WO2021135517A1

WO2021135517A1 - Organic compound, electronic component and electronic device

Info

Publication number: WO2021135517A1
Application number: PCT/CN2020/121976
Authority: WO
Inventors: 张孔燕; 马天天; 曹佳梅
Original assignee: 陕西莱特光电材料股份有限公司
Priority date: 2019-12-30
Filing date: 2020-10-19
Publication date: 2021-07-08
Also published as: CN111646951B; KR102444216B1; CN111646951A; KR20220052372A

Abstract

The present application belongs to the technical field of organic materials, and specifically provided therein is an organic compound. The compound is a structure composed by using an adamantyl group as the core and by linking two nitrogen-containing heteroaryl groups to adamantane by using linking groups. The compound of the present application is suitable to be applied to an electron transport layer of an electronic component. Further provided in the present application are an electronic component and electronic device comprising the described compound, and the organic compound can improve the electron transport performance of the electronic component.

Description

Organic compounds, electronic components and electronic devices

Cross-references to related applications

The present invention claims the priority of the Chinese patent application filed on December 30, 2019 with the application number CN201911402100.6, and the full content of the above-mentioned Chinese patent application is cited here as a part of this application. The present invention claims the priority of the Chinese patent application filed on July 3, 2020 with the application number CN202010637261.X, and the full content of the Chinese patent application disclosed above is cited here as a part of this application.

Technical field

This application relates to the technical field of organic materials, in particular to an organic compound, an electronic component and an electronic device.

Background technique

Organic electroluminescent materials (OLED), as a new generation of display technology, have the advantages of ultra-thin, self-luminous, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, and low energy consumption. It has been widely used in industries such as flat panel displays, flexible displays, solid-state lighting, and automotive displays.

Organic light-emitting devices generally include an anode, a cathode, and an organic material layer in between. The organic material layer is usually formed in a multi-layer structure composed of different materials to improve the brightness, efficiency and life of the organic electroluminescent device. The organic material layer may be a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and Electron injection layer and other components. In the structure of an organic light-emitting device, when a voltage is applied between two electrodes, holes and electrons are injected into the organic material layer from the anode and the cathode respectively, and excitons are formed when the injected holes and electrons meet, and when these excitons return Glows in the ground state.

For existing organic electroluminescent devices, the luminous efficiency and lifetime still need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices.

Summary of the invention

The purpose of this application is to provide an organic compound, electronic component and electronic device to improve the performance of the organic electroluminescent device.

In order to achieve the above-mentioned purpose of the invention, this application adopts the following technical solutions:

According to the first aspect of the present application, an organic compound is provided, and the structural formula of the organic compound is shown in Chemical Formula 1:

Among them, any two of _{R 1} , R ₂ , R ₃ , and R _{4 are}

The other two are the same or different from each other, and are each independently selected from hydrogen, deuterium, fluorine, chlorine, alkyl groups having 1 to 12 carbon atoms, haloalkyl groups having 1 to 12 carbon atoms, and 1 to 12 carbon atoms. 12 alkoxy, carbon 3-10 cycloalkyl, carbon 6-20 aryl, carbon 1-20 heteroaryl,

Represents a chemical bond;

Each Z is the same or different from each other, and is independently selected from the structures shown in the following chemical formulas (i-12) to (i-14):

W ₁ is C(R ^w1 ) or N, W ₂ is C(R ^w2 ) or N, W ₃ is C(R ^w3 ) or N, and at least one of _{W 1} to W _{3 is N;}

W ₄ is C (R ^w4 ) or N, W ₅ is C (R ^w5 ) or N, W ₆ is C (R ^w6 ) or N, W ₇ is C (R ^w7 ) or N, and W ₄ ～W ₇ At least one of them is N;

W ₈ is C(R ^w8 ) or N, W ₉ is C(R ^w9 ) or N, and at least one of _{W 8} and W _{9 is N;}

Each of R ^w1 to R ^{w9 is the} same or different from each other and is independently hydrogen, deuterium, fluorine, chlorine, bromine, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, and the number of carbon atoms is 6-20 aryl groups, heteroaryl groups with 3-18 carbon atoms;

Ar ₁ to Ar ₆ are the same or different from each other, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 3 to 30 carbon atoms A group consisting of a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms and a substituted or unsubstituted heteroaralkyl group having 3 to 30 carbon atoms;

The substituents on Ar ₁ to Ar ₆ are the same or different from each other, and are each independently selected from: deuterium, fluorine, chlorine, bromine, aryl groups having 6 to 20 carbon atoms, and heteroaryl groups having 3 to 18 carbon atoms , Trialkylsilyl groups with 3-12 carbon atoms, arylsilyl groups with 8-18 carbon atoms, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms , Alkenyl with 2-6 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, alkoxy with 1-10 carbon atoms, carbon Alkylamino groups having 1 to 10 atoms, alkylthio groups having 1 to 10 carbon atoms, aryloxy groups having 6 to 18 carbon atoms, and arylthio groups having 6 to 18 carbon atoms;

Each L is the same or different from each other, and is independently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 12 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or Unsubstituted heteroarylene group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms;

The substituents in each L are the same or different from each other, and are each independently selected from deuterium, halogen groups, alkyl groups having 1 to 12 carbon atoms, haloalkyl groups having 1 to 12 carbon atoms, and 6-20 aryl groups, heteroaryl groups with 3-18 carbon atoms, aryloxy groups with 6-18 carbon atoms, arylthio groups with 6-18 carbon atoms, 3-12 carbon atoms A group consisting of a silyl group having 1 to 12 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, and a cycloalkyl group having 3 to 12 carbon atoms.

The present invention is a structure composed of adamantyl group as the core and two nitrogen-containing heteroaryl groups connected to adamantane through a linking group; in this structure, the adamantane is a strong electron-rich polycyclic alkane with rigidity. When combined with an electron-deficient nitrogen-containing heteroaryl group, it can generate a dipole moment and increase the polarity of the entire molecule, thereby increasing the electron mobility of the material. When it is used as the electron transport layer of an organic light-emitting electro-device, it can Improve the efficiency and life of the device and reduce the operating voltage. In addition, the heteroaryl group connected to the adamantyl group is preferably a monocyclic heteroaryl group. When the number of nitrogen-containing heteroaryl groups increases, the electronegativity decreases and the electron transport ability decreases. The large volume and rigidity of the adamantyl group also improves the film formation and thermal stability of the material, making it easier for mass production and use. Through the rigid adamantyl group to connect the lack of nitrogen-containing heteroaryl groups on both sides, the excited state energy level of the entire compound is increased, the excited state energy transfer is effectively avoided, the excitons are recombined in the light-emitting layer, and the luminous efficiency is improved.

According to a second aspect of the present application, there is provided an electronic component, including an anode and a cathode disposed opposite to each other, and a functional layer provided between the anode and the cathode; the functional layer includes the above-mentioned organic compound.

According to a third aspect of the present application, there is provided an electronic device including the above-mentioned electronic component.

Description of the drawings

The above-mentioned and other features and advantages of the present application will become more apparent by describing in detail the exemplary embodiments thereof with reference to the accompanying drawings.

FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

FIG. 2 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.

FIG. 3 is a schematic diagram of the structure of an electronic device according to an embodiment of the present application.

FIG. 4 is a schematic structural diagram of an electronic device according to another embodiment of the present application.

The reference signs of the main components in the figure are explained as follows:

100. Anode; 200. Cathode; 310. Hole injection layer; 321. Hole transport layer; 322. Electron blocking layer; 330. Organic light-emitting layer; 340. Hole blocking layer; 350. Electron transport layer; 360. Electron Injection layer; 370, photoelectric conversion layer; 400, electronic device; 500, another electronic device.

Detailed ways

Example embodiments will now be described more fully with reference to the accompanying drawings. However, the example embodiments can be implemented in various forms, and should not be construed as being limited to the examples set forth herein; on the contrary, the provision of these examples makes this application more comprehensive and complete, and fully conveys the concept of the example embodiments To those skilled in the art. The described features, structures or characteristics may be combined in one or more embodiments in any suitable way. In the following description, many specific details are provided to give a sufficient understanding of the embodiments of the present application.

In the figure, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the figures indicate the same or similar structures, and thus their detailed descriptions will be omitted.

The structural formula of the organic compound of the embodiment of the present application is shown in Chemical Formula 1:

Among them, any two of _{R 1} , R ₂ , R ₃ , and R _{4 are}

Represents a chemical bond;

Each Z is the same or different from each other, and each is independently selected from the structures shown in the following chemical formulas (i-12) to (i-14):

Each L is the same or different, and is independently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 12 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted Or an unsubstituted heteroarylene group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms;

The substituents in each L are the same or different from each other, and are each independently selected from deuterium, halogen groups, alkyl groups having 1 to 12 carbon atoms, haloalkyl groups having 1 to 12 carbon atoms, substituted or unsubstituted Aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, aryloxy groups with 6 to 18 carbon atoms, aryl groups with 6 to 18 carbon atoms The group consisting of a thio group, a silyl group having 3 to 12 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, and a cycloalkyl group having 3 to 12 carbon atoms.

