A heterocycle-containing arylamine compound and an organic light-emitting device thereof

Abstract

The application provides a heterocyclic-containing arylamine compound and an organic light-emitting device thereof, and relates to the technical field of organic photoelectric materials.The compound contains a dibenzofuran / dibenzothiophene group, the group has stronger electron-donating capacity, and the steric hindrance of the 1, 4 position is smaller compared with the 1, 3 position or the 2, 4 position of the dibenzofuran / dibenzothiophene group, which is beneficial to the film formation of the molecule, in particular, the heterocyclic-containing arylamine compound of the application has good stability and film formation after the amine group is substituted by deuterium, and is applied to a hole transport layer, a light-emitting auxiliary layer, a cover layer or a host material layer, the photoelectric performance of the device is greatly improved, and the device has the advantages of high light-emitting efficiency and long service life.The application has good industrialization prospect, and can be widely applied to the fields of panel display, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photosensitive bodies, indicator boards, signal lamps and the like.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic optoelectronic materials, and in particular to a heterocycle-containing arylamine compound and an organic light-emitting device thereof. BACKGROUND

[0002] At present, organic light-emitting devices develop rapidly, and organic optoelectronic materials therein have become a research hotspot in the field. An organic light-emitting device converts electrical energy into light by applying electrical power to an organic electroluminescent material, and generally includes an anode, a cathode, and an organic layer formed between or outside the two electrodes. The organic layer can include a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cover layer, and the like. In the organic light-emitting device, holes from the anode and electrons from the cathode are injected into the light-emitting layer by applying a voltage, and excitons with high energy are generated by recombination of the holes and the electrons. The organic light-emitting compound emits light by energy when the energy is transferred to the excited state and returns to the ground state from the excited state.

[0003] The organic layer plays different roles in the device. By using a multi-layer structure, the energy level matching in each layer of the device is good, and the injection efficiency of carriers between the interfaces of each layer is improved. At the same time, the energy level matching also reduces the Joule heat generated during the operation of the device, thereby improving the service life of the device. As a hole transport layer of an organic light-emitting device, its basic role is to improve the transmission rate of holes in the device, and effectively block electrons in the light-emitting layer to achieve maximum recombination of carriers and improve light-emitting efficiency; at the same time, the energy barrier in the injection process of holes is reduced, and the injection efficiency of holes is improved, thereby improving the light-emitting efficiency of the device and prolonging the service life of the device. In a conventional device, due to the total reflection effect of the substrate material and the transverse waveguide effect in the organic material, the number of photons that can smoothly exit from the electrode is extremely limited. Therefore, by increasing the light extraction organic layer, i.e., the cover layer, the light extraction efficiency of the device is improved, the external quantum efficiency is increased, and the performance of the device is ultimately improved. The host material generally needs to have a higher LUMO value than the guest material and a lower HOMO value than the guest material.

[0004] At present, the double type cyclic compounds containing heteroatoms have very large differences in properties according to material structures, and thus are applied to various organic layers. Specifically, according to the number and fused position of rings and the type and arrangement of heteroatoms, the band gap (HOMO, LUMO), electrical properties, chemical properties and physical properties are different, and thus the application development of the organic layers in various devices using the compounds has been developed, and the performance of the organic materials applied to OLED devices is still not perfect, the imbalance of carrier injection in the device and the low light extraction efficiency have been the main problems troubling the industry, so by adjusting the structure of the material, the carrier injection balance can be promoted, the film-forming property and the thermal stability of the thin film of the material are improved, and the appropriate HOMO value makes the overall luminous efficiency and service life of the device improved, which is an urgent problem to be solved. SUMMARY

[0005] The present application aims to provide a heterocyclic-containing arylamine compound and an organic light-emitting device thereof on the basis of the prior art, for the purpose of industrialization, and the organic light-emitting device prepared by using the heterocyclic-containing arylamine compound is applied to the development of an organic light-emitting device with high efficiency and long service life in a hole transport layer / light-emitting auxiliary layer / host material / cover layer, and the molecular structure general formula is shown as formula I:

[0006]

[0007] The X0 is selected from O or S;

[0008] The Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 are the same as or different from each other, and are independently selected from one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C25 heteroaryl group, and a fused ring group of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring;

