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 proper energy level and high electron mobility, and can balance electrons and holes in a light-emitting layer, improve the exciton recombination efficiency, further reduce the driving voltage of the device, improve the light-emitting efficiency of the device and prolong the service life of the device as a main material of the light-emitting layer in the organic light-emitting device. Meanwhile, as an electron transport region material, the compound disclosed by the invention not only can improve the electron transport efficiency, but also can prevent a hole from migrating to an electron transport region, thereby improving the performance of the organic electroluminescent device. The compound provided by the invention also has good thermal stability and film-forming property, and is an excellent 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) have many characteristics such as full solid state, light weight, fast response speed, high luminous efficiency, high resolution, low power consumption, and flexible display, and have attracted widespread attention. Its working principle is that under voltage drive, carriers are injected from the positive and negative electrodes, and the carriers are transferred between organic molecules in the organic functional layer and move to the light-emitting layer. The carriers recombine in the light-emitting layer to form excitons, and then the excitons migrate to transfer energy, thereby emitting light.

[0003] The organic functional layer in the organic electroluminescent device mainly includes a multilayer structure such as a hole transport region, a light-emitting layer, an electron transport region, and a covering layer. Among them, the light-emitting layer plays a vital role. The light-emitting layer mainly includes a host material and a guest material. The host material needs to capture the electrons and holes migrated from the carrier transport layer, and migrate to the LUMO and HOMO energy levels to recombine into excitons, and then the energy is transferred. The design of the host material needs to meet the following points: the triplet energy level of the host material is greater than the guest material, which can avoid energy backflow; the HOMO\LUMO energy level of the host material should match the energy level of the hole transport region and the electron transport region, respectively, which helps to reduce the injection barrier of holes and electrons and capture carriers; the carrier transfer rate is high, which helps the recombination of excitons and the widening of their recombination area; the stability and film-forming properties of the host material itself are good, which is conducive to the formation of a uniform and stable film. However, many of the current host materials do not meet the market demand, and there are still problems such as energy level mismatch, low carrier transfer rate and low stability, which need to be further improved. In addition, the transmission balance of electrons and holes is also a key factor affecting the performance of organic electroluminescent devices. However, in organic electroluminescent devices, the electron transfer rate is often much lower than the hole transfer rate, resulting in an unbalanced transfer of electrons and holes within the device, which reduces the performance of the device.

[0004] Therefore, in order to effectively improve the performance of organic electroluminescent devices, it is necessary to develop light-emitting layer host materials and electron transport materials with better performance. Summary of the invention

[0005] In view of the problems existing in the prior art, the present invention provides a heterocyclic compound and an organic electroluminescent device thereof.

[0006] The present invention provides a heterocyclic compound represented by the following formula 1:

[0007]

[0008] Wherein, the x is the same or different and is selected from CR 0 or N, and at least one x is selected from N and is identical to L 1 , L 2 , L 3 The bonded x is selected from C atoms;

[0009] The R 0 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;

[0010] The Ar 1 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 fused C6-C30 aromatic ring, or Ar 1 The corresponding N atom is 1 The attachment site of

[0011] The ring A is selected from a substituted or unsubstituted C2-C30 nitrogen-containing heterocycle;

[0012] The ring B is selected from a substituted or unsubstituted C6-C30 aromatic ring;

[0013] Said Y is selected from O or S;

[0014] The z are the same or different and are selected from CH or N;

[0015] The R 3 the same or different selected from hydrogen, deuterium, cyano, 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 3 Bonding to form a substituted or unsubstituted ring;

[0016] The m 1 Selected from 0, 1, 2, 3 or 4;

[0017] The Ar 3 One selected from the following groups,

[0018]

[0019] The u is the same or different from CR 5 or N;

[0020] The Q is selected from O, S, CR 6 R 7 or NR 8 ; Q 1 Selected from O, S or NR 9 ; Q 2 Selected from N;

[0021] The R 5 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 5 Bonding to form a substituted or unsubstituted ring;

[0022] The R 6 , R 7 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 6 , R 7 Bonding to form a substituted or unsubstituted ring;

[0023] The R 8 , R 9 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, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring;

[0024] The L 1 , L 2 , L 3 The same or different ones are selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring condensed ring group or a combination thereof.

[0025] The present invention also provides an organic electroluminescent device, which contains the heterocyclic compound of the present invention.

[0026] Beneficial effects: The heterocyclic compound of the present invention has a suitable energy level and high electron mobility. When used as a main material of the light-emitting layer in an organic electroluminescent device, it can effectively balance electrons and holes, improve the exciton recombination efficiency, further reduce the driving voltage of the device, improve the luminous efficiency of the device, and extend the service life of the device. At the same time, as an electron transport region material, the compound of the present invention can not only improve the electron transport efficiency, but also prevent the migration of holes to the electron transport region, thereby improving the performance of the organic electroluminescent device. The compound of the present invention also has good thermal stability and film-forming properties, and is an excellent covering layer material. DETAILED DESCRIPTION

[0027] 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.

[0028] In the compounds of the present invention, any atom not designated as a particular isotope includes any stable isotope of that atom, and includes the atom in both its natural isotopic abundance and unnatural abundance.

[0029] The halogen described in the present invention includes fluorine, chlorine, bromine and iodine.

[0030] 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.

[0031] 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.

[0032] 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 rings. For example, Can be expressed Can be expressed And so on.

[0033] 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.

[0034] 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:

[0035]

[0036] 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.

[0037] 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.

[0038] 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.

