In some embodiments, the composition of the present application includes at least one organic compound or mixture as described above, and at least one organic solvent, and may further include another organic solvent.

[0141] The other organic solvent can be selected from but not limited to at least one of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide (DMSO), tetralin, decalin and indene.

[0142] In some embodiments, organic solvents suitable for the present application are solvents having a Hansen solubility parameter within the following ranges:

[0143] δd (dispersion force) is in the range of 17.0-23.2 MPa1 / 2, especially in the range of 18.5-21.0 MPa1 / 2;

[0144] δp (polar force) is in the range of 0.2-12.5 MPa1 / 2, especially in the range of 2.0-6.0 MPa1 / 2;

[0145] δh (hydrogen bonding force) is in the range of 0.9-14.2 MPa1 / 2, especially in the range of 2.0-6.0 MPa1 / 2.

[0146] In some embodiments, according to the composition of the present application, the boiling point of the organic solvent should be considered when selecting. In at least some embodiments, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; preferably ≥200°C; more preferably ≥250°C; and most preferably ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet print head.

[0147] It will be appreciated that the organic solvent may be evaporated from the solvent system to form a film comprising the organic compound.

[0148] In some embodiments, the composition is a solution. In some other embodiments, the composition is a suspension. The solution or suspension may further include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, etc. The additives may be selected from but not limited to at least one of a surfactant compound, a lubricant, a wetting agent, a dispersant, a hydrophobic agent, and an adhesive.

[0149] The present application also relates to the use of the composition as a coating or printing ink in the preparation of an organic electronic device. In some embodiments, the composition is used to prepare an organic electronic device by a printing or coating preparation method. The printing or coating preparation method can be, but is not limited to, inkjet printing, gravure printing, spray printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spray coating, brush coating, pad printing, slit extrusion coating, etc. Preferred are gravure printing, spray printing and inkjet printing.

[0150] In a fifth aspect, embodiments of the present application provide an application of the boron-nitrogen organic compound or mixture or composition described above in the optoelectronic field.

[0151] In a sixth aspect, an embodiment of the present application provides a photoelectric device, wherein the photoelectric device comprises a functional layer, wherein the functional layer comprises the boron-nitrogen organic compound or the mixture described above.

[0152] It can be understood that the functional layer includes but is not limited to one or more of an electron transport layer, a light emitting layer, a hole transport layer, and a hole injection layer. The photoelectric device also includes an anode and a cathode, the functional layer is located between the anode and the cathode, and the electron transport layer, the light emitting layer, the hole transport layer, and the hole injection layer are stacked in sequence along the direction from the cathode to the anode.

[0153] See also Figure 2 In some embodiments, the optoelectronic device 100 includes an anode 10, a light-emitting layer 20, and a cathode 30 stacked in sequence. The material of the light-emitting layer 20 includes the mixture described above.

[0154] The optoelectronic device 100 described in the present application includes the mixture, and the mixture includes the boron nitrogen organic compound described above, and the boron nitrogen organic compound has an aromatic amine heteroatom condensed ring structure. The heavy atom Se is introduced into the condensed ring structure, which can enhance the spin coupling between S1 (ground state singlet) and T1 (excited triplet), improve the reverse intersystem transition rate, and improve the triplet utilization rate, thereby increasing the PLQY of the material, so that the singlet exciton can quickly realize the radiative transition, avoid the accumulation of high-energy state excitons in the exciton formation process, and cause the luminescent material to decompose, thereby avoiding the triplet annihilation in the luminescent layer, and improving the device stability. In addition, the boron nitrogen organic compound has a narrower emission peak half-peak width, and when it is used in the luminescent layer of the optoelectronic device, the luminous efficiency of the optoelectronic device can be effectively improved. In addition, the boron nitrogen organic compound described in the present application has a deeper LUMO energy level, which can effectively avoid the formation of electron traps in the boron nitrogen organic compound, and improve the device stability and efficiency.

[0155] See also Figure 3 In some embodiments, the optoelectronic device 100 further includes an electron transport layer 40 , and the electron transport layer 40 is disposed between the light emitting layer 20 and the cathode 30 .

[0156] In some embodiments, the optoelectronic device 100 further includes a hole transport layer 50 , and the hole transport layer 50 is located between the light emitting layer 20 and the anode 10 .

[0157] In some embodiments, the optoelectronic device 100 further includes a hole injection layer 60 , and the hole injection layer 60 is disposed between the anode 10 and the hole transport layer 50 .

[0158] In some embodiments, the optoelectronic device 100 further includes an electron injection layer 70 , and the electron injection layer 70 is disposed between the cathode 30 and the electron transport layer 40 .

[0159] The anode 10 and the cathode 30 are anodes and cathodes for optoelectronic devices known in the art, for example, they can be independently and independently include but are not limited to doped metal oxide electrodes, composite electrodes, graphene electrodes, carbon nanotube electrodes, metal single-substance electrodes or alloy electrodes. The material of the doped metal oxide electrode can be but is not limited to one or more of indium-doped tin oxide (ITO), fluorine-doped tin oxide (FTO), antimony-doped tin oxide (ATO), aluminum-doped zinc oxide (AZO), gallium-doped zinc oxide (GZO), indium-doped zinc oxide (IZO), magnesium-doped zinc oxide (MZO), aluminum-doped magnesium oxide (AMO), and cadmium-doped zinc oxide. The composite electrode is an electrode formed by stacking two or more layers of conductive materials, such as AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, TiO2 / Ag / TiO2, TiO2 / Al / TiO2, ZnS / Ag / ZnS, ZnS / Al / ZnS, Ca / Al, LiF / Ca, LiF / Al, BaF2 / Al, CsF / Al, CaCO3 / Al, BaF2 / Ca / Al, etc., wherein " / " represents a stacked structure, for example, AZO / Ag / AZO represents a composite electrode including a sequentially stacked AZO layer, an Ag layer and an AZO layer. The material of the metal single substance electrode may include but is not limited to one or more of Ag, Ni, Pt, Au, Ir, Cu, Mo, Al, Ca, Mg and Ba. The alloy electrode includes, but is not limited to, one or more of an Au:Mg alloy electrode and an Ag:Mg alloy electrode.

