Organic materials, compositions, thin films, and optoelectronic devices

Abstract

This application discloses an organic compound, a composition, a thin film, and an optoelectronic device, relating to the field of display technology. The organic compound includes: Ar1-Ar2-Ar3; wherein, the structural formula of Ar1 is shown below; the structural formula of Ar2 is shown below; and the structural formula of Ar3 is selected from one of the following formulas. The organic compound provided in this application has good luminescent properties.

Description

Technical Field

[0001] This application relates to the field of display technology, and more particularly to an organic material, composition, thin film, and optoelectronic device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) use organic materials as the light-emitting layer. However, organic materials have poor light-emitting performance, which affects the luminous efficiency of OLEDs. Summary of the Invention

[0003] In view of this, this application provides an organic material, a composition, a thin film, and an optoelectronic device.

[0004] This application embodiment is implemented as follows: an organic compound, the organic compound comprising: Ar1-Ar2-Ar3; wherein,

[0005] The structural formula of Ar1 is shown below:

[0006] The structural formula of Ar2 is shown below:

[0007] The structural formula for Ar3 is selected from one of the following:

[0008] Where n1 is selected from integers from 0 to 5; n2 is selected from integers from 0 to 5; n3 is selected from integers from 0 to 5; n4 is selected from integers from 0 to 1; 0≤n1+n2+n3+n4≤15;

[0009] n5 is selected from integers from 0 to 10;

[0010] n6 is selected from integers from 0 to 7; n7 is selected from integers from 0 to 5; n8 is selected from integers from 0 to 5; 0 ≤ n6 + n7 + n8 ≤ 16;

[0011] n9 is selected from integers from 0 to 7; n10 is selected from integers from 0 to 5; n11 is selected from integers from 0 to 5; 0 ≤ n9 + n10 + n11 ≤ 16;

[0012] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 Each occurrence is independently selected from D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C2. 30 Alkyl, C1-C 30 One or more of alkoxy groups and aryl groups having 6 to 30 ring atoms.

[0013] Accordingly, embodiments of this application also provide a composition comprising a solvent and the aforementioned organic compounds.

[0014] Accordingly, embodiments of this application also provide a thin film, the material of which includes the aforementioned organic compounds.

[0015] Accordingly, this application also provides an optoelectronic device, including an anode, a light-emitting layer and a cathode stacked sequentially, wherein the material of the light-emitting layer includes the above-mentioned organic matter, or the light-emitting layer includes the above-mentioned thin film.

[0016] The organic compound provided in this application has good luminescent properties. Attached Figure Description

[0017] 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.

[0018] Figure 1 This is a flowchart of the method for preparing organic compounds provided in the embodiments of this application;

[0019] Figure 2 This is a schematic diagram of the structure of the optoelectronic device provided in the embodiments of this application;

[0020] Figure 3 This is a schematic diagram of the structure of another optoelectronic device provided in the embodiments of this application;

[0021] Figure 4 These are the ultraviolet absorption spectra of the organic compounds in toluene solution provided in Examples 1-4 of this application;

[0022] Figure 5 These are the steady-state fluorescence spectra of the organic compounds provided in Examples 1-4 of this application;

[0023] Figure 6 These are the thermogravimetric diagrams of the organic compounds provided in Examples 1-4 of this application;

[0024] Figure 7 These are the electroluminescence spectra of the optoelectronic devices provided in Device Embodiments 5 to 8 of this application.

[0025] Figure label:

[0026] Optoelectronic device 100; anode 10; light-emitting layer 20; cathode 30; hole functional layer 40; electron functional layer 50. Detailed Implementation

[0027] 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.

[0028] 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 orientation shown 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.

[0029] 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.

[0030] In this application, "at least one" means one or more, and "more than one" means two or more. "One or more", "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.

[0031] 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.

[0032] In this application, "substituted or unsubstituted" means that the defined group may or may not be substituted. It is understood that when the group is substituted by a substituent, the number of substituents may be one, two, three or more, and when the number of substituents is two or more, the substituents may be the same or different.

[0033] In this application, "ring atom number" refers to the number of ring atoms constituting the ring itself in a cyclic compound (e.g., a monocyclic or polycyclic compound) obtained by atomic bonding, i.e., the number of atoms forming the ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atom count. The same applies to the "ring atom number" described below unless otherwise specified. For example, the benzene ring has 6 ring atoms, the naphthalene ring has 10 ring atoms, and the thiophene group has 5 ring atoms.

[0034] 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.

[0035] 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 30, 1 to 25, 1 to 20, 1 to 15, 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 ...

[0036] 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), tert-butoxy (-OC(CH3)3 or -OtBu), and n-hexyloxy (-O-C6H). 13 ), n-Decaalkoxy (-OC) 10 H 21 ), n-dodecyloxy (-OC) 12 H 25 ).

[0037] In this application, amino represents -NR 1 R 2 , where R 1 R 2 Each can independently represent H or alkyl, that is, amino can refer to -NH2, -NH (alkyl), or -N alkyl (alkyl).

[0038] In this application, the asterisk (*) associated with a single bond indicates a linking site or fusion site. When no linking site is specified in the group, it indicates that any selectable linking site in the group is chosen as the linking site. For example, In this structure, any linkable site on the three benzene rings and any linkable site on the pyrimidine ring can serve as a linking site for the 1,2-benzophenanthrene group in the main skeleton structure.

[0039] In this application, the single bond connecting the substituent to the through group indicates that the substituent can be attached to any position on the ring. For example R1 penetrates the benzene ring, and R1 can be attached to any substituted site in the benzene ring it penetrates. For example... R5 penetrates all benzene rings in the 1,2-benzophenanthrene group, and R5 can be attached to any substituted site in any benzene ring it penetrates. Furthermore, in this application, when the same substituent appears multiple times, it can be independently selected from different groups; if the above general formula can contain n1 R1s, then each R1 can be independently selected from different groups. Additionally, The X1 connected to a single bond indicates that X1 can be attached to any substituted site in the group.

[0040] In this application, "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.

[0041] The mechanism of OLED devices can be summarized as follows: electrons and holes are injected from the cathode and anode, respectively. Charge carriers migrate through the transport layer under voltage-driven conditions and ultimately recombine in the emissive layer to emit light. Therefore, the material of the emissive layer plays a crucial role in OLEDs. Unlike photoexcitation, which generates triplet states through intersystem crossing, electroexcitation forms singlet and triplet excitons through the recombination of injected electrons and holes. According to quantum mechanical spin statistics, under electro-injection, the ratio of singlet to triplet excitons formed by electron-hole recombination is 1:3. For first-generation fluorescent materials, 75% of triplet excitons are wasted by non-radiative transitions back to the ground state, and the theoretical upper limit of the device's EQE is only 5%. Currently, the most efficient way to utilize triplet excitons is to convert them into luminescent singlet excitons. The most representative mechanisms for triplet-to-singlet conversion are threefold: triplet-triplet annihilation, thermally activated delayed fluorescence, and thermal exciton mechanisms. In recent years, the thermal exciton mechanism has been proposed in this field because it can utilize triplet excitons through antisystem crossing from high-energy triplet to singlet states, achieving near 100% utilization of electrogenerated excitons, and has attracted widespread attention. The antisystem crossing process can occur not only between T1 and S1, but also in higher triplet states (T...n (n≥2) and singlet state (S m , between m≥1).

[0042] The primary design principle for thermal exciton materials is to employ a one-dimensional fused ring structure. Based on theoretical calculations and experimental tests, the inventors discovered that one-dimensional fused rings typically have a large energy level difference between the T2 and T1 states, and a small energy level difference between the S1 and T2 states. Therefore, it is necessary to further develop building groups for antisystem crosstalk channels that are more conducive to 100% exciton utilization in thermal engine theory.

[0043] The technical solution of this application is as follows:

[0044] In a first aspect, embodiments of this application provide an organic compound, the organic compound comprising: Ar1-Ar2-Ar3;

[0045] The structural formula of Ar1 is shown below:

[0046] The structural formula of Ar2 is shown below:

[0047] The structural formula for Ar3 is selected from one of the following:

[0048] Where n1 is selected from integers from 0 to 5; n2 is selected from integers from 0 to 5; n3 is selected from integers from 0 to 5; n4 is selected from integers from 0 to 1; 0≤n1+n2+n3+n4≤15;

[0049] n5 is selected from integers from 0 to 10;

[0050] n6 is selected from integers from 0 to 7; n7 is selected from integers from 0 to 5; n8 is selected from integers from 0 to 5; 0 ≤ n6 + n7 + n8 ≤ 16;

[0051] n9 is selected from integers from 0 to 7; n10 is selected from integers from 0 to 5; n11 is selected from integers from 0 to 5; 0 ≤ n9 + n10 + n11 ≤ 16;

[0052] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 Each occurrence is independently selected from D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C2. 30 Alkyl, C1-C 30 One or more of alkoxy groups and aryl groups having 6 to 30 ring atoms.

[0053] Understandable. Indicates a substituted or unsubstituted triphenylpyrimidinyl group;

[0054] Indicates substituted or unsubstituted 1,2-benzophenanthrene (benzophenanthrene) base); This indicates whether the N,N-diphenylnaphth-1-amino group is substituted or unsubstituted; This indicates whether the N,N-diphenylnaphth-2-amino group is substituted or unsubstituted.