In another embodiment, in the compound represented by Chemical Formula 1,

Not for

In another embodiment, in the structure represented by chemical formula (i-12) _{, at least two of W 1} to W ₃ are N, and in the structure represented by chemical formula (i-13), W ₄ to W ₇ At least two of them are N. In the structure shown in the chemical formula (i-14), both W ₈ and W ₉ are N. The present invention is a structure composed of adamantyl group as the core and two nitrogen-containing heteroaryl groups connected to adamantane through a linking group; in this structure, the adamantane is a strong electron-rich polycyclic alkane with rigidity. When combined with an electron-deficient nitrogen-containing heteroaryl group, it can generate a dipole moment and increase the polarity of the entire molecule, thereby increasing the electron mobility of the material. When it is used as the electron transport layer of an organic light-emitting electro-device, it can Improve the efficiency and life of the device and reduce the operating voltage. In addition, the heteroaryl group to which the adamantyl group is connected is preferably a monocyclic heteroaryl group. When the number of nitrogen-containing heteroaryl groups increases, the electronegativity decreases and the electron transport ability decreases, so it is preferably a triazinyl group. The large volume and rigidity of the adamantyl group also improves the film formation and thermal stability of the material, making it easier for mass production and use. Through the rigid adamantyl group to connect the lack of nitrogen-containing heteroaryl groups on both sides, the excited state energy level of the entire compound is increased, the excited state energy transfer is effectively avoided, the excitons are recombined in the light-emitting layer, and the luminous efficiency is improved.

In this specification, the term "substituted" in "substituted or unsubstituted" means that the substituents of the group can be selected from deuterium, fluorine, chlorine, bromine, aryl groups with 6 to 20 carbon atoms, carbon Heteroaryl groups having 3 to 18 atoms, trialkylsilyl groups having 3 to 12 carbon atoms, arylsilyl groups having 8 to 18 carbon atoms, alkyl groups having 1 to 10 carbon atoms, C1-C10 haloalkyl group, C2-C6 alkenyl group, C3-C10 cycloalkyl group, C2-C10 heterocycloalkyl group, C2-C It is an alkoxy group having 1 to 10, an alkylamino group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, and 6 carbon atoms ～18 arylthio.

In this application, the number of carbon atoms of L refers to the number of all carbon atoms. For example, if L is selected from substituted arylene groups with 10 carbon atoms, all carbon atoms of the arylene group and the substituents thereon are 10; if L is 9,9-dimethylfluorenyl , The substituted fluorenyl group with 15 carbon atoms, and the ring-forming carbon atoms of L is 13.

In this application, when no specific definition is provided otherwise, "hetero" means that at least one heteroatom selected from B, N, O, S, Se, Si or P is included in a functional group.

In the present application, "alkyl" may include linear or branched alkyl. Alkyl groups can have 1 to 20 carbon atoms. In this application, a numerical range such as "1 to 20" refers to each integer in the given range; for example, "1 to 20 carbon atoms" means that it can contain 1 Carbon atoms, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 Carbon atoms, 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms, or 20 carbon atoms base. The alkyl group may also be a medium-sized alkyl group having 1 to 10 carbon atoms. In some embodiments, the alkyl group is a lower alkyl group having 1 to 6 carbon atoms. In addition, the alkyl group may be substituted or unsubstituted. In other embodiments, examples of alkyl groups having 1-4 carbon atoms include, but are not limited to, methyl (Me, -CH ₃ ), ethyl (Et, -CH ₂ CH ₃ ), N-propyl (n-Pr, -CH ₂ CH ₂ CH ₃ ), isopropyl (i-Pr, -CH(CH ₃ ) ₂ ), n-butyl (n-Bu, -CH ₂ CH ₂ CH ₂ CH ₃ ), 2-methylpropyl or isobutyl (i-Bu, -CH ₂ CH(CH ₃ ) ₂ ), 1-methylpropyl or sec-butyl (s-Bu, -CH(CH ₃ ) CH ₂ CH ₃ ), tert-butyl (t-Bu, -C(CH ₃ ) ₃ ), etc.

In this application, "alkenyl" refers to a hydrocarbon group containing one or more carbon-carbon double bonds in a straight or branched hydrocarbon chain. Alkenyl groups can be unsubstituted or substituted. Alkenyl groups can have 2 to 20 carbon atoms, and whenever appearing herein, a numerical range such as "2 to 20" refers to each integer in the given range; for example, "2 to 20 carbon atoms" means that Contains 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms , 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms or 20 carbon atoms alkenyl. For example, the alkenyl group may be vinyl, butadiene, or 1,3,5-hexatriene. Alkenyl groups can have 2 to 6 carbon atoms, and a numerical range such as "2 to 6" in this application refers to each integer in the given range; for example, "2 to 6 carbon atoms" means that it can contain 2 carbons. Atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms alkenyl. For example: the alkenyl group can be vinyl, allyl, isopropenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2 -Pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadiene, allyl.

In this application, cycloalkyl refers to saturated hydrocarbons containing alicyclic structures, including monocyclic, spirocyclic, and condensed ring structures. Cycloalkyl groups can have 3-20 carbon atoms, and a numerical range such as "3 to 20" refers to each integer in the given range; for example, "3 to 20 carbon atoms" means that it can contain 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms, 13 carbon atoms, A cycloalkyl group of 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms, or 20 carbon atoms. The cycloalkyl group may be a small ring, an ordinary ring, or a large ring having 3 to 20 carbon atoms. Cycloalkyl groups can also be classified as monocyclic (only one ring), bicyclic (two rings), or polycyclic (three or more rings). Cycloalkyl groups can also be divided into two rings sharing one carbon atom-spiro ring, two rings sharing two carbon atoms-fused ring and two rings sharing two or more carbon atoms (bridged ring). In addition, cycloalkyl groups may be substituted or unsubstituted.

The "ring" in this application includes saturated rings and unsaturated rings; saturated rings are cycloalkyl, heterocycloalkyl, and unsaturated rings, namely cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl.

In this application, an aryl group refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group can be a monocyclic aryl group or a polycyclic aryl group. In other words, the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups conjugated by a carbon-carbon bond, through A monocyclic aryl group and a fused ring aryl group conjugated by carbon-carbon bonds, and two or more fused ring aryl groups conjugated by a carbon-carbon bond. That is, two or more aromatic groups conjugated through carbon-carbon bonds can also be regarded as aryl groups in the present application. Among them, the aryl group does not contain heteroatoms. For example, in this application, biphenyl, terphenyl, etc. are aryl groups. Examples of aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, hexaphenyl, benzo[9,10 ]Phenanthryl, pyrenyl, perylene, benzofluoranthene,

Base, spirobifluorenyl, etc., but not limited thereto.

In this application, a substituted aryl group means that one or more hydrogen atoms in the aryl group are replaced by other groups. For example, at least one hydrogen atom is replaced by a deuterium atom, F, Cl, I, CN, hydroxyl, amino, branched alkyl, linear alkyl, cycloalkyl, alkoxy, alkylamino, alkylthio, aryl, Heteroaryl, alkylsilyl or other group substitution. It can be understood that the number of carbon atoms of the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, the substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituent on the aryl group is 18. For example, 9,9-dimethylfluorenyl is a substituted aryl group having 15 carbon atoms.

In the present application, the heteroaryl group may be a heteroaryl group including at least one of B, O, N, P, Se, Si, and S as a heteroatom. The heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, the heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic The ring system is an aromatic monocyclic ring or an aromatic fused ring. Exemplarily, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, Acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazine Azinyl, isoquinolinyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazole Group, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzene Thiazolyl, phenothiazinyl, dibenzosilyl, dibenzofuranyl, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, etc. are not limited thereto. Among them, thienyl, furanyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system, N-phenylcarbazolyl, N-heteroarylcarbazolyl, phenyl substituted dibenzofuranyl, etc. It is a heteroaryl group of multiple aromatic ring systems conjugated through carbon-carbon bonds.

In this application, a substituted heteroaryl group means that one or more hydrogen atoms in the heteroaryl group are replaced by other groups. For example, at least one hydrogen atom is replaced by a deuterium atom, F, Cl, I, CN, hydroxyl, amino, branched alkyl, linear alkyl, cycloalkyl, alkoxy, alkylamino, alkylthio, heterocyclic group , Haloalkyl, aryl, heteroaryl, alkylsilyl, arylsilyl, or other group substitutions. It can be understood that the number of carbon atoms of the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on it.

In the present invention, the ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl group. The 6 to 10-membered aromatic ring refers to benzene ring, indene ring, naphthalene ring, etc.

