Organic compound as well as preparation method and application thereof

Abstract

The invention discloses an organic compound as well as a preparation method and application thereof, the organic compound provided by the invention has good electrochemical stability and a water and oxygen adsorption effect, and not only can achieve the effects of adsorbing water and oxygen and avoiding water and oxygen erosion.

Description

Technical Field

[0001] This application relates to the field of organic compounds, and particularly to an organic compound, a preparation method thereof, and an application thereof. Background Art

[0002] For some devices that are extremely sensitive to water and oxygen, exposure to a water-oxygen environment will greatly affect the device performance and lead to a decrease in device stability. To this end, a packaging layer is usually provided on the surface of the device to protect the device from water and oxygen erosion. Summary of the Invention

[0003] In view of this, this application provides an organic compound, a preparation method thereof, and an application thereof.

[0004] The embodiments of this application are implemented as follows:

[0005] In a first aspect, the embodiments of this application provide an organic compound having a structure shown in formula (I):

[0006]

[0007] wherein, n1 is selected from any integer from 0 to 5, and n2 is selected from any integer from 0 to 5;

[0008] M is selected from any one of metal atoms of Group VIIB and metal atoms of Group VIII; R 1 and R 2 each independently represents, each time it appears: a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C6-C30 heteroarylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C2-C30 alkynylene group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 heteroaryloxy group, or a combination of one or more of the foregoing.

[0009] In a second aspect, this application provides a method for preparing an organic compound, characterized by comprising the following steps:

[0010] Mix compound a and an acyl chlorination reagent to carry out a first reaction to obtain intermediate N-1;

[0011] Mix the intermediate N-1 and compound b to carry out a second reaction to obtain intermediate N-2;

[0012] Mix the intermediate N-2 and a reducing agent to carry out a third reaction to obtain intermediate N-3;

[0013] Mix the intermediate N-3 and thiourea and carry out the fourth reaction to obtain the organic compound M;

[0014] Among them, the structural formulas of the compound a, the compound b, the intermediate N-1, the intermediate N-2, the intermediate N-3, and the organic compound N are as follows:

[0015]

[0016] Among them, n1 is selected from any integer from 0 to 5, and n2 is selected from any integer from 0 to 5;

[0017] M is selected from any one of the Group VIIB metal atoms and the Group VIII metal atoms;

[0018] The compound a includes a compound with the general formula X 1 -R 1 -COOH and a compound with the general formula X 2 -R 2 -COOH. The intermediate N-1 includes a compound with the general formula X 1 -R 1 -COCl and a compound with the general formula X 2 -R 2 -COCl;

[0019] R 1 、R 2 Each occurrence is independently selected from: substituted or unsubstituted C1-C30 alkylene, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C2-C30 alkenylene, substituted or unsubstituted C2-C30 alkynylene, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 heteroaryloxy, or a combination of one or more of them;

[0020] X 1 、X 2 Each occurrence is independently selected from halogen groups.

[0021] In a third aspect, the present application provides a composition, including a solvent and a first compound, where the first compound includes the organic compound described above, or an organic compound prepared by the preparation method described above.

[0022] In a fourth aspect, the present application further provides a film, where the film is prepared from the composition described above, or the material of the film includes a second compound, where the second compound includes the organic compound described above, or an organic compound prepared by the preparation method described above.

[0023] In a fifth aspect, the present application provides an optoelectronic device, including a device body and a packaging layer disposed on the surface of the device body, where the packaging layer includes the thin film described above.

[0024] In a sixth aspect, the present application provides a method for manufacturing an optoelectronic device, including the following steps:

[0025] Provide a device body and a thin film material;

[0026] Dispose the thin film material on the device body to form a packaging layer, thereby obtaining an optoelectronic device;

[0027] Wherein, the thin film material includes the composition, or includes a second compound, the second compound includes the organic compound described above, or is an organic compound prepared by the preparation method described above.

[0028] In a seventh aspect, the present application provides a display device, including the optoelectronic device described above, or an optoelectronic device prepared by the preparation method described above.

[0029] The organic compound proposed by the technical solution of the present application has good electrochemical stability and can adsorb water and oxygen. It can not only adsorb water and oxygen to avoid the erosion of water and oxygen. Description of the Drawings

[0030] To more clearly illustrate the technical solutions in the embodiments of the present application, the following will briefly introduce the drawings required for the description of the embodiments. Obviously, the drawings in the following description are only some embodiments of the present application. For those skilled in the art, without creative efforts, other drawings can be obtained based on these drawings.

[0031] Figure 1 It is a schematic structural diagram of an embodiment of an optoelectronic device provided by the present application;

[0032] Reference numerals: Optoelectronic device 1000; Device body 100; Anode 10; Cathode 20; Light-emitting layer 30; Packaging layer 200. Detailed Embodiments

[0033] The following will clearly and completely describe the technical solutions in the embodiments of the present application with reference to the accompanying drawings in the embodiments of the present application. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative efforts belong to the scope of protection of the present application. In addition, it should be understood that the specific implementation manners described herein are only used to illustrate and explain the present application, and are not used to limit the present application. In the present application, unless otherwise stated, the orientation terms such as "upper" and "lower" specifically refer to the drawing directions in the accompanying drawings. In addition, in the description of the present application, the term "including" means "including but not limited to". The various embodiments of the present application may exist in the form of a range; it should be understood that the description in the form of a range is only for convenience and brevity, and should not be construed as a rigid limitation on the scope of the present application; therefore, it should be considered that the description of the range has specifically disclosed all possible sub-ranges and single values within that range. For example, it should be considered that the description of the range from 1 to 6 has specifically disclosed sub-ranges such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., and single numbers within that range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. In addition, whenever a numerical range is indicated herein, it means including any cited number (fraction or integer) within the indicated range.

[0034] In the present application, "and / or" describes the association relationship of associated objects, indicating that there can be three relationships. For example, A and / or B can represent: A exists alone, A and B exist simultaneously, or B exists alone. Wherein A and B can be singular or plural.

[0035] In the present application, "at least one" means one or more, and "a plurality" means two or more. "At least one kind", "at least one of the following items (pieces)" or similar expressions refer to any combination of these items, including any combination of single items (pieces) or plural items (pieces). For example, "at least one of a, b, or c", or "at least one of a, b, and c" can both represent: a, b, c, a - b (i.e., a and b), a - c, b - c, or a - b - c, where a, b, and c can be single or multiple respectively.

[0036] Term Explanation

[0037] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or may not be substituted. When the defined group is substituted, it should be understood as being optionally substituted by groups acceptable in the art, including but not limited to: hydroxyl, amino, halogen, carboxyl, nitro, sulfonic acid group, mercapto, cyano, C1-C5 alkoxy, C1-C5 alkylcarbonyl, heteroaryl having 5-20 ring atoms, aryl having 6-20 ring atoms, heteroaryloxy having 5-20 ring atoms, aryloxy having 6-20 ring atoms, or a combination of one or more of them. In the present application, "a combination of multiple" means a case where at least one hydrogen in a group is substituted by other groups (it may be substituted by one other group or may be substituted by multiple other groups). For example, a combination of hydroxyl, halogen, and amino may mean that at least two hydrogens in the amino group are respectively substituted by hydroxyl and halogen.

