Organic compound, composition and optoelectronic device

Abstract

The invention discloses an organic compound, a composition and a photoelectric device. The organic compound takes a fluorenone structure as a core skeleton and has a benzotriazole structural unit.

Description

Technical Field

[0001] The present application relates to the technical field of organic materials, and specifically relates to an organic compound, a composition, and an optoelectronic device. Background Art

[0002] Hole functional materials refer to materials with hole transport performance or hole injection performance, including but not limited to poly(N-vinylcarbazole) (PVK), 4,4'-N,N'-dicarbazolyl-biphenyl (CBP), etc. However, with the increasingly in-depth research and development of hole functional materials, the existing types of materials are gradually difficult to meet the requirements of more and more application scenarios. Therefore, it is urgent to develop new hole functional materials to expand the types of hole functional materials. Summary of the Invention

[0003] Aiming at the deficiencies of the prior art, the present application provides an organic compound, a composition, and an optoelectronic device.

[0004] In a first aspect, the present application provides an organic compound having a structure represented by the following general formula (I):

[0005]

[0006] In the general formula (I), are each independently selected from & represents the fusion site with ;

[0007] are each independently absent or selected from and at least one of them is present, and * represents the connection site with R1 or R2;

[0008] R1 and R2 are each independently absent or independently selected from groups having structures represented by the following formula (2-1) or formula (2-2):

[0009]

[0010] In formula (2-1), X is selected from O, S, SiR5R6, CR7R8, or NR9, and R5 to R9 are each independently selected from -H, -D, -NR 10 R 11 , a halogen group, a hydroxyl group, a mercapto group, a nitro group, a sulfonic acid group, an aldehyde group, a cyano group, an unsubstituted or at least one substituent-substituted C1-C30 linear alkyl group, an unsubstituted or at least one substituent-substituted C1-C30 linear alkoxy group, an unsubstituted or at least one substituent-substituted aryl group having 6 to 30 ring atoms, or an unsubstituted or at least one substituent-substituted heteroaryl group having 5 to 30 ring atoms, or a combination of these groups;

[0011] In formula (2-2), Y-* is selected from N-* or N-R 12 -*, R 12 is selected from a linear alkylene group having 1 to 30 carbon atoms, a linear alkoxy group having 1 to 30 carbon atoms, an arylene group having 6 to 14 ring atoms, or a heteroarylene group having 5 to 14 ring atoms, or a combination of these groups;

[0012] R3 and R4 are each independently selected from a single bond, -H, -D, a hydroxyl group, a mercapto group, -NR 10 R 11 , an unsubstituted or at least one substituent-substituted linear alkyl group having 1 to 30 carbon atoms, or an unsubstituted or at least one substituent-substituted linear alkoxy group having 1 to 30 carbon atoms, or a combination of these groups, and adjacent R3 and R4 are not connected, or adjacent R3 and R4 are connected to form a cyclic structure with X or Y;

[0013] R 10 and R 11 each occurrence is independently selected from -H, -D, a linear alkyl group having 1 to 30 carbon atoms, a linear alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 14 ring atoms;

[0014] The substituent is each occurrence independently selected from -D, a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms, or an aryl group having 6 to 14 ring atoms;

[0015] n1 and n2 are each independently selected from integers from 0 to 5.

[0016] In a second aspect, the present application provides a method for preparing an organic compound for preparing the organic compound as described in the first aspect, and the method for preparing the organic compound includes the following steps:

[0017] (A1) Using a first compound as a raw material, performing a ring-closure reaction to obtain a second compound; and

[0018] (A2) Mixing the second compound with a third compound and performing a nitrogen-nitrogen coupling reaction to obtain an organic compound having the structure shown in general formula (I);

[0019] wherein, the first compound has the structure shown in the following formula (4-1):

[0020]

[0021] The second compound has the structure shown in the following formula (4-2):

[0022]

[0023] The general formula of the third compound is Ar-Z, where Ar represents R1 or R2. When the atom in Ar connected to Z is an N atom, Z is -H; when the atom in Ar connected to Z is a non-N atom, Z is a halogen group.

[0024] In a third aspect, the present application provides a composition, which includes a solvent and an organic compound as described in the first aspect or an organic compound prepared by the preparation method as described in the second aspect.

[0025] In a fourth aspect, the present application provides an optoelectronic device, including:

[0026] An anode and a cathode disposed opposite to each other; and

[0027] A functional layer disposed between the anode and the cathode;

[0028] Wherein, the functional layer includes a hole functional layer, and the material of the hole functional layer includes the organic compound as described in the first aspect or an organic compound prepared by the preparation method as described in the second aspect, or the hole functional layer is prepared from the composition as described in the third aspect.

[0029] The present application provides an organic compound, a composition and an optoelectronic device, having the following technical effects:

[0030] The organic compound provided by the present application uses a fluorenone structure as the core skeleton and has a benzotriazole structural unit, and can be used as a hole injection material or a hole transport material. Description of the Drawings

[0031] The following will combine the drawings and describe the specific embodiments of the present application in detail, making the technical solutions and other beneficial effects of the present application obvious.

[0032] Figure 1 It is a schematic flow chart of a preparation method of a compound provided by an embodiment of the present application.

[0033] Figure 2 It is a schematic structural diagram of an optoelectronic device provided by an embodiment of the present application.

[0034] The reference numerals are as follows:

[0035] 10: Optoelectronic device, 101: Anode, 102: Cathode, 103: Functional layer, 1031: Electron functional layer, 1032: Hole functional layer, 1033: Light-emitting layer, 10321: Hole injection layer, 10322: Hole transport layer. Detailed Embodiments

[0036] The technical solutions in the embodiments of the present application will be clearly and completely described below 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. All other embodiments obtained by those skilled in the art based on the embodiments in the present application without creative efforts shall fall within the protection scope of the present application.

[0037] Unless otherwise defined, all professional and scientific terms used herein have the same meaning as those familiar to those skilled in the art. In addition, any methods and materials similar or equivalent to the described content can be applied to the present invention. The preferred methods and materials described herein are only for illustrative purposes and do not limit the content of the present application.

[0038] It should be noted that the description order of the following embodiments does not limit the preferred order of the embodiments. The various embodiments of the present application can exist in a range form. It should be understood that the description in a range form is only for convenience and brevity and should not be construed as a rigid limitation on the scope of the present invention; therefore, it should be considered that the described range description has specifically disclosed all possible sub-ranges and individual values within that range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., and individual numbers within the counted range, such as 1, 2, 3, 4, 5, and 6, and this applies regardless of the range. Additionally, whenever a numerical range is indicated herein, it means including any cited number (fraction or integer) within the indicated range.

[0039] In the present application, unless otherwise stated, the orientation terms such as "upper" and "lower" generally refer to the upper and lower in the actual use or working state of the optoelectronic device, specifically the drawing direction in the accompanying drawings; and "inner" and "outer" refer to the outline of the optoelectronic device. Terms such as first, second, and third are only used as labels and do not impose numerical requirements or establish an order.

[0040] In this application, descriptions such as "Layer A is formed on one side of Layer B", "Layer A is formed on the side of Layer B away from Layer C", or similar descriptions can mean that Layer A is directly formed on one side of Layer B or on the side of Layer B away from Layer C, that is, Layer A is in direct contact with Layer B, or it can mean that Layer A is indirectly formed on one side of Layer B or on the side of Layer B away from Layer C, that is, other spacer structure layers may be formed between Layer A and Layer B. Similarly, "Layer A is disposed on one side of Layer B", "Layer A is disposed on the side of Layer B away from Layer C" can mean that Layer A is in direct contact with Layer B, or it can mean that other spacer structure layers are provided between Layer A and Layer B; "Layer A is disposed between Layer B and Layer C" can mean that Layer A is in direct contact with Layer B and Layer A is in direct contact with Layer C, or Layer A is in direct contact with Layer B and one or more spacer structure layers are provided between Layer A and Layer C, or one or more spacer structure layers are provided between Layer A and Layer B and one or more spacer structure layers are provided between Layer A and Layer C, or one or more spacer structure layers are provided between Layer A and Layer B and Layer A is in direct contact with Layer C.

[0041] The term "comprising" means "including but not limited to". The term "and / or" is used to describe the relationship between associated objects and indicates that three relationships can exist. For example, A and / or B can mean: A exists alone, A and B exist simultaneously, or B exists alone. Wherein A and B can be singular or plural. The term "at least one (piece)" means one (piece) or more than one (piece), and "more than one (piece)" means two (pieces) or more than two (pieces). The term "at least one (piece)", "at least one (piece) below", or similar expressions refer to any combination of these items, including any combination of a single (piece) or multiple (pieces). For example, "at least one (piece) of a, b, or c" or "at least one (piece) of a, b, and c" can both be expressed as: a, b, c, a - b (i.e., a and b), a - c, b - c, or a - b - c, where a, b, and c can each be a single (piece) or multiple (pieces).

[0042] The term "chain alkyl" refers to an aliphatic straight-chain hydrocarbon group or an aliphatic branched-chain hydrocarbon group. "Chain alkyl of C1-C30" may be, for example, a straight-chain alkyl having 1 to 30 carbon atoms or a branched-chain alkyl having 3 to 30 carbon atoms. The number of carbon atoms in the chain alkyl may be, for example, 1 to 3, 1 to 5, 1 to 8, 1 to 10, 1 to 20, 2 to 5, 2 to 10, 3 to 6, 3 to 10, 4 to 8, 4 to 10, 8 to 20, 8 to 30, or 15 to 30, and examples are 1, 2, 5, 8, 10, 20, 30 or a value between any two of the foregoing numerical values. Suitable examples of "chain alkyl" include but are not limited to methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, 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, n-nonyl, n-decyl, 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, or n-triacontyl.

