WO2021189780A1 - Organic compound, and apparatus and electronic device using same - Google Patents

Abstract

Disclosed is a carbazole-based organic compound having an adamantyl substituent. The present invention belongs to the technical field of organic electroluminescent materials. The organic compound can serve as an organic electroluminescent layer material in an organic electroluminescent apparatus, and can reduce the luminous voltage of the organic electroluminescent apparatus and improve the luminous efficiency and service life of the apparatus.

Description

Organic compounds, devices and electronic devices using them

Cross-references to related applications

The present invention claims the priority of the Chinese patent application filed on March 25, 2020 with the application number CN 202010219448.8, and the full content of the Chinese patent application disclosed above is cited here as a part of this disclosure.

The present invention claims the priority of the Chinese patent application filed on August 10, 2020 with the application number CN 202010796865.9, and the full content of the Chinese patent application disclosed above is cited here as a part of this disclosure.

Technical field

The invention belongs to the technical field of organic light-emitting materials, and specifically provides an organic compound, a device and an electronic device using the organic compound.

Background technique

With the development of electronic technology and the advancement of material science, the application range of electronic components used to realize electroluminescence or photoelectric conversion has become more and more extensive. Such electronic components usually include a cathode and an anode arranged oppositely, and a functional layer arranged between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.

Taking an organic electroluminescence device as an example, it generally includes an anode, a hole transport layer, an organic electroluminescence layer as an energy conversion layer, an electron transport layer, and a cathode that are stacked in sequence. When voltage is applied to the cathode and anode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move to the electroluminescent layer, the holes on the anode side also move to the light emitting layer, and the electrons and holes are combined in the electroluminescent layer. Excitons are formed, and the excitons are in an excited state to release energy to the outside, so that the electroluminescent layer emits light to the outside.

Summary of the invention

In order to reduce the voltage of the optoelectronic device and improve its luminous efficiency and device lifetime, the purpose of the present invention is to provide an organic compound, a device and an electronic device using the organic compound.

In order to achieve the above object, the first aspect of the present invention provides an organic compound, which has a structure represented by the following formula (1), formula (2) or formula (3):

Wherein, Ar ₁ and Ar _{2 are the} same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

R _t is

Wherein, L is selected from single bond, substituted or unsubstituted arylene group having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene group having 4 to 30 carbon atoms; Ad is substituted or unsubstituted Adamantyl

p, q, i, s, v, and m each independently represent the _{number of each substituent R t} , wherein p, q, i, s, v, and m are independently 0, 1, 2, 3, or 4, respectively, And p+q is 1, 2, 3, or 4. When p+q is 2, 3 or 4, each R _{t is the} same or different;

i+s is 0, 1, 2 or 3, when i+s is 2 or 3, each R _{t is the} same or different;

v+m is 0, 1, or 2. When v+m is 2, each R _{t is the} same or different;

n ₁ represents the number of substituents R _{1 , n 2} represents the number of substituents R ₂ , n ₁ and n _{2 are the} same or different, and are independently selected from 0, 1, 2, 3, 4 or 5; when When n _{1 is} greater than 1, any two of R _{1 are the} same or different, and when n _{2 is} greater than 1, any two of R _{2 are the} same or different;

The substituent in Ar ₁ , the substituent in Ar ₂ , the substituent in L, the substituent on Ad, R ₁ and R ₂ are the same or different from each other, and are independently selected from deuterium, fluorine, chlorine, Bromine, cyano, C1-C12 alkyl group, C2-C12 alkenyl group, C1-C12 alkoxy group, C1-C12 alkylthio group , A haloalkyl group with 1 to 12 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, a heterocycloalkyl group with 2 to 12 carbon atoms, an alkylamino group with 1 to 12 carbon atoms, any An aryl group with 6 to 20 carbon atoms and 6 to 18 carbon atoms optionally substituted with 0, 1, 2 or 3 substituents selected from deuterium, fluorine, chlorine, bromine, cyano, and alkyl Heteroaryl group, trialkylsilyl group with 3-12 carbon atoms, arylsilyl group with 6-18 carbon atoms, aryloxy group with 6-18 carbon atoms, 6 carbon atoms ～18 arylthio group; in each of L, Ar ₁ and Ar ₂ , when there are two substituents on the same atom, optionally, the two substituents are connected to each other to be connected to the atom to which they are commonly connected Together they form a 5-18 membered aliphatic ring or a 5-18 membered aromatic ring.

The second aspect of the present invention provides a device comprising an anode and a cathode disposed oppositely, and a functional layer provided between the anode and the cathode, and the functional layer contains the organic compound provided in the first aspect of the present invention.

A third aspect of the present invention provides an electronic device, which includes the device provided in the second aspect of the present invention.

Through the above technical solution, the organic compound of the present invention is used in the functional layer of the device, which can effectively improve the luminous efficiency and lifetime of the device, and reduce the driving voltage of the device.

Other features and advantages of the present invention will be described in detail in the following specific embodiments.

Description of the drawings

The accompanying drawings are used to provide a further understanding of the present invention, and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present invention, but do not constitute a limitation to the present invention. In the attached picture:

Fig. 1 is a schematic structural diagram of a specific embodiment of the organic electroluminescent device of the present invention;

Fig. 2 is a schematic structural diagram of a specific embodiment of an electronic device including the organic electroluminescent device of the present invention.

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

1: Anode 2: Cathode 3: Functional layer

30: Hole blocking layer 31: Hole injection layer 32: Hole transport layer

33: Electron barrier layer 34: Organic electroluminescent layer 35: Electron transport layer

36: Electronic injection layer 4: Electronic device

Detailed ways

The specific embodiments of the present invention will be described in detail below with reference to the accompanying drawings. It should be understood that the specific embodiments described here are only used to illustrate and explain the present invention, and are not used to limit the present invention.

The terms "the" and "said" are used to indicate the presence of one or more elements/components/etc.; There may be other elements/components/etc. besides the elements/components/etc.

The first aspect of the present invention provides an organic compound having a structure represented by the following formula (1), formula (2) or formula (3):

Wherein, Ar ₁ and Ar _{2 are the} same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

Each R _t is

Wherein, L is selected from single bond, substituted or unsubstituted arylene group having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene group having 4 to 30 carbon atoms; Ad is substituted or unsubstituted Adamantyl

p, q, i, s, v, and m each independently represent the _{number of each substituent R t} , wherein p, q, i, s, v, and m are independently 0, 1, 2, 3, or 4, respectively , And p+q is 1, 2, 3 or 4, when p+q is 2, 3 or 4, each R _{t is the} same or different; i+s is 0, 1, 2 or 3, when i+s is 2 or 3, each R _{t is the} same or different;

v+m is 0, 1, or 2. When v+m is 2, each R _{t is the} same or different;

n ₁ represents the number of substituents R _{1 , n 2} represents the number of substituents R ₂ , n ₁ and n _{2 are the} same or different, and are independently selected from 0, 1, 2, 3, 4 or 5; when When n _{1 is} greater than 1, any two of R _{1 are the} same or different, and when n _{2 is} greater than 1, any two of R _{2 are the} same or different;

The substituent in Ar ₁ , the substituent in Ar ₂ , the substituent in L, the substituent on Ad, R ₁ and R ₂ are the same or different from each other, and are independently selected from deuterium, fluorine, chlorine, Bromine, cyano, C1-C12 alkyl group, C2-C12 alkenyl group, C1-C12 alkoxy group, C1-C12 alkylthio group , A haloalkyl group with 1 to 12 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, a heterocycloalkyl group with 2 to 12 carbon atoms, an alkylamino group with 1 to 12 carbon atoms, any An aryl group having 6 to 20 carbon atoms and 6 to 18 carbon atoms optionally substituted with 0, 1, 2 or 3 substituents selected from deuterium, fluorine, chlorine, bromine, cyano or alkyl Heteroaryl group, trialkylsilyl group with 3-12 carbon atoms, arylsilyl group with 6-18 carbon atoms, aryloxy group with 6-18 carbon atoms, 6 carbon atoms ～18 arylthio; or, in each of L, Ar ₁ and Ar ₂ , when there are two substituents on the same atom, optionally, the two substituents are connected to each other to be connected to them in common The atoms together form a 5- to 18-membered aliphatic ring or a 5- to 18-membered aromatic ring.

In the present invention, two carbazole groups are connected by bonding, and the carbazole skeleton structure and adamantyl group are connected and combined to obtain a novel compound that can be used in organic electroluminescent devices; in the compound, adamantane and carbazole group The groups have high hole mobility, which further improves the overall hole mobility of the molecule, which is beneficial to reduce the working voltage of the device and improve the luminous efficiency; and the nitrogen atom in the carbazole skeleton structure is connected to the aromatic group to enhance the hole Transmission performance, the triplet energy level of the whole molecule is improved, and it has a suitable molecular energy level, which is suitable for carrier recombination. The introduction of highly rigid adamantane substituents in the molecule increases the asymmetry of the molecule, prevents the intermolecular π-π stacking to make the material difficult to crystallize, improves the film formation of the material, and improves the stability of the device; the adamantyl group also improves the glass of the compound The chemical transition temperature enables the compound to have good thermal stability, thereby improving the stability and mass production uniformity of the optoelectronic device, and can increase the life of the optoelectronic device containing the compound. When the organic compound of the present invention is used as the host material of the organic electroluminescent layer of an organic electroluminescent device, the voltage of the device can be reduced, and the luminous efficiency and service life of the device can be improved.

In this application, "optional" or "optionally" means that the event or environment described later may or may not occur, and the description includes occasions where the event or environment occurs or does not occur. For example, optionally, two substituents attached to the same atom are connected to each other to form a saturated or unsaturated 5- to 18-membered aliphatic ring or 5- to 18-membered aromatic ring with the atoms they are commonly attached to, meaning : When there are two substituents connected to the same atom, the two substituents can exist independently of each other, or they can be connected to each other to form a saturated or unsaturated 5- to 18-membered aliphatic ring with the atoms connected to them. Or 5-18 membered aromatic ring.

In the present invention, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent _Ra . For example, "substituted or unsubstituted aryl group" refers to an aryl group or a non-substituted aryl group of R _a substituents, further, may comprise one or more of the substituents on the aryl group R _a. In the present application, in the term "substituted or unsubstituted", the substituent _Ra includes, but is not limited to, deuterium, halogen groups (F, Cl, Br), cyano, alkyl, alkenyl, alkynyl , Haloalkyl, aryl, heteroaryl, aryloxy, arylthio, silyl, alkylamino, cycloalkyl, heterocyclic group.

In this application, the _{number of carbon atoms of L, Ar 1} , and Ar ₂ refers to the number of all carbon atoms in the group. For example, if L is selected from substituted arylene groups having 10 carbon atoms, all carbon atoms of the arylene group and the substituents thereon are 10. If Ar ₁ is 4-tert-butyl-1-phenyl, it belongs to a substituted aryl group having 10 carbon atoms.

In this application, "substituted or unsubstituted aryl group with 6-30 carbon atoms" and "substituted or unsubstituted aryl group with 6-30 carbon atoms" have the same meaning, and both refer to aryl groups. The total number of carbon atoms of the substituents on it is 6-30. For example, if L is selected from a substituted arylene group having 10 carbon atoms, all carbon atoms of the arylene group and the substituents thereon are 10.

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" is independently selected from hydrogen, fluorine, and chlorine. In the description, its meaning is: formula Q-1 represents q" substitutions on the benzene ring The group R", each R" can be the same or different, and the options of each R" do not affect each other; formula Q-2 means that each benzene ring of biphenyl has q "substituents R", two benzenes The number of R" substituents q" on the ring 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.