[0055] The organic compound provided in this application uses 1,2-benzophenanthrene-1,2-trimethylbenzylene as the building block and selects 1,2-benzophenanthrene-1,2-trimethylbenzylene as the core structure. The 1,2-benzophenanthrene-1,2-trimethylbenzylene possesses a large T1-T2 energy level difference and a small S1-T2 energy level difference, which is conducive to high-energy anti-system crossing. This allows it to open high-energy anti-system crossing channels for excitons, realizing a "thermal exciton" mechanism, improving exciton utilization, and thus enhancing the luminescence performance of the organic compound. Furthermore, the 1,2-benzophenanthrene-1,2-trimethylbenzylene has good color purity, which is beneficial for improving light emission purity. The N,N-diphenylnaphthyl-1-amino or N,N-diphenylnaphthyl-2-amino groups have high LUMO energy levels, serving as electron-donating structures, which is beneficial for improving... High carrier mobility, especially electron mobility, and promotes the balance of electron and hole transport; the triphenylpyrimidine group has a high band gap (HOMO-LUMO energy level difference), resulting in good luminescence performance. The rigid structure of the triphenylpyrimidine group helps to improve the thermal stability of the material and avoid decomposition caused by high temperature or long-term operation. The polarity of the pyrimidine ring and the electrochemical regulation of the triphenyl group help to provide good electron transport performance, balance carrier injection, reduce operating voltage, and improve the luminescence efficiency and lifetime of organic materials; the asymmetric structure of organic materials and the torsion between the donor and acceptor and the π bridge can inhibit molecular aggregation and reduce exciton quenching, which is conducive to achieving high efficiency.

[0056] This scheme modifies the structure by introducing groups containing aromatic heterocyclic structures and groups containing aromatic ring structures, thereby controlling the properties of high-energy excited states and achieving exciton utilization dominated by the thermal exciton mechanism, thus improving exciton utilization efficiency. The combination of 1,2-benzophenanthrene, N,N-diphenylnaphthyl-1-amine or N,N-diphenylnaphthyl-2-amine and triphenylpyrimidinyl can synergistically produce better beneficial effects, giving organic compounds better light controllability and meeting the requirements of high-efficiency light emission.

[0057] In addition, by fine-tuning the compound structure, such as changing the substituents R1, R2, R3, R4, R5, R6, R7, R8, R9, and R on the skeleton, 10 R 11 By considering factors such as type, quantity, and substitution sites, more compounds with good luminescence properties can be obtained, providing a freer and broader selection for screening organic materials.

[0058] In some embodiments, n1 is selected from integers from 0 to 3; n2 is selected from integers from 0 to 3; n3 is selected from integers from 0 to 3; n4 is selected from integers from 0 to 1; 0 ≤ n1 + n2 + n3 + n4 ≤ 10, and the sum of n1 + n2 + n3 + n4 can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. When n1 + n2 + n3 + n4 = 0, it indicates that Ar1 does not have R1, R2, R3, or R4 substituents, and Ar1 is triphenylpyrimidinyl.

[0059] In some embodiments, n5 is selected from integers from 0 to 6, for example, it can be 0, 1, 2, 3, 4, 5, or 6. When n5 is selected as 0, it indicates that Ar2 does not have an R5 substituent, and Ar2 is 1,2-benzophenanthrene.

[0060] In some embodiments, n6 is selected from integers from 0 to 5; n7 is selected from integers from 0 to 3; n8 is selected from integers from 0 to 3; 0 ≤ n6 + n7 + n8 ≤ 10, and the sum of n6 + n7 + n8 can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. When n6 + n7 + n8 = 0, it indicates that Ar3 does not have R6, R7, or R8 substituents, and Ar3 is N,N-diphenylnaphthalene-1-amino.

[0061] In some embodiments, n9 is selected from integers from 0 to 5; n10 is selected from integers from 0 to 3; n11 is selected from integers from 0 to 3; 0 ≤ n9 + n10 + n11 ≤ 10, and the sum of n9 + n10 + n11 can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. When n9 + n10 + n11 = 0, it indicates that Ar4 does not contain R9 or R... 10 R 11 The substituent Ar4 is N,N-diphenylnaphth-1-amino.

[0062] It is understandable that R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 They can be the same or different. In other words, when Ar1 has multiple substituents, the substituents can be the same or different. When Ar2 has multiple substituents, the substituents can be the same or different. When Ar3 has multiple substituents, the substituents can be the same or different. When Ar4 has multiple substituents, the substituents can be the same or different.

[0063] In some embodiments, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 Each occurrence is independently selected from D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C2. 20 Alkyl, C1-C 20One or more of alkoxy groups and aryl groups having 6 to 24 ring atoms.

[0064] In some embodiments, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 Each occurrence is independently selected from D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C2. 10 Alkyl, C1-C 10 One or more of alkoxy groups and aryl groups having 6 to 18 ring atoms.

[0065] In some embodiments, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 Each occurrence is independently selected from one or more of D, amino, hydroxyl, nitro, C1-C8 alkyl, C1-C8 alkoxy, and aryl groups with 6-12 ring atoms.

[0066] In some embodiments, Ar1 is selected from one of the following structural formulas:

[0067]

[0068] In some embodiments, Ar1 is selected from one of the following structural formulas:

[0069]

[0070] In some embodiments, Ar2 is selected from one of the following structural formulas:

[0071]

[0072] In some embodiments, Ar2 is selected from one of the following structural formulas:

[0073]

[0074] In some embodiments, Ar3 is selected from one of the following structural formulas:

[0075]

[0076] In some embodiments, Ar3 is selected from one of the following structural formulas:

[0077]

[0078]

[0079] In some embodiments, the organic compound is selected from one of the following structures: M1 to M30:

[0080]

[0081]

[0082] The organic compounds provided in this application have simple structures and are easy to synthesize. The triphenylpyrimidinyl group and the N,N-diphenylnaphthyl-1-amine or N,N-diphenylnaphthyl-2-amine group are located at the para position of the 1,2-benzophenanthrene group, which makes the structure of the organic compounds more stable. With the 1,2-benzophenanthrene group as the core structure, the exciton utilization rate can be effectively improved, and the carrier mobility can be enhanced through the coordination of the triphenylpyrimidinyl group and the N,N-diphenylnaphthyl-1-amine or N,N-diphenylnaphthyl-2-amine group.

[0083] In some embodiments, the emission peak wavelength of the organic compound is 440 nm to 480 nm, for example, it can be 440 nm, 445 nm, 450 nm, 460 nm, 465 nm, 470 nm, 475 nm, 480 nm, or any range between two values. It should be noted that the emission peak wavelength refers to the wavelength at which the emission spectral peak is located in the electroluminescence spectrum of the organic compound.

[0084] In some embodiments, the chromaticity coordinates of the emitted color of the organic compound are (x, y), where 0.13 ≤ x ≤ 0.16 and 0.06 ≤ y ≤ 0.15. It should be noted that the chromaticity coordinates are obtained by measuring the spectral distribution of the organic compound using a colorimeter and quantifying the color of light into chromaticity coordinates (x, y) using the CIE 1931 chromaticity diagram specified by the CIE (International Commission on Illumination). These coordinates can accurately assess the color performance of the sample.

[0085] In some embodiments, the organic material is a blue fluorescent material.

[0086] Please see Figure 1 This application also provides a method for preparing an organic compound, wherein the synthetic route of the organic compound is as follows:

[0087]

[0088] The method for preparing the organic compound includes the following steps:

[0089] S11. Compound a and pinacol ester of first diborate are mixed to obtain compound b; wherein the structural formula of compound a is selected from one of the following formulas:

[0090]

[0091] The structural formula of compound b is selected from one of the following:

[0092]

[0093] S12. Mix compound b and compound c to obtain compound d, wherein compound d comprises Ar2'-Ar3; wherein the structural formula of compound c is shown below:

[0094]

[0095] The structural formula of Ar2' is shown below:

[0096] The structural formula for Ar3 is selected from one of the following:

[0097] S13. Compound e and pinacol ester of second borate are mixed to obtain compound f; wherein the structural formula of compound e is shown below:

[0098]

[0099] The structural formula of compound f is shown below:

[0100]

[0101] S14. The compound d is mixed with the compound f to obtain an organic compound, the organic compound comprising: Ar1-Ar2-Ar3;

[0102] The structural formula of Ar1 is shown below:

[0103] The structural formula of Ar2 is shown below:

[0104] Where n1 is selected from integers from 0 to 5; n2 is selected from integers from 0 to 5; n3 is selected from integers from 0 to 5; n4 is selected from integers from 0 to 1; 0≤n1+n2+n3+n4≤15;

[0105] n5 is selected from integers from 0 to 10;

[0106] n6 is selected from integers from 0 to 7; n7 is selected from integers from 0 to 5; n8 is selected from integers from 0 to 5; 0 ≤ n6 + n7 + n8 ≤ 16;

[0107] n9 is selected from integers from 0 to 7; n10 is selected from integers from 0 to 5; n11 is selected from integers from 0 to 5; 0 ≤ n9 + n10 + n11 ≤ 16;

[0108] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11Each occurrence is independently selected from D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C2. 30 Alkyl, C1-C 30 One or more of alkoxy groups and aryl groups having 6 to 30 ring atoms;

[0109] X1, X2, X3, X4, and X5 are each independently selected from halogens.