[0043] The term "chain alkoxy" refers to a group with the general formula *-O-chain alkyl, where * represents the connection site and O represents an oxygen atom. Suitable examples of "chain alkoxy" include but are not limited to methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), tert-butoxy (-O-C(CH3)3 or -OtBu), n-hexanoxy (-O-C6H 13 ), n-decanoxy (-O-C 10 H 21 ), or n-dodecanoxy (-O-C 12 H 25 ).

[0044] The term "aryl" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, which can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl. For a polycyclic ring system, at least one ring is an aromatic ring system. "An aryl having 6 to 30 ring atoms" can be an aryl having 6 to 20 ring atoms, an aryl having 6 to 18 ring atoms, an aryl having 6 to 16 ring atoms, an aryl having 6 to 14 ring atoms, or an aryl having 6 to 10 ring atoms. The number of ring atoms can be, for example, 6, 10, 12, 14, 16, 18, 20, 24, 26, 28, 30, or a value between any two of the foregoing values. Suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, dinaphthylenyl, acenaphthylenyl, and their derivatives. It can be understood that multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N, or O atoms), such as acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, and diaryl ether systems should also be included in the definition of aryl.

[0045] The term "heteroaryl" refers to a group in which at least one carbon atom in the aryl group is replaced by a non-carbon atom, and the non-carbon atom can be one or more of N atom, O atom, S atom, Si atom, and P atom. The number of heteroatoms is, for example, 1 to 20. "A heteroaryl having 5 to 30 ring atoms" can be a heteroaryl having 5 to 20 ring atoms, a heteroaryl having 5 to 18 ring atoms, a heteroaryl having 5 to 16 ring atoms, a heteroaryl having 5 to 14 ring atoms, a heteroaryl having 5 to 12 ring atoms, or a heteroaryl having 5 to 10 ring atoms. The number of ring atoms can be, for example, 5, 10, 12, 14, 18, 20, 24, 26, 28, 30, or a value between any two of the foregoing values. Suitable examples include, but are not limited to, thienyl, furyl, pyrrolyl, dioxazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuryl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuryl, thienofuryl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, phthalazinyl, phenanthridinyl, peridinyl, quinazolinone, dibenzothienyl, dibenzofuryl, or carbazolyl.

[0046] In this application, the single bond to which the substituent is attached passes through the corresponding ring, indicating that the substituent can be attached to an optional position of the ring. For example In the formula, R3 can be connected to any substitutable site in the left benzene ring, and R4 can be connected to any substitutable site in the right benzene ring. Further, in the present application, when the same substituent appears multiple times, it can be independently selected from different groups; for example, if the above general formula contains n2 R3 groups, each R3 can be independently selected from different groups. In addition, * represents the connection site, and any connectable site on the two benzene rings in the group (R1 or R2) shown in the above general formula can be connected to the carbon atom in Ar3 or Ar4.

[0047] In the present application, "halogen group" or "halogen" represents -Cl, -Br, -F or -I; hydroxyl group represents -OH; carboxyl group represents -COOH; nitro group represents -NO2; sulfonic acid group represents -SO3H; mercapto group represents -SH; cyano group represents -C≡N.

[0048] In the present application, "its combination", "any combination thereof", "any combination mode thereof", etc. include all suitable combination modes of any two or more than two items in the listed items.

[0049] An embodiment of the present application provides an organic compound having a structure shown in the following general formula (Ⅰ):

[0050]

[0051] In the general formula (Ⅰ), are respectively selected from & represents the fusion site with of.

[0052] In the general formula (Ⅰ), do not exist or are respectively selected from and at least one of them exists, and * represents the connection site with R1 or R2. It can be understood that when does not exist, correspondingly R2 also does not exist; when does not exist, correspondingly R1 also does not exist. In some embodiments of the present application, both exist. Based on the highly symmetric structure and larger conjugated structure, it is beneficial to further improve the stability and hole mobility of the organic compound.

[0053] In the general formula (Ⅰ), R1 and R2 do not exist or are respectively independently selected from the groups having the structures shown in the following formula (2-1) or formula (2-2) to facilitate the regulation of the HOMO energy level and hole mobility of the organic compound.

[0054]

[0055] In formula (2-1), X is selected from O, S, SiR5R6, CR7R8 or NR9, and R5 to R9 are each independently selected from -H, -D, -NR 10 R 11 , a halogen group, a hydroxyl group, a mercapto group, a nitro group, a sulfonic acid group, an aldehyde group, a cyano group, an unsubstituted or at least one substituent-substituted C1-C30 linear alkyl group, an unsubstituted or at least one substituent-substituted C1-C30 linear alkoxy group, an unsubstituted or at least one substituent-substituted aryl group having 6 to 30 ring atoms, or an unsubstituted or at least one substituent-substituted heteroaryl group having 5 to 30 ring atoms, or a combination of these groups. Each occurrence of the substituent is independently selected from -D, a C1-C10 linear alkyl group, a C1-C10 linear alkoxy group, or an aryl group having 6 to 14 ring atoms.

[0056] In some embodiments of the present application, R5 to R9 are each independently selected from a C1-C10 linear alkyl group, a C1-C10 linear alkoxy group or a phenyl group.

[0057] In formula (2-2), Y-* is selected from N-* or N-R 12 -*, R 12 is selected from a C1-C30 linear alkylene group, a C1-C30 linear alkoxylene group, an arylene group having 6 to 14 ring atoms, or a heteroarylene group having 5 to 14 ring atoms, or a combination of these groups. In some embodiments of the present application, R 12 is selected from a C1-C10 linear alkylene group, a C1-C10 linear alkoxylene group, or a phenylene group.

[0058] In formulas (2-1) and (2-2), n1 and n2 are each independently selected from integers from 0 to 5, such as 0, 1, 2, 3, 4 or 5. n1 and n2 may be the same or different.

[0059] In general formula (I), R3 and R4 are each independently selected from a single bond, -H, -D, a hydroxyl group, a mercapto group, -NR 10 R 11 , an unsubstituted or at least one substituent-substituted C1-C30 linear alkyl group, or an unsubstituted or at least one substituent-substituted C1-C30 linear alkoxy group, or a combination of these groups. There is no connection between adjacent R3 and R4, or adjacent R3 and R4 are connected to form a cyclic structure with X or Y. Among them, R 10 and R 11Each occurrence is independently selected from -H, -D, a linear alkyl group having 1 to 30 carbon atoms, a linear alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 14 ring atoms; each occurrence of the substituent is independently selected from -D, a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms, or an aryl group having 6 to 14 ring atoms.

[0060] In some embodiments of the present application, R 10 and R 11 are each independently selected from -H, -D, a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms, or a phenyl group.

[0061] In some embodiments of the present application, R3 and R4 are each independently selected from a single bond, -H, -D, a hydroxyl group, a mercapto group, -NR 10 R 11 , a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms, or a phenyl group.

[0062] Furthermore, in some embodiments of the present application, R3 and R4 are each independently selected from a single bond, -H, -D, a hydroxyl group, a mercapto group, -NR 10 R 11 , a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms, or a phenyl group.

[0063] Even further, in some embodiments of the present application, adjacent R3 and R4 are connected to each other to form *-*, *-S-*, *-O-*, *-CR 13 R 14 -* or *-NR 15 -*, where, - represents a single bond, R 13 , R 14 and R 15 are each independently selected from a linear alkyl group having 1 to 10 carbon atoms or a phenyl group, herein, * represents the connection site to the benzene ring.

[0064] In the organic compound, R1 and R2 may be the same or different. In some embodiments of the present application, R1 and R2 are the same, so that the organic compound has good structural symmetry, which is not only easier to synthesize but also has high stability.

[0065] In some embodiments of the present application, R1 and R2 are each independently selected from any one of the groups represented by the following formulas (1-1) to (1-13):

[0066]

[0067] In some embodiments of the present application, the organic compound has a structure represented by any one of the following formulas (3-1) to (3-10):

[0068]

[0069] Further, in some embodiments of the present application, the organic compound has a structure represented by any of the following structural formulas:

[0070]

[0071] In the organic compound of the embodiment of the present application, the organic compound uses a fluorenone structure as the core skeleton and has a benzotriazole structural unit. Among them, the fluorenone structure is an excellent hole skeleton, and the benzotriazole structure has ultraviolet absorption performance, which can avoid or reduce the damage of ultraviolet light to the fluorenone structure, so that the performance of the organic compound is not easily affected by ultraviolet light, has better light stability, and is more conducive to intramolecular charge transfer, and has good hole mobility and hole generation ability, and can be used as a hole injection material or a hole transport material.

[0072] It can be understood that the organic compound can be used to prepare the hole functional layer of optoelectronic devices, such as the hole transport layer or the hole injection layer. On the one hand, because the organic compound has high hole transport / injection performance, it can enhance the hole injection ability and improve the carrier balance of the device, and helps to enhance the optoelectronic performance and lifespan of the device. On the other hand, because the compound has better ultraviolet absorption performance and light stability, it can absorb the ultraviolet rays generated during the device preparation process, reduce the damage of ultraviolet rays to the material, and improve the light stability of the device.

[0073] The embodiment of the present application also provides a preparation method of an organic compound, which can be used to prepare the organic compound with the structure shown in the general formula (Ⅰ) in the foregoing text, as Figure 1 shown, 1. The preparation method of the organic compound includes the following steps:

[0074] (A1) Using a first compound as a raw material, carrying out a ring-closure reaction to obtain a second compound;

[0075] (A2) Mixing the second compound with a third compound and carrying out a nitrogen-nitrogen coupling reaction to obtain the organic compound with the structure shown in the general formula (Ⅰ).

[0076] Among them, the first compound has a structure represented by the following formula (4-1):

[0077]

[0078] The first compound can be, for example, any of the following structures:

[0079]

[0080] The second compound has the structure shown in the following formula (4-2):

[0081]

[0082] In formula (4-2), the selection ranges of Ar1 to Ar4 all refer to the description above.

[0083] The general formula of the third compound is Ar-Z, where Ar represents R1 or R2. When the atom in Ar connected to Z is an N atom, Z is -H; when the atom in Ar connected to Z is a non-N atom, Z is a halogen group. The selection ranges of R1 and R2 all refer to the description above.