[0160] In some embodiments, the anode is an electrode with a relatively high work function, for example, it may include but is not limited to a doped metal oxide electrode with a relatively high work function, a metal single substance electrode with a relatively high work function, and a carbon nanotube electrode. The metal single substance electrode with a relatively high work function may be selected from but is not limited to Ni, Pt, Au, Ag, Ir, etc.

[0161] In some embodiments, the cathode is an electrode with a relatively low work function, for example, it may include but is not limited to a metal single substance electrode with a relatively low work function, a composite electrode with a relatively low work function, and an alloy electrode with a relatively low work function. The metal single substance electrode with a relatively low work function may be Ca, Ba, Al, Mg, etc. The composite electrode with a relatively low work function may be Ca / Al, LiF / Ca, LiF / Al, BaF2 / Al, CsF / Al, CaCO3 / Al, BaF2 / Ca / Al, etc. The alloy electrode with a relatively low work function may be Au:Mg and Ag:Mg, etc.

[0162] The material of the electron transport layer 40 may be a material known in the art for an electron transport layer, for example, may include but is not limited to one or more of an inorganic electron transport material and an organic electron transport material. The inorganic electron transport material may include but is not limited to one or more of a second doped metal oxide particle, a second undoped metal oxide particle, a IIB-VIA semiconductor material, a IIIA-VA semiconductor material, and an IB-IIIA-VIA semiconductor material. The material of the second undoped metal oxide particles includes but is not limited to one or more of ZnO, TiO2, SnO2, ZrO2, and Ta2O5; the metal oxide in the second doped metal oxide particles includes but is not limited to one or more of ZnO, TiO2, SnO2, ZrO2, Ta2O5, and Al2O3; the doping elements in the second doped metal oxide particles include but are not limited to one or more of Al, Mg, Li, Mn, Y, La, Cu, Ni, Zr, Ce, In, and Ga; the IIB-VIA semiconductor materials include but are not limited to one or more of ZnS, ZnSe, and CdS; the IIIA-VA semiconductor materials include but are not limited to one or more of InP and GaP; the IB-IIIA-VIA semiconductor materials include but are not limited to one or more of CuInS and CuGaS. The organic electron transport material includes but is not limited to 8-hydroxyquinoline aluminum (Alq3), LiQ (8-hydroxy lithium phosphate), diphenyl [4- (triphenylsilyl) phenyl] phosphine oxide (TSPO1), 1,3,5-tris ((3-pyridyl)-3-phenyl) benzene (TmPyPB), 2- (4-biphenyl) -5-phenyl oxadiazole (PBD), bis (10-hydroxybenzo [h] quinoline) beryllium (Bebq2) (CAS: 148896-39-3), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl -4H-1,2,4-triazole (TAZ), 2,7-bis (diphenyl phosphine oxide) -9,9'-spiro One or more of bis[fluorene] (SPPO13), 1,3,5-tri(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 4,6-bis(3,5-di(3-pyridyl)phenyl)-2-methylpyrimidine (B3PYMPM), 4,7-diphenyl-1,10-phenanthroline (BPhen), 2-(4'-tert-butylphenyl)-5-(4'-biphenyl)-1,3,4-oxadiazole, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, bis(2-methyl-8-hydroxyquinoline-N1,O8)-1,1'-biphenyl-4-hydroxy)aluminum.

[0163] The material of the hole transport layer 50 is a material known in the art for a hole transport layer, for example, it can be selected from, but not limited to, 4,4'-N,N'-dicarbazolyl-biphenyl (CBP), poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTAA), 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), poly(N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine) (Poly-TPD), N,N'-bis(3 ... methylphenyl)-N,N'-bis(phenyl)-spiro(spiro-TPD), N,N'-bis(4-(N,N'-diphenyl-amino)phenyl)-N,N'-diphenylbenzidine (DNTPD), 4,4',4'-tri(N-carbazolyl)-triphenylamine (TCTA), 4,4',4'-tri(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), poly[(9,9'-dioctylfluorene-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))] (TFB), poly(N-vinylcarbazole) (PVK) and its derivatives, N,N'-di(1-naphthyl)-N,N'-diphenyl-1 ,1'-biphenyl-4-4'-diamine (NPB), spiro NPB, poly(phenylene vinylene) (PPV), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene] (MEH-PPV), poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylene vinylene] (MOMO-PPV), 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene (spiro-omeTAD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), 1,3-bis(carbazol-9-yl)benzene (MCP) , polyaniline, polypyrrole, poly(p-)phenylene vinylene, aromatic tertiary amine, polynuclear aromatic tertiary amine, 4,4'-bis(p-carbazolyl)-1,1'-biphenyl compound, N,N,N',N'-tetraarylbenzidine, PEDOT:PSS and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, poly(spirofluorene) and its derivatives, doped graphene, undoped graphene, C60, doped or undoped NiO, doped or undoped MoO3, doped or undoped WO3, doped or undoped V2O5, doped or undoped P-type gallium nitride, doped or undoped CrO3, doped or undoped CuO. One or more.

[0164] The material of the hole injection layer 60 can be a material known in the art for a hole injection layer, for example, it can be selected from but not limited to one or more of 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), PEDOT, PEDOT:PSS, a derivative of PEDOT:PSS doped with s-MoO3 (PEDOT:PSS:s-MoO3), 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), tetracyanoquinodimethane (F4-TCQN), copper phthalocyanine, nickel oxide, molybdenum oxide, tungsten oxide, vanadium oxide, molybdenum sulfide, tungsten sulfide and copper oxide.

[0165] The material of the electron injection layer 70 may be a material known in the art for a hole injection layer, for example, may be selected from but not limited to one or more of Yb, cesium carbonate, cesium fluoride, cesium azide, and lithium oxide.

[0166] In some embodiments, the thickness of the anode 10 is in the range of 10 to 75 nm.

[0167] In some embodiments, the light emitting layer 20 has a thickness ranging from 30 nm to 70 nm.

[0168] In some embodiments, the cathode 30 has a thickness ranging from 10 to 100 nm.

[0169] In some embodiments, the thickness of the electron transport layer 40 is in the range of 20 to 30 nm.

[0170] In some embodiments, the hole transport layer 50 has a thickness ranging from 20 to 30 nm.