[0110] It should be noted that both the first and second pinacol diborate esters are selected from pinacol diborate esters (CAS: 73183-34-3).

[0111] n1, n2, n3, n4, n5, n6, n7, n8, n9, n10, n11, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 The selection of Ar1, Ar2, Ar3, and organic compounds is described above and will not be repeated here.

[0112] In some embodiments, X1, X2, X3, X4, and X5 are each independently selected from one of -F, -Cl, -Br, and -I.

[0113] In some embodiments, compound a includes, but is not limited to, one or more of N-(4-bromophenyl)-N-phenyl-1-naphthylamine (CAS: 138310-84-6), N-(3-phenyl)-N-phenylnaphthyl-1-amine (CAS: 1224893-33-7), and 5-bromo-N,N-diphenylnaphthyl-1-amine (CAS: 227314-48-9).

[0114] In some embodiments, the molar ratio of compound a to the first pinacol diborate is 1:(1-3), for example, it can be 1:1, 1:1.5, 1:2, 1:2.5, 1:3, or any range between two values. Within the range of the molar ratio, the substitution reaction between compound a and the first pinacol diborate can be fully carried out.

[0115] In some embodiments, the reaction temperature of compound a and the first pinacol diboron ester is 50°C to 100°C, for example, 50°C, 60°C, 70°C, 80°C, 90°C, 100°C, or any range between two values; the reaction time is 10h to 20h, for example, 11h, 12h, 13h, 14h, 15h, 16h, 17h, 18h, 19h, 20h, or any range between two values. Under these reaction conditions, the reaction efficiency of compound a and the first pinacol diboron ester is high.

[0116] In some embodiments, compound b includes, but is not limited to, 6,12-dibromo. (CAS: 131222-99-6), 5,11-dibromo 2,8-Dibromo One or more of (CAS: 50637-63-3).

[0117] In some embodiments, the molar ratio of compound b to compound c is (1-3):(1-3), for example, it can be 1:1, 1:2, 1:3, 3:1, 3:2, 3:1, or any range between two values. Within the range of the molar ratio, compound b and compound c can react sufficiently.

[0118] In some embodiments, the reaction temperature of compound b and compound c is 50°C to 100°C, for example, 50°C, 60°C, 70°C, 80°C, 90°C, 100°C, or any range between two values; the reaction time is 10h to 20h, for example, 11h, 12h, 13h, 14h, 15h, 16h, 17h, 18h, 19h, 20h, or any range between two values. Under these reaction conditions, the reaction efficiency of compound b and compound c is high.

[0119] In some embodiments, the compound e includes, but is not limited to, one or more of 2-(4-bromophenyl)-4,6-diphenylpyrimidine (CAS: 457613-56-8) and 2-(3-bromophenyl)-4,6-diphenylpyrimidine (CAS: 864377-22-0).

[0120] In some embodiments, the molar ratio of compound e to the second pinacol diborate is 1:(1 to 3), for example, it can be 1:1, 1:1.5, 1:2, 1:2.5, 1:3, or any range between two values. Within the range of the molar ratio, the compound e and the second pinacol diborate can react sufficiently.

[0121] In some embodiments, the reaction temperature of compound e and the second pinacol diborate is 50°C to 100°C, for example, 50°C, 60°C, 70°C, 80°C, 90°C, 100°C, or any range between two values; the reaction time is 10h to 20h, for example, 11h, 12h, 13h, 14h, 15h, 16h, 17h, 18h, 19h, 20h, or any range between two values. Under these reaction conditions, the reaction efficiency of compound e and the second pinacol diborate is high.

[0122] In some embodiments, the molar ratio of compound d to compound f is (1-3):(1-3), for example, it can be 1:1, 1:2, 1:3, 3:1, 3:2, 3:1, or any range between two values. Within the range of the molar ratio, compound d and compound f can react sufficiently.

[0123] In some embodiments, the reaction temperature of compound d and compound f is 50°C to 100°C, for example, 50°C, 60°C, 70°C, 80°C, 90°C, 100°C, or any range between two values; the reaction time is 10h to 20h, for example, 11h, 12h, 13h, 14h, 15h, 16h, 17h, 18h, 19h, 20h, or any range between two values. Under these reaction conditions, the reaction efficiency of compound d and compound f is high.

[0124] Secondly, embodiments of this application also provide a composition comprising a solvent and the above-mentioned organic compound, or an organic compound prepared by the above-mentioned preparation method.

[0125] In some embodiments, the solvent includes a nonpolar solvent.

[0126] Furthermore, the nonpolar solvent includes one or more of the following: n-octane, isooctane, n-hexane, cyclohexane, ethyl acetate, benzene, toluene, carbon tetrachloride, carbon disulfide, diethyl ether, isopropyl ether, n-butyl ether, and diphenyl ether.

[0127] In some embodiments, the mass concentration of the organic compound in the composition is 20 mg / mL to 50 mg / mL, for example, 20 mg / mL, 25 mg / mL, 30 mg / mL, 35 mg / mL, 40 mg / mL, 45 mg / mL, 50 mg / mL, etc. Within this mass concentration range, it is beneficial for the dissolution and dispersion of the organic compound, thereby improving film-forming properties.

[0128] Thirdly, embodiments of this application also provide a thin film, the material of which includes the above-mentioned organic matter, or the organic matter prepared by the above-mentioned preparation method.

[0129] In some embodiments, the material of the film may further include a host material.

[0130] Furthermore, the mass ratio of the main material to the organic matter is (1-99):(1-99), for example, it can be 2:98, 5:95, 10:90, 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10, 95:5, 98:2 or any range between two values.

[0131] Furthermore, the mass ratio of the host material to the organic compound is (1-20):(80-99), for example, it can be 3:97, 6:94, 8:92, 10:90, 13:87, 16:84, 18:82, 20:80, or any range between two values. Thus, within the range of the stated mass ratio, the luminescent properties of the thin film can be effectively improved.

[0132] The main material is selected from one or more of the following: 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), 3,3'-bis(N-carbazole)-1,1'-biphenyl (mCBP), bis[2-((oxo)diphenylphosphino)phenyl] ether (DPEPO), 4,4'-bis(9-carbazole)biphenyl (CBP), 1,3-dicarbazole-9-ylbenzene, 1,3,5-tris(9-carbazole)benzene, 9,9-dimethyl-9H-fluorene-2,7-diyl-bis(N-phenylcarbazole), and 2,2'-binaphthyl-6,6'-diyl-bis(N-phenylcarbazole).

[0133] The film can be prepared from the above composition using conventional techniques in the art, such as spin coating.

[0134] Fourthly, please refer to Figure 2 This application also provides an optoelectronic device 100, including an anode 10, a light-emitting layer 20 and a cathode 30 stacked sequentially, wherein the material of the light-emitting layer 20 includes the above-mentioned organic matter, or an organic matter prepared by the above-mentioned preparation method, or the light-emitting layer 20 includes the above-mentioned thin film.

[0135] The optoelectronic device 100 provided in this application uses the aforementioned organic material as the material of the light-emitting layer 20. Through reasonable modulation of the excited-state properties, it can effectively utilize high-energy triplet excitons to activate thermal exciton channels, which is beneficial for preparing a high-efficiency, low-efficiency roll-off, and high-color-purity optoelectronic device 100. By adjusting the types of donor and acceptor groups, The connection mode between the nucleus and the donor and acceptor can regulate the steric hindrance and charge transfer of molecules, thereby regulating the emission spectrum and molecular aggregation mode, and thus improving the antisystem crossing from triplet exciton to singlet state, which can effectively improve the luminous efficiency and stability of optoelectronic device 100.

[0136] In some embodiments, the anode 10 and the cathode 30 each independently include a metal electrode, a carbon electrode, a doped or undoped metal oxide electrode, and a composite electrode; wherein, the material of the metal electrode is selected from one or more of Al, Ag, Cu, Mo, Au, Ba, Ca, Ni, Ir, and Mg; the material of the carbon electrode is selected from one or more of graphite, carbon nanotubes, graphene, and carbon fibers; and the material of the doped or undoped metal oxide electrode is selected from ITO, FTO, ATO, AZO, GZO, IZO, MZO, and IT. The composite electrode material is selected from one or more of ZO, ICO, AMO, SnO2, In2O3, Cd:ZnO, F:SnO2, In:SnO2, and Ga:SnO2; the composite electrode material is selected from 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, ZnS / Ag / ZnS, and ZnS / Al / ZnS. Here, " / " indicates a stacked structure; for example, the composite electrode AZO / Ag / AZO represents a three-layer stacked composite structure consisting of an AZO layer, an Ag layer, and an AZO layer.

[0137] In some embodiments, the thickness of the light-emitting layer 20 is 20nm to 50nm, for example, it can be 22nm, 25nm, 28nm, 30nm, 32nm, 35nm, 38nm, 40nm, 42nm, 45nm, 48nm, 50nm, etc.

[0138] It should be noted that the material of the light-emitting layer 20 may also include the above-mentioned main material. The mass ratio of the main material to the organic matter and the material of the main material are as described above and will not be repeated here.