[0084] In some embodiments of the present application, step (A1) includes the steps of: mixing the first compound, sodium nitrite, acetic acid and water to carry out the ring-closure reaction.

[0085] Among them, the molar ratio of the first compound to sodium nitrite is 1:(5-20), for example, it can be 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:11, 1:12, 1:13, 1:14, 1:15, 1:16, 1:17, 1:18, 1:19, 1:20 or a value between any two of the foregoing values; and / or, the temperature of the ring-closure reaction is 20°C to 30°C, for example, it can be 20°C, 21°C, 22°C, 23°C, 24°C, 25°C, 26°C, 27°C, 28°C, 29°C, 30°C or a value between any two of the foregoing values; and / or, the time of the ring-closure reaction is 10 min to 60 min, for example, it can be 10 min, 20 min, 30 min, 40 min, 50 min, 60 min or a value between any two of the foregoing values, so as to further improve the yield and purity of the second compound.

[0086] In step (A2), the molar ratio of the second compound to the third compound is 1:(3-5), for example, it can be 1:3, 1:3.5, 1:3.8, 1:4, 1:4.5, 1:4.7, 1:4.9, 1:5 or a value between any two of the foregoing values; and / or, the reaction temperature of the nitrogen-nitrogen coupling reaction is 80-110°C, for example, it can be 80°C, 85°C, 90°C, 95°C, 100°C, 105°C, 110°C or a value between any two of the foregoing values; and / or, the time of the nitrogen-nitrogen coupling reaction is 6 h to 24 h, for example, it can be 6 h, 6.5 h, 7 h, 7.5 h, 8 h, 8.5 h, 9 h, 9.5 h, 10 h, 10.5 h, 11 h, 12 h, 13 h, 14 h, 15 h, 18 h, 20 h, 22 h, 24 h or a value between any two of the foregoing values, so as to further improve the yield and purity of the organic compound.

[0087] In some embodiments, step (A2) can be carried out under the protection of an inert gas to isolate or reduce water and oxygen in the reaction system. It can be understood that the inert gas generally refers to protective gases such as nitrogen, helium, argon, etc.

[0088] It should be noted that the organic compounds provided in this application are not limited to those prepared by the preparation method of the organic compounds provided in this application.

[0089] Based on the above embodiments of the organic compounds, the present application also proposes a composition, which includes a solvent and an organic compound as described in any one of the foregoing, or an organic compound prepared by the preparation method as described in any one of the foregoing. The composition can be an ink, for example, it can be a hole-functional material ink for preparing the hole-functional layer of an optoelectronic device. It can be understood that the composition can contain one of the foregoing organic compounds or two or more of the foregoing organic compounds.

[0090] In some embodiments of the present application, the solvent is selected from one or more of alkanes, aromatic hydrocarbons, halogenated alkanes, alcohol compounds, ether compounds, furan compounds, pyridine compounds, amide compounds, ester compounds, and sulfone compounds. Among them, the alkanes include but are not limited to one or more of nonane, decane, dodecane, terpane, butylcyclohexane, n-octane, n-hexane, n-heptane, n-nonane, n-decane, cyclohexane, and cyclopentane; the aromatic hydrocarbons include but are not limited to one or more of diethylbenzene, mesitylene, propylbenzene, isopropylbenzene, p-cumene, butylbenzene, 1-methylnaphthalene or indene; the halogenated alkanes include but are not limited to one or more of dichloromethane, chloroform, and carbon tetrachloride; the alcohol compounds include but are not limited to one or more of methanol, ethanol, propanol, butanol, ethylene glycol, and glycerol; the ether compounds include but are not limited to ethylene glycol monomethyl ether; the furan compounds include but are not limited to tetrahydrofuran; the pyridine compounds include but are not limited to pyridine; the amide compounds include but are not limited to N,N-dimethylformamide; the sulfone compounds include but are not limited to dimethyl sulfoxide. As an example, the solvent is selected from one or more of toluene, chlorobenzene, chloroform, tetralin, and chloronaphthalene.

[0091] In some embodiments of the present application, the concentration of the organic compound in the composition is 5 mg / mL to 20 mg / mL, for example, it can be 5 mg / mL, 8 mg / mL, 10 mg / mL, 13 mg / mL, 15 mg / mL, 18 mg / mL, 20 mg / mL, or a value between any two of the foregoing values.

[0092] In some embodiments of the present application, the composition further includes a hole functional material, which includes but is not limited to one or more of an undoped first inorganic compound, a doped second inorganic compound, and an organic material. Among them, the organic materials include but are not limited to poly(3,4-ethylenedioxythiophene):poly(styrenesulfonic acid) (abbreviation: PEDOT:PSS, CAS No. 155090-83-8), copper phthalocyanine (CAS No. 147-14-8), titanium oxyphthalocyanine (CAS No. 26201-32-1), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (CAS No. 29261-33-4), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (CAS No. 105598-27-4), polyaniline (CAS No. 25233-30-1), polypyrrole (CAS No. 30604-81-0), 3-hexyl-substituted polythiophene (CAS No. 104934-50-1), poly(9-vinylcarbazole) (abbreviation: PVK, CAS No. 25067-59-8), 4,4'-bis(9-carbazolyl)biphenyl (abbreviation: CBP, CAS No. 58328-31-7), poly[bis(4-phenyl)(4-butylphenyl)amine], 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (abbreviation: TAPC, CAS No. 58473-78-2), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)] (abbreviation: TFB, CAS No. 220797-16-0), poly[(N,N'-(4-n-butylphenyl)-N,N'-diphenyl-1,4-phenylenediamine)-ALT-(9,9-din-octylfluorene-2,7-diyl)] (CAS No. 223569-31-1), 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (CAS No. 124729-98-2), 4,4',4”-tris(carbazol-9-yl)triphenylamine (abbreviation: TCTA, CAS No. 139092-78-7), 4,4',4'-tris(2-naphthylphenylamino)triphenylamine (CAS No. 185690-41-9), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (abbreviation: NPB, CAS No. 123847-85-8), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (abbreviation: TPD, CAS No. 65181-78-4), N,N'-bis[4-(diphenylamino)phenyl]-N,N'-diphenylbenzidine (CAS No. 209980-53-0), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-9,9-spirobifluorene-2,One or more of 7-diamine (abbreviated as Spiro-TPD, CAS No. 1033035-83-4), N2,N7-di-1-naphthyl-N2,N7-diphenyl-9,9'-spirobi[9H-fluorene]-2,7-diamine (CAS No. 932739-76-9), poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (abbreviated as PTTA, CAS No. 1333317-99-9), and 2,2',7,7'-tetrakis[N,N-bis(4-methoxyphenyl)amino]-9,9'-spirobifluorene (abbreviated as Spiro-omeTAD, CAS No. 207739-72-8); and / or, the non-doped first inorganic compound includes but is not limited to one or more of graphene, C60, nickel oxide (such as NiO), molybdenum oxide (such as MoO3), tungsten oxide (such as WO3), vanadium oxide (such as V2O5), p-type gallium nitride, chromium oxide (such as Cr2O3), copper oxide (such as CuO or Cu2O), copper sulfide (such as CuS), molybdenum sulfide (such as MoS2), and tungsten sulfide (such as WS2); and / or, the doped second inorganic compound is a host inorganic compound doped with a second doping element, and the host inorganic compound includes but is not limited to one or more of graphene, C60, nickel oxide (such as NiO), molybdenum oxide (such as MoO3), tungsten oxide (such as WO3), vanadium oxide (such as V2O5), p-type gallium nitride, chromium oxide (such as Cr2O3), copper oxide (such as CuO or Cu2O), copper sulfide (such as CuS), molybdenum sulfide (such as MoS2), and tungsten sulfide (such as WS2), and / or the second doping element includes but is not limited to one or more of nickel, molybdenum, tungsten, vanadium, chromium, copper, and platinum group metal elements.,

[0093] The composition of the embodiment of the present application has good hole generation ability and hole mobility, can be used to prepare the hole functional layer of optoelectronic devices, and the composition has good light stability, and when preparing the hole functional layer, the film layer can be prevented from being damaged by ultraviolet light.

[0094] The embodiment of the present application also provides an optoelectronic device, and the optoelectronic device includes but is not limited to a light-emitting device, a photovoltaic cell, or a photodetector, such as Figure 2 As shown, the optoelectronic device 10 includes an anode 101, a functional layer 103, and a cathode 102. Among them, the anode 101 and the cathode 102 are disposed opposite to each other, the functional layer 103 is disposed between the anode 101 and the cathode 102, the functional layer 103 includes a hole functional layer 1032, and the material of the hole functional layer 1032 includes an organic compound as described in any one of the foregoing, or an organic compound prepared by the preparation method as described in any one of the foregoing, or the hole functional layer 1032 is prepared by using the composition as described in any one of the foregoing.

[0095] In the optoelectronic device 10 according to an embodiment of the present application, the material of the hole functional layer 1032 includes an organic compound represented by the general formula (I). First, since the organic compound has excellent hole transport / injection performance, it is beneficial to promote the electron-hole transport balance of the optoelectronic device 10, so that the optoelectronic device 10 has good optoelectronic performance and device lifetime. Second, since the organic compound has ultraviolet absorption performance, it can avoid or reduce the negative impact of ultraviolet light on the performance of the hole functional layer 1032, so that the hole functional layer 1032 has good performance stability, and during the process of manufacturing the optoelectronic device 10, it can reduce the damage of ultraviolet light to the material and improve the performance stability of the optoelectronic device 10. Third, the organic compound uses fluorenone as the core structure, has high molecular planarity, improves the energy level matching degree of the hole functional layer 1032, and endows the hole functional layer 1032 with good morphological characteristics.