[0038] In the present application, when the same substituent appears multiple times, it may be independently selected from different groups. For example, if the general formula contains multiple R1s, then R1s may be independently selected from different groups. For example 6 Rs on the benzene ring 1 may be the same as or different from each other.

[0039] In the present application, "alkyl" may represent a straight-chain alkyl, a branched-chain alkyl, and / or a cyclic alkyl. The number of carbon atoms of the alkyl may be 1-50, 1-30, 1-20, 1-10, or 1-6. Phrases containing this term, for example, "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence can independently be a C1 alkyl group, C2 alkyl group, C3 alkyl group, C4 alkyl group, C5 alkyl group, C6 alkyl group, C7 alkyl group, C8 alkyl group or C9 alkyl group. 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-butyl octyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc. Thioalkyl refers to a group in which at least one hydrogen in the alkyl group is replaced by a sulfur atom. "Alkylene" refers to the group obtained by removing one hydrogen from the alkyl group, and its general formula can be "-C n H 2n -". Alkoxy represents "-O-alkyl" or "-O-C n H 2n+1 "; alkyleneoxy represents "-O-alkylene-" or "-O-C n H 2n -".

[0040] In this application, "-C n H 2n -", without special indication or limitation, represents a straight-chain alkylene group. For example, -C6H 12 - represents n-hexylene, -C 12 H 22 - represents n-dodecylene.

[0041] In the present application, "the number of ring atoms" refers to the number of atoms among the atoms constituting the ring itself in a structural compound obtained by bonding atoms into a ring (for example, a monocyclic compound or a polycyclic compound). It can be understood that the ring atoms are not limited to carbon atoms. When a heterocycle is contained in a cyclic compound, the heteroatoms are also the atoms constituting the heterocycle and belong to the ring atoms. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below under the condition of no special description. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0042] In the present application, "aryl, aromatic group or aromatic radical" refers to a hydrocarbon group containing at least one aromatic ring, such as a monocyclic compound, a fused-ring compound or a polycyclic non-fused compound, etc. "Heteroaromatic group or heteroaromatic radical" refers to an aromatic hydrocarbon group containing at least one heteroatom, such as a monocyclic compound containing at least one heteroatom, a fused-ring compound containing at least one heteroatom or a polycyclic non-fused compound containing at least one heteroatom, etc. The heteroatoms are preferably selected from Si, N, P, O, S and / or Ge, and particularly preferably selected from Si, N, P, O and / or S. Among them, the fused-ring compound or the fused compound has the same meaning and can be interchanged. Specifically, it means that the compound can have two or more rings, and two ring atoms are shared by two adjacent rings, that is, a fused ring. For the purpose of the present application, the aromatic group or heteroaromatic group includes not only the system of aromatic rings but also non-aromatic ring systems. Therefore, for example, systems such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, carbene, etc. are also considered aromatic groups or heteroaromatic groups for the purpose of this invention. For the purpose of the present application, the fused-ring aromatic or fused heteroaromatic ring system includes not only the system of aromatic groups or heteroaromatic groups, but also, in which, a plurality of aromatic groups or heteroaromatic groups can be interrupted by short non-aromatic units (<10% of non-H atoms, preferably less than 5% of non-H atoms, such as C, N or O atoms). Therefore, for example, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, etc. are also considered fused-ring aromatic ring systems for the purpose of this invention. "Arylene" refers to a group obtained by removing one hydrogen from an aryl group, and its general formula can be "-Ar1-"; "heteroarylene" refers to a group obtained by removing one hydrogen from a heteroaryl group, and its general formula can be "-Ar2-". Aryloxy represents "-O-arylene-" or "-O-Ar1-"; heteroaryloxy represents "-O-heteroarylene-" or "-O-Ar2-".

[0043] In a preferred embodiment, the aromatic group is selected from: benzene, naphthalene, anthracene, fluoranthene, phenanthrene, benzophenanthrene, dibenzo[a,h]anthracene, tetracene, pyrene, benzopyrene, acenaphthene, fluorene, and their derivatives; the heteroaromatic group is selected from triazine, pyridine, pyrimidine, imidazole, furan, thiophene, benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thiophenopyrrole, thiophenothiophene, furanopyrrole, furanofuran, thiophenofuran, benzisoxazole, benzisothiazole, benzimidazole, quinoline, isoquinoline, phthalazine, quinoxaline, phenanthridine, perimidine, quinazoline, quinazolinone, dibenzothiophene, dibenzofuran, carbazole, and their derivatives.

[0044] In the present application, alkenylene refers to -(R3) a -CR1=CR2-(R4) b -; alkynylene refers to *- a (R3)-C≡C-(R4) b -*; wherein, a and b are 0 or positive integers, R1 and R2 each independently represent H or alkyl, and R3 and R4 each independently represent substituted or unsubstituted alkylene. C2-C30 alkenylene represents that the total number of carbon atoms in the alkenylene is 2 to 30. For example, C3 alkenylene can be -CH2=CHCH2-.

[0045] In the present application, amino represents -NR 1 R 2 wherein, R 1 and R 2 each independently represent H or alkyl, that is, amino can refer to -NH2, -NH(alkyl), or -N(alkyl)(alkyl).

[0046] In the present application, "halogen group" represents -Cl, -Br, -F, or -I; hydroxyl represents -OH; carboxyl represents -COOH; nitro represents -NO2; mercapto represents -SH; cyano represents *-C≡N; alkoxycarbonyl represents alkylcarbonyl represents wherein, R represents straight-chain alkyl or branched-chain alkyl.

[0047] In the present application, "their combinations", "any combination thereof", "any combination mode thereof", etc. include all suitable combination modes of any two or any two or more items in the listed items.

[0048] In a first aspect, an embodiment of the present application provides an organic compound having a structure shown in formula (I):

[0049]

[0050] wherein, M is selected from any one of Group VIIB metal atoms and Group VIII metal atoms.

[0051] Wherein: n1 is selected from any integer from 0 to 5, such as 0, 1, 2, 3, 4 or 5; n2 is selected from any integer from 0 to 5, such as 0, 1, 2, 3, 4 or 5.

[0052] Specifically, the compound has the structure shown in the following formula, wherein X is -CH2-R 1 -SH, and Y is -CH2-R 2 -SH. n1 hydrogens among 0 to 5 sites on one cyclopentadiene ring are each independently substituted by X. When the number of substituted X is two or more, two or more Xs can be the same or different; n2 hydrogens among 0 to 5 sites on the other cyclopentadiene ring are each independently substituted by Y. When the number of substituted Y is two or more, two or more Ys can be the same or different.

[0053]

[0054] R 1 、R 2 Each occurrence of R is independently selected from: substituted or unsubstituted C1-C30 alkylene, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C2-C30 alkenylene, substituted or unsubstituted C2-C30 alkynylene, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 heteroaryloxy, or a combination of one or more of them.

[0055] In the substituted C1-C30 alkylene, substituted C6-C30 arylene, C6-C30 heteroarylene, substituted C2-C30 alkenylene, substituted C2-C30 alkynylene, substituted C1-C30 alkoxy, substituted C6-C30 aryloxy, substituted C6-C30 heteroaryloxy, the substituents are selected from any one or more of C1 to C10 alkyl, C1 to C10 alkoxy, C2 to C10 alkoxycarbonyl, C2 to C10 alkylcarbonyl, C6 to C30 aryl, cyano, nitro, mercapto, hydroxy, carboxy, amino, halogen groups.