In the present application, "alkyl" may include linear or branched alkyl. Alkyl groups can have 1 to 12 carbon atoms. In this application, a numerical range such as "1 to 20" refers to each integer in the given range, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and 12; for another example, "an alkyl group of 1 to 12 carbon atoms" means that it can contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 An alkyl group of carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, or 12 carbon atoms. The alkyl group may also be a medium-sized alkyl group having 1 to 10 carbon atoms. The alkyl group may also be a lower alkyl group having 1 to 6 carbon atoms. In other embodiments, the alkyl group contains 1-4 carbon atoms; still in some embodiments, the alkyl group contains 1-3 carbon atoms. The alkyl group may be optionally substituted with one or more substituents described in the present invention. Examples of alkyl groups 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 ), isobutyl (i-Bu, -CH ₂ CH (CH ₃ ) ₂ ), sec-butyl (s-Bu, -CH(CH ₃ )CH ₂ CH ₃ ), tert-butyl (t-Bu, -C(CH ₃ ) ₃ ), etc. In addition, the alkyl group may be substituted or unsubstituted.

In this application, "alkenyl" refers to a hydrocarbon group containing one or more double bonds in a straight or branched hydrocarbon chain. Alkenyl groups can be unsubstituted or substituted. Alkenyl groups may have 2 to 12 carbon atoms, and whenever appearing herein, a numerical range such as "2 to 12" refers to each integer in the given range, such as 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and 12; for example, "alkenyl of 2 to 12 carbon atoms" means that it can contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbons Atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, or 12 carbon atoms alkenyl. For example, the alkenyl group may be vinyl, butadiene, or 1,3,5-hexatriene.

In this application, cycloalkyl refers to cyclic saturated hydrocarbons, including monocyclic and polycyclic structures. Cycloalkyl groups can have 3 to 10 carbon atoms, and a numerical range such as "3 to 10" refers to each integer in the given range, such as 3, 4, 5, 6, 7, 8, 9 and 10; for example, "Cycloalkyl of 3 to 10 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 Or a cycloalkyl group of 10 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. In some embodiments, the cycloalkyl group is a 5- to 10-membered cycloalkyl group. In other embodiments, the cycloalkyl group is a 5- to 8-membered cycloalkyl group. For example, examples of the cycloalkyl group may be, but are not limited to ：Five-membered cycloalkyl is cyclopentyl, six-membered cycloalkyl is cyclohexane, 10-membered polycyclic alkyl such as adamantyl, etc.

In the present invention, an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic 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 fused ring aryl group may include, for example, a bicyclic fused aryl group (for example, a naphthyl group), a tricyclic fused aryl group (for example, a phenanthryl group, a fluorenyl group, an anthryl group), and the like. Among them, the aryl group does not contain heteroatoms such as B, N, O, S, P, and Si. For example, in this application, biphenyl, terphenyl, etc. are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10] Phenanthryl, pyrenyl, benzofluoranthene,

Base and so on. The "aryl group" in the present application may contain 6-20 carbon atoms. In some embodiments, the number of carbon atoms in the aryl group may be 6-18. In other embodiments, the number of carbon atoms in the aryl group may be It is 6-12. For example, the number of carbon atoms of the aryl group can be 6, 12, 13, 15, 18, or 20. Of course, the number of carbon atoms can also be other numbers, which will not be listed here.

Further, in the present invention, the substituted aryl group may be one or more hydrogen atoms in the aryl group, such as deuterium atom, halogen group, -CN, aryl group, heteroaryl group, trialkylsilyl group, Alkyl, cycloalkyl, alkoxy, alkylthio and other groups are substituted. In this application, the number of carbon atoms of the substituted aryl group can be 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 Or 20. Of course, the number of carbon atoms can also be other numbers, so I won't list them all here. In this application, the substituted aryl group may be one or more of two hydrogen atoms in the aryl group, such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, alkylsilyl group, arylsilyl group. , Alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio and other groups substituted. For example, specific examples of heteroaryl substituted aryl include, but are not limited to, dibenzofuranyl substituted phenyl, dibenzothiophene substituted phenyl, carbazolyl substituted phenyl, pyridine substituted phenyl, etc. . It should be understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms refers to an aryl group and a substituted group. The total number of carbon atoms of the group is 18. For example, 9,9-dimethylfluorenyl is a substituted aryl group having 15 carbon atoms. In this application, the fluorenyl group as an aryl group can be substituted, and two substituent groups can be combined with each other to form a spiro structure. Specific examples include but are not limited to the following structures:

In the present invention, a heteroaryl group refers to a monovalent aromatic ring containing at least one heteroatom in the ring or a derivative thereof. The heteroatom may be at least one of B, O, N, P, Si, and S. 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, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silylfluorenyl, dibenzofuranyl and N-arylcarbazole Group (such as N-phenylcarbazolyl), N-heteroarylcarbazolyl (such as N-pyridylcarbazolyl), N-alkylcarbazolyl (such as N-methylcarbazolyl), etc., Not limited to this. Among them, thienyl, furanyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type, and N-arylcarbazolyl and N-heteroarylcarbazolyl are multiple groups conjugated through carbon-carbon bonds. Heteroaryl group of ring system type.

The "heteroaryl group" in this application may include 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 heteroatoms selected from B, O, N, P, Si, Se and S , And the number of carbon atoms can be 3-40, or, for example, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 , 16, 17, or 18. In some embodiments, the number of carbon atoms of the heteroaryl group can be 3 to 30, and in other embodiments, the number of carbon atoms of the heteroaryl group can be 3 to 20, or 3 to 18, or 3 to 12 One or 5-12, or 5-18. For example, the number of carbon atoms of the heteroaryl group can also be 5, 8, 9, 12, 18, 20 or 40. Of course, the number of carbon atoms can also be other numbers, which will not be repeated here. List one by one.

In the present invention, the substituted heteroaryl group may be one or more hydrogen atoms in the heteroaryl group, such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkane Group, cycloalkyl, alkoxy, alkylthio and other groups are substituted. In this application, the number of carbon atoms of the substituted heteroaryl group can be 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 One, 16, 17, 18, or 20. Of course, the number of carbon atoms can also be other numbers, so I won’t list them all here. For example, specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted carbazolyl, and phenyl-substituted pyridine. Base and so on. It should 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 the heteroaryl group. For example, a substituted heteroaryl group having 18 carbon atoms means that the total number of carbon atoms of the heteroaryl group and the substituent is 18. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, and the like.

In the present invention, the ring system formed by m atoms is an m-membered ring. For example, the phenyl group is a 6-membered aryl group; the 6-10 membered aromatic ring may refer to a benzene ring, an indene ring, a naphthalene ring, and the like.

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

In this application, "aliphatic ring" refers to cycloalkyl and cycloalkenyl.

In this application, "aromatic ring" refers to aryl and heteroaryl.

In this application, halogen includes fluorine, chlorine, bromine, and iodine.

In this specification, "silyl group" and "alkylsilyl group" have the same meaning and both refer to

Wherein, R ^G1 , R ^G2 , and R ^G3 are each independently an alkyl group. Specific examples of the alkylsilyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, and tert-butyldimethylsilyl group. , Propyldimethylsilyl.

In the present invention, an arylene group refers to a group formed by the loss of one hydrogen of an aryl group; a heteroarylene group refers to a group formed by the loss of a hydrogen of a heteroaryl group. 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 this application, the non-positioned connecting bond refers to the single bond protruding 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 represents The meaning of includes any possible connection modes shown in formula (X'-1) to 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'represented by the formula (Y) is connected to the quinoline ring through a non-localized linkage, and the meaning represented by it includes formulas (Y-1) to Any possible connection mode shown in formula (Y-7).

In this application, in each of L, Ar ₁ and Ar ₂ , when there are two substituents on the same atom, optionally, the two substituents are connected to each other to form 5 together with the atoms to which they are connected together. ～18-membered aliphatic ring or 5～18-membered aromatic ring. It means that two substituents on the same atom are connected to form a spiro cycloalkyl group, or the substituents connected on the same atom are connected to each other to form a fused aromatic ring, such as a fluorene ring.

In this application, in some embodiments _{, the substituents in Ar 1} , the substituents in Ar ₂ , the substituents in L, R ₁ and R ₂ are the same or different from each other, and are independently selected from deuterium and fluorine. , Chlorine, bromine, cyano, C1-C12 alkyl, C2-C12 alkenyl, C1-C12 alkoxy, C1-C12 Alkylthio, haloalkyl with 1-12 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-12 carbon atoms, alkylamine with 1-12 carbon atoms Group, optionally substituted by 0, 1, 2 or 3 substituents selected from deuterium, fluorine, chlorine, bromine, cyano or C1-C5 alkyl group, the number of carbon atoms is 6-20 The aryl group is optionally substituted with 0, 1, 2 or 3 carbon atoms selected from deuterium, fluorine, chlorine, bromine, cyano, alkyl with 1 to 5 carbon atoms, or phenyl substituents Heteroaryl groups having 6 to 18 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, arylsilyl groups having 6 to 18 carbon atoms, aryloxy groups having 6 to 18 carbon atoms, An arylthio group having 6 to 18 carbon atoms; or, in each of L, Ar ₁ and Ar ₂ , when there are two substituents on the same atom, optionally, the two substituents are connected to each other to Together with the atoms to which they are connected, they form a 5- to 18-membered aliphatic ring or a 5- to 18-membered aromatic ring.

In a specific embodiment of the present invention, the organic compound has one of the following structures represented by formula (I-1) to formula (I-26):

In a specific embodiment of the present invention, the organic compound has one of the following structures (I-27) to (I-31):

In some embodiments of the present invention, the R ₁ and the R ₂ are the same or different from each other, and are independently selected from deuterium, fluorine, chlorine, bromine, cyano, and alkyl with 1 to 4 carbon atoms. , Alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, trimethylsilyl with 3 to 9 carbon atoms, triphenylsilyl, phenyl, naphthyl , Quinoline, isoquinolinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenyl-carbazolyl, pyridyl, cyclopropyl, cyclopentyl, cyclohexane , The group consisting of adamantyl groups.

In other specific embodiments of the present invention, two adjacent substituents R ₁ or R ₂ can also be connected to each other to form a 5- to 18-membered fused aliphatic ring or 5 to the atoms to which they are commonly connected ~18-membered fused aromatic ring.

In some embodiments of the present invention, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroarylene group having 4 to 18 carbon atoms.

In some embodiments of the present invention, the substituents in L are the same or different from each other, and are independently selected from deuterium, fluorine, chlorine, bromine, cyano, alkyl with 1 to 4 carbon atoms, carbon Alkoxy group having 1 to 4 atoms, haloalkyl group having 1 to 4 carbon atoms, trimethylsilyl group having 3 to 9 carbon atoms, triphenylsilyl group, optionally substituted by 0, 1 , Phenyl, naphthyl, quinoline, isoquinolyl, dibenzofuranyl, dibenzothiophene substituted by 2 or 3 substituents selected from deuterium, fluorine, chlorine, bromine, cyano, and alkyl Group, carbazolyl, N-phenylcarbazolyl, pyridyl, cyclopropyl, cyclopentyl, cyclohexane, adamantyl; in each L, when there are two on the same atom In the case of a substituent, optionally, two of the substituents are connected to each other to form a 5-18 membered aliphatic ring or a 5-18 membered aromatic ring together with the atoms to which they are commonly connected.

In some embodiments of the present invention, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 4 to 12 carbon atoms.

In some embodiments of the present invention, L is selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted Naphthylene, substituted or unsubstituted 9,9-dimethylfluorene subunits, substituted or unsubstituted dibenzofuran subunits, substituted or unsubstituted dibenzothiophene subunits, substituted or unsubstituted quinylenes Linyl, substituted or unsubstituted isoquinolinylene, substituted or unsubstituted carbazolylidene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted anthrylene, substituted or unsubstituted pyridylene One of the above subunits, or a subunit group formed by connecting two or three of the above subunits through a single bond; the substituents in L are the same or different from each other, and are each independently selected from deuterium, fluorine, chlorine, and cyanide Group, methyl, ethyl, isopropyl, n-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trimethylsilyl, phenyl, cyano substituted phenyl, fluorine The group consisting of substituted phenyl, naphthyl, quinoline, isoquinolyl, pyridyl, cyclopentyl, and cyclohexyl.