[0096] In the optoelectronic device 10 according to an embodiment of the present application, the hole functional layer 1032 may be a single-layer structure or a multi-layer structure, and the thickness of the hole functional layer 1032 is, for example, 10 nm to 100 nm. When the hole functional layer 1032 is a multi-layer structure, the hole functional layer 1032 includes, for example, one or more of a hole injection layer, a hole transport layer, and an electron blocking layer. For the hole functional layer 1032 including a hole injection layer, a hole transport layer, and an electron blocking layer, the hole transport layer is located between the hole injection layer and the electron blocking layer, and the hole injection layer is closer to the anode 101 than the electron blocking layer. For the hole functional layer 1032 including a hole transport layer and an electron blocking layer, the hole transport layer is closer to the anode 101 than the electron blocking layer. For the hole functional layer 1032 including a hole injection layer and a hole transport layer, the hole injection layer is closer to the anode 101 than the hole transport layer.

[0097] It should be noted that when the hole functional layer 1032 contains multiple materials and the hole functional layer 1032 is a multi-layer structure, the multiple materials may all be in the same layer, or in different layers respectively, or partially in the same layer, and one layer, some layers, or all layers of the materials may include the organic compound described in any one of the foregoing, or the organic compound prepared by the preparation method described in any one of the foregoing, or one layer, some layers, or all layers are prepared using the composition described in any one of the foregoing. For example, Figure 2As shown, when the hole functional layer 1032 is composed of a hole injection layer 10321 and a hole transport layer 10322 which are stacked, the material of the hole injection layer 10321 is PEDOT:PSS, and the material of the hole transport layer 10322 includes any one of the organic compounds described above, or an organic compound prepared by any one of the preparation methods described above, or the hole transport layer 10322 is prepared from any one of the compositions described above. It can be understood that when the material of one or some of the layers does not include the organic compound represented by the general formula (I), the material of the one or some of the layers can be selected from one or more of the organic materials, the first inorganic compound material and the second inorganic compound material.

[0098] In some embodiments of the present application, the materials of the anode 101 and the cathode 102 are independently selected from one or more of metals, carbon materials and first metal oxides. Among them, the metals include but are not limited to one or more of Al, Ag, Cu, Mo, Au, Ba, Pt, Ca, Ir, Ni and Mg. The carbon materials include but are not limited to one or more of graphite, carbon nanotubes, graphene and carbon fibers. The first metal oxide can be doped or undoped. The doped first metal oxides include but are not limited to one or more of indium tin oxide (ITO), fluorine-doped tin oxide (FTO), antimony tin oxide (ATO), aluminum-doped zinc oxide (AZO), gallium-doped zinc oxide (GZO), indium-doped zinc oxide (IZO) and magnesium-doped zinc oxide (MZO). The undoped first metal oxides include but are not limited to one or more of TiO2, SnO2, ZnO and In2O3.

[0099] It should be noted that the anode 101 and the cathode 102 can also be composite electrodes respectively. The composite electrodes have a structure similar to a "sandwich". The materials of the upper layer and the bottom layer are doped or undoped first metal oxides respectively, and the material of the middle layer is a metal. Examples include one or more of AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, TiO2 / Ag / TiO2, TiO2 / Al / TiO2, TiO2 / Ag / TiO2 and TiO2 / Al / TiO2. The average thicknesses of the anode 101 and the cathode 102 are, for example, independently selected from 20 nm to 300 nm.

[0100] In some embodiments of the present application, the optoelectronic device 10 is a light-emitting device, and the functional layer 103 further includes a light-emitting layer 1033. The light-emitting layer 1033 is disposed between the cathode 102 and the hole functional layer 1032, and the thickness of the light-emitting layer 1033 is, for example, 10 nm to 100 nm. Among them, the material of the light-emitting layer 1033 includes one or more of an organic light-emitting material and a light-emitting quantum dot. Among them, the organic light-emitting material includes, but is 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, a diarylanthracene derivative, a stilbene aromatic derivative, a pyrene derivative, a fluorene derivative, a TBPe fluorescent material, a TTPX fluorescent material, a TBRb fluorescent material, a DBP fluorescent material, a delayed fluorescence material, a TTA material, a thermally activated delayed material, a polymer containing a B-N covalent bond, a hybrid local charge transfer excited state material, an exciplex luminescent material, polyacetylene and its derivatives, poly(p-phenylene) and its derivatives, polythiophene and its derivatives, polyfluorene and its derivatives, or one or more of them.

[0101] The light-emitting quantum dots include, but are not limited to, one or more of red quantum dots, green quantum dots, and blue quantum dots, and the light-emitting quantum dots include, but are not limited to, one or more of single-component quantum dots, core-shell structure quantum dots, inorganic perovskite quantum dots, organic perovskite quantum dots, and organic-inorganic hybrid perovskite quantum dots. The core-shell structure quantum dots include one or more shell layers. The average particle size of the light-emitting quantum dots can be 2 nm to 20 nm, for example, it can be 2 nm, 4 nm, 6 nm, 8 nm, 10 nm, 12 nm, 15 nm, 20 nm, or a value between any two of the foregoing values.

[0102] For single-component quantum dots and core-shell structure quantum dots, the material of the single-component quantum dots, the material of the core of the core-shell structure quantum dots, or the material of the shell of the core-shell structure quantum dots includes, but is not limited to, one or more of II-VI group compounds, III-V group compounds, III-VI group compounds, IV-VI group compounds, and I-III-VI group compounds. Among them, the II-VI group compounds include, but are not limited to, one or more of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and HgZnSTe. The III-VI group compounds include, but are not limited to, one or more of In2S3, In2Se3, InGaS3, and InGaSe3. The III-V group compounds include, but are not limited to, one or more of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and InAlPSb. The IV-VI group compounds include, but are not limited to, one or more of SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, and SnPbSTe. The I-III-VI group compounds include, but are not limited to, one or more of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2, AgInGaS2, and CuInGaS2.

[0103] For inorganic perovskite quantum dots, the general structural formula of inorganic perovskite quantum dots is AMX3, where A is Cs + , M is a divalent metal cation, and M includes but is not limited to Pb 2+ , Sn 2+ , Cu 2+ , Ni 2+ , Cd 2+ , Cr 2+ , Mn 2+ , Co 2+ , Fe 2+ , Ge 2+ , Yb 2+ or Eu 2+ , X is a halogen anion, including but not limited to Cl - , Br - or I - .

[0104] For organic perovskite quantum dots, the general structural formula of organic perovskite quantum dots is CMX3, where C is formamidinium, M is a divalent metal cation, and M includes but is not limited to Pb 2+ , Sn 2+ , Cu 2+ , Ni 2+ , Cd 2+ , Cr 2+ , Mn 2+ , Co 2+ , Fe 2+ , Ge 2+ , Yb 2+ or Eu 2+ , X is a halogen anion, including but not limited to Cl - , Br - or I - .

[0105] For organic-inorganic hybrid perovskite quantum dots, the general structural formula of organic-inorganic hybrid perovskite quantum dots is BMX3, where B is selected from organic amine cations, and organic amine cations include but are not limited to CH3(CH2) n-2 NH 3+ (n≥2) or NH3(CH2) n NH3 2+ (n≥2), M is a divalent metal cation, and M includes but is not limited to Pb 2+ , Sn 2+ , Cu 2+ , Ni 2+ , Cd 2+ , Cr 2+ , Mn 2+ , Co 2+ , Fe2+ , Ge 2+ , Yb 2+ or Eu 2+ , where X is a halogen anion, including but not limited to Cl - , Br - or I - .

[0106] It should be noted that when the material of the light-emitting layer 1033 includes light-emitting quantum dots, ligands can also be connected to the surface of the light-emitting quantum dots. The ligands include but are not limited to aliphatic carboxylic acid ligands with C1-C 30 , aromatic carboxylic acid ligands with C6-C 30 , aliphatic thiol ligands with C1-C 30 , thiol aromatic ligands with C6-C 30 , aliphatic amine ligands with C1-C 30 , aromatic amine ligands with C6-C 30 , aliphatic phosphine ligands with C1-C 30 , aromatic phosphine ligands with C6-C 30 , aromatic phosphate ligands with C6-C 30 and one or more of halogen ligands.

[0107] Among them, the aliphatic carboxylic acid ligands with C1-C 30 include but are not limited to one or more of octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, eicosanoic acid, tetracosanoic acid, hexacosanoic acid, oleic acid, linoleic acid, arachidic acid, arachidonic acid, erucic acid, and docosahexaenoic acid; the aromatic carboxylic acid ligands with C6-C 30 include but are not limited to one or more of benzoic acid, biphenylcarboxylic acid, and 1-naphthoic acid. The aliphatic thiol ligands with C1-C 30 include but are not limited to one or more of hexanethiol, octanethiol, nonanethiol, decanethiol, undecanethiol, dodecanethiol, hexadecanethiol, and octadecanethiol. The thiol aromatic ligands with C6-C 30 include but are not limited to one or more of benzenethiol, triphenylmethanethiol, and p-terphenyl-4,4”-dithiol. The aliphatic amine ligands with C1-C 30 include but are not limited to one or more of hexylamine, octylamine, dioctylamine, trioctylamine, nonylamine, decylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, and oleylamine. The aromatic amine ligands with C6-C 30 include but are not limited to one or more of aniline, indanpropylamine, 4-octylaniline, and benzidine. The aliphatic phosphine ligands with C1-C 30The fatty phosphine ligands include, but are not limited to, one or more of trimethylphosphine, triethylphosphine, tripropylphosphine, tributylphosphine, trihexylphosphine, trioctylphosphine, tridecylphosphine, tributylphosphine oxide, trihexylphosphine oxide, trioctylphosphine oxide, and tridecylphosphine oxide, C6-C 30 The aromatic phosphine ligands include, but are not limited to, one or more of bis(2-diphenylphosphinoethyl)phenylphosphine and triphenylphosphine oxide, C6-C 30 The aromatic phosphate ligands include, but are not limited to, one or more of tetraethyl p-xylene diphosphate and ethyl diphenyl phosphate. The halogen ligands include, but are not limited to, -Cl, -F, -I, or -Br.