[0039] The silyl group described in the present invention refers to -Si(Rk ) 3 A group in which 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 k The 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] The present invention provides a heterocyclic compound represented by the following formula 1:

[0048]

[0049] Wherein, the x is the same or different and is selected from CR 0 or N, and at least one x is selected from N and is identical to L 1 , L 2 , L 3 The bonded x is selected from C atoms;

[0050] The R 0One 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;

[0051] The Ar 1 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 fused C6-C30 aromatic ring, or Ar 1 The corresponding N atom is 1 The attachment site of

[0052] The ring A is selected from a substituted or unsubstituted C2-C30 nitrogen-containing heterocycle;

[0053] The ring B is selected from substituted or unsubstituted C6-C30 aromatic rings;

[0054] Said Y is selected from O or S;

[0055] The z are the same or different and are selected from CH or N;

[0056] The R 3 the same or different selected from hydrogen, deuterium, cyano, 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 3 Bonding to form a substituted or unsubstituted ring;

[0057] The m 1 Selected from 0, 1, 2, 3 or 4;

[0058] The Ar 3 One selected from the following groups,

[0059]

[0060] The u is the same or different from CR 5 or N;

[0061] The Q is selected from O, S, CR 6 R 7 or NR 8 ; Q 1 Selected from O, S or NR9 ; Q 2 Selected from N;

[0062] The R 5 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 5 Bonding to form a substituted or unsubstituted ring;

[0063] The R 6 , R 7 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 6 , R 7 Bonding to form a substituted or unsubstituted ring;

[0064] The R 8 , R 9 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, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring;

[0065] The L 1 , L 2 , L 3 The same or different ones are selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring condensed ring group or a combination thereof.

[0066] Preferably, the One selected from the following groups,

[0067]

[0068] The R 0the 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;

[0069] The b 1 is selected from 0, 1 or 2; said b 2 Select from 0 or 1.

[0070] Preferably, the One selected from the following groups,

[0071]

[0072] The R 0 The same or different selected from hydrogen, deuterium, cyano, halogen, nitro, one of the following groups substituted or unsubstituted by one or more deuteriums, 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, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilane yl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, and quinoxalinyl.

[0073] Preferably, the ring A is selected from one of the groups shown in c-12 to c-22, and the ring B is selected from one of the groups shown in c-1 to c-11.

[0074]

[0075] The v is the same or different from CR 2 or N, and at least one v is selected from N;

[0076] The R 1 The same or different ones 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;

[0077] The R 2 The same or different ones 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;

[0078] The 1 is selected from 0, 1, 2, 3 or 4; said n 2 is selected from 0, 1, 2, 3, 4, 5 or 6; said n 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0079] Preferably, the One selected from the following groups,

[0080]

[0081] The R 1 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;

[0082] The R 2the 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;

[0083] The 1 is selected from 0, 1, 2, 3 or 4; said n 2 is selected from 0, 1, 2, 3, 4, 5 or 6; said n 3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said n 4 is selected from 0, 1, 2 or 3; said n 5 is selected from 0, 1, 2, 3, 4 or 5; said n 6 Select from 0, 1 or 2.

[0084] Preferably, the R 1 , R 2 The "substituted or unsubstituted" substituent is selected from hydrogen, 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 The compounds described herein include benzothiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl and quinoxalinyl.

[0085] Preferably, the Ar 1 One selected from the following groups,

[0086]

[0087] The e is the same or different from CR c or N;

[0088] The W is selected from O, S, CR a R b or NR d ; said W 1 Selected from O, S or NR f ; said W 2 Selected from CR g or N;

[0089] 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;

[0090] The R a , R b 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 a , R b Bonding to form a substituted or unsubstituted ring;

[0091] The R g 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;

[0092] The R d , R f 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.

[0093] Preferably, the Ar 1 One selected from the following groups,

[0094]

[0095] 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 R c Bonding to form substituted or unsubstituted benzene rings;

[0096] The R a , 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, 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;

[0097] The R d , R fthe same or different selected from the group consisting of substituted or unsubstituted groups 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, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl;

[0098] The d 1 is selected from 0, 1, 2, 3, 4 or 5; said d 2 is selected from 0, 1, 2, 3 or 4; said d 3 is selected from 0, 1, 2 or 3; said d 4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said d 5 is selected from 0, 1, 2, 3, 4, 5 or 6; said d 6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said d 7 is selected from 0, 1 or 2; said d 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0099] Preferably, the R a , R b , R c , R d , R f The "substituted or unsubstituted" substituent is selected from hydrogen, deuterium, cyano, halogen, nitro, and one of the following groups 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, triethylsilane yl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, and quinoxalinyl.

[0100] Preferably, the One selected from the following groups,

[0101]

[0102]

[0103] Said Y is selected from O or S;

[0104] The R 3 the same or different selected from hydrogen, deuterium, cyano, 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, 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, or two adjacent R 3 Bonding to form substituted or unsubstituted benzene rings;

[0105] The m 1 is selected from 0, 1, 2, 3 or 4; said m 2 is selected from 0, 1, 2 or 3; said m 3 is selected from 0, 1 or 2; said m 4 is selected from 0 or 1; said m 5 is selected from 0, 1, 2, 3, 4, 5 or 6; said m 6 is selected from 0, 1, 2, 3, 4 or 5; said m 7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said m 8 Selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0106] Preferably, the One selected from the following groups,

[0107]

[0108] The R 3The same or different selected from hydrogen, deuterium, cyano, 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, triethylsilyl , triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl.

[0109] Preferably, the Ar 3 One selected from the following groups,

[0110]

[0111] The R 5 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 5 Bonding to form a substituted or unsubstituted ring;

[0112] The R 6 , R 7the 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;

[0113] The R 8 , R 9 the same or different selected from the group consisting of substituted or unsubstituted groups 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, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl;

[0114] The c 1 is selected from 0, 1, 2, 3, 4 or 5; said c 2 is selected from 0, 1, 2, 3 or 4; said c 3 is selected from 0, 1, 2 or 3; said c 4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said c 5 is selected from 0, 1, 2, 3, 4, 5 or 6; said c 6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said c 7 is selected from 0, 1 or 2; said c 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0115] Preferably, the R 5 , R 6 , R 7 , R 8 , R9 The "substituted or unsubstituted" substituent is selected from hydrogen, 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 The compounds described herein include benzothiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl and quinoxalinyl.

[0116] Preferably, the L 1 , L 2 , L 3 The same or different ones are selected from a single bond or one of the groups shown below,

[0117]

[0118]

[0119] 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;

[0120] The 1 is selected from 0, 1, 2, 3 or 4; said t 2 is selected from 0, 1, 2, 3, 4, 5 or 6; said t 3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said t4 is selected from 0, 1, 2 or 3; said t 5 is selected from 0, 1 or 2; said t 6 is selected from 0 or 1; said t 7 is selected from 0, 1, 2, 3, 4 or 5; said t 8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said t 9 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0121] Preferably, the R h The "substituted or unsubstituted" substituent is selected from hydrogen, deuterium, cyano, halogen, nitro, and one of the following groups 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, triethylsilane yl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, and quinoxalinyl.