In this application, the explanation of aryl can be applied to arylene, the explanation of heteroaryl can be applied to heteroarylene, the explanation of alkyl can be applied to alkylene, and the explanation of cycloalkyl can be Applied to cycloalkylene.

In the present invention, the ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl group. 6-10 membered aromatic ring refers to benzene ring, indene ring, naphthalene ring and so on.

The term "optional" or "optionally" means that the event or environment described later can but need not occur, and the description includes occasions where the event or environment occurs or does not occur. For example, "heterocyclic group optionally substituted by an alkyl group" means that an alkyl group may but does not have to be present, and the description includes the scenario where the heterocyclic group is substituted by an alkyl group and the scenario where the heterocyclic group is not substituted by an alkyl group. . For example, "optionally, attached to the same atom of E ¹⁶ and E ¹⁷ may be connected to each other to form a saturated or unsaturated 5- to 10-membered aliphatic ring" means E ¹⁶ is connected to the same atom and E ¹⁷ can form a ring but does not have to form a ring. This scheme includes the scenario where E ¹⁶ and E ¹⁷ are connected to each other to form a saturated or unsaturated 5- to 10-membered aliphatic ring, as well as the situation where E ¹⁶ and E ¹⁷ exist independently of each other. scene. Another example: "optionally, R ^v2 and R ^v3 connected to the same atom are connected to each other to form a saturated or unsaturated 5- to 10-membered aliphatic ring" means R ^v2 and R connected to the same atom ^v3 can form a ring but does not have to form a ring. This scheme includes scenarios where R ^v2 and R ^v3 are connected to form a saturated or unsaturated 5- to 10-membered aliphatic ring, and also includes scenarios where R ^v2 and R ^v3 exist independently of each other .

The description methods used in this application, "each... are independently", "... are independently" and "... are independently selected from" are interchangeable, and should be understood in a broad sense, which can mean either In different groups, the specific options expressed between the same symbols do not affect each other, or it can mean that the specific options expressed between the same symbols do not affect each other in the same group.

For example: in "

Wherein, each q is independently 0, 1, 2 or 3, and each R "independently selected from hydrogen, fluorine, and chlorine" in the description, its meaning is: formula Q-1 represents that there are q substituents R on the benzene ring ", each R" can be the same or different, and the options of each R" do not affect each other; formula Q-2 means that there are q substituents R" on each benzene ring of biphenyl, and the two benzene rings The number q of R" substituents may be the same or different, and each R" may be the same or different, and the options of each R" do not affect each other.

The non-positioned link in this application refers to the single bond extending from the ring system

It means that one end of the link can be connected to any position in the ring system that the bond penetrates, and the other end is connected to the rest of the compound molecule.

For example, as shown in the following formula (f), the naphthyl group represented by the formula (f) is connected to other positions of the molecule through two non-positional linkages that penetrate the bicyclic ring, and the meaning represented by the formula (f) -1) Any possible connection mode shown in formula (f-10).

For another example, as shown in the following formula (X'), the phenanthryl group represented by the formula (X') is connected to other positions of the molecule through a non-localized bond extending from the middle of the benzene ring on one side, which means The meaning of includes any possible connection mode as shown in formula (X'-1) ~ formula (X'-4).

The non-positional substituent in this application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be attached to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R group represented by the formula (Y) is connected to the quinoline ring through a non-localized linkage, and its meaning includes the following formula (Y-1) to Any possible connection mode shown in formula (Y-7).

Hereinafter, the meaning of non-positioning connection or non-positioning substitution is the same as here, and will not be repeated in the following.

Optionally, the organic compound of the present application is any one of the following two types:

Chemical formula 2 shows that R ₁ and R ₄ are

R ₂ and R ₃ are hydrogen; chemical formula 3 shows that R ₂ and R ₃ are

R ₁ and R ₄ are hydrogen.

It should be noted that in each of the above chemical formulas, two Ls are the same, and two Zs are the same, so that the organic compound forms a symmetrical structure.

In some embodiments, in the compound represented by Chemical Formula 1, each L is the same as each other, and each L is selected from a single bond or selected from the group consisting of the following groups:

* Indicates the site used to connect to the adamantyl group, ** indicates the site used to connect to Z.

Optionally, Z is selected from the following groups:

_{Optionally, Ar 1} to Ar ₆ in the compound of the present application are the same or different from each other, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted carbons. A group consisting of 3-18 heteroaryl groups.

Optionally, Ar ₁ to Ar ₆ are the same or different from each other, and are each independently hydrogen, deuterium, or selected from the following groups:

Each of V _{1 to} V _{10 is} independently selected from C(R ^v ) and N. When a group contains two or more R ^v , any two R ^{v are the} same or different;

In the above groups, each V is independently selected from the group consisting of O, S, Se, N (R ^v1 ), C (R ^v2 R ^v3 ) and Si (R ^v2 R ^v3 );

T is selected from O, S or N (R ^v1 );

Each T ₁ to T _{10 is} independently selected from C(R ^t ) and N. When a group contains two or more R ^t , any two R ^{t are the} same or different;

Each ^{^{^{R a, R b, R t}}} , R v, R v2, R v3 each independently hydrogen, deuterium, fluoro, chloro, bromo, alkyl having a carbon number of 1 to 6 carbon atoms and 1 to 6 The halogenated alkyl group, the alkoxy group with 1 to 6 carbon atoms, the alkylsilyl group with 3 to 12 carbon atoms, the aryl group with 6 to 12 carbon atoms, the heteroaromatic group with 3 to 12 carbon atoms Group and a cycloalkyl group having 3 to 10 carbon atoms;

Each R ^{v1 is} selected from hydrogen, deuterium, alkyl groups having 1 to 6 carbon atoms, haloalkyl groups having 1 to 6 carbon atoms, aryl groups having 6 to 12 carbon atoms, and those having 3 to 12 carbon atoms A heteroaryl group and a cycloalkyl group having 3 to 10 carbon atoms; or, optionally, R ^v2 and R ^v3 connected to the same atom are connected to each other to form saturated or unsaturated 5 to 13 Yuan ring. It means that in this application, R ^v2 and R ^v3 may be connected to each other to form a saturated or unsaturated 5- to 13-membered ring with the atoms they are commonly connected to, or may exist independently of each other. In other words, when R ^v2 and R ^v3 form a ring, ^{the ring formed by R v2} and R ^v3 is spiro-connected with the other parts of the molecule. For example,

When T ₁ ~ T ₈ are both CH, V is ^{^{C (R v2 R v3),}} R v2 and R ^v3 each other to form a ring where means are R ^v2 and R ^v3 can be connected to each other to form a ring, may be Exist independently of each other; when they form a ring, the number of carbon atoms of the ring can be a 5-membered ring, for example

It can also be a 6-membered ring, for example

It can also be a 13-membered ring, for example

Of course, the ^{number of carbon atoms on the ring formed by the interconnection of R v2} and R ^v3 can also be other values, which will not be listed here.

_{Optionally, Ar 1} to Ar _{6 in the} compound of the application are the same or different from each other, and are each independently selected from substituted or unsubstituted Wz, and the unsubstituted Wz is selected from the group consisting of the following groups:

When the above-mentioned Wz group is substituted, the substituent of the Wz is selected from deuterium, fluorine, chlorine, alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, and 1 ～4 halogenated alkyl group, C3-9 alkylsilyl group, C3-10 cycloalkyl group, C6-12 aryl group, C3-12 The substituent of the heteroaryl group is substituted; when there are multiple substituents of W, the substituents are the same or different from each other. The number of substituents of Wz can be multiple, such as 1, 2, 3, 4, 5 or more, which is not specifically limited in this application.

As a further option, Ar ₁ to Ar _{6 in the} compounds of the present application are the same or different from each other, and are each independently selected from the group consisting of the following groups:

In this application, Ar ₁ to Ar ₆ are not limited to the structures listed above.

_{Optionally, the substituents on Ar 1} to Ar ₆ of the compound of the present application are the same or different from each other, and each substituent is independently selected from deuterium, fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, Trifluoromethyl, methoxy, ethoxy, isopropoxy, trifluoromethyl, cyclohexane, cyclopentyl, trimethylsilyl, diisopropylmethylsilyl, phenyl , Naphthyl, quinolinyl, isoquinolinyl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothienyl, indolyl, carbazolyl.

In other embodiments, in the compound represented by Chemical Formula 1, the Ar ₂ to Ar ₆ are the same or different from each other, and are each independently selected from substituted or unsubstituted W, and the unsubstituted W is selected from the following groups: 'S group:

When the W group is substituted, the substituent of W is selected from deuterium, fluorine, chlorine, alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. 4 halogenated alkyl groups, alkylsilyl groups having 3 to 9 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 12 carbon atoms, heterocyclic groups having 3 to 12 carbon atoms The substituent of the aryl group is substituted; when there are multiple substituents of the W, the substituents are the same or different from each other;

The Ar _{1 is} selected from substituted or unsubstituted Wt, and the unsubstituted Wt is selected from the group consisting of:

When the Wt group is substituted, the substituent of Wt is selected from deuterium, fluorine, chlorine, alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. 4 halogenated alkyl groups, alkylsilyl groups having 3 to 9 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 12 carbon atoms, heterocyclic groups having 3 to 12 carbon atoms The substituent of the aryl group is substituted; when there are multiple substituents of the Wt, the substituents are the same or different from each other.