[0139] In some embodiments, please refer to Figure 3 The optoelectronic device further includes a hole functional layer 40, which is located between the light-emitting layer 20 and the anode 10.

[0140] The hole functional layer 40 includes one or more of a hole injection layer and a hole transport layer. The hole transport layer is located between the hole injection layer and the light-emitting layer 20.

[0141] In some embodiments, the material of the hole functional layer 40 includes an organic p-type semiconductor material or an inorganic p-type semiconductor material, wherein the organic p-type semiconductor material includes 4,4'-N,N'-dicarbazolyl-biphenyl, N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4”-diamine, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-spiro, N,N'- bis(4-(N,N'-diphenyl-amino)phenyl)-N,N'-diphenylbenzidine, 4,4',4'-tris(N-carbazolyl)-triphenylamine, 4,4',4'-tris(carbazol-9-yl)triphenylamine, trichloroisocyanuric acid, terbium-doped phosphate-based green luminescent materials, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene, 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, poly[(9,9'-dioctylfluorene-2,7-diyl)-co-(4, 4'-(N-(4-sec-butylphenyl)diphenylamine)], poly(4-butylphenyl-diphenylamine), poly[bis(4-phenyl)(4-butylphenyl)amine], polyaniline, polypyrrole, poly(p-)phenylenevinylene, poly(phenylenevinylene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene], poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene], copper phthalocyanine, aromatic tertiary amines, polynuclear aromatic tertiary amines, 4,4'-bis(p-carbazolyl)-1, 1'-Biphenyl compounds, N,N,N',N'-tetraarylbenzidine, PEDOT, PEDOT:PSS and its derivatives, PEDOT:PSS derivatives doped with s-MoO3, poly(N-vinylcarbazole) and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, poly(spirofluorene) and its derivatives, N,N'-di(naphthyl-1-yl)-N,N'-diphenylbenzidine, spiron NPB, nanocrystalline diamond, microcrystalline cellulose and tetracyanoquinone dimethane, doped graphene, undoped graphene;The inorganic P-type semiconductor material comprises one or more of the following: first doped metal oxide particles, first undoped metal oxide particles, metal sulfides, metal selenides, and metal nitrides. The metal oxides in the first doped metal oxide particles and the first undoped metal oxide particles each independently comprise one or more of MoO3, WO3, NiO, CrO3, CuO, and V2O5. The doping element in the first doped metal oxide particles comprises one or more of Mo, W, Ni, Cr, Cu, and V. The metal sulfides comprise CuS, MoS3, and WS. One or more of the following three elements are present: the metal selenide includes one or more of MoSe3 and WSe3; the metal nitride includes p-type gallium nitride; and the doping amount of the dopant element in the first doped metal oxide particle is 0.1 wt% to 20 wt%, for example, it can be 1 wt%, 2 wt%, 3 wt%, 4 wt%, 5 wt%, 6 wt%, 7 wt%, 8 wt%, 9 wt%, 10 wt%, 11 wt%, 12 wt%, 13 wt%, 14 wt%, 15 wt%, 16 wt%, 17 wt%, 18 wt%, 19 wt%, or any range between two values.

[0142] In some embodiments, the optoelectronic device further includes an electronic functional layer 50, which is located between the light-emitting layer 20 and the anode 30.

[0143] The electronic functional layer 50 includes one or more of an electron injection layer and an electron transport layer. The electron transport layer is located between the electron injection layer and the light-emitting layer 20.

[0144] In some embodiments, the material of the electronic functional layer 50 includes an organic N-type semiconductor material or an inorganic N-type semiconductor material, wherein the organic N-type semiconductor material includes 8-hydroxyquinoline aluminum, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene, 4,7-diphenyl-1,10-o-diazaphenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole, bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum, and 2,2'-(1,3-phenyl)bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazole]. The inorganic N-type semiconductor material comprises one or more of the following: tris[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane, tetra[(m-pyridyl)-phenyl-3-yl]biphenyl, 3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3',1”-terphenyl]-3,3”-diyl]dipyridine, 1,3-bis(3,5-dipyridin-3-ylphenyl)benzene, n,n′-bis(naphthyl-1-yl)-n,n′-bis(phenyl)benzidine, and diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide; the inorganic N-type semiconductor material includes second-doped metal oxide particles, second-undoped metal oxide particles, group IIB-VIA semiconductor materials, group IIIA-VA semiconductor materials, and group IA-VIIA semiconductor materials. The semiconductor material comprises one or more of the following: semiconductor materials and IIB-IIIA-VIA group semiconductor materials. The material of the second undoped metal oxide particle includes one or more of ZnO, TiO2, SnO2, ZrO2, and Ta2O5. The metal oxide in the second doped metal oxide particle includes one or more of ZnO, TiO2, SnO2, ZrO2, Ta2O5, and Al2O3. The doping element in the second doped metal oxide particle includes one or more of Al, Mg, Li, Mn, Y, La, Cu, Ni, Zr, Ce, In, and Ga. The IIB-VIA group semiconductor material includes one or more of ZnS, ZnSe, and CdS. The A-VA group semiconductor materials include one or more of InP and GaP, the IA-VIIA group semiconductor materials include LiF, and the IB-IIIA-VIA group semiconductor materials include one or more of CuInS and CuGaS. The doping amount of the dopant element in the second doped metal oxide particle is 0.1wt% to 20wt%, for example, it can be 1wt%, 2wt%, 3wt%, 4wt%, 5wt%, 6wt%, 7wt%, 8wt%, 9wt%, 10wt%, 11wt%, 12wt%, 13wt%, 14wt%, 15wt%, 16wt%, 17wt%, 18wt%, 19wt%, or any range between two values.

[0145] It should be noted that other conventional film layers in the field may also be provided in the above-mentioned optoelectronic device 100 as needed, such as an exciton blocking layer located between the hole functional layer 40 and the light-emitting layer 20. The material of the exciton blocking layer can refer to the material of the hole functional layer 40 mentioned above.

[0146] This application embodiment also provides a display device, which includes the above-described optoelectronic device 100.

[0147] 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.

[0148] The present application will be specifically described below through specific embodiments. The following embodiments are only some embodiments of the present application and are not intended to limit the present application.

[0149] Example 1

[0150] This embodiment provides an organic compound M1, the synthetic route of which is as follows:

[0151]

[0152] The specific preparation method is as follows:

[0153] (1) Synthesis of Compound 1: Under a nitrogen atmosphere, N-(4-bromophenyl)-N-phenyl-1-naphthylamine (26.72 mmol) and pinacol diborate (29.39 mmol) were added to a 250 mL double-necked flask and stirred with 100 mL of 1,4-dioxane until completely dissolved. Then, [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (1.07 mmol) and potassium acetate (632.92 mmol) were added, and the mixture was heated to 80 °C and stirred for 12 hours before post-treatment. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, obtaining the crude product, further purification of the crude product, and separation of the product using a chromatography column (eluent: petroleum ether); finally, compound 1 was obtained with a yield of 88.61%.

[0154] Among them, compound 1 1¹H NMR (500MHz, Chloroform-d) values ​​are as follows: δ 8.19–8.13 (m, 1H), 7.84 (dt, J = 7.8, 1.5Hz, 1H), 7.75 (dt, J = 8.0, 1.2Hz, 1H), 7.60–7.57 (m, 2H), 7.57–7.54 (m, 1H), 7.54–7.49 (m, 1H). 7.46(dd,J=7.9,7.1Hz,1H),7.28(tt,J=7.6,1.5Hz,2H),7.19(dt,J=7.1,0.8Hz,1H ),7.16-7.13(m,2H),7.13-7.10(m,2H),7.04(tt,J=7.7,1.4Hz,1H),1.24(s,12H).

[0155] (2) Synthesis of compound 2: Under a nitrogen atmosphere, compound 1 (23.73 mmol) and 6,12-dibromodimethylamine were synthesized. (26.11 mmol) was added to a 250 mL double-necked flask and stirred with 100 mL of toluene until completely dissolved. Then, tetra(triphenylphosphine)palladium (1.19 mmol), tetrabutylammonium bromide (1.19 mmol), and potassium carbonate (237.33 mmol) were added. The mixture was heated to 90 °C and stirred for 12 hours before post-treatment. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, obtaining the crude product, further purification of the crude product, and separation of the product using a chromatography column (eluent: petroleum ether); finally, compound 2 was obtained in 89.10% yield.

[0156] Among them, compound 2 1 H NMR (500MHz, Chloroform-d) is as follows: δ8.89(s,1H),8.53-8.47(m,2H),8.31-8.26(m,1H),8.20-8.15(m,2H),7.94-7.87(m,1H),7.84(dt,J=8.0,1. 7Hz,1H),7.75(dt,J=8.1,1.3Hz,1H),7.62-7.43(m,9H),7.32-7.25(m, 2H),7.24-7.17(m,3H),7.14-7.08(m,2H),7.04(tt,J=7.7,1.4Hz,1H).