[0056] Wherein, M is selected from Fe (iron), Co (cobalt), Ni (nickel) or Mn (manganese).

[0057] The organic compound proposed in the technical solution of this application has good electrochemical stability and can adsorb water and oxygen. It can not only adsorb water and oxygen to avoid the erosion of water and oxygen, but also be applicable to an electric field environment and effectively play an antioxidant role in the electric field environment. The organic compound can be used to make the encapsulation layer 200 of a device, thereby playing a role in protecting the device, preventing the erosion of water and oxygen, and antioxidizing and reducing. In some embodiments, the device can be an optoelectronic device 1000, and the encapsulation layer 200 can adsorb water and oxygen, thereby protecting the various layer materials and electrodes in the optoelectronic device 1000. Moreover, due to the good electrochemical stability of the organic compound, it can prevent the oxidation or reduction of the electrodes and improve the long-term stability of the device. In addition, the organic compound structure has a mercapto group, and there is a strong force between the sulfur atom and the metal. Thus, when making the encapsulation layer 200 of the optoelectronic device 1000, the organic compound can be oriented under the induction of the chemical bond and physicochemical force between the mercapto group and the surface atoms of the electrode material - metal, thereby forming a self-assembled film layer with excellent water and oxygen resistance.

[0058] In some embodiments, in formula (I), n1 is 0 or 1. In some other embodiments, in formula (I), n2 is 0 or 1. In still some other embodiments, the sum of n1 and n2 is 1 or 2. Thus, it helps to reduce the synthesis difficulty of the organic compound.

[0059] In some embodiments, R 1 、R 2 Each time it appears, it is independently selected from one or more combinations of substituted or unsubstituted C1-C30 alkylene, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C6-C30 heteroarylene. For example, substituted or unsubstituted -C m H 2m -, substituted or unsubstituted -Ar1-, substituted or unsubstituted -Ar2-, substituted or unsubstituted -C n H 2n -Ar1-, substituted or unsubstituted -C n H 2n -Ar2- of any one, m is selected from any integer from 4 to 30, n is selected from any integer from 0 to 30, Ar1 is selected from arylene with 6 to 30 ring atoms, and Ar2 is selected from any one of heteroarylene with 6 to 30 ring atoms.

[0060] In some embodiments, in formula (I), R 1 、R 2 Each time it appears, it is independently selected from -C m H 2m -,-Ar1-,-Ar2-,-C n H 2n-Ar1-, -C n H 2n Any one of -Ar2-, and m is selected from any integer from 4 to 30, n is selected from any integer from 0 to 30, Ar1 is selected from arylene with 6 to 30 ring atoms, and Ar2 is selected from any one of heteroarylene with 6 to 30 ring atoms.

[0061] In some embodiments, in formula (I), R 1 and R 2 each independently selected from -C m H 2m -, -C n H 2n -Ar1-, -C n H 2n -Ar2- each time they appear, m is selected from any integer from 4 to 19, n is selected from any integer from 0 to 5, Ar1 is selected from arylene with 6 to 10 ring atoms, and Ar2 is selected from heteroarylene with 6 to 10 ring atoms.

[0062] In some embodiments, Ar1 is selected from phenylene or biphenylene; in some embodiments, Ar2 is selected from pyridinyl.

[0063] In some specific embodiments, the organic compound includes one or more of the compounds shown by the following formula. These organic compounds have better water and oxygen adsorption performance, self-assembly activity and electrochemical stability.

[0064]

[0065] In a second aspect, an embodiment of the present application further provides a method for preparing an organic compound, which is characterized by including the following steps:

[0066] S10, mixing compound a and an acyl chlorination reagent to carry out a first reaction to obtain intermediate N-1;

[0067] S20, mixing the intermediate N-1 and compound b to carry out a second reaction to obtain intermediate N-2;

[0068] S30, mixing the intermediate N-2 and a reducing agent to carry out a third reaction to obtain intermediate N-3;

[0069] S40, mixing the intermediate N-3 and thiourea to carry out a fourth reaction to obtain organic compound M;

[0070] Wherein, the structural formulas of the compound a, the compound b, the intermediate N-1, the intermediate N-2, the intermediate N-3 and the organic compound N are as follows:

[0071]

[0072] Among them, n1 is selected from any integer from 0 to 5, and n2 is selected from any integer from 0 to 5;

[0073] M is selected from any one of Group VIIB metal atoms and Group VIII metal atoms;

[0074] The compound a includes a compound with the general formula X 1 -R 1 -COOH and a compound with the general formula X 2 -R 2 -COOH. The intermediate N-1 includes a compound with the general formula X 1 -R 1 -COCl and a compound with the general formula X 2 -R 2 -COCl;

[0075] R 1 and R 2 each independently represent, each time they appear, one or more combinations selected from substituted or unsubstituted C1-C30 alkylene, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C2-C30 alkenylene, substituted or unsubstituted C2-C30 alkynylene, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, and substituted or unsubstituted C6-C30 heteroaryloxy;

[0076] X 1 and X 2 each independently represent, each time they appear, a halogen group.

[0077] In some embodiments, M is selected from Fe, Co, Ni, or Mn.

[0078] In some embodiments, n1 is 0 or 1; in some embodiments, n2 is 0 or 1; in some embodiments, the sum of n1 and n2 is 1 or 2.

[0079] In some embodiments, R 1 and R 2 each independently represent, each time they appear, one or more combinations selected from C4-C19 alkylene, C6-C10 arylene, and C6-C10 heteroarylene, such as -C m H 2m -, -C n H 2n -Ar1-, -C n H 2nAny one of -Ar2-, m is selected from any integer from 5 to 19, n is selected from any integer from 1 to 5, Ar1 is selected from arylene groups having 6 to 10 ring atoms, and Ar2 is selected from heteroarylene groups having 6 to 10 ring atoms.

[0080] In step S10:

[0081] In some embodiments, the acyl chloride reagent includes one or more of oxalyl chloride, thionyl chloride, and phosphorus trichloride.

[0082] In some embodiments, the temperature of the first reaction is 50°C to 90°C; for example, it can be 50°C, 60°C, 70°C, 80°C, 90°C, and values between any two of the above; controlling the temperature of the first reaction within this range can promote the reaction between compound a and the acyl chloride reagent.

[0083] In some embodiments, the time of the first reaction is 0.5 to 4 h; for example, it can be 0.5 h, 1 h, 2 h, 3 h, 4 h, and values between any two of the above.

[0084] In some embodiments, the molar ratio of compound a to the acyl chloride reagent is 1:(3 to 7); for example, it can be 1:3, 1:4, 1:5, 1:6, 1:7, and values between any two of the above.

[0085] In step S20:

[0086] In some embodiments, the molar ratio of compound b to intermediate N-1 is 1:(1 to 3); for example, it can be 1:1, 1:1.5, 1:2, 1:2.5, 1:3, and values between any two of the above.

[0087] In some embodiments, the temperature of the second reaction is 5°C to 40°C; for example, it can be 5°C, 10°C, 15°C, 20°C, 25°C, 30°C, 35°C, 40°C, and values between any two of the above; controlling the temperature of the second reaction within this range can promote the reaction between intermediate N-1 and compound b.

[0088] In some embodiments, the time of the second reaction is 4 to 10 h; for example, it can be 4 h, 5 h, 6 h, 7 h, 8 h, 9 h, 10 h, and values between any two of the above.

