Heterocyclic compound and organic electroluminescent device thereof

Abstract

The invention provides a heterocyclic compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The heterocyclic compound provided by the invention has high triplet state energy level and high electron mobility, and can balance electrons and holes in a luminescent layer, broaden an exciton recombination region and improve exciton recombination efficiency when being applied to an organic electroluminescent device as a luminescent layer main body material; the luminous efficiency of the device is improved, the driving voltage of the device is reduced, and the service life of the device is prolonged. On the other hand, as an electron transport material used in an organic electroluminescent device, the compound not only can effectively improve the electron transport efficiency, but also can prevent a hole from migrating to one side of an electron transport region, and is beneficial to improving the performance of the device. In addition, the heterocyclic compound provided by the invention also has good film-forming property and stability, and is a good covering layer material. The material can be applied to the fields of information display, illumination and organic solar cells.

Description

Technical Field

[0001] The invention relates to the technical field of organic electroluminescent materials, and in particular to a heterocyclic compound and an organic electroluminescent device thereof. Background Art

[0002] Organic electroluminescent devices (OLEDs), also known as organic light-emitting diodes, have the advantages of light weight, fast response speed, high resolution, low color power consumption, etc. They have been applied to lighting, display, planar light sources and other fields. The principle of luminescence is that under the condition of external voltage driving, holes are injected from the anode and electrons are injected from the cathode. Both are transmitted to the light-emitting layer of the device, and electron-hole recombination occurs in the light-emitting layer. The recombination process produces excitons, which release a certain amount of energy and transfer it to molecules. After receiving the energy, the molecules transition from the ground state to the excited state. When they transition from the excited state to the ground state, they release energy outward in the form of light, thereby generating luminescence.

[0003] The performance of organic electroluminescent devices is directly related to the composition structure of the device. Improving the device structure and optimizing the device manufacturing technology are effective means to improve the performance of the device. Nowadays, organic electroluminescent devices mostly adopt a sandwich structure, with an organic functional layer set between the two end electrodes. The organic functional layer can be divided into an electron transport region, a light-emitting layer, a hole transport region, etc., where the light-emitting layer includes a host material and a guest material. The host material of the light-emitting layer often needs to have the following characteristics: the triplet energy level of the host is greater than the triplet energy level of the guest to avoid energy backflow; the HOMO energy level and LUMO energy level of the host match the energy levels of the hole transport region and the electron transport region to reduce the injection barrier of carriers and capture carriers; the carrier transmission rate is high, which is conducive to the recombination of excitons and the widening of their recombination area; the material has good stability and film-forming properties, which is conducive to the uniformity of the film and the stability of the device during vacuum evaporation. However, the current host materials still have many shortcomings and need further improvement.

[0004] On the other hand, balanced carrier injection is also a key factor affecting the performance of organic electroluminescent devices. Holes and electrons are transported to the light-emitting layer through the hole transport region and the electron transport region respectively, so the selection of hole transport materials and electron transport materials is particularly important. However, many electron transport materials currently still have problems such as low electron mobility, HOMO / LUMO energy level mismatch, poor stability and film-forming properties, resulting in unbalanced transmission of electrons and holes in organic electroluminescent devices, low recombination efficiency of electrons and holes in the light-emitting layer, and many other problems that need to be further improved.

[0005] Therefore, it is necessary to develop light-emitting layer host materials and electron transport materials with better performance to improve the performance of organic electroluminescent devices. Summary of the invention

[0006] In view of the problems existing in the prior art, the present invention provides a heterocyclic compound and an organic electroluminescent device thereof.

[0007] The present invention provides a heterocyclic compound represented by the following formula 1:

[0008]

[0009] Wherein, the x is the same or different and is selected from CR a or N;

[0010] The R a One selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring;

[0011] Ar0 is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring fused ring, or the N atom corresponding to Ar0 is the connection site with L1;

[0012] The R1 and R2 are the same or different and are selected from one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, and substituted or unsubstituted C3-C20 cycloalkyl;

[0013] The n1 is the same or different and is selected from 0, 1, 2, 3 or 4;

[0014] The L0 is selected from the group shown in the following formula 1-a,

[0015]

[0016] The v is the same or different from CR b or N, and at least one v is selected from N, and the v bonded to L1 and L2 is selected from C atoms;

[0017] The R b is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or two adjacent R b Bonding to form a substituted or unsubstituted benzene ring or nitrogen-containing heterocyclic ring;

[0018] Said b1 is selected from 1, 2 or 3;

[0019] The L1 and L2 are the same or different and are selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring sub-condensed ring group;

[0020] Said Y is selected from O or S;

[0021] The z are the same or different and are selected from CH or N;

[0022] The R3 is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R3 are bonded to form a substituted or unsubstituted ring;

[0023] The m1 is selected from 0, 1, 2, 3 or 4;

[0024] Ar1 is selected from one or a combination of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring;

[0025] The L3 is selected from a single bond, a substituted or unsubstituted C2-C30 heteroarylene group or one of the groups shown below,

[0026]

[0027] The y is the same or different and is selected from CR 11 ;

[0028] The R 11 is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or two adjacent R 11 Bonding to form substituted or unsubstituted alicyclic rings;

[0029] The W is selected from CR 12 R 13 ;

[0030] The R 12 , R13 The same or different R is selected from hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or adjacent R 12 , R 13 Bonding to form a substituted or unsubstituted ring;

[0031] The L4 is selected from one or a combination of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, and a substituted or unsubstituted C3-C20 alicyclic group and C6-C30 aromatic ring condensed group.

[0032] The present invention also provides an organic electroluminescent device, which contains the heterocyclic compound described in the present invention.

[0033] Beneficial effects: The heterocyclic compound of Formula 1 of the present invention has a high triplet energy level and high electron mobility. It is used as a main material of the light-emitting layer in an organic electroluminescent device, which can balance the electrons and holes in the light-emitting layer, broaden the exciton recombination area, and improve the exciton recombination efficiency, thereby improving the luminous efficiency of the device, reducing the driving voltage of the device, and extending the service life of the device. On the other hand, as an electron transport material used in an organic electroluminescent device, it can not only effectively improve the electron transport efficiency, but also block the migration of holes to one side of the electron transport area, which is beneficial to improving the performance of the device. In addition, the heterocyclic compound of Formula 1 of the present invention also has good film-forming properties and stability, and is a good covering layer material. DETAILED DESCRIPTION

[0034] The present invention is further explained below in conjunction with specific embodiments. It should be understood that these embodiments are only used to illustrate the present invention and are not used to limit the scope of the present invention. After reading the present invention, various equivalent forms of modifications to the present invention by those skilled in the art all fall within the scope of protection required by this application.

[0035] In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes the atom in both its natural isotopic abundance and unnatural abundance.

[0036] The halogen described in the present invention includes fluorine, chlorine, bromine and iodine.

[0037] In the present invention, the "unsubstituted ZZ group" in the "substituted or unsubstituted ZZ group" means that the hydrogen atom of the "ZZ group" is not replaced by a substituent. For example, the "unsubstituted aryl group" in the "substituted or unsubstituted C6-C60 aryl group" means that the hydrogen atom of the "aryl group" is not replaced by a substituent. And so on.

[0038] In the present invention, "CXX-CYY" in "substituted or unsubstituted ZZ group of CXX-CYY" represents the number of carbon atoms in the unsubstituted "ZZ group", and when the "ZZ group" has a substituent, the number of carbon atoms of the substituent is not included. For example, "C6-C60" in "substituted or unsubstituted C6-C60 aryl group" represents the number of carbon atoms in the unsubstituted "aryl group", and when the "aryl group" has a substituent, the number of carbon atoms in the substituent is not included. "C3-C25" in "substituted or unsubstituted C3-C25 alicyclic ring and C6-C30 aromatic ring fused ring group" represents the number of carbon atoms in the unsubstituted "alicyclic ring", and when the "alicyclic ring" has a substituent, the number of carbon atoms of the substituent is not included; "C6-C30" represents the number of carbon atoms in the unsubstituted "aromatic ring", and when the "aromatic ring" has a substituent, the number of carbon atoms of the substituent is not included. And so on.

[0039] In the present invention, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically, it can be connected to any of the corresponding optional sites of the ring. For example, Can be expressed Can be expressed And so on.

[0040] In the present invention, when the position of a substituent on an aromatic ring is not fixed, it means that it can be connected to any of the corresponding optional positions of the aromatic ring. For example, Can be expressed Can be expressed Can be expressed And so on.

[0041] In the present invention, "two adjacent groups are bonded to form a ring" means that adjacent groups are bonded to each other and optionally aromatized to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. The hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle may include an aliphatic heterocycle or an aromatic heterocycle. The aliphatic hydrocarbon ring may be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle may be a saturated aliphatic heterocycle or an unsaturated aliphatic heterocycle. The hydrocarbon ring and the heterocycle may be monocyclic or polycyclic groups. In addition, the ring formed by the combination of adjacent groups may be connected to another ring to form a spiro structure. Specific examples are shown below:

[0042]

[0043] In the present invention, the ring formed by connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a condensed ring, a spiro ring, etc., for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but are not limited thereto.

[0044] The term "substituted" in "substituted or unsubstituted" as used herein means that at least one hydrogen atom on the group is replaced by a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different. The position of the hydrogen atoms replaced by the substituents may be any position. The substituent represented by the "substituted" in the above-mentioned "substituted or unsubstituted" includes the following groups, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1~C15 alkoxy, substituted or unsubstituted C6~C20 aryloxy, substituted or unsubstituted C2~C15 heterocyclic group, substituted or unsubstituted C1~C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3~C15 cycloalkyl, substituted or unsubstituted C6~C20 aryl, substituted or unsubstituted C2~C20 heteroaryl, substituted or unsubstituted C3~C15 alicyclic and C6~C20 aromatic ring fused ring group, substituted or unsubstituted C3~C15 alicyclic and C2~C20 heteroaromatic ring fused ring group, etc. Preferred are the following groups: deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, bornyl, isobornyl, fencyl, silyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, phenanthrenyl, triphenylene, anthracenyl, pyrenyl, , benzothiophene, dihydrobenzothiophene, dihydrobenzothiophene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, etc. In addition, each of the above substituents can be substituted or unsubstituted. Two adjacent substituents can be bonded to form a ring.