[0108] In some embodiments of the present application, continue to refer to Figure 2 , the functional layer 103 further includes an electron functional layer 1031, and the electron functional layer 1031 is disposed between the hole functional layer 1032 and the cathode 102. When the functional layer 103 further includes a light-emitting layer 1033, the electron functional layer 1031 is disposed between the light-emitting layer 1033 and the cathode 102. The electron functional layer 1031 may be a single-layer structure or a multi-layer structure, and the thickness of the electron functional layer 1031 is, for example, 10 nm to 100 nm. When the electron functional layer 1031 is a multi-layer structure, the electron functional layer 1031 includes, for example, one or more of an electron injection layer, an electron transport layer, and a hole blocking layer. For the electron functional layer 1031 including an electron injection layer, an electron transport layer, and a hole blocking layer, the electron transport layer is located between the electron injection layer and the hole blocking layer, and the electron injection layer is closer to the cathode 102 than the hole blocking layer; for the electron functional layer 1031 including an electron transport layer and a hole blocking layer, the electron transport layer is closer to the cathode 102 than the hole blocking layer; for the electron functional layer 1031 including an electron injection layer and an electron transport layer, the electron injection layer is closer to the cathode 102 than the electron transport layer.

[0109] Among them, the electronic functional layer 1031 includes at least one undoped second metal oxide, at least one IIB-VIA group semiconductor material, at least one IIIA-VA group semiconductor material, at least one IB-IIIA-VIA group semiconductor material, and at least one doped third metal oxide. Among them, the undoped second metal oxide is selected from ZnO, TiO2, SnO2, BaO, Ta2O3, Al2O3 or ZrO2; and / or, the IIB-VIA group semiconductor material is selected from ZnS, ZnSe or CdS; and / or, the IIIA-VA group semiconductor material is selected from InP or GaP; and / or, the IB-IIIA-VIA group semiconductor material is selected from CuInS or CuGaS; and / or, the main material of the doped third metal oxide is selected from ZnO, TiO2, SnO2, BaO, Ta2O3, Al2O3 or ZrO2, and the doping elements of the doped third metal oxide include but are not limited to one or more of Mg, Ca, Zr, W, Ga, Li, Al, Ti, Y, In and Sn. The molar percentage of the doping elements in the doped third metal oxide is, for example, not higher than 5%, not higher than 10%, not higher than 20%, not higher than 30% or not higher than 50%. The doped third metal oxide includes but is not limited to magnesium zinc oxide, calcium zinc oxide, zirconium zinc oxide, gallium zinc oxide, aluminum zinc oxide, lithium zinc oxide, titanium zinc oxide, yttrium zinc oxide, indium tin oxide or lithium titanium oxide, exemplified as Zn (1-x) Mg x O, Zn (1-x) Ca x O, Zn (1-x) Zr x O, Zn (1-x) Ga x O, Zn (1-x) Al x O, Zn (1-x) Li x O, Al (1-x) Zn x O, Zn (1-x) Ti x O, Zn (1-x) Y x O, In (1-x) Sn x O and Ti (1-x) Li x O, one or more of them, where 0 < x ≤ 0.5.

[0110] It should be noted that when the electronic functional layer 1031 includes multiple materials and the electronic functional layer 1031 is a multi-layer structure, all of the multiple materials may be in the same layer, or in different layers respectively, or some in the same layer.

[0111] It can be understood that the optoelectronic device 10 may further include a substrate disposed on the side of the anode 101 away from the functional layer 103 or on the side of the cathode 102 away from the functional layer 103. The substrate can be a rigid substrate or a flexible substrate. The materials of the rigid substrate include, but are not limited to, one or more of glass, ceramics, and silicon wafers. The materials of the flexible substrate include, but are not limited to, one or more of polyimide, polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate, and polyethersulfone.

[0112] It should be noted that the preparation methods of the respective functional layers in the optoelectronic device 10 include, but are not limited to, chemical methods and / or physical methods. Among them, the chemical methods include, but are not limited to, one or more of chemical vapor deposition, sequential ionic layer adsorption and reaction, anodic oxidation, electrolytic deposition, and coprecipitation. The physical methods include, but are not limited to, physical coating methods and solution methods. The physical coating methods include, but are not limited to, one or more of thermal evaporation coating, electron beam evaporation coating, magnetron sputtering, multi-arc ion coating, physical vapor deposition, atomic layer deposition, and pulsed laser deposition. The solution methods include, but are not limited to, one or more of spin coating, printing, inkjet printing, blade coating, printing, dip coating, immersion, spraying, roll coating, casting, slot die coating, and bar coating. After the respective functional layers of the optoelectronic device are prepared, a packaging treatment process is also required. The packaging treatment can be carried out by using common machine packaging or manual packaging. In the environment of the packaging treatment, the oxygen content and the water content are both lower than 0.1 ppm to ensure the stability of the optoelectronic device. Specifically, the packaging materials used to form the packaging layer are, for example, selected from one or more of ultraviolet photoresist, metal thin film, and glass glue. As an example, the packaging material is acrylic resin or epoxy resin.

[0113] Taking the preparation of the hole transport layer by the solution method as an example, the preparation method of the hole transport layer includes the steps of depositing a solution containing the organic compound shown in the general formula (Ⅰ), and then performing a drying treatment to solidify into a film to obtain the hole transport layer. Among them, the deposition method includes, but is not limited to, one or more of spin coating, printing, inkjet printing, blade coating, printing, dip coating, immersion, spraying, roll coating, casting, slot die coating, and bar coating. The drying treatment includes, but is not limited to, one or more of heat treatment and vacuum drying treatment.

[0114] The embodiments of the present application further provide an electronic device, which includes any one of the optoelectronic devices described above. The electronic device can be, for example, any electronic product with a display function, including but not limited to smartphones, tablet personal computers, mobile phones, video telephones, e-book readers, laptop PCs, netbook computers, workstations, servers, personal digital assistants, portable multimedia players, MP3 players, mobile medical devices, cameras, game consoles, digital cameras, in-vehicle navigators, electronic billboards, automated teller machines, smart bracelets, smart watches, Virtual Reality (VR) devices or wearable devices.

[0115] The technical solutions and technical effects of the present application will be described in detail below through specific examples, comparative examples and experimental examples. The following examples are only partial examples of the present application and do not specifically limit the present application.

[0116] Example 1 of Organic Compound

[0117] This embodiment provides an organic compound M1 and a preparation method thereof. The synthetic route of the organic compound M1 is as follows:

[0118]

[0119] The preparation method of the organic compound M1 includes the following steps:

[0120] S1.1: Take a 100 mL two-necked flask, add 1 mmol of compound M1-1 (CAS No. 2069998-28-1), 10 mmol of sodium nitrite (CAS No. 7632-00-0) and 20 mL of acetic acid thereto. Dissolve the above raw materials in 10 mL of deionized water, stir at room temperature for 30 min, stop the reaction when it is monitored that the raw materials have completely reacted, distill the reaction solution under reduced pressure to remove the solvent, mix the crude product with silica gel of 200 to 300 mesh, and then perform column chromatography separation. The mobile phase is composed of petroleum ether and ethyl acetate (the volume ratio of petroleum ether to ethyl acetate is 1:1) to obtain compound M1-2 with a yield of 68%. The NMR data is: 1HNMR (500 MHz, Chloroform-d) δ 8.94 (s, 2H), 8.72 (s, 2H);

[0121] S1.2. Take another 100 mL two-necked flask, add 1 mmol of compound M1-2 thereto, then add 40 mL of toluene. After the compound M1-2 is dissolved in toluene, add 3 mmol of diphenylamine and 0.5 mmol of copper chloride. Pass in nitrogen, use a vacuum pump to evacuate and replace with nitrogen for 15 min. Wrap the two-necked flask containing the reaction system with tin foil, stir in the dark and heat to 110 °C for reaction for 24 h. Stop the reaction and cool to room temperature. Extract the reaction solution, and then repeat the washing treatment on the extraction phase 3 to 4 times. Each washing treatment is successively carried out with 100 mL of dichloromethane washing and 25 mL of deionized water washing. Then use anhydrous magnesium sulfate to dry the organic phase obtained after the washing treatment, and then use column chromatography for rough separation. The eluent is a mixture composed of petroleum ether, dichloromethane and ethyl acetate, and the volume ratio of petroleum ether:dichloromethane:ethyl acetate is 20:1:1 to obtain organic compound M1. Organic compound M1 is a white solid with a yield of 70%. The nuclear magnetic detection data is: 1H NMR (500 MHz, Chloroform-d) δ 8.67 (s, 2H), 8.55 (s, 2H), 7.30 - 7.24 (m, 8H), 7.17 - 7.12 (m, 8H), 7.04 - 6.99 (m, 4H).

[0122] Example 2 of Organic Compound

[0123] This example provides an organic compound M2 and its preparation method. The synthesis route of the organic compound M2 is as follows:

[0124]

[0125] Compared with the preparation method of the organic compound M1, the difference in the preparation method of the organic compound M2 is that: in step S1.2, "3 mmol of diphenylamine" is replaced with "3 mmol of 4-bromotriphenylamine (CAS No. 36809-26-4)". The nuclear magnetic data of the prepared organic compound M2 is: 1H NMR (500 MHz, Chloroform-d) δ 8.72 (s, 2H), 8.60 (s, 2H), 7.78 - 7.74 (m, 4H), 7.27 - 7.22 (m, 8H), 7.19 - 7.16 (m, 4H), 7.11 - 7.07 (m, 8H), 7.06 - 7.00 (m, 4H).