In these embodiments, further, the Z is selected from the following groups:

Further, the Ar ₂ to Ar _{6 are} independently selected from the group consisting of the following groups:

The Ar _{1 is} independently selected from the group consisting of:

In these embodiments, optionally, each L in the compound of the present application is the same or different from each other, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 ring carbon atoms, and a substituted Or an unsubstituted heteroarylene group having 3 to 18 ring carbon atoms; the substituents in each L are the same or different from each other, and are each independently selected from deuterium, fluorine, chlorine, and 1 to 12 carbon atoms Alkyl groups, haloalkyl groups with 1-12 carbon atoms, substituted or unsubstituted aryl groups with 6-15 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-12 carbon atoms, and carbon atoms A group consisting of an alkylamino group of a silyl group having 3 to 8 and a cycloalkyl group having 5 to 10 carbon atoms.

In these embodiments, optionally, L is selected from a single bond or from the group consisting of a group represented by chemical formula j-1 to a group represented by chemical formula j-13:

Among them, M _{2 is} selected from a single bond or

Q ₁ to Q ₅ are each independently selected from N or C(F ₅ ), and _{at least one of Q 1} to Q ₅ is selected from N; when _{two or more of Q 1} to Q ₅ are selected from C(F ₅ ), any two F _{5s are the} same or different;

Q ₆ to Q ₁₃ are each independently selected from N or C(F ₆ ), and _{at least one of Q 6} to Q ₁₃ is selected from N; when _{two or more of Q 6} to Q ₁₃ are selected from C(F ₆ ), any two F _{6 are the} same or different;

Q ₁₄ to Q ₂₃ are each independently selected from N or C(F ₇ ), and _{at least one of Q 14} to Q ₂₃ is selected from N; when _{two or more of Q 14} to Q ₂₃ are selected from C(F ₇ ), any two F _{7s are the} same or different;

Q ₂₄ to Q ₃₃ are each independently selected from N or C(F ₈ ), and _{at least one of Q 24} to Q ₃₃ is selected from N; when _{two or more of Q 24} to Q ₃₃ are selected from C(F ₈ ), any two F _{8s are the} same or different;

E ₁ to E ₁₄ and F ₅ to F ₈ are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, heteroaryl groups having 3 to 18 carbon atoms, aryl groups having 6 to 20 carbon atoms, A trialkylsilyl group having 3 to 12 carbon atoms, an arylsilyl group having 8 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, Cycloalkyl groups having 3 to 10 carbon atoms, heterocycloalkyl groups having 2 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, alkylamino groups having 1 to 10 carbon atoms, carbon Alkylthio group having 1 to 10 atoms, aryloxy group having 6 to 18 carbon atoms, and arylthio group having 6 to 18 carbon atoms;

e _r is the number of the substituent _Er , r is any integer from 1 to 14; when r is selected from 1, 2, 3, 4, 5, 6, 9, 13 or 14, e _{r is} selected from 1, 2, 3 or 4; when r is selected from 7 or 11, e _{r is} selected from 1, 2, 3, 4, 5 or 6; when r is 12, e _{r is} selected from 1, 2, 3, 4, 5, 6 Or 7; when r is selected from 8 or 10, e _{r is} selected from 1, 2, 3, 4, 5, 6, 7 or 8; when e _{r is} greater than 1, any two E _{r are the} same or different;

K _{3 is} selected from O, S, Se, N (E ₁₅ ), C (E ₁₆ E ₁₇ ), Si (E ₁₆ E ₁₇ ); wherein, E ₁₅ , E ₁₆ , and E ₁₇ are each independently selected from: carbon atoms An aryl group having 6 to 20, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and a carbon number of 2 to 10 heterocycloalkyl, or,

Optionally, E ₁₆ and E ₁₇ are connected to each other to form a saturated or unsaturated ring with their commonly connected atoms; meaning that, in the present application, E ₁₆ and E ₁₇ may be atoms connected to each other to connect to them. It exists in the form of a saturated or unsaturated ring, or it may exist independently of each other. In other words, when E ₁₆ and E ₁₇ form a ring, _{the ring formed by E 16} and E ₁₇ and the other parts of the molecule are spiro-connected. It should be noted that when E ₁₆ and E ₁₇ form a ring, the number of carbon atoms of the ring can be a 5-membered ring, for example

It can also be a 6-membered ring, for example

It can also be a 13-membered ring, for example

Of course, the _{number of carbon atoms forming the ring of E 16} and E ₁₇ can also be other values, which will not be listed one by one here, and this application does not specifically limit the number of carbon atoms of the ring.

K _{4 is} selected from a single bond, O, S, Se, N (E ₁₈ ), C (E ₁₉ E ₂₀ ), Si (E ₁₉ E ₂₀ ); wherein, E ₁₈ , E ₁₉ , and E ₂₀ are each independently selected from : C6-C20 aryl group, C3-C18 heteroaryl group, C1-C10 alkyl group, C3-C10 cycloalkyl group, C3-C10 Is a heterocycloalkyl group of 2-10; or,

Optionally, E ₁₉ and E ₂₀ are connected to each other to form a saturated or unsaturated 5- to 10-membered aliphatic ring with the atoms with which they are commonly connected. It means that in the present application, E ₁₉ and E ₂₀ may be connected to each other to form a saturated or unsaturated 5- to 10-membered aliphatic ring with the atoms they are commonly connected to, or they may exist independently of each other. In other words, when E ₁₉ and E ₂₀ form a ring, _{the ring formed by E 19} and E ₂₀ and the other parts of the molecule are spiro-connected. The understanding here that E ₁₉ and E ₂₀ optionally form a ring is consistent with the understanding in other technical solutions of this application (when E ₁₆ and E ₁₇ are connected to each other to form a ring).

Optionally, L is selected from a single bond, substituted or unsubstituted Ws, and the unsubstituted Ws is selected from the group consisting of:

When the above group Ws is substituted, the substituent of the Ws is selected from the group consisting of deuterium, fluorine, chlorine, alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, and 1 ～4 halogenated alkyl groups, 3-9 alkylsilyl groups, 3-10 cycloalkyl groups, 6-13 aryl groups, 3-12 carbon atoms The substituents of the heteroaryl group are substituted; when there are multiple substituents of Ws, the substituents are the same or different from each other.

Optionally, the substituents on each L in the compound of the present application are the same or different from each other, and each substituent is independently selected from deuterium, fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl Group, methoxy, ethoxy, isopropoxy, trifluoromethyl, cyclohexane, cyclopentyl, trimethylsilyl, diisopropylmethylsilyl, phenyl, naphthyl , Quinolinyl, isoquinolinyl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothienyl, indolyl, carbazolyl.

As a further option, L is selected from a single bond or from the group consisting of:

Wherein, * means for connecting with adamantyl group, ** means for connecting with Z. In this application, L is not limited to the above listed structures.

In other embodiments, in the compound represented by Chemical Formula 1, said L is selected from a single bond or from the group consisting of the following groups:

Optionally, the organic compound of the present application is selected from the group consisting of the following compounds:

The following synthesis examples and examples are used to further illustrate and explain the content of this application.

Generally, the organic compound of the present application can be prepared by the method described in the present application. Those skilled in the art will recognize that the chemical reactions described in this application can be used to appropriately prepare many other compounds in this application, and other methods for preparing organic compounds in this application are all considered to be within the scope of this application. within. For example, those skilled in the art can synthesize other organic compounds in this application by referring to or appropriately modifying the preparation methods provided in this application. For example, they can use appropriate protecting groups to utilize other known organic compounds other than those described in this application. Reagents, modification of reaction conditions, etc.

In the synthesis examples described below, unless otherwise stated, the temperatures are all in degrees Celsius. Some reagents are purchased from commodity suppliers such as Aldrich Chemical Company, Arco Chemical Company and Alfa Chemical Company, etc. Unless otherwise stated, these reagents are used without further purification. Some conventional reagents were purchased from Shantou Xilong Chemical Factory, Guangdong Guanghua Chemical Reagent Factory, Guangzhou Chemical Reagent Factory, Tianjin Haoyuyu Chemical Co., Ltd., Tianjin Fuchen Chemical Reagent Factory, Wuhan Xinhuayuan Technology Development Co., Ltd., Qingdao Tenglong Chemical Reagent Co., Ltd. and Qingdao Ocean Chemical Plant.

Among them, anhydrous tetrahydrofuran, dioxane, toluene and ether are obtained by refluxing and drying of sodium metal. Anhydrous dichloromethane and chloroform are obtained by refluxing and drying with calcium hydride. Ethyl acetate, petroleum ether, n-hexane, N,N-dimethylacetamide and N,N-dimethylformamide are dried in advance with anhydrous sodium sulfate.