[0009] The R a , R b are the same as or different from each other, and are independently selected from one of hydrogen, a halogen, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, and a substituted or unsubstituted C6-C25 aryl group, or any two adjacent R a groups are bonded to form a substituted or unsubstituted benzene ring, or any two adjacent R b groups are bonded to form a substituted or unsubstituted benzene ring;

[0010] The a is selected from 0, 1 or 2; and the b is selected from 0, 1, 2 or 3;

[0011] The L1, L2, L3, L4, L5, L6, L a , L b, L c independently selected from one of a single bond, a substituted or unsubstituted C6-C25 arylene group, a substituted or unsubstituted C2-C25 heteroarylene group, a substituted or unsubstituted C3-C10 alicyclylene group, and a C6-C25 arycyclylene group;

[0012] at least one of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, and L6 contains a deuterium or a deuterated group.

[0013] The present application also provides an organic light-emitting device, comprising an anode, a cathode, and an organic layer between the anode and the cathode or outside one or more of the anode and the cathode, wherein the organic layer contains any one or a combination of at least two of the heterocyclic aromatic amine compounds of the present application.

[0014] The present application has the following advantages:

[0015] The present application provides a heterocyclic aromatic amine compound and an organic light-emitting device thereof. The compound of the present application contains a dibenzofuran / dibenzothiophene group. Such a group has stronger electron-donating ability and smaller steric hindrance at the 1,4 position than at the 1,3 position or the 2,4 position of the dibenzofuran / dibenzothiophene group, which is conducive to the film formation of the molecule, thereby making the compound have better hole transport capacity, improving the hole transport efficiency, and improving the light-emitting efficiency of the organic light-emitting device. In addition, the present application introduces deuterium atoms into the amine group, so that the compound has better thermal stability, can reduce the accumulation of holes in the hole transport layer or the light-emitting auxiliary layer, and improve the service life of the device. The compound of the present application is applied to the cover layer, which can reduce the total reflection loss and waveguide loss in the OLED device, effectively improving the light-emitting efficiency and service life of the device. The compound of the present application is applied to the host material layer, which has suitable HOMO and LUMO energy levels, and can improve the light-emitting efficiency and service life of the organic light-emitting device.

[0016] The heterocyclic aromatic amine compound represented by Formula I of the present application has good stability and film-forming property after the amine group is substituted by deuterium. Compared with the non-deuterated compound, the photoelectric performance of the device is greatly improved, and the light-emitting efficiency is increased and the service life is prolonged. DETAILED DESCRIPTION

[0017] The technical solutions of the embodiments of the present application will be described below. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments of the present application, all other embodiments obtained by those skilled in the art without creative labor fall within the protection scope of the present application.

[0018] In the compounds of the present application, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes atoms in both their natural isotopic abundance and non-natural abundance.

[0019] In the present application, the use of "H" and "hydrogen" means that the hydrogen atom in the chemical structure contains no more than a deuterium atom or a tritium atom of natural abundance, for example, no more than 0.0156 atom% of deuterium. "D" and "deuterium" mean that the deuterium content is above natural abundance, for example, any value of more than 0.1 atom%, more than 1 atom%, more than 10 atom%, for example, in which about 95 atom% is deuterium. In the present application, the omission of a hydrogen atom not drawn indicates "H" or "hydrogen".

[0020] In the present specification, when the position of a substituent on a ring is not fixed, it means that it can be attached to any one of the corresponding alternative sites of the ring. For example, may mean and so on.

[0021] The halogen in the present application means fluorine, chlorine, bromine, and iodine.

[0022] The alkyl group in the present application means a hydrocarbon group in which one hydrogen atom is removed from an alkane molecule, which can be a straight-chain alkyl group, a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes a methyl group, an ethyl group, a n-propyl group, a n-butyl group, a n-pentyl group, a n-hexyl group, a n-heptyl group, a n-octyl group, a n-nonyl group, a n-decyl group, a undecyl group, a dodecyl group, and the like, but is not limited thereto; the branched-chain alkyl group includes an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, isomeric groups of a n-pentyl group, isomeric groups of a n-hexyl group, isomeric groups of a n-heptyl group, isomeric groups of a n-octyl group, isomeric groups of a n-nonyl group, isomeric groups of a n-decyl group, and the like, but is not limited thereto. The above alkyl group is preferably a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group.