For example, when L is a group formed by two or three groups through a single bond, when it is a group formed by two different groups through a single bond, and the two groups are phenylene and phenylene, respectively When dibenzofuranyl, L is

In this application, "plurality" refers to two or more.

In a specific embodiment of the present invention, L is selected from a single bond or the group consisting of the following structural formulas (j-1) to (j-14):

Among them, M _{1 is} selected from a single bond or

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

G ₆ to G ₁₃ are each independently selected from N or C(F ₂ ), and _{at least one of G 6} to G ₁₃ is selected from N; when _{two or more of G 6} to G ₁₃ are selected from C(F ₂ ) , Any two F _{2 are the} same or different;

G ₁₄ to G ₂₃ are each independently selected from N or C(F ₃ ), and _{at least one of G 14} to G ₂₃ is selected from N; when _{two or more of G 14} to G ₂₃ are selected from C(F ₃ ) , Any two F _{3 are the} same or different;

G ₂₄ to G ₃₃ are each independently selected from N or C(F ₄ ), and _{at least one of G 24} to G ₃₃ is selected from N; when _{two or more of G 24} to G ₃₃ are selected from C(F ₄ ) , Any two F _{4 are the} same or different;

F ₁ to F ₄ and Z ₁ to Z ₁₅ are each independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl groups having 3 to 12 carbon atoms, and 1 to 10 carbon atoms The alkyl group, a haloalkyl group with 1-10 carbon atoms, a cycloalkyl group with 3-10 carbon atoms, an alkoxy group with 1-10 carbon atoms, and an alkylthio group with 1-10 carbon atoms , A heteroaryl group having 3 to 18 carbon atoms or optionally substituted with 0, 1, 2 or 3 substituents selected from deuterium, fluorine, chlorine, bromine, cyano, and alkyl, the number of carbon atoms is 6-18 aryl groups;

h ₁ ～h ₁₅ are represented by h _k , Z ₁ ～Z ₁₅ are represented by Z _k , k is a variable, which is an arbitrary integer from 1 to 15, and h _k is the number of substituents Z _{k . When h k is} greater than 1, The corresponding substituents Z _{k are the} same or different;

Wherein, when k is selected from 1, 2, 3, 8, 9, 10, 11, 14, or 15, h _{k is} selected from 1, 2, 3, or 4;

When k is selected from 4, h _{k is} selected from 1, 2 or 3;

When k is selected from 5 or 6, h _{k is} selected from 1, 2, 3, 4, 5 or 6;

When k is selected from 7, h _{k is} selected from 1, 2, 3, 4, 5, 6 or 7;

When k is selected from 12 or 13, h _{k is} selected from 1, 2, 3, 4, 5, 6, 7 or 8;

K _{1 is} selected from O, S, N (Z ₁₆ ), C (Z ₁₇ Z ₁₈ ), Si (Z ₁₇ Z ₁₈ ); wherein, each of Z ₁₆ , Z ₁₇ , and Z _{18 is} independently selected from hydrogen, carbon atom Heteroaryl groups having 3 to 18, alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, or optionally 0, 1, 2 or 3 selected from deuterium, fluorine The aryl group with 6-18 carbon atoms substituted by the substituents of, chlorine, bromine, cyano, or alkyl;

Or, optionally, the above-mentioned Z ₁₇ and Z ₁₈ are connected to each other to form a 5- to 13-membered aliphatic ring or a 5- to 13-membered aromatic ring with the atoms they are commonly connected to;

K _{2 is} selected from a single bond, O, S, N (Z ₁₉ ), C (Z ₂₀ Z ₂₁ ), Si (Z ₂₀ Z ₂₁ ); wherein each of Z ₁₉ , Z ₂₀ and Z _{21 is} independently selected from hydrogen , C6-C18 aryl group, C3-C18 heteroaryl group, C1-C10 alkyl group or C3-C10 cycloalkyl group, or any Optionally, the above-mentioned Z ₂₀ and Z ₂₁ are connected to each other to form a 5- to 13-membered aliphatic ring or a 5- to 13-membered aromatic ring with their common atoms.

For example, L is

When M ₁ and K ₂ are single bonds, Z ₆ is hydrogen, and K ₁ is C (Z ₁₇ Z ₁₈ ), optionally, Z ₁₇ and Z ₁₈ connected to the same atom are connected to each other The atoms connected together to form a saturated or unsaturated 5- to 13-membered aliphatic ring means that Z ₁₇ and Z ₁₈ can be connected to each other to form a 5- to 13-membered ring, or they can exist independently of each other; when Z ₁₇ and Z ₁₈ form an aliphatic ring In the case of a group ring, the number of 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 10-membered ring, for example

Of course, the _{number of atoms in the ring formed by the interconnection of Z 17} and Z ₁₈ can also be other values, which will not be listed here. At the same time, _{the ring formed by connecting Z 17} and Z ₁₈ can also be an aromatic ring, such as a 13-membered aromatic ring,

Optionally, Z ₂₀ and Z ₂₁ are connected to each other to form a 5- to 13-membered aliphatic ring or aromatic ring with the atoms they are commonly connected to have the same meaning as Z ₁₇ and Z ₁₈ .

In an optional embodiment of the present invention, L is selected from a single bond, a substituted or unsubstituted group W ₁ , and the unsubstituted group W _{1 is} selected from the following groups:

When the W ₁ group is substituted by one or more substituents, the substituents of W ₁ are each independently selected from deuterium, fluorine, chlorine, cyano, alkyl groups having 1 to 6 carbon atoms, and the number of carbon atoms Is an alkoxy group having 1 to 4, a haloalkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 9 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and the number of carbon atoms is A group consisting of 6-15 aryl groups and 3-12 heteroaryl groups; _{when the number of substituents on W 1} is more than one, the respective substituents are the same or different. In a further optional embodiment of the present invention, when the W ₁ group is substituted by one or more substituents, the substituents of W ₁ are each independently selected from deuterium, fluorine, chlorine, cyano, The substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, trifluoromethyl, trimethylsilyl, methoxy, isopropyl Propoxy, methylthio, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, 9,9-dimethylfluorenyl, anthracenyl, phenanthryl, pyridyl , Quinolinyl, isoquinolinyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl; _{when the number of substituents on W 1} is more than one, each substituent Same or different. In an optional specific embodiment of the present invention, where L is a single bond or any one of the following groups:

In a specific embodiment of the present invention, Ad is an unsubstituted adamantyl group.

In an optional specific embodiment of the present invention, Ad is

In this application, adamantyl is 1-adamantyl

Or 2-adamantyl

In this application,

Represents the same structure.

In some embodiments of the present invention, Ar ₁ and Ar ₂ are each independently selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 18 carbon atoms .

In some embodiments of the present invention, Ar ₁ and Ar ₂ are each independently selected from substituted or unsubstituted aryl groups with 6 to 33 carbon atoms, and substituted or unsubstituted heterocyclic groups with 4 to 18 carbon atoms. Aryl.

In some embodiments of the present invention, the substituents in _{Ar 1 and Ar 2} are the same or different from each other, and are each independently selected from deuterium, fluorine, chlorine, bromine, cyano, cyclopropyl, Cyclopentyl, cyclohexane, adamantyl, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, carbon atom A trimethylsilyl group with a number of 3-9, triphenylsilyl group, optionally substituted by 0, 1, 2 or 3 substituents selected from deuterium, fluorine, chlorine, bromine, cyano, and alkyl Substituted phenyl, naphthyl, quinoline, isoquinolinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, pyridyl, the group consisting of; in each In Ar ₁ and Ar ₂ , when there are two substituents on the same atom, optionally, the two substituents are connected to each other to form a 5- to 18-membered aliphatic ring together with the atoms to which they are connected. ~18-membered aromatic ring.

In a specific embodiment of the present invention, Ar ₁ and Ar ₂ are each independently selected from the group consisting of the following chemical formulas (k-1) to (k-15):

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

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

T ₆ to T ₁₃ are each independently selected from N or C(X ₂ ), and _{at least one of T 6} to T ₁₃ is selected from N; when _{two or more of T 6} to T ₁₃ are selected from C(X ₂ ) , Any two X _{2 are the} same or different;

T ₁₄ to T ₂₃ are each independently selected from N or C(X ₃ ), and _{at least one of T 14} to T ₂₃ is selected from N; when _{two or more of T 14} to T ₂₃ are selected from C(X ₃ ) , Any two X _{3 are the} same or different;

T ₂₄ to T ₃₃ are each independently selected from N or C(X ₄ ), and _{at least one of T 24} to T ₃₃ is selected from N; when _{two or more of T 24} to T ₃₃ are selected from C(X ₄ ) , Any two X _{4 are the} same or different;

Each A _{1 is} independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, and 1 carbon atom -10 haloalkyl groups, cycloalkyl groups with 3-10 carbon atoms, alkoxy groups with 1-10 carbon atoms, and alkylthio groups with 1-10 carbon atoms;

Each of A ₂ to A ₆ and A _{16 is} independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl group having 3 to 12 carbon atoms, and alkane having 1 to 10 carbon atoms. Group, halogenated alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, carbon Alkylthio groups having 1 to 10 atoms, heteroaryl groups having 3 to 18 carbon atoms;

A ₇ to A ₁₅ , A ₁₇ to A ₂₁ , and X ₁ to X ₄ are each independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl group having 3 to 12 carbon atoms, carbon An alkyl group having 1 to 10 atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a carbon number of 1 ~10 alkylthio, 6-18 aryl, and 3-18 heteroaryl;

b ₁ ~ b ₂₁ to b _k denotes, A ₁ ~ A ₂₁ to A _k expressed, k is a variable, represents any integer of 1 to 21, b _k A _k represents the number of substituents is, when b _k is greater than 1, Any two _{Ak are the} same or different;

Wherein, when k is selected from 1, 3, 4, 6, 18, 20 or 21, b _{k is} selected from 1, 2, 3, 4 or 5;

When k is selected from 2, 5, 6, 9, 11, 13, 16 or 19, b _{k is} selected from 1, 2, 3 or 4;

When k is selected from 12 or 17, b _{k is} selected from 1, 2 or 3;

When k is selected from 10, b _{k is} selected from 1, 2, 3, 4, 5 or 6;

When k is selected from 7 or 14, b _{k is} selected from 1, 2, 3, 4, 5, 6 or 7;

When k is selected from 15, b _{k is} selected from 1, 2, 3, 4, 5, 6, 7 or 8;

When k is selected from 8, b _{k is} selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9;

L _{1 is} selected from O, S, N (A ₂₂ ), C (A ₂₃ A ₂₄ ), Si (A ₂₃ A ₂₄ ); wherein, A ₂₂ , A ₂₃ , and A ₂₄ are each independently selected from hydrogen and the number of carbon atoms Is an aryl group having 6 to 18, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, or, optionally, the above A ₂₃ and A ₂₄ are connected to each other to form a 5- to 13-membered aliphatic ring or aromatic ring with the atoms they are connected to each other;

Each L _{2 is} independently selected from a single bond, O, S, N (A ₂₅ ), C (A ₂₆ A ₂₇ ), Si (A ₂₆ A ₂₇ ); wherein, A ₂₅ , A ₂₆ , and A ₂₇ are each independently selected It is selected from an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, or any Optionally, the above-mentioned A ₂₆ and A ₂₇ are connected to each other to form a 5- to 13-membered aliphatic ring or aromatic ring with the atoms they are commonly connected to.