Unless otherwise stated, the following reactions are generally carried out under a positive pressure of nitrogen or argon, or a drying tube is placed on an anhydrous solvent; the reaction flasks are all plugged with suitable rubber stoppers, and the substrate is injected into the reaction flask through a syringe. The glassware is all dried.

A silica gel column is used as the chromatographic column. Silica gel (300-400 mesh) was purchased from Qingdao Ocean Chemical Plant.

The measurement conditions for low-resolution mass spectrometry (MS) data are: Agilent 6120 quadrupole HPLC-M (column model: Zorbax SB-C18, 2.1×30mm, 3.5 microns, 6min, flow rate 0.6mL/min. Mobile phase: 5 %-95% (acetonitrile containing 0.1% formic acid) in (H2O containing 0.1% formic acid)), using electrospray ionization (ESI), and detecting with UV at 210nm/254nm.

¹ H NMR spectra were recorded using a Bruker 400MHz or 600MHz nuclear magnetic resonance spectrometer. ¹ H NMR spectrum uses CDCl ₃ , CD ₂ Cl ₂ , D ₂ O, DMSO-d ₆ , CD ₃ OD or acetone-d ₆ as the solvent (in ppm), using TMS (0 ppm) or chloroform (7.26 ppm) As a reference standard. When multiple peaks appear, the following abbreviations will be used: s (singlet, singlet), d (doublet, doublet), t (triplet, triplet), m (multiplet, multiplet), br (broadened, wide peak)

Use Agilent 1260 pre-HPLC or Calesep pump 250 pre-HPLC (column model: NOVASEP50/80mmDAC) for pure compounds, and UV detection at 210nm/254nm.

Synthesis example 1

Synthesis of Intermediate A-2

1) Synthesis of intermediate 2,2-ADM

Dissolve 2-adamantanone (25.0 g, 166.4 mmol), phenol (125.2 g, 1331.5 mmol), and 1-hexyl mercaptan (1.2 g, 10.65 mmol) in a three-necked flask. After complete dissolution, HCl (6.1 g, 166.4 mol) was added dropwise and the mixture was allowed to react in a nitrogen stream for 24 h, T=70°C. After the reaction was completed, the reaction mixture was cooled to 50°C, poured into 150 mL of water, and separated and extracted three times with 200 mL of dichloromethane. After the extracted organic layer was washed with H ₂ O three times, dried with anhydrous MgSO ₄ and stirred to remove water, the organic layer was filtered, evaporated under reduced pressure, and recrystallized with ethanol to obtain a white solid intermediate 2,2- (4-Hydroxyphenyl)adamantane (2,2-ADM), yield: 69%, m=36.6g, melting point 318°C.

2) Synthesis of Intermediate A-1

Under a nitrogen atmosphere, Intermediate 2,2-ADM (36.6g, 114.2mmol) was dissolved in 400ml of acetonitrile, and then potassium carbonate (47.4g, 342.6mmol) dissolved in 100ml of water was added to it, and then slowly 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (FX-4, 86.30g, 285.6mmol) was added dropwise, and stirred for 4h to obtain the product. The aqueous layer was removed, and then dried with anhydrous magnesium sulfate to obtain the product, and concentrated in vacuo to prepare Intermediate A-1 (87.6 g, yield 90%).

3) Synthesis of Intermediate A-2

Under a nitrogen atmosphere, intermediate A-1 (87.0g, 102.4mmol), bis(pinacol) diboron (62.2g, 244.9mmol) and potassium acetate (101.9g, 1.084mmol) were mixed and added to 600mL of two In oxane, the resultant was heated while stirring. Bis(dibenzylideneacetone)palladium (3.5 g, 6.1 mmol) and tricyclohexylphosphine (3.4 g, 12.24 mmol) were added thereto while refluxing, and the resultant was heated and stirred for 10 hours. After the completion of the reaction, the resultant was cooled to room temperature and then filtered. The filtrate was poured into water, extracted with dichloromethane, and the organic layer was dried with anhydrous magnesium sulfate. The resultant was vacuum distilled and recrystallized with ethanol to prepare Intermediate A-2 (34.1 g, yield: 62%).

Synthesis Example 2

Synthesis of Intermediate B-2

1) Synthesis of intermediate 1,3-ADM

In a N ₂ atmosphere, 1,3-dibromoadamantane (25.0g, 85.0mmol) and phenol (400g, 4251.3mmol) were dissolved in a three-necked flask. The mixture was slowly heated to 185°C and stirred for 5h, then dissolved in methanol (100ml) and after precipitation with water (1000mL) at 60°C, the solution was filtered in a hot state, and the obtained 1,3-ADM was recrystallized with dichloromethane to obtain a white solid intermediate 1,3- (4-Hydroxyphenyl)adamantane (1,3-ADM), yield: 74%, m=20.1g, melting point 200°C.

2) Synthesis of intermediate B-1

Under a nitrogen atmosphere, the intermediate 1,3-ADM (20.0 g, 62.2 mmol) was dissolved in 200 ml of acetonitrile, and then potassium carbonate (25.9 g, 187.2 mmol) dissolved in 50 ml of water was added thereto, and then slowly 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (FX-4, 47.1 g, 156.0 mmol) was added dropwise, and stirred for 3 h to obtain the product. The aqueous layer was removed, and then dried with anhydrous magnesium sulfate to obtain the product, and concentrated in vacuo to prepare Intermediate B-1 (45.7 g, yield 86%).

3) Synthesis of intermediate B-2

Under a nitrogen atmosphere, intermediate B-1 (45.0g, 52.8mmol), bis(pinacol) diboron (32.2g, 126.7mmol) and potassium acetate (31.1g, 316.7mmol) were mixed and added to 400mL of two In oxane, the resultant was heated while stirring. Bis(dibenzylideneacetone)palladium (1.82 g, 3.2 mmol) and tricyclohexylphosphine (1.8 g, 6.3 mmol) were added thereto while refluxing, and the resultant was heated and stirred for 10 hours. After the completion of the reaction, the resultant was cooled to room temperature and then filtered. The filtrate was poured into water, extracted with dichloromethane, and the organic layer was dried with anhydrous magnesium sulfate. The resultant was vacuum distilled and recrystallized with ethanol to prepare Intermediate B-2 (18.5 g, yield: 65%).

Synthesis Example 3

Synthesis of Intermediate C-2

1>Put 1-adamantanol (50.00g, 328.45mmol), bromobenzene (113.45g, 722.59mmol), and dichloromethane (500mL) into a round bottom flask. Under nitrogen protection, the temperature is lowered to -5℃ and three Fluoromethanesulfonic acid (123.23g, 821.12mmol), keep warm and stir for 3h; add deionized water (300mL) to the reaction solution to wash to pH=7, add dichloromethane (100mL) for extraction, combine the organic phases and use anhydrous The magnesium sulfate was dried, filtered, and the solvent was removed under reduced pressure; the obtained crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid intermediate C-1 (58.62 g, 40.00%).

2> Add Intermediate C-1 (20g, 44.8mmol) into a round bottom flask, add 300ml of THF to the flask after removing water, cool the system to -80℃～-90℃ with liquid nitrogen, and start dripping N-Butyllithium (7.17g, 112.1mmol), after dripping, keep for 1h. Trimethyl borate (11.64g, 112.1mmol) was added dropwise, and the temperature was still maintained at -80°C to -90°C. After the dripping was completed, the temperature was kept for 1h, and then it was naturally raised to room temperature. After the reaction was completed, an aqueous solution of HCl was added and stirred for 0.5h. Add dichloromethane and water for liquid separation extraction, wash the organic phase to neutral pH=7, combine the organic phases, _{dry for 10 min with anhydrous MgSO 4} , filter, spin-dry the filtrate, and beat with n-heptane twice to obtain a white solid Intermediate C-2 (9.96 g, 59.12%).

3> Prepare intermediates D-2 to E-2 in the same manner as in C-2, except that raw material 2 is used instead of bromobenzene in the synthesis of C-2.

Table 1:

Synthesis of Intermediate I-3

Combine 2-chloro-4,6-diphenyl-1,3,5-triazine (20.00g, 74.70mmol), p-chlorophenylboronic acid (14.01g, 89.64mmol), tetrakistriphenylphosphine palladium (1.72g) , 1.49mmol), potassium carbonate (22.71g, 164.35mmol), tetrabutylammonium chloride (4.15g, 14.94mmol), toluene (160mL), ethanol (80mL) and deionized water (40mL) were added to a three-necked flask, Under the protection of nitrogen, the temperature was increased to 78°C, and the mixture was heated under reflux and stirred for 8 hours. After the reaction, the solution was cooled to room temperature, toluene (200 mL) was added to extract the reaction solution, the organic phases were combined, the organic layers were dried with anhydrous magnesium sulfate, filtered, and concentrated; the crude product was purified by silica gel column chromatography to obtain solid intermediate I-3 (20.59g, 80%).