[0023] The chain alkyl group having more than three carbon atoms in the present application includes isomers thereof, for example, a propyl group includes a n-propyl group, an isopropyl group, a butyl group includes a n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group. And so on.

[0024] The cycloalkyl group in the present application means a hydrocarbon group in which one hydrogen atom is removed from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 3 to 6 carbon atoms, examples of which can include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, and the like, but is not limited thereto. The above cycloalkyl group is preferably a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a norbornyl group.

[0025] The heterocycloalkyl group according to the present application means a monovalent group in which at least one of the core carbon atoms of a cycloalkyl group is substituted with a heteroatom. The heteroatom includes, but is not limited to, atoms such as N, O, S, Si, B, P, and the like. It preferably has 3 to 30 carbon atoms, more preferably 3 to 15 carbon atoms, and still more preferably 3 to 10 carbon atoms. Examples of the heterocycloalkyl group include, but are not limited to, groups such as aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, azepanyl, homopiperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, and the like.

[0026] The aryl group according to the present application means a monovalent group obtained by removing one hydrogen atom from the aromatic core carbon of an aromatic compound molecule, and it can be a monocyclic aryl group, a polycyclic aryl group, or a fused ring aryl group. It preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group means an aryl group having only one aromatic ring in the molecule, and examples thereof include, but are not limited to, phenyl and the like. The polycyclic aryl group means an aryl group having two or more independent aromatic rings in the molecule, and examples thereof include, but are not limited to, biphenyl, terphenyl, and the like. The fused ring aryl group means an aryl group having two or more aromatic rings in the molecule which are fused to each other by sharing two adjacent carbon atoms, and examples thereof include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthenyl, spirobifluorenyl, and the like. The aryl group is preferably phenyl, biphenyl, terphenyl, naphthyl (preferably 2-naphthyl), anthryl (preferably 2-anthryl), phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylenyl, or spirobifluorenyl.

[0027] The heteroaryl group according to the present application refers to the general term of the group obtained by replacing one or more aromatic ring carbon atoms in the aryl group with a heteroatom, including but not limited to oxygen, sulfur, nitrogen or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, most preferably 3 to 12 carbon atoms, the connecting site of the heteroaryl group can be located on the ring carbon atom or the ring nitrogen atom, the heteroaryl group can be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a fused ring heteroaryl group. The monocyclic heteroaryl group includes pyridyl, pyrimidyl, triazinyl, furanyl, thienyl, pyrrolyl, imidazolyl, etc., but is not limited thereto; the polycyclic heteroaryl group includes bipyridyl, bipyrimidyl, phenylpyridyl, etc., but is not limited thereto; the fused ring heteroaryl group includes quinolinyl, isoquinolinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzo-dibenzofuranyl, dibenzothienyl, benzo-dibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxazinyl, etc., but is not limited thereto. The above-mentioned heteroaryl group is preferably pyridyl, pyrimidyl, thienyl, furanyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, benzo-dibenzothienyl, benzo-dibenzofuranyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenoxazinyl.

[0028] The alkenyl group according to the present application refers to a monovalent group obtained by removing one hydrogen atom from an alkene molecule, including monoalkenyl, dialkenyl, polyalkenyl, etc. Preferably having 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, particularly preferably 2 to 15 carbon atoms, most preferably 2 to 6 carbon atoms. Examples of the alkenyl group include ethenyl, ethenyl, propenyl, 1-butenyl, 2-butenyl, 1-pentenyl, 2-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, etc., but are not limited thereto. The above-mentioned alkenyl group is preferably ethenyl.

[0029] The alkenyl group according to the present application having more than three carbon atoms includes its isomers, for example, propenyl includes 1-propenyl or 2-propenyl, butenyl includes 1-butenyl, 2-butenyl, or 3-butenyl, pentenyl includes 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, hexenyl includes 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl. And so on.