[0122] Preferably, the heterocyclic compound is selected from one of the structures shown below:

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144] 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.

[0145] In addition, the present invention also provides an organic electroluminescent device, wherein the organic electroluminescent device contains the heterocyclic compound of the present invention.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] 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.

[0154] 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.

[0155] 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.

[0156] 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.

[0157] 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.

[0158] 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.

[0159] 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.

[0160] 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.

[0161] Preferably, the N-type charge generation layer can be formed by doping the heterocyclic compound described in the present invention with other materials.

[0162] 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.

[0163] 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:

[0164] 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 silver (Ag), zinc (Zn), indium zinc oxide (IZO), indium tin oxide (ITO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polyaniline, etc., but not limited thereto.

[0165] The hole injection layer of the present invention preferably has a material with good hole injection ability. The hole injection layer material includes arylamine derivatives, perylene derivatives, hexanitrile hexaazatriphenylene compounds, anthraquinone compounds, etc., but is 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.

[0166] 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, benzidine derivatives, 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), etc., but are not limited thereto.

[0167] 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.

[0168] The light-emitting layer described in 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), 9,10-di(2-naphthyl)anthracene (ADN), etc., but are not limited thereto. The heterocyclic compound described in the present invention is preferred. The heterocyclic compound described in the present invention can be used alone as a host material or in combination with a p-type host material. The guest material comprises aromatic amine derivatives, boron complexes, metal complexes, etc., but is not limited thereto. Specific examples may include tri(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-phenylisoquinoline)(acetylacetonate)iridium (Ir(piq) 2 (acac)), tris(1-phenylisoquinolinol)iridium (Ir(piq)3 ), 2,5,8,11-tetra-tert-butylperylene (TBPe), etc., but not limited thereto.

[0169] 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.

[0170] 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 (Alq 3 ), 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 not limited thereto. The heterocyclic compound described in the present invention is preferred.

[0171] The electron injection layer of the present invention is preferably made of 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), 8-hydroxyquinoline lithium (LiQ), calcium fluoride (CaF 2 ), lithium oxide (Li 2 O) etc., but not limited thereto.

[0172] 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, etc., but is not limited thereto. Specific examples may include aluminum (Al), lithium (Li), magnesium (Mg), magnesium-silver alloy (Mg / Ag), etc., but are not limited thereto.

[0173] The cover material of the present invention is preferably a material with excellent light extraction performance, and the cover material includes aromatic amine derivatives, metal compounds, carbazole derivatives, etc., but is not limited thereto. Specific examples may include tris(8-hydroxyquinoline)aluminum (Alq 3 ), 4,4'-bis(carbazol-9-yl)biphenyl (CBP), etc., but not limited thereto. The heterocyclic compound described in the present invention is preferred.

[0174] The charge generation material of the present invention can be divided into an N-type charge generation material and a P-type charge generation material. Specific examples of the N-type charge generation material of the present invention may include tris-(8-hydroxyquinoline)aluminum (Alq 3), bis(2-methyl-8-quinolinato-N1,O8)-(1,1'-biphenyl-4-phenolato)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), etc., or doped with alkali metals or alkaline earth metals, but not limited thereto. The heterocyclic compounds described in the present invention are preferred. Specific examples of the P-type charge generating materials 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 not limited thereto.

[0175] 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.

[0176] 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.

[0177] 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.

[0178] Synthesis Example

[0179] 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.

[0180] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube organic element analyzer (Elementar, Germany).

[0181] 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-carbon coupling reaction, carbon-nitrogen coupling reaction, etc. The heterocyclic compound represented by Formula 1 of the present invention can be prepared by the synthetic route shown below.

[0182] Intermediate Synthesis Route 1:

[0183]

[0184] Intermediate Synthesis Route 2:

[0185]

[0186] Synthetic route 1 of the compound of formula 1: and At the same time, the synthetic route is as follows:

[0187]

[0188] Synthetic route 2 of the compound of formula 1: and At the same time, the synthetic route is as follows:

[0189]

[0190] The Xn is a halogen, and the Xn are the same or different and are selected from one of Cl, Br, and I;

[0191] The A is the same or different and is selected from *-B(OH) 2 or

[0192] The ring A, ring B, Ar 1 , L 1 , L 2 , L 3 ,Ar 3 , Y, x, z, R 3 、m 1 Same as above restrictions.

[0193] Synthesis Example 1: Preparation of Intermediate d-5

[0194]

[0195] Preparation of intermediate g-5: Under nitrogen protection, e-5 (15.14 g, 90.00 mmol), f-5 (17.23 g, 90.00 mmol), Pd(OAc) were added to the reaction bottle. 2 (0.20 g, 0.90 mmol), P(t-Bu) 3 (0.36g, 1.80mmol), sodium tert-butoxide (17.30g, 180.00mmol) and 700ml toluene solvent, stir the mixture, and heat the mixed solution of the above reactants under reflux for 5h. After the reaction is completed, cool to room temperature, add distilled water, extract with dichloromethane, stand and separate, collect the organic layer, dry it with anhydrous magnesium sulfate, filter, concentrate the filtrate by vacuum distillation, cool and crystallize, filter, and recrystallize the obtained solid with toluene: methanol = 9:1 to obtain intermediate g-5 (20.32g, yield 81%); HPLC purity ≧99.68%. Mass spectrum m / z: 278.0623 (theoretical value: 278.0611).

[0196] Preparation of intermediate d-5: Under nitrogen protection, g-5 (16.72 g, 60.00 mmol), biboric acid pinacol ester (15.24 g, 60.00 mmol), Na 2 CO 3 (12.72g, 120.00mmol), Pd(PPh 3 ) 4 (0.69 g, 0.60 mmol) and 360 mL DMF were 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-5 (17.33 g, yield 78%); HPLC purity ≧99.87%. Mass spectrum m / z: 370.1842 (theoretical value: 370.1853).