[0045] The alkyl group described in the present invention refers to a hydrocarbon group formed by removing a hydrogen atom from an alkane molecule. The alkyl group may be a straight-chain alkyl group or a branched-chain alkyl group. When the number of carbon atoms of the chain alkyl group described in the present invention is three or more, its isomers are included, for example, the propyl group includes n-propyl and isopropyl; the butyl group includes n-butyl, isobutyl, sec-butyl, tert-butyl, and so on. Examples of the alkyl group include, but are not limited to, the groups described below, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited thereto. The number of carbon atoms of the alkyl group is C1 to C30, preferably C1 to C25, preferably C1 to C20, preferably C1 to C15, and more preferably C1 to C10.

[0046] The silyl group described in the present invention refers to -Si(R k )3 groups, wherein each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic fused ring. Preferably, each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The carbon number of the alkyl group is preferably C1-C20, preferably C1-C15, more preferably C1-C10, and most preferably C1-C8. The carbon number of the cycloalkyl group is preferably C3-C20, preferably C3-C15, more preferably C3-C10, and most preferably C3-C7. Preferably, each R kThe same or different radicals are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentanylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, and the like, but are not limited thereto.

[0047] The cycloalkyl group of the present invention refers to a hydrocarbon group formed by removing a hydrogen atom from a cycloalkane molecule. The cycloalkyl group includes a monocyclic cycloalkyl group, a polycyclic cycloalkyl group, and a bridged ring cycloalkyl group. Examples of the cycloalkyl group include, but are not limited to, the following groups, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, bornyl, fenchyl, isobornyl, etc., but are not limited thereto. The number of carbon atoms of the cycloalkyl group is C3 to C30, preferably C3 to C25, preferably C3 to C20, preferably C3 to C15, and more preferably C3 to C10.

[0048] The aryl group described in the present invention refers to a general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon of an aromatic compound molecule. The aryl group includes a monocyclic aryl group, a polycyclic aryl group, a condensed ring aryl group or a combination thereof. Examples of the aryl group include, but are not limited to, the following groups: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, triphenylene, fluorenyl, benzofluorenyl, spirobifluorenyl, spiroanthrafluorenyl, pyrenyl, The number of carbon atoms in the aryl group is C6 to C60, preferably C6 to C30, preferably C6 to C25, and more preferably C6 to C20.

[0049] The heteroaryl group of the present invention refers to a monovalent group in which at least one carbon atom in the aromatic group is replaced by a heteroatom. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. Examples of the heteroaryl group include, but are not limited to, the following groups: benzofuranyl, naphthofuranyl, phenanthrofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothiophenyl, naphthothiophenyl, phenanthrothiophenyl, dibenzothiophenyl, benzodibenzothiophenyl, indolyl, naphthoindolyl, carbazolyl, benzocarbazolyl, spirofluorene xanthracene, spirofluorene thioanthracene, spirofluorene azaanthracene, dihydrobenzofuranyl, dihydrobenzothiophenyl, phenoxazinyl, phenothiazinyl, dihydroacridinyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, etc., but are not limited thereto. The carbon number of the heteroaryl group is C2 to C60, preferably C2 to C30, preferably C2 to C25, and more preferably C3 to C20.

[0050] The fused ring group of alicyclic ring and aromatic ring described in the present invention refers to the general term for a monovalent group after alicyclic ring and aromatic ring are fused together and one hydrogen atom is removed. Examples of the fused ring group of alicyclic ring and aromatic ring include, but are not limited to, the following groups, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, benzocycloheptenyl, etc., but are not limited thereto. The carbon number of the alicyclic ring is C3-C30, preferably C3-C25, preferably C3-C20, preferably C3-C15, more preferably C3-C10, more preferably C3-C8. The carbon number of the aromatic ring is C6-C60, preferably C6-C30, preferably C6-C25, preferably C6-C18, more preferably C6-C12, more preferably C6-C10.

[0051] The arylene group described in the present invention refers to the general term for the divalent group left after two hydrogen atoms are removed from the aromatic carbon of the aromatic compound molecule. The arylene group includes a monocyclic arylene group, a polycyclic arylene group, a condensed ring arylene group or a combination thereof. Examples of the arylene group include, but are not limited to, the following groups, phenylene, biphenylene, terphenylene, naphthylene, phenanthrenyl, fluorenylene, benzofluorenylene, dibenzofluorenylene, naphthylene, spirobifluorenylene, etc., but are not limited thereto. The number of carbon atoms of the arylene group is C6 to C30, preferably C6 to C25, preferably C6 to C20, and more preferably C6 to C18.

[0052] The heteroarylene group described in the present invention refers to a divalent group in which at least one carbon atom in the arylene group is replaced by a heteroatom. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. The heteroarylene group includes a monocyclic heteroarylene group, a polycyclic heteroarylene group, a condensed ring heteroarylene group, or a combination thereof. Examples of the heteroarylene group include, but are not limited to, the following groups, pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, quinolylene, quinazolinylene, naphthyridinylene, etc., but are not limited thereto. The number of carbon atoms in the heteroarylene group is C2 to C30, preferably C2 to C25, and preferably C2 to C20.

[0053] The sub-condensed ring group of the alicyclic ring and the aromatic ring described in the present invention refers to the general term for the divalent group left after the alicyclic ring and the aromatic ring are fused together and two hydrogen atoms are removed. Examples of the sub-condensed ring group of the alicyclic ring and the aromatic ring include, but are not limited to, the following groups, benzocyclopropanediyl, benzocyclobutanediyl, indenyldiyl, indenyldiyl, tetrahydronaphthyldiyl, dihydronaphthyldiyl, benzocycloheptanediyl, benzocyclobutenyldiyl, benzocycloheptenyldiyl, etc., but are not limited thereto. The carbon number of the alicyclic ring is C3-C30, preferably C3-C25, preferably C3-C20, preferably C3-C15, and more preferably C3-C8. The carbon number of the aromatic ring is C6-C60, preferably C6-C30, preferably C6-C20, preferably C6-C18, and preferably C6-C10.

[0054] The present invention provides a heterocyclic compound represented by the following formula 1:

[0055]

[0056] Wherein, the x is the same or different and is selected from CR a or N;

[0057] The R a One selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring;

[0058] Ar0 is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring fused ring, or the N atom corresponding to Ar0 is the connection site with L1;

[0059] The R1 and R2 are the same or different and are selected from one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, and substituted or unsubstituted C3-C20 cycloalkyl;

[0060] The n1 is the same or different and is selected from 0, 1, 2, 3 or 4;

[0061] The L0 is selected from the group shown in the following formula 1-a,

[0062]

[0063] The v is the same or different from CR b or N, and at least one v is selected from N, and the v bonded to L1 and L2 is selected from C atoms;

[0064] The R b is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or two adjacent R b Bonding to form a substituted or unsubstituted benzene ring or nitrogen-containing heterocyclic ring;

[0065] Said b1 is selected from 1, 2 or 3;

[0066] The L1 and L2 are the same or different and are selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring sub-condensed ring group;

[0067] Said Y is selected from O or S;

[0068] The z are the same or different and are selected from CH or N;

[0069] The R3 is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R3 are bonded to form a substituted or unsubstituted ring;

[0070] The m1 is selected from 0, 1, 2, 3 or 4;

[0071] Ar1 is selected from one or a combination of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring;

[0072] The L3 is selected from a single bond, a substituted or unsubstituted C2-C30 heteroarylene group or one of the groups shown below,

[0073]

[0074] The y is the same or different and is selected from CR 11 ;

[0075] The R 11 is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or two adjacent R 11 Bonding to form substituted or unsubstituted alicyclic rings;

[0076] The W is selected from CR 12 R 13 ;

[0077] The R 12 , R 13 The same or different R is selected from hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or adjacent R 12 , R 13 Bonding to form a substituted or unsubstituted ring;

[0078] The L4 is selected from one or a combination of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, and a substituted or unsubstituted C3-C20 alicyclic group and C6-C30 aromatic ring condensed group.

[0079] Preferably, the Selected from one of the following groups,

[0080]

[0081] The R athe same or different selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl;

[0082] The r0 is selected from 0, 1, 2 or 3; the r1 is selected from 0, 1 or 2; and the r2 is selected from 0 or 1.

[0083] Preferably, the Selected from one of the following groups,

[0084]

[0085] The R a The same or different ones are selected from hydrogen, deuterium, cyano, halogen, nitro, one of the following groups which are substituted or unsubstituted by one or more deuteriums or C1-C8 alkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptyl, benzocyclopentenyl, and benzocyclohexenyl.

[0086] Preferably, the Selected from one of the following groups,

[0087]

[0088] The R aThe same or different ones are selected from one of hydrogen, deuterium, cyano, halogen, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl and benzocyclohexenyl.

[0089] Preferably, Ar0 is selected from one of the following groups:

[0090]

[0091] The e is the same or different from CR c or N;

[0092] The Q is selected from O, S, CR d R e or NR f ; Q1 is selected from O, S or NR g ; Q2 is selected from CR i or N;

[0093] The R c is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or two adjacent R c Bonding to form a substituted or unsubstituted ring;

[0094] The R d , R e The same or different R is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or adjacent R d , R e Bonding to form a substituted or unsubstituted ring;

[0095] The R iOne selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring;

[0096] The R f , R g The same or different ones are selected from substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring.