[0030] The arylene group according to the present application refers to a general term of divalent group after removing two hydrogen atoms from the aromatic ring carbon of aromatic compound molecule, which can be monocyclic arylene group, polycyclic arylene group or fused ring arylene group, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, most preferably 6 to 12 carbon atoms. The monocyclic arylene group includes phenylene and the like, but is not limited thereto; the polycyclic arylene group includes biphenylene, terphenylene and the like, but is not limited thereto; the fused ring arylene group includes naphthylene, anthrylene, phenanthrylene, fluorenylene, pyrenylene, triphenylylene, fluoranthrylene, phenylfluorenylene and the like, but is not limited thereto. The above arylene group is preferably phenylene, biphenylene, terphenylene, naphthylene, fluorenylene, phenylfluorenylene.

[0031] The heteroarylene group according to the present application refers to a general term of group obtained by replacing one or more aromatic ring carbons in arylene group with heteroatom, which includes but is not limited to oxygen, sulfur, nitrogen or phosphorus atom. Preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, most preferably 3 to 12 carbon atoms, the linking site of the heteroarylene group can be on the ring-forming carbon atom or on the ring-forming nitrogen atom, and the heteroarylene group can be monocyclic heteroarylene group, polycyclic heteroarylene group or fused ring heteroarylene group. The monocyclic heteroarylene group includes pyridylene, pyrimidylene, triazylene, furanylene, thienylene and the like, but is not limited thereto; the polycyclic heteroarylene group includes bipyridylene, bipyrimidylene, phenylpyridylene and the like, but is not limited thereto; the fused ring heteroarylene group includes quinolylene, isoquinolylene, indolylene, benzothienylene, benzofuranylene, benzoxazolylene, benzimidazolylene, benzothiazolylene, dibenzofuranylene, benzodibenzofuranylene, dibenzothienylene, benzodibenzothienylene, carbazolylene, benzocarbazolylene, azulenylene, 9,10-dihydroazulenylene, phenoxazinylene, phenothiazinylene, phenoxathiazinylene and the like, but is not limited thereto. The above heteroaryl group is preferably pyridylene, pyrimidylene, thienylene, furanylene, benzothienylene, benzofuranylene, benzoxazolylene, benzimidazolylene, benzothiazolylene, dibenzofuranylene, dibenzothienylene, benzodibenzothienylene, benzodibenzofuranylene, carbazolylene, azulenylene, phenoxazinylene, phenothiazinylene, phenoxathiazinylene.

[0032] The sub-fused ring of the aliphatic ring and the aromatic ring according to the present application refers to a divalent group after the aliphatic ring and the aromatic ring are fused together and two hydrogen atoms are removed. Preferably, it has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 12 carbon atoms. Examples can include, but are not limited to, sub-benzocyclopropyl, sub-benzocyclobutyl, sub-benzocyclopentyl, sub-benzocyclohexyl, sub-benzocycloheptyl, sub-benzocyclopentenyl, sub-benzocyclohexenyl, sub-benzocycloheptenyl, sub-naphthocyclopropyl, sub-naphthocyclobutyl, sub-naphthocyclopentyl, sub-naphthocyclohexyl, and the like.

[0033] The fused ring of the aromatic ring and the aliphatic ring according to the present application refers to a ring in which one or more aromatic rings and one or more aliphatic rings are fused to each other by sharing two adjacent carbon atoms. Preferably, the aromatic ring has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Preferably, the aliphatic ring has 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. Examples include, but are not limited to, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutene, benzocyclopentene, benzocyclohexene, benzocycloheptene, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentene, naphthocyclohexene, and the like.

[0034] The aliphatic ring according to the present application refers to a cyclic hydrocarbon having aliphatic properties. Preferably, it has 3 to 60 carbon atoms, more preferably 3 to 30 carbon atoms, further preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. It can form a single ring or multiple rings, and can be completely unsaturated or partially unsaturated. Specific examples include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, and the like. Multiple single rings can be connected in various ways: two rings in the molecule can share a carbon atom to form a spiro ring; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; and several rings can be connected to each other to form a cage structure.

[0035] “Unsubstituted” according to the present application, such as unsubstituted alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, unsubstituted alkenyl, unsubstituted arylene, unsubstituted heteroarylene, and the like, refers to the “hydrogen” (H) in the group being replaced by no other group, including deuterium.

