Organic compound, application thereof, composition and photoelectric device

Abstract

The invention discloses an organic compound as well as application, a composition and a photoelectric device thereof. The organic compound has a structure as shown in a formula (I). The organic compound disclosed by the invention has relatively high electron transmission capability.

Description

Technical Field

[0001] This application relates to the field of organic materials technology, and in particular to an organic compound and its applications, compositions, and optoelectronic devices. Background Technology

[0002] Electron transport materials are materials that possess electron transport properties. Currently, commonly used electron transport materials include organic and inorganic electron transport materials. Phenoxazine organic compounds, with their excellent electron mobility and superior energy level matching, are used as organic electron transport materials.

[0003] However, due to the butterfly-shaped structure of the nitrogen atom in phenoxazine, its molecular planarity is poor, which limits its charge transport ability to phenoxazine organic compounds. Summary of the Invention

[0004] In view of this, this application provides an organic compound, its application, a composition, and an optoelectronic device.

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

[0006]

[0007] Where n' and n” are each an independent integer from 1 to 4;

[0008] R1 is selected from H, D, and substituted or unsubstituted C1-C1. 30 Alkyl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C1-C 30 alkoxy, substituted or unsubstituted C1-C 30 One or more combinations of alkylthio, aryl with 6 to 60 substituted or unsubstituted ring atoms, aryloxy with 6 to 60 substituted or unsubstituted ring atoms, and heteroaryl with 5 to 60 substituted or unsubstituted ring atoms;

[0009] Ar1 and Ar2 are each independently selected from one or more combinations of aryl groups with 6 to 60 cyclic atoms and heteroaryl groups with 5 to 60 cyclic atoms, whether substituted or unsubstituted.

[0010] Each of the substituents mentioned herein is independently selected from D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C1 groups, each time it appears. 20 Alkyl, C1-C 20 The heteroaryl group is selected from one or more of alkoxy groups and aryl groups having a ring number of 6 to 20; the heteroatom of the heteroaryl group is selected from one or more of O, N, S, P, and Si.

[0011] Secondly, embodiments of this application also provide an application of the above-mentioned organic compound in the field of optoelectronics.

[0012] Thirdly, embodiments of this application also provide a composition comprising a solvent and the organic compound.

[0013] Fourthly, embodiments of this application also provide an optoelectronic device comprising the aforementioned organic compound.

[0014] The organic compounds described in this application have high electron transport capabilities. Attached Figure Description

[0015] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0016] Figure 1 This is a flowchart illustrating a method for preparing an organic compound provided in an embodiment of this application;

[0017] Figure 2 This is a schematic diagram of the structure of an optoelectronic device provided in an embodiment of this application;

[0018] Figure 3 This is a schematic diagram of another optoelectronic device provided in the embodiments of this application.

[0019] Figure label:

[0020] Optoelectronic device 100; anode 10; electron transport layer 20; cathode 30; hole transport layer 40; light-emitting layer 50; hole injection layer 60. Detailed Implementation

[0021] The technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of this application, and not all embodiments. Based on the embodiments of this application, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this application. Furthermore, it should be understood that the specific embodiments described herein are only for illustration and explanation of this application and are not intended to limit this application.

[0022] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used herein in the specification of this invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0023] In this application, unless otherwise stated, directional terms such as "upper" and "lower" generally refer to the upper and lower positions of the device in its actual use or operating state, specifically the drawing directions in the accompanying drawings; while "inner" and "outer" refer to the outline of the device. Furthermore, in the description of this application, the term "comprising" means "including but not limited to". The terms first, second, third, etc., are used merely as illustrative purposes and do not impose numerical requirements or establish a numerical order.

[0024] In this application, "and / or" describes the relationship between related objects, indicating that three relationships can exist. For example, A and / or B can represent: A existing alone, A and B existing simultaneously, or B existing alone. A and B can be singular or plural.

[0025] In this application, "at least one" means one or more, and "more than one" means two or more. "At least one," "at least one of the following," or similar expressions refer to any combination of these items, including any combination of single or multiple items. For example, "at least one of a, b, or c," or "at least one of a, b, and c," can both mean: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, and c can be single or multiple.

[0026] In this application, the term "on" forming another layer on a certain layer is a broad concept. It can mean that the formed another layer is adjacent to a certain layer, or it can mean that there are other spacer structures between the other layer and the certain layer. For example, when a cathode is formed "on" the first carrier functional layer, the term "on" can mean that the formed cathode is adjacent to the first carrier functional layer, or it can mean that there are other spacer structures between the cathode and the first carrier functional layer, such as a light-emitting layer.

[0027] Various embodiments of this application may exist in the form of a range; it should be understood that the description in the form of a range is merely for convenience and brevity and should not be construed as a hard limitation on the scope of this application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single numerical 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 single numbers within the range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. Furthermore, whenever a numerical range is referred to herein, it means including any referenced number (fraction or integer) within the referred range.

[0028] In this application, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0029] In this application, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0030] In this application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. It can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl, and for polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" means an aryl containing 6 to 40 ring atoms, and the aryl may optionally be further substituted. Preferably, it is a substituted or unsubstituted aryl having 6 to 30 ring atoms; more preferably, it is a substituted or unsubstituted aryl having 6 to 18 ring atoms; particularly preferably, it is a substituted or unsubstituted aryl having 6 to 14 ring atoms, and the aryl may optionally be further substituted. Suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl, and their derivatives. Understandably, 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), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, and diaryl ether systems should also be included in the definition of aryl.

[0031] In this application, "heteroaryl or heteroaromatic group" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, O atom, S atom, Si atom, P atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group may optionally be further substituted; suitable examples include, but are not limited to: thiophene, furanyl, pyrrole, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, etc. Triazinyl, acridineyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidineyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrololyl, thienopyrrololyl, thienopyrrololyl, furanolololyl, furanolofuranyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridineyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0032] In this application, "alkyl" can mean straight-chain, branched, and / or cyclic alkyl. The number of carbon atoms in an alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, such as "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each time it appears, it can independently be a C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, etc. tert-amyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl The compounds include 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-pentadecanyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-hepta ...

[0033] In this application, "-C" n H 2n+1 "Unless otherwise specified or limited, it indicates a straight-chain alkyl group. For example, -C4H9 indicates n-butyl."

[0034] In this application, "alkoxy" refers to a group with the structure "-O-alkyl", that is, an alkyl group as defined above that is attached to other groups via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-OC(CH3)3 or -Ot-Bu).

[0035] In this application, * indicates a connectable site.

[0036] In this application, the single bonds connecting the substituents extend through the corresponding ring, indicating that the substituent can be connected to any position on the ring. For example... Ar1 can be attached to any substituted site in the benzene ring.

[0037] The terms “combinations thereof,” “any combination thereof,” and “any combination thereof” as used in this application include all suitable combinations of any two or more of the listed items.

[0038] The technical solution of this application is as follows:

[0039] In a first aspect, embodiments of this application provide an organic compound, which is a dibenzothiophenexaazine organic compound having the structure shown in formula (I):

[0040]

[0041] Where n' and n” are each an independent integer from 1 to 4;

[0042] R1 can be selected from, but is not limited to, H, D, substituted or unsubstituted C1 to C1. 30 Alkyl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C1-C 30 alkoxy, substituted or unsubstituted C1-C 30 One or more combinations of alkylthio, aryl with 6 to 60 substituted or unsubstituted ring atoms, aryloxy with 6 to 60 substituted or unsubstituted ring atoms, and heteroaryl with 5 to 60 substituted or unsubstituted ring atoms;

[0043] Ar1 and Ar2 are each independently selected from, but not limited to, one or more combinations of aryl groups with 6 to 60 cyclic atoms and heteroaryl groups with 5 to 60 cyclic atoms, whether substituted or unsubstituted.

[0044] It is understandable that Ar1 and Ar2 may be the same or different.

[0045] It should be noted that when the above groups are substituted by substituents, each substituent is independently selected from D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C1 groups. 20 Alkyl, C1-C 20 One or more combinations of alkoxy groups and aryl groups having 6 to 20 ring atoms.

[0046] It should be noted that the heteroatoms of the heteroaryl group in this application are selected from one or more of O, N, S, P, and Si.

[0047] In some embodiments, Ar1 and Ar2 are each independently selected from, but not limited to, heteroaryl groups with 5 to 60 ring atoms. On the one hand, the heteroaryl group has a conjugated structure of an aromatic ring, which can effectively bring about electron transfer and is beneficial to electron transport; on the other hand, the lone pair electrons of the heteroatom in the heteroaryl group can effectively enhance the electron-richness of its aromatic ring, further facilitating electron transport.