[0126] Example 3 of Organic Compound

[0127] This example provides an organic compound M3 and its preparation method. The synthesis route of the organic compound M3 is as follows:

[0128]

[0129] Compared with the preparation method of organic compound M1, the difference in the preparation method of organic compound M3 lies in that: in step S1.2, "3 mmol of diphenylamine" is replaced with "3 mmol of 4,4'-dimethoxydiphenylamine (CAS No. 101-70-2)". The NMR data of the prepared organic compound M3 are as follows: 1H NMR (500 MHz, Chloroform-d) δ 8.67 (s, 2H), 8.54 (s, 2H), 7.16 - 7.11 (m, 8H), 6.85 - 6.78 (m, 8H), 3.79 (s, 12H).

[0130] Example 4 of Organic Compound

[0131] This example provides an organic compound M4 and its preparation method. The synthetic route of organic compound M4 is as follows:

[0132]

[0133] Compared with the preparation method of organic compound M1, the difference in the preparation method of organic compound M4 lies in that: in step S1.2, "3 mmol of diphenylamine" is replaced with "3 mmol of 2-bromophenoxathiin (CAS No. 10230-35-0)". The NMR data of the prepared organic compound M4 are as follows: 1H NMR (500 MHz, Chloroform-d) δ 8.75 (s, 2H), 8.63 (s, 2H), 7.85 - 7.81 (m, 2H), 7.75 - 7.71 (m, 2H), 7.31 - 7.28 (m, 2H), 7.11 - 6.98 (m, 8H).

[0134] Example 5 of Organic Compound

[0135] This example provides an organic compound M5 and its preparation method. The synthetic route of organic compound M5 is as follows:

[0136]

[0137] Compared with the preparation method of organic compound M1, the difference in the preparation method of organic compound M5 lies in that: in step S1.2, "3 mmol of diphenylamine" is replaced with "3 mmol of 10-(4-bromophenyl)-10H-phenoxazine (CAS No. 71041-21-9)". The NMR data of the prepared organic compound M5 are as follows: 1H NMR (500 MHz, Chloroform-d) δ 8.74 (s, 2H), 8.62 (s, 2H), 7.84 - 7.81 (m, 4H), 7.42 - 7.38 (m, 4H), 7.20 - 7.16 (m, 4H), 7.04 - 6.96 (m, 8H), 6.95 - 6.91 (m, 4H).

[0138] Example 6 of Organic Compound

[0139] This example provides an organic compound M6 and its preparation method. The synthetic route of organic compound M6 is as follows:

[0140]

[0141] Compared with the preparation method of organic compound M1, the difference in the preparation method of organic compound M6 lies in that: in step S1.2, "3 mmol of diphenylamine" is replaced with "3 mmol of 9-(4-bromophenyl)carbazole (CAS No. 57102-42-8)". The NMR data of the prepared organic compound M6 are as follows: 1H NMR (500 MHz, Chloroform-d) δ 8.74 (s, 2H), 8.62 (s, 2H), 8.16 - 8.11 (m, 4H), 7.95 - 7.91 (m, 4H), 7.87 - 7.84 (m, 4H), 7.62 - 7.58 (m, 4H), 7.34 - 7.30 (m, 6H), 7.26 - 7.21 (m, 2H).

[0142] Organic compound Example 7

[0143] This example provides an organic compound M7 and its preparation method. The synthetic route of organic compound M7 is as follows:

[0144]

[0145] Compared with the preparation method of organic compound M1, the difference in the preparation method of organic compound M7 is that: in step S1.2, "3 mmol of diphenylamine" is replaced with "3 mmol of 4-bromo-4',4'-dimethoxytriphenylamine (CAS No. 194416-45-0)". The NMR data of the prepared organic compound M7 are as follows: 1H NMR (500 MHz, Chloroform-d) δ 8.72 (s, 2H), 8.60 (s, 2H), 7.76 - 7.72 (m, 4H), 7.16 - 7.14 (m, 4H), 7.12 - 7.09 (m, 8H), 6.85 - 6.80 (m, 8H), 3.78 (s, 12H).

[0146] Example 8 of Organic Compound

[0147] This example provides an organic compound M8 and its preparation method. The synthesis route of organic compound M8 is as follows:

[0148]

[0149] Compared with the preparation method of organic compound M1, the difference in the preparation method of organic compound M8 is that: in step S1.2, "3 mmol of diphenylamine" is replaced with "3 mmol of 10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydroacridine (CAS No. 1342892-15-2)". The NMR data of the prepared organic compound M8 are as follows: 1H NMR (500 MHz, Chloroform-d) δ 8.73 (s, 2H), 8.61 (s, 2H), 7.82 - 7.77 (m, 4H), 7.32 - 7.29 (m, 4H), 7.23 - 7.20 (m, 4H), 7.17 - 7.13 (m, 4H), 7.04 - 6.99 (m, 8H), 1.59 (s, 12H).

[0150] Example 9 of Organic Compound

[0151] This example provides an organic compound M9 and its preparation method. The synthesis route of organic compound M9 is as follows:

[0152]

[0153] Compared with the preparation method of organic compound M1, the difference in the preparation method of organic compound M9 is that: in step S1.2, "3 mmol of diphenylamine" is replaced with "3 mmol of 10-(4-bromophenyl)phenothiazine (CAS No. 63524-03-8)". The NMR data of the prepared organic compound M9 are as follows: 1H NMR (500 MHz, Chloroform-d) δ 8.74 (s, 2H), 8.62 (s, 2H), 7.85 - 7.80 (m, 4H), 7.45 - 7.37 (m, 8H), 7.24 - 7.16 (m, 8H), 7.08 - 7.02 (m, 4H).

[0154] Example 10 of Organic Compound

[0155] This example provides an organic compound M10 and its preparation method. The synthetic route of organic compound M10 is as follows:

[0156]

[0157] The synthetic method of organic compound M10 includes the steps: Take a 100 mL two-necked flask, add 1 mmol of compound M10-1 (CAS No. 6633-42-7), 5 mmol of sodium nitrite (CAS No. 7632-00-0), and 10 mL of acetic acid thereto. Dissolve the foregoing raw materials in 5 mL of deionized water, stir at room temperature for 30 min, stop the reaction when it is monitored that the raw materials have completely reacted, distill the reaction solution under reduced pressure to remove the solvent, mix the crude product with silica gel of 200 to 300 mesh, and then perform column chromatography separation. The mobile phase consists of petroleum ether and ethyl acetate (the volume ratio of petroleum ether to ethyl acetate is 1:1) to obtain compound M10 with a yield of 62%. The NMR data are as follows: 1H NMR (500 MHz, Chloroform-d) δ 8.67 - 8.63 (m, 2H), 7.80 - 7.76 (m, 1H), 7.72 - 7.68 (m, 1H), 7.53 - 7.50 (t m, 1H), 7.40 - 7.38 (m, 1H).

[0158] Example 11 of Organic Compound

[0159] This example provides an organic compound M11, and organic compound M11 is M1-2 in Example 1 of organic compounds.

[0160] Comparative Example 1 of Organic Compound

[0161] This comparative example provides an organic compound P1 and its preparation method. The synthetic route of organic compound P1 is as follows:

[0162]

[0163] The synthesis method of organic compound P1 includes the following steps: Take a 100 mL two-necked flask, add 1 mmol of compound P1-1 (CAS No. 14348-75-5) thereto, then add 40 mL of toluene. After compound P1-1 is dissolved in toluene, add 3 mmol of diphenylamine and 0.5 mmol of copper chloride. Introduce nitrogen, use a vacuum pump to evacuate and replace with nitrogen for 15 min. Wrap the two-necked flask containing the reaction system with tin foil, stir in the dark and heat to 110 °C for reaction for 24 h. Stop the reaction and cool to room temperature. Extract the reaction solution, and then repeat the washing treatment on the extraction phase 3 to 4 times. Each washing treatment is successively carried out with 1000 mL of dichloromethane and 250 mL of deionized water, and then use anhydrous magnesium sulfate to dry the organic phase obtained after the washing treatment, and then carry out rough separation by column chromatography. The eluent is a mixture composed of petroleum ether, dichloromethane and ethyl acetate, and the volume ratio of petroleum ether:dichloromethane:ethyl acetate is 20:1:1 to obtain organic compound M1. Organic compound M1 is a white solid with a yield of 70%. The nuclear magnetic detection data is: 1H NMR (500 MHz, Chloroform-d) δ 7.66 - 7.63 (m, 4H), 7.43 - 7.40 (m, 2H), 7.28 - 7.23 (m, 8H), 7.10 - 7.07 (m, 8H), 7.05 - 7.01 (m, 4H).

[0164] Organic compound Comparative Example 2

[0165] This comparative example provides an organic compound P2 and its preparation method. The synthesis route of organic compound P2 is as follows:

[0166]

[0167] Compared with the preparation method of organic compound P1, the difference in the preparation method of organic compound P2 is that: replace "3 mmol of diphenylamine" with "3 mmol of 4-(9H-carbazol-9-yl)phenylboronic acid (CAS No. 419536-33-7)". The nuclear magnetic data of the prepared organic compound P2 is: 1H NMR (500 MHz, Chloroform-d) δ 8.28 - 8.26 (m, 2H), 8.16 - 8.12 (m, 4H), 8.01 - 7.98 (m, 2H), 7.93 - 7.90 (m, 2H), 7.84 - 7.81 (m, 4H), 7.75 - 7.72 (m, 4H), 7.63 - 7.59 (m, 4H), 7.35 - 7.31 (m, 6H), 7.26 - 7.22 (m, 2H).

[0168] Organic compound Comparative Example 3

[0169] This comparative example provides an organic compound P3 and its preparation method. The synthetic route of the organic compound P3 is as follows:

[0170]

[0171] Compared with the preparation method of the organic compound P1, the difference in the preparation method of the organic compound P3 is that: "3 mmol of diphenylamine" is replaced by "3 mmol of 4-(9H-carbazol-9-yl)phenylboronic acid (CAS No. 1246021-63-5)". The NMR data of the prepared organic compound P3 are as follows: 1H NMR (500 MHz, Chloroform-d) δ 8.28 - 8.25 (m, 2H), 8.01 - 7.99 (m, 2H), 7.94 - 7.89 (m, 2H), 7.71 - 7.67 (m, 4H), 7.50 - 7.47 (m, 4H), 7.46 - 7.41 (m, 4H), 7.24 - 7.17 (m, 8H), 7.08 - 7.02 (m, 4H).