[0036] The "substituted..." such as substituted alkyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted aryl, substituted heteroaryl, substituted alkenyl, substituted arylene, substituted heteroarylene, etc. according to the present application means mono- or poly-substituted with a group selected from, but not limited to, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C15 heteroaryl, substituted or unsubstituted amine, etc., preferably mono- or poly-substituted with a group selected from deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, camphorinyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, perylenyl, pyrenyl, benzyl, tolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, diphenylamine, dimethylamine, carbazolyl, 9-phenylcarbazolyl, acridinyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, phenothiazinyl, phenoxazinyl, indolyl. In addition, the above substituents can be further substituted with one or more deuterium, halogen, cyano, alkyl, cycloalkyl, aryl.

[0037] According to the present application, R4, R5 combine with each other to form a substituted or unsubstituted spiro ring structure, and R x , R y combine with each other to form a substituted or unsubstituted spiro ring structure, wherein the "spiro ring structure" means a structure in which two carbon rings share one carbon atom, and the substituted or unsubstituted spiro ring structure can be of the following spiro ring types:

[0038]

[0039] wherein r is a substituent, r is selected from one of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkenyl, or two adjacent r substituents can combine with each other to form a substituted or unsubstituted cyclic structure; r1 is selected from 0, 1 or 2; r2 is selected from 0, 1, 2, 3 or 4; r3 is selected from 0, 1, 2, 3, 4, 5 or 6; r4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; r5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; r6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; r7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; and Ar is selected from one of deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl.

[0040] The two adjacent substituents described in the present application can combine with each other to form a substituted or unsubstituted three- to eight-membered aliphatic ring, which can be a substituted or unsubstituted aliphatic ring as follows:

[0041]

[0042] wherein "*" represents a ring-forming connection site; and the dotted line represents a single bond or a double bond.

[0043] The ring-forming connection described in the present application means that two groups are connected to each other by a chemical bond and optionally undergo aromatization. Examples are as follows:

[0044]

[0045] In the present application, the ring formed by the connection can be a five-membered ring or a six-membered ring or a fused ring, such as benzene, naphthalene, fluorene, cyclopentene, cyclohexene, cyclopentane, cyclohexane, cyclohexane benzene, quinoline, isoquinoline, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.

[0046] The present application provides a heterocycle-containing arylamine compound, the molecular structure of which is shown in formula I:

[0047]

[0048] X0 is selected from O or S;

[0049] The Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are the same as or different from each other, and are independently selected from one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C25 heteroaryl groups, substituted or unsubstituted C6-C30 aromatic rings, and C3-C30 aliphatic ring fused ring groups.

[0050] The R a R b They may be the same as or different from each other, and are independently selected from one of hydrogen, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C25 aryl, or any two adjacent Rs. a Groups bond together to form substituted or unsubstituted benzene rings, or any two adjacent R groups b Groups bond together to form substituted or unsubstituted benzene rings;

[0051] a is selected from 0, 1, or 2; b is selected from 0, 1, 2, or 3;

[0052] The L1, L2, L3, L4, L5, L6, L a L b L c It is independently selected from one of the following: single bond, substituted or unsubstituted C6-C25 arylene, substituted or unsubstituted C2-C25 heteroarylene, substituted or unsubstituted C3-C10 aliphatic ring and C6-C25 aromatic ring fused and cycloalgyl groups;

[0053] At least one of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, and L6 contains deuterium or a deuterated group.

[0054] Preferably, "at least one" includes one, two, three, four, five, six, seven, eight, nine, ten, eleven, or twelve.

[0055] Preferably, at least two of the Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, and L6 contain deuterium or deuterated groups.

[0056] Preferably, any two or more of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, and L6 contain one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, or more deuterium.

[0057] Preferably, at least two of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 contain deuterium or a deuterated group.

[0058] Preferably, two, three, four, five, or six of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 contain deuterium or a deuterated group.

[0059] Preferably, at least two of L1, L2, L3, L4, L5, and L6 contain deuterium or a deuterated group.

[0060] Preferably, two, three, four, five, or six of L1, L2, L3, L4, L5, and L6 contain deuterium or a deuterated group.