[0089] In step S30:

[0090] In some embodiments, the reducing agent includes zinc and mercury, and the molar ratio of the intermediate N-2, the zinc, and the mercury is 1:(40-60):(0.4-0.6); for example, it can be 1:(40-45):(0.4-0.6), 1:(40-50):(0.4-0.6), 1:(45-55):(0.4-0.6), 1:(50-60):(0.4-0.6), 1:(40-60):(0.4-0.45), 1:(40-60):(0.45-0.5), 1:(40-60):(0.5-0.55), 1:(40-60):(0.5-0.6), and so on.

[0091] In some embodiments, the temperature of the third reaction is 85°C to 100°C; for example, it can be 85°C, 90°C, 95°C, 100°C, and values between any two of the above; controlling the temperature of the third reaction within this range can promote the reduction of the intermediate N-2.

[0092] In some embodiments, the time of the third reaction is 6 to 12 h; for example, it can be 6 h, 7 h, 8 h, 9 h, 10 h, 11 h, 12 h, and values between any two of the above.

[0093] In step S40:

[0094] In some embodiments, the molar ratio of the intermediate N-3 and the thiourea is 1:(1-1.5); for example, it can be 1:1, 1:1.1, 1:1.2, 1:1.3, 1:1.4, 1:1.5, and values between any two of the above.

[0095] In some embodiments, the temperature of the fourth reaction is 60°C to 100°C; 60°C, 70°C, 80°C, 90°C, 100°C, and values between any two of the above; controlling the temperature of the fourth reaction within this range can promote the reaction between the intermediate N-3 and the thiourea.

[0096] In some embodiments, the time of the fourth reaction is 0.5 to 4 h; for example, it can be 0.5 h, 1 h, 2 h, 3 h, 4 h, and values between any two of the above.

[0097] The embodiments of the present application further provide a composition, including a solvent and a first compound, where the first compound includes the organic compound described above, or the organic compound prepared by the preparation method described above. The composition can be used as the ink for the encapsulation film layer.

[0098] In some embodiments, the solvent includes one or more of alcohol solvents; for example, it can be one or more of methanol, ethanol, n-propanol, isopropanol, n-butanol, n-pentanol, and n-hexanol.

[0099] In some embodiments, in the composition, the total concentration of the organic compound is 1 to 10 mg / ml; for example, it can be 1 mg / ml, 2 mg / ml, 3 mg / ml, 4 mg / ml, 5 mg / ml, 6 mg / ml, 7 mg / ml, 8 mg / ml, 9 mg / ml, 10 mg / ml, and values between any two of the above.

[0100] In a third aspect, an embodiment of the present application provides a thin film. The thin film is made of the above composition, or the thin film includes a second compound, and the second compound includes the organic compound described above, or the organic compound prepared by the preparation method described above. The thin film has water and oxygen resistance, antioxidant properties, and good electrochemical stability, and the thin film can be used as the encapsulation layer 200 of the device.

[0101] In some embodiments, the thickness of the thin film is 5 to 10 nm, for example, it can be 5 nm, 6 nm, 7 nm, 8 nm, 9 nm, 10 nm, and values between any two of the above.

[0102] In a fourth aspect, the present application provides an optoelectronic device 1000, which can be, for example, a quantum dot light-emitting diode (QLED), an organic light-emitting diode (OLED), etc. Please refer to Figure 1 , the optoelectronic device 1000 includes a device main body 100 and an encapsulation layer 200 provided on the surface of the device main body 100. The encapsulation layer 200 includes the thin film described above, or the material of the encapsulation layer 200 includes a second compound, and the second includes the organic compound described above, or the organic compound prepared by the preparation method described above.

[0103] The technical solution of the present application uses the above organic compound to make the encapsulation layer 200 of the optoelectronic device 1000, which can adsorb water and oxygen, thereby protecting the materials and electrodes of each layer in the optoelectronic device 1000. Moreover, since the organic compound has good electrochemical stability, it can prevent the oxidation or reduction of the electrodes, improve the long-term stability of the device, and extend the service life of the device; in addition, the organic compound structure has a mercapto group, and there is a strong force between the sulfur atom and the metal. Thus, when making the encapsulation layer 200 of the optoelectronic device 1000, the organic compound can be oriented under the induction of the chemical bond and physicochemical force between the mercapto group and the surface atoms of the electrode material - metal, thereby forming a self-assembled film layer with excellent water and oxygen resistance.

[0104] In some embodiments, the thickness of the encapsulation layer 200 is 5 to 10 nm, for example, it can be 5 nm, 6 nm, 7 nm, 8 nm, 9 nm, 10 nm, and values between any two of the above.

[0105] The device body 100 includes a first electrode and a second electrode which are oppositely arranged, and a functional layer disposed between the first electrode and the second electrode. The first electrode is one of the cathode 20 and the anode 10, and the second electrode is the other of the cathode 20 and the anode 10.

[0106] The anode 10 can be an anode 10 known in the art for the optoelectronic device 1000. For example, it can be selected from, but not limited to, a doped metal oxide particle electrode, a composite electrode of a metal and a metal oxide, a graphene electrode, a carbon nanotube electrode, a metal electrode or an alloy electrode. The material of the doped metal oxide particle electrode is selected from one or more of indium-doped tin oxide, fluorine-doped tin oxide, antimony-doped tin oxide, aluminum-doped zinc oxide, gallium-doped zinc oxide, indium-doped zinc oxide, magnesium-doped zinc oxide, and aluminum-doped magnesium oxide. The composite electrode of a metal and a metal oxide is selected from AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, TiO2 / Ag / TiO2, TiO2 / Al / TiO2, ZnS / Ag / ZnS, ZnS / Al / ZnS. The material of the metal electrode is selected from one or more of Ag, Al, Cu, Mo, Au, Pt, Si, Ca, Mg, and Ba. Herein, " / " represents a laminated structure. For example, the composite electrode AZO / Ag / AZO represents an electrode with a three-layer laminated composite structure composed of an AZO layer, an Ag layer, and an AZO layer.

[0107] The cathode 20 can be a cathode 20 known in the art for the optoelectronic device 1000. For example, it can be selected from, but not limited to, a doped metal oxide particle electrode, a composite electrode of a metal and a metal oxide, a graphene electrode, a carbon nanotube electrode, a metal electrode or an alloy electrode. The material of the doped metal oxide particle electrode is selected from one or more of indium-doped tin oxide, fluorine-doped tin oxide, antimony-doped tin oxide, aluminum-doped zinc oxide, gallium-doped zinc oxide, indium-doped zinc oxide, magnesium-doped zinc oxide, and aluminum-doped magnesium oxide. The composite electrode of a metal and a metal oxide is selected from AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, TiO2 / Ag / TiO2, TiO2 / Al / TiO2, ZnS / Ag / ZnS, ZnS / Al / ZnS. The material of the metal electrode is selected from one or more of Ag, Al, Cu, Mo, Au, Pt, Si, Ca, Mg, and Ba.