Optionally, the above-mentioned A ₂₃ and A ₂₄ are connected to each other to form a 5- to 13-membered aliphatic ring or aromatic ring with the atoms they are connected to each other. It means that A ₂₃ and A ₂₄ may be connected to each other to form a ring, or they may be independent of each other. exist. For example, in the formula

In, when M ₂ is a single bond, L ₂ is a single bond, A ₁₄ is hydrogen, and L ₁ is C (A ₂₃ A ₂₄ ), when A ₂₃ and A ₂₄ form a ring, the ring can be a 5-membered aliphatic Ring, for example

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

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

Of course, the _{number of carbon atoms in the ring formed by the interconnection of A 23} and A ₂₄ can also be other values, which will not be listed here. Optionally, A ₂₆ and A ₂₇ are connected to each other to form a 5- to 13-membered aliphatic ring or aromatic ring with the atoms they are commonly connected to have the same _{meaning as A 23} and A _24.

In an alternative embodiment of the present invention, the Ar ₁ and the Ar ₂ are the same or different from each other, and are independently selected from the substituted or unsubstituted group Y ₁ , the unsubstituted group Y _{1 is} selected from the following groups:

When the Y ₁ group is substituted by one or more substituents, the substituents of Y ₁ are each independently selected from deuterium, fluorine, chlorine, cyano, alkyl groups having 1 to 6 carbon atoms, and carbon atoms Is an alkoxy group having 1 to 4, a haloalkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 9 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and the number of carbon atoms is A group consisting of 6-15 aryl groups and 3-12 heteroaryl groups; _{when the substituent of Y 1} is more than one, each substituent is the same or different. In a further optional embodiment of the present invention, when the Y ₁ group is substituted by one or more substituents, the substituents of Y ₁ are each independently selected from deuterium, fluorine, chlorine, cyano, The substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, trifluoromethyl, trimethylsilyl, methoxy, isopropyl Propoxy, methylthio, cyclopropyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, cyano substituted phenyl, fluorine substituted phenyl, deuterium substituted phenyl, naphthalene Base, fluorenyl, 9,9-dimethylfluorenyl, anthracenyl, phenanthryl, pyridyl, quinolinyl, isoquinolinyl, pyrimidinyl, carbazolyl, deuterium-substituted carbazolyl, dibenzo A group consisting of furyl and dibenzothienyl; _{when the number of substituents on Y 1} is more than one, each substituent is the same or different.

In an alternative embodiment of the present invention, said Ar ₁ and said Ar ₂ are the same or different from each other, and are independently selected from substituted or unsubstituted groups Y ₂ , said unsubstituted groups Y _{2 is} selected from the following groups:

When the Y ₂ group is substituted by one or more substituents, the substituents of Y ₂ are each independently selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, n-propyl, A group consisting of tert-butyl groups; _{when the substituent of Y 2} is more than one, the substituents are the same or different.

In an alternative embodiment of the present invention, said Ar ₁ and said Ar ₂ are the same or different from each other, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl , Substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted quinoline Group, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted phenanthrenyl , Substituted or unsubstituted anthracenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted phenanthrene Pyroline, substituted or unsubstituted benzofuran[3,2-b]pyridyl, substituted or unsubstituted phenoxytheophylline, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxa Azinyl, substituted or unsubstituted spiro[cyclopentane-1,9'-fluoren] group, substituted or unsubstituted spiro[cyclohexane-1,9'-fluoren] group, substituted or unsubstituted 9H- The 9-silyl heterofluorenyl group, or a group formed by connecting two or three of the above groups through a single bond; _{the substituents in Ar 1} and Ar ₂ are the same or different from each other, and are each independently selected from deuterium and fluorine , Cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, trifluoromethyl, trimethylsilyl, methoxy, isopropoxy, methylthio, cyclopropyl, Cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, cyano-substituted phenyl, fluorine-substituted phenyl, deuterium-substituted phenyl, naphthyl, fluorenyl, 9,9-dimethyl The group consisting of fluorenyl, anthracenyl, phenanthryl, pyridyl, quinolinyl, isoquinolinyl, pyrimidinyl, carbazolyl, deuterium-substituted carbazolyl, dibenzofuranyl, and dibenzothienyl; When the number of said substituents is more than one, the respective substituents are the same or different.

In a specific embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different from each other, and are independently selected from the following groups:

In one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different from each other, and are independently selected from the following groups:

In a specific embodiment of the present invention, R ₁ and R ₂ are the same or different from each other, and are each independently selected from deuterium, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, n-propyl Base, tert-butyl, methoxy, ethoxy, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, quinoline, isoquinolyl, pyridyl, cyclopentyl, cyclohexane The group formed by the base.

In a specific embodiment of the present invention, R ₁ and R ₂ are the same or different from each other, and are each independently selected from deuterium, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, n-propyl Base, tert-butyl, methoxy, ethoxy, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, quinoline, isoquinolyl, pyridyl, cyclopentyl, cyclohexane基, 1-adamantyl.

In a specific embodiment of the present invention, the organic compound is selected from at least one of the following compounds P1-P320:

The second aspect of the present invention provides a device, which includes an anode and a cathode disposed oppositely, and a functional layer provided between the anode and the cathode, and the functional layer contains the organic compound provided in the first aspect of the present invention.

In a specific embodiment, the functional layer includes a hole injection layer, a hole transport layer, an organic electroluminescence layer, an electron transport layer, and an electron injection layer. The organic electroluminescence layer contains the organic compound provided in the first aspect of the present invention. Optionally, it contains at least one of the organic compounds P1-P320.

According to the present invention, the device may be an optoelectronic device. The optoelectronic device is well known to those skilled in the art, for example, it may be an organic electroluminescence device. Other types of optoelectronic devices will not be repeated here.

In a specific embodiment, the organic compound can be used as an organic electroluminescent layer material of an organic electroluminescent device.

A third aspect of the present invention provides an electronic device, which includes the device provided in the second aspect of the present invention.

For example, as shown in FIG. 1, the organic electroluminescent device may include an anode 1 and a cathode 2 arranged oppositely, and a functional layer 3 arranged between the anode 1 and the cathode 2; the functional layer 3 contains the Organic compounds. The functional layer 3 includes a hole injection layer 31, a hole transport layer 32, an electron blocking layer 33, an organic electroluminescence layer 34, an electron transport layer 35, and an electron injection layer 36. The compound provided by the present invention can be applied to the organic electroluminescence layer of an organic electroluminescence device, which can effectively increase the service life and luminous efficiency of the organic electroluminescence device, and reduce the driving voltage.

In the present invention, the anode 1 contains an anode material, and the anode material 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 SnO ₂ : 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, the anode 1 includes a transparent electrode containing indium tin oxide (ITO) as the anode.

Optionally, the hole transport layer 32 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.

Optionally, the electron blocking layer 33 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 the present application.

Optionally, the organic electroluminescent layer 34 is composed of a host material and a guest material, and the organic compound of the present invention can be used as the host material. The holes injected into the organic electroluminescent layer 34 and the electrons injected into the organic electroluminescent layer 34 can recombine in the organic electroluminescent layer 34 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest. Material, which in turn enables the guest material to emit light.

In a specific embodiment of the present application, the host material may be composed of the organic compound of the present invention, which can simultaneously transport electrons and holes, and can balance the transport efficiency of holes and electrons, so electrons and holes can be Efficient recombination in the organic electroluminescent layer improves the luminous efficiency of the organic electroluminescent device.

In another specific embodiment of the present invention, the host material may be a composite material, for example, it may include the organic compound of the present invention and the host material of the electronic organic electroluminescent layer. The organic compound of the present invention can effectively transport holes, so that the hole transport efficiency is balanced with the electron transport efficiency of the organic electroluminescent layer, so that electrons and holes can be efficiently recombined in the organic electroluminescent layer, thereby improving the Luminous efficiency of electroluminescent devices. For example, the host material may include the organic compound of the present invention and GH-n1, but it is not limited to this example.

In the present invention, the guest material of the organic electroluminescent layer 34 is well known to those skilled in the art, for example, it may be a compound with a condensed aryl group or its derivative, a compound with a heteroaryl group or its derivative, Aromatic amine derivatives or other materials are not particularly limited in the present invention. In an embodiment of the present application, the guest material of the organic electroluminescent layer 34 may be Ir(ppy) ₃ .

Optionally, the cathode 2 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, LiO ₂ /Al, LiF/Ca, LiF/Al, and BaF ₂ /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 31 may be further provided between the anode 1 and the hole transport layer 32 to enhance the ability to inject holes into the hole transport layer 32. The hole injection layer 31 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in the present invention. In an embodiment of the present invention, the hole injection layer 31 may be composed of HAT-CN.

Optionally, as shown in FIG. 1, an electron injection layer 36 may also be provided between the cathode 2 and the electron transport layer 35 to enhance the ability to inject electrons into the electron transport layer 35. The electron injection layer 36 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic substances. In a specific embodiment of the present invention, the electron injection layer 36 may include ytterbium (Yb).

Optionally, a hole blocking layer 30 may also be provided between the organic electroluminescent layer 34 and the electron transport layer 35.

The embodiment of the present invention also provides an electronic device 4 as shown in FIG. 2, and the electronic device 4 includes any one of the electronic components described in the above-mentioned electronic component embodiments. Since the electronic device 4 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. The electronic device 4 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. Based on the excellent characteristics of the organic compound of the present invention, the organic electroluminescent device of the present invention has higher luminous efficiency and longer service life, and lower driving voltage.

Example

The following examples are used to further illustrate the present invention, but the present invention is not limited in any way.

Those skilled in the art will recognize that the chemical reactions described in the present invention can be used to appropriately prepare many other compounds of the present invention, and other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. Inside. For example, the synthesis of non-exemplified compounds according to the present invention can be successfully completed by those skilled in the art through modification methods, such as appropriate protection of interfering groups, by using other known reagents in addition to those described in the present invention, or The reaction conditions are modified regularly. In addition, the reaction applied for in the present invention or the known reaction conditions are also recognized to be applicable to the preparation of other compounds of the present invention.

In the examples described below, all temperatures are set to degrees Celsius unless otherwise indicated. Reagents are purchased from commodity suppliers such as Aldrich Chemical Company, Arco Chemical Company and Alfa Chemical Company, and are used without further purification unless otherwise indicated. General reagents are purchased from 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 Factory. The raw materials come from commercial purchases, and suppliers such as Henan Chuangan Optoelectronics Technology Co., Ltd. etc. The compounds of the synthesis method not mentioned in the present invention are all raw materials obtained through commercial channels.

The lower reaction is generally under a positive pressure of nitrogen or argon or a drying tube on an anhydrous solvent (unless otherwise indicated), the reaction flask is plugged with a suitable rubber stopper, and the substrate is injected through a syringe. The glassware is all dried.

The chromatographic column is a silica gel 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% (CH3CN containing 0.1% formic acid) in (H2O containing 0.1% formic acid), using electrospray ionization (ESI), and UV detection at 210nm/254nm.

Proton nuclear magnetic resonance spectrum: Bruker 400MHz nuclear magnetic instrument, at room temperature, with CD ₂ Cl ₂ , CDCl ₃ or DMSO-d ₆ as solvent (in ppm), and TMS (0 ppm) as the reference standard. When multiple peaks appear, the following abbreviations will be used: s (singlet), d (doublet), t (triplet, triplet), m (multiplet, multiplet).