[0061] Preferably, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are the same or different from each other and are independently selected from one of the following groups:

[0062]

[0063] wherein in formula a, R1is selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C25 heteroaryl, and a fused ring group of substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring;

[0064] n1is selected from 0, 1, 2, 3, 4, or 5; when n1is greater than 1, each R1is the same or different, and adjacent two R1groups can be bonded to form a substituted or unsubstituted cyclic structure;

[0065] In formula b, X is selected from any one of O, S, C(R4)(R5), and N(R);

[0066] R4and R5are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, a fused ring group of substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl, or R4and R5may be combined to form a substituted or unsubstituted spiro ring; or any one of R4and R5may be directly bonded to L1, L2, L3, L4, L5, or L6;

[0067] R is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl, or R can be directly bonded to L1, L2, L3, L4, L5 or L6;

[0068] R2, R3are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted fused ring group of C6-C30 aromatic ring and C3-C30 aliphatic ring;

[0069] n2 is selected from 0, 1, 2, 3 or 4; when n2 is greater than 1, each R2 is the same or different, and adjacent two R2 groups can be bonded to form a substituted or unsubstituted cyclic structure; n3 is selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, each R3 is the same or different, and adjacent two R3 groups can be bonded to form a substituted or unsubstituted cyclic structure.

[0070] Further preferably, Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 are the same or different from each other, and are independently selected from one of the following groups,

[0071]

[0072] R1is selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl; or adjacent two R1s are combined to form a substituted or unsubstituted aliphatic ring of three to eight members;

[0073] R2, R3are independently selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, iso-propyl, t-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, anthracenyl, phenanthrenyl, triphenylenyl, spirofluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, 9-phenylcarbazolyl, carbazolyl, and R2, R3may be further substituted with one or more of deuterium, cyano, halogen, methyl, ethyl, n-propyl, n-butyl, iso-propyl, t-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, tolyl, biphenyl, deuterated biphenyl, terphenyl, anthracenyl, phenanthrenyl, triphenylenyl, or in case of multiple substituents, the multiple substituents are the same or different from each other; or any two adjacent R2are combined to form a substituted or unsubstituted benzene ring, naphthalene ring, or a three- to eight-membered aliphatic ring; or any two adjacent R3are combined to form a substituted or unsubstituted benzene ring, naphthalene ring, or a three- to eight-membered aliphatic ring;

[0074] R4, R5are independently selected from hydrogen, deuterium, any one or more of the following substituted or unsubstituted groups: C1-C6 alkyl, C3-C6 cycloalkyl, adamantyl, norbornyl, C6-C12 aryl, C2-C12 heteroaryl, benzocyclopentane, benzocyclohexane, benzocyclopentene, benzocyclohexene; the substituents in the “substituted or unsubstituted” are any one or more of deuterium, C1-C12 alkyl, C3-C12 cycloalkyl;

[0075] or R4, R5may form any one of the following spiro ring structures:

[0076]

[0077] R p selected from hydrogen, deuterium, or the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, n-butyl, iso-propyl, t-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthrenyl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazolyl, wherein the substituents in the “substituted or unsubstituted” are one or more of deuterium, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, iso-propyl, t-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, deuterated iso-propyl, deuterated t-butyl, deuterated cyclohexyl, deuterated cyclopentyl, deuterated cyclobutyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, or adjacent Rp They can bond together to form benzene rings or naphthalene rings;

[0078] The Ar is selected from one of isopropyl, tert-butyl, cyclohexyl, cyclopentyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, and deuterated terphenyl.

[0079] p1 is selected from 0, 1, or 2; p2 is selected from 0, 1, 2, 3, or 4; p3 is selected from 0, 1, 2, 3, 4, 5, or 6; p4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; p6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; p7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14.

[0080] The R is selected from one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, anthracene, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazoyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, and indanyl;

[0081] The n1 is selected from 0, 1, 2, 3, 4 or 5; the n2 is selected from 0, 1, 2, 3 or 4; the n3 is selected from 0, 1, 2 or 3; the n4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; and the n7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0082] More preferably, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are identical or different from each other, and are independently selected from one of the following groups:

[0083]

[0084]

[0085]

[0086] The R1 groups may be the same as or different from each other, and are independently selected from hydrogen, deuterium, or substituted or unsubstituted groups from the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, aziridine, pyrrolidine, piperidinyl, morpholinyl, thiomorpholinyl. Piperazinyl, oxazolyl, thiazolyl, imidazolyl; wherein the substituent in "substituted or unsubstituted" is selected from one or more of deuterium, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, and in the case of being substituted by multiple substituents, the multiple substituents may be the same as or different from each other;

