Compound, light-emitting layer raw material, organic light-emitting device, electronic equipment and preparation method
By using bipolar compounds connected by tetraphenyl silicon groups, carbazole groups and triazine groups as the luminescent layer host material of OLED, the problem of low luminescent efficiency due to existing blue light host materials is solved, and higher luminescent efficiency and stronger lifetime are achieved.
Patent Information
- Application Number
- CN202311184342.9
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2023-09-12
- Publication Date
- 2025-03-14
AI Technical Summary
The existing blue light host materials tend to cause the binding region of holes and electrons to shift, resulting in low luminescence efficiency.
A compound is provided, including a tetraphenyl silicon group, a carbazole group and a triazine group, which are respectively attached to different benzene rings of the tetraphenyl silicon group to form a bipolar compound for use as the luminescent layer host material for OLED.
This compound maintains a wide band gap by interrupting the conjugation within the compound molecule, achieving the transmission balance between holes and electrons, improving luminescence efficiency and extending life.
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Figure CN119613440A_ABST
Abstract
Description
Technical Field
[0001] The present disclosure relates to the field of display technology, and in particular to compounds, light-emitting layer materials, organic light-emitting devices, electronic devices and preparation methods. Background Art
[0002] Organic Light Emitting Diodes (OLED) include a cathode, an organic functional layer and an anode. The organic functional layer includes a light-emitting layer. The light-emitting layer can emit red light, green light and blue light. The raw materials for preparing the light-emitting layer usually include a host material and a guest material to achieve the purpose of improving efficiency and life.
[0003] Since the blue light emission energy level is greater than 2.6eV, which is close to the bond energy of the molecule, it is critical to improve the efficiency and life of the blue light emitting layer. The blue light host material has an important influence on the efficiency and life of the blue light emitting layer. Common blue light host materials in related technologies include mCP, mCBP, oCBP, SiCzCz, mCBP-2CN, TSPO1, PPF, SiTrzCz2, etc.
[0004] However, the above-mentioned blue light host material easily causes the binding area of holes and electrons to shift to the hole transmission side or the electron transmission side, thereby resulting in low luminous efficiency.
[0005] Public Content
[0006] In view of this, the present disclosure provides compounds, light-emitting layer raw materials, organic light-emitting devices, electronic devices and preparation methods, which can solve the technical problems existing in the related technologies.
[0007] Specifically, the following technical solutions are included:
[0008] In one aspect, a compound is provided, the compound comprising a tetraphenylsilane group, a carbazole group and a triazine group, wherein the carbazole group and the triazine group are respectively connected to different benzene rings of the tetraphenylsilane group;
[0009] The triazine group includes a triazine ring and a first aryl substituent and a second aryl substituent attached to the triazine ring.
[0010] The compound provided by the embodiment of the present disclosure uses a tetraphenyl silicon group as the central group of the compound, and the silicon in the tetraphenyl silicon group is SP3 hybridized, and its spatial structure is a regular tetrahedral structure, which can effectively interrupt the conjugation in the compound molecule and is conducive to the compound molecule maintaining a wider band gap. The compound is connected to a carbazole group and a triazine group on different benzene rings of the tetraphenyl silicon group, wherein the carbazole group is electron-rich, which is conducive to hole injection and transmission, and is used as a hole transport group. The triazine group lacks electrons, which is conducive to electron injection and transmission. It can be seen that the compound has both a hole transport group and an electron transport group, so that it has bipolarity, and the bipolar compound can achieve a transmission balance between holes and electrons. When the bipolar compound is used as the main material of the light-emitting layer of an OLED, it is not only conducive to the exciton recombination region being in the center of the light-emitting layer, but also conducive to widening the exciton recombination region. In addition, the triazine group includes a triazine ring and a first aryl substituent and a second aryl substituent connected to the triazine ring, and this type of triazine group structure has the advantages of a higher triplet energy level and stable electron injection energy. The above structural features of the compound enable it to have a higher triplet energy level when used as the main material of the light-emitting layer. On the one hand, this can effectively inject excitons into the guest material and sensitizer and transfer energy, thereby improving the luminescence efficiency. On the other hand, this is conducive to reducing the energy level difference between the triplet state and the singlet state, so that the triplet exciton can be converted into the singlet exciton through reverse intersystem crossing, reducing triplet annihilation, thereby improving the lifespan.
[0011] In some possible implementations, the first aryl substituent and the second aryl substituent are each independently selected from phenyl, dibenzofuranyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, benzanthryl, triphenylenyl, pyrene or dibenzothiophenyl.
[0012] In some possible implementations, the number of the carbazole groups is one or two;
[0013] And / or, the number of the triazine groups is one or two.
[0014] In some possible implementations, the tetraphenylsilicon group, the carbazole group, the first aryl substituent and the second aryl substituent are each substituted or unsubstituted, and for those groups having substituted groups, the substituted groups are each independently selected from alkyl groups, aryl groups, cyano groups, deuterium atoms or halogen atoms.
[0015] In some possible implementations, the chemical structural formula of the compound is as follows:
[0016]
[0017] wherein Ar1 is the first aryl substituent, and Ar2 is the second aryl substituent;
[0018] m and n are each independently selected from integers of 1-5.
[0019] In some possible implementations, the chemical structural formula of the compound is as follows:
[0020]
[0021] wherein the tetraphenylsilicon group, the carbazole group, the phenyl group corresponding to the first aryl substituent, and the phenyl group corresponding to the second aryl substituent are each substituted or unsubstituted;
[0022] X1-X8 are substituent groups, each of which is independently selected from an alkyl group, an aryl group, a cyano group, a deuterium atom or a halogen atom.
[0023] In some possible implementations, the chemical structural formula of the compound is as follows:
[0024]
[0025] wherein the tetraphenylsilane group, the carbazole group, the phenyl group corresponding to the first aryl substituent, and the dibenzofuranyl group corresponding to the second aryl substituent are each substituted or unsubstituted;
[0026] X9-X 15 is a substituent group, and the substituent groups are each independently selected from an alkyl group, an aryl group, a cyano group, a deuterium atom or a halogen atom.
[0027] On the other hand, the embodiment of the present disclosure further provides a light-emitting layer raw material, which includes a host material and a guest material, and the host material is any one of the above compounds.
[0028] The light-emitting layer raw material provided in the embodiment of the present disclosure can be used in an OLED device to form a light-emitting layer, in which the above compound can be used as a main material. The light-emitting layer raw material provided in the embodiment of the present disclosure has all the advantages of the bipolar compound.
[0029] In some possible implementations, the host material is a blue light host material. The compound can be used alone as a blue light host material, or can be used in combination with other host materials to form a blue light host material.