[0097] Preferably, the One selected from the following groups,

[0098]

[0099]

[0100] The R1 and R2 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, or a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, or tert-butyldimethylsilyl;

[0101] The R c the same or different selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent Rc Bonding to form substituted or unsubstituted benzene rings;

[0102] The n1 is selected from 0, 1, 2, 3 or 4; the n2 is selected from 0, 1, 2 or 3;

[0103] The s1 is selected from 0, 1, 2, 3, 4 or 5; the s2 is selected from 0, 1, 2, 3 or 4; the s3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the s4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the s5 is selected from 0, 1, 2 or 3; the s6 is selected from 0, 1, 2, 3, 4, 5 or 6; the s7 is selected from 0, 1 or 2; the s8 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the s9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.

[0104] Preferably, R1, R2, R c The "substituted or unsubstituted" substituent is selected from deuterium, cyano, halogen, nitro, one of the following groups substituted or unsubstituted by one or more deuteriums, C1-C6 alkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethyl Silyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl.

[0105] Preferably, L0 is selected from one of the following groups:

[0106]

[0107] The R b the same or different selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl;

[0108] The d1 is selected from 0, 1, 2 or 3; the d2 is selected from 0, 1 or 2; the d3 is selected from 0 or 1; the d4 is selected from 0, 1, 2, 3, 4 or 5; the d5 is selected from 0, 1, 2, 3 or 4; the d6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the d7 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0109] Preferably, the R b The same or different radicals are selected from hydrogen, deuterium, cyano, halogen, nitro, or one of the following radicals which are substituted or unsubstituted with one or more deuteriums: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptyl, benzocyclopentenyl, and benzocyclohexenyl.

[0110] Preferably, L1 and L2 are the same or different and are selected from a single bond or one of the following groups:

[0111]

[0112] The R4 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, or a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, or two adjacent R4 are bonded to form a substituted or unsubstituted benzene ring;

[0113] Said a1 is selected from 0, 1, 2, 3 or 4; said a2 is selected from 0, 1, 2, 3, 4, 5 or 6; said a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said a4 is selected from 0, 1, 2 or 3; said a5 is selected from 0, 1 or 2; said a6 is selected from 0, 1, 2, 3, 4 or 5; said a7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0114] Preferably, the R4 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, or one of the following groups which are substituted or unsubstituted with one or more deuteriums: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, and benzocyclohexenyl.

[0115] Preferably, the One selected from the following groups,

[0116]

[0117] The R3 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylmethyl Silyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent R3 are bonded to form a substituted or unsubstituted benzene ring;

[0118] The m1 is selected from 0, 1, 2, 3 or 4; the m2 is selected from 0, 1, 2 or 3; the m3 is selected from 0, 1 or 2; the m4 is selected from 0 or 1; the m5 is selected from 0, 1, 2, 3, 4, 5 or 6; the m6 is selected from 0, 1, 2, 3, 4 or 5; the m7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the m8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0119] Preferably, R3 is selected from hydrogen, deuterium, cyano, halogen, nitro, and one of the following groups which are substituted or unsubstituted with one or more deuteriums: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, trimethyl ... Isopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl.

[0120] Preferably, Ar1 is selected from one of the following groups:

[0121]

[0122] The u are the same or different and are selected from CR5 or N;

[0123] The T is selected from O, S, CR6R7 or NR8; the T1 is selected from O, S or NR9; the T2 is selected from CR 10 or N;

[0124] The R5 is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R5 are bonded to form a substituted or unsubstituted ring;

[0125] The R6 and R7 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or adjacent R6 and R7 are bonded to form a substituted or unsubstituted C3-C7 ring;

[0126] The R8 and R9 are the same or different and are selected from a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, or a fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring;

[0127] The R 10 One selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring.

[0128] Preferably, Ar1 is selected from one of the following groups:

[0129]

[0130]

[0131] The R5 may be the same or different and may be selected from hydrogen, deuterium, cyano, halogen, nitro, or a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylmethyl Silyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent R5 are bonded to form a substituted or unsubstituted benzene ring;

[0132] The c1 is selected from 0, 1, 2, 3 or 4; the c1 is selected from 0, 1, 2, 3 or 4; the c1 is selected from 0, 1, 2, 3 or 4; the c1 is selected from 0, 1, 2, 3 or 4; the c1 is selected from 0, 1, 2, 3 or 4; the c1 is selected from 0, 1, 2, 3 or 4; the c1 is selected from 0, 1, 2, 3 or 4; the c1 is selected from 0, 1, 2, 3 or 4.

[0133] Preferably, the "substituted or unsubstituted" substituent in R5 is selected from deuterium, cyano, halogen, nitro, and one of the following groups substituted or unsubstituted by one or more deuterium or C1-C6 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, Triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl.

[0134] Preferably, L3 is selected from a single bond or one of the following groups:

[0135]

[0136] The R 11 the same or different selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylmethyl Silyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl;

[0137] The R 12 , R 13the same or different selected from hydrogen, deuterium, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, trimethyl ... tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl;

[0138] The p1 is selected from 0, 1, 2, 3 or 4; the p2 is selected from 0, 1, 2, 3, 4, 5 or 6; the p3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the p4 is selected from 0, 1, 2 or 3; the p5 is selected from 0, 1 or 2; the p6 is selected from 0 or 1; the p7 is selected from 0, 1, 2, 3, 4 or 5; the p8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the p9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0139] Preferably, the R 11 , R 12 , R 13 The "substituted or unsubstituted" substituent is selected from deuterium, cyano, halogen, nitro, one of the following groups substituted or unsubstituted by one or more deuterium, C1-C6 alkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylmethyl Silyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl.

[0140] Preferably, L4 is selected from a single bond or one of the following groups:

[0141]

[0142]

[0143] The R h the same or different selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent R h Bonding to form a substituted or unsubstituted ring;

[0144] The t1 is selected from 0, 1, 2, 3 or 4; the t2 is selected from 0, 1, 2, 3, 4, 5 or 6; the t3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the t4 is selected from 0, 1, 2 or 3; the t5 is selected from 0, 1 or 2; the t6 is selected from 0 or 1; the t7 is selected from 0, 1, 2, 3, 4 or 5; the t8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the t9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0145] Preferably, the R h the same or different selected from hydrogen, deuterium, cyano, halogen, nitro, one of the following groups substituted or unsubstituted by one or more deuteriums: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylmethyl Silyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent R h Bonding to form a substituted or unsubstituted benzene ring.

[0146] Preferably, the heterocyclic compound is selected from one of the structures shown below:

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164] Some specific chemical structures of the heterocyclic compounds represented by Formula 1 of the present invention are listed above, but the present invention is not limited to these listed chemical structures, and all the groups based on the structure represented by Formula 1 and having substituents as defined above should be included.

[0165] In addition, the present invention also provides an organic electroluminescent device, wherein the organic electroluminescent device contains the heterocyclic compound of the present invention.

[0166] Preferably, the organic electroluminescent device comprises an anode, a cathode and an organic layer, wherein the organic layer is located between the cathode and the anode or outside one or more electrodes of the anode and the cathode, and the organic layer contains the heterocyclic compound of the present invention.

[0167] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes at least one of a light-emitting layer and an electron transport region, and at least one of the light-emitting layer and the electron transport region contains the heterocyclic compound of the present invention.

[0168] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes a light-emitting layer, and the light-emitting layer contains the heterocyclic compound of the present invention.

[0169] Preferably, the organic layer is located between the anode and the cathode, the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material contains the heterocyclic compound of the present invention.

[0170] Preferably, the organic layer is located between the anode and the cathode, the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, the host material includes an N-type host material and a P-type host material, and the N-type host material contains the heterocyclic compound of the present invention.

[0171] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes an electron transport region, and the electron transport region contains the heterocyclic compound of the present invention.

[0172] Preferably, the organic layer is located between the anode and the cathode, the organic layer includes an electron transport region, the electron transport region includes at least one layer of an electron injection layer, an electron transport layer, and a hole blocking layer, and at least one layer of the electron injection layer, the electron transport layer, and the hole blocking layer contains the above-mentioned heterocyclic compound of the present invention.

[0173] Preferably, the organic layer is located between the anode and the cathode, the organic layer includes an electron transport region, the electron transport region includes an electron transport layer, and the electron transport layer contains the heterocyclic compound of the present invention.

[0174] Preferably, the organic layer is located between the anode and the cathode, the organic layer includes an electron transport region, the electron transport region includes a hole blocking layer, and the hole blocking layer contains the heterocyclic compound of the present invention.

[0175] Preferably, the organic layer is located between the anode and the cathode, the organic layer includes an electron transport region, the electron transport region includes an electron transport layer and a hole blocking layer, and the electron transport layer and the hole blocking layer contain the heterocyclic compound of the present invention.

[0176] Preferably, the organic layer is located outside one or more electrodes of the anode and the cathode, and the organic layer includes a covering layer, and the covering layer contains the heterocyclic compound of the present invention.

[0177] Preferably, the organic electroluminescent device described in the present invention is divided into a single-layer organic electroluminescent device and a stacked organic electroluminescent device. The single-layer organic electroluminescent device is an organic electroluminescent device containing one light-emitting unit, and the stacked organic electroluminescent device is an organic electroluminescent device formed by connecting two or more independent light-emitting units in series through a charge generation layer.

[0178] Preferably, the organic electroluminescent device described in the present invention is a single-layer organic electroluminescent device, which includes an anode, a cathode and an organic layer, wherein the organic layer is located between the anode and the cathode or on the outside of one or more electrodes of the anode and the cathode, and the organic layer contains the heterocyclic compound described in the present invention.

[0179] Preferably, the organic electroluminescent device described in the present invention is a stacked organic electroluminescent device, which comprises an anode, a cathode and an organic layer, wherein the organic layer is located between the anode and the cathode, and the organic layer contains the heterocyclic compound described in the present invention.

[0180] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes a plurality of light-emitting units and an N-type charge generation layer and a P-type charge generation layer located between adjacent light-emitting units, and the N-type charge generation layer contains the heterocyclic compound described in the present invention.

[0181] Preferably, the N-type charge generation layer can be formed by doping the heterocyclic compound described in the present invention with other materials.