Intermediates I-1 and I-2 were prepared in the same way as I-3, except that the raw material 2 was used instead of m-chlorobenzeneboronic acid in the synthesis.

The intermediates of this type in the following examples can all be prepared according to the synthesis method of the above-mentioned intermediates.

Synthesis Example 4: Preparation of Compound 17

Under a nitrogen atmosphere, compound A-2 (5.00g, 9.25mmol) and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (3.17g, 9.25mmol) ) Was completely dissolved in tetrahydrofuran (100ml), then potassium carbonate (3.84g, 27.76mmol) dissolved in 30mL of water was added to it, and then tetrakis(triphenylphosphine) palladium (0.32g, 0.28mmol) was added to it. The resultant was heated and stirred for 7h. After the completion of the reaction, the temperature was lowered to room temperature, filtered, the filter cake was washed with absolute ethanol to remove water, the white filter cake was collected, and recrystallized from toluene to obtain a white solid compound 17 (6.06 g, yield 72%).

LC-MS (ESI, pos.ion) m/z: 903.41 [M+H] ⁺ .

¹ HNMR (400MHz, CD ₂ Cl ₂ ) δ (ppm): 8.82 (s, 2H), 8.65 (d, 8H), 8.54 (d, 2H), 7.71-7.62 (m, 12H), 7.60-7.56 (m , 8H), 7.48 (d, 4H), 2.12 (s, 2H), 1.95 (s, 6H), 1.85-1.74 (m, 6H).

Synthesis Example 5: Preparation of Compound 70

Under a nitrogen atmosphere, compound B-2 (5.00g, 9.25mmol) and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (3.17g, 9.25mmol) ) Was completely dissolved in tetrahydrofuran (100ml), then potassium carbonate (3.84g, 27.76mmol) dissolved in 30ml of water was added to it, and then tetrakis(triphenylphosphine)palladium (0.32g, 0.28mmol) was added to it, The resultant was heated and stirred for 7h. After the reaction, the temperature was lowered to room temperature, filtered, the filter cake was washed with absolute ethanol to remove water, the white filter cake was collected, and recrystallized from toluene to obtain a white solid compound 70 (5.7 g, yield 68%).

LC-MS(ESI,pos.ion)m/z:903.41[M+H] ⁺

Synthesis Example 6: Preparation of Compound 22

The 2-chloro-4,6-diphenyl-1,3,5-triazine (10.00g, 37.35mmol), 4-chloro-3-methylphenylboronic acid (6.68g, 39.22mmol), four (three Phenylphosphine) palladium (0.86g, 0.75mmol), potassium carbonate (12.91g, 93.38mmol), tetrabutylammonium chloride (0.52g, 1.86mmol), toluene (80mL), ethanol (40mL) and deionized water (20mL) was added to a round bottom flask, heated to 78°C under nitrogen protection, and stirred for 10 hours; the reaction solution was cooled to room temperature, toluene (100mL) was added for extraction, the organic phases were combined, dried with anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure; the obtained crude product was purified by silica gel column chromatography using dichloromethane/n-heptane as the mobile phase, and then recrystallized and purified with a toluene system to obtain Intermediate I-1 (10.42 g, yield 78%). Compound 22 was prepared in the same manner as in Synthesis Example 4, except that I-1 was used instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5 in Synthesis Example 4 -Triazine, 18.1 g of a white solid product was obtained with a yield of 67%.

LC-MS (ESI, pos.ion) m/z: 931.44 [M+H] ⁺ .

Synthesis Example 7: Preparation of Compound 67

Compound 67 was prepared in the same manner as in Synthesis Example 5, except that Intermediate I-1 was used instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine, The yield was 63%.

LC-MS (ESI, pos.ion) m/z: 931.44 [M+H] ⁺ .

¹ HNMR (400MHz, CD ₂ Cl ₂ ) δ (ppm): 8.81 (d, 8H), 8.62 (d, 2H), 8.57 (s, 2H), 7.66-7.56 (m, 12H), 7.47 (d, 2H) ), 7.33(s, 8H), 2.26(s, 6H), 2.13(s, 2H), 1.98(s, 6H), 1.86-1.73(m, 6H).

Synthesis Example 8: Preparation of Compound 24

Compound 24 was prepared in the same manner as in Synthesis Example 5, except that Intermediate I-2 was used instead of Intermediate I-3 in Synthesis Example 5 to obtain Compound 24. The yield was 66%.

LC-MS (ESI, pos.ion) m/z: 905.40 [M+H] ⁺ .

Synthesis Example 9: Preparation of Compound 73

Compound 73 was prepared in the same manner as in Synthesis Example 5, except that Intermediate I-2 was used instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3 in Synthesis Example 5. ,5-Triazine. The yield is 70%.

LC-MS (ESI, pos.ion) m/z: 905.40 [M+H] ⁺ .

Synthesis Example 10: Preparation of Compound 10

Compound 10 was prepared in the same manner as in Synthesis Example 4, except that 2-chloro-4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazine was used instead of Synthesis Example 4 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. The yield was 62%.

LC-MS (ESI, pos.ion) m/z: 851.38 [M+H] ⁺ .

Synthesis Example 11: Preparation of Compound 58

Compound 58 was prepared in the same manner as in Synthesis Example 5, except that 2-chloro-4-(naphthalene-1-yl)-6-phenyl-1,3,5-triazine was used instead of Synthesis Example 5 The yield of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine is 68%.

LC-MS (ESI, pos.ion) m/z: 851.38 [M+H] ⁺ .

Synthesis Example 12: Preparation of Compound 8

Compound 8 was prepared in the same manner as in Synthesis Example 4, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3, 5-triazine was substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine in Synthesis Example 4, and the yield was 63%.

LC-MS (ESI, pos.ion) m/z: 904.41 [M+H] ⁺ .

Synthesis Example 13: Preparation of Compound 60

Compound 60 was prepared in the same manner as in Synthesis Example 5, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3, 5-triazine was substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine in Synthesis Example 5, and the yield was 65%.

LC-MS (ESI, pos.ion) m/z: 903.41 [M+H] ⁺ .

Synthesis Example 14: Preparation of Compound 11

Compound 11 was prepared in the same manner as in Synthesis Example 4, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3, 5-triazine replaced 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine with a yield of 68%.

LC-MS (ESI, pos.ion) m/z: 903.41 [M+H] ⁺ .

Synthesis Example 15: Preparation of Compound 61

Compound 61 was prepared in the same manner as in Synthesis Example 5, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3, 5-triazine replaced 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine with a yield of 61%.

LC-MS (ESI, pos.ion) m/z: 903.41 [M+H] ⁺ .

Synthesis Example 16: Preparation of Compound 12

Compound 12 was prepared in the same manner as in Synthesis Example 4, except that 2-chloro-4-phenyl-6-(pyridin-2-yl)-1,3,5-triazine was used instead of Synthesis Example 4 The yield of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine is 65%.

LC-MS (ESI, pos.ion) m/z: 751.93 [M+H] ⁺ .

Synthesis example 17-24

The compounds 148, 53, 153, 83, 163, 199, 208, and 211 in the following table were prepared in the same manner as in Synthesis Example 4 or 5, except that different intermediates in the table below were used instead of Synthesis Example 4 The intermediate A-2 in the synthesis example 5 or the intermediate B-2 in the synthesis example 5, use the different raw material 5 in the table below to replace the 2-(3-chlorophenyl)-4,6-diphenyl in the synthesis example 4 or 5 Base-1,3,5-triazine. The raw materials used are all obtained from commercial procurement, and there is no restriction on suppliers.

Table 2:

NMR data of compound 83:

¹ HNMR (400MHz, CD ₂ Cl ₂ ) δ (ppm): 8.84 (d, 8H), 8.62 (d, 2H), 8.46 (d, 2H), 8.35 (d, 2H), 7.70 (d, 2H), 7.66-7.58 (m, 14H), 7.47 (m, 2H), 2.11 (s, 2H), 1.93 (s, 6H), 1.82-1.76 (m, 6H).

Synthesis Example 25: Preparation of Compound 188

In a nitrogen atmosphere, the raw material 2,2-dibromoadamantane (CAS: 7314-84-3,10.00g, 34.01mmol) and 2,4-diphenyl-6-pinacol ester-1,3, 5-triazine (CAS:1345345-08-5, 25.65g, 71.42mmol), potassium carbonate (10.34g, 74.82mmol), completely dissolved in toluene (80ml), 40mL of ethanol, 20mL of water, and then added to it Tetrakis(triphenylphosphine)palladium (0.78g, 0.68mmol), the resultant was heated and stirred for 10h. After the reaction, the temperature was lowered to room temperature, filtered, the filter cake was washed with absolute ethanol to remove water, the white filter cake was collected, and recrystallized from toluene to obtain a white solid compound 188 (12.21 g, yield 60%).