[0030] In some possible implementations, the mass percentage of the host material in the light-emitting layer material is 70%-99%.
[0031] In some possible implementations, the light-emitting layer material further includes a sensitizer, and the mass percentage of the sensitizer in the light-emitting layer material is 5%-30%.
[0032] The light-emitting layer raw material provided in the embodiments of the present disclosure can be used as a blue light-emitting layer raw material, the guest material coordinated with the host material based on the compound can be a fluorescent material, a phosphorescent material or a thermally activated delayed fluorescence (TADF) material, and the sensitizer coordinated with the host material based on the compound can be a phosphorescent material or a TADF material.
[0033] On the other hand, the embodiments of the present disclosure further provide an organic light-emitting device, which includes a cathode, an anode and an organic functional layer, wherein the organic functional layer includes a light-emitting layer and is located between the cathode and the anode; the light-emitting layer is prepared using any of the above-mentioned light-emitting layer raw materials.
[0034] The organic light-emitting device provided in the embodiment of the present disclosure is an organic electroluminescent device (OLED for short), which has all the advantages of the above-mentioned light-emitting layer materials, so that the organic light-emitting device has higher efficiency and longer life.
[0035] In some examples, the organic functional layer includes a light-emitting layer (EML) and a hole transport region and an electron transport region located on both sides of the light-emitting layer, wherein the anode, the hole transport region, the light-emitting layer, the electron transport region and the cathode are stacked in sequence.
[0036] The hole transport region includes at least one of a hole transport layer (HTL), a hole injection layer (HIL), and an electron blocking layer (EBL). The electron transport region includes at least one of an electron transport layer (ETL), an electron injection layer (EIL), and a hole blocking layer (HBL).
[0037] On the other hand, an embodiment of the present disclosure further provides an electronic device, which includes the above-mentioned organic light-emitting device.
[0038] In another aspect, the embodiments of the present disclosure further provide a method for preparing a compound, wherein the compound is as described above;
[0039] The preparation method of the compound comprises: determining the organoboron monomer and the halide monomer used to synthesize the compound according to the chemical structure of the compound;
[0040] The organoboron monomer and the halide monomer are subjected to a coupling reaction to prepare the compound.
[0041] In some possible implementations, the compound is directly synthesized by coupling the organoboron monomer with the halide monomer;
[0042] The organoboron monomer contains a carbazole group and a tetraphenylsilane group, and the halide monomer contains a triazine group;
[0043] The organoboron monomer is prepared by the following method: providing tetraphenylsilane having a carbazole group and a halogen group;
[0044] The tetraphenylsilane having a carbazole group and a halogen group is subjected to a borylation reaction with bis-pinacol diboron to obtain the organoboron monomer.
[0045] In some possible implementations, the precursor of the compound is synthesized by coupling the organoboron monomer with the halide monomer; and the precursor of the compound is grafted with an aromatic substituent to prepare the compound;
[0046] The organoboron monomer contains a carbazole group and a tetraphenylsilane group, and the halide monomer contains a triazine group;
[0047] The organoboron monomer is prepared by the following method: providing tetraphenylsilane having a carbazole group and a halogen group;
[0048] The tetraphenylsilane having a carbazole group and a halogen group is subjected to a borylation reaction with bis-pinacol diboron to obtain the organoboron monomer. BRIEF DESCRIPTION OF THE DRAWINGS
[0049] Figure 1 A schematic diagram of the structure of an exemplary organic light-emitting device provided in an embodiment of the present disclosure;
[0050] Figure 2 A schematic structural diagram of another exemplary organic light-emitting device provided in an embodiment of the present disclosure.
[0051] The reference numerals represent:
[0052] 100, substrate, 200, anode, 300, hole injection layer, 400, hole transport layer, 500, light emitting layer, 600, electron transport layer,
[0053] 700, electron injection layer, 800, cathode, 901, electron blocking layer, 902, hole blocking layer. DETAILED DESCRIPTION
[0054] The following will be combined with the drawings in the embodiments of the present disclosure to clearly and completely describe the technical solutions in the embodiments of the present disclosure. Obviously, the described embodiments are part of the embodiments of the present disclosure, rather than all of the embodiments. Based on the embodiments in the present disclosure, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present disclosure.
[0055] Exemplary embodiments will be described in detail herein, examples of which are shown in the accompanying drawings. When the following description refers to the drawings, the same numbers in different drawings represent the same or similar elements unless otherwise indicated. The embodiments described in the following exemplary embodiments do not represent all embodiments consistent with the present disclosure. Instead, they are merely examples of devices and methods consistent with some aspects of the present disclosure as detailed in the appended claims.
[0056] The light-emitting layer has an important influence on the light-emitting performance of OLED devices. The light-emitting layer includes a red light-emitting layer that emits red light, a green light-emitting layer that emits green light, and a blue light-emitting layer that emits blue light. As the three primary colors of red, green, and blue, the light-emitting energy level of blue is greater than 2.6eV, which is close to the bond energy of molecules. Therefore, it is more critical to improve the efficiency and life of the blue light-emitting layer.
[0057] The raw materials for preparing the blue light-emitting layer include at least a blue light host material and a blue light guest material, and may further include a sensitizer. The content of the blue light host material is relatively high, and it plays an important role in charge transfer, exciton generation, and exciton transfer. Therefore, the blue light host material has an important influence on improving the efficiency and life of the blue light-emitting layer.
[0058] Common blue light host materials in related technologies include mCP, mCBP, oCBP, SiCzCz, mCBP-2CN, TSPO1, PPF, SiTrzCz2, etc. Among them, mCP, mCBP, oCBP, SiCzCz are electron-rich p-type materials, and mCBP-2CN, TSPO1, PPF, SiTrzCz2 are electron-deficient n-type materials. The above blue light host materials all have unipolar characteristics. For n-type materials, since their electron transmission efficiency is higher than that of holes, the binding area of holes and electrons will shift to the hole transmission side. Conversely, for p-type materials, since their electron transmission efficiency is lower than that of holes, the binding area of holes and electrons will shift to the electron transmission side. This shift in the binding area will cause a decrease in luminous efficiency.
[0059] In view of the technical problems existing in the related art, on the one hand, the embodiments of the present disclosure provide a compound, which includes a tetraphenylsilane group, a carbazole group and a triazine group, wherein the carbazole group and the triazine group are respectively connected to different benzene rings of the tetraphenylsilane group. The triazine group includes a triazine ring and a first aryl substituent and a second aryl substituent connected to the triazine ring.