[0172] Device Example 1

[0173] This example provides an optoelectronic device and its preparation method. The optoelectronic device is a quantum dot light-emitting diode with a normal structure. As Figure 2 shown, the optoelectronic device 10 includes an anode 101, a functional layer 103, and a cathode 102 stacked in sequence. In the upward direction, the functional layer 103 includes a hole functional layer 1032, a light-emitting layer 1033, and an electron functional layer 1031 stacked in sequence. The hole functional layer 1032 is closer to the anode 101 than the electron functional layer 1031; the hole functional layer 1032 is composed of a hole injection layer 10321 and a hole transport layer 10322 stacked. The hole injection layer 10321 is closer to the anode 101 than the hole transport layer 10322; the electron functional layer 1031 is a single-layer structure. The light-emitting area of the optoelectronic device 10 is 0.04 cm 2 .

[0174] The materials and thicknesses of each layer in the optoelectronic device 10 are as follows:

[0175] The material of the anode 101 is ITO, and the average thickness of the anode 101 is 40 nm;

[0176] The material of the cathode 102 is Ag, and the average thickness of the cathode 102 is 20 nm;

[0177] The material of the light-emitting layer 1033 is CdSe (core) / ZnSe (intermediate shell) / ZnS (outer shell), the emission color is green, and the average thickness of the light-emitting layer 1033 is 30 nm;

[0178] The material of the electronic functional layer 1031 is nano-Zn 0.85 Mg 0.15 O (average particle size is 5 nm), and the average thickness of the electronic functional layer 1031 is 50 nm;

[0179] The material of the hole injection layer 10321 is PEDOT:PSS, and the average thickness of the hole injection layer 10321 is 40 nm;

[0180] The material of the hole transport layer 10322 is organic compound M1, and the average thickness of the hole transport layer 10322 is 20 nm.

[0181] The preparation method of the optoelectronic device in this embodiment includes the following steps:

[0182] S10.1. Provide a substrate, sputter ITO on one side of the substrate to obtain an ITO layer, wipe the surface of the ITO layer with a cotton swab dipped in a small amount of soapy water to remove visible impurities on the surface, and then ultrasonically clean the substrate including ITO in deionized water for 15 min, ultrasonically clean in acetone for 15 min, ultrasonically clean in ethanol for 15 min, and ultrasonically clean in isopropanol for 15 min. After drying, perform ultraviolet-ozone surface treatment for 20 min to obtain a substrate including an anode;

[0183] S10.2. Under the air environment of normal temperature and pressure, spin-coat an aqueous solution of PEDOT:PSS on the side of the anode away from the substrate, and then place it in a constant temperature heat treatment at 150 °C to cure into a film to obtain a hole injection layer;

[0184] S10.3. Under the nitrogen environment of normal temperature and pressure, spin-coat a solution of organic compound M1-chlorobenzene with a concentration of 8 mg / mL on the side of the hole injection layer away from the anode, and then place it in a constant temperature heat treatment in a nitrogen atmosphere at 120 °C to cure into a film to obtain a hole transport layer;

[0185] S10.4. Under the nitrogen environment of normal temperature and pressure, spin-coat a quantum dot-n-hexane solution with a concentration of 20 mg / mL on the side of the hole transport layer away from the hole injection layer, and then let it stand for 15 min in a nitrogen atmosphere environment with a pressure of 10 -2 MPa to cure into a film to obtain a light-emitting layer;

[0186] S10.5. Under the nitrogen environment of normal temperature and pressure, spin-coat a solution of nano-Zn 0.85 Mg 0.15 O-ethanol solution with a concentration of 30 mg / mL on the side of the light-emitting layer away from the hole transport layer, and then let it stand for 15 min in a nitrogen atmosphere environment with a pressure of 10 -2 MPa to cure into a film to obtain an electronic functional layer;

[0187] S10.6. Place the stacked structure completed in step S10.5 into an evaporation chamber with a vacuum degree not higher than 3×10 -4 Pa, thermally evaporate Ag on the side of the electronic functional layer away from the light-emitting layer using a thermal evaporation process to obtain a cathode, and then encapsulate it with a non-acid epoxy resin LOCTITE 3335 to obtain an optoelectronic device.

[0188] Device Example 2-11

[0189] Device Example n is basically the same as Device Example 1, with the main difference being that the materials of the hole transport layer are different. The material of the hole transport layer in Device Example n corresponds to the organic compound in Organic Compound Example n, where n is an integer from 2 to 11. For example, the material of the hole transport layer in Device Example 2 is the organic compound M2 in Organic Compound Example 2, and so on. The material of the hole transport layer in Device Example 11 is the organic compound M11 in Organic Compound Example 11.

[0190] Device Comparative Example 1-3

[0191] Device Comparative Example m is basically the same as Device Example 1, with the main difference being that the materials of the hole transport layer are different. The material of the hole transport layer in Device Comparative Example m corresponds to the organic compound in Organic Compound Comparative Example m, where m is an integer from 1 to 3. For example, the material of the hole transport layer in Device Comparative Example 1 is the organic compound P1 in Organic Compound Comparative Example 1, and so on. The material of the hole transport layer in Device Comparative Example 3 is the organic compound P3 in Organic Compound Comparative Example 3.

[0192] Experimental Example 1

[0193] Respectively use the organic compounds in Organic Compound Example 1 to Organic Compound Example 11 and Organic Compound Comparative Example 1 to Organic Compound Comparative Example 3 as hole transport materials, and refer to the preparation processes of the corresponding film layers in Device Example 1 above to construct a detection device with the following structure: ITO (average thickness of 40 nm) / organic compound layer (average thickness of 20 nm) / MoO3 layer (average thickness of 20 nm) / Ag (average thickness of 30 nm). Then use the detection device to detect the hole mobility of the materials, and the results are shown in Table 1.

[0194] The hole mobility of the hole transport material is recorded by the space charge limited current (SCLC) method, which can be described by the Mott-Gurney equation: J = 9με0ε r V 2 / (8d 3 ), where J is the current density, μ is the hole mobility, ε0 is the vacuum permittivity (8.85×10 -12 F / m), εr is the dielectric constant of the material (for organic semiconductors, it is usually approximately taken as 3), V is the applied voltage, and d is the average thickness of the organic compound layer.

[0195] Table 1

[0196]

[0197]

[0198] As can be seen from Table 1, the hole mobilities of organic compounds M1 to M11 are in the range of 3.0×10 -5 ~3.86×10 -5 cm 2 V -1 s -1 , and compared with the hole mobilities of organic compounds P1 to P3, the hole mobilities of organic compounds M1 to M11 are higher. For example, the hole mobility of organic compound M1 is 1.6 times that of organic compound P1.

[0199] This shows that organic compounds M1 to M11 have excellent hole transport properties and can be used as hole functional materials.

[0200] Experimental Example 2

[0201] The performances of the optoelectronic devices in the state of being encapsulated for 1 h in Device Examples 1 to 11 and Device Comparative Examples 1 to 3 were respectively detected. The performance tests were carried out in an environment with a temperature of 25°C and a relative humidity of 40%.

[0202] The detection of the optoelectronic properties was carried out using a FushiDa FPD optical property measurement device (including an efficiency test system built with components such as Ocean Optics USB2000, LabView-controlled QE-PRO spectrometer, Keithley 2400, high-precision digital source meter Keithley 6485, optical fiber with an inner diameter of 50 μm, device test probes and fixtures, various related connecting wires and data cards, efficiency test dark box, and data acquisition system) to obtain parameters such as the turn-on voltage, current, brightness, and emission spectrum of each optoelectronic device, and then calculate and obtain key parameters such as the external quantum efficiency and power efficiency, and obtain the maximum brightness (L max , cd / m 2 ).

[0203] Among them, the detection method of the current efficiency includes the steps: setting the light-emitting area to 2 mm × 2 mm = 4 mm 2, discontinuously collect the brightness values of the optoelectronic device within the voltage range of 0V to 8V, collect once every 0.2V, and divide the brightness value collected each time by the corresponding current density to obtain the current efficiency of the optoelectronic device under the collection conditions of this time, and obtain the maximum current efficiency (C.E max , %).

[0204] The detection method of the device life includes the steps: under the drive of a constant current (2mA), use the life test equipment to perform electroluminescence life analysis on each optoelectronic device, record the time (T95, h) required for each optoelectronic device to decay from the maximum brightness to 95%, and then obtain the device life (T95@1000nit, h) at a brightness of 1000nit through the extended exponential decay brightness decay fitting formula. The specific calculation formula is as follows:

[0205]

[0206] Among them, T95 L is the life at low brightness, T95 H is the measured life at high brightness, L H is the device accelerated to the highest brightness, L L is 1000nit, A is the acceleration factor, and the value of A is 1.7.

[0207] The method for stability test is: obtain C.E max as the initial current efficiency of each optoelectronic device according to the detection method of the foregoing current efficiency, and then place each optoelectronic device in a closed environment of a standard ultraviolet light source (350nm) respectively, and irradiate the optoelectronic device continuously at a power of 100mW / cm 2 for 6h, and then use the detection method of the foregoing current efficiency to obtain the maximum current efficiency C.E1 after UV irradiation, and calculate the attenuation rate (the calculation formula is 100% - C.E1 / C.E max ×100%, take the absolute value of the foregoing calculation result), which is characterized as light stability.

[0208] The performance detection results of each optoelectronic device are shown in Table 2 below:

[0209] Table 2

[0210]

[0211] As can be seen from Table 2, compared with the comprehensive performance of the optoelectronic devices in Device Comparative Example 1 to Device Comparative Example 3, the comprehensive performance of the optoelectronic devices in Device Example 1 to Device Example 11 has significant advantages, specifically manifested as: the optoelectronic devices in Device Example 1 to Device Example 11 have higher L max , longer device life, better device efficiency and better performance stability.