[0197] According to the above preparation method, the present invention also synthesizes the following intermediates:

[0198]

[0199]

[0200]

[0201] Synthesis Example 2: Preparation of Intermediate d1-191

[0202]

[0203] Preparation of intermediate g1-191: Under nitrogen protection, e1-191 (29.62 g, 80.00 mmol), f-5 (15.32 g, 80.00 mmol), K 2 CO 3 (16.58g, 120.00mmol), Pd(PPh 3 ) 4 (0.92 g, 0.80 mmol), 450 mL toluene / ethanol / water (2:1:1), 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 from toluene / ethanol = 10:1 to obtain intermediate g1-191 (21.57 g, yield 76%), HPLC purity ≧ 99.81%. Mass spectrum m / z: 354.0933 (theoretical value: 354.0924).

[0204] Preparation of intermediate d1-191: Under nitrogen protection, g1-191 (17.74 g, 50.00 mmol), biboric acid pinacol ester (12.70 g, 50.00 mmol), Na 2 CO 3 (10.60g, 100.00mmol), Pd(dppf)Cl 2 (0.37 g, 0.50 mmol) and 300 mL DMF were 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, and the solvent was concentrated by distillation under reduced pressure. The mixture was cooled and crystallized, filtered, and then recrystallized from ethyl acetate to obtain intermediate d1-191 (16.52 g, yield 74%); HPLC purity ≧99.83%. Mass spectrum m / z: 446.2149 (theoretical value: 446.2166).

[0205] Synthesis Example 3: Preparation of Intermediate d1-567

[0206]

[0207] According to the same preparation method as in Synthesis Example 2, e1-191 was replaced with an equal mole of e1-567 to obtain intermediate d1-567 (16.29 g) with HPLC purity ≧99.73%. Mass spectrum m / z: 446.2178 (theoretical value: 446.2166).

[0208] Synthesis Example 4: Preparation of Compound 5

[0209]

[0210] Preparation of intermediate A-5: Under nitrogen protection, add a-5 (14.75 g, 80.00 mmol), b-5 (14.16 g, 80.00 mmol), K 2 CO 3 (16.58g, 120.00mmol), Pd(PPh 3 ) 4 (0.92 g, 0.80 mmol), 400 mL toluene / ethanol / water (2:1:1), 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 from toluene / ethanol = 10:1 to obtain intermediate A-5 (17.99 g, yield 80%), HPLC purity ≧ 99.78%. Mass spectrum m / z: 279.9938 (theoretical value: 279.9919).

[0211] Preparation of intermediate B-5: Under nitrogen protection, add intermediate A-5 (14.05 g, 50.00 mmol), c-5 (9.90 g, 50.00 mmol), Na 2 CO 3 (7.95g, 75.00mmol), Pd(dppf)Cl 2 (0.37 g, 0.50 mmol), 300 mL toluene / ethanol / water (2:1:1), 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 from toluene / ethanol = 9:1 to obtain intermediate B-5 (15.16 g, yield 76%), HPLC purity ≧ 99.87%. Mass spectrum m / z: 398.0946 (theoretical value: 398.0934).

[0212] Preparation of compound 5: Under nitrogen protection, add B-5 (11.97 g, 30.00 mmol), d-5 (11.11 g, 30.00 mmol), K 2 CO 3 (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), stirred under reflux for 6 hours, after the reaction, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then the obtained solid was recrystallized from toluene to obtain compound 5 (13.29 g, yield 73%), HPLC purity ≧ 99.97%, mass spectrum m / z: 606.2179 (theoretical value: 606.2168). Theoretical element content (%) C 40 H 26 N 6 O: C, 79.19; H, 4.32; N, 13.85. Measured element content (%): C, 79.23; H, 4.30; N, 13.83.

[0213] Synthesis Example 5: Preparation of Compound 15

[0214]

[0215] According to the same preparation method as in Synthesis Example 4, b-5 was replaced with an equal mole of b-15 to obtain compound 15 (16.38 g), HPLC purity ≧99.96%. Mass spectrum m / z: 768.2647 (theoretical value: 768.2638). Theoretical element content (%) C 53 H32 N 6 O: C, 82.79; H, 4.20; N, 10.93. Measured element content (%): C, 82.81; H, 4.16; N, 10.95.

[0216] Synthesis Example 6: Preparation of Compound 26

[0217]

[0218] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-26, c-26, and d-26, respectively, to obtain compound 26 (14.24 g), HPLC purity ≧99.93%. Mass spectrum m / z: 668.2340 (theoretical value: 668.2325). Theoretical element content (%) C 45 H 28 N 6 O: C, 80.82; H, 4.22; N, 12.57. Measured element content (%): C, 80.87; H, 4.20; N, 12.54.

[0219] Synthesis Example 7: Preparation of Compound 31

[0220]

[0221] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-26, c-26, and d-31, respectively, to obtain compound 26 (14.04 g), HPLC purity ≧99.92%. Mass spectrum m / z: 668.2337 (theoretical value: 668.2325). Theoretical element content (%) C 45 H 28 N 6 O: C, 80.82; H, 4.22; N, 12.57. Measured element content (%): C, 80.84; H, 4.20; N, 12.55.

[0222] Synthesis Example 8: Preparation of Compound 33

[0223]

[0224] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-26, c-26, and d-33, respectively, to obtain compound 33 (13.64 g), HPLC purity ≧99.94%. Mass spectrum m / z: 668.2309 (theoretical value: 668.2325). Theoretical element content (%) C 45 H 28 N 6O: C, 80.82; H, 4.22; N, 12.57. Measured element content (%): C, 80.85; H, 4.23; N, 12.51.

[0225] Synthesis Example 9: Preparation of Compound 53

[0226]

[0227] According to the same preparation method as in Synthesis Example 4, b-5 was replaced with an equal mole of b-26 to obtain compound 53 (14.45 g), HPLC purity ≧ 99.92%. Mass spectrum m / z: 668.2333 (theoretical value: 668.2325). Theoretical element content (%) C 45 H 28 N 6 O: C, 80.82; H, 4.22; N, 12.57. Measured element content (%): C, 80.76; H, 4.25; N, 12.61.

[0228] Synthesis Example 10: Preparation of Compound 75

[0229]

[0230] According to the same preparation method as in Synthesis Example 4, b-5 and d-5 were replaced by equimolar b-26 and d-26, respectively, to obtain compound 75 (16.31 g), HPLC purity ≧ 99.95%. Mass spectrum m / z: 744.2649 (theoretical value: 744.2638). Theoretical element content (%) C 51 H 32 N 6 O: C, 82.24; H, 4.33; N, 11.28. Measured element content (%): C, 82.27; H, 4.34; N, 11.23.