[0108] It can be understood that the optoelectronic device 1000 can be a normal device or an inverted device. One of the first electrode and the second electrode is a top electrode, and the top electrode is in contact with the encapsulation layer 200. In some embodiments, the material of the top electrode includes metal atoms. For example, the top electrode is a doped metal oxide particle electrode, a composite electrode of metal and metal oxide, a metal electrode or an alloy electrode. In this way, the sulfhydryl group in the organic compound contained in the encapsulation layer 200 is connected to the metal atoms, which on the one hand helps to strengthen the connection between the encapsulation layer 200 and the electrode, and on the other hand can play a role in inducing the directional arrangement of the organic compound, which helps to enhance the encapsulation performance of the encapsulation layer 200. In some embodiments, the encapsulation layer 200 is a self-assembled film.

[0109] In some embodiments, the functional layer includes a light-emitting layer 30, and the light-emitting layer 30 can be an organic light-emitting layer 30 or a quantum dot light-emitting layer 30. When the light-emitting layer 30 is an organic light-emitting layer 30, the optoelectronic device 1000 can be an organic light-emitting device; when the light-emitting layer 30 is a quantum dot light-emitting layer 30, the optoelectronic device 1000 can be a quantum dot light-emitting device.

[0110] The material of the organic light-emitting layer 30 is a material known in the art for the organic light-emitting layer 30 of the optoelectronic device 1000. For example, it can be selected from, but not limited to, 4,4'-bis(N-carbazolyl)-1,1'-biphenyl: tris[2-(p-tolyl)pyridineiridium(III), 4,4',4”-tris(carbazol-9-yl)triphenylamine: tris[2-(p-tolyl)pyridineiridium, diarylanthracene derivatives, stilbene aromatic derivatives, pyrene derivatives, fluorene derivatives, TBPe fluorescent materials, TTPX fluorescent materials, TBRb fluorescent materials, DBP fluorescent materials, delayed fluorescent materials, TTA materials, thermally activated delayed materials, polymers containing B-N covalent bonds, hybrid local charge transfer excited state materials, exciplex luminescent materials, or one or more of them.

[0111] The material of the quantum dot light-emitting layer 30 is a quantum dot material known in the art for use in optoelectronic devices 1000. For example, it can be selected from, but not limited to, at least one of single-structure quantum dots, core-shell structure quantum dots, and perovskite semiconductor materials; the materials of the single-structure quantum dots, the core materials of the core-shell structure quantum dots, and the shell materials of the core-shell structure quantum dots are respectively selected from at least one of II-VI group compounds, IV-VI group compounds, III-V group compounds, and I-III-VI group compounds; the II-VI group compounds are selected from at least one of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and HgZnSTe; the IV-VI group compounds are selected from at least one of SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, and SnPbSTe; the III-V group compounds are selected from at least one of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and InAlPSb; the I-III-VI group compounds are selected from at least one of CuInS2, CuInSe2, and AgInS2.

[0112] As an example, the quantum dots of the core-shell structure may be selected from but not limited to at least one of CdZnSe / CdZnSe / ZnSe / CdZnS / ZnS, CdZnSe / CdZnSe / CdZnS / ZnSCdSe / CdSeS / CdS, InP / ZnSeS / ZnS, CdZnSe / ZnSe / ZnS, CdSeS / ZnSeS / ZnS, CdSe / ZnS, CdSe / ZnSe / ZnS, ZnSe / ZnS, ZnSeTe / ZnS, CdSe / CdZnSeS / ZnS, and InP / ZnSe / ZnS.

[0113] It should be noted that for the materials of the aforementioned single-structure quantum dots, or the core materials of the core-shell structure quantum dots, or the shell materials of the core-shell structure quantum dots, the chemical formulas provided only indicate the elemental composition and do not indicate the content of each element. For example, CdZnSe only indicates that it is composed of three elements, Cd, Zn, and Se. If the content of each element is to be expressed, it corresponds to Cd x Zn 1-x Se, where 0 < x < 1.

[0114] The perovskite semiconductor material may be selected from but not limited to doped or undoped inorganic perovskite semiconductors, or organic-inorganic hybrid perovskite semiconductors; the general structural formula of the inorganic perovskite semiconductor is AMX3, where A is a Cs + ion, M is a divalent metal cation selected from Pb 2+ , Sn 2+ , Cu 2+ , Ni 2+ , Cd 2+ , Cr 2+ , Mn 2+ , Co 2+ , Fe 2+ , Ge 2+ , Yb 2+ , Eu 2+ and at least one of them, X is a halogen anion selected from at least one of Cl−, Br - , I−; the general structural formula of the organic-inorganic hybrid perovskite semiconductor is BMX3, where B is an organic amine cation selected from CH3(CH2) n-2 NH3 + or [NH3(CH2) n NH3] 2+ , where n ≥ 2, M is a divalent metal cation selected from Pb 2+ , Sn 2+ , Cu 2+ , Ni 2+ , Cd 2+ , Cr2+ 、Mn 2+ 、Co 2+ 、Fe 2+ 、Ge 2+ 、Yb 2+ 、Eu 2+ at least one of, X is a halogen anion, selected from Cl - 、Br - 、I - at least one of.

[0115] Fifthly, the embodiment of the present application also provides a method for preparing an optoelectronic device 1000, including the following steps:

[0116] S100, providing a device body 100 and a thin film material;

[0117] S200, disposing the thin film material on the device body 100 to form a packaging layer 200, obtaining the optoelectronic device 1000;

[0118] Wherein, the thin film material includes at least one organic compound, and the organic compound includes the organic compound described above, or is prepared by the preparation method described above.

[0119] In some embodiments, the thin film material further includes a solvent. The solvent includes one or more of alcohol solvents; for example, it can be one or more of methanol, ethanol, n-propanol, isopropanol, n-butanol, n-pentanol, and n-hexanol.

[0120] In some embodiments, in the thin film material, the total concentration of the organic compound is 1-10 mg / ml; for example, it can be 1 mg / ml, 2 mg / ml, 3 mg / ml, 4 mg / ml, 5 mg / ml, 6 mg / ml, 7 mg / ml, 8 mg / ml, 9 mg / ml, 10 mg / ml, and values between any two of the above.

[0121] In some embodiments, the step of disposing the thin film material on the device body 100 to form a packaging layer 200 includes: immersing the device body 100 in the thin film material, taking it out after standing still, and performing annealing treatment to obtain the packaging layer 200. The device body 100 has a processing side for setting the packaging layer 200. In actual operation, only the processing side of the device body 100 can be immersed in the thin film material.

[0122] In some embodiments, the standing time is 0.5-2 h; for example, it can be 0.5 h, 1 h, 1.5 h, 2 h, and values between any two of the above.

[0123] In some embodiments, the annealing temperature is 100°C to 150°C; for example, it can be 100°C, 110°C, 120°C, 130°C, 140°C, 150°C, and values between any two of the above.

[0124] In some embodiments, the annealing time is 10 to 30 minutes; for example, it can be 10 minutes, 15 minutes, 20 minutes, 25 minutes, 30 minutes, and values between any two of the above.

[0125] In some embodiments, step S200 can be carried out in an environment where both the oxygen content and the water content are lower than 0.1 ppm. Thus, it helps to improve the stability of the optoelectronic device 1000.

[0126] In some embodiments, the method for preparing the device body 100 includes the following steps: preparing a plurality of film layers in a preset film layer sequence to obtain the optoelectronic device 1000; wherein, the plurality of film layers include an anode 10, a cathode 20, and a functional layer disposed between the anode 10 and the cathode 20. The preset film layer sequence refers to the order in which the optoelectronic device 1000 is stacked layer by layer from bottom to top.