[0157] (3) Synthesis of Compound 3: Under a nitrogen atmosphere, 2-(4-bromophenyl)-4,6-diphenylpyrimidine (25.82 mmol) and pinacol diborate (28.40 mmol) were added to a 250 mL double-necked flask and stirred with 100 mL of 1,4-dioxane until completely dissolved. Then, [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (1.29 mmol) and potassium acetate (258.21 mmol) were added, and the mixture was heated to 80 °C and stirred for 12 hours before post-treatment. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, obtaining the crude product, further purification of the crude product, and separation of the product using a chromatography column (eluent: petroleum ether); finally, compound 3 was obtained with a yield of 91.04%.

[0158] Among them, compound 3 1 ¹H NMR (500MHz, Chloroform-d) values ​​are as follows: δ 8.08–8.06 (m, 4H), 8.04 (s, 1H), 7.98 (d, J = 8.4 Hz, 2H), 7.55–7.52 (m, 2H), 7.51–7.47 (m, 4H), 7.44–7.40 (m, 2H), 1.24 (s, 12H).

[0159] (4) Synthesis of organic compound M1: Compound 2 (16.65 mmol), compound 3 (18.32 mmol), tetra(triphenylphosphine)palladium (0.83 mmol), tetrabutylammonium bromide (0.83 mmol), and potassium carbonate (166.51 mmol) were placed in a 250 mL round-bottom flask under nitrogen atmosphere; then 100 mL of toluene was added, and the mixture was stirred and heated to 90 °C for 12 hours; when the reaction was cooled to room temperature, post-treatment was performed. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, drying of the extract on anhydrous magnesium sulfate and evaporation under reduced pressure to obtain a crude product, further purification of the crude product, and separation of the product using a chromatography column (eluent: dichloromethane: petroleum ether = 1:1); finally, organic compound M1 was obtained with a yield of 87.03%.

[0160] Among them, organic matter M1 1H NMR (500MHz, Chloroform-d) is as follows: δ8.48(s,1H),8.44(s,1H),8.21-8.13(m,3H),8.09-8.04(m ,7H),7.91-7.89(m,2H),7.84(dt,J=8.0,1.7Hz,1H),7.75(dt,J=8.0,1.3Hz,1H),7.58-7.5 6(m,7H),7.55-7.50(m,3H),7.49(dd,J=7.7,1.3Hz,4H),7.45(d,J=7.6Hz,1H),7.44-7.39( m,2H),7.32-7.25(m,2H),7.23-7.19(m,3H),7.13-7.10(m,2H),7.04(tt,J=7.7,1.4Hz,1H).

[0161] Example 2

[0162] This embodiment provides an organic compound M13, the synthetic route of which is as follows:

[0163]

[0164]

[0165] The specific preparation method is as follows:

[0166] (1) Synthesis of Compound 4: Under a nitrogen atmosphere, N-(3-phenyl)-N-phenylnaphth-1-amine (26.72 mmol) and pinacol diborate (29.39 mmol) were added to a 250 mL double-necked flask and stirred with 100 mL of 1,4-dioxane until completely dissolved. Then, [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (1.07 mmol) and potassium acetate (632.92 mmol) were added, and the mixture was heated to 80 °C and stirred for 12 hours before post-treatment. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, obtaining the crude product, further purification of the crude product, and separation of the product using a chromatography column (eluent: petroleum ether); finally, compound 4 was obtained with a yield of 90.07%.

[0167] Among them, compound 4 1H NMR (500MHz, Chloroform-d) is as follows: δ8.19-8.13(m,1H),7.84(dt,J=7.8,1.6Hz,1H),7.75(dt,J=7.9,1.1Hz,1H),7.60-7.52(m, 2H),7.52-7.43(m,2H),7.32-7.24(m,4H),7.19(dd,J=7.1,1.3Hz,1H),7.14-7.09(m,2H),7.08-7.00(m,2H),1.24(s,12H).

[0168] (2) Synthesis of compound 5: Under a nitrogen atmosphere, compound 4 (22.79 mmol) and 5,11-dibromodimethylamine were synthesized. (20.72 mmol) was added to a 250 mL double-necked flask and stirred with 100 mL of toluene until completely dissolved. Then, tetra(triphenylphosphine)palladium (1.04 mmol), tetrabutylammonium bromide (1.04 mmol), and potassium carbonate (207.21 mmol) were added. The mixture was heated to 90 °C and stirred for 12 hours before post-treatment. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, and further purification of the crude product using column chromatography (eluent: petroleum ether). Compound 5 was finally obtained in 83.25% yield.

[0169] Among them, compound 5 1 H NMR (500MHz, Chloroform-d) is as follows: δ8.43(d,J=1.8Hz,1H),8.27-8.20(m,1H),8.16(dt ,J=5.5,1.6Hz,4H),7.94-7.86(m,1H),7.84(dt,J=7.9,1.6Hz,1H),7.75(dt,J=8.1, 1.3Hz,1H),7.58-7.50(m,6H),7.46(t,J=7.5Hz,1H),7.42(dd,J=7.8,7.1Hz,1H),7 .34-7.25(m,4H),7.22-7.15(m,2H),7.14-7.08(m,2H),7.04(tt,J=7.7,1.4Hz,1H).

[0170] (3) Synthesis of Compound 6: Under a nitrogen atmosphere, 2-(3-bromophenyl)-4,6-diphenylpyrimidine (25.82 mmol) and pinacol diborate (28.40 mmol) were added to a 250 mL double-necked flask and stirred with 100 mL of 1,4-dioxane until completely dissolved. Then, [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (1.29 mmol) and potassium acetate (258.21 mmol) were added, and the mixture was heated to 80 °C and stirred for 12 hours before post-treatment. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, obtaining the crude product, further purification of the crude product, and separation of the product using a chromatography column (eluent: petroleum ether); finally, compound 6 was obtained with a yield of 89.25%.

[0171] Among them, compound 6 1 H NMR (500MHz, Chloroform-d) is as follows: δ8.10-8.06(m,4H),8.05(s,1H),8.01(ddd,J=8.6,2.2,1.1Hz,1H),7.77(ddd,J=6.9,2 .2,1.1Hz,1H),7.64(t,J=2.1Hz,1H),7.56(dd,J=8.6,7.1Hz,1H),7.52-7.47(m,4H),7.44-7.39(m,2H),1.24(s,12H).

[0172] (4) Synthesis of compound M13: Compound 5 (16.65 mmol), compound 6 (18.32 mmol), tetra(triphenylphosphine)palladium (0.83 mmol), tetrabutylammonium bromide (0.83 mmol), and potassium carbonate (116.51 mmol) were placed in a 250 mL round-bottom flask under nitrogen atmosphere; then 100 mL of toluene was added, and the mixture was stirred and heated to 90 °C for 12 hours; when the reaction was cooled to room temperature, post-treatment was performed. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, drying of the extract on anhydrous magnesium sulfate and evaporation under reduced pressure to obtain the crude product, further purification of the crude product, and separation of the product using a chromatography column (eluent: dichloromethane: petroleum ether = 1:1); finally, organic compound M13 was obtained with a yield of 84.42%.

[0173] Among them, organic compound M13 1¹H NMR (500MHz, Chloroform-d) values ​​are as follows: δ 8.68 (t, J = 2.2Hz, 1H), 8.54 (d, J = 2.1Hz, 1H), 8.43 (d, J = 1.8Hz, 1H), 8.19–8.11 (m, 3H), 8.10–8.04 (m, 5H), 8.01 (ddd, J = 9.3, 2.2, 1.2Hz, 1H), 7.93–7.88 (m, 2H). ,7.84(dt,J=8.0,1.7Hz,1H),7.78-7.69(m,2H),7.57-7.53(m,5H),7.52-7.44(m,7H),7.44-7. 39(m,3H),7.35-7.25(m,4H),7.22-7.15(m,2H),7.14-7.08(m,2H),7.04(tt,J=7.7,1.4Hz,1H).

[0174] Example 3

[0175] This embodiment provides an organic compound M4, the synthetic route of which is as follows:

[0176]

[0177]

[0178] The specific preparation method is as follows:

[0179] (1) Synthesis of Compound 7: Under a nitrogen atmosphere, 5-bromo-N,N-diphenylnaphth-1-amine (26.72 mmol) and pinacol diborate (29.39 mmol) were added to a 250 mL double-necked flask and stirred with 100 mL of 1,4-dioxane until completely dissolved. Then, [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (1.07 mmol) and potassium acetate (632.92 mmol) were added, and the mixture was heated to 80 °C and stirred for 12 hours before post-treatment. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, obtaining the crude product, further purification of the crude product, and separation of the product using a chromatography column (eluent: petroleum ether); finally, compound 7 was obtained with a yield of 89.53%.

[0180] Among them, compound 7 1H NMR (500MHz, Chloroform-d) is as follows: δ8.21-8.15(m,1H),7.63-7.57(m,1H),7.53(dt,J=7.2,0.8Hz,1H),7.46(t,J=7.3H z,1H),7.36-7.25(m,5H),7.22(dd,J=7.0,1.4Hz,1H),7.14-7.08(m,4H),7.04(tt,J=7.7,1.4Hz,2H),1.24(s,12H).

[0181] (2) Synthesis of compound 8: Under a nitrogen atmosphere, compound 7 (23.73 mmol) and 6,12-dibromodimethylamine were synthesized. (21.58 mmol) was added to a 250 mL double-necked flask and stirred with 100 mL of toluene until completely dissolved. Then, tetra(triphenylphosphine)palladium (1.08 mmol), tetrabutylammonium bromide (1.08 mmol), and potassium carbonate (215.76 mmol) were added. The mixture was heated to 90 °C and stirred for 12 hours before post-treatment. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, and further purification of the crude product using column chromatography (eluent: petroleum ether). Compound 8 was finally obtained in 89.99% yield.