[0060] The compound provided by the embodiment of the present disclosure uses a tetraphenyl silicon group as the central group of the compound, and the silicon in the tetraphenyl silicon group is SP3 hybridized, and its spatial structure is a regular tetrahedral structure, which can effectively interrupt the conjugation in the compound molecule and is conducive to the compound molecule maintaining a wider band gap. The compound is connected to a carbazole group and a triazine group on different benzene rings of the tetraphenyl silicon group, wherein the carbazole group is electron-rich, which is conducive to hole injection and transmission, and is used as a hole transport group. The triazine group lacks electrons, which is conducive to electron injection and transmission. It can be seen that the compound has both a hole transport group and an electron transport group, so that it has bipolarity, and the bipolar compound can achieve a transmission balance between holes and electrons. When the bipolar compound is used as the main material of the light-emitting layer of an OLED, it is not only conducive to the exciton recombination region being in the center of the light-emitting layer, but also conducive to widening the exciton recombination region. In addition, the triazine group includes a triazine ring and a first aryl substituent and a second aryl substituent connected to the triazine ring, and this type of triazine group structure has the advantages of a higher triplet energy level and stable electron injection energy. The above structural features of the compound enable it to have a higher triplet energy level when used as the main material of the light-emitting layer. On the one hand, this can effectively inject excitons into the guest material and sensitizer and transfer energy, thereby improving the luminescence efficiency. On the other hand, this is conducive to reducing the energy level difference between the triplet state and the singlet state, so that the triplet exciton can be converted into the singlet exciton through reverse intersystem crossing, reducing triplet annihilation, thereby improving the lifespan.
[0061] It should be noted that the excitons generated in the light-emitting layer are divided into singlet and triplet states. Singlet excitons can quickly transition back to the ground state to generate light, while triplet excitons transition back to the ground state at a slower rate, causing a large number of triplet excitons in the light-emitting layer to aggregate, triggering the annihilation of triplet excitons, thereby reducing the efficiency and life of the light-emitting layer. The compounds provided in the embodiments of the present disclosure reduce the energy level difference (ΔE) between the singlet energy level and the triplet energy level. st ), so that the triplet excitons are transformed into singlet excitons through reverse intersystem crossing, so as to achieve the purpose of improving the above technical problems.
[0062] In the disclosed embodiments, the carbazole group and the triazine group are respectively connected to different benzene rings of the tetraphenylsilane group. In some examples, one or more carbazole groups are present on one of the benzene rings of the tetraphenylsilane group, and the triazine group is present on another benzene ring of the tetraphenylsilane group. In other words, the carbazole group and the triazine group are connected only on two of the benzene rings of the tetraphenylsilane group.
[0063] The triazine group includes a triazine ring and a first aryl substituent and a second aryl substituent connected to the triazine ring. In some examples, the triazine ring is derived from 1,3,5-s-triazine, which has a higher triplet energy level and stable electron injection energy.
[0064] In some examples, the first aryl substituent and the second aryl substituent in the triazine group are each independently selected from phenyl, dibenzofuranyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, benzanthryl, triphenanthrenyl, pyrenyl, or dibenzothienyl.
[0065] The first aryl substituent and the second aryl substituent may be the same or different, and both are selected from the above-mentioned aryl groups, which has the advantage of further optimizing the electronic structure and improving the stability of the triazine group.
[0066] In some examples, in the compounds provided by the embodiments of the present disclosure, the number of carbazole groups can be 1-5, for example, the number of carbazole groups is one or two, which is conducive to simplifying the preparation process. The carbazole group can replace any substitutable site on the benzene ring where it is located. When the number of carbazole groups is two, the two carbazole groups can replace two different substitutable sites on the same benzene ring.
[0067] In some examples, in the compounds provided by the embodiments of the present disclosure, the number of triazine groups can be 1-5. For example, the number of triazine groups is one or two, which is conducive to simplifying the preparation process. The triazine groups can replace any substitutable sites on the benzene ring where they are located. When the number of triazine groups is two, the two triazine groups can replace two different substitutable sites on the same benzene ring.
[0068] In some implementations, in the compounds provided by the embodiments of the present disclosure, the tetraphenylsilicon group, the carbazole group, the first aryl substituent and the second aryl substituent are each substituted or unsubstituted, and for those groups having substituted groups, the substituted groups are each independently selected from alkyl groups, aryl groups, cyano groups, deuterium atoms or halogen atoms.
[0069] For example, alkyl includes but is not limited to methyl, isopropyl, tert-butyl, adamantyl, etc. Aryl includes but is not limited to phenyl, naphthyl, anthracenyl, phenanthrenyl, benzanthryl, triphenylenyl, pyrenyl, etc. The halogen atom can be a fluorine atom, a chlorine atom, a bromine atom, etc. For example, the halogen atom is a fluorine atom.
[0070] In combination with the above description of the compound, in some implementations, the chemical structure of the compound is as follows:
[0071]
[0072] Wherein, Ar1 is the first aryl substituent, Ar2 is the second aryl substituent; m and n are each independently selected from an integer of 1-5.
[0073] Illustratively, the first aryl substituent and the second aryl substituent are each independently selected from phenyl, dibenzofuranyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, benzanthryl, triphenylenyl, pyrenyl, or dibenzothienyl.
[0074] For example, m and n are each independently 1 or 2.
[0075] In combination with the above chemical structural formula of the compound, as an example, the chemical structural formula of the compound is further shown as follows:
[0076]
[0077] Wherein, in the compound, the tetraphenylsilicon group, the carbazole group, the phenyl group corresponding to the first aryl substituent, and the phenyl group corresponding to the second aryl substituent are each substituted or unsubstituted.
[0078] For those groups having a substituent, X1 to X8 are substituents, and these substituents are each independently selected from an alkyl group, an aryl group, a cyano group, a deuterium atom or a halogen atom.
[0079] In some examples, the number of X1-X8 is independently 1 or more. For example, if the replacement point allows, the number can also be 2, 3, 4, 5, etc.
[0080] The compound having the above chemical structural formula is particularly suitable as a blue light host material, and has the effect of effectively improving the efficiency and life of the blue light emitting layer.
[0081] In combination with the above chemical structural formula of the compound, as another example, the chemical structural formula of the compound is further shown as follows:
[0082]
[0083] In the compound, the tetraphenylsilane group, the carbazole group, the phenyl group corresponding to the first aryl substituent, and the dibenzofuranyl group corresponding to the second aryl substituent are each substituted or unsubstituted.
[0084] For those groups having substituent groups, X9-X 15 Each is independently a substituent group, and the substituent group is independently selected from an alkyl group, an aryl group, a cyano group, a deuterium atom or a halogen atom.
[0085] In some examples, X9-X 15 The number of each independently is 1 or more, for example, when the substitution point allows, the number can also be 2, 3, 4, 5, etc.