[0231] Synthesis Example 11: Preparation of Compound 83

[0232]

[0233] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-26, c-26, and d-83, respectively, to obtain compound 83 (14.62 g), HPLC purity ≧99.90%. Mass spectrum m / z: 676.2840 (theoretical value: 676.2827). Theoretical element content (%) C 45 H 20 D 8 N 6O: C, 79.86; H, 5.36; N, 12.42. Measured element content (%): C, 79.81; H, 5.34; N, 12.46.

[0234] Synthesis Example 12: Preparation of Compound 88

[0235]

[0236] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-26, c-26, and d-88, respectively, to obtain compound 88 (14.63 g), HPLC purity ≧99.97%. Mass spectrum m / z: 696.2650 (theoretical value: 696.2638). Theoretical element content (%) C 47 H 32 N 6 O: C, 81.01; H, 4.63; N, 12.06. Measured element content (%): C, 81.04; H, 4.59; N, 12.08.

[0237] Synthesis Example 13: Preparation of Compound 93

[0238]

[0239] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-26, c-26, and d-93, respectively, to obtain compound 93 (14.88 g), HPLC purity ≧99.93%. Mass spectrum m / z: 718.2473 (theoretical value: 718.2481). Theoretical element content (%) C 49 H 30 N 6 O: C, 81.88; H, 4.21; N, 11.69. Measured element content (%): C, 81.84; H, 4.23; N, 11.72.

[0240] Synthesis Example 14: Preparation of Compound 106

[0241]

[0242] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-26, c-26, and d-106, respectively, to obtain compound 106 (14.95 g), HPLC purity ≧99.91%. Mass spectrum m / z: 682.2130 (theoretical value: 682.2117). Theoretical element content (%) C 45 H 26 N 6 O 2:C, 79.17;H, 3.84;N, 12.31. Measured element content (%): C, 79.14;H, 3.89;N, 12.29.

[0243] Synthesis Example 15: Preparation of Compound 113

[0244]

[0245] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-26, c-26, and d-113, respectively, to obtain compound 113 (15.10 g), HPLC purity ≧99.91%. Mass spectrum m / z: 708.2620 (theoretical value: 708.2638). Theoretical element content (%) C 48 H 32 N 6 O 2 :C, 81.34;H, 4.55;N, 11.86. Measured element content (%): C, 81.32;H, 4.51;N, 11.90.

[0246] Synthesis Example 16: Preparation of Compound 127

[0247]

[0248] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-26, c-127, and d-26, respectively, to obtain compound 127 (15.00 g), HPLC purity ≧99.96%. Mass spectrum m / z: 724.2940 (theoretical value: 724.2951). Theoretical element content (%) C 49 H 36 N 6 O: C, 81.19; H, 5.01; N, 11.59. Measured element content (%): C, 81.22; H, 5.02; N, 11.55.

[0249] Synthesis Example 17: Preparation of Compound 133

[0250]

[0251] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-26, c-133, and d-26, respectively, to obtain compound 133 (15.10 g), HPLC purity ≧99.94%. Mass spectrum m / z: 718.2469 (theoretical value: 718.2481). Theoretical element content (%) C 49 H 30 N 6O: C, 81.88; H, 4.21; N, 11.69. Measured element content (%): C, 81.90; H, 4.18; N, 11.71.

[0252] Synthesis Example 18: Preparation of Compound 147

[0253]

[0254] According to the same preparation method as in Synthesis Example 4, b-5 and c-5 were replaced by equal moles of b-26 and c-147, respectively, to obtain compound 147 (15.17 g), HPLC purity ≧99.97%. Mass spectrum m / z: 692.2338 (theoretical value: 692.2325). Theoretical element content (%) C 47 H 28 N 6 O: C, 81.49; H, 4.07; N, 12.13. Measured element content (%): C, 81.44; H, 4.10; N, 12.15.

[0255] Synthesis Example 19: Preparation of Compound 153

[0256]

[0257] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-26, c-153, and d-26, respectively, to obtain compound 147 (14.13 g), HPLC purity ≧99.93%. Mass spectrum m / z: 719.2442 (theoretical value: 719.2434). Theoretical element content (%) C 48 H 29 N 7 O: C, 80.09; H, 4.06; N, 13.62. Measured element content (%): C, 80.07; H, 4.10; N, 13.59.

[0258] Synthesis Example 20: Preparation of Compound 155

[0259]

[0260] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-26, c-155, and d-26, respectively, to obtain compound 155 (16.16 g) with HPLC purity ≧99.99%. Mass spectrum m / z: 758.2418 (theoretical value: 758.2430). Theoretical element content (%) C 51 H 30 N 6 O 2:C, 80.72;H, 3.99;N, 11.08. Measured element content (%): C, 80.70;H, 3.95;N, 11.14.

[0261] Synthesis Example 21: Preparation of Compound 156

[0262]

[0263] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-26, c-156, and d-26, respectively, to obtain compound 156 (16.95 g), HPLC purity ≧99.91%. Mass spectrum m / z: 784.2965 (theoretical value: 784.2951). Theoretical element content (%) C 54 H 36 N 6 O: C, 82.63; H, 4.62; N, 10.71. Measured element content (%): C, 82.60; H, 4.59; N, 10.76.

[0264] Synthesis Example 22: Preparation of Compound 157

[0265]

[0266] According to the same preparation method as in Synthesis Example 4, b-5 and c-5 were replaced by equal moles of b-157 and c-157, respectively, to obtain compound 157 (14.66 g), HPLC purity ≧99.96%. Mass spectrum m / z: 718.2492 (theoretical value: 718.2481). Theoretical element content (%) C 49 H 30 N 6 O: C, 81.88; H, 4.21; N, 11.69. Measured element content (%): C, 81.90; H, 4.17; N, 11.72.

[0267] Synthesis Example 23: Preparation of Compound 174

[0268]

[0269] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-174, c-26, and d-174, respectively, to obtain compound 174 (15.55 g), HPLC purity ≧99.93%. Mass spectrum m / z: 719.2421 (theoretical value: 719.2434). Theoretical element content (%) C 48 H 29 N 7O: C, 80.09; H, 4.06; N, 13.62. Measured element content (%): C, 80.04; H, 4.10; N, 13.59.