[0212] It can be seen from this that the material of the hole functional layer includes the organic compound represented by the general formula (I), which can improve the optoelectronic performance, device life and performance stability of optoelectronic devices. The reasons are as follows: First, the organic compound represented by the general formula (I) has better hole transport / injection performance, effectively improving the problem of unbalanced electron-hole transport existing in QLED devices; Second, the organic compound represented by the general formula (I) has ultraviolet absorption performance, which can avoid or reduce the negative impact of ultraviolet light on the performance of the hole functional layer, making the hole functional layer have good performance stability and improving the performance stability of optoelectronic devices; Third, the organic compound represented by the general formula (I) uses fluorenone as the core structure, has high molecular planarity, improves the energy level matching degree between the hole functional layer and the light-emitting layer, and endows the hole functional layer with good morphological characteristics.

[0213] The above has introduced in detail an organic compound, a composition and an optoelectronic device provided by the embodiments of the present application. 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 technical solution and its core idea of the present application; those of ordinary skill in the art should understand that they can still modify the technical solutions recorded in the foregoing embodiments, or perform equivalent replacements on some of the technical features; and these modifications or replacements do not cause the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of the present application.

Claims

1. An organic compound, characterized in that, The organic compound has a structure represented by the following general formula (I): In general formula (I), are each independently selected from & represents the fusion site with ; are respectively absent or selected from and at least one of them is present, where * represents the connecting site with R1 or R2; R1 and R2 are each absent or are each independently selected from groups having structures represented by the following formula (2-1) or formula (2-2): In formula (2-1), X is selected from O, S, SiR5R6, CR7R8 or NR9, and R5 to R9 are each independently selected from -H, -D, -NR 10 R 11 , a halogen group, a hydroxyl group, a mercapto group, a nitro group, a sulfonic acid group, an aldehyde group, a cyano group, an unsubstituted or at least one substituent-substituted C1-C30 linear alkyl group, an unsubstituted or at least one substituent-substituted C1-C30 linear alkoxy group, an unsubstituted or at least one substituent-substituted aryl group having 6 to 30 ring atoms, or an unsubstituted or at least one substituent-substituted heteroaryl group having 5 to 30 ring atoms, or a combination of these groups; In formula (2-2), Y-* is selected from N-* or N-R 12 -*, R 12 is selected from a linear alkylene group having 1 to 30 carbon atoms, a linear alkoxy group having 1 to 30 carbon atoms, an arylene group having 6 to 14 ring atoms, a heteroarylene group having 5 to 14 ring atoms, or a combination of these groups; R3 and R4 are each independently selected from a single bond, -H, -D, hydroxyl group, mercapto group, -NR 10 R 11 , unsubstituted or substituted by at least one substituent C1-C30 linear alkyl group, or unsubstituted or substituted by at least one substituent C1-C30 linear alkoxy group, or a combination of these groups, there is no connection between adjacent R3 and R4, or adjacent R3 and R4 are connected to form a cyclic structure with X or Y; R 10 and R 11 each occurrence is independently selected from -H, -D, a linear alkyl group having 1 to 30 carbon atoms, a linear alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 14 ring atoms; Each occurrence of the substituent is independently selected from -D, a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms, or an aryl group having 6 to 14 ring atoms; n1 and n2 are each independently selected from integers from 0 to 5.

2. The organic compound according to claim 1, wherein The organic compound has a structure represented by any one of the following formulas (3-1) to (3-10):

3. The organic compound according to claim 1, wherein R5 to R9 are each independently selected from a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms, or a phenyl group; and / or R 12 a linear alkylene group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms, or a phenylene group; and / or R3 and R4 are each independently selected from a single bond, -H, -D, hydroxyl, mercapto, -NR 10 R 11 , a C1-C10 linear alkyl group, a C1-C10 linear alkoxy group, or a phenyl group; and / or R 10 and R 11 are each independently selected from -H, -D, a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms, or a phenyl group; and / or A *-* bond, *-S-* bond, *-O-* bond, *-CR 13 R 14 -* bond or *-NR 15 -* bond is formed by connecting adjacent R3 and R4, where "-" represents a single bond, and R 13 、R 14 and R 15 are each independently selected from linear alkyl groups having 1 to 10 carbon atoms or phenyl groups.

4. The organic compound according to any one of claims 1 to 3, characterized in that, R1 and R2 are each independently selected from groups represented by any one of the following formulas (1-1) to (1-13):

5. The organic compound according to claim 4, characterized in that, The organic compound has a structure represented by any one of the following structural formulas:

6. A method for preparing an organic compound, characterized in that, For preparing the organic compound according to any one of claims 1 to 5, the preparation method of the organic compound comprises the following steps: (A1) Using a first compound as a raw material, carrying out a ring-closure reaction to obtain a second compound; and (A2) Mixing the second compound with a third compound and carrying out a nitrogen-nitrogen coupling reaction to obtain an organic compound having a structure represented by the general formula (I); wherein the first compound has a structure represented by the following formula (4-1): The second compound has a structure represented by the following formula (4-2): The general formula of the third compound is Ar-Z, wherein Ar represents R1 or R2. When the atom in Ar connected to Z is an N atom, Z is -H; when the atom in Ar connected to Z is a non-N atom, Z is a halogen group.

7. The preparation method according to claim 6, characterized in that, The step (A1) comprises the steps of: mixing the first compound, sodium nitrite, acetic acid and water to carry out the ring-closure reaction; wherein the molar ratio of the first compound to sodium nitrite is 1:(5 to 20), and / or the temperature of the ring-closure reaction is 20°C to 30°C, and / or the time of the ring-closure reaction is 10 min to 60 min.

8. The preparation method according to claim 6, characterized in that, In the step (A2), the molar ratio of the second compound to the third compound is 1:(3 to 5), and / or the temperature of the nitrogen-nitrogen coupling reaction is 80°C to 110°C, and / or the time of the nitrogen-nitrogen coupling reaction is 6 h to 24 h.

9. A composition, characterized in that, The composition comprises a solvent and the organic compound according to any one of claims 1 to 5, or an organic compound prepared by the preparation method according to any one of claims 6 to 8.

10. The composition according to claim 9, wherein The solvent is selected from one or more of alkanes, aromatic hydrocarbons, halogenated alkanes, alcohol compounds, ether compounds, furan compounds, pyridine compounds, amide compounds, ester compounds, and sulfone compounds; optionally, the solvent is selected from one or more of toluene, chlorobenzene, chloroform, tetralin, and chloronaphthalene; and / or The composition further includes a hole functional material, which is selected from one or more of an organic material, a first inorganic compound material, and a second inorganic compound material; the organic material is selected from one or more of poly(3,4-ethylenedioxythiophene):poly(styrenesulfonic acid), copper phthalocyanine, titanium oxyphthalocyanine, 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene, polypyrrole, polyaniline, 3-hexyl-substituted polythiophene, poly(9-vinylcarbazole), 4,4'-bis(9-carbazolyl)biphenyl, poly[bis(4-phenyl)(4-butylphenyl)amine], 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline], poly[(9,9-dioctylfluorene-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)], poly[(N,N'-(4-n-butylphenyl)-N,N'-diphenyl-1,4-phenylenediamine)-ALT-(9,9-din-octylfluorene-2,7-diyl)], 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, 4,4',4''-tris(carbazol-9-yl)triphenylamine, 4,4',4'-tris(2-naphthylphenylamino)triphenylamine, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine, N,N'-bis[4-(diphenylamino)phenyl]-N,N'-diphenylbenzidine, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-9,9-spirobifluorene-2,7-diamine, N2,N7-di-1-naphthyl-N2,N7-diphenyl-9,9'-spirobi[9H-fluorene]-2,7-diamine, poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine], and 2,2',7,7'-tetra[N,N-bis(4-methoxyphenyl)amino]-9,9'-spirobifluorene; and / or, the first inorganic compound material is selected from one or more of graphene, C60, nickel oxide, molybdenum oxide, tungsten oxide, vanadium oxide, p-type gallium nitride, chromium oxide, copper oxide, copper sulfide, molybdenum sulfide, and tungsten sulfide; and / or, the second inorganic compound material includes one or more doped second inorganic compounds, the host material of the doped second inorganic compound is selected from graphene, C60, nickel oxide, molybdenum oxide, tungsten oxide, vanadium oxide, p-type gallium nitride, chromium oxide, copper oxide, copper sulfide, molybdenum sulfide, or tungsten sulfide, and the doping element of the doped second inorganic compound is selected from one or more of nickel, molybdenum, tungsten, vanadium, chromium, copper, and platinum group metal elements.

11. An optoelectronic device, characterized in that, Comprising: An anode and a cathode which are oppositely arranged; And A functional layer disposed between the anode and the cathode; Among them, the functional layer includes a hole functional layer, and the material of the hole functional layer includes the organic compound described in any one of claims 1 to 5, or the organic compound prepared by the preparation method described in any one of claims 6 to 8, or the hole functional layer is prepared from the composition described in claim 9 or 10.

12. The optoelectronic device according to claim 11, wherein, The hole functional layer includes a hole injection layer and a hole transport layer which are stacked, the hole injection layer is closer to the anode than the hole transport layer, and the material of the hole transport layer includes the organic compound described in any one of claims 1 to 5, or the organic compound prepared by the preparation method described in any one of claims 6 to 8, or the hole transport layer is prepared from the composition described in claim 9 or 10; and / or The functional layer further includes a light-emitting layer, the light-emitting layer is disposed between the hole functional layer and the cathode, and the material of the light-emitting layer includes one or more of an organic light-emitting material and a light-emitting quantum dot; and / or The functional layer further includes an electron functional layer, and the electron functional layer is disposed between the hole functional layer and the cathode.

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