[0171] In some embodiments, the hole injection layer 60 has a thickness ranging from 20 nm to 70 nm.

[0172] In some embodiments, the electron injection layer 70 has a thickness ranging from 20 to 40 nm.

[0173] It is understandable that the optoelectronic device 100 may also be provided with some functional layers conventionally used in optoelectronic devices that help improve the performance of the optoelectronic device, such as an electron blocking layer, a hole blocking layer, etc.

[0174] It can be understood that the materials of each layer of the optoelectronic device 100 can be adjusted according to the light emitting requirements of the optoelectronic device 100 .

[0175] In some embodiments, the optoelectronic device 100 further includes a substrate, and the substrate is disposed on a side of the anode 10 away from the light-emitting layer 20 , or the substrate is disposed on a side of the cathode 30 away from the light-emitting layer 20 .

[0176] The substrate may be a rigid substrate or a flexible substrate. In some embodiments, the material of the substrate may include but is not limited to one or more of glass, silicon wafer, polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate, polyamide and polyether sulfone.

[0177] It is understood that the optoelectronic device 100 may be an upright optoelectronic device or an inverted optoelectronic device. The optoelectronic device 100 may be a quantum dot optoelectronic device or an organic optoelectronic device.

[0178] In a seventh aspect, the present application further relates to a display device, which includes the optoelectronic device 100 .

[0179] The display device can be any electronic product with a display function, including but not limited to smart phones, tablet computers, laptops, digital cameras, digital video cameras, smart wearable devices, smart weighing electronic scales, car displays, televisions or e-book readers, among which smart wearable devices can be, for example, smart bracelets, smart watches, virtual reality (VR) helmets, etc.

[0180] 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.

[0181] Example 1

[0182] The synthesis route of the organic compound M1 of this example is as follows:

[0183]

[0184] Step S11: Add the first compound (10H-phenoselenazine, CAS: 262-05-5) (5mmol, 1.31g) to a 250mL two-necked bottle, add 100mL THF (tetrahydrofuran) and place in a 60°C bath, dissolve NBS (5mmol, 0.89g) in 50mL THF, and slowly dropwise add to the reaction device. After the addition is complete, react for 1h, quench the reaction with 50mL of 1mol / mL sodium thiosulfate aqueous solution, and then extract the reaction solution, select dichloromethane (500mL) and water (200mL) for repeated washing 3 to 4 times, mix the crude product with 300 to 400 mesh silica gel, and separate by column chromatography, using PE as the eluent to obtain the second compound, which is a colorless liquid with a yield of 90%;

[0185] Step S12: Add the second compound (9mmol, 2925mg), cuprous iodide (1.8mmol, 172mg), 18-crown ether-6 (1.8mmol, 476mg) and potassium carbonate (13.5mmol, 1870mg) to a 100mL two-necked bottle, then add 30mL of o-DCB (o-dichlorobenzene), introduce nitrogen, use a vacuum pump to evacuate and ventilate for 20min, stir the reaction solution and heat to 180°C for 24h, stop the reaction, cool to room temperature, remove the reaction solvent by reduced pressure distillation, and then extract the remaining reaction solution, select dichloromethane (800mL) and water (250mL) for repeated washing 3 to 4 times, dry the obtained organic phase with anhydrous magnesium sulfate, filter, concentrate, and perform column chromatography separation, eluent PE (petroleum ether) / EA (ethyl acetate) = 10:2, separate and obtain the third compound, the third compound is a white solid, and the yield is 20%;

[0186] Step S13: Add the third compound (1 mmol, 0.448 g) to a 250 mL two-necked bottle, add 10 mL of THF and place in a 60 ° C bath, dissolve NBS (2 mmol, 0.356 g) in 20 mL of THF, and slowly dropwise add to the reaction device. After the addition is completed, react for 1 hour, quench the reaction with 10 mL of 1 mol / mL sodium thiosulfate aqueous solution, and then extract the reaction solution, select dichloromethane (200 mL) and water (100 mL) for repeated washing 3 to 4 times, mix the crude product with 300 to 400 mesh silica gel, and separate by column chromatography, using PE as the eluent to separate the fourth compound, which is a colorless liquid with a yield of 60%;

[0187] Step S14: In a 250 ml two-necked flask under a nitrogen atmosphere, the fourth compound (2.53 mmol, 1634 mg) and the reaction solvent ultra-dry o-xylene (100 ml) were added, stirred and cooled to 0°C, and then n-butyl lithium (4 ml, 2.5 M, 10 mmol) containing n-hexane solution was slowly added using a syringe, and then the temperature was raised to 50°C for reaction for 2 h, and then the reaction apparatus was lowered to -40°C, and boron tribromide (2.5 g, 10 mmol) was slowly added using a syringe, and then the temperature was raised to 25°C for reaction for 1 h, and then the temperature was lowered to 0°C, and N,N-diisopropylethylamine (2.1 ml, 12 mmol) was added, Then the temperature was raised to 120°C and reacted for 24 hours, then lowered to 25°C, 4-tert-butylphenylmagnesium bromide (CAS: 63488-10-8) (20 ml, 1.0 M, 20 mmol) dissolved in THF was added, and the reaction was stopped after 12 hours. The obtained reaction solution was distilled under reduced pressure to remove the reaction solvent, and the remaining reaction solution was extracted with dichloromethane (100 ml) and water (100 ml). The obtained organic phase was dried over anhydrous sodium sulfate and purified by silica gel chromatography using dichloromethane / petroleum ether (3:7) as eluent to obtain the boron nitrogen organic compound M1 as a light yellow solid with a yield of 50%.

[0188] The NMR data of the organic compound M1 in this example are: 1 H NMR(500MHz,Chloroform-d)δ7.54-7.50(m,4H),7.39-7.35(m,4H),7.14(d,J=8.4Hz,2H), 7.12(dd,J=7.6,1.4Hz,2H),7.06-7.00(m,4H),6.98(dd,J=7.9,1.5Hz,2H),1.34(s,18H).

[0189] Example 2

[0190] The organic compound M4 described above is prepared in this embodiment.