[0270] Synthesis Example 24: Preparation of Compound 191

[0271]

[0272] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-26, c-26, and d1-191, respectively, to obtain compound 191 (14.04 g), HPLC purity ≧99.98%. Mass spectrum m / z: 668.2307 (theoretical value: 668.2325). Theoretical element content (%) C 45 H 28 N 6 O: C, 80.82; H, 4.22; N, 12.57. Measured element content (%): C, 80.87; H, 4.20; N, 12.53.

[0273] Synthesis Example 25: Preparation of Compound 268

[0274]

[0275] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-26, c-268, and e1-567, respectively, to obtain compound 268 (14.97 g), HPLC purity ≧99.92%. Mass spectrum m / z: 744.2631 (theoretical value: 744.2638). Theoretical element content (%) C 51 H 32 N 6 O: C, 82.24; H, 4.33; N, 11.28. Measured element content (%): C, 82.26; H, 4.31; N, 11.26.

[0276] Synthesis Example 26: Preparation of Compound 269

[0277]

[0278] Preparation of intermediate B-269: Under nitrogen protection, add a-5 (9.22 g, 50.00 mmol), b-26 (23.90 g, 100.00 mmol), K 2 CO 3 (27.64g, 200.00mmol), Pd(PPh 3 ) 4(1.16 g, 1.00 mmol), 600 mL toluene / ethanol / water (2:1:1), 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 from toluene / ethanol = 10:1 to obtain intermediate B-269 (18.82 g, yield 75%), HPLC purity ≧ 99.77%. Mass spectrum m / z: 501.0980 (theoretical value: 501.0993).

[0279] Preparation of compound 269: Under nitrogen protection, add B-269 (15.06 g, 30.00 mmol), d-26 (13.39 g, 30.00 mmol), K 2 CO 3 (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), stirred under reflux for 6 hours, after the reaction, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then the obtained solid was recrystallized from toluene to obtain compound 269 (16.97 g, yield 72%), HPLC purity ≧ 99.96%, mass spectrum m / z: 785.2548 (theoretical value: 785.2539). Theoretical element content (%) C 52 H 31 N 7 O 2 :C, 79.48;H, 3.98;N, 12.48. Measured element content (%): C, 79.52;H, 3.96;N, 12.45.

[0280] Synthesis Example 27: Preparation of Compound 301

[0281]

[0282] According to the same preparation method as in Synthesis Example 26, d-26 was replaced by an equal mole of d-5 to obtain compound 301 (15.12 g), HPLC purity ≧99.97%. Mass spectrum m / z: 709.2237 (theoretical value: 709.2226). Theoretical element content (%) C 46 H 27 N 7 O 2 :C, 77.84;H, 3.83;N, 13.81. Measured element content (%): C, 77.87;H, 3.85;N, 13.78.

[0283] Synthesis Example 28: Preparation of Compound 340

[0284]

[0285] According to the same preparation method as in Synthesis Example 26, b-26 was replaced with an equal mole of b-340 to obtain compound 340 (15.44 g), HPLC purity ≧ 99.96%. Mass spectrum m / z: 745.3180 (theoretical value: 745.3165). Theoretical element content (%) C 48 H 39 N 7 O 2 :C, 77.29;H, 5.27;N, 13.15. Measured element content (%): C, 77.26;H, 5.25;N, 13.19.

[0286] Synthesis Example 29: Preparation of Compound 399

[0287]

[0288] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-399, c-26, and d-399, respectively, to obtain compound 399 (15.00 g), HPLC purity ≧99.91%. Mass spectrum m / z: 684.2085 (theoretical value: 684.2096). Theoretical element content (%) C 45 H 28 N 6 S: C, 78.93; H, 4.12; N, 12.27. Measured element content (%): C, 78.95; H, 4.16; N, 12.22.

[0289] Synthesis Example 30: Preparation of Compound 427

[0290]

[0291] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-427, c-427, and d-26, respectively, to obtain compound 427 (16.44 g), HPLC purity ≧99.94%. Mass spectrum m / z: 760.2427 (theoretical value: 760.2409). Theoretical element content (%) C 51 H 32 N 6 S: C, 80.50; H, 4.24; N, 11.04. Measured element content (%): C, 80.46; H, 4.27; N, 11.01.

[0292] Synthesis Example 31: Preparation of Compound 433

[0293]

[0294] According to the same preparation method as in Synthesis Example 4, b-5 and d-5 were replaced by equimolar b-427 and d-433, respectively, to obtain compound 433 (14.77 g), HPLC purity ≧ 99.93%. Mass spectrum m / z: 734.2263 (theoretical value: 734.2253). Theoretical element content (%) C 49 H 30 N 6 S: C, 80.09; H, 4.11; N, 11.44. Measured element content (%): C, 80.12; H, 4.07; N, 11.47.

[0295] Synthesis Example 32: Preparation of Compound 443

[0296]

[0297] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-427, c-443, and d-26, respectively, to obtain compound 443 (16.17 g) with HPLC purity ≧99.95%. Mass spectrum m / z: 769.2959 (theoretical value: 769.2974). Theoretical element content (%) C 51 H 23 D 9 N 6 S: C, 79.56; H, 5.37; N, 10.91. Measured element content (%): C, 79.51; H, 5.40; N, 10.93.

[0298] Synthesis Example 33: Preparation of Compound 445

[0299]

[0300] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-427, c-445, and d-445, respectively, to obtain compound 445 (15.69 g), HPLC purity ≧99.93%. Mass spectrum m / z: 757.2453 (theoretical value: 757.2444). Theoretical element content (%) C 47 H 35 N 7 SSi: C, 74.48; H, 4.65; N, 12.94. Measured element content (%): C, 74.46; H, 4.68; N, 12.92.

[0301] Synthesis Example 34: Preparation of Compound 454

[0302]

[0303] According to the same preparation method as in Synthesis Example 4, b-5, c-5, and d-5 were replaced by equal moles of b-427, c-454, and d-454, respectively, to obtain compound 454 (14.61 g), HPLC purity ≧99.98%. Mass spectrum m / z: 685.2059 (theoretical value: 685.2049). Theoretical element content (%) C 44 H 27 N 7 S: C, 77.06; H, 3.97; N, 14.30. Measured element content (%): C, 77.09; H, 3.93; N, 14.28.