[0182] Among them, compound 8 1 H NMR (500MHz, Chloroform-d) is as follows: δ8.91(s,1H),8.55-8.47(m,2H),8.33-8.25(m,1H),8.17(m,1H),8.11-8.03(m,1H),7.94-7.87(m,1H), 7.77-7.71(m,1H),7.58-7.54(m,4H),7.51-7.43(m,3H),7.28(s,4H),7.23-7.18(m,1H),7.12-7.10(m,4H),7.04(tt,J=7.7,1.4Hz,2H).

[0183] (3) Synthesis of Compound 9: Under a nitrogen atmosphere, 2-(4-bromophenyl)-4,6-diphenylpyrimidine (25.82 mmol) and pinacol diborate (28.40 mmol) were added to a 250 mL double-necked flask and stirred with 100 mL of 1,4-dioxane until completely dissolved. Then, [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (1.29 mmol) and potassium acetate (258.21 mmol) were added, and the mixture was heated to 80 °C and stirred for 12 hours before post-treatment. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, obtaining the crude product, further purification of the crude product, and separation of the product using a chromatography column (eluent: petroleum ether); finally, compound 9 was obtained with a yield of 91.04%.

[0184] Among them, compound 9 1 ¹H NMR (500MHz, Chloroform-d) values ​​are as follows: δ 8.08–8.06 (m, 4H), 8.04 (s, 1H), 7.98 (d, J = 8.4 Hz, 2H), 7.55–7.52 (m, 2H), 7.51–7.47 (m, 4H), 7.44–7.40 (m, 2H), 1.24 (s, 12H).

[0185] (4) Synthesis of compound M4: Compound 8 (16.65 mmol), compound 9 (18.32 mmol), tetra(triphenylphosphine)palladium (0.32 mmol), tetrabutylammonium bromide (0.83 mmol), and potassium carbonate (166.51 mmol) were placed in a 250 mL round-bottom flask under nitrogen atmosphere. Then, 100 mL of toluene was added, and the mixture was stirred and heated to 90 °C for 12 hours. When the reaction was cooled to room temperature, post-treatment was performed. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, drying of the extract on anhydrous magnesium sulfate and evaporation under reduced pressure to obtain a crude product, further purification of the crude product, and separation of the product using a chromatography column (eluent: dichloromethane: petroleum ether = 1:1). Finally, organic compound M4 was obtained with a yield of 68.47%.

[0186] Among them, organic matter M4 1H NMR (500MHz, Chloroform-d) is as follows: δ8.53 (s, 1H), 8.44 (s, 1H), 8.22-8.14 (m, 2H), 8.10-8.06 (m, 5H), 8.04 (d, J = 0.7Hz, 3H), 7.94-7.86 (m, 2H), 7.74 ( dd,J=7.9,1.4Hz,1H),7.59-7.55(m,6H),7.51-7.42(m,9H),7.32-7.25( m,4H),7.23-7.18(m,1H),7.14-7.08(m,4H),7.04(tt,J=7.7,1.4Hz,2H).

[0187] Example 4

[0188] This embodiment provides an organic compound M19, the synthetic route of which is as follows:

[0189]

[0190] The specific preparation method is as follows:

[0191] (1) Synthesis of Compound 10: Under a nitrogen atmosphere, N-(3-phenyl)-N-phenylnaphth-1-amine (26.72 mmol) and pinacol diborate (29.39 mmol) were added to a 250 mL double-necked flask and stirred with 100 mL of 1,4-dioxane until completely dissolved. Then, [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (1.07 mmol) and potassium acetate (632.92 mmol) were added, and the mixture was heated to 80 °C and stirred for 12 hours before post-treatment. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, obtaining the crude product, further purification of the crude product, and separation of the product using a chromatography column (eluent: petroleum ether); finally, compound 10 was obtained in a yield of 90.07%.

[0192] Among them, compound 10 1¹H NMR (500MHz, Chloroform-d) values ​​are as follows: δ 8.19–8.13 (m, 1H), 7.84 (dt, J = 7.8, 1.5Hz, 1H), 7.75 (dt, J = 8.0, 1.2Hz, 1H), 7.60–7.57 (m, 2H), 7.57–7.54 (m, 1H), 7.54–7.49 (m, 1H). 7.46(dd,J=7.9,7.1Hz,1H),7.28(tt,J=7.6,1.5Hz,2H),7.19(dt,J=7.1,0.8Hz,1H ),7.16-7.13(m,2H),7.13-7.10(m,2H),7.04(tt,J=7.7,1.4Hz,1H),1.24(s,12H).

[0193] (2) Synthesis of compound 11: Under a nitrogen atmosphere, compound 4 (22.79 mmol) and 5,11-dibromo ... (20.72 mmol) was added to a 250 mL double-necked flask and stirred with 100 mL of toluene until completely dissolved. Then, tetra(triphenylphosphine)palladium (1.04 mmol), tetrabutylammonium bromide (1.04 mmol), and potassium carbonate (207.21 mmol) were added. The mixture was heated to 90 °C and stirred for 12 hours before post-treatment. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, and further purification of the crude product using column chromatography (eluent: petroleum ether). Compound 5 was finally obtained in 83.25% yield.

[0194] Among them, compound 11 1 H NMR (500MHz, Chloroform-d) is as follows: δ8.65 (dd, J=19.4, 9.0Hz, 2H), 8.47 (dd, J=8.9, 6.3Hz, 2H), 8.22 (t, J=2.3Hz,1H),8.19-8.13(m,1H),8.13-8.05(m,3H),7.96(dd,J=9.2,2.3Hz,1H),7.84(dt,J=8.0,1. 6Hz,1H),7.75(dt,J=8.0,1.2Hz,1H),7.70(dd,J=8.5,1.9Hz,1H),7.58-7.53(m,4H),7.48-7.43(m, 1H),7.28(tt,J=7.6,1.5Hz,2H),7.22-7.19(m,3H),7.13-7.10(m,2H),7.04(tt,J=7.7,1.4Hz,1H).

[0195] (3) Synthesis of Compound 12: Under a nitrogen atmosphere, 2-(3-bromophenyl)-4,6-diphenylpyrimidine (25.82 mmol) and pinacol diborate (28.40 mmol) were added to a 250 mL double-necked flask and stirred with 100 mL of 1,4-dioxane until completely dissolved. Then, [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (1.29 mmol) and potassium acetate (258.21 mmol) were added, and the mixture was heated to 80 °C and stirred for 12 hours before post-treatment. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, obtaining the crude product, further purification of the crude product, and separation of the product using a chromatography column (eluent: petroleum ether); finally, compound 6 was obtained with a yield of 89.25%.

[0196] Among them, compound 12 1 H NMR (500MHz, Chloroform-d) is as follows: δ8.10-8.06(m,4H),8.05(s,1H),8.01(ddd,J=8.6,2.2,1.1Hz,1H),7.77(ddd,J=6.9,2 .2,1.1Hz,1H),7.64(t,J=2.1Hz,1H),7.56(dd,J=8.6,7.1Hz,1H),7.52-7.47(m,4H),7.44-7.39(m,2H),1.24(s,12H).

[0197] (4) Synthesis of compound M19: Compound 11 (16.65 mmol), compound 12 (18.32 mmol), tetra(triphenylphosphine)palladium (0.83 mmol), tetrabutylammonium bromide (0.83 mmol), and potassium carbonate (166.51 mmol) were placed in a 250 mL round-bottom flask under nitrogen atmosphere; then 100 mL of toluene was added, and the mixture was stirred and heated to 90 °C for 12 hours; when the reaction was cooled to room temperature, post-treatment was performed. Post-treatment included extraction with dichloromethane and water, separation of the organic phase DCM solvent, drying of the extract on anhydrous magnesium sulfate and evaporation under reduced pressure to obtain a crude product, further purification of the crude product, and separation of the product using a chromatography column (eluent: dichloromethane: petroleum ether = 1:1); finally, organic compound M19 was obtained with a yield of 68.84%.

[0198] Among them, organic compound M19 1H NMR (500MHz, Chloroform-d) is as follows: δ8.64(dd,J=12.2,9.0Hz,2H),8.52(t,J=1.9Hz,1H),8.48(d,J=9.3Hz,2 H),8.37(t,J=2.2Hz,1H),8.22(t,J=2.3Hz,1H),8.16(dd,J=7.6,1.3Hz,1H),8.12-8.03(m,7H),8.03-7. 93(m,3H),7.84(dt,J=7.9,1.6Hz,1H),7.75(dt,J=8.1,1.3Hz,1H),7.64-7.54(m,5H),7.52-7.45(m,6H) ,7.44-7.39(m,2H),7.32-7.25(m,2H),7.23-7.17(m,3H),7.14-7.08(m,2H),7.04(tt,J=7.7,1.4Hz,1H).