[0191] The synthesis of the organic compound M4 in this embodiment is similar to the synthesis of the organic compound M1 in Example 1, except that 4-diphenylmagnesium bromide (CAS: 3315-91-1) is used in this embodiment to replace 4-tert-butylphenylmagnesium bromide in step S14 of Example 1.

[0192] The NMR data of the organic compound M4 in this example are: 1H NMR(500MHz,Chloroform-d)δ7.76-7.72(m,4H),7.60-7.55(m,8H),7.45-7.40(m,4H),7.38-7 .33(m,2H),7.14(d,J=8.4Hz,2H),7.13-7.09(m,2H),7.02-6.97(m,4H),6.66(d,J=8.4Hz,2H).

[0193] Example 3

[0194] The organic compound M9 described above is prepared in this embodiment.

[0195] The synthesis of the organic compound M9 in this example is similar to that of the organic compound M1 in Example 1, except that 2-naphthylmagnesium bromide (CAS: 21473-01-8) is used in this example to replace 4-tert-butylphenylmagnesium bromide in step S14 of Example 1.

[0196] The NMR data of the organic compound M9 in this example are: 1 H NMR(500MHz,Chloroform-d)δ8.62-8.58(m,2H),8.02(dd,J=8.4,1.9Hz,2H),7.99-7.96(m,2H),7.90-7.87(m,2H),7.86-7.83( m,2H),7.51-7.46(m,2H),7.46-7.42(m,2H),7.23-7.18(m,2H),7.14(d,J=8.4Hz,2H),7.02-6.97(m,4H),6.66(d,J=8.4Hz,2H).

[0197] Example 4

[0198] The organic compound M17 described above is prepared in this embodiment.

[0199] The synthesis of the organic compound M17 of this embodiment is similar to that of the organic compound M1 of Example 1, except that 2-trifluoromethylphenylmagnesium bromide (CAS: 395-47-1) is used in this embodiment to replace 4-tert-butylphenylmagnesium bromide in step S14 of Example 1.

[0200] The NMR data of the organic compound M17 in this example are: 1H NMR(500MHz,Chloroform-d)δ7.45(dd,J=7.6,1.6Hz,2H),7.41-7.38(m,2H),7.35-7.31(m,2H),7.30-7.26(m,2H) ,7.14(dd,J=7.3,1.6Hz,2H),7.06(d,J=8.4Hz,2H),7.03-6.96(m,6H),3.30-3.15(m,2H),1.32(d,J=6.5Hz,12H).

[0201] Example 5

[0202] The organic compound M19 described above is prepared in this embodiment.

[0203] The synthesis of the organic compound M19 of this embodiment is similar to the synthesis of the organic compound M1 of Example 1, except that 2-mesityl magnesium bromide (CAS: 2633-66-1) is used in this embodiment to replace 4-tert-butylphenyl magnesium bromide in step S14 of Example 1.

[0204] The NMR data of the organic compound M19 in this example are: 1 H NMR (500MHz, Chloroform-d) δ7.17-7.14(m,2H),7.08(d,J=8.4Hz,2H),7.04-6.96(m,6H),6.95(s,4H),2.35(s,12H),2.28(s,6H).

[0205] Example 6

[0206] The organic compound M20 described above is prepared in this embodiment.

[0207] The synthesis of the organic compound M20 in this embodiment is similar to that of the organic compound M1 in Example 1, except that p-benzonitrile magnesium bromide (CAS: 412044-48-5) is used in this embodiment to replace 4-tert-butylphenylmagnesium bromide in step S14 of Example 1.

[0208] The NMR data of the organic compound M20 in this example are: 1 H NMR(500MHz,Chloroform-d)δ7.74-7.69(m,4H),7.65-7.59(m,4H),7.15(d,J=8.6H z,2H),7.12(dd,J=7.6,1.5Hz,2H),7.06-7.00(m,4H),6.98(dd,J=7.7,1.5Hz,2H).

[0209] Example 7

[0210] The organic compound M21 described above is prepared in this embodiment.

[0211] The synthesis of the organic compound M21 of this embodiment is similar to that of the organic compound M1 of Example 1, except that 3-thienylmagnesium bromide (CAS: 106032-16-0) is used in this embodiment to replace 4-tert-butylphenylmagnesium bromide in step S14 of Example 1.

[0212] The NMR data of the organic compound M21 in this example are: 1 H NMR(500MHz,Chloroform-d)δ7.60-7.56(m,2H),7.53-7.48(m,4H),7.18(dd,J=7.8,1.2Hz,2H), 7.15(d,J=8.4Hz,2H), 7.11(d,J=8.4Hz,2H), 7.06(t,J=7.8Hz,2H), 6.98(dd,J=7.8,1.2Hz,2H).

[0213] Example 8

[0214] The organic compound M22 described above is prepared in this embodiment.

[0215] The synthesis of the organic compound M22 of this embodiment is similar to that of the organic compound M1 of Example 1, except that 2-furylmagnesium bromide (CAS: 98754-48-4) is used in this embodiment to replace 4-tert-butylphenylmagnesium bromide in step S14 of Example 1.

[0216] The NMR data of the organic compound M22 of this example are: 1 H NMR(500MHz,Chloroform-d)δ8.05(t,J=1.8Hz,2H),7.64(t,J=1.8Hz,2H),7.18(dd,J=7.8,1.2Hz,2H),7.15( d, J=8.4Hz, 2H), 7.12 (d, J=8.4Hz, 2H), 7.07 (t, J=7.8Hz, 2H), 6.98 (dd, J=7.9, 1.3Hz, 2H), 6.91-6.88 (m, 2H).

[0217] Example 9

[0218] The organic compound M23 described above is prepared in this embodiment.

[0219] The synthesis of the organic compound M23 of this embodiment is similar to that of the organic compound M1 of Example 1, except that 3,5-dimethylbenzylmagnesium bromide (CAS: 34696-73-6) is used in this embodiment to replace 4-tert-butylphenylmagnesium bromide in step S14 of Example 1.

[0220] The NMR data of the organic compound M23 in this example are: 1 H NMR(500MHz,Chloroform-d)δ7.52(d,J=2.1Hz,4H),7.15(d,J=8.4Hz,2H),7.12(d d, J=7.6, 1.6Hz, 2H), 7.06-6.99 (m, 6H), 6.97 (dd, J=7.9, 1.5Hz, 2H), 2.36 (s, 12H).