[0086] The compound having the above chemical structural formula is particularly suitable as a blue light host material, and has the effect of effectively improving the efficiency and life of the blue light emitting layer.
[0087] According to another aspect of the embodiments of the present disclosure, a light-emitting layer raw material is provided. The light-emitting layer raw material includes a host material and a guest material. The host material is any one of the compounds described above in the embodiments of the present disclosure.
[0088] The light-emitting layer raw material provided in the embodiment of the present disclosure can be used in an OLED device to form a light-emitting layer, in which the above compound can be used as a main material. The light-emitting layer raw material provided in the embodiment of the present disclosure has all the advantages of the bipolar compound.
[0089] In some examples, the compound provided by the embodiments of the present disclosure is used as a blue light host material in the raw materials of the light-emitting layer. The compound can be used alone as a blue light host material, or it can be combined with other host materials to form a blue light host material.
[0090] In some examples, the mass percentage of the main material in the light-emitting layer material is 70%-99%, and can further be 80%-95%, including but not limited to: 70%, 73%, 75%, 77%, 78%, 79%, 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%.
[0091] In some examples, the light-emitting layer material is a binary material system, in which case the mass percentage of the guest material is the remainder.
[0092] In other examples, the light-emitting layer raw material also includes a sensitizer, that is, the light-emitting layer material can be a ternary material system, which includes a main material, a guest material and a sensitizer at the same time, and the mass percentage of the sensitizer in the light-emitting layer material is 5%-30%, and can further be 5%-20%, which includes but is not limited to: 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 25%, 27%, 30%, etc.
[0093] The light-emitting layer raw material provided in the embodiments of the present disclosure can be used as a blue light-emitting layer raw material, the guest material coordinated with the host material based on the compound can be a fluorescent material, a phosphorescent material or a thermally activated delayed fluorescence (TADF) material, and the sensitizer coordinated with the host material based on the compound can be a phosphorescent material or a TADF material.
[0094] TADF materials have the characteristic of a small energy level difference between singlet and triplet states, which enables them to utilize the antisystem crossing process to convert triplet excitons into singlet excitons and undergo radiative transition emission. The advantage is that the utilization of triplet excitons can be achieved without the introduction of heavy metals, achieving a maximum exciton utilization rate of 100%.
[0095] For the guest material, some applicable blue fluorescent materials include but are not limited to Perylene, TBPe, TBPDP, MADN, etc.; some applicable blue phosphorescent materials include but are not limited to FIrppy, FIrpic, FIr6, (CF3ppy)2Ir(pic), FIrtaz, PtON-7-dtb, PTON-TBBI, etc.; some applicable blue TADF materials include but are not limited to SpiroAC-TRZ, BCz-TRz, 2CzPN, DMAC-TRZ, DABANA-1, t-DABANA, v-DABANA, etc.
[0096] For sensitizers, some applicable phosphorescent sensitizers include but are not limited to Ir(dpbic)3, Ir(cb)3, Ir(ppy)2acac, CN-Ir, PtON7-dtb, PtON-TBBI, etc.; some applicable TADF type sensitizers include but are not limited to TPh2Cz2DPhCzBN, PCzTrz, PPCzTrz, etc.
[0097] According to another aspect of the embodiments of the present disclosure, an organic light-emitting device is provided, which includes a cathode, an anode and an organic functional layer, wherein the organic functional layer includes a light-emitting layer and is located between the cathode and the anode; the light-emitting layer is prepared using any of the light-emitting layer raw materials mentioned above.
[0098] The organic light-emitting device provided in the embodiment of the present disclosure is an organic electroluminescent device (OLED for short), which has all the advantages of the above-mentioned light-emitting layer materials, so that the organic light-emitting device has higher efficiency and longer life.
[0099] In some examples, the organic functional layer includes a light-emitting layer (EML) and a hole transport region and an electron transport region located on both sides of the light-emitting layer, wherein the anode, the hole transport region, the light-emitting layer, the electron transport region and the cathode are stacked in sequence.
[0100] The hole transport region includes at least one of a hole transport layer (HTL), a hole injection layer (HIL), and an electron blocking layer (EBL). The electron transport region includes at least one of an electron transport layer (ETL), an electron injection layer (EIL), and a hole blocking layer (HBL).
[0101] See also Figure 1An exemplary structural arrangement of an organic light-emitting device is as follows: the organic light-emitting device includes a substrate 100, an anode 200, a hole injection layer 300, a hole transport layer 400, a light-emitting layer 500, an electron transport layer 600, an electron injection layer 700 and a cathode 800 which are stacked in sequence.
[0102] See also Figure 2 Another exemplary structural arrangement of the organic light-emitting device is: the organic light-emitting device includes a substrate 100, an anode 200, a hole injection layer 300, a hole transport layer 400, an electron blocking layer 901, a light-emitting layer 500, a hole blocking layer 902, an electron transport layer 600, an electron injection layer 700 and a cathode 800 arranged in sequence.
[0103] In addition, the organic light-emitting device provided in the embodiment of the present disclosure may be partially encapsulated, fully encapsulated, or unencapsulated, and the organic light-emitting device may be top-emitting or bottom-emitting.
[0104] The anode is usually formed on a substrate, which can be a rigid substrate or a flexible substrate. The rigid substrate includes but is not limited to one or more of glass, ceramic, and metal foil; the flexible substrate includes but is not limited to polyethylene terephthalate (PET), polyethylene terephthalate (PEN), polyetheretherketone (PEEK), polyimide (PI), etc.
[0105] For the anode, hole injection layer, hole transport layer, electron blocking layer, electron transport layer, electron injection layer, hole blocking layer and cathode, they can each use materials commonly used in the art, thereby synergizing with the light-emitting layer to achieve the purpose of improving the efficiency and life of the organic light-emitting device.
[0106] According to another aspect of the embodiments of the present disclosure, the embodiments of the present disclosure further provide an electronic device, which includes any one of the above-mentioned organic light-emitting devices and has all the advantages of the organic light-emitting device.
[0107] In some examples, the organic light-emitting device provided by the embodiments of the present disclosure can be used to prepare display screens of electronic devices, including but not limited to: mobile phones, computers, tablet computers, televisions, telephones, virtual reality or augmented reality displays, car displays, etc.
[0108] According to another aspect of the embodiments of the present disclosure, a method for preparing a compound is also provided, wherein the compound is as described above. The method for preparing the compound comprises: determining an organoboron monomer and a halide monomer for synthesizing the compound according to the chemical structure of the compound; and subjecting the organoboron monomer and the halide monomer to a coupling reaction to prepare the compound.