[0048] In some embodiments, the organic compound has the structure shown in formula (II):

[0049]

[0050] In some embodiments, R1 may be selected from, but is not limited to, H, D, substituted or unsubstituted C1 to C2. 20 Alkyl, substituted or unsubstituted C3-C 20 cycloalkyl, substituted or unsubstituted C1-C 20 alkoxy, substituted or unsubstituted C1-C 20 It is one or more combinations of alkylthio, aryl with 6 to 30 substituted or unsubstituted ring atoms, aryloxy with 6 to 30 substituted or unsubstituted ring atoms, and heteroaryl with 5 to 30 substituted or unsubstituted ring atoms.

[0051] Furthermore, in some embodiments, R1 may be selected from, but is not limited to, H, D, substituted or unsubstituted C1 to C2. 15 Alkyl, substituted or unsubstituted C3-C 15 cycloalkyl, substituted or unsubstituted C1-C 15 alkoxy, substituted or unsubstituted C1-C 15 It is one or more combinations of alkylthio, aryl with 6 to 20 substituted or unsubstituted ring atoms, aryloxy with 6 to 20 substituted or unsubstituted ring atoms, and heteroaryl with 5 to 20 substituted or unsubstituted ring atoms.

[0052] Furthermore, in some embodiments, R1 may be selected from, but is not limited to, H, D, substituted or unsubstituted C1 to C2. 15 Alkyl, substituted or unsubstituted C3-C 15 cycloalkyl, substituted or unsubstituted C1-C 15 alkoxy, substituted or unsubstituted C1-C 15 It is one or more combinations of alkylthio, aryl with 6 to 15 substituted or unsubstituted ring atoms, aryloxy with 6 to 15 substituted or unsubstituted ring atoms, and heteroaryl with 5 to 15 substituted or unsubstituted ring atoms.

[0053] To better control the electron mobility of the organic compound, the terminal substituents Ar1 and Ar2 can be optimized.

[0054] In some embodiments, Ar1 and Ar2 are each independently selected from one of the following structures:

[0055]

[0056] Wherein, n1 and n2 are each independently selected from integers from 0 to 5, for example, they can be selected from 0, 1, 2, 3, 4 or 5. n1 and n2 can be the same or different.

[0057] n3 and n4 are each independently selected from integers from 0 to 4. For example, they can be selected from 0, 1, 2, 3 or 4. n3 and n4 can be the same or different.

[0058] n5 and n6 are each independently selected from integers from 0 to 4. For example, they can be selected from 0, 1, 2, 3 or 4. n5 and n6 can be the same or different.

[0059] M is selected from SiR8, SiR8R9, and NR. 10 NR 16 , O or S;

[0060] X is selected from SiR 11 SiR 11 R 12 CR 13 R 14 S, O, N or NR 15 .

[0061] Among them, R2 to R7 are each independently selected from substituted or unsubstituted C1 to C7. 30 Alkyl, substituted or unsubstituted C1-C 30 When a combination of one or more of the following groups—alkoxy, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, and aryl groups having 6 to 20 ring atoms—is substituted, each substituent is independently selected from D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1 to C2. 20 Alkyl, C1-C 20 A combination of one or more of alkoxy groups and aryl groups having 6 to 20 ring atoms;

[0062] Among them, R8 to R 15 Each is independently selected from H, D, substituted or unsubstituted C1 to C2. 30The alkyl group, or a combination of one or more aryl groups having 6 to 60 substituted or unsubstituted ring atoms, wherein each substituted group is independently selected from D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1 to C2. 20 Alkyl, C1-C 20 A combination of one or more of alkoxy groups and aryl groups having 6 to 20 ring atoms;

[0063] R 16 Selected from substituted or unsubstituted C1 to C2 30 The alkylene group, or a combination of one or more arylene groups having 6 to 60 substituted or unsubstituted ring atoms, wherein each substituent is independently selected from D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1 to C2. 20 Alkyl, C1-C 20 One or more combinations of alkoxy groups and aryl groups having 6 to 20 ring atoms.

[0064] In some embodiments, R2 to R7 are each independently selected from C1 to C2. 30 Alkyl, C1-C 30 One or more combinations of alkoxy, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, and aryl groups having 6 to 20 ring atoms.

[0065] In other embodiments, R2 to R7 are each independently selected from C1 to C2. 20 Alkyl, C1-C 20 One or more combinations of alkoxy, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, and aryl groups having 6 to 15 ring atoms.

[0066] In some other embodiments, R2 to R7 are each independently selected from C1 to C2. 15 Alkyl, C1-C 15 One or more combinations of alkoxy, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, and aryl groups having 6 to 10 ring atoms.

[0067] In some embodiments, R8 to R 15 Each is independently selected from H, D, C1 to C 30 One or more of alkyl groups and aryl groups having 6 to 60 cyclic atoms.

[0068] In other embodiments, R8 to R 15 Each is independently selected from H, D, C1 to C 20 One or more of alkyl groups and aryl groups having 6 to 10 cyclic atoms.

[0069] In some other embodiments, R8 to R 15 Each is independently selected from H, D, C1 to C 10 One or more of alkyl groups and aryl groups having 6 to 10 cyclic atoms.

[0070] In some other embodiments, R8 to R 15 Each is independently selected from H, D, C1 to C 10 A combination of one or more alkyl groups and phenyl groups.

[0071] In some embodiments, R 16 Selected from C1 to C 30 One or more combinations of alkylene groups and arylene groups having 6 to 60 cyclic atoms.

[0072] In some embodiments, R 16 Selected from C1 to C 20 One or more combinations of alkylene groups and arylene groups having 6 to 30 cyclic atoms.

[0073] In some embodiments, R 16 Selected from C1 to C 10 One or more combinations of alkylene groups and arylene groups having 6 to 10 cyclic atoms.

[0074] In some embodiments, Ar1 and Ar2 are each independently selected from one of the following structures:

[0075]

[0076]

[0077] Furthermore, in some implementations, Ar1 and Ar2 are each independently selected from one of the following structural formulas (1) to (13):

[0078]

[0079]

[0080] R2 to R7 are each independently selected from one or more combinations of C1-C6 alkyl, C1-C6 alkoxy, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, and aryl with 6 to 10 ring atoms;

[0081] n1 and n2 are each independently selected from integers from 0 to 5, and n3, n4, n5, and n6 are each independently selected from integers from 0 to 4.

[0082] Furthermore, in some embodiments, Ar1 and Ar2 are each independently selected from one of the following structural formulas (1-1) to (1-13):

[0083]

[0084] As an example, the organic compound may be selected from, but is not limited to, any one of the compounds shown in formulas M1 to M15:

[0085]

[0086]

[0087] The phenoxazine unit in the organic compound described in this application has good mobility, and the benzothiophene unit in the organic compound can effectively enhance the conjugated planarity of the organic compound. Under the synergistic effect of the phenoxazine and the two benzothiophene units connected to the two phenyl groups of the phenoxazine, the organic compound has high electron transport capability.

[0088] Secondly, please refer to Figure 1 This application also provides a method for preparing an organic compound, wherein the synthetic route of the organic compound is as follows:

[0089]

[0090] Please refer to the following: Figure 1 The method for preparing the organic compound includes the following steps:

[0091] Step S11: Mix compound 1 with compound a and carry out a carbon-carbon coupling reaction to obtain compound 2;

[0092] Step S12: Compound 2 undergoes a ring-closing reaction to obtain compound 3;

[0093] Step S13: Compound 3 is subjected to a halogenation reaction with a halogenating agent to obtain compound 4;

[0094] Step S14: Mix compound 4 with compound ArY and carry out a carbon-carbon coupling reaction to obtain the organic compound.

[0095] In step S11:

[0096] The molar ratio of compound 1 to compound a is 1:(2-4), for example, 1:2, 1:2.5, 1:3, 1:3.5, 1:4, etc.

[0097] In some embodiments, after mixing compound 1 with compound a, a first catalyst is added to promote the carbon-carbon coupling reaction between compound 1 and compound a.

[0098] Understandably, the first catalyst is a known catalyst for promoting carbon-carbon coupling reactions between organic compounds, such as including but not limited to tetraphenylphosphine palladium.

[0099] In some embodiments, the molar ratio of compound 1 to the first catalyst is 1:(0.05–0.15), for example, 1:0.05, 1:0.06, 1:0.08, 1:0.10, 1:0.12, 1:0.13, 1:0.15, etc. Within this range, it exhibits good catalytic effect.

[0100] In some embodiments, the carbon-carbon coupling reaction between compound 1 and compound a is carried out at a temperature of 100–120°C, for example, 100°C, 105°C, 110°C, 115°C, 120°C, etc., and for a reaction time of 18–30 h, for example, 18 h, 20 h, 22 h, 23 h, 25 h, 26 h, 28 h, 30 h, etc. Within this temperature and time range, the carbon-carbon coupling reaction is facilitated to proceed rapidly and completely.

[0101] In step S12:

[0102] Compound 2 undergoes a ring-closing reaction under a second catalyst.

[0103] In some embodiments, the second catalyst includes, but is not limited to, palladium dichloride.