Synthesis Example 1 Synthesis of Intermediate 1A-X-I

The synthesis process of intermediate 1A-1-I:

Combine 3-bromo-6-chlorocarbazole (92g, 328mmol), 4-bromobiphenyl (87.8g, 377mmol), tris(dibenzylideneacetone) two palladium (3g, 3.28mmol), 2-dicyclohexyl Phosphorus-2',6'-dimethoxybiphenyl (2.72g, 6.56mmol) and sodium tert-butoxide (47.3g, 492mmol) were added to toluene (720mL), heated to 108°C under nitrogen protection, and stirred for 3h; Then it was cooled to room temperature, the reaction solution was washed with water and dried by adding magnesium sulfate. After filtration, the filtrate was filtered to remove the solvent under reduced pressure; the crude product was purified by recrystallization using a toluene system to obtain a white solid intermediate 1A-1-I (106g, yield 75 %).

According to the synthesis method of intermediate 1A-1-I, and using raw material 1 shown in Table 1 instead of 3-bromo-6-chlorocarbazole, and raw material 2 instead of 4-bromobiphenyl to prepare intermediate 1A-3-I, 1A-5-I, 1A-12-I, 1A-13-I, 1A-50-I, 1A-52-I, 1A-77-I, 1A-79-I, 1A-102-I, 1A- 103-I, 1A-143-I, 1A-164-I, 1A-166-I, 1A-219-I, 1A-222-I, 1A-257-I, 1A-267-I.

Among them, the intermediates 1A-3-I, 1A-5-I, 1A-12-I, 1A-13-I, 1A-50-I, 1A-52-I, 1A-77-I, 1A-79- I, 1A-102-I, 1A-103-I, 1A-143-I, 1A-164-I, 1A-166-I, 1A-219-I, 1A-222-I, 1A-257-I, The structure of 1A-267-I, raw material 1 and raw material 2, synthesis yield of the last step are shown in Table 1:

Table 1: Intermediate 1A-X-I structure, preparation and synthesis yield

Synthesis Example 2 Synthesis of Intermediate 1A-X-II

The synthesis process of intermediate 1A-1-II:

Intermediate 1A-1-I (28g, 63.7mmol) was dissolved in tetrahydrofuran (57mL), and under nitrogen protection at 0°C, the magnesium bar (1.9g, 76.2mmol) and 1,2-di After the addition of bromoethane (0.1g) in tetrahydrofuran (20mL), the reaction was naturally warmed to room temperature and kept stirring for 3h; the reaction solution was transferred to another container to remove residual magnesium sticks, and tetrahydrofuran was removed under reduced pressure , The solid was diluted with dichloromethane (30mL); then under the protection of nitrogen at room temperature, slowly dropwise add 1-bromoadamantane (13.7g, 63.7mmol) in dichloromethane (50mL) solution, heated to reflux, Keep stirring for 2h; after cooling, pour the reaction solution into 2mol/L hydrochloric acid, separate the organic phase, and extract the aqueous phase with n-heptane; wash the combined organic phase with anhydrous magnesium sulfate, dry, filter, and remove the solvent under reduced pressure ; With n-heptane as the mobile phase, the crude product was purified by silica gel column chromatography (eluent: DCM: n-heptane (v/v, 1:3)) to obtain intermediate 1A-1-II as colorless The oily substance is 18 g, and the yield is 58%.

According to the synthesis method of Intermediate 1A-1-II, and using Intermediate 1A-XI shown in Table 2 instead of 1A-1-I to prepare Intermediate 1A-3-II, 1A-5-II, 1A-12- II, 1A-13-II, 1A-50-II, 1A-52-II, 1A-77-II, 1A-79-II, 1A-102-II, 1A-103-II, 1A-143-II, 1A-164-II, 1A-166-II, 1A-219II, 1A-222-II, 1A-257-II, 1A-267-II.

Among them, the intermediates 1A-3-II, 1A-5-II, 1A-12-II, 1A-13-II, 1A-50-II, 1A-52-II, 1A-77-II, 1A-79- II, 1A-102-II, 1A-103-II, 1A-143-II, 1A-164-II, 1A-166-II, 1A-219II, 1A-222-II, 1A-257-II, 1A- The structure of 267-II, the 1A-XI used in the synthesis, and the synthesis yield of the last step are shown in Table 2:

Table 2: Intermediate 1A-X-II structure, preparation and synthesis yield

Synthesis Example 3 Synthesis of Intermediate 1A-X

The synthesis process of intermediate 1A-1:

Intermediate 1A-1-II (9.8g, 20.1mmol), pinacol diborate (6.12g, 24.1mmol), tris(dibenzylideneacetone) two palladium (0.1839g, 0.201mmol), 2- Dicyclohexylphosphorus-2',4',6'-triisopropylbiphenyl (0.1920g, 0.402mmol) and potassium acetate (2.95g, 30.15mmol) are added to 1,4-dioxane (90mL) , Heated to 80°C under the protection of nitrogen, stirred for 3h; then cooled to room temperature, the reaction solution was washed with water and dried by adding magnesium sulfate. After filtration, the filtrate was decompressed to remove the solvent; the crude product was recrystallized and purified using a toluene system to obtain Intermediate 1A -1 is a white solid (9.2g, yield 80%).

According to the synthesis method of Intermediate 1A-1, and using Intermediate 1A-X-II shown in Table 3 instead of 1A-1-II to prepare Intermediate 1A-3, 1A-5, 1A-12, 1A-13, 1A -50, 1A-52, 1A-77, 1A-79, 1A-102, 1A-103, 1A-143, 1A-164, 1A-166, 1A-219, 1A-222, 1A-257, 1A-267 .

Among them, intermediates 1A-3, 1A-5, 1A-12, 1A-13, 1A-50, 1A-52, 1A-77, 1A-79, 1A-102, 1A-103, 1A-143, 1A- The structure of 164, 1A-166, 1A-219, 1A-222, 1A-257, and 1A-267, the synthesis using intermediate 1A-X-II, and the synthesis yield of the last step are shown in Table 3:

Table 3: Intermediate 1A-X structure, preparation and synthesis yield

Synthesis Example 4 Synthesis of Intermediate 2A-X

The synthesis process of intermediate 2A-1:

Combine 3-bromo-carbazole (8.1g, 32.8mmol), 4-bromobiphenyl (8.78g, 37.7mmol), tris(dibenzylideneacetone) two palladium (0.3g, 0.328mmol), 2-bicyclic Hexylphosphorus-2',6'-dimethoxybiphenyl (0.272g, 0.656mmol) and sodium tert-butoxide (4.73g, 49.2mmol) were added to toluene (72mL), heated to 108°C under nitrogen protection, and stirred 3h; then cooled to room temperature, the reaction solution was washed with water and then dried with magnesium sulfate, filtered and the filtrate was filtered to remove the solvent under reduced pressure; the crude product was recrystallized and purified using a toluene system to obtain Intermediate 2A-1 as a white solid (10.4g, product Rate 80%).

Refer to the synthesis method of intermediate 2A-1, and use raw material 1 in Table 4 instead of 3-bromocarbazole, and raw material 2 instead of 4-bromobiphenyl to prepare intermediate 2A-3, 2A-5, 2A-12, 2A- 13, 2A-50, 2A-52, 2A-77, 2A-79, 2A-102, 2A-103, 2A-143, 2A-164, 2A-166, 2A-219, 2A-222, 2A-257, 2A-267.

Among them, the intermediates 2A-3, 2A-5, 2A-12, 2A-13, 2A-50, 2A-52, 2A-77, 2A-79, 2A-102, 2A-103, 2A-143, 2A- 164, 2A-166, 2A-219, 2A-222, 2A-257, 2A-267, 2A-302, 2A-307, 2A-314 structure, raw material 1 and raw material 2, the last step of synthesis product The rate is shown in Table 4:

Table 4: Intermediate 2A-X structure, preparation and synthesis yield

Synthesis Example 5 Synthesis of compound PX

Synthesis of compound P1:

Intermediate 1A-1 (11.5g, 20mmol), intermediate 2A-1 (7.96g, 20mmol), palladium acetate (0.0448g, 0.2mmol), 2-dicyclohexylphosphorus-2', 4', 6' -Triisopropylbiphenyl (0.19g, 0.4mmol) and potassium carbonate (4.14g, 30mmol) were added to toluene (80mL), absolute ethanol (40mL) and deionized water (20mL), heated to 80 under nitrogen protection ℃, stirring for 2h; then cooling to room temperature, the reaction solution was washed with water and then dried by adding magnesium sulfate, filtered and the filtrate was reduced under reduced pressure to remove the solvent; the crude product was purified by recrystallization using the dichloromethane/n-heptane system to obtain compound P1 as white Solid (10.5 g, 68% yield). LC-MS (ESI, pos.ion) m/z: 771.37 [M+H] ⁺ .

The organic compounds P3, P5, P12, P13, P50, P52, P77, P79 were prepared according to the synthetic method of compound P1, and using intermediate 1A-X instead of intermediate 1A-1, and intermediate 2A-X instead of intermediate 2A-1. , P102, P103, P143, P164, P166, P219, P222, P257, P267.

Among them, the structure of P3, P5, P12, P13, P50, P52, P77, P79, P102, P103, P143, P164, P166, P219, P222, P257, P267, the raw materials used in the synthesis, the synthesis yield and characterization of the last step The data is shown in Table 5:

Table 5: Compound PX structure, preparation, synthesis yield and characterization data

Synthesis Example 6 Synthesis of Intermediates 1B-17-I, 1B-65-I and 1B-291-I

The synthesis process of intermediate 1B-17-I:

Dissolve 4-bromo-4chlorobiphenyl (18.9g, 63.7mmol) in tetrahydrofuran (57mL), and slowly drop them into the place where magnesium bars (1.9g, 76.2mmol) and 1,2 are placed under nitrogen protection at 0°C. -Dibromoethane (0.1g) in tetrahydrofuran (20mL) solution, after the dropwise addition, the reaction naturally warms to room temperature and keeps stirring for 3h; the reaction solution is transferred to another container to remove residual magnesium bars, under reduced pressure The tetrahydrofuran was removed, and the solid was diluted by adding dichloromethane (20mL); then, under room temperature and nitrogen protection, a solution of 1-bromoadamantane (13.7g, 63.7mmol) in dichloromethane (50mL) was slowly added dropwise and heated to Reflux and keep stirring for 2h; after cooling, pour the reaction solution into 2mol/L hydrochloric acid (TC), separate the organic phase, and extract the aqueous phase with n-heptane; wash the combined organic phase with water and use magnesium sulfate to dry, filter, and reduce The solvent was removed under pressure; the crude product was purified by silica gel column chromatography with n-heptane as the mobile phase to obtain 12 g of intermediate 1B-17-I as a colorless oil with a yield of 60%.

Refer to the synthesis method of intermediate 1B-17-I, and use 2-bromo-7-chlorodimethylfluorene shown in Table 6 instead of 4-bromo-4chlorobiphenyl to prepare intermediate 1B-65-I, using 4 -Chlorobromobenzene replaces 4-bromo-4chlorobiphenyl to prepare intermediate 1B-291-I. Among them, the number, structure, raw materials, synthesis yield of the last step, etc. of the intermediates 1B-65-I and 1B-291-I are shown in Table 6:

Table 6: Structure, preparation and synthesis yield of intermediates 1B-65-I and 1B-291-I

Synthesis Example 7 Synthesis of Intermediates 1B-17-II, 1B-65-II and B-291-II

The synthesis process of intermediate 1B-17-II:

Combine 3-chlorocarbazole (6.5g, 32.8mmol), intermediate 1B-17-I (12g, 37.7mmol), tris(dibenzylideneacetone) two palladium (0.3g, 0.328mmol), 2-bicyclic Hexylphosphorus-2',6'-dimethoxybiphenyl (0.272g, 0.656mmol) and sodium tert-butoxide (4.73g, 49.2mmol) were added to toluene (100mL), heated to 108°C under nitrogen protection, and stirred 3h; then cooled to room temperature, the reaction solution was washed with water and then dried by adding magnesium sulfate, filtered and the filtrate was filtered to remove the solvent under reduced pressure; the crude product was recrystallized and purified using a toluene system to obtain Intermediate 1B-17-II as a white solid (12g, The yield is 75%).