[0304] Synthesis Example 35: Preparation of Compound 567

[0305]

[0306] According to the same preparation method as in Synthesis Example 26, b-26 and d-26 were replaced by equimolar b-567 and d1-567, respectively, to obtain compound 567 (16.85 g), HPLC purity ≧99.92%. Mass spectrum m / z: 825.2577 (theoretical value: 825.2584). Theoretical element content (%) C 52 H 23 D 8 N 7 S 2 :C, 75.61;H, 4.76;N, 11.87. Measured element content (%): C, 75.65;H, 4.74;N, 11.85.

[0307] Synthesis Example 36: Preparation of Compound 683

[0308]

[0309] According to the same preparation method as in Synthesis Example 26, a-5 and d-26 were replaced by equal moles of a-683 and d-683, respectively, to obtain compound 683 (16.29 g), HPLC purity ≧99.93%. Mass spectrum m / z: 785.2520 (theoretical value: 785.2539). Theoretical element content (%) C 52 H 31 N 7 O 2 :C, 79.48;H, 3.98;N, 12.48. Measured element content (%): C, 79.51;H, 3.93;N, 12.50.

[0310] Synthesis Example 37: Preparation of Compound 716

[0311]

[0312] According to the same preparation method as in Synthesis Example 26, a-5, b-26, and d-26 were replaced by equal moles of a-716, b-716, and d-716, respectively, to obtain compound 716 (15.81 g), HPLC purity ≧99.96%. Mass spectrum m / z: 731.2335 (theoretical value: 731.2321). Theoretical element content (%) C 50 H 29 N 5 O 2 :C, 82.06;H, 3.99;N, 9.57. Measured element content (%): C, 82.10;H, 3.94;N, 9.60.

[0313] Device Embodiment

[0314] 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%.

[0315] 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.

[0316] Example 1: Preparation of organic electroluminescent device 1

[0317] 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-1 was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 115 nm; RH-1:compound of the present invention 5:RD-1=49:49:2 (wt%) was vacuum-deposited on the hole transport layer to form a light-emitting layer with a thickness of 30 nm; ET-1 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.

[0318] Examples 2 to 34: Preparation of organic electroluminescent devices 2 to 34

[0319] The compound 5 in the light-emitting layer of Example 1 is replaced by compound 15, compound 26, compound 31, compound 33, compound 53, compound 75, compound 83, compound 88, compound 93, compound 106, compound 113, compound 127, compound 133, compound 147, compound 153, compound 155, compound 156, compound 157, compound 174, compound 191, compound 268, compound 269, compound 301, compound 340, compound 399, compound 427, compound 433, compound 443, compound 445, compound 454, compound 567, compound 683, and compound 716, respectively, and the other steps are the same to obtain organic electroluminescent devices 2 to 34.

[0320] Comparative Examples 1-2: Preparation of Comparative Organic Electroluminescent Devices 1-2

[0321] The compound 5 in the light-emitting layer of Example 1 was replaced by R-1 and R-2 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 1-2.

[0322]

[0323] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 1 to 34 of the present invention and Comparative Examples 1 to 2 are shown in Table 1.

[0324] Table 1 Test data of luminescence characteristics of organic electroluminescent devices

[0325]

[0326]

[0327] 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%;

[0328] It can be seen from Table 1 that when the heterocyclic compound of Formula 1 of the present invention is used as the main material of the light-emitting layer in the organic electroluminescent device, compared with the comparative organic electroluminescent devices 1 to 2, it has a lower driving voltage, a higher luminous efficiency and a longer service life, and the performance of the organic electroluminescent device is more excellent.

[0329] Example 35: Preparation of organic electroluminescent device 35

[0330] 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-2 was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 115 nm; GH-1:GH-2:GD-1=46:46:8 (wt%) was vacuum-deposited on the hole transport layer to form a light-emitting layer with a thickness of 28 nm; the compound of the present invention 5: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.

[0331] Examples 36 to 68: Preparation of organic electroluminescent devices 36 to 68

[0332] The compound 5 in the electron transport layer of Example 35 is replaced by compound 15, compound 26, compound 31, compound 33, compound 53, compound 75, compound 83, compound 88, compound 93, compound 106, compound 113, compound 127, compound 133, compound 147, compound 153, compound 155, compound 156, compound 157, compound 174, compound 191, compound 268, compound 269, compound 301, compound 340, compound 399, compound 427, compound 433, compound 443, compound 445, compound 454, compound 567, compound 683, and compound 716, respectively, and the other steps are the same to obtain organic electroluminescent devices 36 to 68.

[0333] Comparative Examples 3-4: Preparation of Comparative Organic Electroluminescent Devices 3-4

[0334] The compound 5 in the electron transport layer of Example 35 was replaced by R-3 and R-4, and the other steps were the same to obtain comparative organic electroluminescent devices 3 to 4.

[0335]

[0336]

[0337] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 35 to 68 of the present invention and Comparative Examples 3 to 4 are shown in Table 2.

[0338] Table 2 Test data of luminescence characteristics of organic electroluminescent devices

[0339]

[0340]

[0341] 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%;

[0342] It can be seen from Table 2 that, compared with the comparative organic electroluminescent devices 3 to 4, the device performance of the organic electroluminescent device containing the heterocyclic compound of Formula 1 of the present invention in the electron transport layer is better, specifically manifested in lower driving voltage, higher luminous efficiency and longer service life. The heterocyclic compound of Formula 1 of the present invention is a good electron transport material.

[0343] Example 69: Preparation of organic electroluminescent device 69

[0344] HI-1:HI-2=5:95 (wt%) was vacuum-deposited on the ITO anode as a hole injection layer with a thickness of 15 nm; HT-3 was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 110 nm; BH-1:BD-1=95:5 (wt%) was vacuum-deposited on the hole transport layer to form a light-emitting layer with a thickness of 25 nm; the compound 5 of the present invention was vacuum-deposited on the light-emitting layer as a hole blocking layer with a thickness of 20 nm; ET-2 was vacuum-deposited on the hole blocking 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.