[0182] The organic functional layer of the organic electroluminescent device of the present invention may contain a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a covering layer, etc. The organic functional layer may be formed by a single-layer structure or a multi-layer structure of stacking the above organic layers, and each of the organic functional layers may also contain one or more materials.

[0183] The present invention has no particular limitation on the materials of the thin films in the organic electroluminescent device, and materials known in the art can be used. The organic functional layers of the organic electroluminescent device mentioned above and the electrodes on both sides of the device are introduced below:

[0184] The anode of the present invention preferably has a material with a large work function, including metal oxides, metal alloys, metals, conductive polymers, etc., but not limited thereto. Specific examples may include gold (Au), silver (Ag), zinc (Zn), indium zinc oxide (IZO), indium tin oxide (ITO), zinc oxide (ZnO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polyaniline, etc., but not limited thereto.

[0185] The hole injection layer of the present invention is preferably a material with good hole injection ability. The hole injection layer material includes oligothiophene, arylamine derivatives, perylene derivatives, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, and polyaniline-based conductive polymers, but are not limited thereto. Specific examples may include copper phthalocyanine (CuPc), 4,4',4"-tri(N-(1-naphthyl)-N-phenylamino)triphenylamine (1-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), etc., but are not limited thereto.

[0186] The hole transport layer of the present invention is preferably a material with high hole mobility. The hole transport material includes carbazole derivatives, aromatic amine derivatives, biphenyl diamine derivatives, phthalocyanine compounds, etc., but is not limited thereto. Specific examples may include N, N'-diphenyl-N, N'-(1-naphthyl)-1, 1'-biphenyl-4, 4'-diamine (NPB), N4, N4'-di(biphenyl-4-yl)-N4, N4'-diphenylbiphenyl-4, 4'-diamine (TPD-10), 4, 4', 4 "-tris(carbazole-9-yl) triphenylamine (TCTA), etc., but are not limited thereto.

[0187] The electron blocking layer of the present invention preferably has a material with electron blocking ability and a suitable energy level. The electron blocking material includes aromatic amine derivatives, carbazole derivatives, etc., but is not limited thereto. Specific examples may include N, N'-di(naphthalene-1-yl)-N, N'-diphenyl-benzidine (NPD), N, N-di([1, 1'-biphenyl]-4-)-(9H-carbazole-9-yl)-[1, 1'-biphenyl]-4-amine, etc., but are not limited thereto.

[0188] The light-emitting layer of the present invention comprises a host material and a guest material. The host material comprises thiazole derivatives, benzimidazole derivatives, aromatic amine derivatives, carbazole derivatives, etc., but is not limited thereto. Specific examples may include 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 1,3-bis(N-carbazole)benzene (MCP), 1,3,5-tri(carbazole-9-yl)benzene (TCP), 9,10-di(2-naphthyl)anthracene (ADN), etc., but are not limited thereto. The heterocyclic compound of the present invention is preferred. The heterocyclic compound of the present invention can be used as a host material alone or in combination with a p-type host material. When used in combination with a p-type host material, the weight ratio of the heterocyclic compound of the present invention to the p-type host material is 1:99 to 99:1, preferably 20:80 to 80:20. The guest material comprises aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc., but is not limited thereto. Specific examples may include tris(2-phenylpyridine)iridium (Ir(ppy)3), tris[2-(3-methyl-2-pyridyl)phenyl]iridium (Ir(3mppy)3), bis(2-phenylpyridine)(acetylacetonate)iridium (Ir(ppy)2(acac)), bis(1-phenyl-isoquinoline)(acetylacetonate)iridium (Ir(piq)2(acac)), tris(1-phenyl-isoquinoline)iridium (Ir(piq)3), 2,5,8,11-tetra-tert-butylperylene (TBPe), etc., but are not limited thereto.

[0189] The hole blocking layer of the present invention preferably has a hole blocking ability and a material with a suitable energy level, and the hole blocking material includes a metal complex, a heteroaromatic compound, etc., but is not limited thereto. Specific examples may include di(2-methyl-8-hydroxyquinoline-N1,08)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 1,3,5-tri(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), etc., but are not limited thereto. The heterocyclic compound described in the present invention is preferred.

[0190] The electron transport layer of the present invention preferably has a material with high electron mobility, and the electron transport material includes imidazole derivatives, phenanthroline derivatives, pyridine derivatives, triazine derivatives, quinoline derivatives, oxadiazole derivatives, etc., but is not limited thereto. Specific examples may include 8-hydroxyquinoline aluminum (Alq3), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,4'-bis (4,6-diphenyl-1,3,5-triazine-2-yl) biphenyl (BTB), etc., but are not limited thereto. The heterocyclic compound described in the present invention is preferred.

[0191] The electron injection layer of the present invention preferably has a material with good electron injection ability, and the electron injection material includes metals, metal compounds, metal oxides, etc., but is not limited thereto. Specific examples may include lithium (Li), lithium fluoride (LiF), magnesium fluoride (MgF2), 8-hydroxyquinoline lithium (LiQ), calcium fluoride (CaF2), cesium carbonate (Cs2CO3), lithium oxide (Li2O), etc., but are not limited thereto.

[0192] The cathode of the present invention is preferably a material with a small work function, and the cathode material includes metals, metal alloys, metal oxides, conductive polymers, etc., but is not limited thereto. Specific examples may include sodium (Na), potassium (K), aluminum (Al), lithium (Li), magnesium (Mg), magnesium-silver alloy (Mg / Ag), LiF / Al or LiO2 / Al multilayer structure materials, etc., but are not limited thereto.

[0193] The cover layer material of the present invention is preferably a material with excellent light extraction performance, and the cover layer material includes aromatic amine derivatives, metal compounds, carbazole derivatives, etc., but is not limited thereto. Specific examples may include tris(8-hydroxyquinoline)aluminum (Alq3), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), etc., but are not limited thereto. The heterocyclic compound described in the present invention is preferred.

[0194] The charge generation material of the present invention can be divided into N-type charge generation material and P-type charge generation material. Specific examples of the N-type charge generation material of the present invention may include tris-(8-hydroxyquinolinate)aluminum (Alq3), bis(2-methyl-8-quinolinate-N1,O8)-(1,1'-biphenyl-4-phenolate)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), etc., or doped with alkali metals or alkaline earth metals, but not limited thereto. The heterocyclic compound of the present invention is preferred. Specific examples of the P-type charge generating material described in the present invention may include 4,4',4"-tri(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), copper phthalocyanine (CuPc), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), etc., but are not limited thereto.

[0195] There is no particular limitation on the method for preparing the thin films in the organic electroluminescent device of the present invention, and vacuum evaporation, sputtering, spin coating, spray coating, screen printing, laser transfer, etc. may be used, but are not limited thereto.

[0196] The organic electroluminescent device of the present invention is mainly used in the fields of panel display, lighting, organic solar cells, organic thin film transistors, flexible OLEDs, etc., but is not limited thereto.

[0197] The present invention is described in more detail with reference to the following examples. However, the following examples are only used to illustrate the present description, and the scope of the present description is not limited to these examples.

[0198] Synthesis Example

[0199] Raw materials and reagents: The present invention has no particular restrictions on the raw materials or reagents used in the following synthetic examples, and they can be commercially available products or prepared by preparation methods well known to those skilled in the art. The raw materials and reagents used in the present invention are all reagent-grade.

[0200] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube organic element analyzer (Elementar, Germany).

[0201] There is no particular limitation on the preparation method of the heterocyclic compound represented by Formula 1 of the present invention, and conventional methods known to those skilled in the art can be used. For example, carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc. The heterocyclic compound represented by Formula 1 of the present invention can be prepared by the synthetic route shown below.

[0202] Intermediate Synthesis Route 1:

[0203]

[0204] Intermediate Synthesis Route 2:

[0205]

[0206] Synthesis route of the compound:

[0207]

[0208] The X n is a halogen, such as X n The same or different ones are selected from Cl, Br, I;

[0209] The A is selected from *-B(OH)2 or

[0210] The limitations of Ar0, Ar1, Y, L0, L1, L2, L3, L4, R1, R2, R3, x, z, m1, n1, and n2 are the same as those mentioned above.

[0211] Synthesis Example 1: Preparation of Intermediate d-16

[0212]

[0213] Preparation of intermediate g-16: Under nitrogen protection, e-16 (13.38 g, 80.00 mmol), f-16 (15.40 g, 80.00 mmol), Pd(OAc)2 (0.18 g, 0.80 mmol), P(t-Bu)3 (0.32 g, 1.60 mmol), sodium tert-butoxide (15.38 g, 160.00 mmol) and 600 ml toluene solvent were added to the reaction bottle, and the mixture was stirred. The mixed solution of the above reactants was heated to reflux for 5 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, and the liquid was separated by standing. The organic layer was collected and dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The temperature was lowered for crystallization, and suction was filtered. The obtained solid was recrystallized with toluene: methanol = 9:1 to obtain intermediate g-16 (18.29 g, yield 82%); HPLC purity ≧99.70%. Mass spectrum m / z: 278.0630 (theoretical value: 278.0611).

[0214] Preparation of intermediate d-16: Under nitrogen protection, g-16 (13.94 g, 50.00 mmol), biboric acid pinacol ester (12.70 g, 50.00 mmol), Na2CO3 (10.60 g, 100.00 mmol), Pd(PPh3)4 (0.58 g, 0.50 mmol) and 300 mL DMF were added to the reaction bottle, and the mixture was stirred under reflux for 4.5 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and then extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was concentrated by vacuum distillation. The mixture was cooled and crystallized, filtered, and then recrystallized from ethyl acetate to obtain intermediate d-16 (14.63 g, yield 79%); HPLC purity ≧99.85%. Mass spectrum m / z: 370.1840 (theoretical value: 370.1853).