[0127] In the optoelectronic device 1000 provided in the present application, conventional preparation methods can also be used for the functional layer, the anode 10, and the cathode 20. Specifically, the conventional preparation method can be a chemical method or a physical method. Among them, the chemical method includes chemical vapor deposition, sequential ionic layer adsorption and reaction, anodic oxidation, electrodeposition, and coprecipitation. The physical method includes physical coating and solution methods. Among them, the physical coating method includes: thermal evaporation coating, electron beam evaporation coating, magnetron sputtering, multi-arc ion coating, physical vapor deposition, atomic layer deposition, pulsed laser deposition, etc.; the solution method can be spin coating, printing, inkjet printing, doctor blade coating, printing, dip coating, immersion, spraying, roll coating, casting, slot die coating, and bar coating, etc.

[0128] In addition, the present application also relates to a display device, which includes the above-mentioned optoelectronic device 1000, or an optoelectronic device 1000 prepared by the above preparation method. The display device can be any electronic product with a display function. The electronic product includes but is not limited to a smart phone, a tablet computer, a notebook computer, a digital camera, a digital video camera, a smart wearable device, a smart weighing scale, a vehicle-mounted display, a television, or an e-book reader. Among them, the smart wearable device can be, for example, a smart bracelet, a smart watch, a virtual reality (VR) helmet, etc.

[0129] The present application will be specifically described below through specific embodiments. The following embodiments are only partial embodiments of the present application and do not limit the present application. The raw materials used in the following embodiments are all commercially available products unless otherwise specified.

[0130] Material Example 1

[0131] (1) This embodiment provides an organic compound M1, and the organic compound M1 has the following structural formula, and its CAS number is 134029-92-8.

[0132]

[0133] (2) Disperse the organic compound M1 in step (1) in ethanol to make a mixed solution with a concentration of M1 of 5 mg / ml. Immerse the glass substrate in the mixed solution, take it out after 1.5 h, and perform high-temperature drying treatment at 120 °C for 30 min to obtain a substrate with a packaging film (thickness: 6 nm) on the surface.

[0134] Material Example 2

[0135] This material example is basically the same as Material Example 1, except that in this material example, the organic compound M1 is changed to an organic compound M2, and the organic compound M2 has the following structural formula, and its CAS number is 127087-36-9.

[0136]

[0137] Except for this, other parameters and conditions remain unchanged.

[0138] Material Example 3

[0139] This material example is basically the same as Material Example 1, except that in this material example, the organic compound M1 is changed to an organic compound M3, and the organic compound M3 has the following structural formula:

[0140]

[0141] The synthesis route of the organic compound M3 is as follows:

[0142]

[0143] While stirring, slowly drop 20 mL of thionyl chloride solution into 7.2 g of compound 3-1 (CAS No. 2536-38-1), heat it to 60 °C in an oil bath and reflux for 2 h. When no more HCl gas is generated, distill out all the excess thionyl chloride to obtain the product compound 3-2.

[0144] 3.87 g of ferrocene was added to 60 mL of carbon disulfide solution. While stirring, the compound 3-2 obtained in the previous step was added, and the mixture was cooled in an ice bath. Separately, 5.05 g of anhydrous aluminum trichloride was added in portions, and the temperature of the solution was maintained at 5-10 °C. After addition, the ice bath was removed, and the reaction mixture was warmed to room temperature and stirred for 5 h to obtain a dark brown reaction solution. The reaction solution was poured into a mixture of 100 g of crushed ice and 15 mL of concentrated hydrochloric acid. The aqueous layer was separated, and then extracted 4 times with 50 mL of dichloromethane each time. The organic layers were combined, washed successively with hydrochloric acid, water, and saturated brine, and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and the solvent was removed by rotary evaporation to obtain a black crude product. The crude product was purified using a silica gel chromatography column to obtain a red-brown solid compound 3-3 with a yield of 62%.

[0145] 0.56 g of mercuric chloride and concentrated hydrochloric acid (0.56 mL) were dissolved in water (16.8 mL). Then, zinc powder (13.5 g) was added to this solution in portions, and the mixture was vigorously stirred for 10 min and then allowed to stand for precipitation. The supernatant was carefully decanted to obtain zinc amalgam, which was immediately used in the next experiment. 8 mL of concentrated hydrochloric acid was added to the zinc amalgam obtained above, and the mixture was heated to 100 °C in an oil bath. While maintaining gentle boiling, 5 g of compound 3-3 was added, and the mixture was heated under reflux with stirring for 8 h. After cooling to room temperature, the zinc amalgam precipitated, and the upper layer solution separated into two layers. The upper layer liquid was carefully decanted. The aqueous layer was extracted 3 times with 30 mL of ethyl acetate each time. All the organic layers were combined and washed successively with 5% sodium carbonate solution, water, and saturated brine to obtain the washed product. The washed product was dried over anhydrous sodium sulfate, and the solvent was removed by evaporation to obtain a bright yellow oil. Finally, the compound 3-4 was obtained by purification using a silica gel column chromatography with a yield of 42%.

[0146] A suspension of 27.5 mL of ethanol and 0.363 g of thiourea was heated to reflux at 80 °C on an oil bath, and the solution gradually became clear. Heating was stopped, and 2.6 g of compound 3-4 was added all at once and stirring was continued for 2 h. After cooling to room temperature, the precipitate formed was collected using a Buchner funnel and washed with a small amount of 95% ethanol. It was dried under an infrared lamp to obtain intermediate diisothiouronium bromide. Under nitrogen protection, the purified intermediate diisothiouronium bromide was dissolved in 20 mL of a 40% sodium hydroxide solution. This mixture was heated under reflux until a large amount of oil formed on the surface of the solution. Heating was then stopped, and the mixture was cooled to room temperature. The pH value was slowly adjusted to turn Congo red test paper red using approximately 20 mL of concentrated hydrochloric acid, and an additional 2 mL of concentrated hydrochloric acid was added. The aqueous layer was extracted 3 times with 30 mL of dichloromethane each time. The organic phases were combined and washed successively with 10 mL of water and 10 mL of saturated brine. The washed product was dried over anhydrous sodium sulfate, the desiccant was filtered off, and the solvent was removed by rotary evaporation to obtain a yellow-brown crude product. The crude product obtained was purified using a silica gel chromatography column, and finally M3 was obtained with a yield of 41%.

[0147] 1 1H NMR (CDCl3, 6): 4.20 (br, 5H), 3.92 - 4.05 (m, 4H), 2.18 (t, 2H), 2.52 (m, 2H), 1.20 - 1.50 (m, 33H).

[0148] Material Example 4

[0149] This material example is basically the same as Material Example 1, except that in this material example, organic compound M1 is changed to organic compound M4, and the organic compound M4 has the following structural formula:

[0150]

[0151] The synthetic route of the organic compound M4 is basically the same as that of the organic compound M3, except that the raw material compound 3 - 1 is changed to compound 4 - 1 (CAS: 73367 - 80 - 3).

[0152] 1 1H NMR (CDCl3, 6): 3.92 - 4.05 (m, 8H), 2.64 (m, 4H), 2.53 (m, 4H), 1.20 - 1.50 (m, 42H).