[0104] In some embodiments, the molar ratio of compound 2 to the second catalyst is 1:(0.05–0.15), for example, 1:0.05, 1:0.06, 1:0.08, 1:0.10, 1:0.12, 1:0.13, 1:0.15, etc. Within this range, it exhibits good catalytic effect.

[0105] In some embodiments, the reaction temperature for the ring-closure reaction of compound 2 is 120–150°C, for example, 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, 150°C, etc., and the reaction time is 12–24 h, for example, 12 h, 13 h, 15 h, 16 h, 18 h, 20 h, 21 h, 22 h, 23 h, 24 h, etc. Within the aforementioned temperature and time range, it is beneficial for the ring-closure reaction to proceed rapidly and completely.

[0106] In step S13:

[0107] In some embodiments, the halogenation reaction of compound 3 with a halogenating agent to obtain compound 4 includes:

[0108] a. The compound 2 is mixed with a first halogenating agent and reacted at a first temperature to obtain an intermediate;

[0109] b. The intermediate is mixed with a second halogenating agent and reacted at a second temperature to obtain compound 4.

[0110] In some embodiments, the first halogenating agent includes, but is not limited to, one or more of the following: monobromohexane, monochlorohexane, monoiodohexane, 1-bromo-n-octane, hexoxyiodobenzene, p-decoxybromobenzene, 1-bromododecane, bromocyclohexane, 1-bromobenzene, 1-bromo-3-methoxypropane, and 4-bromopyridine.

[0111] In some embodiments, the molar ratio of compound 3 to the first halogenator is 1:(1-4), for example, 1:1, 1:1.5, 1:2, 1:2.5, 1:3, 1:3.5, 1:4, etc.

[0112] In some embodiments, the first temperature is 80 to 110°C, for example, 80°C, 90°C, 100°C, 110°C, and the reaction time at the first temperature is 3 to 12 hours, for example, 3 hours, 5 hours, 6 hours, 8 hours, 10 hours, 12 hours, etc.

[0113] In some embodiments, the second halogenating agent includes, but is not limited to, N-halosuccinimide. Further, the N-halosuccinimide includes, but is not limited to, one or more of N-bromosuccinimide (NBS), N-iodosuccinimide (NCS), and N-iodosuccinimide.

[0114] In some embodiments, the molar ratio of compound 3 to the second N-halosuccinimide is 1:(2-4), for example, 1:2, 1:2.5, 1:3, 1:3.5, 1:4, etc.

[0115] In some embodiments, the second temperature is -10 to 30°C, such as -10°C, -5°C, 0°C, 5°C, 10°C, 15°C, 20°C, 25°C, 30°C, etc., and the reaction time at the second temperature is 0.5 to 6 hours, such as 0.5 hours, 1 hour, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, etc.

[0116] In compound 4, X1 and X2 are selected from halogen groups. Specifically, X is adjusted according to the type of halogenating agent used in step S13. For example, when the halogenating agent is a brominating agent, X is Br; when the halogenating agent is a chlorinating agent, X is Cl; and when the halogenating agent is an iodizing agent, X is I.

[0117] In step S14:

[0118] The ArY can be an aromatic hydrocarbon or a heteroaromatic hydrocarbon.

[0119] The Ar in ArY can be selected from, but is not limited to, one or more of Ar1 and Ar2 mentioned above, which will not be elaborated here.

[0120] As an example, in some embodiments, the ArY may be selected from, but is not limited to, one or more of diphenylamine, 4-bromotriphenylamine, 4,4'-dimethoxydiphenylamine, 2-bromophenoxazine, 10-(4-bromophenyl)-10H-phenoxazine, 9-(4-bromophenyl)-9H-carbazole, bisN-(4-bromophenyl)-4-methoxy-N-(4-methylphenyl)aniline, 10-(4-bromophenyl)-9,10-dihydro-9,9-dimethylacridine, and 10-(4-bromophenyl)-10H-phenthiazine.

[0121] In some embodiments, the molar ratio of compound 4 to compound ArY is 1:(2-4), for example, 1:2, 1:2.5, 1:3, 1:3.5, 1:4, etc.

[0122] In some embodiments, the reaction temperature for the carbon-carbon coupling reaction between compound 4 and compound ArY is 80–110°C, for example, 80°C, 85°C, 90°C, 95°C, 100°C, 105°C, 110°C, etc., and the reaction time is 12–24 h, for example, 12 h, 13 h, 14 h, 15 h, 16 h, 17 h, 18 h, 19 h, 20 h, 21 h, 22 h, 23 h, 24 h, etc.

[0123] Thirdly, embodiments of this application provide an application of the organic compound described above in the field of optoelectronics.

[0124] Fourthly, embodiments of this application provide a composition comprising a solvent and the organic compound described above.

[0125] The solvent may be selected from, but is not limited to, one or more of benzene, toluene, xylene, chlorobenzene, bromobenzene, methylphenol, and styrene.

[0126] In some embodiments, the concentration of the organic compound in the composition ranges from 10 to 40 mg / mL, for example, 10 mg / mL, 15 mg / mL, 20 mg / mL, 25 mg / mL, 30 mg / mL, 35 mg / mL, 40 mg / mL, etc.

[0127] In some embodiments, the composition may contain one or more of the above-described organic compounds.

[0128] Fifthly, please refer to Figure 2 This application provides an optoelectronic device 100, which includes the organic compounds described above.

[0129] In some embodiments, the optoelectronic device 100 includes an anode 10, an electron transport layer 20, and a cathode 30 stacked sequentially. The material of the electron transport layer 20 includes the organic compounds described above.

[0130] The optoelectronic device 100 described in this application includes the organic compound, which has strong electron transport properties, enabling the optoelectronic device 100 to have high luminous efficiency and long lifespan.

[0131] Please see Figure 3 The optoelectronic device 100 further includes a hole transport layer 40, which is located between the electron transport layer 20 and the anode 10.

[0132] The optoelectronic device 100 further includes a light-emitting layer 50, which is disposed between the electron transport layer 20 and the hole transport layer 40.

[0133] It is understood that when the optoelectronic device 100 further includes a light-emitting layer 50, the optoelectronic device 100 can be a light-emitting device, such as a quantum dot light-emitting device or an organic light-emitting device.

[0134] In some embodiments, the optoelectronic device 100 further includes a hole injection layer 60 disposed between the anode 10 and the hole transport layer 40.

[0135] The anode 10 and the cathode 30 are anodes and cathodes known in the art for use in optoelectronic devices. For example, they can be independently, but are not limited to, doped metal oxide electrodes, composite electrodes, graphene electrodes, carbon nanotube electrodes, elemental metal electrodes, or alloy electrodes. The material of the doped metal oxide electrode can be, but is not limited to, one or more of indium-doped tin oxide (ITO), fluorine-doped tin oxide (FTO), antimony-doped tin oxide (ATO), aluminum-doped zinc oxide (AZO), gallium-doped zinc oxide (GZO), indium-doped zinc oxide (IZO), magnesium-doped zinc oxide (MZO), aluminum-doped magnesium oxide (AMO), and cadmium-doped zinc oxide. The composite electrode is an electrode formed by stacking two or more layers of conductive materials, such as AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, TiO2 / Ag / TiO2, TiO2 / Al / TiO2, ZnS / Ag / ZnS, ZnS / Al / ZnS, Ca / Al, LiF / Ca, LiF / Al, BaF2 / Al, CsF / Al, CaCO3 / Al, BaF2 / Ca / Al, etc., where " / " indicates a stacked structure. For example, AZO / Ag / AZO represents a composite electrode comprising sequentially stacked AZO, Ag, and AZO layers. The material of the elemental metal electrode may include, but is not limited to, one or more of Ag, Ni, Pt, Au, Ir, Cu, Mo, Al, Ca, Mg, and Ba. The alloy electrodes include, but are not limited to, one or more of Au:Mg alloy electrodes and Ag:Mg alloy electrodes.

[0136] In some embodiments, the anode is an electrode with a relatively high work function, such as, but not limited to, a doped metal oxide electrode with a relatively high work function, a metal element electrode with a relatively high work function, and a carbon nanotube electrode. The metal element electrode with the high work function can be selected from, but is not limited to, Ni, Pt, Au, Ag, Ir, etc.

[0137] In some embodiments, the cathode is an electrode with a relatively low work function, such as, but not limited to, a metallic elemental electrode, a composite electrode, and an alloy electrode with a relatively low work function. The metallic elemental electrode with a relatively low work function can be Ca, Ba, Al, Mg, etc. The composite electrode with a relatively low work function can be Ca / Al, LiF / Ca, LiF / Al, BaF2 / Al, CsF / Al, CaCO3 / Al, BaF2 / Ca / Al, etc. The alloy electrode with a relatively low work function can be Au:Mg and Ag:Mg, etc.