[0215] According to the above preparation method, the present invention also synthesizes the following intermediates:

[0216]

[0217]

[0218] Synthesis Example 2: Preparation of Intermediate d1-54

[0219]

[0220] Preparation of intermediate g1-54: Under nitrogen protection, e1-54 (22.97 g, 80.00 mmol), f-16 (15.40 g, 80.00 mmol), K2CO3 (16.58 g, 120.00 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), 450 mL toluene / ethanol / water (2:1:1) were added to the reaction bottle, and the mixture was stirred under reflux for 4.5 hours. After the reaction, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then the obtained solid was recrystallized with toluene / ethanol = 10:1 to obtain intermediate g1-54 (22.14 g, yield 78%), HPLC purity ≧ 99.78%. Mass spectrum m / z: 354.0914 (theoretical value: 354.0924).

[0221] Preparation of intermediate d1-54: Under nitrogen protection, g1-54 (17.74 g, 50.00 mmol), biboric acid pinacol ester (12.70 g, 50.00 mmol), Na2CO3 (10.60 g, 100.00 mmol), Pd(dppf)Cl2 (0.37 g, 0.50 mmol) and 300 mL DMF were added to the reaction bottle, and the mixture was stirred under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and then extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, the solvent was concentrated by vacuum distillation, the temperature was lowered for crystallization, suction filtered, and then recrystallized from ethyl acetate to obtain intermediate d1-54 (16.96 g, yield 76%); HPLC purity ≧99.81%. Mass spectrum m / z: 446.2181 (theoretical value: 446.2166).

[0222] According to the above preparation method, the present invention also synthesizes the following intermediates:

[0223]

[0224]

[0225] Synthesis Example 3: Preparation of Compound 16

[0226]

[0227] Preparation of intermediate A-16: Under nitrogen protection, a-16 (14.52 g, 80.00 mmol), b-16 (13.04 g, 80.00 mmol), K2CO3 (16.58 g, 120.00 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), 400 mL toluene / ethanol / water (2:1:1) were added to the reaction bottle, and the mixture was stirred under reflux for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then the obtained solid was recrystallized with toluene / ethanol = 10:1 to obtain intermediate A-16 (17.11 g, yield 81%), HPLC purity ≧99.77%. Mass spectrum m / z: 262.9917 (theoretical value: 262.9905).

[0228] Preparation of intermediate B-16: Under nitrogen protection, intermediate A-16 (13.21 g, 50.00 mmol), c-16 (9.90 g, 50.00 mmol), Na2CO3 (7.95 g, 75.00 mmol), Pd(dppf)Cl2 (0.37 g, 0.50 mmol), 300 mL toluene / ethanol / water (2:1:1) were added to the reaction bottle, and the mixture was stirred under reflux for 5.5 hours. After the reaction, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then the obtained solid was recrystallized with toluene / ethanol = 9:1 to obtain intermediate B-16 (14.89 g, yield 78%), HPLC purity ≧ 99.86%. Mass spectrum m / z: 381.0928 (theoretical value: 381.0920).

[0229] Preparation of compound 16: Under nitrogen protection, add B-16 (11.46 g, 30.00 mmol), d-16 (11.11 g, 30.00 mmol), K2CO3 (6.22 g, 45.00 mmol), Pd(OAc)2 (0.07 g, 0.30 mmol), P(t-Bu)3 (0.06 g, 0.30 mmol), 200 mL toluene / ethanol / water (2:1:1) to the reaction bottle, stir and react under reflux conditions for 6 hours. After the reaction, the reaction mixture is cooled to room temperature, filtered, washed with distilled water, and then the obtained solid is recrystallized from toluene to obtain compound 16 (13.27 g, yield 75%), HPLC purity ≧99.96%, mass spectrum m / z: 589.2141 (theoretical value: 589.2154). Theoretical element content (%) C 42 H 27 N3O: C, 85.55; H, 4.62; N, 7.13. Measured element content (%): C, 85.52; H, 4.59; N, 7.18.

[0230] Synthesis Example 4: Preparation of Compound 30

[0231]

[0232] According to the same preparation method as in Synthesis Example 3, c-16 and d-16 were replaced by equimolar c-30 and d-30, respectively, to obtain compound 30 (14.14 g), HPLC purity ≧99.95%. Mass spectrum m / z: 645.2763 (theoretical value: 645.2780). Theoretical element content (%) C 46 H 35 N3O: C, 85.55; H, 5.46; N, 6.51. Measured element content (%): C, 85.53; H, 5.50; N, 6.48.

[0233] Synthesis Example 5: Preparation of Compound 54

[0234]

[0235] According to the same preparation method as in Synthesis Example 3, c-16 and d-16 were replaced by equal moles of c-54 and d1-54, respectively, to obtain compound 54 (14.38 g), HPLC purity ≧99.92%. Mass spectrum m / z: 665.2476 (theoretical value: 665.2467). Theoretical element content (%) C 48 H 31 N3O: C, 86.59; H, 4.69; N, 6.31. Measured element content (%): C, 86.62; H, 4.71; N, 6.26.

[0236] Synthesis Example 6: Preparation of Compound 80

[0237]

[0238] According to the same preparation method as in Synthesis Example 3, c-16 and d-16 were replaced by equimolar b-16 and d-80, respectively, to obtain compound 80 (14.00 g), HPLC purity ≧99.94%. Mass spectrum m / z: 630.2067 (theoretical value: 630.2056). Theoretical element content (%) C 43 H 26 N4O2: C, 81.89; H, 4.16; N, 8.88. Measured element content (%): C, 81.91; H, 4.12; N, 8.91.

[0239] Synthesis Example 7: Preparation of Compound 87

[0240]

[0241] According to the same preparation method as in Synthesis Example 3, c-16 and d-16 were replaced by equimolar b-16 and d-87, respectively, to obtain compound 87 (13.81 g), HPLC purity ≧99.98%. Mass spectrum m / z: 630.2075 (theoretical value: 630.2056). Theoretical element content (%) C 43 H 26 N4O2: C, 81.89; H, 4.16; N, 8.88. Measured element content (%): C, 81.84; H, 4.19; N, 8.90.

[0242] Synthesis Example 8: Preparation of Compound 99

[0243]

[0244] According to the same preparation method as in Synthesis Example 3, c-16 and d-16 were replaced by equimolar b-16 and d-99, respectively, to obtain compound 99 (13.83 g), HPLC purity ≧ 99.93%. Mass spectrum m / z: 631.2023 (theoretical value: 631.2008). Theoretical element content (%) C 42 H 25 N5O2: C, 79.86; H, 3.99; N, 11.09. Measured element content (%): C, 79.90; H, 3.94; N, 11.12.

[0245] Synthesis Example 9: Preparation of Compound 104

[0246]

[0247] According to the same preparation method as in Synthesis Example 3, c-16 and d-16 were replaced by equimolar b-16 and d-104, respectively, to obtain compound 104 (13.64 g), HPLC purity ≧99.96%. Mass spectrum m / z: 631.2016 (theoretical value: 631.2008). Theoretical element content (%) C 42 H 25 N5O2: C, 79.86; H, 3.99; N, 11.09. Measured element content (%): C, 79.84; H, 3.96; N, 11.13.

[0248] Synthesis Example 10: Preparation of Compound 116

[0249]

[0250] According to the same preparation method as in Synthesis Example 3, c-16 and d-16 were replaced by equimolar b-16 and d-116, respectively, to obtain compound 116 (13.89 g), HPLC purity ≧99.98%. Mass spectrum m / z: 680.2202 (theoretical value: 680.2212). Theoretical element content (%) C 47 H 28 N4O2: C, 82.92; H, 4.15; N, 8.23. Measured element content (%): C, 82.88; H, 4.20; N, 8.21.

[0251] Synthesis Example 11: Preparation of Compound 120

[0252]

[0253] According to the same preparation method as in Synthesis Example 3, b-16, c-16, and d-16 were replaced by equal moles of b-120, b-120, and d-120, respectively, to obtain compound 120 (14.84 g), HPLC purity ≧99.91%. Mass spectrum m / z: 716.3133 (theoretical value: 716.3151). Theoretical element content (%) C 49 H 40 N4O2: C, 82.10; H, 5.62; N, 7.82. Measured element content (%): C, 82.07; H, 5.60; N, 7.78.

[0254] Synthesis Example 12: Preparation of Compound 124

[0255]

[0256] According to the same preparation method as in Synthesis Example 3, c-16 and d-16 were replaced by equimolar amounts of b-16 and d-124, respectively, to obtain compound 124 (13.68 g), HPLC purity ≧99.94%. Mass spectrum m / z: 670.2360 (theoretical value: 670.2369). Theoretical element content (%) C 46 H 30 N4O2: C, 82.37; H, 4.51; N, 8.35. Measured element content (%): C, 82.41; H, 4.48; N, 8.33.

[0257] Synthesis Example 13: Preparation of Compound 125

[0258]

[0259] According to the same preparation method as in Synthesis Example 3, c-16 was replaced by an equal mole of b-16 to obtain compound 125 (12.65 g), HPLC purity ≧99.92%. Mass spectrum m / z: 554.1755 (theoretical value: 554.1743). Theoretical element content (%) C 37 H 22 N4O2: C, 80.13; H, 4.00; N, 10.10. Measured element content (%): C, 80.15; H, 4.02; N, 10.06.

[0260] Synthesis Example 14: Preparation of Compound 148

[0261]

[0262] According to the same preparation method as in Synthesis Example 3, c-16 and d-16 were replaced by equimolar amounts of b-16 and d-148, respectively, to obtain compound 148 (14.84 g), HPLC purity ≧99.97%. Mass spectrum m / z: 706.2383 (theoretical value: 706.2369). Theoretical element content (%) C 49 H 30 N4O2: C, 83.27; H, 4.28; N, 7.93. Measured element content (%): C, 83.30; H, 4.31; N, 7.89.