[0221] Example 10

[0222] The organic compound M24 described above is prepared in this embodiment.

[0223] The synthesis of the organic compound M24 in this embodiment is similar to that of the organic compound M1 in Example 1, except that 4-methylphenylmagnesium bromide (CAS: 4294-57-9) is used in this embodiment to replace 4-tert-butylphenylmagnesium bromide in step S14 of Example 1.

[0224] The NMR data of the organic compound M24 in this example are: 1 H NMR (500MHz, Chloroform-d) δ 7.55-7.51 (m, 4H), 7.15 (d, J = 8.4Hz, 2H), 7.13-7.08 (m, 6H), 7.06 (d, J = 8.4Hz, 2H), 7.03-6.97 (m, 4H), 2.39 (d, J = 0.8Hz, 6H).

[0225] Comparative Examples 1 to 7

[0226] The organic compounds of Comparative Examples 1 to 7 are BD01, BD02, BD03, BD04, BD05, BD06, and BD07, respectively.

[0227]

[0228]

[0229] Comparative Example 8

[0230] The synthetic route of the organic compound P1 of this example is as follows:

[0231]

[0232] Step S11: Add the first compound (phenoxazine, CAS: 135-67-1) (5mmol, 0.915g) to a 250mL two-necked bottle, add 100mL THF (tetrahydrofuran) and place in a 60°C bath, dissolve NBS (5mmol, 0.89g) in 50mL THF, slowly dropwise add to the reaction device, react for 1h after the addition is complete, quench the reaction with 50mL sodium thiosulfate aqueous solution with a concentration of 1mol / mL, then extract the reaction solution, select dichloromethane (500mL) and water (200mL) for repeated washing 3 to 4 times, mix the crude product with 300 to 400 mesh silica gel, perform column chromatography separation, and use PE as the eluent to separate the second compound as a colorless liquid with a yield of 90%;

[0233] Step S12: Add the second compound (9mmol, 2196mg), cuprous iodide (1.8mmol, 172mg), 18-crown ether-6 (1.8mmol, 476mg) and potassium carbonate (13.5mmol, 1870mg) to a 100mL two-necked bottle, then add 30mL of o-DCB (o-dichlorobenzene), introduce nitrogen, use a vacuum pump to evacuate and ventilate for 20min, stir the reaction solution and heat to 180°C for 24h, stop the reaction, cool to room temperature, remove the reaction solvent by reduced pressure distillation, and then extract the remaining reaction solution, select dichloromethane (800mL) and water (250mL) for repeated washing 3 to 4 times, dry the obtained organic phase with anhydrous magnesium sulfate, filter, concentrate, and perform column chromatography separation, eluent PE (petroleum ether) / EA (ethyl acetate) = 10:2, and separate the third compound as a white solid with a yield of 20%;

[0234] Step S13: Add the third compound (1 mmol, 0.33 g) to a 250 mL two-necked bottle, add 10 mL of THF and place in a 60 ° C bath, dissolve NBS (2 mmol, 0.356 g) in 20 mL of THF, and slowly add dropwise to the reaction device. After the addition is completed, react for 1 h, quench the reaction with 10 mL of 1 mol / mL sodium thiosulfate aqueous solution, and then extract the reaction solution, select dichloromethane (200 mL) and water (100 mL) for repeated washing 3 to 4 times, mix the crude product with 300 to 400 mesh silica gel, and separate by column chromatography, using PE as the eluent to separate the fourth compound as a colorless liquid with a yield of 60%;

[0235] Step S14: In a 250 ml two-necked flask under a nitrogen atmosphere, the fourth compound (2.53 mmol, 1310 mg) and the reaction solvent ultra-dry o-xylene (100 ml) were added, stirred and cooled to 0°C, and then n-butyl lithium (4 ml, 2.5 M, 10 mmol) containing n-hexane solution was slowly added using a syringe, and then the temperature was raised to 50°C for reaction for 2 h, and then the reaction apparatus was lowered to -40°C, and boron tribromide (2.5 g, 10 mmol) was slowly added using a syringe, and then the temperature was raised to 25°C for reaction for 1 h, and then the temperature was lowered to 0°C, and N,N-diisopropylethylamine (2.1 ml, 12 mmol) was added, Then the temperature was raised to 120°C and reacted for 24 hours, then lowered to 25°C, 4-tert-butylphenylmagnesium bromide (CAS: 63488-10-8) (20 ml, 1.0 M, 20 mmol) dissolved in THF was added, and the reaction was stopped after 12 hours. The obtained reaction solution was distilled under reduced pressure to remove the reaction solvent, and the remaining reaction solution was extracted with dichloromethane (100 ml) and water (100 ml). The obtained organic phase was dried over anhydrous sodium sulfate and purified by silica gel chromatography using dichloromethane / petroleum ether (3:7) as eluent to obtain the boron nitrogen organic compound M1 as a light yellow solid with a yield of 50%.

[0236] The NMR data of the organic compound P1 in this example are: 1 H NMR(500MHz,Chloroform-d)δ7.54-7.50(m,4H),7.39-7.35(m,4H),7.14(d,J=8.4Hz,2H), 7.12(dd,J=7.6,1.4Hz,2H),7.06-7.00(m,4H),6.98(dd,J=7.9,1.5Hz,2H),1.34(s,18H).

[0237] The PLQY tests were performed on the organic compounds of Examples 1 to 10 and Comparative Examples 1 to 8, respectively. The test results are shown in Table 1.

[0238] The testing method of PLQY test is as follows: organic compounds M1, M4, M9, M17, M19, M20, M21, M22, M23, M24, and P1 are respectively dissolved in cyclohexylbenzene (concentration is 20 mg / mL), and spin-coated on a clean quartz wafer (film thickness is 50 nm) with a spin coater, wherein the rotation speed is 1200 rpm, the time is 30 s, and then baked at 140°C for 20 minutes. After packaging, the steady-state fluorescence spectrometer of Edinburgh Instruments is used for testing. The model of the instrument is FS5, and the corresponding accessory for measuring fluorescence quantum yield is SC-30.