[0138] The hole transport layer 40 is made of materials known in the art for hole transport layers, such as, but not limited to, 4,4'-N,N'-dicarbazolyl-biphenyl (CBP), poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTAA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (α-NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), poly(N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)biphenylamine) (Poly-TPD), N,N'-bis(3- 4,4'-bis(phenyl)-spiro(spiro-TPD), N,N'-bis(4-(N,N'-diphenyl-amino)phenyl)-N,N'-diphenylbenzidine (DNTPD), 4,4',4'-tris(N-carbazolyl)-triphenylamine (TCTA), 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), poly[(9,9'-dioctylfluorene-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))](TFB), poly(N-vinylcarbazole) (PVK) and its derivatives, N,N'-bis(1-naphthyl)-N,N'-diphenyl-1 1'-Biphenyl-4-4'-diamine (NPB), spiroNPB, poly(phenylenevinylene) (PPV), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene] (MEH-PPV), poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene] (MOMO-PPV), 2,2',7,7'-tetratetra[N,N-di(4-methoxyphenyl)amino]-9,9'-spirodifluorene (spiro-omeTAD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), 1,3-bis(carbazole-9-yl)benzene (MCP) The following are included: polyaniline, polypyrrole, poly(p-)phenylenevinylene, aromatic tertiary amine, polynuclear aromatic tertiary amine, 4,4'-bis(p-carbazolyl)-1,1'-biphenyl compounds, N,N,N',N'-tetraarylbenzidine, PEDOT:PSS and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, poly(spirofluorene) and its derivatives, doped graphene, undoped graphene, C60, doped or undoped NiO, doped or undoped MoO3, doped or undoped WO3, doped or undoped V2O5, doped or undoped p-type gallium nitride, doped or undoped CrO3, and doped or undoped CuO.

[0139] The material of the light-emitting layer 50 can be an organic light-emitting material or a quantum dot light-emitting material.

[0140] The organic light-emitting materials may include, but are not limited to, one or more of the following: CBP:Ir(mppy)3(4,4'-bis(N-carbazole)-1,1'-biphenyl:tris[2-(p-tolyl)pyridinium(III)), TCTX:Ir(mmpy)(4,4',4”-tris(carbazole-9-yl)triphenylamine:tris[2-(p-tolyl)pyridinium), diaromatic anthracene 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, TADF (thermally activated delayed) materials, polymers containing BN covalent bonds, HLCT (hybrid local charge transfer excited state) materials, Exciplex (excitoplex) light-emitting materials, polyacetylene and its derivatives, poly(p-phenylene) and its derivatives, polythiophene and its derivatives, and polyfluorene and its derivatives.

[0141] The quantum dot luminescent material may include, but is not limited to, one or more of the following: single-structure quantum dots, core-shell structure quantum dots, and perovskite semiconductor materials.

[0142] The materials for the single-structure quantum dots, the core materials for the core-shell structure quantum dots, and the shell materials for the core-shell structure quantum dots may include, but are not limited to, one or more of group II-VI compounds, group IV-VI compounds, group III-V compounds, and group I-III-VI compounds. The group II-VI compounds may include, but are not limited to, one or more 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 may 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 group III-V compounds may 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 group I-III-VI compounds may include, but are not limited to, one or more of CuInS2, CuInSe2, and AgInS2.

[0143] As an example, the core-shell structured quantum dots may include, but are not limited to, one or more of CdSe / CdSeS / CdS, InP / ZnSeS / ZnS, CdZnSe / ZnSe / ZnS, CdSeS / ZnSeS / ZnS, CdSe / ZnS, CdSe / ZnSe / ZnS, ZnSe / ZnS, ZnSeTe / ZnS, CdSe / CdZnSeS / ZnS, and InP / ZnSe / ZnS.

[0144] It is understood that the shell of the quantum dot with the core-shell structure can be one or more layers.

[0145] The perovskite semiconductor material may include, but is 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 Cs. + Ions, where M is a divalent metal cation, including Pb 2+ Sn 2+ Cu 2+ Ni 2+ Cd 2+ Cr 2+ Mn 2+ Co 2+ Fe 2+ 、Ge 2+ Yb 2+ Eu 2+ One or more of them, where X is a halide anion, including Cl. - ,Br - I - One or more of the following. The general structural formula of the organic-inorganic hybrid perovskite semiconductor is BMX3, where B is an organic amine cation, including CH3(CH2). n-2 NH3 + Or [NH3(CH2)] n NH3] 2+ Where n≥2, M is a divalent metal cation, including Pb 2+ Sn 2+ Cu 2+ Ni 2+ Cd 2+ Cr 2+ Mn 2+ Co 2+ Fe 2+ 、Ge 2+ Yb 2+ Eu 2+ One or more of them, where X is a halide anion, including Cl. - ,Br - I- One or more of them.

[0146] The material of the hole injection layer 60 can also be a material known in the art for hole injection layers, such as, but not limited to, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HAT-CN), PEDOT, PEDOT:PSS, PEDOT:PSS derivatives doped with s-MoO3 (PEDOT:PSS:s-MoO3), 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), tetracyanoquinone dimethyl ether (F4-TCQN), copper phthalocyanine, nickel oxide, molybdenum oxide, tungsten oxide, vanadium oxide, molybdenum sulfide, tungsten sulfide, and copper oxide.

[0147] In some embodiments, the thickness of the anode 10 ranges from 20 to 50 nm.

[0148] In some embodiments, the thickness of the electron transport layer 20 ranges from 30 to 50 nm.

[0149] In some embodiments, the thickness of the cathode 30 ranges from 20 to 50 nm.

[0150] In some embodiments, the thickness of the hole transport layer 40 ranges from 20 to 50 nm.

[0151] In some embodiments, the thickness of the light-emitting layer 50 ranges from 20 to 30 nm.

[0152] In some embodiments, the thickness of the hole injection layer 60 ranges from 20 to 50 nm.

[0153] It is understood that the optoelectronic device 100 may also be provided with some functional layers that are conventionally used in optoelectronic devices and help to improve the performance of optoelectronic devices, such as electron blocking layer, hole blocking layer, electron injection layer, etc.

[0154] It is understood that the materials of each layer of the optoelectronic device 100 can be adjusted according to the light emission requirements of the optoelectronic device 100.

[0155] In some embodiments, the optoelectronic device 100 further includes a substrate disposed on the side of the anode 10 away from the light-emitting layer 50, or the substrate disposed on the side of the cathode 30 away from the light-emitting layer 50.

[0156] The substrate can be a rigid substrate or a flexible substrate. In some embodiments, the substrate material may include, but is not limited to, one or more of glass, silicon wafer, polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate, polyamide, and polyethersulfone.

[0157] It is understood that the optoelectronic device 100 can be an upright optoelectronic device or an inverted optoelectronic device. The optoelectronic device 100 can be a quantum dot optoelectronic device or an organic optoelectronic device.

[0158] Sixthly, this application also relates to a display device, which includes the optoelectronic device 100.

[0159] The display device can be any electronic product with display function, including but not limited to smartphones, tablets, laptops, digital cameras, digital camcorders, smart wearable devices, smart weighing scales, in-vehicle displays, televisions, or e-book readers. Among them, smart wearable devices can be, for example, smart bracelets, smartwatches, virtual reality (VR) headsets, etc.

[0160] The present application will be specifically described below through specific embodiments. These embodiments are only some embodiments of the present application and are not intended to limit the present application. Unless otherwise specified, the raw materials used in the following embodiments are all commercially available products.

[0161] Example 1

[0162] The synthetic route of organic compound M1 in this embodiment is as follows:

[0163]

[0164] Step S11: Compound 1 (4 mmol, 1364 mg) (CAS No.: 832734-16-4) was added to a 100 mL two-necked flask, along with 3-mercaptophenylboronic acid (CAS No.: 352526-00-2) (10 mmol, 1540 mg), tetrakis(triphenylphosphine)palladium (0.1 mmol, 105 mg), and 40 mL of toluene. Nitrogen gas was introduced and a vacuum pump was used to evacuate the mixture for 15 minutes. The mixture was stirred and heated to 110 °C for 24 h. The reaction was then stopped and cooled to room temperature. The reaction solution was extracted by repeatedly extracting with 200 mL of water and 1500 mL of dichloromethane 3 to 4 times. The resulting organic extract was dried with anhydrous magnesium sulfate, and the filtrate was collected and purified by column chromatography using 200 to 300 mesh silica gel. The mobile phase was petroleum ether:ethyl acetate (volume ratio 20:1). Compound 2 was finally obtained as a white solid product with a yield of 74%.