LC-MS (ESI, pos.ion) m/z: 599.28 [M+H] ⁺ .

Synthesis Example 26: Preparation of Compound 189

Compound 189 was prepared in the same manner as in Synthesis Example 25, except that 1,3-dibromoadamantane was used instead of 2,2-dibromoadamantane in Synthesis Example 25, and the yield was 65%.

LC-MS (ESI, pos.ion) m/z: 599.28 [M+H] ⁺ .

Other compounds of the present application can also be prepared according to the preparation methods of the above synthesis examples 1 to 26, and will not be listed here.

This application also provides an electronic component for realizing photoelectric conversion or electro-optical conversion. The electronic component includes an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; the functional layer includes the organic compound of the present application.

For example, the electronic component is an organic electroluminescent device. As shown in FIG. 1, the organic electroluminescent device includes an anode 100 and a cathode 200 arranged oppositely, and a functional layer 300 arranged between the anode 100 and the cathode 200; the functional layer 300 includes the organic compound provided in the present application.

Optionally, the functional layer 300 includes an electron transport layer 350, and the electron transport layer 350 includes an organic compound provided in the present application. Wherein, the electron transport layer 350 can be composed of the organic compound provided in this application, or can be composed of the organic compound provided in this application and other materials together.

In an embodiment of the present application, the organic electroluminescent device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, an organic electroluminescent layer 330 as an energy conversion layer, and an electron transport layer which are sequentially stacked. 350 and cathode 200. The organic compound provided in the present application can be applied to the electron blocking layer 322 of an organic electroluminescent device, which can effectively improve the luminous efficiency and lifetime of the organic electroluminescent device, and reduce the driving voltage of the organic electroluminescent device.

Optionally, the anode 100 includes the following anode material, which is optionally a material with a large work function (work function) that facilitates injection of holes into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combined metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but not limited thereto. Optionally, a transparent electrode containing indium tin oxide (ITO) as an anode is included.

Optionally, the hole transport layer 321 may include one or more hole transport materials, and the hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds. This does not make special restrictions. For example, in an embodiment of the present application, the hole transport layer 321 is composed of the compound TPD.

Optionally, the electron blocking layer 322 includes one or more electron blocking materials, and the electron blocking materials may be selected from carbazole polymers or other types of compounds, which are not specifically limited in this application. For example, in some embodiments of the present application, the electron blocking layer 322 is composed of the compound TCTA.

Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting material, and may also include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to The host material, the host material transfers energy to the guest material, so that the guest material can emit light.

The host material of the organic light-emitting layer 330 can be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, which are not particularly limited in this application . In an embodiment of the present application, the host material of the organic light-emitting layer 330 may be CBP.

The guest material of the organic light-emitting layer 330 can be a compound with a condensed aryl ring or a derivative thereof, a compound with a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials, and this application does not make any special considerations for this. limit. In an embodiment of the present application, the guest material of the organic light-emitting layer 330 may be Ir(piq) ₂ (acac).

Optionally, the cathode 200 includes the following cathode material, which is a material with a small work function that facilitates injection of electrons into the functional layer. Specific examples of cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or their alloys; or multilayer materials such as LiF/Al, Liq/ Al, LiO2/Al, LiF/Ca, LiF/Al and BaF2/Ca, but not limited thereto. Optionally, a metal electrode containing silver and magnesium is included as a cathode.

Optionally, as shown in FIG. 1, a hole injection layer 310 may be further provided between the anode 100 and the first hole transport layer 321 to enhance the ability of injecting holes into the first hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application. In an embodiment of the present application, the hole injection layer 310 may be composed of HAT-CN.

Optionally, as shown in FIG. 1, an electron injection layer 360 may be further provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic substances. In an embodiment of the present application, the electron injection layer 360 may include ytterbium (Yb).

Optionally, a hole blocking layer 340 may also be provided between the organic electroluminescent layer 330 and the electron transport layer 350.

For another example, the electronic component may be a photoelectric conversion device. As shown in FIG. 2, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200. ; The functional layer 300 contains the organic compound provided in the present application.

Optionally, as shown in FIG. 2, the photoelectric conversion device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, a photoelectric conversion layer 370 as an energy conversion layer, an electron transport layer 350, and a cathode 200 that are sequentially stacked. . The organic compound provided in the present application can be applied to the electron transport layer 350 of a photoelectric conversion device, which can effectively improve the luminous efficiency and lifetime of the photoelectric conversion device, and increase the open circuit voltage of the photoelectric conversion device.

Optionally, a hole injection layer 310 may also be provided between the anode 100 and the hole transport layer 321.

Optionally, an electron injection layer 360 may also be provided between the cathode 200 and the electron transport layer 350.

Optionally, a hole blocking layer 340 may also be provided between the photoelectric conversion layer 370 and the electron transport layer 350.

Optionally, the photoelectric conversion device may be a solar cell, especially an organic thin film solar cell. For example, as shown in FIG. 2, in an embodiment of the present application, a solar cell includes an anode 100, a hole transport layer 321, an electron blocking layer 322, a photoelectric conversion layer 370, and an electron transport layer 350 which are sequentially stacked. And the cathode 200, wherein the electron transport layer 350 contains the organic compound of the present application.

The embodiments of the present application also provide an electronic device, which includes any one of the electronic components described in the above-mentioned electronic component embodiments. Since the electronic device has any one of the electronic components described in the above-mentioned electronic component embodiments, it has the same beneficial effects, which will not be repeated here in this application.

For example, as shown in FIG. 3, the present application provides an electronic device 400, which includes any one of the organic electroluminescent devices described in the foregoing organic electroluminescent device embodiments. The electronic device 400 may be a display device, a lighting device, an optical communication device or other types of electronic devices, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, etc. Since the electronic device 400 has any one of the organic electroluminescent devices described in the foregoing organic electroluminescent device embodiments, it has the same beneficial effects, which will not be repeated here in this application.

For another example, as shown in FIG. 4, the present application provides an electronic device 500, which includes any one of the photoelectric conversion devices described in the foregoing photoelectric conversion device embodiments. The electronic device 500 may be a solar power generation device, a light detector, a fingerprint identification device, an optical module, a CCD camera, or other types of electronic devices. Since the electronic device 500 has any one of the photoelectric conversion devices described in the foregoing photoelectric conversion device embodiments, it has the same beneficial effects, which will not be repeated here in this application.

Preparation and performance evaluation of organic electroluminescent devices

Example 1: Blue organic electroluminescent device

The anode is prepared by the following process: the thickness is

The ITO substrate is cut into a size of 40mm×40mm×0.7mm, and the photolithography process is used to prepare it into a top emission experimental substrate with a cathode overlap area, an anode and an insulating layer pattern, using ultraviolet ozone and O ₂ :N ₂ plasma Perform surface treatment to increase the work function of the anode (experimental substrate) and clean the experimental substrate.

M-MTDATA (4,4',4"-tris(N-3-methylphenyl-N-phenylamino)triphenylamine) was vacuum-evaporated on the experimental substrate (anode) to form a thickness of

Hole injection layer (HIL), and vacuum evaporation of NPB on the hole injection layer to form a thickness of

The hole transport layer (HTL).

TCTA is vapor-deposited on the hole transport layer to form a thickness of

The electron blocking layer (EBL).

α, β-ADN is used as the main body, and BD-1 is doped at the same time. The main body and the dopant are formed with a film thickness ratio of 30:3.

The organic electroluminescent layer (EML).

The compound 17 of the present invention was vapor-deposited on the light-emitting layer to form a thickness of

The electron transport layer (ETL), Yb is vapor-deposited on the electron transport layer to form a thickness of

The electron injection layer (EIL) is then mixed with magnesium (Mg) and silver (Ag) at an evaporation rate of 1:9, and then vacuum-evaporated on the electron injection layer to form a thickness of

The cathode.

In addition, the thickness of the vapor deposited on the above cathode is

CP-1, forming a capping layer (CPL), thereby completing the manufacture of organic light-emitting devices.

Among them, the structural formulas of m-MTDATA, NPB, TCTA, α, β-ADN, BD-1 and CP-1 are as follows:

Example 2-23

Except that the compounds shown in Table 3 were each used when forming the electron transport layer (ETL), the same method as in Example 1 was used to fabricate an organic electroluminescent device.

Comparative Example 1-Comparative Example 6

In the Comparative Example 1 to Comparative Example 6, except that Alq ₃ , Compound A, Compound B, Compound C, Compound D, and Compound E were used as the electron transport layer instead of Compound 17, the same method as in Example 1 was used. Manufacturing organic electroluminescent devices.