[0239] Table 1:

[0240] Organic compounds PLQY(%) Example 1 M1 95 Example 2 M4 90 Example 3 M9 85 Example 4 M17 88 Example 5 M19 87.5 Example 6 M20 89 Example 7 M21 95 Example 8 M22 97 Example 9 M23 91 Example 10 M24 84 Comparative Example 1 BD01 70 Comparative Example 2 BD02 65 Comparative Example 3 BD03 68 Comparative Example 4 BD04 66 Comparative Example 5 BD05 69 Comparative Example 6 BD06 64 Comparative Example 7 BD07 66 Comparative Example 8 P1 70

[0241] From Table 1 we can see that:

[0242] Compared with the organic compounds of comparative examples 1 to 8, the organic compounds of embodiments 1 to 10 of the present application have higher fluorescence quantum efficiency. The reason may be that the boron nitrogen organic compounds described in the present application have an aromatic amine heteroatom condensed ring structure. The introduction of heavy atom Se in the condensed ring structure can enhance the spin coupling between S1 (ground singlet state) and T1 (excited triplet state), increase the reverse intersystem transition rate, and improve the triplet state utilization rate, thereby increasing the PLQY of the boron nitrogen organic compounds.

[0243] Device performance testing

[0244] The method for preparing the device comprises:

[0245] Pretreatment of indium zinc oxide (IZO) coated glass (specifications: thickness of 75nm, sheet resistance of 10Ωm-2, surface size of 30mm×30mm): Use a cleaning machine to perform program cleaning in sequence, where each cleaning step takes 120s, thoroughly clean the stains and dust on the surface of the ITO glass substrate, bake it on a hot plate at 230℃ for 30 minutes, and then put it in an electric hot air drying oven for 24 hours to dry it for use, and then use UV exposure and O2 plasma treatment for 15 minutes to reduce the surface work enthalpy of the dried glass substrate;

[0246] The pretreated ITO glass substrate was used as the device anode. Then, the ink containing PEODT:PSS material was poured into the inkjet printer cartridge in a nitrogen glove box. Each pixel was injected with 9 picoliters of hole injection layer ink, and VD5min (vacuum degree 1×10 -4 mPa), annealed at 230°C for 30 minutes to obtain a hole injection layer with a thickness of 25 nm;

[0247] Then, TFB (concentration of 40 mg / ml) dissolved in a mixed solution of xylene and cyclohexylbenzene was filtered and poured into the inkjet printer cartridge. 10 pL of hole transport layer ink was injected into each pixel luminous point and VD was performed for 5 min (vacuum degree was 1×10 -4 mPa), and annealing was performed at 230°C for 30 minutes to obtain a hole transport layer with a thickness of 60 nm;

[0248] The luminescent layer material (concentration 20 mg / ml) was prepared into ink and poured into the inkjet printer cartridge. 50 picoliters was injected into each pixel of the hole transport layer and VD was performed for 5 min (vacuum degree 1×10 -4 mPa), annealed at 140°C for 20 min to form a light-emitting layer with a thickness of 40 nm;

[0249] Transfer it to the vacuum evaporation chamber (vacuum degree is 5×10 -7 Pa), vacuum evaporation was performed, and LiQ and TPBi (mass ratio was 2:8) were vacuum evaporated on the light-emitting layer using a mask to form an electron transport layer with a thickness of 30 nm;

[0250] Yb is evaporated on the electron transport layer to form an electron injection layer with a thickness of 1 nm;

[0251] Ag was evaporated onto the electron transport layer to form a cathode with a thickness of 25 nm;

[0252] A 60nm thick refractive layer CPL is evaporated on the cathode;

[0253] Finally, the organic electroluminescent device was obtained by UV curing packaging and heating and baking for 20 minutes.

[0254] The device structure of this embodiment is: ITO / PEDOT:PPS / TFB / QD / M1 / Ag.

[0255] The compositions of the light-emitting layer materials of device embodiments 1 to 10 and device comparative examples 1 to 8 are shown in Table 2 below.

[0256] Table 2:

[0257]

[0258]

[0259] Device performance test:

[0260] The photoelectric devices of device embodiments 1 to 10 and device comparative examples 1 to 8 were respectively subjected to EQE relative value test and half-maximum full width FWHM test. The test results are shown in Table 3.

[0261] Among them, the test method of EQE relative value test is: using FPD optical property measurement equipment from Foster, controlling the efficiency test system built by QE PRO spectrometer, Keithley 2400, and Keithley 6485 through LabView, measuring parameters such as voltage, current, brightness, and luminous spectrum, obtaining the maximum brightness, and calculating the external quantum efficiency EQE of the device. The specific calculation formula is as follows:

[0262]

[0263] Where ηe is the light output coupling efficiency, ηr is the ratio of the number of recombined carriers to the number of injected carriers, χ is the ratio of the number of excitons that generate photons to the total number of excitons, KR is the radiation process rate, and KNR is the non-radiative process rate;

[0264] The test method for the relative value of the life span T95@1000nit is: the time required for the brightness of the device to decrease to a certain proportion of the maximum brightness under constant current or voltage drive, and the time when the brightness drops to 95% of the maximum brightness is defined as T95, and this life span is the measured life span. In order to shorten the test cycle, the device life span test is usually carried out at high brightness by accelerating device aging, and the life span at high brightness is obtained by fitting the extended exponential decay brightness attenuation fitting formula, for example: the life span at 1000nit is calculated as T95@1000nit. The specific calculation formula is as follows:

[0265]

[0266] 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 the A value is 1.7.