[0153] Material Example 5

[0154] This material example is basically the same as Material Example 1, except that in this material example, organic compound M1 is changed to organic compound M5, and the organic compound M5 has the following structural formula:

[0155]

[0156]

[0157] The synthetic route of the organic compound M5 is basically the same as that of the organic compound M3, except that the raw material compound 3 - 1 is changed to compound 5 - 1, and the compound 5 - 1 is p - bromobenzoic acid (CAS: 586 - 76 - 5).

[0158] 1 1H NMR (CDCl3, 6): 7.36 (d, 2H), 7.28 (d, 2H), 4.20 (br, 5H), 3.92 - 4.05 (m, 4H), 3.40 (s, 1H), 3.22 (s, 2H).

[0159] Material Example 6

[0160] This material example is basically the same as Material Example 1, except that in this material example, organic compound M1 is changed to organic compound M6, and the organic compound M6 has the following structural formula:

[0161]

[0162] The synthesis route of the organic compound M6 is basically the same as that of the organic compound M3, except that the raw material compound 3-1 is changed to compound 6-1, and the compound 6-1 is 4'-bromo[1,1'-biphenyl]-4-carboxylic acid (CAS: 5731-11-3).

[0163] 1 H NMR(CDCl3,6): 7.63(d,2H),7.61(d,2H),7.55(d,2H),7.38(d,2H),4.20(br,5H),3.92 - 4.05(m,4H),3.40(s,1H),3.22(s,2H).

[0164] Material Example 7

[0165] This material example is basically the same as Material Example 1, except that in this material example, organic compound M1 is changed to organic compound M7, and the organic compound M7 has the following structural formula:

[0166]

[0167] The synthesis route of the organic compound M7 is basically the same as that of the organic compound M6, except that the dosage of compound 6-2 is doubled and aluminum trichloride is doubled.

[0168] 1 H NMR(CDCl3,6): 7.63(d,4H),7.61(d,4H),7.55(d,4H),7.38(d,4H),3.92 - 4.05(m,8H),3.40(s,2H), 3.22(s,4H).

[0169] Material Example 8

[0170] This material example is basically the same as Material Example 1, except that in this material example, organic compound M1 is changed to organic compound M8, and the organic compound M8 has the following structural formula:

[0171]

[0172] The synthesis route of the organic compound M8 is as follows:

[0173]

[0174] The synthetic route of the organic compound M8 is basically the same as that of the organic compound M3, except that the starting compound 3-1 is changed to the compound 8-1, and the compound 8-1 is 5-bromo-2-pyridinecarboxylic acid (CAS: 30766-11-1).

[0175] 1 H NMR(CDCl3,6): 8.59(s,1H), 7.40(d,1H), 6.99(d,1H) 4.20(br,5H), 3.92 - 4.05(m,4H), 3.55(s,2H), 3.40(s,1H).

[0176] Device Example 1

[0177] This device example provides a quantum dot light-emitting diode and its preparation method, which specifically includes the following steps.

[0178] Step 1: After cleaning and drying the anode substrate, it is treated in an ultraviolet ozone cleaner for 15 min and set aside. Spin-coat the PEDOT:PSS solution on the anode substrate at a speed of 5000 rpm for 30 s, and then heat it at 230 °C for 15 min to obtain a hole injection layer. Spin-coat the chlorobenzene solution of TFB (concentration: 10 mg / mL) on the hole injection layer at a speed of 2500 rpm, and then heat it at 200 °C for 30 min to obtain a hole transport layer. Spin-coat the quantum dot solution (concentration: 40 mg / ml) on the hole transport layer at a speed of 1500 rpm, and then heat it at 100 °C for 5 min to obtain a light-emitting layer. Spin-coat the ethanol solution of ZnO (concentration: 40 mg / ml) on the light-emitting layer at a speed of 3000 rpm, and then heat it at 100 °C for 15 min to obtain an electron transport layer. Evaporate Ag in vacuum on the electron transport layer to obtain a cathode. A QLED device body is obtained, and the structure of the device body is ITO / PEDOT:PSS / TFB / QD / ZnO / Ag.

[0179] Step 2: Take the mixed solution in Material Example 1, immerse the device body into the mixed solution, take it out after standing for 1.5 h, and perform a high-temperature drying treatment at 120 °C for 30 min to obtain a QLED device with a packaging layer on its surface.

[0180] Device Examples 2 to 8

[0181] Device Example n is basically the same as Device Example 1, except that in Device Example n: in Step 2, the mixed solution in Example n is used to make the packaging layer, and n is any integer from 2 to 8. Other parameters and steps remain unchanged.

[0182] Device Comparative Example 1

[0183] The comparative example of this device is basically the same as Example 1 of the device, except that the QLED proposed in the comparative example of this device does not have a packaging layer. Correspondingly, in the preparation steps, step 2 is omitted. Except for this, other parameters and steps remain unchanged.

[0184] Comparative Example 2 of the device

[0185] The comparative example of this device is basically the same as Example 1 of the device, except that in the comparative example of this device, a polysulfide rubber is used to make the packaging layer.

[0186] Experimental example

[0187] (1) Perform performance tests on the encapsulation film prepared in step (2) of the material example. The results are recorded in Table 1, and polysulfide rubber is used as the control group. The test items and detection methods are as follows:

[0188] The water vapor barrier ability of the film is characterized by the water vapor transmission rate (GB / T 1037). Under the conditions of 38 °C / 90RH, measure the mass of water vapor passing through the film per unit area, and the unit is g / m 2 ·24h; The oxygen barrier performance is characterized by the oxygen transmission rate (GB / T 1038). Measure the volume of oxygen passing through the sample within 24 hours, and the unit is ml / m2·24h.

[0189] Table 1

[0190]

[0191]

[0192] As can be seen from the above table, compared with polysulfide rubber, the encapsulation films of each example have significantly lower water vapor transmission rates and oxygen transmission rates, indicating that the films prepared from the organic compounds of this application have a better effect of adsorbing water and oxygen.

[0193] (2) Perform stability tests on the QLEDs of the device examples and device comparative examples for the lifetime T95@1000nit. The test results are shown in Table 2.

[0194] The test method for the lifetime T95@1000nit is as follows:

[0195] When the device is driven by a constant current or voltage, the time required for the brightness to decrease to a certain proportion of the maximum brightness. The time when the brightness drops to 95% of the maximum brightness is defined as T95, and this lifetime is the measured lifetime. To shorten the test cycle, the device lifetime test is usually carried out by accelerating the device aging at high brightness, and the lifetime at high brightness is obtained by fitting with an extended exponential decay brightness decay fitting formula. For example, the lifetime at 1000 nit is denoted as T95@1000nit. The specific calculation formula is as follows:

[0196]

[0197] Among them, T95 L is the lifespan at low brightness, and T95 H is the measured lifespan at high brightness. L H is the device accelerated to the highest brightness. L L is 1000 nit, A is the acceleration factor. In this experiment, the value of A is obtained as 1.7 by measuring the lifespans of several groups of QLED devices at the rated brightness.

[0198] The test method for the stability of the lifespan T95@1000 nit is as follows: Detect the lifespan T95@1000 nit in an environment with a humidity of 60%, denoted as A1; Detect the lifespan T95@1000 nit in an environment with a humidity of 90%, denoted as A2; The change rate = (A1 - A2) / A1 × 100%.