[0109] The disclosed embodiments determine the organoboron monomer and the halide monomer used to synthesize the compound based on the chemical structure of the compound, so that the compound can be prepared by connecting the monomers based on a coupling reaction.
[0110] In some implementations, the compound is directly synthesized by coupling an organoboron monomer with a halide monomer. In this implementation, the organoboron monomer contains a carbazole group and a tetraphenylsilane group, and the halide monomer contains a triazine group; then, the organoboron monomer is prepared by the following method: providing a tetraphenylsilane having a carbazole group and a halogen group; and subjecting the tetraphenylsilane having a carbazole group and a halogen group to a borylation reaction with a bis-pinacol-based diboron to obtain an organoboron monomer.
[0111] The tetraphenylsilane having a carbazole group and a halogen group can be directly prepared from a ready-made compound product or can be obtained by self-production. For example, the tetraphenylsilane having a carbazole group and a halogen group is prepared by the following method: a silane monomer containing a halogen group and a carbazole monomer containing a halogen group are subjected to a coupling reaction to prepare the tetraphenylsilane having a carbazole group and a halogen group.
[0112] Among them, the reaction conditions (including reaction temperature, reaction time, solvent, etc.) and catalytic environment and other parameters of the coupling reaction and borylation reaction involved above can be adaptively determined according to the actual substances to be synthesized and related raw materials to ensure that the coupling reaction and borylation reaction can be carried out smoothly.
[0113] As an example (1), a compound 1 is provided, and the chemical structure of the compound 1 is shown below:
[0114]
[0115] In combination with the following preparation formula of compound 1, the preparation method of compound 1 comprises the following steps:
[0116] Step S11, a halogen-containing silane monomer and a halogen-containing carbazole monomer are subjected to a coupling reaction to prepare tetraphenylsilane having a carbazole group and a halogen group.
[0117] Step S12, subjecting tetraphenylsilane having a carbazole group and a halogen group to a borylation reaction with bis-pinacol diboron to prepare an organic boron monomer.
[0118] Step S13, coupling reaction of the organoboron monomer and the halide monomer to prepare compound 1.
[0119] The preparation formula of compound 1 is shown below:
[0120]
[0121]
[0122] In other implementations, the precursor of the compound is synthesized by coupling an organoboron monomer with a halide monomer; further, the precursor of the compound is grafted with an aromatic substituent to prepare the compound.
[0123] In this implementation, the organic boron monomer contains a carbazole group and a tetraphenylsilane group, and the halide monomer contains a triazine group; then, the organic boron monomer is prepared by the following method: providing tetraphenylsilane having a carbazole group and a halogen group; allowing the tetraphenylsilane having a carbazole group and a halogen group to undergo a borylation reaction with bipinacol-based diboron to obtain an organic boron monomer.
[0124] This method is suitable for grafting at least one of the first and second aromatic groups with relatively complex structures into the precursor of the compound, wherein the grafting process can be completed by coupling the organic boron monomer containing the target aromatic substituent with the precursor of the compound.
[0125] The tetraphenylsilane having a carbazole group and a halogen group can be directly prepared from a ready-made compound product or can be prepared by self-production. For example, the tetraphenylsilane having a carbazole group and a halogen group can be prepared by the following method: a silane monomer containing a halogen group and a carbazole monomer containing a halogen group are subjected to a coupling reaction to prepare a tetraphenylsilane precursor having a carbazole group and a halogen group. An aromatic group containing a halogen substituent is grafted onto the tetraphenylsilane precursor to prepare a tetraphenylsilane having a carbazole group and a halogen group.
[0126] For the organoboron monomer containing the target aromatic substituent, the ready-made compound product can be directly used, or it can be obtained by self-production. For example, the organoboron monomer containing the target aromatic substituent can be prepared by the following method: providing a target aromatic compound, and subjecting the target aromatic compound to borylation reaction with bis-pinacol diboron to obtain an organoboron monomer containing the target aromatic substituent. The target aromatic compound is used to provide the above-mentioned target aromatic substituent. The target aromatic compound can be directly used as a ready-made compound product, or it can be obtained by self-production. For example, a coupling reaction can be used to graft a substituent on a precursor compound of the target aromatic compound to synthesize the target aromatic compound.
[0127] As an example (2), a compound 2 is provided, and the chemical structure of the compound 2 is shown below:
[0128]
[0129] In combination with the following preparation formula of compound 2, the preparation method of compound 2 comprises the following steps:
[0130] Step S21, coupling reaction of silane monomer containing halogen group and carbazole monomer containing halogen group to prepare tetraphenylsilane precursor having carbazole group and halogen group. Grafting aryl group containing halogen substituent on tetraphenylsilane precursor to prepare tetraphenylsilane having carbazole group and halogen group.
[0131] Step S22, subjecting tetraphenylsilane having a carbazole group and a halogen group to a borylation reaction with bis-pinacol diboron to prepare an organic boron monomer.
[0132] Step S23, coupling reaction of the organoboron monomer and the halide monomer to prepare a precursor of compound 2.
[0133] Step S24, grafting an aryl substituent onto the precursor of compound 2 to prepare compound 2, which includes: coupling an organic boron monomer containing a target aryl substituent with the precursor of compound 2. In compound 2, the target aryl substituent is a cyano-substituted dibenzofuran group.
[0134] Among them, for the organoboron monomer containing the target aromatic substituent, referring to step S240, it can be prepared by the following method: using a coupling reaction, grafting a substituent on a precursor compound of the target aromatic compound to synthesize the target aromatic compound. The target aromatic compound is subjected to a borylation reaction with bis-pinacol diboron to obtain an organoboron monomer containing the target aromatic substituent.
[0135] The preparation formula of compound 2 is shown below:
[0136]
[0137]
[0138] The specific embodiments of the present invention will be described in more detail below. Although the specific embodiments of the present invention are described below, it should be understood that the present invention can be implemented in various forms and should not be limited by the embodiments set forth herein. The specific techniques or conditions not specified in the examples are carried out according to the techniques or conditions described in the documents in this area or according to the product specification. The reagents, materials or instruments used are not specified by the manufacturer and are all conventional products that can be obtained commercially.
[0139] Example 1
[0140] In this Example 1, the above-mentioned compound 1 was prepared. Combined with the preparation formula of the above-mentioned compound 1, the preparation steps of the compound 1 are as follows:
[0141] (1) Synthesis of tetraphenylsilane containing carbazole group and bromine group, see step S11, which includes: Under nitrogen protection, 9,9'-(5-bromo-1,3-phenylene)bis(9H-carbazole) (30.0 g, 62 mmol) is dissolved in 300 mL of anhydrous tetrahydrofuran. nBuLi (70 mmol) is slowly added at a temperature of -78°C and stirred for 1 hour. The obtained reaction solution is added to a 300 mL tetrahydrofuran solution containing p-bromophenyldiphenylchlorosilane (24 g, 65 mmol, CAS No.: 18557-79-4), and slowly heated to room temperature. The reaction is allowed to react overnight to synthesize tetraphenylsilane containing carbazole group and bromine group.