[0267] Table 3:

[0268] EQE relative value FWHM(nm) <![CDATA[LT 95 @1000nits relative value]]> Device Example 1 1.81 23 1.71 Device Example 2 1.9 24 1.74 Device Example 3 1.7 25 1.82 Device Example 4 1.86 24 1.85 Device Example 5 1.91 25 1.95 Device Example 6 1.82 24 1.79 Device Example 7 1.91 23 1.77 Device Example 8 1.94 25 1.88 Device Example 9 1.84 24 1.96 Device Example 10 1.84 24 1.96 Device Comparison Example 1 1 30 1 Device Comparison Example 2 1.13 29 1.1 Device Comparison Example 3 1.21 30 1.12 Device Comparison Example 4 1.15 29 1.14 Device Comparison Example 5 0.9 40 0.5 Device Comparative Example 6 1.12 35 0.7 Device Comparison Example 7 1.12 35 0.95 Device Comparison Example 8 1.22 37 1.1

[0269] From Table 3 we can see that:

[0270] Compared with the light-emitting devices of device comparison examples 1 to 8, the light-emitting devices of device embodiments 1 to 10 have higher external quantum efficiency EQE, narrower half-peak width and longer life. It can be seen that the use of the organic compound of the present application as the guest material of the light-emitting layer can effectively improve the efficiency and life of the device. The reason may be that the boron nitrogen organic compound described in the present application has an aromatic amine heteroatom condensed ring structure. The introduction of heavy atoms Se in the condensed ring structure can enhance the spin coupling between S1 and T1, increase the reverse intersystem transition rate, and improve the triplet utilization rate, thereby increasing the boron nitrogen organic compound. PLQY enables singlet excitons to quickly achieve radiative transitions, avoids the accumulation of high-energy excitons during exciton transfer, and causes the decomposition of the luminescent material, thereby avoiding the triplet annihilation of the boron nitrogen organic compound in the luminescent layer and improving the stability of the device; the boron nitrogen organic compound has a narrow emission peak half-width, and when it is used in the luminescent layer of an optoelectronic device, the luminescence efficiency of the optoelectronic device can be effectively improved; in addition, the boron nitrogen organic compound described in the present application has a deeper LUMO energy level, which can effectively avoid the formation of electron traps in the boron nitrogen organic compound, thereby improving the stability and efficiency of the device.

[0271] The technical solutions provided by 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 method of the present application and its core idea. At the same time, for technical personnel in this field, according to the idea of ​​the present application, there will be changes in the specific implementation methods and application scope. In summary, the content of this specification should not be understood as a limitation on the present application.

Claims

1. A boron-nitrogen organic compound, characterized in that: It has the structure shown in formula (I): Wherein, n1 is independently any integer from 1 to 2 each time it appears, and n2 is independently any integer from 1 to 3 each time it appears; L1 and L2 are each independently 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 of these groups; R1 and R2 are each independently selected from hydrogen, deuterium, cyano, isocyano, -Cl, -Br, -F, -I, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C1~C 20 Alkoxy, substituted or unsubstituted C1~C 20 Alkylthio, substituted or unsubstituted C1~C 20 Alkylcarbonyl, substituted or unsubstituted C1~C 20 alkoxycarbonyl, substituted or unsubstituted aryloxy having 6 to 30 ring atoms, substituted or unsubstituted aryloxycarbonyl having 6 to 30 ring atoms, substituted or unsubstituted C2 to C 20 alkenyl, substituted or unsubstituted aryl having 6 to 60 ring atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, substituted or unsubstituted heteroaryloxy having 5 to 30 ring atoms, or a combination of these groups; When substituted with a substituent, each occurrence of the substituent is independently selected from deuterium, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C 20 Alkyl, C1~C 20 A combination of one or more of an alkoxy group and an aryl group having 6 to 30 ring atoms.

2. The boron-nitrogen organic compound according to claim 1, characterized in that L1 and L2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or a combination of these groups; and / or, R1 and R2 are each independently selected from hydrogen, deuterium, cyano, isocyano, -Cl, -Br, -F, -I, substituted or unsubstituted C1-C 18 Alkyl, substituted or unsubstituted C1~C 18 Alkoxy, substituted or unsubstituted C1~C 18 Alkylthio, substituted or unsubstituted C1~C 18 Alkylcarbonyl, substituted or unsubstituted C1~C 18 alkoxycarbonyl, substituted or unsubstituted aryloxy having 6 to 20 ring atoms, substituted or unsubstituted aryloxycarbonyl having 6 to 20 ring atoms, substituted or unsubstituted C2 to C 18 Alkenyl, substituted or unsubstituted aryl having 6 to 50 ring atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, substituted or unsubstituted heteroaryloxy having 5 to 30 ring atoms, or a combination of these groups.

3. The boron-nitrogen organic compound according to claim 1, characterized in that L1 and L2 are each independently selected from any one of the following groups: Wherein, m1 is any integer from 0 to 5, m2 is any integer from 0 to 3, m3 is any integer from 0 to 9, m4 and m5 are each independently any integer from 0 to 7, m6, m7, and m8 are each independently any integer from 0 to 4, and m6, m7, and m8 are not 4 at the same time; Each occurrence of M is independently selected from O, S, CR 11 R 12 or NR 13 ; M' is selected from N or phenyl; L3 is selected from a single bond or is absent; R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 Each occurrence is independently selected from halogen, cyano, substituted or unsubstituted C1-C 20 Straight chain alkyl, substituted or unsubstituted C3~C 20 Branched alkyl, substituted or unsubstituted C1~C 20 Straight chain alkoxy, substituted or unsubstituted C3~C 20 branched alkoxy, or a combination of these groups; and / or, R1 and R2 are each independently selected from hydrogen, deuterium, cyano, isocyano, -Cl, -Br, -F, -I, substituted or unsubstituted C1-C 15 Straight chain alkyl, substituted or unsubstituted C1~C 15 Straight chain alkoxy, substituted or unsubstituted C1~C 15 Straight chain alkylthio, substituted or unsubstituted C3~C 15 Branched alkyl, substituted or unsubstituted C3~C 15 Branched alkoxy, substituted or unsubstituted C3~C 15 Branched alkylthio, substituted or unsubstituted C3~C 15 Cyclic alkyl, substituted or unsubstituted C3~C 15 Cyclic alkoxy, substituted or unsubstituted C3~C 15 Cyclic alkylthio, substituted or unsubstituted C1~C 15 Alkylcarbonyl, substituted or unsubstituted C1~C 15 alkoxycarbonyl, substituted or unsubstituted aryloxy having 6 to 15 ring atoms, substituted or unsubstituted aryloxycarbonyl having 7 to 15 ring atoms, substituted or unsubstituted C2 to C 15 Alkenyl, substituted or unsubstituted aryl having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, substituted or unsubstituted heteroaryloxy having 5 to 30 ring atoms, or a combination of these groups.