[0165] Step S12: Add compound 2 (1 mmol, 399 mg) to a 50 ml single-necked flask, add palladium dichloride (0.1 mmol, 105 mg), add 40 ml of dimethyl sulfoxide, purge with nitrogen and evacuate using a vacuum pump for 15 minutes, stir and heat to 140 °C, continue the reaction for 12 h, stop the reaction and cool to room temperature, extract the reaction solution by repeatedly extracting with 200 ml of water and 1500 ml of dichloromethane 3 to 4 times, dry the obtained organic extract with anhydrous magnesium sulfate, mix the crude product with 200 to 300 mesh silica gel and perform column chromatography separation, the mobile phase is petroleum ether: ethyl acetate (volume ratio of 20:1), finally give compound 3, white solid, yield 95%;

[0166] Step S13: Add compound 3 (1 mmol, 395 mg) to a 50 mL single-necked flask, add KOH (3 mmol, 168 mg), add 1-bromohexane (2 mmol, 330 mg) (CAS No.: 111-25-1), dissolve in 10 mL DMSO, stir at 60 °C for 3 h, and stop the reaction when the starting material has completely reacted. Distill the reaction solution under reduced pressure to remove the solvent. Mix the crude product with 200 to 300 mesh silica gel and perform column chromatography separation. The mobile phase is petroleum ether: ethyl acetate (volume ratio of 20:1) to obtain the intermediate product. The intermediate product was dissolved in 30 ml of dichloromethane. Then, at 0 °C, NBS (N-bromosuccinimide) (3 mmol, 540 mg) dissolved in 20 ml of dichloromethane was added dropwise. The reaction was stopped when the starting material had completely reacted. The reaction solution was distilled under reduced pressure to remove the solvent. The crude product was mixed with 200 to 300 mesh silica gel and separated by column chromatography. The mobile phase was petroleum ether:ethyl acetate (volume ratio 20:1) to give compound 4 in 80% yield.

[0167] Step S14: Add compound 4 (1 mmol, 635 mg) to a 100 mL double-necked flask, and weigh in diphenylamine (3 mmol, 506 mg) (CAS No.: 122-39-4) and tetraphenylphosphine palladium (0.1 mmol, 105 mg). Add 40 mL of toluene, purge with nitrogen and evacuate using a vacuum pump for 15 minutes. Stir and heat to 110 °C, continue the reaction for 24 h, stop the reaction and cool to room temperature. Extract the reaction solution by repeatedly extracting with 200 mL of water and 1500 mL of dichloromethane 3 to 4 times. Dry the obtained organic extract with anhydrous magnesium sulfate and collect the filtrate. Purge the filtrate with 200 to 300 mesh silica gel using column chromatography. Use petroleum ether, dichloromethane and ethyl acetate (volume ratio 200:1:1) as the eluent to finally obtain organic compound M1, a pale yellow solid with a yield of 79%.

[0168] The NMR data for organic compound M1 in this embodiment are as follows:1 H NMR(500MHz,Chloroform-d)δ8.03-8.01(m,2H),7.74-7.73(m,2H),7.70(s,2H),7.54(s,2H),7.27-7.23(m,10H),7.10-7.0 8(m,8H),7.05-7.01(m,4H),4.21-4.18(m,2H),1.79-1.73(m,2H),1.47-1.41(m,2H),1.34-1.24(m,4H),0.91-0.88(m,3H).

[0169] Example 2

[0170] The organic compound M2 prepared in this embodiment is described above.

[0171] The synthesis of organic compound M2 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, diphenylamine in step S14 of Example 1 is replaced with 4-bromotriphenylamine (CAS No.: 36809-26-4). The reaction conditions and the amount of substances are not changed, and the final product is a yellow solid organic compound M2.

[0172] The NMR data for organic compound M2 in this embodiment are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.26-8.24(m,2H),8.03-7.99(m,4H),7.80(s,2H),7.41(s,2H),7.29-7.22(m,12H),7.11-7.07 (m,8H),7.06-7.00(m,8H),4.25(t,J=6.4Hz,2H),1.75-1.69(m,2H),1.49-1.43(m,2H),1.34-1.23(m,4H),0.92-0.88(m,3H).

[0173] Example 3

[0174] The organic compound M3 described above was prepared in this embodiment.

[0175] The synthesis of organic compound M3 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, 1-bromohexane in step S13 of Example 1 is replaced with 1-bromo-n-octane (CAS No.: 111-83-1), and diphenylamine in step S14 of Example 1 is replaced with 4,4'-dimethoxydiphenylamine (CAS No.: 101-70-2). The remaining reaction conditions and amounts of substances are unchanged, and finally, a yellow solid product, organic compound M3, is obtained.

[0176] The NMR data for organic compound M3 in this embodiment are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.04(d,J=8.6Hz,2H),7.70-7.68(m,4H),7.53(s,2H),7.22-7.18(m,2H),7.15-7.11(m,8H),6.80 -6.76(m,8H),4.21(t,J=6.4Hz,2H),3.78(s,12H),1.79-1.73(m,2H),1.48-1.41(m,2H),1.31-1.25(m,8H),0.91-0.86(m,3H).

[0177] Example 4

[0178] The organic compound M4 described above was prepared in this embodiment.

[0179] The synthesis of organic compound M4 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, 1-bromohexane in step S13 of Example 1 is replaced with hexoxyiodobenzene (CAS No.: 85557-94-4), and diphenylamine in step S14 of Example 1 is replaced with 2-bromophenoxathia (CAS No.: 10230-35-0). The remaining reaction conditions and amounts of substances are unchanged, and finally, a yellow solid product, organic compound M4, is obtained.

[0180] The NMR data for organic compound M4 in this embodiment are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.84-8.81(m,2H),8.04-8.01(m,2H),7.83-7.77( m,4H),7.68-7.63(m,4H),7.38-7.33(m,2H),7.29-7.26(m,2H),7.19-7.16(m,2 H),7.13-7.08(m,2H),7.06-7.02(m,2H),6.99-6.89(m,6H),4.01(t,J=6.1Hz,2 H),1.79-1.73(m,2H),1.47-1.40(m,2H),1.36-1.27(m,4H),0.93-0.88(m,3H).

[0181] Example 5

[0182] The organic compound M5 described above was prepared in this embodiment.

[0183] The synthesis of organic compound M5 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, 1-bromohexane in step S13 of Example 1 is replaced with hexoxyiodobenzene (CAS No.: 85557-94-4), and diphenylamine in step S14 of Example 1 is replaced with 10-(4-bromophenyl)-10H-phenoxazine (CAS No.: 71041-21-9). The remaining reaction conditions and amounts of substances are unchanged, and finally, the yellow solid product organic compound M5 is obtained.

[0184] The NMR data for organic compound M5 in this embodiment are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.83-8.80(m,2H),8.02-7.98(m,2H),7.78(s,2H),7.74-7.71(m,4H),7.62-7.59(m,2H),7.40(s,2H),7. 06-6.91(m,20H),6.77-6.72(m,4H),4.01(t,J=6.1Hz,2H),1.79-1.73(m,2H),1.47-1.41(m,2H),1.36-1.27(m,4H),0.92-0.88(m,3H).

[0185] Example 6

[0186] The organic compound M6 described above was prepared in this embodiment.

[0187] The synthesis of organic compound M6 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, 1-bromohexane in step S13 of Example 1 is replaced with p-decoxybromobenzene (CAS No.: 30752-20-6), and diphenylamine in step S14 of Example 1 is replaced with 9-(4-bromophenyl)-9H-carbazole (CAS No.: 57102-42-8). The remaining reaction conditions and amounts of substances are unchanged, and finally, a yellow solid product, organic compound M6, is obtained.

[0188] The NMR data for organic compound M6 in this embodiment are as follows: 1H NMR(500MHz,Chloroform-d)δ8.80-8.77(m,2H),8.15-8.13(m,4H),8.02-7.9 9(m,2H),7.88(s,2H),7.81(s,2H),7.69-7.66(m,4H),7.64-7.59(m,6H),7.5 4-7.50(m,4H),7.34-7.22(m,10H),6.97-6.94(m,2H),4.02(t,J=6.1Hz,2H), 1.79-1.73(m,2H),1.45-1.39(m,2H),1.29-1.22(m,12H),0.90-0.86(m,3H).

[0189] Example 7

[0190] The organic compound M7 described above was prepared in this embodiment.

[0191] The synthesis of organic compound M7 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, 1-bromohexane in step S13 of Example 1 is replaced with p-decoxybromobenzene (CAS No.: 30752-20-6), and diphenylamine in step S14 of Example 1 is replaced with bisN-(4-bromophenyl)-4-methoxy-N-(4-methylbenzene)aniline (CAS No.: 194416-45-0). The reaction conditions and the amount of substances are unchanged, and finally, a white solid product, organic compound M7, is obtained.

[0192] The NMR data for organic compound M7 in this embodiment are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.77-8.75(m,2H),8.02-7.99(m,2H),7.80(s,2H), 7.75(s,2H),7.64-7.61(m,2H),7.39-7.36(m,2H),7.25-7.22(m,4H),7.18-7.12 (m,12H),6.91-6.87(m,2H),6.82-6.78(m,8H),4.02(t,J=6.1Hz,2H),3.78(s,12 H),1.79-1.73(m,2H),1.45-1.38(m,2H),1.28-1.22(m,12H),0.91-0.86(m,3H).