[0263] Synthesis Example 15: Preparation of Compound 154

[0264]

[0265] According to the same preparation method as in Synthesis Example 3, c-16 and d-16 were replaced by equal moles of b-16 and d-154, respectively, to obtain compound 154 (13.88 g), HPLC purity ≧99.91%. Mass spectrum m / z: 642.2801 (theoretical value: 642.2809). Theoretical element content (%) C 43 H 14 D 12 N4O2: C, 80.35; H, 5.96; N, 8.72. Measured element content (%): C, 80.38; H, 5.98; N, 8.67.

[0266] Synthesis Example 16: Preparation of Compound 155

[0267]

[0268] According to the same preparation method as in Synthesis Example 3, c-16 and d-16 were replaced by equimolar amounts of b-16 and d-155, respectively, to obtain compound 155 (15.38 g), HPLC purity ≧99.96%. Mass spectrum m / z: 742.3325 (theoretical value: 742.3308). Theoretical element content (%) C 51 H 42 N4O2: C, 82.45; H, 5.70; N, 7.54. Measured element content (%): C, 82.47; H, 5.66; N, 7.57.

[0269] Synthesis Example 17: Preparation of Compound 161

[0270]

[0271] According to the same preparation method as in Synthesis Example 3, b-16, c-16, and d-16 were replaced by equimolar b-161, b-161, and d-80, respectively, to obtain compound 161 (14.91 g), HPLC purity ≧99.93%. Mass spectrum m / z: 730.2356 (theoretical value: 730.2369). Theoretical element content (%) C 51 H 30 N4O2: C, 83.82; H, 4.14; N, 7.67. Measured element content (%): C, 83.80; H, 4.17; N, 7.65.

[0272] Synthesis Example 18: Preparation of Compound 168

[0273]

[0274] According to the same preparation method as in Synthesis Example 3, b-16 and c-16 were replaced by equal moles of b-168 and b-168, respectively, to obtain compound 168 (14.63 g), HPLC purity ≧99.94%. Mass spectrum m / z: 706.2353 (theoretical value: 706.2369). Theoretical element content (%) C 49 H 30 N4O2: C, 83.27; H, 4.28; N, 7.93. Measured element content (%): C, 83.30; H, 4.30; N, 7.88.

[0275] Synthesis Example 19: Preparation of Compound 181

[0276]

[0277] According to the same preparation method as in Synthesis Example 3, b-16 and c-16 were replaced by equal moles of b-181 and b-181, respectively, to obtain compound 181 (14.46 g), HPLC purity ≧99.99%. Mass spectrum m / z: 708.2282 (theoretical value: 708.2274). Theoretical element content (%) C 47 H 28 N6O2: C, 79.65; H, 3.98; N, 11.86. Measured element content (%): C, 79.63; H, 3.95; N, 11.90.

[0278] Synthesis Example 20: Preparation of Compound 213

[0279]

[0280] According to the same preparation method as in Synthesis Example 3, c-16 and d-16 were replaced by equal moles of b-16 and d1-213, respectively, to obtain compound 213 (13.68 g), HPLC purity ≧99.95%. Mass spectrum m / z: 680.2232 (theoretical value: 680.2212). Theoretical element content (%) C 47 H 28 N4O2: C, 82.92; H, 4.15; N, 8.23. Measured element content (%): C, 82.88; H, 4.18; N, 8.25.

[0281] Synthesis Example 21: Preparation of Compound 227

[0282]

[0283] According to the same preparation method as in Synthesis Example 3, c-16 and d-16 were replaced by equal moles of b-16 and d1-227, respectively, to obtain compound 227 (14.01 g), HPLC purity ≧ 99.92%. Mass spectrum m / z: 707.2337 (theoretical value: 707.2321). Theoretical element content (%) C 48 H 29 N5O2: C, 81.45; H, 4.13; N, 9.89. Measured element content (%): C, 81.47; H, 4.09; N, 9.92.

[0284] Synthesis Example 22: Preparation of Compound 261

[0285]

[0286] Preparation of intermediate A-261: Under nitrogen protection, a-261 (14.75 g, 80.00 mmol), b-168 (19.12 g, 80.00 mmol), K2CO3 (16.58 g, 120.00 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), 400 mL toluene / ethanol / water (2:1:1) were added to the reaction bottle, and the mixture was stirred under reflux for 4.5 hours. After the reaction, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then the obtained solid was recrystallized with toluene / ethanol = 9:1 to obtain intermediate A-261 (21.41 g, yield 78%), HPLC purity ≧ 99.82%. Mass spectrum m / z: 342.0056 (theoretical value: 342.0075).

[0287] Preparation of intermediate B-261: Under nitrogen protection, intermediate A-261 (17.16 g, 50.00 mmol), c-261 (10.15 g, 50.00 mmol), Na2CO3 (7.95 g, 75.00 mmol), Pd(dppf)Cl2 (0.37 g, 0.50 mmol), 300 mL toluene / ethanol / water (2:1:1) were added to the reaction bottle, and stirred for 6.5 hours under reflux conditions. After the reaction, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then the obtained solid was recrystallized with toluene / ethanol = 10:1 to obtain intermediate B-261 (17.47 g, yield 75%), HPLC purity ≧ 99.80%. Mass spectrum m / z: 465.1416 (theoretical value: 465.1405).

[0288] Preparation of compound 261: Under nitrogen protection, add B-261 (13.98 g, 30.00 mmol), d-16 (11.11 g, 30.00 mmol), K2CO3 (6.22 g, 45.00 mmol), Pd(OAc)2 (0.07 g, 0.30 mmol), P(t-Bu)3 (0.06 g, 0.30 mmol), 200 mL toluene / ethanol / water (2:1:1) to the reaction bottle, stir and react under reflux conditions for 7.5 hours. After the reaction, the reaction mixture is cooled to room temperature, filtered, washed with distilled water, and then the obtained solid is recrystallized from toluene to obtain compound 261 (14.76 g, yield 73%), HPLC purity ≧99.94%, mass spectrum m / z: 673.2623 (theoretical value: 673.2638). Theoretical element content (%) C 45 H 23 D5N6O: C, 80.22; H, 4.94; N, 12.47. Measured element content (%): C, 80.19; H, 4.96; N, 12.44.

[0289] Synthesis Example 23: Preparation of Compound 262

[0290]

[0291] According to the same preparation method as in Synthesis Example 22, c-261 and d-16 were replaced by equal moles of c-262 and d-262, respectively, to obtain compound 262 (15.64 g), HPLC purity ≧99.93%. Mass spectrum m / z: 744.2645 (theoretical value: 744.2638). Theoretical element content (%) C 51 H 32 N6O: C, 82.24; H, 4.33; N, 11.28. Measured element content (%): C, 82.22; H, 4.29; N, 11.31.

[0292] Synthesis Example 24: Preparation of Compound 263

[0293]

[0294] According to the same preparation method as in Synthesis Example 22, b-168, c-261, and d-16 were replaced by equal moles of b-263, c-263, and d-263, respectively, to obtain compound 263 (14.16 g), HPLC purity ≧99.91%. Mass spectrum m / z: 664.2417 (theoretical value: 664.2407). Theoretical element content (%) C 42 H 32 N6OSi: C, 75.88; H, 4.85; N, 12.64. Measured element content (%): C, 75.90; H, 4.82; N, 12.66.

[0295] Synthesis Example 25: Preparation of Compound 270

[0296]

[0297] According to the same preparation method as in Synthesis Example 22, c-261 and d-16 were replaced by equimolar c-270 and d-30, respectively, to obtain compound 270 (15.10 g), HPLC purity ≧99.97%. Mass spectrum m / z: 718.2461 (theoretical value: 718.2481). Theoretical element content (%) C 49 H 30 N6O: C, 81.88; H, 4.21; N, 11.69. Measured element content (%): C, 81.90; H, 4.16; N, 11.72.

[0298] Synthesis Example 26: Preparation of Compound 273

[0299]

[0300] According to the same preparation method as in Synthesis Example 22, c-261 and d-16 were replaced by equimolar c-273 and d-30, respectively, to obtain compound 273 (15.45 g), HPLC purity ≧99.95%. Mass spectrum m / z: 768.2649 (theoretical value: 768.2638). Theoretical element content (%) C 53 H 32 N6O: C, 82.79; H, 4.20; N, 10.93. Measured element content (%): C, 82.82; H, 4.16; N, 10.95.

[0301] Synthesis Example 27: Preparation of Compound 282

[0302]

[0303] According to the same preparation method as in Synthesis Example 22, b-168, c-261, and d-16 were replaced by equimolar amounts of b-16, c-282, and d-282, respectively, to obtain compound 282 (13.71 g), HPLC purity ≧99.98%. Mass spectrum m / z: 643.2130 (theoretical value: 643.2121). Theoretical element content (%) C 42 H 25 N7O: C, 78.37; H, 3.91; N, 15.23. Measured element content (%): C, 78.40; H, 3.89; N, 15.26.

[0304] Synthesis Example 28: Preparation of Compound 289

[0305]

[0306] According to the same preparation method as in Synthesis Example 22, b-168 and c-261 were replaced by equimolar b-289 and c-289, respectively, to obtain compound 289 (14.63 g), HPLC purity ≧ 99.93%. Mass spectrum m / z: 696.2260 (theoretical value: 696.2274). Theoretical element content (%) C 46 H 28 N6O2: C, 79.30; H, 4.05; N, 12.06. Measured element content (%): C, 79.26; H, 4.03; N, 12.11.

[0307] Synthesis Example 29: Preparation of Compound 306

[0308]

[0309] According to the same preparation method as in Synthesis Example 22, b-168, c-261, d-16 were replaced by equimolar b-306, c-16, d1-54, respectively, to obtain compound 306 (15.42 g), HPLC purity ≧ 99.92%. Mass spectrum m / z: 744.2622 (theoretical value: 744.2638). Theoretical element content (%) C 51 H 32 N6O: C, 82.24; H, 4.33; N, 11.28. Measured element content (%): C, 82.27; H, 4.29; N, 11.30.