[0142] The hydrogen nuclear magnetic resonance test results of the tetraphenylsilane containing carbazole groups and bromine groups are as follows: 1 HNMR (500MHz, CDCl3): δ (ppm) 8.15 (d, 2H), 7.85 (d, 2H), 7.70 (dd, 4H), 7.59 (d, 2H), 7.45~7.30 (m, 16H), 7.25 (d, 2H), 7.15 (s, 1H).
[0143] (2) Synthesizing an organic boron monomer, see step S12, which includes: dissolving the above-synthesized tetraphenylsilane containing carbazole group and bromine group (15.0 g, 20 mmol) in 200 mL of tetrahydrofuran under a nitrogen atmosphere. Slowly adding nBuLi (30 mmol) at a temperature of -78°C, stirring for 1 hour. Then slowly adding bis(pinacol)diboron (7.5 g, 30 mmol) to the reaction system, heating the reaction system to room temperature, reacting overnight, and synthesizing an organic boron monomer.
[0144] The hydrogen nuclear magnetic resonance test results of the organic boron monomer are as follows: 1 HNMR (500MHz, CDCl3): δ (ppm) 8.15 (d, 2H), 7.83 (d, 2H), 7.70 (dd, 4H), 7.59 (d, 2H), 7.45~7.30 (m, 16H), 7.25 (d, 2H), 7.15 (s, 1H), 1.30 (s, 12H).
[0145] (3) Synthesizing compound 1, see step S13, which includes: under a nitrogen atmosphere, dissolving the above-synthesized organic boron monomer (6.4 g, 8 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.6 g, 10 mmol), tetrakis(triphenylphosphine)palladium (0.50 g, 0.4 mmol), 15 mL of 2 mol / L K2CO3 solution, and 15 mL of ethanol in 60 mL of toluene, reacting at reflux temperature for 20 hours to synthesize compound 1. The chemical structure of compound 1 is consistent with the chemical structure shown in the embodiment of the present disclosure as tested by hydrogen nuclear magnetic resonance.
[0146] This Example 1 also tested the energy level of Compound 1 based on the principles of quantum chemistry. The test results are shown in Table 1:
[0147] Table 1
[0148] project HOMO LUMO Band Gap T1 S1 <![CDATA[△E ST ]]> Compound 1 -5.55eV -2.18eV 3.37eV 2.96eV 3.05eV 0.09eV
[0149] In Table 1, HOMO energy level refers to the energy level corresponding to the highest occupied molecular orbital (Highest Occupied Molecular Orbital). LUMO energy level refers to the energy level corresponding to the lowest unoccupied molecular orbital (Lowest Unoccupied Molecular Orbital).
[0150] Bandgap refers to the energy difference between the HOMO energy level and the LUMO energy level; T1 is the triplet energy level, S1 is the singlet energy level, △E ST It is the energy difference between the singlet energy level S1 and the triplet energy level T1.
[0151] As can be seen from Table 1, compound 1 has a higher triplet energy level, which makes the energy range difference between the singlet energy level S1 and the triplet energy level T1 lower. The lower energy range difference can effectively drive the triplet excitons to efficiently transform into singlet excitons, thereby allowing the host material based on compound 1 to effectively transfer energy to the guest material or sensitizer.
[0152] Example 1 also tested the stability of compound 1 and the currently known blue light host material mCBP, wherein the chemical structure of the blue light host material mCBP is as follows:
[0153]
[0154] On the one hand, the bond energy between the carbazole group and the connected benzene ring of compound 1 and compound mCBP was tested. Specifically, the relevant bond energy data of compound 1 and compound mCBP under neutral conditions, cationic conditions, and anionic conditions were obtained. The test results are shown in Table 2:
[0155] Table 2
[0156] project neutral condition Cationic conditions Anionic conditions mCBP 3.90eV 4.73eV 2.09eV Compound 1 3.93eV 5.08eV 3.05eV
[0157] As can be seen from Table 2, the molecular bond energy of Compound 1 of Example 1 of the present disclosure is higher than that of mCBP under different conditions, which indicates that Compound 1 is more stable than mCBP, giving it a stronger lifespan.
[0158] On the other hand, the hole and electron transport capabilities of compound 1 and compound mCBP were tested. The test results are shown in Table 3:
[0159] Table 3
[0160] project <![CDATA[λ h ]]> <![CDATA[λ e ]]> <![CDATA[λ h / l e ]]> mCBP 0.047eV 0.482eV 0.098 Compound 1 0.179eV 0.471eV 0.380
[0161] Among them, λ h is the molecular reformation energy of the hole, λ e is the molecular reformation energy of electrons. These two data can reflect the hole and electron transport capabilities of compound molecules. h and λ e The smaller the value of is, the higher the corresponding transmission capacity is, and h / λ e The closer the value is to 1, the more balanced the transport capabilities of holes and electrons are.
[0162] As can be seen from Table 3, the hole and electron transport balance of Compound 1 of Example 1 of the present disclosure is stronger than that of mCBP, which makes it have higher efficiency and lifespan.
[0163] Example 2
[0164] In this Example 2, the above-mentioned compound 2 was prepared. Combined with the preparation formula of the above-mentioned compound 2, the preparation steps of the compound 2 are as follows:
[0165] (1) Synthesizing tetraphenylsilane containing carbazole groups and bromine groups, see step S21, which includes: dissolving 9-(4-bromophenyl)carbazole (30.0 g, 93 mmol) in 300 mL of anhydrous tetrahydrofuran under nitrogen protection. Slowly adding nBuLi (93 mmol) at a temperature of -78°C, stirring for 1 hour. Adding the obtained reaction solution to a 300 mL tetrahydrofuran solution containing dichlorodiphenylsilane (30 g, 120 mmol) and slowly heating to room temperature, reacting overnight, synthesizing a tetraphenylsilane precursor containing carbazole groups and bromine groups.
[0166] The hydrogen nuclear magnetic resonance test results of the tetraphenylsilane precursor are as follows: 1HNMR (500MHz, CDCl3): δ (ppm) 8.13 (d, 2H), 7.85 (d, 2H), 7.70 (dd, 4H), 7.59 (d, 2H), 7.48~7.37 (m, 8H), 7.28 (d, 2H), 7.25 (d, 2H).