Refer to the synthesis method of Intermediate 1B-17-II, and use Intermediate 1B-XI shown in Table 7 instead of Intermediate 1B-17-I to prepare Intermediates 1B-65-II and B-291-II. Table 7 shows the structure, raw materials, and synthesis yield of the last step of body 1B-65-II and 1B-291-II:

Table 7: Intermediate 1B-65-II, 1B-291-II structure, preparation and synthesis yield

Synthesis Example 8 Synthesis of Intermediates 1B-17, 1B-65 and 1B-291

The synthesis process of intermediate 1B-17:

Intermediate 1B-17-II (9.8g, 20.1mmol), pinacol diborate (6.12g, 24.1mmol), tris(dibenzylideneacetone) two palladium (0.1839g, 0.201mmol), 2- Dicyclohexylphosphorus-2',4',6'-triisopropylbiphenyl (0.1920g, 0.402mmol) and potassium acetate (2.95g, 30.15mmol) were added to 1,4-dioxane (90mL) , Heated to 80°C under nitrogen protection, stirred for 3h; then cooled to room temperature, the reaction solution was washed with water and dried by adding magnesium sulfate, filtered and the filtrate was decompressed to remove the solvent; the crude product was recrystallized and purified using a toluene system to obtain Intermediate 1B -17 is a white solid (9.2g, yield 80%).

Refer to the synthesis method of Intermediate 1B-17, and use Intermediate 1B-X-II shown in Table 8 instead of Intermediate 1B-17-II to prepare Intermediate 1B-65 and 1B-291, wherein Intermediate 1B-65 , 1B-291's structure, raw materials, and the synthesis yield of the last step are shown in Table 8:

Table 8: Intermediate 1B-65, 1B-291 structure, preparation and synthesis yield

Synthesis Example 9 Synthesis of Intermediates 2B-17, 2B-65 and 2B-291

The synthesis process of intermediate 2B-17:

Combine 3-bromo-carbazole (8.1g, 32.8mmol), 1-bromo-4phenylnaphthalene (10.6g, 37.7mmol), tris(dibenzylideneacetone) two palladium (0.3g, 0.328mmol), 2 -Dicyclohexylphosphorus-2',6'-dimethoxybiphenyl (0.272g, 0.656mmol) and sodium tert-butoxide (4.73g, 49.2mmol) were added to toluene (72mL) and heated to 108 under nitrogen ℃, stirred for 3h; then cooled to room temperature, the reaction solution was washed with water and then dried by adding magnesium sulfate, filtered and the filtrate was reduced under reduced pressure to remove the solvent; the crude product was recrystallized and purified using a toluene system to obtain a white solid intermediate 2B-17 (11.6g , Yield 79%).

Refer to the synthesis method of intermediate 2B-17, and use raw material 1 in Table 9 instead of 1-bromo-4phenylnaphthalene to prepare intermediates 2B-65 and 2B-291, wherein the intermediates 2B-65 and 2B-291 are The structure, raw materials, and the synthesis yield of the last step are shown in Table 9:

Table 9: Intermediate 2B-65, 2B-291 structure, preparation and synthesis yield

Synthesis Example 10 Synthesis of compounds P17, P65 and P291

Synthesis of compound P17:

Intermediate 1B-17 (11.5g, 20mmol), intermediate 2B-17 (8.96g, 20mmol), palladium acetate (0.0448g, 0.2mmol), 2-dicyclohexylphosphorus-2', 4', 6' -Triisopropyl biphenyl (0.19g, 0.4mmol) and potassium carbonate (4.14g, 30mmol) were added to toluene (80mL), absolute ethanol (40mL) and deionized water (20mL), heated to 80 under nitrogen protection ℃, stirring for 2h; then cooling to room temperature, the reaction solution was washed with water and then dried with magnesium sulfate, filtered and the filtrate was reduced under reduced pressure to remove the solvent; the crude product was recrystallized and purified using the dichloromethane/n-heptane system to obtain compound P17 as white Solid (11.1 g, 68% yield). LC-MS (ESI, pos.ion) m/z: 821.38 [M+H] ⁺ .

Refer to the synthesis method of compound P17, and use intermediate 1B-X shown in Table 10 instead of intermediate 1B-17, and intermediate 2B-X instead of intermediate 2B-17 to prepare compounds P65 and P291. Among them, the structure, raw material, synthesis yield and characterization data of the last step of compound P65 and P291 are shown in Table 10.

Table 10: Compound P65, P291 structure, preparation, synthesis yield and characterization data

Synthesis Example 11 Synthesis of Intermediates 1C-247-I and 1C-249-I

The synthesis process of intermediate 1C-247-I:

Dissolve p-bromochlorobenzene (12g, 63.7mmol) in tetrahydrofuran (57mL), slowly drop the magnesium bar (1.9g, 76.2mmol) and 1,2-dibromoethane under nitrogen protection at 0℃. (0.1g) in tetrahydrofuran (20mL) solution, after the addition is complete, the reaction naturally rises to room temperature and keeps stirring for 3h; the reaction solution is transferred to another container to remove residual magnesium bars, and tetrahydrofuran is removed under reduced pressure. Add dichloromethane (30mL) to dilute; then slowly add 1-bromoadamantane (13.7g, 63.7mmol) in dichloromethane (50mL) solution dropwise at room temperature and under nitrogen protection, heat to reflux and keep stirring 2h; After cooling, pour the reaction solution into 2mol/L hydrochloric acid (TC), separate the organic phase, and extract the aqueous phase with n-heptane; wash the combined organic phase with water, dry it with magnesium sulfate, filter, and remove the solvent under reduced pressure; Using n-heptane as the mobile phase, the crude product was purified by silica gel column chromatography to obtain 18 g of intermediate 1C-247-I as a colorless oil, with a yield of 58%.

Referring to the synthesis method of intermediate 1C-247-I, and using raw material 1 shown in Table 11 instead of p-bromochlorobenzene, intermediate 1C-249-I was prepared. Among them, the structure of intermediate 1C-249-I, raw materials, and the synthesis yield of the last step are shown in Table 11:

Table 11: Intermediate 1C-249-I structure, preparation and synthesis yield

Synthesis Example 12 Synthesis of Intermediates 1C-247-II and 1C-249-II

The synthesis process of intermediate 1C-247-II:

Combine 3-bromo-6-chlorocarbazole (5.6g, 20.1mmol), pinacol diborate (6.12g, 24.1mmol), tris(dibenzylideneacetone) dipalladium (0.1839g, 0.201mmol), 2-Dicyclohexylphosphorus-2',4',6'-triisopropylbiphenyl (0.1920g, 0.402mmol) and potassium acetate (2.95g, 30.15mmol) add 1,4-dioxane (90mL ), heated to 80°C under the protection of nitrogen, and stirred for 3 hours; then cooled to room temperature, the reaction solution was washed with water and then dried by adding magnesium sulfate, filtered, and the filtrate was decompressed to remove the solvent; the crude product was purified by recrystallization using a toluene system to obtain the intermediate Body 1C-247-II was a white solid (5.3 g, yield 80%).

Referring to the synthesis method of intermediate 1C-247-II, intermediate 1C-249-II was prepared with the same raw materials. Among them, the structure of intermediate 1C-249-II and the synthesis yield of the last step are shown in Table 12:

Table 12: Intermediate 1C-249-II structure, preparation and synthesis yield

Synthesis Example 13 Synthesis of Intermediates 1C-247-III and 1C-249-III

The synthesis process of intermediate 1C-247-III:

Intermediate 1C-247-II (6.54g, 20mmol), intermediate 1C-247-I (4.92g, 20mmol), palladium acetate (0.0448g, 0.2mmol), 2-dicyclohexylphosphorus-2',4 ',6'-Triisopropylbiphenyl (0.19g, 0.4mmol) and potassium carbonate (4.14g, 30mmol) were added to toluene (80mL), absolute ethanol (40mL) and deionized water (20mL) under nitrogen protection After heating to 80°C and stirring for 2h; then cooling to room temperature, the reaction solution was washed with water and then dried with magnesium sulfate. After filtration, the filtrate was decompressed to remove the solvent; the crude product was purified by recrystallization using the dichloromethane/n-heptane system to obtain Intermediate 1C-247-III is a white solid (5.8 g, yield 70%).

Referring to the synthesis method of intermediate 1C-247-III, and using raw material 1 shown in Table 13 instead of intermediate 1C-247-I, intermediate 1C-249-III was prepared. Among them, the structure of intermediate 1C-249-III, raw materials, and the synthesis yield of the last step are shown in Table 13:

Table 13: Intermediate 1C-249-III structure, preparation and synthesis yield

Synthesis Example 14 Synthesis of Intermediates 1C-247-IV and 1C-249-IV

The synthesis process of intermediate 1C-247-IV:

Combine 4-bromobiphenyl (7.64g, 32.8mmol), 1C-247-III (15.5g, 37.7mmol), tris(dibenzylideneacetone) two palladium (0.3g, 0.328mmol), 2-dicyclohexyl Phosphorus-2',6'-dimethoxybiphenyl (0.272g, 0.656mmol) and sodium tert-butoxide (4.73g, 49.2mmol) were added to toluene (72mL), heated to 108°C under nitrogen protection, and stirred for 3h ; Then cooled to room temperature, the reaction solution was washed with water and then dried by adding magnesium sulfate, filtered and the filtrate was decompressed to remove the solvent; the crude product was recrystallized and purified using a toluene system to obtain a white solid intermediate 1C-247-IV (12.9g, product Rate 75%).

Referring to the synthesis method of intermediate 1C-247-IV, and using raw material 1 shown in Table 14 instead of intermediate 1C-247-III, intermediate 1C-249-IV was prepared. Among them, the structure of intermediate 1C-249-IV, the raw materials, and the synthesis yield of the last step are shown in Table 14:

Table 14: Intermediate 1C-249-IV structure, preparation and synthesis yield

Synthesis Example 15 Synthesis of Intermediates 1C-247 and 1C-249

The synthesis process of intermediate 1C-247:

Intermediate 1C-247-IV (11.28g, 20.1mmol), pinacol diboronic acid ester (6.12g, 24.1mmol), tris(dibenzylideneacetone) two palladium (0.1839g, 0.201mmol), 2- Dicyclohexylphosphorus-2',4',6'-triisopropylbiphenyl (0.1920g, 0.402mmol) and potassium acetate (2.95g, 30.15mmol) were added to 1,4-dioxane (90mL) , Heated to 80°C under the protection of nitrogen, stirred for 3h; then cooled to room temperature, the reaction solution was washed with water and dried by adding magnesium sulfate, filtered and the filtrate was decompressed to remove the solvent; the crude product was recrystallized and purified using a toluene system to obtain Intermediate 1C -247 is a white solid (10.2g, yield 78%).

Referring to the synthesis method of intermediate 1C-247, and using raw material 1 shown in Table 15 instead of intermediate 1C-247-IV, intermediate 1C-249 was prepared. Among them, the structure of intermediate 1C-249, synthesis materials, and the synthesis yield of the last step are shown in Table 15:

Table 15: Structure, preparation and synthesis yield of intermediate 1C-249

Synthesis Example 16 Synthesis of Intermediate 2C-247

The synthesis process of intermediate 2C-247:

Combine 3-bromo-carbazole (8.1g, 32.8mmol), 3-bromo-dibenzofuran (9.3g, 37.7mmol), tris(dibenzylideneacetone) dipalladium (0.3g, 0.328mmol), 2 -Dicyclohexylphosphorus-2',6'-dimethoxybiphenyl (0.272g, 0.656mmol) and sodium tert-butoxide (4.73g, 49.2mmol) were added to toluene (72mL) and heated to 108 under nitrogen ℃, stirred for 3h; then cooled to room temperature, the reaction solution was washed with water and then dried by adding magnesium sulfate, filtered, and the filtrate was reduced under reduced pressure to remove the solvent; the crude product was recrystallized and purified using a toluene system to obtain Intermediate 2C-247 as a white solid (10g , The yield is 74%).