[0310] Synthesis Example 30: Preparation of Compound 322

[0311]

[0312] According to the same preparation method as in Synthesis Example 22, c-261 and d-16 were replaced by equal moles of c-322 and d1-322, respectively, to obtain compound 322 (15.22 g), HPLC purity ≧99.94%. Mass spectrum m / z: 745.2570 (theoretical value: 745.2590). Theoretical element content (%) C 50 H 31 N7O: C, 80.52; H, 4.19; N, 13.15. Measured element content (%): C, 80.49; H, 4.22; N, 13.13.

[0313] Synthesis Example 31: Preparation of Compound 327

[0314]

[0315] According to the same preparation method as in Synthesis Example 22, c-261 and d-16 were replaced by equimolar c-168 and d-80, respectively, to obtain compound 327 (15.56 g), HPLC purity ≧99.90%. Mass spectrum m / z: 785.2550 (theoretical value: 785.2539). Theoretical element content (%) C 52 H 31 N7O2: C, 79.48; H, 3.98; N, 12.48. Measured element content (%): C, 79.51; H, 3.93; N, 12.50.

[0316] Synthesis Example 32: Preparation of Compound 337

[0317]

[0318] According to the same preparation method as in Synthesis Example 22, c-261 was replaced with an equal mole of b-168 to obtain compound 337 (14.48 g), HPLC purity ≧99.99%. Mass spectrum m / z: 709.2233 (theoretical value: 709.2226). Theoretical element content (%) C 46 H 27 N7O2: C, 77.84; H, 3.83; N, 13.81. Measured element content (%): C, 77.86; H, 3.85; N, 13.77.

[0319] Synthesis Example 33: Preparation of Compound 356

[0320]

[0321] According to the same preparation method as in Synthesis Example 22, c-261 and d-16 were replaced by equimolar amounts of b-168 and d1-322, respectively, to obtain compound 356 (15.80 g), HPLC purity ≧99.93%. Mass spectrum m / z: 785.2548 (theoretical value: 785.2539). Theoretical element content (%) C 52 H 31 N7O2: C, 79.48; H, 3.98; N, 12.48. Measured element content (%): C, 79.45; H, 3.96; N, 12.53.

[0322] Synthesis Example 34: Preparation of Compound 373

[0323]

[0324] According to the same preparation method as in Synthesis Example 3, b-16, c-16, and d-16 were replaced by equimolar amounts of b-373, b-373, and d-80, respectively, to obtain compound 373 (14.52 g) with HPLC purity ≧99.92%. Mass spectrum m / z: 662.1587 (theoretical value: 662.1599). Theoretical element content (%) C 43 H 26 N4S2: C, 77.92; H, 3.95; N, 8.45. Measured element content (%): C, 77.88; H, 3.97; N, 8.48.

[0325] Synthesis Example 35: Preparation of Compound 384

[0326]

[0327] According to the same preparation method as in Synthesis Example 3, b-16, c-16, and d-16 were replaced by equimolar amounts of b-373, b-373, and d-263, respectively, to obtain compound 384 (13.20 g), HPLC purity ≧99.94%. Mass spectrum m / z: 586.1293 (theoretical value: 586.1286). Theoretical element content (%) C 37 H 22 N4S2: C, 75.74; H, 3.78; N, 9.55. Measured element content (%): C, 75.72; H, 3.81; N, 9.53.

[0328] Synthesis Example 36: Preparation of Compound 394

[0329]

[0330] According to the same preparation method as in Synthesis Example 3, b-16 and c-16 were replaced by equal moles of b-394 and b-394 to obtain compound 394 (13.07 g), HPLC purity ≧99.97%. Mass spectrum m / z: 588.1177 (theoretical value: 588.1191). Theoretical element content (%) C 35 H 20 N6S2: C, 71.41; H, 3.42; N, 14.28. Measured element content (%): C, 71.39; H, 3.38; N, 14.32.

[0331] Synthesis Example 37: Preparation of Compound 446

[0332]

[0333] According to the same preparation method as in Synthesis Example 3, a-16, b-16, c-16, d-16 were replaced by equal moles of a-446, b-373, b-373, d1-446, respectively, to obtain compound 446 (15.61 g), HPLC purity ≧ 99.91%. Mass spectrum m / z: 732.2374 (theoretical value: 732.2381). Theoretical element content (%) C 48 H 36 N4S2: C, 78.66; H, 4.95; N, 7.64. Measured element content (%): C, 78.70; H, 4.92; N, 7.62.

[0334] Synthesis Example 38: Preparation of Compound 447

[0335]

[0336] According to the same preparation method as in Synthesis Example 3, b-16, c-16, and d-16 were replaced by equimolar amounts of b-373, c-447, and d-447, respectively, to obtain compound 447 (12.72 g) with HPLC purity ≧99.95%. Mass spectrum m / z: 580.1740 (theoretical value: 580.1722). Theoretical element content (%) C 39 H 24 N4S: C, 80.67; H, 4.17; N, 9.65. Measured element content (%): C, 80.70; H, 4.15; N, 9.63.

[0337] Synthesis Example 39: Preparation of Compound 466

[0338]

[0339] According to the same preparation method as in Synthesis Example 22, b-168, c-261, and d-16 were replaced by equal moles of b-466, b-466, and d1-466, respectively, to obtain compound 466 (15.95 g), HPLC purity ≧99.92%. Mass spectrum m / z: 817.2090 (theoretical value: 817.2082). Theoretical element content (%) C 52 H 31 N7S2: C, 76.35; H, 3.82; N, 11.99. Measured element content (%): C, 76.40; H, 3.79; N, 11.96.

[0340] Synthesis Example 40: Preparation of Compound 482

[0341]

[0342] According to the same preparation method as in Synthesis Example 22, b-168, c-261, and d-16 were replaced by equal moles of b-482, c-482, and d1-54, respectively, to obtain compound 482 (16.10 g), HPLC purity ≧99.98%. Mass spectrum m / z: 800.2709 (theoretical value: 800.2722). Theoretical element content (%) C 54 H 36 N6S: C, 80.97; H, 4.53; N, 10.49. Measured element content (%): C, 80.95; H, 4.51; N, 10.52.

[0343] Synthesis Example 41: Preparation of Compound 517

[0344]

[0345] According to the same preparation method as in Synthesis Example 22, a-261, b-168, c-261, d-16 were replaced by equal moles of a-517, b-16, b-16, d-80, respectively, to obtain compound 517 (13.46 g), HPLC purity ≧ 99.93%. Mass spectrum m / z: 631.2025 (theoretical value: 631.2008). Theoretical element content (%) C 42 H 25 N5O2: C, 79.86; H, 3.99; N, 11.09. Measured element content (%): C, 79.81; H, 3.97; N, 11.13.

[0346] Synthesis Example 42: Preparation of Compound 582

[0347]

[0348] According to the same preparation method as in Synthesis Example 22, a-261, b-168, c-261, d-16 were replaced by equal moles of a-582, b-482, b-482, d1-582, respectively, to obtain compound 582 (15.54 g), HPLC purity ≧ 99.96%. Mass spectrum m / z: 821.2432 (theoretical value: 821.2444). Theoretical element content (%) C 53 H 27 D5N6S2: C, 77.44; H, 4.54; N, 10.22. Measured element content (%): C, 77.42; H, 4.56; N, 10.19.

[0349] Device Embodiment

[0350] In the present invention, the ITO glass substrate and the ITO / Ag / ITO glass substrate are ultrasonically cleaned twice with 5% glass cleaning liquid for 20 minutes each time, and then ultrasonically cleaned twice with deionized water for 10 minutes each time. Acetone and isopropyl ketone are ultrasonically cleaned for 20 minutes in sequence, and dried at 120°C. The organic materials are all sublimated, and the purity is above 99.99%.

[0351] The test software, computer, K2400 digital source meter produced by Keithley Company of the United States and PR788 spectrum scanning luminance meter produced by PhotoResearch Company of the United States are combined into a joint IVL test system to test the driving voltage, luminous efficiency and CIE color coordinates of organic electroluminescent devices. The life test adopts the M6000 OLED life test system of McScience Company. The test environment is atmospheric environment and the temperature is room temperature.

[0352] Example 1: Preparation of organic electroluminescent device 1

[0353] HI-1:HI-2=5:95 (wt%) was vacuum-deposited on the ITO anode as a hole injection layer with a thickness of 12 nm; HT-1 was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 120 nm; GH-1:compound of the present invention 16:GD-1=46:46:8 (wt%) was vacuum-deposited on the hole transport layer to form a light-emitting layer with a thickness of 32 nm; ET-1:LiQ=1:1 (wt%) was vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 35 nm; LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1.0 nm; Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 110 nm.

[0354] Examples 2 to 40: Preparation of organic electroluminescent devices 2 to 40

[0355] The compound 16 in the light-emitting layer of Example 1 is replaced by compound 30, compound 54, compound 80, compound 87, compound 99, compound 104, compound 116, compound 120, compound 124, compound 125, compound 148, compound 154, compound 155, compound 161, compound 168, compound 181, compound 213, compound 227, compound 261, compound 262, compound 263, compound 270, compound 273, compound 282, compound 289, compound 306, compound 322, compound 327, compound 337, compound 356, compound 373, compound 384, compound 394, compound 446, compound 447, compound 466, compound 482, compound 517, and compound 582, respectively, and the other steps are the same to obtain organic electroluminescent devices 2 to 40.

[0356] Comparative Examples 1 to 3: Preparation of Comparative Organic Electroluminescent Devices 1 to 3

[0357] The compound 16 in the light-emitting layer of Example 1 was replaced by R-1, R-2, and R-3 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 1 to 3.

[0358]

[0359] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 1 to 40 of the present invention and Comparative Examples 1 to 3 are shown in Table 1.