[0199] Comparative Example 1

[0200] Comparative Example 1 provides an organic compound P1, the structural formula of which is as follows:

[0201]

[0202] Comparative Example 2

[0203] Comparative Example 2 provides an organic compound P2, whose structural formula is as follows:

[0204]

[0205] Comparative Example 3

[0206] Comparative Example 3 provides an organic compound P3, whose structural formula is as follows:

[0207]

[0208] The UV-Vis absorption spectra, steady-state fluorescence spectra, and TGA (thermogravimetric analysis) of the organic compounds provided in Examples 1-4 in toluene solution were measured, and the results were referred to as follows: Figure 4 , Figure 5 and Figure 6 .

[0209] The UV-Vis absorption spectroscopy instrument was a Shimadzu UV-3600, and the steady-state fluorescence spectroscopy instrument was a Shimadzu RF-5301. All solutions used in the solution-state tests were toluene solutions with a concentration of 10%. -5The TGA (thermogravimetric analysis) plot was obtained by using a Netzsch TG 209 thermogravimetric analysis instrument in an N2 atmosphere with a heating rate of 10 °C / min.

[0210] Depend on Figure 4 It can be seen from the absorption of light in the ultraviolet and visible light regions that the absorption of M1, M13, M4 and M19 is all before 400nm, and the peak at 350nm is the main absorption peak of the material, which can be identified as π-π transition.

[0211] Depend on Figure 5 It can be seen that the steady-state fluorescence spectrum reflects that the emission of M1, M13, M4 and M19 is all before 450nm, indicating that M1, M13, M4 and M19 have good blue light characteristics.

[0212] Depend on Figure 6 It is known that thermogravimetric analysis is an analytical method that studies the thermal stability, decomposition behavior and composition of materials by measuring the mass loss of materials as a function of temperature or time. As the temperature increases, organic compounds M1, M13, M4 and M19 achieve a 5% thermogravimetric loss at 350℃, and have good thermal stability in vapor deposition.

[0213] Device Example 1

[0214] This embodiment provides an optoelectronic device, the fabrication method of which is as follows:

[0215] Take a pre-made indium tin oxide (ITO) glass with a sheet resistance of 15Ω, and clean it ultrasonically with acetone, detergent, deionized water and isopropanol in sequence. Then, treat it with plasma for 10 minutes to form an anode.

[0216] The cleaned ITO glass sheet is placed in a vacuum evaporation equipment, and a 40nm layer of polyethylene dioxythiophene-doped poly(styrene sulfonate) (PEDOT:PSS) is spin-coated on the ITO surface to form a hole injection layer.

[0217] TFB solution was spin-coated onto the hole injection layer to form a 40nm hole transport layer;

[0218] A dispersion of organic compound M1 from Example 1 was spin-coated onto the hole transport layer to form a 20 nm light-emitting layer.

[0219] A 30 nm layer of 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi) was spin-coated onto the light-emitting layer to form an electron transport layer;

[0220] Lithium fluoride (LiF) is deposited on the electron transport layer to form a 1nm electron injection layer;

[0221] A 100nm cathode is formed on the electron injection layer by thermal evaporation of Al, and then packaged to obtain an optoelectronic device.

[0222] Device Examples 2-4

[0223] Device Examples 2 to 4 are basically the same as Device Example 1, except that in Device Examples 2 to 3, the organic compound M1 in Example 1 is replaced with M13, M4 and M19 in Examples 2 to 4 respectively.

[0224] Device Example 5

[0225] This embodiment provides an optoelectronic device, the fabrication method of which is as follows:

[0226] Take a pre-made indium tin oxide (ITO) glass with a sheet resistance of 15Ω, and clean it ultrasonically with acetone, detergent, deionized water and isopropanol in sequence. Then, treat it with plasma for 10 minutes to form an anode.

[0227] The cleaned ITO glass sheet is placed in a vacuum evaporation equipment, and a 40nm layer of polyethylene dioxythiophene-doped poly(styrene sulfonate) (PEDOT:PSS) is spin-coated on the ITO surface to form a hole injection layer.

[0228] TFB solution was spin-coated onto the hole injection layer to form a 40nm hole transport layer;

[0229] The organic compound M1 from Example 1 and the host material 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi) were mixed at a mass ratio of 98:2 and disposed on the hole transport layer to form a 20nm light-emitting layer;

[0230] A 30 nm layer of 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi) was spin-coated onto the light-emitting layer to form an electron transport layer;

[0231] Lithium fluoride (LiF) is deposited on the electron transport layer to form a 1nm electron injection layer;

[0232] A 100nm cathode is formed on the electron injection layer by thermal evaporation of Al, and then packaged to obtain an optoelectronic device.

[0233] Device Examples 6-8

[0234] Device Examples 6-8 are basically the same as Device Example 5, except that in Device Examples 6-8, the organic compound M1 of Example 1 in Example 5 is replaced with M13, M4 and M19 in Examples 2-4 respectively.

[0235] Device Comparison Examples 1-3

[0236] The devices in Comparative Examples 1 to 3 are basically the same as those in Device Example 1, except that the organic compound M1 in Device Comparative Examples 1 to 3 is replaced with P1, P2 and P3 in Comparative Examples 1 to 3, respectively.

[0237] Device Comparison Examples 4-6

[0238] The devices in Comparative Examples 4 to 6 are basically the same as those in Device Example 5, except that the organic compound M1 in Example 1 is replaced with P1, P2 and P3 in Comparative Examples 1 to 3 in Device Comparative Examples 4 to 6, respectively.

[0239] The electroluminescence spectra of the optoelectronic devices provided in Examples 5-8 are measured, and the results are shown in Table 7.

[0240] The on-time voltage and maximum brightness L of the optoelectronic devices provided in Examples 1-8 and Comparative Examples 1-6 were measured. max Maximum external quantum efficiency (EQE) max The results, including the color coordinates, are shown in Table 1.

[0241] The test method for the start-up voltage is as follows: the voltage value when the brightness reaches 1 nit is obtained using an efficiency test system built with Keithley 6485, which is the start-up voltage.

[0242] Maximum brightness L max The testing method is as follows: using the Fostar FPD optical property measurement equipment, the efficiency testing system built by controlling the QE PRO spectrometer and Keithley 6485 through LabVIEW is used to measure the maximum brightness;

[0243] Maximum external quantum efficiency EQE max The testing method is as follows:

[0244] The ratio of electron-hole pairs injected into a quantum dot to emitted photons, expressed as a percentage (%), is an important parameter for evaluating the quality of electroluminescent devices. It can be measured using an EQE optical testing instrument. The specific calculation formula is as follows:

[0245]

[0246] Where ηe is the optical output coupling efficiency, ηr is the ratio of recombination carriers to injected carriers, χ is the ratio of the number of excitons generating photons to the total number of excitons, and K R K is the radiation process rate. NR This represents the rate of a non-radiative process.

[0247] Test conditions: Conducted at room temperature with an air humidity of 30-60%.

[0248] Color coordinates are obtained by measuring the spectral distribution of a luminescent sample using a colorimeter and quantifying the color of light into color coordinates (x, y) using the CIE 1931 chromaticity diagram, which is specified by the CIE (International Commission on Illumination). These coordinates can accurately evaluate the color performance of the sample.

[0249] Table 1

[0250]

[0251] Depend on Figure 7 As shown in Table 1:

[0252] As can be seen from Device Examples 1-4 and Comparative Examples 1-3, using the materials of Examples 1-4 and Comparative Examples 1-3 as the light-emitting layer material effectively reduces the turn-on voltage of the optoelectronic device (<4V), thereby improving the reliability of the optoelectronic device, reducing power consumption, and also increasing the maximum brightness of the optoelectronic device (>12000cd / m²). 2 The maximum external quantum efficiency (>7%) and color coordinates indicate that the optoelectronic device provided in this application exhibits blue light emission;

[0253] Depend on Figure 7 As shown in Device Examples 5-8 and Device Comparative Examples 4-6, when the materials of Examples 1-4 and Comparative Examples 1-3 are used together with the main material as the material of the light-emitting layer, the electroluminescence spectrum of the optoelectronic device is almost the same as the steady-state fluorescence spectrum of the organic material. This indicates that the organic material provided in this application is suitable as a blue light material to improve the performance of the optoelectronic device. The emission spectrum peaks of Device Examples 5-8 are all around 460 nm, showing pure blue light emission. The turn-on voltage of the optoelectronic device provided by the device examples is significantly reduced, while the maximum brightness and maximum external quantum efficiency are significantly increased, thus improving the luminous efficiency and stability of the optoelectronic device.

[0254] 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, The organic compounds include: Ar1-Ar2-Ar3; wherein... The structural formula of Ar1 is shown below: The structural formula of Ar2 is shown below: The structural formula for Ar3 is selected from one of the following: Where n1 is selected from integers from 0 to 5; n2 is selected from integers from 0 to 5; n3 is selected from integers from 0 to 5; n4 is selected from integers from 0 to 1; 0≤n1+n2+n3+n4≤15; n5 is selected from integers from 0 to 10; n6 is selected from integers from 0 to 7; n7 is selected from integers from 0 to 5; n8 is selected from integers from 0 to 5; 0 ≤ n6 + n7 + n8 ≤ 16; n9 is selected from integers from 0 to 7; n10 is selected from integers from 0 to 5; n11 is selected from integers from 0 to 5; 0 ≤ n9 + n10 + n11 ≤ 16; R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 each occurrence is independently selected from one or more of D, amino, halogen, hydroxy, carboxy, nitro, sulfonic acid, mercapto, cyano, C1-C 30 alkyl, C1-C 30 alkoxy, aryl having 6 to 30 ring atoms.