[0193] Example 8

[0194] The organic compound M8 described above was prepared in this embodiment.

[0195] The synthesis of organic compound M8 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, 1-bromohexane in step S13 of Example 1 is replaced with 1-bromododecane (CAS No.: 143-15-7), and diphenylamine in step S14 of Example 1 is replaced with 10-(4-bromophenyl)-9,10-dihydro-9,9-dimethylacridine (CAS No.: 1342892-15-2). The reaction conditions and the amount of substances are unchanged, and finally, a white solid product, organic compound M8, is obtained.

[0196] The NMR data for organic compound M8 in this embodiment are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.30-8.27(m,2H),8.03-7.99(m,2H),7.64-7.61(m,4H),7.41(s,2H),7.24-7.15(m,16H),7.05- 6.97(m,8H),3.90(t,J=6.4Hz,2H),1.78-1.72(m,2H),1.59(s,12H),1.47-1.41(m,2H),1.31-1.22(m,16H),0.91-0.86(m,3H).

[0197] Example 9

[0198] The organic compound M9 described above was prepared in this embodiment.

[0199] The synthesis of organic compound M9 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, 1-bromohexane in step S13 of Example 1 is replaced with 1-bromododecane (CAS No.: 143-15-7), and diphenylamine in step S14 of Example 1 is replaced with 10-(4-bromophenyl)-10H-phenthiazine (CAS No.: 63524-03-8). The reaction conditions and the amount of substances are unchanged, and finally, a white solid product, organic compound M9, is obtained.

[0200] The NMR data for organic compound M9 in this embodiment are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.20-8.17(m,4H),7.64-7.59(m,6H),7.56-7.52(m,4H),7.44-7.31(m,12H),7.26- 7.21(m,4H),7.18-7.15(m,4H),3.83(t,J=6.0Hz,2H),1.80-1.75(m,2H),1.39-1.25(m,18H),0.92-0.87(m,3H).

[0201] Example 10

[0202] The organic compound M10 prepared in this embodiment is described above.

[0203] The synthesis of organic compound M10 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, 1-bromohexane in step S13 of Example 1 is replaced with bromocyclohexane (CAS No.: 108-85-0). The reaction conditions and the amount of substances are not changed, and finally, a white solid product organic compound M9 is obtained.

[0204] The NMR data for organic compound M10 in this embodiment are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.02(d,J=8.4Hz,2H),7.77(s,2H),7.74(d,J=2.0Hz,2H),7.56(s,2H),7.27-7.23(m,10H),7.11-7.07(m,8 H),7.06-7.01(m,4H),3.71-3.65(m,1H),1.91-1.83(m,2H),1.77-1.69(m,2H),1.61-1.53(m,2H),1.51-1.43(m,2H),1.42-1.35(m,2H).

[0205] Example 11

[0206] The organic compound M11 described above was prepared in this embodiment.

[0207] The synthesis of organic compound M11 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, 1-bromohexane in step S13 of Example 1 is replaced with 1-bromobenzene (CAS No.: 108-86-1). The reaction conditions and the amount of substances are not changed, and finally, a white solid product organic compound M11 is obtained.

[0208] The NMR data for organic compound M11 in this embodiment are as follows: 1 H NMR (500MHz, Chloroform-d) δ8.04-8.02(m,2H),7.78(s,2H),7.74-7.73(m,2H),7.68(s,2H),7.27-7.22(m,12H),7.13-7.01(m,15H).

[0209] Example 12

[0210] The organic compound M12 prepared in this embodiment is described above.

[0211] The synthesis of organic compound M12 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, 1-bromohexane in step S13 of Example 1 is replaced with 1-bromo-3-methoxypropane (CAS No.: 36865-41-5). The reaction conditions and the amount of substances are not changed, and finally, a white solid product, organic compound M9, is obtained.

[0212] The NMR data for the organic compound M12 in this embodiment are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.04-8.01(m,2H),7.74-7.73(m,2H),7.71(s,2H),7.54(s,2H),7.27-7.22(m,10H),7. 11-7.07(m,8H),7.06-7.01(m,4H),4.16(t,J=6.4Hz,2H),3.54(t,J=6.1Hz,2H),3.19(s,3H),2.06(p,J=6.3Hz,2H).

[0213] Example 13

[0214] The organic compound M13 described above was prepared in this embodiment.

[0215] The synthesis of organic compound M13 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, 1-bromohexane in step S13 of Example 1 is replaced with 4-bromopyridine (CAS No.: 1120-87-2). The reaction conditions and the amount of substances are not changed, and the white solid product organic compound M13 is finally obtained.

[0216] The NMR data for organic compound M13 in this embodiment are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.49-8.47(m,2H),8.05-8.02(m,2H),7.83(s,2H),7.74 -7.73(m,2H),7.69(s,2H),7.27-7.23(m,10H),7.10-7.07(m,10H),7.06-7.01(m,4H).

[0217] Example 14

[0218] The organic compound M14 described above was prepared in this embodiment.

[0219] The synthesis of organic compound M14 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, diphenylamine in step S14 of Example 1 is replaced with diphenylamine and 9-(4-bromophenyl)-9H-carbazole (CAS No.: 57102-42-8) (molar ratio 1:1). The other reaction conditions and amounts of substances remain unchanged, and the white solid product organic compound M14 is finally obtained.

[0220] The NMR data for organic compound M14 in this embodiment are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.35-8.33(m,1H),8.16-8.13(m,3H),8.04-7.99(m,2H),7 .78-7.77(m,1H),7.76-7.73(m,3H),7.70-7.65(m,2H),7.63-7.59(m,2H),7.43-7.39(m ,2H),7.35-7.30(m,4H),7.27-7.22(m,6H),7.11-7.08(m,4H),7.06-7.01(m,2H),4.21- 4.18(m,2H),1.80-1.73(m,2H),1.48-1.42(m,2H),1.35-1.23(m,4H),0.92-0.87(m,3H).

[0221] Example 15

[0222] The organic compound M15 described above was prepared in this embodiment.

[0223] The synthesis of organic compound M15 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, the diphenylamine in step S14 of Example 1 is replaced with diphenylamine and bisN-(4-bromophenyl)-4-methoxy-N-(4-methylbenzene)aniline (CAS No.: 194416-45-0) (molar ratio 1:1). The reaction conditions and the amount of substances are not changed, and the white solid product organic compound M15 is finally obtained.

[0224] The NMR data for organic compound M15 in this embodiment are as follows: 1H NMR(500MHz,Chloroform-d)δ8.36-8.34(m,1H),8.19-8.12(m,4H),7.97-7.95(m,1H),7.92-7.89(m, 1H),7.86-7.82(m,2H),7.79-7.75(m,3H),7.73-7.66(m,6H),7.63-7.59(m,3H),7.56-7.53(m,1H),7. 42-7.40(m,1H),7.35-7.30(m,3H),7.28-7.22(m,2H),7.18-7.14(m,2H),6.87-6.82(m,4H),3.92(t,J =6.4Hz,2H),3.78(s,6H),1.77-1.72(m,2H),1.47-1.41(m,2H),1.34-1.23(m,4H),0.91-0.88(m,3H).

[0225] Comparative Example 1

[0226] Preparation of organic compound P1:

[0227]

[0228] Step 1: Add compound P1-1 (4 mmol, 1356 mg) (832734-16-4) to a 100 mL two-necked flask, add 1-bromohexane (CAS No.: 1121-24-0) (5 mmol, 825 mg), add potassium hydroxide (10 mmol, 560 mg), dissolve in 30 mL of dimethyl sulfoxide solvent, heat to 100 °C, react for 6 h, stop the reaction when the starting material has completely reacted by thin-layer chromatography (TLC), extract the reaction solution, wash repeatedly 3 to 4 times with dichloromethane (100 mL) and water (25 mL), and dry the organic phase with anhydrous magnesium sulfate. Mix the crude product with 200 to 300 mesh silica gel and perform column chromatography separation. The mobile phase is petroleum ether: ethyl acetate (volume ratio 15:1). Finally, compound P1-2 is obtained as a white solid product with a yield of 63%.

[0229] Step 2: Add compound P1-2 (1 mmol, 423 mg) to a 100 ml two-necked flask, and weigh in diphenylamine (3 mmol, 507 mg) (CAS No.: 122-39-4) and tetraphenylphosphine palladium (0.1 mmol, 105 mg). Add 40 ml of toluene, purge with nitrogen and evacuate using a vacuum pump for 15 minutes. Stir and heat to 110 °C, continue the reaction for 24 h, stop the reaction and cool to room temperature. Extract the reaction solution by repeatedly extracting with 200 ml of water and 1500 ml of dichloromethane 3 to 4 times. Dry the obtained organic extract with anhydrous magnesium sulfate and collect the filtrate. Pour the filtrate into 200 to 300 mesh silica gel and purify and separate by column chromatography. Use petroleum ether, dichloromethane and ethyl acetate (volume ratio 200:1:1) as the eluent. Finally, organic compound P1 is obtained as a pale yellow solid with a yield of 72%.