[0360] Table 1 Test data of luminescence characteristics of organic electroluminescent devices

[0361]

[0362]

[0363]

[0364] Note: T97 refers to the current density of 10mA / cm 2 Under the condition of , the time taken by the device brightness to decay to 97%;

[0365] As can be seen from Table 1, the organic electroluminescent device containing the heterocyclic compound of Formula 1 of the present invention in the light-emitting layer has a lower driving voltage, higher luminous efficiency and longer service life than the comparative device, and the performance of the organic electroluminescent device is more excellent. The heterocyclic compound of Formula 1 of the present invention is an excellent main material for the light-emitting layer.

[0366] Example 41: Preparation of organic electroluminescent device 41

[0367] HI-1:HI-2=5:95 (wt%) was vacuum-deposited on the ITO anode as a hole injection layer with a thickness of 10 nm; HT-2 was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 120 nm; RH-1:RH-2:RD-1=49:49:2 (wt%) was vacuum-deposited on the hole transport layer to form a light-emitting layer with a thickness of 35 nm; the compound of the present invention 16:LiQ=1:1 (wt%) was vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 30 nm; LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1.0 nm; Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 110 nm.

[0368] Examples 42 to 67: Preparation of organic electroluminescent devices 42 to 67

[0369] The compound 16 in the electron transport layer of Example 41 is replaced by compound 30, compound 80, compound 87, compound 99, compound 104, compound 116, compound 125, compound 168, compound 181, compound 213, compound 261, compound 262, compound 263, compound 270, compound 282, compound 289, compound 306, compound 322, compound 327, compound 337, compound 356, compound 373, compound 384, compound 466, compound 482, and compound 517, respectively, and the other steps are the same to obtain organic electroluminescent devices 42 to 67.

[0370] Comparative Examples 4-5: Preparation of Comparative Organic Electroluminescent Devices 4-5

[0371] The compound 16 in the electron transport layer of embodiment 41 was replaced by R-4 and R-5 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 4~5.

[0372]

[0373] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 41 to 67 of the present invention and Comparative Examples 4 to 5 are shown in Table 2.

[0374] Table 2 Test data of luminescence characteristics of organic electroluminescent devices

[0375]

[0376] Note: T95 refers to the current density of 10mA / cm 2 Under the condition, the time taken for the device brightness to decay to 95%;

[0377] It can be seen from Table 2 that, compared with comparative devices 4 to 5, the organic electroluminescent device containing the heterocyclic compound of Formula 1 of the present invention in the electron transport layer has better device performance, specifically, lower driving voltage, higher luminous efficiency and longer service life.

[0378] Example 68: Preparation of organic electroluminescent device 68

[0379] HI-1:HI-2=5:95 (wt%) was vacuum evaporated on the ITO / Ag / ITO anode as a hole injection layer with a thickness of 10 nm; HT-3 was vacuum evaporated on the hole injection layer as a hole transport layer with a thickness of 120 nm; BH-1:BD-1=95:5 (wt%) was vacuum evaporated on the hole transport layer to form a light-emitting layer with a thickness of 35 nm; ET-1:LiQ=1:1 (wt%) was vacuum evaporated on the light-emitting layer as an electron transport layer with a thickness of 30 nm; LiF was vacuum evaporated on the electron transport layer as an electron injection layer with a thickness of 1.1 nm; Mg:Ag=10:90 (wt%) was vacuum evaporated on the electron injection layer as a cathode with a thickness of 10 nm; and the compound 80 of the present invention was vacuum evaporated on the cathode as a covering layer with a thickness of 73 nm.

[0380] Examples 69 to 81: Preparation of organic electroluminescent devices 69 to 81

[0381] The compound 80 in the covering layer of Example 68 is replaced by compound 99, compound 104, compound 161, compound 168, compound 181, compound 261, compound 270, compound 327, compound 337, compound 348, compound 356, compound 373, compound 394, and compound 582, respectively, and the other steps are the same to obtain organic electroluminescent devices 69 to 81.

[0382] Comparative Examples 6-7: Preparation of Comparative Organic Electroluminescent Devices 6-7

[0383] The compound 80 in the covering layer of Example 68 was replaced by R-6 and R-7 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 6 to 7.

[0384]

[0385] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 68 to 81 of the present invention and Comparative Examples 6 to 7 are shown in Table 3.

[0386] Table 3 Test data of luminescence characteristics of organic electroluminescent devices

[0387]

[0388]

[0389] Note: T95 refers to the current density of 10mA / cm 2 Under the condition, the time taken for the device brightness to decay to 95%;

[0390] It can be seen from Table 3 that, compared with comparative devices 6 to 7, the organic electroluminescent device containing the heterocyclic compound of Formula 1 of the present invention in the covering layer has better performance, higher luminous efficiency and longer service life. The heterocyclic compound of Formula 1 of the present invention is a good covering layer material.

[0391] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. A heterocyclic compound, characterized in that It is represented by the following formula 1: Wherein, the x is the same or different and is selected from CR a or N; The R a One selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring; Ar0 is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring fused ring, or the N atom corresponding to Ar0 is the connection site with L1; The R1 and R2 are the same or different and are selected from one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, and substituted or unsubstituted C3-C20 cycloalkyl; The n1 is the same or different and is selected from 0, 1, 2, 3 or 4; The L0 is selected from the group shown in the following formula 1-a, The v is the same or different from CR b or N, and at least one v is selected from N, and the v bonded to L1 and L2 is selected from C atoms; The R b is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or two adjacent R b Bonding to form a substituted or unsubstituted benzene ring or nitrogen-containing heterocyclic ring; Said b1 is selected from 1, 2 or 3; The L1 and L2 are the same or different and are selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring sub-condensed ring group; Said Y is selected from O or S; The z are the same or different and are selected from CH or N; The R3 is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R3 are bonded to form a substituted or unsubstituted ring; The m1 is selected from 0, 1, 2, 3 or 4; Ar1 is selected from one or a combination of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring; The L3 is selected from a single bond, a substituted or unsubstituted C2-C30 heteroarylene group or one of the groups shown below, The y is the same or different and is selected from CR 11 ; The R 11 is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or two adjacent R 11 Bonding to form substituted or unsubstituted alicyclic rings; The W is selected from CR 12 R 13 ; The R 12 , R 13 The same or different R is selected from hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or adjacent R 12 , R 13 Bonding to form a substituted or unsubstituted ring; The L4 is selected from one or a combination of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, and a substituted or unsubstituted C3-C20 alicyclic group and C6-C30 aromatic ring condensed group.

2. The heterocyclic compound according to claim 1, characterized in that The Ar0 is selected from one of the following groups: The e is the same or different from CR c or N; The Q is selected from O, S, CR d R e or NR f ; Q1 is selected from O, S or NR g ; Q2 is selected from CR i or N; The R c is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or two adjacent R c Bonding to form a substituted or unsubstituted ring; The R d , R e The same or different R is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or adjacent R d , R e Bonding to form a substituted or unsubstituted ring; The R i One selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring; The R f , R g The same or different ones are selected from substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring.

3. The heterocyclic compound according to claim 1, characterized in that The L0 is selected from one of the following groups: The R b the same or different selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl; The d1 is selected from 0, 1, 2 or 3; the d2 is selected from 0, 1 or 2; the d3 is selected from 0 or 1; the d4 is selected from 0, 1, 2, 3, 4 or 5; the d5 is selected from 0, 1, 2, 3 or 4; the d6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the d7 is selected from 0, 1, 2, 3, 4, 5 or 6.

4. The heterocyclic compound according to claim 1, characterized in that The L1 and L2 are the same or different and are selected from a single bond or one of the following groups: The R4 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, or a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, or two adjacent R4 are bonded to form a substituted or unsubstituted benzene ring; Said a1 is selected from 0, 1, 2, 3 or 4; said a2 is selected from 0, 1, 2, 3, 4, 5 or 6; said a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said a4 is selected from 0, 1, 2 or 3; said a5 is selected from 0, 1 or 2; said a6 is selected from 0, 1, 2, 3, 4 or 5; said a7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

5. The heterocyclic compound according to claim 1, characterized in that Said One selected from the following groups, The R3 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylmethyl Silyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent R3 are bonded to form a substituted or unsubstituted benzene ring; The m1 is selected from 0, 1, 2, 3 or 4; the m2 is selected from 0, 1, 2 or 3; the m3 is selected from 0, 1 or 2; the m4 is selected from 0 or 1; the m5 is selected from 0, 1, 2, 3, 4, 5 or 6; the m6 is selected from 0, 1, 2, 3, 4 or 5; the m7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the m8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

6. The heterocyclic compound according to claim 1, characterized in that The Ar1 is selected from one of the following groups: The u are the same or different and are selected from CR5 or N; The T is selected from O, S, CR6R7 or NR8; the T1 is selected from O, S or NR9; the T2 is selected from CR 10 or N; The R5 is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R5 are bonded to form a substituted or unsubstituted ring; The R6 and R7 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or adjacent R6 and R7 are bonded to form a substituted or unsubstituted C3-C7 ring; The R8 and R9 are the same or different and are selected from a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, or a fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring; The R 10 One selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring.

7. The heterocyclic compound according to claim 1, characterized in that The L4 are the same or different and are selected from a single bond or one of the groups shown below, The R h the same or different selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent R h Bonding to form a substituted or unsubstituted ring; The t1 is selected from 0, 1, 2, 3 or 4; the t2 is selected from 0, 1, 2, 3, 4, 5 or 6; the t3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the t4 is selected from 0, 1, 2 or 3; the t5 is selected from 0, 1 or 2; the t6 is selected from 0 or 1; the t7 is selected from 0, 1, 2, 3, 4 or 5; the t8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the t9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

8. The heterocyclic compound according to claim 1, characterized in that The heterocyclic compound is selected from one of the structures shown below:

9. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode, a cathode and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains the heterocyclic compound according to any one of claims 1 to 8.

10. The organic electroluminescent device according to claim 9, characterized in that: The organic layer is located between the anode and the cathode, and includes at least one of a light-emitting layer and an electron transport region, and at least one of the light-emitting layer and the electron transport region contains the heterocyclic compound according to any one of claims 1 to 8.

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