[0199] Table 2

[0200]

[0201]

[0202] As can be seen from the above table, compared with the device comparative examples 1 and 2, the devices prepared in each device example not only have a higher T95@1000 nit, but also have a lower lifespan change rate, indicating that using the encapsulation layer of the organic compound of the present application can effectively adsorb water and oxygen, resist oxidation, play a role in extending the service life of the device and improving the performance stability of the device.

[0203] The technical solutions provided by the embodiments of the present application have been introduced in detail above. Specific examples are used in this article to elaborate on the principle and implementation manner of the present application. The description of the above embodiments is only used to help understand the method and its core idea of the present application; at the same time, for those skilled in the art, according to the idea of the present application, there will be changes in the specific implementation manner and application scope. In summary, the content of this specification should not be construed as a limitation to the present application.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in formula (I): Wherein, n1 is selected from any integer from 0 to 5, and n2 is selected from any integer from 0 to 5; M is selected from any one of Group VIIB metal atoms and Group VIII metal atoms; R 1 , R 2 Each occurrence is independently selected from one or more combinations of: substituted or unsubstituted C1-C30 alkylene, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C2-C30 alkenylene, substituted or unsubstituted C2-C30 alkynylene, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, and substituted or unsubstituted C6-C30 heteroaryloxy.

2. The organic compound according to claim 1, characterized in that, M is selected from Fe, Co, Ni or Mn; and / or, In the substituted C1-C30 alkylene group, substituted C6-C30 arylene group, C6-C30 heteroarylene group, substituted C2-C30 alkenylene group, substituted C2-C30 alkynylene group, substituted C1-C30 alkoxy group, substituted C6-C30 aryloxy group, substituted C6-C30 heteroaryloxy group, the substituents are selected from any one or more of C1-C10 alkyl group, C1-C10 alkoxy group, C2-C10 alkoxycarbonyl group, C2-C10 alkylcarbonyl group, C6-C30 aryl group, cyano group, nitro group, mercapto group, hydroxyl group, carboxyl group, amino group, halogen group.

3. The organic compound according to claim 1 or 2, characterized in that, n1 is 0 or 1; and / or, n2 is 0 or 1; and / or, n1 and n2 are not both 0 at the same time; and / or, R 1 、R 2 Each occurrence is independently selected from one or more combinations of C1-C30 alkylene, C6-C30 arylene, and C6-C30 heteroarylene.

4. The organic compound according to claim 3, characterized in that, R 1 、R 2 Each occurrence is independently selected from one or more combinations of C4-C19 alkylene, C6-C10 arylene, and C6-C10 heteroarylene.

5. The organic compound according to any one of claims 1 to 4, characterized in that, The organic compound includes one or more of the compounds shown in the following formula:

6. A method for preparing an organic compound, characterized in that, Comprising the following steps: Mix compound a and an acyl chlorination reagent, carry out a first reaction to obtain intermediate N-1; Mix the intermediate N-1 and compound b, carry out a second reaction to obtain intermediate N-2; Mix the intermediate N-2 and a reducing agent, carry out a third reaction to obtain intermediate N-3; Mix the intermediate N-3 and thiourea, carry out a fourth reaction to obtain organic compound M; Wherein, the structural formulas of the compound a, the compound b, the intermediate N-1, the intermediate N-2, the intermediate N-3 and the organic compound N are shown as follows: Wherein, n1 is selected from any integer from 0 to 5, and n2 is selected from any integer from 0 to 5; M is selected from any one of Group VIIB metal atoms and Group VIII metal atoms; The compound a includes compounds with the general formula X 1 -R 1 -COOH and compounds with the general formula X 2 -R 2 -COOH. The intermediate N-1 includes compounds with the general formula X 1 -R 1 -COCl and compounds with the general formula X 2 -R 2 -COCl; R 1 and R 2 each independently selected from one or more combinations of: substituted or unsubstituted C1-C30 alkylene, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C2-C30 alkenylene, substituted or unsubstituted C2-C30 alkynylene, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, and substituted or unsubstituted C6-C30 heteroaryloxy each time they appear; X 1 and X 2 each independently selected from halogen groups each time they appear.

7. According to the preparation method described in claim 6, characterized in that, The acyl chlorination reagent includes one or more of oxalyl chloride, thionyl chloride, phosphorus trichloride; and / or, The temperature of the first reaction is 50°C to 90°C; and / or, The time of the first reaction is 0.5 to 4 h; and / or, The temperature of the second reaction is 5°C to 40°C; and / or, The time of the second reaction is 4 to 10 h; and / or, The reducing agent includes zinc and mercury; and / or, The temperature of the third reaction is 85°C to 100°C; and / or, The time of the third reaction is 6 to 12 h; and / or, The temperature of the fourth reaction is 60°C to 100°C; and / or, The time of the fourth reaction is 0.5 to 4 h; and / or, M is selected from Fe, Co, Ni or Mn; and / or, n1 is 0 or 1; and / or, n2 is 0 or 1; and / or, The sum of n1 and n2 is 1 or 2; and / or, R 1 and R 2 each independently selected from one or more combinations of C4-C19 alkylene, C6-C10 arylene, and C6-C10 heteroarylene each time it appears.

8. A composition, characterized in that, Comprising a solvent and a first compound, the first compound includes the organic compound according to any one of claims 1 to 5, or the organic compound prepared by the preparation method according to claim 6 or 7.

9. The composition according to claim 8, characterized in that, The solvent includes one or more of alcohol solvents; and / or, In the composition, the total concentration of the organic compound is 1 to 10 mg / ml.

10. A thin film, characterized in that, The thin film is prepared from the composition according to Claim 8 or 9, or the material of the thin film comprises a second compound, the second compound comprises the organic compound according to any one of Claims 1 to 5, or the organic compound prepared by the preparation method according to Claim 6 or 7.

11. The thin film according to claim 10, characterized in that, The thickness of the thin film is 5 to 10 nm.

12. An optoelectronic device, characterized in that, It includes a device body and a packaging layer disposed on the surface of the device body, and the packaging layer comprises the thin film according to Claim 10 or 11.

13. The optoelectronic device according to claim 12, characterized in that, The device body comprises an electrode, the packaging layer contains a mercapto group, the electrode contains a metal atom, and the mercapto group is connected to the metal atom; and / or, The packaging layer is a self-assembled film.

14. A method for preparing an optoelectronic device, characterized in that, It includes the following steps: Providing a device body and a thin film material; Disposing the thin film material on the device body to form a packaging layer to obtain an optoelectronic device; Wherein, the thin film material comprises the composition, or comprises a second compound, the second compound comprises the organic compound according to any one of Claims 1 to 5, or the organic compound prepared by the preparation method according to Claim 6 or 7.

15. The preparation method according to claim 14, characterized in that, The thin film material further comprises a solvent; The solvent comprises one or more of alcohol solvents; and / or, In the thin film material, the total concentration of the organic compound is 1 to 10 mg / ml; and / or, The step of disposing the thin film material on the device body to form a packaging layer includes: immersing the device body in the thin film material, taking it out after standing, and performing annealing treatment to obtain the packaging layer.

16. The preparation method according to claim 15, characterized in that, The standing time is 0.5 to 2 h; and / or, The annealing temperature is 100 °C to 150 °C; and / or, The annealing time is 10 to 30 min.

17. A display device, characterized in that, It includes an optoelectronic device, the optoelectronic device comprises the optoelectronic device according to Claim 12 or 13, or is prepared by the preparation method according to any one of Claims 14 to 16.

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