[0230] The NMR data of organic compound P1 in this comparative example are as follows: 1 H NMR(500MHz,Chloroform-d)δ7.26-7.22(m,8H),7.11-7.08(m,8H),7.06-7.01(m,4H),6.97-6.95(m,2H),6.82-6.80(m,2 H),6.65-6.62(m,2H),4.15(t,J=6.4Hz,2H),1.74-1.68(m,2H),1.45-1.38(m,2H),1.34-1.25(m,4H),0.91-0.87(m,3H).

[0231] Comparative Example 2

[0232] The chemical structural formula of the organic compound P2 in this comparative example is:

[0233]

[0234] The synthesis of organic compound P2 in this embodiment is similar to that of organic compound P1 in Comparative Example 1. The difference is that in step 2 of Comparative Example 1, the diphenylamine in step 2 is replaced with 2-bromophenoxathia (CAS No.: 10230-35-0). The other reaction conditions and amounts of substances remain unchanged, and the final product is a yellow solid organic compound P2.

[0235] The NMR data for the organic compound P2 in this comparative example are as follows: 1H NMR(500MHz,Chloroform-d)δ7.66-7.65(m,2H),7.41-7.38(m,2H),7.30-7.28(m,2H),7.26-7.21(m,4H),7.10- 6.98(m,10H),4.18(t,J=6.4Hz,2H),1.75-1.69(m,2H),1.46-1.40(m,2H),1.33-1.24(m,4H),0.91-0.88(m,3H).

[0236] Comparative Example 3

[0237] The chemical structural formula of organic compound P3 in this comparative example is:

[0238]

[0239] The synthesis of organic compound P3 in this embodiment is similar to that of organic compound P1 in Comparative Example 1. The difference is that in step 1 of Comparative Example 1, 1-bromohexane is replaced with 4-bromobenzoic acid (CAS No.: 586-76-5), and in step 2, diphenylamine is replaced with 2-thiopheneboronic acid (CAS No.: 6165-68-0). The remaining reaction conditions and amounts of substances are unchanged, and the final product is a yellow solid organic compound P3.

[0240] The NMR data for the organic compound P3 in this comparative example are as follows: 1 H NMR (500MHz, Chloroform-d) δ8.01-7.98(m,2H),7.68-7.62(m,6H),7.23-7.15(m,6H),7.12-7.09(m,2H).

[0241] Comparative Example 4

[0242]

[0243] The synthesis of organic compound P4 in this embodiment is similar to that of organic compound P1 in Comparative Example 1. The difference is that in step 1 of Comparative Example 1, 1-bromohexane is replaced with 4'-bromo[1,1'-biphenyl]-4-carboxylic acid (CAS No.: 5731-11-3), and in step 2, diphenylamine is replaced with 2-thiopheneboronic acid (CAS No.: 6165-68-0). The remaining reaction conditions and amounts of substances are unchanged, and the final product is a yellow solid organic compound P4.

[0244] The NMR data for organic compound P4 in this comparative example are as follows: 1H NMR (500MHz, Chloroform-d) δ8.12-8.09(m,2H),7.67-7.62(m,6H),7.54-7.50(m,4H),7.26-7.23(m,2H),7.19-7.15(m,4H),7.13-7.10(m,2H).

[0245] Comparative Example 5

[0246]

[0247] Step 1: Add compound P5-1 (4 mmol, 1048 mg) (CAS No.: 832734-15-3) to a 100 mL two-necked flask, add 3-mercaptophenylboronic acid (CAS No.: 352526-00-2) (5 mmol, 770 mg), add tetrakis(triphenylphosphine)palladium (0.1 mmol, 105 mg), add 40 mL of toluene, purge with nitrogen and evacuate using a vacuum pump for 15 minutes, stir and heat to 110 °C, continue the reaction for 24 h, stop the reaction and cool to room temperature, extract the reaction solution, repeatedly extract with 200 mL of water and 1500 mL of dichloromethane 3 to 4 times, dry the obtained organic extract with anhydrous magnesium sulfate, collect the filtrate and mix it with 200 to 300 mesh silica gel for column chromatography purification and separation, the mobile phase is petroleum ether:ethyl acetate (volume ratio 20:1), finally give compound 2, a white solid, with a yield of 80%;

[0248] Step 2: Add compound P5-2 (1 mmol, 291 mg) and palladium dichloride (0.1 mmol, 105 mg) to a 50 ml single-necked flask, add 40 ml of dimethyl sulfoxide, purge with nitrogen and evacuate using a vacuum pump for 15 minutes, stir and heat to 140 °C, continue the reaction for 12 h, stop the reaction and cool to room temperature, extract the reaction solution by repeatedly extracting with 200 ml of water and 1500 ml of dichloromethane 3 to 4 times, dry the obtained organic extract with anhydrous magnesium sulfate, and perform column chromatography separation with 200 to 300 mesh silica gel mixed with the crude product. The mobile phase is petroleum ether: ethyl acetate (volume ratio 20:1), and finally obtain compound P5-3 as a white solid with a yield of 93%.

[0249] Step 3: Add compound P5-3 (1 mmol, 289 mg) to a 50 mL single-necked flask, add KOH (3 mmol, 168 mg), add 1-bromo-3,5-diphenylbenzene (1.5 mmol, 464 mg) (CAS No.: 103068-20-8), dissolve in 10 mL DMSO, stir at 60 °C for 3 h, and stop the reaction when the starting material has completely reacted. Distill the reaction solution under reduced pressure to remove the solvent. Mix the crude product with 200-300 mesh silica gel and perform column chromatography separation. The mobile phase is petroleum ether:ethyl acetate (volume ratio 20:1) to obtain organic compound P5 with a yield of 92%.

[0250] The NMR data for organic compound P5 in this comparative example are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.36-8.33(m,1H),7.88-7.86(m,1H),7.83(s,1H),7.61-7.52(m,7H) ),7.47-7.41(m,6H),7.37-7.33(m,2H),7.30-7.25(m,1H),7.24-7.20(m,1H),7.06-6.94(m,3H).

[0251] Device Example 1

[0252] This embodiment of the device provides an optoelectronic device and its fabrication method, which specifically includes the following steps.

[0253] Step 1: Place the ITO glass slide in a glass dish containing an ethanol solution, and sonicate it with acetone, deionized water, and ethanol for 20 minutes each in sequence, then dry it with a nitrogen gun; then place the cleaned ITO glass slide in an oxygen plasma for 10 minutes; and then treat the surface of the ITO substrate with ultraviolet-ozone for 15 minutes.

[0254] Step 2: Spin-coat PEDOT:PSS onto the cleaned ITO glass slides in air at a speed of 5000 r / min for 30 seconds; after spin-coating, anneal in air at a temperature of 150℃ for 30 minutes to obtain a hole injection layer with a thickness of 40 nm.

[0255] Step 3: Spin-coat the hole injection layer with TFB material at a concentration of 8 mg / mL at a speed of 3000 r / min for 30 seconds; after spin-coating, anneal in a glove box at a temperature of 120℃ for 10 minutes to obtain a hole transport layer with a thickness of 30 nm.

[0256] Step 4: Spin-coat a 20 mg / mL quantum dot green QD (CdZnSe / ZnS) dispersion onto the hole transport layer at a spin speed of 2000 r / min for 30 seconds; then... -2 After standing for 15 minutes under MPa, a light-emitting layer with a thickness of 30nm was obtained;

[0257] Step 5: Dissolve organic compound M1 from Example 1 in toluene to obtain a solution of organic compound M1 with a concentration of 30 mg / mL. Spin-coat the solution onto the luminescent layer at a spin speed of 3000 r / min for 30 seconds, followed by [further details needed - likely related to a specific process]. -2 After standing for 15 minutes under MPa, an electron transport layer with a thickness of 40 nm was obtained.

[0258] Step 6: Through thermal evaporation, the vacuum level is not higher than 3 x 10. -4 Pa, Ag is vapor-deposited at a rate of 1 angstrom / second for 200 seconds to form a top silver electrode with a thickness of 20 nm on the electron transport layer, and then encapsulated with epoxy resin to obtain an optoelectronic device.

[0259] The device structure in this embodiment is: ITO / PEDOT:PPS / TFB / QD / M1 / Ag.

[0260] Device Examples 2-15

[0261] The devices in Examples 2 to 15 are basically the same as those in Example 1, except that in step 5, organic compounds M2 to M15 from Examples 2 to 15 are used respectively.

[0262] Device Comparison Examples 1-5

[0263] The devices in Comparative Examples 1 to 5 are basically the same as those in Device Example 1, except that in step 5, organic compounds P1 to P5 of Comparative Examples 1 to 5 are used respectively.