[0345] Examples 70-93: Preparation of organic electroluminescent devices 70-93

[0346] The compound 5 in the hole blocking layer of Example 69 is replaced by compound 26, compound 31, compound 33, compound 53, compound 75, compound 83, compound 88, compound 93, compound 106, compound 113, compound 127, compound 133, compound 147, compound 155, compound 156, compound 191, compound 268, compound 269, compound 301, compound 399, compound 427, compound 433, compound 443, and compound 454, respectively, and the other steps are the same to obtain organic electroluminescent devices 70 to 93.

[0347] Comparative Example 5: Preparation of Comparative Organic Electroluminescent Device 5

[0348] The compound 5 in the hole blocking layer of Example 69 was replaced by R-5, and the other steps were the same to obtain a comparative organic electroluminescent device 5.

[0349]

[0350]

[0351] The test results of the luminescence characteristics of the organic electroluminescent devices prepared in Examples 69 to 93 of the present invention and Comparative Example 5 are shown in Table 3.

[0352] Table 3 Test data of luminescence characteristics of organic electroluminescent devices

[0353]

[0354] 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%;

[0355] It can be seen from Table 3 that, compared with the comparative organic electroluminescent device 5, the organic electroluminescent device containing the heterocyclic compound of Formula 1 of the present invention in the hole blocking layer exhibits higher luminous efficiency and longer service life.

[0356] Example 94: Preparation of organic electroluminescent device 94

[0357] 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; RH-2:RD-1=97:3 (wt%) was vacuum evaporated on the hole transport layer to form a light-emitting layer with a thickness of 30 nm; ET-3: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; the compound 26 of the present invention was vacuum evaporated on the cathode as a covering layer with a thickness of 70 nm.

[0358] Examples 95-109: Preparation of organic electroluminescent devices 95-109

[0359] The compound 26 in the covering layer of Example 94 is replaced by compound 53, compound 75, compound 83, compound 127, compound 133, compound 147, compound 155, compound 269, compound 301, compound 340, compound 433, compound 443, compound 567, compound 683, and compound 716, respectively, and the other steps are the same to obtain organic electroluminescent devices 95 to 109.

[0360] Comparative Example 6: Preparation of Comparative Organic Electroluminescent Device 6

[0361] The compound 26 in the covering layer of Example 94 was replaced by R-6, and the other steps were the same to obtain a comparative organic electroluminescent device 6.

[0362]

[0363] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 94 to 109 of the present invention and Comparative Example 6 are shown in Table 4.

[0364] Table 4 Test data of luminescence characteristics of organic electroluminescent devices

[0365]

[0366]

[0367] 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%;

[0368] It can be seen from Table 4 that the organic electroluminescent device using the heterocyclic compound of Formula 1 as the covering material has higher luminous efficiency and longer service life than the comparative organic electroluminescent device 6. In summary, the heterocyclic compound of Formula 1 of the present invention is a covering material with excellent performance.

[0369] 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 are the same or different and are selected from CR0 or N, and at least one x is selected from N, and the x bonded to L1, L2, and L3 is selected from C atoms; The R0 is selected from one of 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 of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring; Ar1 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 Ar1 is the connection site with L1; The ring A is selected from a substituted or unsubstituted C2-C30 nitrogen-containing heterocycle; The ring B is selected from a substituted or unsubstituted C6-C30 aromatic ring; Said Y is selected from O or S; The z are the same or different and are selected from CH or N; The R3 are the same or different and are selected from hydrogen, deuterium, cyano, 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; The Ar3 is selected from one of the following groups: The u are the same or different and are selected from CR5 or N; The Q is selected from O, S, CR6R7 or NR8; the Q1 is selected from O, S or NR9; the Q2 is selected from 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 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 L1, L2, and L3 are the same or different and are 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 ring A is selected from one of the groups shown in c-12 to c-22, and the ring B is selected from one of the groups shown in c-1 to c-11. The v's are the same or different and are selected from CR2 or N, and at least one v is selected from N; The R1s 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, 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; The R2s 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, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused ring of substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring; The n1 is selected from 0, 1, 2, 3 or 4; the n2 is selected from 0, 1, 2, 3, 4, 5 or 6; the n3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

3. The heterocyclic compound according to claim 1, characterized in that Said One selected from the following groups, The R1s are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, or a substituted or unsubstituted group selected from the group consisting of 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, triisopropyl methylsilyl, 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; The R2 may be the same or different and may be selected from hydrogen, deuterium, cyano, halogen, nitro, or a substituted or unsubstituted group selected from the group consisting of 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, triisopropyl methylsilyl, 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; The n1 is selected from 0, 1, 2, 3 or 4; the n2 is selected from 0, 1, 2, 3, 4, 5 or 6; the n3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the n4 is selected from 0, 1, 2 or 3; the n5 is selected from 0, 1, 2, 3, 4 or 5; the n6 is selected from 0, 1 or 2.

4. The heterocyclic compound according to claim 1, characterized in that The Ar1 is selected from one of the following groups: The e is the same or different from CR c or N; The W is selected from O, S, CR a R b or NR d ; W1 is selected from O, S or NR f ; W2 is selected from CR g 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 a , R b 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 a , R b Bonding to form a substituted or unsubstituted ring; The R g 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 d , R f 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.

5. The heterocyclic compound according to claim 1, characterized in that Said One selected from the following groups, Said Y is selected from O or S; The R3 is the same or different and is selected from hydrogen, deuterium, cyano, 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-butylsilane R3 is substituted or unsubstituted; R3 is substituted or unsubstituted; R3 is substituted or unsubstituted; R3 is substituted or unsubstituted; R3 is substituted or unsubstituted; R3 is substituted or unsubstituted; 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 Ar3 is selected from one of the following groups: 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 ring; The R6 and R7 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, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropyl Propylsilyl, 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; The R8 and R9 are the same or different and are selected from one of the following groups which are substituted or unsubstituted: 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; The c1 is selected from 0, 1, 2, 3, 4 or 5; the c2 is selected from 0, 1, 2, 3 or 4; the c3 is selected from 0, 1, 2 or 3; the c4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c5 is selected from 0, 1, 2, 3, 4, 5 or 6; the c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the c7 is selected from 0, 1 or 2; the c8 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

7. The heterocyclic compound according to claim 1, characterized in that The L1, L2, and L3 are the same or different and are selected from a single bond or one of the following groups: 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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