2. The organic compound as described in claim 1, characterized in that, It also includes at least one of the following features (1) to (7): (1) n1 is selected from integers from 0 to 3; n2 is selected from integers from 0 to 3; n3 is selected from integers from 0 to 3; n4 is selected from integers from 0 to 1; 0≤n1+n2+n3+n4≤10; (2) n5 is selected from integers from 0 to 6; (3) n6 is selected from integers from 0 to 5; n7 is selected from integers from 0 to 3; n8 is selected from integers from 0 to 3; 0≤n6+n7+n8≤10; (4) n9 is selected from integers from 0 to 5; n10 is selected from integers from 0 to 3; n11 is selected from integers from 0 to 3; 0≤n9+n10+n11≤10; (5) R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 each occurrence is independently selected from one or more of D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C 20 alkyl, C1-C 20 alkoxy, aryl having 6 to 24 ring atoms; (6)R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 Each occurrence is independently selected from D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C2. 10 Alkyl, C1-C 10 One or more of alkoxy groups and aryl groups having 6 to 18 ring atoms; (7)R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 Each occurrence is independently selected from one or more of D, amino, hydroxyl, nitro, C1-C8 alkyl, C1-C8 alkoxy, and aryl groups with 6-12 ring atoms.

3. The organic compound as described in claim 1, characterized in that, Ar1 is selected from one of the following structural formulas: Ar2 is selected from one of the following structural formulas: Ar3 is selected from one of the following structural formulas:

4. The organic compound as described in claim 1, characterized in that, Ar1 is selected from one of the following structural formulas: Ar2 is selected from one of the following structural formulas: Ar3 is selected from one of the following structural formulas:

5. The organic compound as described in claim 1, characterized in that, The organic compound is selected from one of the following structures: M1 to M30: The emission peak wavelength of the organic compound is 440 nm to 480 nm; and / or The color coordinates of the luminescent color of the organic compound are (x, y), where 0.13 ≤ x ≤ 0.16 and 0.06 ≤ y ≤ 0.

15.

6. A composition, characterized in that, The composition includes a solvent and an organic compound as described in any one of claims 1 to 5.

7. The composition according to claim 6, characterized in that, The solvent includes a nonpolar solvent, which includes one or more of the following: n-octane, isooctane, n-hexane, cyclohexane, ethyl acetate, benzene, toluene, carbon tetrachloride, carbon disulfide, diethyl ether, isopropyl ether, n-butyl ether, and diphenyl ether; and / or In the composition, the mass concentration of the organic compound is 20 mg / mL to 50 mg / mL.

8. A thin film, characterized in that, The material of the film includes the organic compounds as described in any one of claims 1 to 5.

9. The thin film as claimed in claim 8, characterized in that, The material of the thin film also includes a host material; wherein... The mass ratio of the main material to the organic matter is (1-99):(1-99); optionally, the mass ratio of the main material to the organic matter is (1-20):(80-99). The main material is selected from one or more of the following: 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl, 3,3'-bis(N-carbazole)-1,1'-biphenyl, bis[2-((oxo)diphenylphosphino)phenyl] ether, 4,4'-bis(9-carbazole)biphenyl, 1,3-dicarbazole-9-ylbenzene, 1,3,5-tris(9-carbazole)benzene, 9,9-dimethyl-9H-fluorene-2,7-diyl-bis(N-phenylcarbazole), and 2,2'-binaphthyl-6,6'-diyl-bis(N-phenylcarbazole).

10. An optoelectronic device, characterized in that, It includes an anode, a light-emitting layer, and a cathode stacked sequentially, wherein the material of the light-emitting layer includes an organic compound as described in any one of claims 1 to 5, or the light-emitting layer includes a thin film as described in any one of claims 8 to 9.

11. The optoelectronic device as described in claim 10, characterized in that, The anode and the cathode each independently include a metal electrode, a carbon electrode, a doped or undoped metal oxide electrode, and a composite electrode; wherein, the material of the metal electrode is selected from one or more of Al, Ag, Cu, Mo, Au, Ba, Ca, Ni, Ir, and Mg; the material of the carbon electrode is selected from one or more of graphite, carbon nanotubes, graphene, and carbon fibers; the material of the doped or undoped metal oxide electrode is selected from ITO, FTO, ATO, AZO, GZO, IZO, MZO, ITZO, ICO, etc. AMO, SnO2, In2O3, Cd:ZnO, F:SnO2, In:SnO2, Ga:SnO2; the composite electrode material is selected from 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, ZnS / Ag / ZnS, and ZnS / Al / ZnS; and / or The optoelectronic device further includes a hole functional layer located between the light-emitting layer and the anode; the material of the hole functional layer includes organic P-type semiconductor materials or inorganic P-type semiconductor materials, wherein the organic P-type semiconductor material includes 4,4'-N,N'-dicarbazolyl-biphenyl, N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4”-diamine, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4’-diamine, and N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4’-diamine. )-N,N'-bis(phenyl)-spiro, N,N'-bis(4-(N,N'-diphenyl-amino)phenyl)-N,N'-diphenylbenzidine, 4,4',4'-tris(N-carbazolyl)-triphenylamine, 4,4',4'-tris(carbazol-9-yl)triphenylamine, trichloroisocyanuric acid, terbium-doped phosphate-based green luminescent materials, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzphenanthrene, 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, poly[(9,9'-dioctylfluorene-2 ,7-dimethyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))], poly(4-butylphenyl-diphenylamine), poly[bis(4-phenyl)(4-butylphenyl)amine], polyaniline, polypyrrole, poly(p-)phenylenevinylene, poly(phenylenevinylene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene], poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene], copper phthalocyanine, aromatic tertiary amines, polynuclear aromatic tertiary amines, 4,4'-bis(p-)phenylenevinylene Carbazolyl)-1,1'-biphenyl compounds, N,N,N',N'-tetraaryl benzidine, PEDOT, PEDOT:PSS and its derivatives, PEDOT:PSS derivatives doped with s-MoO3, poly(N-vinylcarbazole) and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, poly(spirofluorene) and its derivatives, N,N'-di(naphthyl-1-yl)-N,N'-diphenylbenzidine, spironolactone (NPB), nanocrystalline diamond, microcrystalline cellulose and tetracyanoquinone dimethane, doped graphene, undoped graphene;The inorganic P-type semiconductor material comprises one or more of the following: first doped metal oxide particles, first undoped metal oxide particles, metal sulfide, metal selenide, and metal nitride. The metal oxides in the first doped metal oxide particles and the first undoped metal oxide particles each independently comprise one or more of MoO3, WO3, NiO, CrO3, CuO, and V2O5. The doping element in the first doped metal oxide particles comprises one or more of Mo, W, Ni, Cr, Cu, and V. The metal sulfide comprises one or more of CuS, MoS3, and WS3. The metal selenide comprises one or more of MoSe3 and WSe3. The metal nitride comprises P-type gallium nitride. The doping amount of the doping element in the first doped metal oxide particles is 0.1 wt% to 20 wt%. The optoelectronic device further includes an electronic functional layer located between the light-emitting layer and the anode; the material of the electronic functional layer includes organic N-type semiconductor materials or inorganic N-type semiconductor materials, wherein the organic N-type semiconductor material includes 8-hydroxyquinoline aluminum, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene, 4,7-diphenyl-1,10-o-diazaphenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole, bis(2-methyl-8-hydroxyquinoline-N1,O8)-( One or more of the following: 1,1'-biphenyl-4-hydroxy)aluminum, 2,2'-(1,3-phenyl)bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazole], tris[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane, tetra[(m-pyridyl)-phenyl-3-yl]biphenyl, 3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3',1”-terphenyl]-3,3”-diyl]dipyridine, 1,3-bis(3,5-dipyridin-3-ylphenyl)benzene, n,n′-bis(naphthyl-1-yl)-n,n′-bis(phenyl)benzidine, and diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide. The inorganic N-type semiconductor material includes one or more of the following: second-doped metal oxide particles, second-undoped metal oxide particles, IIB-VIA group semiconductor materials, IIIA-VA group semiconductor materials, IA-VIIA group semiconductor materials, and IB-IIIA-VIA group semiconductor materials. The second-undoped metal oxide particles include one or more of ZnO, TiO2, SnO2, ZrO2, and Ta2O5. The metal oxide in the second-doped metal oxide particles includes one or more of ZnO, TiO2, SnO2, ZrO2, Ta2O5, and Al2O3. The doping elements in the metal oxide particles include one or more of Al, Mg, Li, Mn, Y, La, Cu, Ni, Zr, Ce, In, and Ga; the IIB-VIA group semiconductor materials include one or more of ZnS, ZnSe, and CdS; the IIIA-VA group semiconductor materials include one or more of InP and GaP; the IA-VIIA group semiconductor materials include LiF; and the IB-IIIA-VIA group semiconductor materials include one or more of CuInS and CuGaS. The doping amount of the doping elements in the second doped metal oxide particles is 0.1 wt% to 20 wt%.

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