[0264] Electron mobility testing of organic compounds

[0265] Test devices with the structure ITO / F (40 nm) / Ag (20 nm) were prepared using the organic compounds of Examples 1-15 and Comparative Examples 1-5 as electron transport materials, respectively. Here, F refers to the organic compounds of Examples 1-15 and Comparative Examples 1-5. The electron mobility of the prepared test devices was then measured using the space charge-confined current method (SCLC), and the results are shown in Table 1.

[0266] The space charge confined current (SCLC) method can be described by the Mott-Gurney equation:

[0267] J=9με0εr V 2 / (8d 3 )

[0268] Where J is the current density, μ is the electron mobility, and ε0 is the vacuum permittivity (8.85 × 10⁻⁶). -12 F / m), ε r is the dielectric constant of the material (usually approximated as 3 for organic semiconductors), V is the applied bias voltage, and d is the film thickness.

[0269] Device performance testing:

[0270] The maximum brightness L of the optoelectronic devices in Device Examples 1-15 and Device Comparative Examples 1-5 were tested respectively. max Tests included lifetime T95 test, lifetime T95@1000nit test, current efficiency CE test, and light stability test. The test results are shown in Table 1.

[0271] Among them, the maximum brightness L max The test method for current efficiency CE is as follows: using the FPD optical property measurement equipment, the efficiency test system is built by controlling the QE PRO spectrometer, Keithley 2400, and Keithley 6485 through LabVIEW, and the parameters such as voltage, current, brightness, and emission spectrum are measured, and the current efficiency CE is calculated.

[0272] The test methods for lifetime T95 and lifetime T95@1000nit are as follows: Under constant current or voltage drive, the time required for the brightness of the device to decrease to a certain percentage of its maximum brightness is defined as T95. This lifetime is the measured lifetime. To shorten the testing cycle, device lifetime testing is usually performed at high brightness by accelerating device aging, and the lifetime at high brightness is obtained by fitting the extended exponential decay brightness decay fitting formula. For example, the lifetime at 1000nit is measured as T95@1000nit. The specific calculation formula is as follows:

[0273]

[0274] Among them, T95 L For longer lifespan at low brightness, T95 H For the measured lifetime under high brightness, L H To accelerate the device to its maximum brightness, L L The value is 1000 nits, and A is the acceleration factor. In this experiment, the lifetime of several groups of green QLED devices under rated brightness was measured, and the value of A was found to be 1.7.

[0275] Table 1:

[0276]

[0277]

[0278] As shown in Table 1:

[0279] Compared with the organic compounds in Comparative Examples 1 to 5, the organic compounds in Examples 1 to 15 have higher electron mobility, indicating that the organic compounds of this application have better electron transport performance.

[0280] Compared to the optoelectronic devices in Device Comparison Examples 1 to 5, the optoelectronic devices in Device Examples 1 to 15 have higher maximum brightness, longer lifespan, and higher current efficiency. It can be seen that the organic compound of this application, as an electron transport layer material, can effectively improve the maximum brightness, lifespan, and current efficiency of optoelectronic devices.

[0281] The technical solutions provided by the embodiments of this application have been described in detail above. Specific examples have been used to illustrate the principles and implementation methods of this application. The description of the above embodiments is only for the purpose of helping to understand the method and core ideas of this application. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of this application. Therefore, the content of this specification should not be construed as a limitation of this application.

Claims

1. An organic compound, characterized in that, It has the structure shown in equation (I): Where n' and n” are each an independent integer from 1 to 4; R1 is selected from H, D, and substituted or unsubstituted C1-C1. 30 Alkyl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C1-C 30 alkoxy, substituted or unsubstituted C1-C 30 One or more combinations of alkylthio, aryl with 6 to 60 substituted or unsubstituted ring atoms, aryloxy with 6 to 60 substituted or unsubstituted ring atoms, and heteroaryl with 5 to 60 substituted or unsubstituted ring atoms; Ar1 and Ar2 are each independently selected from one or more combinations of aryl groups with 6 to 60 cyclic atoms and heteroaryl groups with 5 to 60 cyclic atoms, whether substituted or unsubstituted. Each of the substituents mentioned herein is independently selected from D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C1 groups, each time it appears. 20 Alkyl, C1-C 20 The heteroaryl group is selected from one or more of alkoxy groups and aryl groups having a ring number of 6 to 20; the heteroatom of the heteroaryl group is selected from one or more of O, N, S, P, and Si.

2. The organic compound according to claim 1, characterized in that, R1 is selected from H, D, and substituted or unsubstituted C1 to C2. 20 Alkyl groups, substituted or unsubstituted C3-C6 chains 20 cycloalkyl, substituted or unsubstituted C1-C 20 alkoxy, substituted or unsubstituted C1-C 20 One or more combinations of alkylthio, aryl with 6 to 30 substituted or unsubstituted ring atoms, aryloxy with 6 to 30 substituted or unsubstituted ring atoms, and heteroaryl with 5 to 30 substituted or unsubstituted ring atoms; And / or, Ar1 and Ar2 are each independently selected from one of the following structures: Where n1 and n2 are each independently selected from integers from 0 to 5, and n3, n4, n5, and n6 are each independently selected from integers from 0 to 4; M is selected from SiR8, SiR8R9, N, and NR. 10 NR 16 , O or S; X is selected from SiR 11 SiR 11 R 12 CR 13 R 14 S, O, N or NR 15 ; Among them, R2 to R7 are each independently selected from substituted or unsubstituted C1 to C7. 30 Alkyl, substituted or unsubstituted C1-C 30 The aryl group is selected from one or more combinations of alkoxy, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, and substituted or unsubstituted aryl groups having 6 to 20 ring atoms. When substituted, each substituent is independently selected from D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1 to C2. 20 Alkyl, C1-C 20 A combination of one or more of alkoxy groups and aryl groups having 6 to 20 ring atoms; R8 to R 15 Each is independently selected from H, D, substituted or unsubstituted C1 to C2. 30 The alkyl group, or a combination of one or more aryl groups having 6 to 60 substituted or unsubstituted ring atoms, wherein each substituted group is independently selected from D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1 to C2. 20 Alkyl, C1-C 20 A combination of one or more of alkoxy groups and aryl groups having 6 to 20 ring atoms; R 16 Selected from substituted or unsubstituted C1 to C2 30 The alkylene group, or a combination of one or more arylene groups having 6 to 60 substituted or unsubstituted ring atoms, wherein each substituent is independently selected from D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1 to C2. 20 Alkyl, C1-C 20 One or more combinations of alkoxy groups and aryl groups having 6 to 20 ring atoms.

3. The organic compound according to claim 2, characterized in that, R2 to R7 are each independently selected from C1 to C7. 30 Alkyl, C1-C 30 One or more of the alkoxy groups; And / or, and / or, R8 to R 15 Each is independently selected from H, D, C1 to C 30 One or more combinations of alkyl groups and aryl groups having 6 to 60 cyclic atoms; And / or, R 16 Selected from C1 to C 30 One or more combinations of alkylene groups and arylene groups having 6 to 60 cyclic atoms.

4. The organic compound according to any one of claims 1 to 3, characterized in that, Ar1 and Ar2 are each independently selected from one of the following structures:

5. The organic compound according to claim 4, characterized in that, Ar1 and Ar2 are each independently selected from one of the following structural formulas (1) to (13): R2 to R7 are each independently selected from one or more combinations of C1-C6 alkyl, C1-C6 alkoxy, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, and aryl with 6 to 10 ring atoms; n1 and n2 are each independently selected from integers from 0 to 5, and n3, n4, n5, and n6 are each independently selected from integers from 0 to 4.

6. The organic compound according to claim 1, characterized in that, The organic compound is selected from any one of the compounds shown in formulas M1 to M15:

7. The application of the organic compound as described in any one of claims 1 to 6 in the field of optoelectronics.

8. A composition, characterized in that, Includes solvents and organic compounds as described in any one of claims 1 to 6.

9. The composition according to claim 8, characterized in that, The solvent is selected from one or more of benzene, toluene, xylene, chlorobenzene, bromobenzene, methylphenol, and styrene; and / or In the composition, the concentration of the organic compound is 10–40 mg / mL.

10. An optoelectronic device, characterized in that, Includes the organic compounds described in any one of claims 1 to 6.

11. The optoelectronic device as described in claim 10, characterized in that, The optoelectronic device includes an anode, an electron transport layer, and a cathode stacked sequentially, wherein the material of the electron transport layer includes the organic compound described in any one of claims 1 to 6.

12. The optoelectronic device as described in claim 11, characterized in that, The optoelectronic device further includes a hole transport layer disposed between the electron transport layer and the anode; and / or The optoelectronic device further includes a light-emitting layer disposed between the electron transport layer and the anode; and / or The optoelectronic device further includes a hole injection layer disposed between the anode and the electron transport layer.

Images