[0167] Under nitrogen protection, 1,3-dibromobenzene (15.0 g, 60 mmol) was dissolved in 150 mL of anhydrous tetrahydrofuran. After slowly adding nBuLi (75 mmol) at -78°C, the mixture was stirred for 1 hour. The reaction solution was then added to a tetrahydrofuran solution containing a tetraphenylsilane precursor (30 g, 120 mmol), slowly heated to room temperature, and reacted overnight to synthesize tetraphenylsilane containing a carbazole group and a bromine group.
[0168] The hydrogen nuclear magnetic resonance test results of the tetraphenylsilane containing carbazole groups and bromine groups are as follows: 1 HNMR (500MHz, CDCl3): δ (ppm) 8.12 (d, 2H), 7.80-7.76 (m, 3H), 7.65-7.58 (m, 7H), 7.55 (d, 1H), 7.50-7.38 (m, 10H), 7.31-7.26 (dd, 3H). It can be seen that the chemical structure of the synthesized tetraphenylsilane conforms to the chemical structure described in step S21.
[0169] (2) Synthesizing an organic boron monomer, see step S22, which includes: dissolving the synthesized tetraphenylsilane (14.0 g, 24 mmol) in 200 mL of tetrahydrofuran under nitrogen protection. Slowly adding nBuLi (30 mmol) at -78°C and stirring for 1 hour. Then slowly adding bis(pinacolato)diboron (7.5 g, 30 mmol), heating the reaction system to room temperature, and leaving overnight to synthesize an organic boron monomer.
[0170] The hydrogen nuclear magnetic resonance test results of the organic boron monomer are as follows: 1 HNMR (500MHz, CDCl3): δ (ppm) 8.13 (d, 2H), 7.90 (d, 1H), 7.79 (d, 2H), 7.70 (d, 1H), 7.68 (d d, 3H), 7.64 (dd, 2H), 7.58 (dd, 2H), 7.49~7.37 (m, 10H), 7.28~7.24 (dd, 3H), 1.30 (s, 12H).
[0171] (3) Synthesizing the precursor of compound 2, see step S23, which includes: under a nitrogen protection environment, dissolving 2,4-dichloro-6-phenyl-1,3,5-triazine (4.5 g, 20 mmol), the above-mentioned organic boron monomer (9.4 g, 15 mmol), tetrakis(triphenylphosphine)palladium (0.70 g, 0.6 mmol), 20 mL of 2 mol / L K2CO3 solution, and 20 mL of ethanol in 80 mL of toluene, and reacting at reflux temperature for 20 hours to synthesize the precursor of compound 2.
[0172] The hydrogen nuclear magnetic resonance test results of the precursor of compound 2 are as follows: 1 HNMR (500MHz, CDCl3): δ (ppm) 9.08 (s, 1H), 8.75 (d, 1H), 8.51 (d, 1H), 8.14 (d, 2H), 7.90 (m, 3H), 7.7 5~7.64 (dd, 4H), 7.58 (dd, 2H), 7.52 (d, 1H), 7.50-7.46 (m, 10H), 7.38~7.34 (dd, 5H), 7.26 (dd, 4H).
[0173] (4) Synthesizing compound 2, see step S24, which includes: under nitrogen protection, dissolving the precursor of compound 2 (6.9 g, 10 mmol), an organic boron monomer containing a cyano-substituted dibenzofuran group (No. 1638836-99-3) (3.2 g, 10 mmol), tetrakis(triphenylphosphine)palladium (0.50 g, 0.4 mmol), 15 mL of 2 mol / L K2CO3 solution, and 15 mL of ethanol in 60 mL of toluene, reacting at reflux temperature for 20 hours to synthesize compound 2. The chemical structure of compound 2 is consistent with the chemical structure shown in the embodiment of the present disclosure as tested by hydrogen nuclear magnetic resonance.
[0174] This Example 2 also tests the energy level of compound 2 based on the principle of quantum chemistry. The test results are shown in Table 4:
[0175] Table 4
[0176] project HOMO LUMO Band Gap T1 S1 <![CDATA[△E ST ]]> Compound 2 -5.54eV -2.18eV 3.33eV 2.92eV 2.98eV 0.06eV
[0177] As can be seen from Table 4, compound 2 has a higher triplet energy level, which makes the energy range difference between the singlet energy level S1 and the triplet energy level T1 lower. The lower energy range difference can effectively drive the triplet excitons to efficiently transform into singlet excitons, thereby allowing the main material based on compound 2 to effectively transfer energy to the guest material or sensitizer.
[0178] Example 2 also tested the stability of compound 2 and the currently known blue light host material mCBP. On the one hand, the bond energy between the carbazole group and the connected benzene ring of compound 2 and compound mCBP was tested. Specifically, the relevant bond energy data of compound 2 and compound mCBP under neutral conditions, cationic conditions, and anionic conditions were tested. The test results are shown in Table 5:
[0179] Table 5
[0180] project neutral condition Cationic conditions Anionic conditions mCBP 3.90eV 4.73eV 2.09eV Compound 2 4.30eV 5.07eV 3.19eV
[0181] As can be seen from Table 5, the molecular bond energy of Compound 2 of Example 2 of the present disclosure is higher than that of mCBP under different conditions, which indicates that the stability of Compound 2 is higher than that of mCBP, giving it a stronger lifespan.
[0182] On the other hand, the hole and electron transport capabilities of compound 2 and compound mCBP were tested. The test results are shown in Table 6:
[0183] Table 6
[0184] project <![CDATA[λ h ]]> <![CDATA[λ e ]]> <![CDATA[λ h / l e ]]> mCBP 0.047eV 0.482eV 0.098 Compound 2 0.170eV 0.277eV 0.614
[0185] Among them, λ h is the molecular reformation energy of the hole, λ e is the molecular reformation energy of electrons. These two data can reflect the hole and electron transport capabilities of compound molecules. h and λ e The smaller the value of is, the higher the corresponding transmission capacity is, and h / λ e The closer the value is to 1, the more balanced the transport capabilities of holes and electrons are.
[0186] As can be seen from Table 6, the hole and electron transport balance of Compound 2 of Example 2 of the present disclosure is stronger than that of mCBP, which makes it have higher efficiency and lifespan.
[0187] Example 3
[0188] In this Example 3, Compound 1 of Example 1 and Compound 2 of Example 2 were used as test examples, and Compound mCBP was used as a comparative example, and the applications of the three in OLED devices were tested respectively.
[0189] Specifically, the compound 1 (host material) of Example 1 of the present disclosure and the blue phosphorescent material PtON-7-dtb (guest material) are mixed in a mass ratio of 4:1 to form a light-emitting layer raw material to prepare the light-emitting layer, and an OLED device 1 is prepared based on the light-emitting layer.