Synthesis Example 16 Synthesis of Compounds P247 and P249

Synthesis of compound P247:

Intermediate 1C-247 (13.1g, 20mmol), intermediate 2C-247 (8.24g, 20mmol), palladium acetate (0.0448g, 0.2mmol), 2-dicyclohexylphosphorus-2', 4', 6' -Triisopropylbiphenyl (0.19g, 0.4mmol) and potassium carbonate (4.14g, 30mmol) were added to toluene (80mL), absolute ethanol (40mL) and deionized water (20mL), heated to 80 under nitrogen protection ℃, stirring for 2h; then cooling to room temperature, the reaction solution was washed with water and then dried by adding magnesium sulfate, filtered and the filtrate was reduced under reduced pressure to remove the solvent; the crude product was purified by recrystallization using dichloromethane/n-heptane system to obtain compound P247 as white Solid (11.2 g, 65% yield). LC-MS (ESI, pos.ion) m/z: 861.38 [M+H] ⁺ .

Referring to the synthesis method of compound P247, and using intermediate 1C-249 instead of intermediate 1C-247, compound P249 was prepared. Among them, the structure of compound P249, synthetic raw materials, synthesis yield and characterization data of the last step are shown in Table 16:

Table 16: Structure, preparation, synthesis yield and characterization data of compound P249

The NMR data of some compounds are shown in Table 17 below

Organic electroluminescent device preparation

Example 1

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

The ITO substrate (manufactured by Corning) was cut into a size of 40mm×40mm×0.7mm. The photolithography process was used to prepare an experimental substrate with cathode, anode, and insulating layer patterns, using ultraviolet ozone and O ₂ :N ₂ plasma. Surface treatment to increase the work function of the anode (experimental substrate) and remove scum. It should be noted that the ITO substrate can also be cut into other sizes according to actual needs, and the size of the ITO substrate in the present disclosure is not specifically limited here.

F4-TCNQ was vacuum-evaporated on the experimental substrate (anode) to form a thickness of

The hole injection layer (HIL), and NPB is vapor-deposited on the hole injection layer to form a thickness of

The first hole transport layer.

PAPB was vacuum-evaporated on the first hole transport layer to form a thickness of

The second hole transport layer.

On the second hole transport layer, the compound P1:GH-n1:Ir(ppy) ₃ was co-evaporated at a ratio of 66%:33%:6% to form a thickness of

The green light-emitting layer (EML).

ET-06 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form

Thick electron transport layer (ETL), LiQ 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 a deposition rate of 1:9, and then vacuum deposited on the electron injection layer to form a thickness of

The cathode.

In addition, the vapor deposition thickness on the above cathode is

CP-05 to form an organic covering layer (CPL) to complete the manufacture of organic light-emitting devices. The structure is shown in Figure 1.

Example 2-Example 23

Except that the organic compound shown in Table 18 was used instead of Compound P1 when forming the light-emitting layer, an organic electroluminescence device was produced in the same manner as in Example 1.

Example 24

In Example 1, only when the organic electroluminescence layer was formed, the material of the light-emitting layer was changed, and the compound P1:GH-n1:Ir(ppy) ₃ in Example 1 was adjusted to 66%:33%:6% The ratio of (evaporation rate) is changed to GH-n2: compound P302: Ir(ppy) ₃ by the ratio of 66%:33%:6% (evaporation rate) for common vapor deposition to form a thickness of

The green organic electroluminescent layer (EML). The other parts of the device have not been changed.

Example 25-Example 26

When forming the organic electroluminescence layer, the compound shown in the compound Y column in Table 18 was substituted for the compound P302 in Example 24, and the organic electroluminescence device was fabricated by the same method as in Example 24.

Comparative example 1

An organic electroluminescence device was produced in the same manner as in Example 1, except that Compound A shown in Table 17 below replaced Compound P1 when forming the light-emitting layer.

Comparative example 2

An organic electroluminescence device was produced in the same manner as in Example 1, except that Compound B shown in Table 17 below replaced Compound P1 when forming the light-emitting layer.

Comparative example 3

An organic electroluminescence device was produced in the same manner as in Example 1, except that Compound C shown in Table 17 below replaced Compound P1 when forming the light-emitting layer.

Comparative example 4

Referring to Table 17, the compound P302 in Example 24 was replaced with compound D, and the organic electroluminescence device was prepared according to the same method as in Example 24. It can be understood that in the organic electroluminescent layer of the prepared organic electroluminescent device, GH-n2: compound D: Ir(ppy) ₃ =66%:33%:6%.

Comparative example 5

An organic electroluminescent device was produced in the same manner as in Example 24, except that Compound E shown in Table 17 below replaced Compound P302 when forming the light-emitting layer.

The material structures used in the above embodiments and comparative examples are as follows:

For the organic electroluminescence device prepared as above, the performance of the device was analyzed under the condition of ^{20 mA/cm 2 and the results are shown in Table 18 below:}

Table 18:

It can be seen from Table 18 that Examples 1-26 of the compound as the luminescent host material are compared with Comparative Example 1, Comparative Example 2, Comparative Example 3, and Comparative Example using the well-known Compound A, Compound B, Compound C, Compound D, and Compound E. Compared with Example 4 and Comparative Example 5, the organic compound used in the present invention is used as the host material of the light-emitting layer. ) Is increased by at least 13.3%, the external quantum efficiency is increased by at least 8.7%, the life span is increased by at least 15.35%, and the maximum life span can be increased by 90 hours. In the examples, the performances of the devices prepared by the compound P1 used in Example 1 are better than those of other types of compounds.

Compound thermal stability test

When the compound is used for mass production of devices, it needs to be heated for a long time under evaporation conditions. If the thermal stability of the molecular structure of the compound is poor under heated conditions, the purity of the compound will decrease under long-term heating conditions, resulting in large differences in the performance of devices prepared before, during, and after mass production.

The present invention uses the following methods to evaluate the stability of the molecular structure of the compound of the present invention under long-term heating during mass production evaporation:

In a high vacuum environment (<10 ^-6 Pa), and

At the temperature corresponding to the vapor deposition rate per second, for compounds P1, P3, P5, P12, P13, P17, P50, P52, P65, P77, P79, P102, P103, P143, P164, P166, P219, P222, P247 , P249, P257, P267, P291, P302, P307, P314 and comparative compound F were respectively subjected to 200 hours heat resistance test (heat preservation treatment). The stability of the compound of the present disclosure under mass production conditions is judged by the purity drop value before and after the heat resistance experiment.

Comparative compound F:

Table 19 Test temperature and purity drop value of organic compounds

It can be seen from Table 19 that the purity reduction values of the organic compounds of the present disclosure are all less than 0.6%, and most of them are less than 0.3%. In the comparative example, the decrease in purity exceeds 1%. When the purity of the compound material decreases by more than 1%, the efficiency and life of the device will be significantly reduced; therefore, the use of such thermally unstable compounds in actual mass production will result in poor performance of the devices prepared before, during, and after mass production. Big difference. In the present invention, the heat resistance experiment of the compound confirms that the purity drop value is less than 0.6%. The comparative compound has a purity drop of 2.1% at 225°C, which is more than 1%. Therefore, the organic compound of the present disclosure also has excellent thermal stability for mass production. .

The preferred embodiments of the present invention are described in detail above with reference to the accompanying drawings. However, the present invention is not limited to the specific details in the above-mentioned embodiments. Within the scope of the technical concept of the present invention, many simple modifications can be made to the technical solutions of the present invention. These simple modifications all belong to the protection scope of the present invention.

In addition, it should be noted that the various specific technical features described in the above-mentioned specific embodiments can be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, the present invention is The combination method will not be explained separately.

In addition, various different embodiments of the present invention can also be combined arbitrarily, as long as they do not violate the idea of the present invention, they should also be regarded as the disclosed content of the present invention.

Claims (20)

1. An organic compound, wherein the compound has a structure represented by the following formula (1), formula (2) or formula (3):

   

   Wherein, Ar ₁ and Ar _{2 are the} same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

   Each R _t is

   

   Wherein, L is selected from single bond, substituted or unsubstituted arylene group having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene group having 4 to 30 carbon atoms; Ad is substituted or unsubstituted Adamantyl

   p, q, i, s, v, and m each independently represent the _{number of each substituent R t} , wherein p, q, i, s, v, and m are independently 0, 1, 2, 3, or 4, respectively, And p+q is 1, 2, 3 or 4, when p+q is 2, 3 or 4, each R _{t is the} same or different; i+s is 0, 1, 2 or 3, when i+s is 2 Or when 3, each R _{t is the} same or different;

   v+m is 0, 1, or 2. When v+m is 2, each R _{t is the} same or different;

   n ₁ represents the number of substituents R _{1 , n 2} represents the number of substituents R ₂ , n ₁ and n _{2 are the} same or different, and are independently selected from 0, 1, 2, 3, 4 or 5; when When n _{1 is} greater than 1, any two of R _{1 are the} same or different, and when n _{2 is} greater than 1, any two of R _{2 are the} same or different;

   The substituent in Ar ₁ , the substituent in Ar ₂ , the substituent in L, the substituent on Ad, R ₁ and R ₂ are the same or different from each other, and are independently selected from deuterium, fluorine, chlorine, Bromine, cyano, C1-C12 alkyl group, C2-C12 alkenyl group, C1-C12 alkoxy group, C1-C12 alkylthio group , A haloalkyl group with 1 to 12 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, a heterocycloalkyl group with 2 to 12 carbon atoms, an alkylamino group with 1 to 12 carbon atoms, any An aryl group having 6 to 20 carbon atoms and 6 to 18 carbon atoms optionally substituted with 0, 1, 2 or 3 substituents selected from deuterium, fluorine, chlorine, bromine, cyano or alkyl Heteroaryl group, trialkylsilyl group with 3-12 carbon atoms, arylsilyl group with 6-18 carbon atoms, aryloxy group with 6-18 carbon atoms, 6 carbon atoms ～18 arylthio; or, in each of L, Ar ₁ and Ar ₂ , when there are two substituents on the same atom, optionally, the two substituents are connected to each other to be connected to them in common The atoms together form a 5- to 18-membered aliphatic ring or a 5- to 18-membered aromatic ring.
2. The organic compound according to claim 1, wherein the organic compound has a structure shown in any one of the following formulas (I-27) to (I-31):

   
3. The organic compound according to claim 1 or 2, wherein the R ₁ and the R ₂ are the same or different from each other, and are each independently selected from deuterium, fluorine, chlorine, bromine, cyano, and the number of carbon atoms is 1. ~4 alkyl groups, alkoxy groups having 1 to 4 carbon atoms, haloalkyl groups having 1 to 4 carbon atoms, trimethylsilyl groups having 3 to 9 carbon atoms, triphenylsilyl groups, Phenyl, naphthyl, quinoline, isoquinolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenyl-carbazolyl, pyridyl, cyclopropanyl, cyclopentyl , Cyclohexane, adamantyl group.
4. The organic compound according to any one of claims 1 to 3, wherein the L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and the number of substituted or unsubstituted carbon atoms 4-12 heteroarylene.
5. The organic compound according to any one of claims 1 to 4, wherein the L is selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted Terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted 9,9-dimethylfluorenylene, substituted or unsubstituted dibenzofuran subunit, substituted or unsubstituted diphenyl Thiophenylidene, substituted or unsubstituted quinolinylene, substituted or unsubstituted isoquinolinylene, substituted or unsubstituted carbazolylidene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted One of anthrylene, substituted or unsubstituted pyridylene, or a subunit group formed by connecting two or three of the above subunits through a single bond; the substituents in L are the same or different from each other, Each is independently selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trimethylsilyl , Phenyl, cyano-substituted phenyl, fluorine-substituted phenyl, naphthyl, quinoline, isoquinolyl, pyridyl, cyclopentyl, and cyclohexane group.
6. The organic compound according to any one of claims 1 to 5, wherein the L is selected from a single bond or the group consisting of the following structural formulas (j-1) to (j-14):