The performance parameters of the prepared devices are shown in Table 3, where the IVL data compares ^{the test results at 15 mA/cm 2} and the lifetime is the test result at a current density of ^{15 mA/cm 2.}

Table 3 Device performance of Examples 1-23 and Comparative Examples 1-6

According to the results of the above [Table 3], it can be seen that Examples 1 to 23 prepared using the compound of the present invention are compared with Comparative Examples 1 to 6 using known Alq3, compounds A, B, C, D, and E. The organic electroluminescent devices of Examples 1 to 23 generally have the characteristics of reduced operating voltage, improved efficiency and increased lifetime. The working voltage is reduced by at least 0.24V, the luminous efficiency (Cd/A) is increased by at least 16%, and the life span is increased by at least 30%.

The reason is that the electron mobility of the compound used in the embodiment of the present invention ^{can reach 4×10 -3} cm ² /Vs or more under the electric field strength of ^{400 (V/cm) 1/2} , so the organic electro-induced The light-emitting device has a higher current efficiency; and because the compound uses adamantane as the bridging group to connect two electron-deficient monocyclic heteroaryl groups, so that the compound as a whole has a LUMO energy level that more closely matches the adjacent layer, so it is prepared Compared with the comparative example, the driving voltage of the obtained organic electroluminescent device will be reduced to a certain extent; finally, the adamantyl group introduced in the design and invention of the compound increases the molecular weight of the material and reduces the molecular symmetry, and improves the vitrification of the material. The transition temperature and evaporation temperature control the crystallinity of the material, so that the material has better physical and thermal stability when used in mass production, and has good durability and heat resistance, which greatly improves the life of the device.

It should be noted that only one method for preparing blue organic electroluminescent devices is given above. The organic compounds of this application can also be used in the electron transport layer of other color organic electroluminescent devices, such as red organic electroluminescent devices. Devices and green organic electroluminescent devices can also bring the same technical effects.

In a word, the organic electroluminescent device prepared by using the compound of the present invention in the electron transport layer (ETL) can achieve low driving voltage, high luminous efficiency and long life.

Claims

An organic compound, wherein the structural formula of the organic compound is shown in Chemical Formula 1:

Among them, any two of R 1 , R 2 , R 3 , and R 4 are
The other two are the same or different from each other, and are each independently selected from hydrogen, deuterium, fluorine, chlorine, alkyl groups having 1 to 12 carbon atoms, haloalkyl groups having 1 to 12 carbon atoms, and 1 to 12 carbon atoms. 12 alkoxy, carbon 3-10 cycloalkyl, carbon 6-20 aryl, carbon 1-20 heteroaryl,
Represents a chemical bond;

Each Z is the same or different from each other, and is independently selected from the structures shown in the following chemical formulas (i-12) to (i-14):

W 1 is C(R w1 ) or N, W 2 is C(R w2 ) or N, W 3 is C(R w3 ) or N, and at least one of W 1 to W 3 is N;

W 4 is C (R w4 ) or N, W 5 is C (R w5 ) or N, W 6 is C (R w6 ) or N, W 7 is C (R w7 ) or N, and W 4 ～W 7 At least one of them is N;

W 8 is C(R w8 ) or N, W 9 is C(R w9 ) or N, and at least one of W 8 and W 9 is N;

Each of R w1 to R w9 is the same or different from each other and is independently hydrogen, deuterium, fluorine, chlorine, bromine, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, and the number of carbon atoms is 6-20 aryl groups, heteroaryl groups with 3-18 carbon atoms;

Ar 1 to Ar 6 are the same or different from each other, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 3 to 30 carbon atoms A group consisting of a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms and a substituted or unsubstituted heteroaralkyl group having 3 to 30 carbon atoms;

The substituents on Ar 1 to Ar 6 are the same or different from each other, and are each independently selected from: deuterium, fluorine, chlorine, bromine, aryl groups having 6 to 20 carbon atoms, and heteroaryl groups having 3 to 18 carbon atoms , Trialkylsilyl groups with 3-12 carbon atoms, arylsilyl groups with 8-18 carbon atoms, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms , Alkenyl with 2-6 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, alkoxy with 1-10 carbon atoms, carbon Alkylamino groups having 1 to 10 atoms, alkylthio groups having 1 to 10 carbon atoms, aryloxy groups having 6 to 18 carbon atoms, and arylthio groups having 6 to 18 carbon atoms;

Each L is the same or different from each other, and is independently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 12 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or Unsubstituted heteroarylene group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms;

The substituents in each L are the same or different from each other, and are each independently selected from deuterium, halogen groups, alkyl groups having 1 to 12 carbon atoms, haloalkyl groups having 1 to 12 carbon atoms, and 6-20 aryl groups, heteroaryl groups with 3-18 carbon atoms, aryloxy groups with 6-18 carbon atoms, arylthio groups with 6-18 carbon atoms, 3-12 carbon atoms A group consisting of a silyl group having 1 to 12 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, and a cycloalkyl group having 3 to 12 carbon atoms.
The organic compound according to claim 1, wherein the organic compound is:
The organic compound according to claim 1, wherein the Z is selected from the following groups:
The organic compound according to claim 1, wherein each L is the same as each other, and the L is selected from a single bond or selected from the group consisting of:
The organic compound according to any one of claims 1 to 4, wherein Ar 1 to Ar 6 are the same or different from each other, and are each independently selected from hydrogen, deuterium, and substituted or unsubstituted aromatics having 6 to 25 carbon atoms. A group consisting of a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms.
The organic compound according to any one of claims 1 to 4, wherein the Ar 1 to Ar 6 are the same or different from each other, and are each independently selected from substituted or unsubstituted Wz, and the unsubstituted Wz is selected from the following Group of groups:

When the Wz group is substituted, the substituent of Wz is selected from deuterium, fluorine, chlorine, alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. 4 halogenated alkyl groups, alkylsilyl groups having 3 to 9 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 12 carbon atoms, heterocyclic groups having 3 to 12 carbon atoms The substituent of the aryl group is substituted; when there are multiple substituents of the Wz, the substituents are the same or different from each other.
The organic compound according to any one of claims 1 to 4, wherein the Ar 1 to Ar 6 are the same or different from each other, and are each independently selected from the group consisting of:
The organic compound according to claim 1, wherein the Ar 2 to Ar 6 are the same or different from each other, and are each independently selected from substituted or unsubstituted W, and the unsubstituted W is selected from the group consisting of :

When the W group is substituted, the substituent of W is selected from deuterium, fluorine, chlorine, alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. 4 halogenated alkyl groups, alkylsilyl groups having 3 to 9 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 12 carbon atoms, heterocyclic groups having 3 to 12 carbon atoms The substituent of the aryl group is substituted; when there are multiple substituents of the W, the substituents are the same or different from each other;

The Ar 1 is selected from substituted or unsubstituted Wt, and the unsubstituted Wt is selected from the group consisting of:

When the Wt group is substituted, the substituent of Wt is selected from deuterium, fluorine, chlorine, alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. 4 halogenated alkyl groups, alkylsilyl groups having 3 to 9 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 12 carbon atoms, heterocyclic groups having 3 to 12 carbon atoms The substituent of the aryl group is substituted; when there are multiple substituents of the Wt, the substituents are the same or different from each other.
The organic compound according to any one of claims 1 to 3 or 8, wherein the Ar 2 to Ar 6 are independently selected from the group consisting of:

The Ar 1 is independently selected from the group consisting of:
The organic compound according to any one of claims 1 to 3 or 8, wherein each L is the same or different from each other, and each is independently selected from a single bond, a substituted or unsubstituted ring-forming carbon atom of 6-25 Aryl group, substituted or unsubstituted heteroarylene group having 3 to 18 ring carbon atoms; the substituents in each L are the same or different from each other, and are each independently selected from deuterium, fluorine, chlorine, and carbon atoms It is an alkyl group having 1 to 12, a haloalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 3 to 12 carbon atoms A group consisting of an alkylamino group of a silyl group having 3 to 8 carbon atoms, and a cycloalkyl group having 5 to 10 carbon atoms.
The organic compound according to any one of claims 1 to 3 or 8, wherein the L is selected from a single bond, a substituted or unsubstituted Ws, and the unsubstituted Ws is selected from the group consisting of:

When the Ws group is substituted, the substituent of Ws is selected from deuterium, fluorine, chlorine, alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. 4 halogenated alkyl groups, alkylsilyl groups having 3 to 9 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 13 carbon atoms, heterocyclic groups having 3 to 12 carbon atoms The substituent of the aryl group is substituted; when there are multiple substituents of the Ws, the substituents are the same or different from each other.
The organic compound according to any one of claims 1 to 3 or 8, wherein the L is selected from a single bond or from the group consisting of:
The organic compound according to any one of claims 1 to 3 or 8, wherein the L is selected from a single bond or from the group consisting of:
The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of:
An electronic component, which comprises an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode;

The functional layer comprises the organic compound according to any one of claims 1-14.
The electronic component according to claim 15, wherein the functional layer includes an electron transport layer, and the electron transport layer includes the organic compound according to any one of claims 1-14.
An electronic device, comprising the electronic component according to any one of claims 15-16.