[0190] The compound 2 (host material) of Example 2 of the present disclosure is mixed with the blue phosphorescent material PtON-7-dtb (guest material) at a mass ratio of 4:1 to form a light-emitting layer raw material to prepare a light-emitting layer, and an OLED device 2 is prepared based on the light-emitting layer.
[0191] mCBP was used as a host material and mixed with a blue phosphorescent material PtON-7-dtb (guest material) at a mass ratio of 4:1 to form a light-emitting layer raw material to prepare a light-emitting layer comparative example, and an OLED device comparative example was prepared based on the light-emitting layer comparative example.
[0192] The only difference between OLED device 1, OLED device 2 and OLED device comparison is the light-emitting layer, and the other layers are completely the same, and the other layers are all made of currently known materials. In addition, the test conditions for OLED device 1, OLED device 2 and OLED device comparison are all the same.
[0193] The test conditions and test results of the OLED device comparison are used as the reference conditions. Specifically, the operating voltage of the OLED device comparison is set as the reference voltage, and the current luminous efficiency of the OLED device comparison is set as the reference luminous efficiency. One set of data obtained from the test is that the operating voltage of OLED device 1 is 0.84 times the reference voltage, and the current luminous efficiency of OLED device 1 is 1.2 times the reference luminous efficiency. The operating voltage of OLED device 2 is 0.75 times the reference voltage, and the current luminous efficiency of OLED device 2 is 1.3 times the reference luminous efficiency.
[0194] It can be seen that compared with the comparative example of OLED devices, the OLED devices 1 and 2 obtain higher current luminous efficiency at a lower operating voltage. Therefore, compared with the currently known compound mCBP, the compounds 1 and 2 provided in the embodiments of the present disclosure are particularly advantageous for improving the device luminous efficiency and reducing the device energy consumption.
[0195] It should be noted that the chemical structure of the above-mentioned blue phosphorescent material PtON-7-dtb is as follows:
[0196]
[0197] The above description is only for the purpose of facilitating those skilled in the art to understand the technical solution of the present disclosure and is not intended to limit the present disclosure. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present disclosure shall be included in the protection scope of the present disclosure.
Claims
1. A compound, characterized in that The compound comprises a tetraphenylsilicon group, a carbazole group and a triazine group, wherein the carbazole group and the triazine group are respectively connected to different benzene rings of the tetraphenylsilicon group; The triazine group includes a triazine ring and a first aryl substituent and a second aryl substituent attached to the triazine ring.
2. The compound according to claim 1, characterized in that The first aryl substituent and the second aryl substituent are each independently selected from phenyl, dibenzofuranyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, benzanthryl, triphenylenyl, pyrenyl or dibenzothienyl.
3. The compound according to claim 1, characterized in that The number of the carbazole groups is one or two; And / or, the number of the triazine groups is one or two.
4. The compound according to claim 1, characterized in that The tetraphenylsilicon group, the carbazole group, the first aryl substituent and the second aryl substituent are each substituted or unsubstituted, and for those groups having a substituent, the substituent is each independently selected from an alkyl group, an aryl group, a cyano group, a deuterium atom or a halogen atom.
5. The compound according to any one of claims 1 to 4, characterized in that The chemical structural formula of the compound is shown below: wherein Ar1 is the first aryl substituent, and Ar2 is the second aryl substituent; m and n are each independently selected from integers of 1-5.
6. The compound according to claim 5, characterized in that The chemical structural formula of the compound is shown below: wherein the tetraphenylsilicon group, the carbazole group, the phenyl group corresponding to the first aryl substituent, and the phenyl group corresponding to the second aryl substituent are each substituted or unsubstituted; X1-X8 are substituent groups, each of which is independently selected from an alkyl group, an aryl group, a cyano group, a deuterium atom or a halogen atom.
7. The compound according to claim 5, characterized in that The chemical structural formula of the compound is shown below: wherein the tetraphenylsilane group, the carbazole group, the phenyl group corresponding to the first aryl substituent, and the dibenzofuranyl group corresponding to the second aryl substituent are each substituted or unsubstituted; X9-X 15 is a substituent group, and the substituent groups are each independently selected from an alkyl group, an aryl group, a cyano group, a deuterium atom or a halogen atom.
8. A light-emitting layer raw material, characterized in that: The raw materials of the light-emitting layer include a host material and a guest material, and the host material is a compound according to any one of claims 1 to 7.
9. The light-emitting layer raw material according to claim 8, characterized in that The host material is a blue light host material.
10. The light-emitting layer raw material according to claim 8 or 9, characterized in that: The mass percentage of the main material in the light-emitting layer material is 70%-99%.
11. The luminescent layer raw material according to any one of claims 8 to 10, characterized in that: The luminescent layer raw material also includes a sensitizer, and the mass percentage of the sensitizer in the luminescent layer material is 5%-30%.
12. An organic light-emitting device, characterized in that: The organic light emitting device comprises a cathode, an anode and an organic functional layer, wherein the organic functional layer comprises a light emitting layer and is located between the cathode and the anode; The light-emitting layer is prepared by using the light-emitting layer raw material according to any one of claims 8 to 11.
13. An electronic device, characterized in that: The electronic device comprises the organic light emitting device according to claim 12.
14. A method for preparing a compound, characterized in that: The compound is as described in any one of claims 1 to 7; The preparation method of the compound comprises: According to the chemical structure of the compound, determining the organoboron monomer and the halide monomer used to synthesize the compound; The organoboron monomer and the halide monomer are subjected to a coupling reaction to prepare the compound.
15. The method for preparing the compound according to claim 14, characterized in that: The compound is directly synthesized by coupling the organoboron monomer with the halide monomer; The organoboron monomer contains a carbazole group and a tetraphenylsilane group, and the halide monomer contains a triazine group; The organoboron monomer is prepared by the following method: providing tetraphenylsilane having a carbazole group and a halogen group; The tetraphenylsilane having a carbazole group and a halogen group is subjected to a borylation reaction with bis-pinacol diboron to obtain the organoboron monomer.
16. The method for preparing the compound according to claim 14, characterized in that: The precursor of the compound is synthesized by coupling the organoboron monomer with the halide monomer; and the precursor of the compound is grafted with an aromatic substituent to prepare the compound; The organoboron monomer contains a carbazole group and a tetraphenylsilane group, and the halide monomer contains a triazine group; The organoboron monomer is prepared by the following method: providing tetraphenylsilane having a carbazole group and a halogen group; The tetraphenylsilane having a carbazole group and a halogen group is subjected to a borylation reaction with bis-pinacol diboron to obtain the organoboron monomer.