4. The boron-nitrogen organic compound according to claim 1, characterized in that L1 and L2 are each independently selected from any one of the following groups: and / or, R1 and R2 are each independently selected from hydrogen, deuterium, cyano, -Cl, -Br, -F, -I, substituted or unsubstituted C1-C 10 Straight chain alkyl, substituted or unsubstituted C1~C 10 Straight chain alkoxy, substituted or unsubstituted C1~C 10 Straight chain alkylthio, substituted or unsubstituted C3~C 10 Branched alkyl, substituted or unsubstituted C3~C 10 Branched alkoxy, substituted or unsubstituted C3~C 10 Branched alkylthio, substituted or unsubstituted C3~C 10 Cyclic alkyl, substituted or unsubstituted C3~C 10 Cyclic alkoxy, substituted or unsubstituted C3~C 10 Cyclic alkylthio, substituted or unsubstituted C1~C 10 Alkylcarbonyl, substituted or unsubstituted C1~C 10 alkoxycarbonyl, substituted or unsubstituted aryloxy having 6 to 10 ring atoms, substituted or unsubstituted aryloxycarbonyl having 7 to 10 ring atoms, substituted or unsubstituted C2 to C 10 Alkenyl, substituted or unsubstituted aryl having 6 to 20 ring atoms, substituted or unsubstituted heteroaryl having 5 to 20 ring atoms, substituted or unsubstituted heteroaryloxy having 5 to 20 ring atoms, or a combination of these groups.

5. The boron-nitrogen organic compound according to claim 1, characterized in that The boron-nitrogen organic compound is selected from any one of the following structural formulas:

6. A method for preparing a boron-nitrogen organic compound, characterized in that: The steps include: Mixing the first compound with a first halogenating agent to perform a first halogenation reaction to obtain a second compound; subjecting the second compound to a coupling reaction to obtain a third compound; The third compound is mixed with the second halogenating agent to perform a first halogenation reaction to obtain a fourth compound; as well as Under the conditions of lithium salt, boron halide, organic amine and Grignard reagent, the fourth compound is subjected to lithiation-boration-Grignard reaction through a one-pot method to obtain a boron-nitrogen organic compound.

7. The preparation method according to claim 6, characterized in that: The method comprises at least one of the following features (1) to (24): (1) The first compound includes 10H-phenoselenazine; (2) the first halogenating agent and the second halogenating agent each independently include N-halogenated succinimide, and the N-halogenated succinimide includes one or more of N-bromosuccinimide, N-iodosuccinimide, and N-iodosuccinimide; (3) a base is added during the coupling reaction, wherein the base includes one or more of potassium carbonate, potassium phosphate, and cesium carbonate; (4) A catalyst is added during the coupling reaction, wherein the catalyst includes one or more of cuprous iodide, cuprous bromide, and cuprous chloride; (5) A ligand is also added during the coupling reaction, wherein the ligand includes one or more of 18-crown-6 and 12-crown-4; (6) The lithium salt includes an organic lithium salt, the organic lithium salt includes an alkyl lithium salt, and the alkyl lithium salt includes one or more of n-butyl lithium and tert-butyl lithium; (7) The boron halide includes one or more of boron tribromide and boron triiodide; (8) The organic amine includes one or more of 1,2,2,6,6-pentamethylpiperidine and N,N-diisopropylethylamine; (9) The Grignard reagent includes an organic magnesium bromide, and the organic magnesium bromide includes one or more of 4-tert-butylphenylmagnesium bromide, 4-diphenylmagnesium bromide, 2-naphthylmagnesium bromide, 2-trifluoromethylphenylmagnesium bromide, 2-mesitylmagnesium bromide, p-benzonitrilemagnesium bromide, 3-thienylmagnesium bromide, 2-furylmagnesium bromide, 3,5-xylylmagnesium bromide, and 4-methylphenylmagnesium bromide; (10) The molar ratio of the first compound to the first halogenating agent is 1:(1-1.5); (11) A base is added during the coupling reaction, and the molar ratio of the second compound to the base is 1:(1-2); (12) A catalyst is added during the coupling reaction, and the molar ratio of the second compound to the catalyst is 1:(0.15-0.25); (13) A ligand is added during the coupling reaction, and the molar ratio of the second compound to the ligand is 1:(0.15-0.25); (14) The molar ratio of the third compound to the second halogenating agent is 1:(2-4.5); (15) The molar ratio of the fourth compound to the lithium salt is 1:(2-6); (16) The molar ratio of the fourth compound to the boron halide is 1:(2-6.5); (17) The molar ratio of the fourth compound to the organic amine is 1:(2-5); (18) The molar ratio of the fourth compound to the Grignard reagent is 1:(2-10); (19) The temperature of the first halogenation reaction is 50 to 75° C. and the time is 1 to 4 hours; (20) The coupling reaction temperature is 160-190°C and the reaction time is 12-24h; (21) The temperature of the second halogenation reaction is 50 to 75° C. and the time is 1 to 4 hours; (22) The temperature of the lithiation reaction is -50 to 0°C; (23) The temperature of the borylation reaction is -50 to 120°C; (24) The temperature of the Grignard reaction is 10 to 50°C.

8. Use of the boron-nitrogen organic compound according to any one of claims 1 to 5 in the field of optoelectronics.

9. A composition comprising a host material and a guest material, characterized in that: The guest material is the boron-nitrogen organic compound according to any one of claims 1 to 5.

10. The composition according to claim 9, characterized in that The molar ratio of the host material to the guest material is in the range of (85-99): (1-15); And / or, the composition further comprises an organic solvent.

11. A photoelectric device, characterized in that: The photoelectric device comprises a functional layer, and the functional layer comprises the boron-nitrogen organic compound according to any one of claims 1 to 5.

12. The optoelectronic device according to claim 11, characterized in that The functional layer includes a light-emitting layer, and the light-emitting layer includes the boron-nitrogen organic compound.

13. The optoelectronic device according to claim 11, characterized in that The functional layer includes one or more of an electron transport layer, a light-emitting layer, a hole transport layer, and a hole injection layer. The photoelectric device also includes an anode and a cathode. The functional layer is located between the anode and the cathode, and the electron transport layer, the light-emitting layer, the hole transport layer, and the hole injection layer are stacked in sequence along the direction from the cathode to the anode.

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