   

   

   Among them, M _{1 is} selected from a single bond or

   

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

   G ₆ to G ₁₃ are each independently selected from N or C(F ₂ ), and _{at least one of G 6} to G ₁₃ is selected from N; when _{two or more of G 6} to G ₁₃ are selected from C(F ₂ ) , Any two F _{2 are the} same or different;

   G ₁₄ to G ₂₃ are each independently selected from N or C(F ₃ ), and _{at least one of G 14} to G ₂₃ is selected from N; when _{two or more of G 14} to G ₂₃ are selected from C(F ₃ ) , Any two F _{3 are the} same or different;

   G ₂₄ to G ₃₃ are each independently selected from N or C(F ₄ ), and _{at least one of G 24} to G ₃₃ is selected from N; when _{two or more of G 24} to G ₃₃ are selected from C(F ₄ ) , Any two F _{4 are the} same or different;

   F ₁ to F ₄ and Z ₁ to Z ₁₅ are each independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl groups having 3 to 12 carbon atoms, and 1 to 10 carbon atoms The alkyl group, a haloalkyl group with 1-10 carbon atoms, a cycloalkyl group with 3-10 carbon atoms, an alkoxy group with 1-10 carbon atoms, and an alkylthio group with 1-10 carbon atoms , A heteroaryl group with 3 to 18 carbon atoms, or the number of carbon atoms optionally substituted with 0, 1, 2 or 3 substituents selected from deuterium, fluorine, chlorine, bromine, cyano, and alkyl Is an aryl group of 6-18;

   h ₁ ～h ₁₅ are represented by h _k , Z ₁ ～Z ₁₅ are represented by Z _k , k is a variable, which is an arbitrary integer from 1 to 15, and h _k is the number of substituents Z _{k . When h k is} greater than 1, The corresponding substituents Z _{k are the} same or different;

   Wherein, when k is selected from 1, 2, 3, 8, 9, 10, 11, 14, or 15, h _{k is} selected from 1, 2, 3, or 4;

   When k is selected from 4, h _{k is} selected from 1, 2 or 3;

   When k is selected from 5 or 6, h _{k is} selected from 1, 2, 3, 4, 5 or 6;

   When k is selected from 7, h _{k is} selected from 1, 2, 3, 4, 5, 6 or 7;

   When k is selected from 12 or 13, h _{k is} selected from 1, 2, 3, 4, 5, 6, 7 or 8;

   K _{1 is} selected from O, S, N (Z ₁₆ ), C (Z ₁₇ Z ₁₈ ), Si (Z ₁₇ Z ₁₈ ); wherein, each of Z ₁₆ , Z ₁₇ , and Z _{18 is} independently selected from hydrogen, carbon atom Heteroaryl groups having 3 to 18, alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, or optionally 0, 1, 2 or 3 selected from deuterium, fluorine The aryl group with 6-20 carbon atoms substituted by the substituents of, chlorine, bromine, cyano, or alkyl;

   Or, optionally, the above-mentioned Z ₁₇ and Z ₁₈ are connected to each other to form a 5- to 13-membered aliphatic ring or a 5- to 13-membered aromatic ring with the atoms they are commonly connected to;

   K _{2 is} selected from a single bond, O, S, N (Z ₁₉ ), C (Z ₂₀ Z ₂₁ ), Si (Z ₂₀ Z ₂₁ ); wherein each of Z ₁₉ , Z ₂₀ and Z _{21 is} independently selected from hydrogen , C6-C18 aryl group, C3-C18 heteroaryl group, C1-C10 alkyl group or C3-C10 cycloalkyl group, or any Optionally, the above-mentioned Z ₂₀ and Z ₂₁ are connected to each other to form a 5- to 13-membered aliphatic ring or a 5- to 13-membered aromatic ring with their common atoms.
7. The organic compound according to any one of claims 1 to 6, wherein the L is selected from a single bond, a substituted or unsubstituted group W ₁ , and the unsubstituted group W _{1 is} selected from the following groups :

   

   When the W ₁ group is substituted by one or more substituents, the substituents of W ₁ are each independently selected from deuterium, fluorine, chlorine, cyano, alkyl with 1 to 4 carbon atoms, and the number of carbon atoms Is an alkoxy group having 1 to 4, a haloalkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 9 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and the number of carbon atoms is A group consisting of 6-15 aryl groups and 3-12 heteroaryl groups; _{when the number of substituents on W 1} is more than one, the respective substituents are the same or different.
8. The organic compound according to any one of claims 1 to 7, wherein the L is a single bond or any one of the following groups:

   

   
9. The organic compound according to any one of claims 1 to 8, wherein the Ad is an unsubstituted adamantyl group;

   Optionally, the Ad is

   
10. The organic compound according to any one of claims 1 to 9, wherein said Ar ₁ and said Ar ₂ are each independently selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, substituted or Unsubstituted heteroaryl group having 5 to 18 carbon atoms.
11. The organic compound according to any one of claims 1 to 10, wherein the Ar ₁ and the Ar ₂ are each independently selected from the group consisting of the following chemical formulas (k-1) to (k-15):

    

    

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

    

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

    T ₆ to T ₁₃ are each independently selected from N or C(X ₂ ), and _{at least one of T 6} to T ₁₃ is selected from N; when _{two or more of T 6} to T ₁₃ are selected from C(X ₂ ) , Any two X _{2 are the} same or different;

    T ₁₄ to T ₂₃ are each independently selected from N or C(X ₃ ), and _{at least one of T 14} to T ₂₃ is selected from N; when _{two or more of T 14} to T ₂₃ are selected from C(X ₃ ) , Any two X _{3 are the} same or different;

    T ₂₄ to T ₃₃ are each independently selected from N or C(X ₄ ), and _{at least one of T 24} to T ₃₃ is selected from N; when _{two or more of T 24} to T ₃₃ are selected from C(X ₄ ) , Any two X _{4 are the} same or different;

    Each A _{1 is} independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, and 1 carbon atom -10 haloalkyl groups, cycloalkyl groups with 3-10 carbon atoms, alkoxy groups with 1-10 carbon atoms, and alkylthio groups with 1-10 carbon atoms;

    Each of A ₂ to A ₆ and A _{16 is} independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl group having 3 to 12 carbon atoms, and alkane having 1 to 10 carbon atoms. Group, halogenated alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, carbon Alkylthio groups having 1 to 10 atoms, heteroaryl groups having 3 to 18 carbon atoms;

    A ₇ to A ₁₅ , A ₁₇ to A ₂₁ , and X ₁ to X ₄ are each independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl group having 3 to 12 carbon atoms, carbon An alkyl group having 1 to 10 atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a carbon number of 1 ~10 alkylthio, 6-18 aryl, and 3-18 heteroaryl;

    b ₁ ~ b ₂₁ to b _k denotes, A ₁ ~ A ₂₁ to A _k expressed, k is a variable, represents any integer of 1 to 21, b _k A _k represents the number of substituents is, when b _k is greater than 1, The corresponding substituents _{Ak are the} same or different;

    Wherein, when k is selected from 1, 3, 4, 6, 18, 20 or 21, b _{k is} selected from 1, 2, 3, 4 or 5;

    When k is selected from 2, 5, 9, 11, 13, 16 or 19, b _{k is} selected from 1, 2, 3 or 4;

    When k is selected from 12 or 17, b _{k is} selected from 1, 2 or 3;

    When k is selected from 10, b _{k is} selected from 1, 2, 3, 4, 5 or 6;

    When k is selected from 7 or 14, b _{k is} selected from 1, 2, 3, 4, 5, 6 or 7;

    When k is selected from 15, b _{k is} selected from 1, 2, 3, 4, 5, 6, 7 or 8;

    When k is selected from 8, b _{k is} selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9;

    L _{1 is} selected from O, S, N (A ₂₂ ), C (A ₂₃ A ₂₄ ), Si (A ₂₃ A ₂₄ ); wherein, A ₂₂ , A ₂₃ , and A ₂₄ are each independently selected from hydrogen and the number of carbon atoms Is an aryl group having 6 to 18, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, or, optionally, the above A ₂₃ and A ₂₄ are connected to each other to form a 5- to 13-membered aliphatic ring or aromatic ring with the atoms they are connected to each other;

    Each L _{2 is} independently selected from a single bond, O, S, N (A ₂₅ ), C (A ₂₆ A ₂₇ ), Si (A ₂₆ A ₂₇ ); wherein, A ₂₅ , A ₂₆ , and A ₂₇ are each independently selected It is selected from an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, or any Optionally, the above-mentioned A ₂₆ and A ₂₇ are connected to each other to form a 5- to 13-membered aliphatic ring or a 5- to 13-membered aromatic ring with their common atoms.
12. The organic compound according to any one of claims 1 to 11, wherein the Ar ₁ and the Ar ₂ are the same or different from each other, and are each independently selected from the substituted or unsubstituted group Y ₁ , the The unsubstituted group Y _{1 is} selected from the following groups:

    

    When the Y ₁ group is substituted by one or more substituents, the substituents of Y ₁ are each independently selected from deuterium, fluorine, chlorine, cyano, alkyl groups having 1 to 6 carbon atoms, and carbon atoms Is an alkoxy group having 1 to 4, a haloalkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 9 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and the number of carbon atoms is A group consisting of 6-15 aryl groups and 3-12 heteroaryl groups; _{when the substituent of Y 1} is more than one, each substituent is the same or different.
13. The organic compound according to any one of claims 1 to 12, wherein the Ar ₁ and the Ar ₂ are the same or different from each other, and are each independently selected from the substituted or unsubstituted group Y ₂ , the The unsubstituted group Y _{2 is} selected from the following groups:

    

    When the Y ₂ group is substituted by one or more substituents, the substituents of Y ₂ are each independently selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, n-propyl, A group consisting of tert-butyl groups; _{when the substituent of Y 2} is more than one, the substituents are the same or different.
14. The organic compound according to any one of claims 1 to 13, wherein Ar ₁ and Ar ₂ are the same or different from each other, and are independently selected from the following groups:

    

    
15. The organic compound according to any one of claims 1 to 14, wherein the Ar ₁ and the Ar ₂ are the same or different from each other, and are each independently selected from the following groups:

    
16. The organic compound according to any one of claims 1 to 15, wherein the R ₁ and the R ₂ are the same or different from each other, and are each independently selected from deuterium, fluorine, chlorine, bromine, cyano, methyl Group, ethyl, isopropyl, n-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, quinoline, isoquinolyl, The group consisting of pyridyl, cyclopentyl, and cyclohexane.
17. The organic compound according to any one of claims 1 to 16, wherein the organic compound is selected from at least one of the following compounds P1-P320:

    

    

    

    

    

    

    

    

    

    

    

    
18. A device, characterized in that it comprises an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode, the functional layer containing the organic material according to any one of claims 1-17 Compound.
19. 18. The device according to claim 18, wherein the functional layer comprises a hole injection layer, a hole transport layer, an organic electroluminescence layer, an electron transport layer, and an electron injection layer, and the organic electroluminescence layer contains claims The organic compound described in any one of 1-17.
20. An electronic device, characterized in that it comprises the device according to claim 18 or 19.

Images