[0087] R2, R3, and R6 are independently selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, deuterated isopropyl, deuterated tert-butyl, deuterated cyclohexyl, deuterated cyclopentyl, deuterated cyclobutyl, deuterated cyclopropyl, deuterated adamantyl, deuterated norbornel, phenyl, deuterated phenyl, tolyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, deuterated naphthyl, tetrahydronaphthyl, dihydronaphthyl, indene, and indene, or two adjacent groups bonded together to form a benzene ring;

[0088] The R c The group is selected from methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, anthracene, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazoyl, tetrahydronaphthyl, dihydronaphthyl, indene, and indene, and the above groups can be converted by deuterium, methyl... One or more of the following: alkyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, tolyl, biphenyl, terphenyl, deuterated isopropyl, deuterated tert-butyl, deuterated cyclohexyl, deuterated cyclopentyl, deuterated cyclobutyl, deuterated cyclopropyl, deuterated adamantyl, deuterated norbornel, deuterated phenyl, deuterated naphthyl, and deuterated biphenyl;

[0089] said n1 is selected from 0, 1, 2, 3, 4, or 5; said n2 is selected from 0, 1, 2, 3, or 4; said n3 is selected from 0, 1, 2, or 3; said n4 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; said n5 is selected from 0, 1, or 2; said n6 is selected from 0, 1, 2, 3, 4, 5, or 6; said n7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; said n8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; said n9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; said n 10 selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11.

[0090] Most preferably, said Ar1, Ar2, Ar3, Ar4, Ar5, Ar6are the same or different from each other and are independently selected from one of the following groups:

[0091]

[0092]

[0093]

[0094]

[0095]

[0096] Preferably, one, two, three, four, five, or six of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6are selected from one of the foregoing deuterated groups.

[0097] Preferably, said L1, L2, L3, L4, L5, L6are independently selected from a single bond or one of the following groups:

[0098]

[0099] said R x , R y are independently selected from hydrogen, deuterium, halogen, cyano, nitro, or one of the following groups: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazolyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, indenyl, or R x , R y may be combined with each other to form a substituted or unsubstituted ring;

[0100] said R zone of the following groups: methyl, ethyl, n-propyl, n-butyl, i-propyl, t-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazolyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, indenyl;

[0101] said R q one of the following groups: hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl;

[0102] said q0 is selected from 0, 1 or 2; said q1 is selected from 0, 1, 2, 3 or 4; said q2 is selected from 0, 1, 2, 3, 4, 5 or 6; said q3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0103] Further preferred, said L1, L2, L3, L4, L5, L6 are independently selected from one of the following groups:

[0104]

[0105] More preferred, said L1, L2, L3, L4, L5, L6 are independently selected from one of the following groups:

[0106]

[0107] Most preferred, said L1, L2, L3, L4, L5, L6 are independently selected from one of the following groups:

[0108]

[0109] Preferred, one, two, three, four, five or six of L1, L2, L3, L4, L5, L6 are selected from one of the foregoing deuterated groups.

[0110] Preferred, the compound of formula I fulfils at least one of the following conditions:

[0111] i. one, two, three, four, five or six of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 are selected from one of the foregoing deuterated groups;

[0112] ii. one, two, three, four, five or six of L1, L2, L3, L4, L5, L6 are selected from one of the foregoing deuterated groups.

[0113] Most preferably, the compound of Formula I satisfies at least one of the following conditions:

[0114] i. each of said Ar1and L1is selected from one of the foregoing deuterated groups;

[0115] ii. each of said Ar2and L2is selected from one of the foregoing deuterated groups;

[0116] iii. each of said Ar3and L3is selected from one of the foregoing deuterated groups;

[0117] iv. each of said Ar4and L4is selected from one of the foregoing deuterated groups;

[0118] v. each of said Ar5and L5is selected from one of the foregoing deuterated groups;

[0119] vi. each of said Ar6and L6is selected from one of the foregoing deuterated groups.

[0120] Preferably, each of said L a , L b , L c is independently selected from a single bond or one of the following groups:

[0121]

[0122] Most preferably, each of said L a , L b , L c is independently selected from a single bond or one of the following groups:

[0123]

[0124] Preferably, each of said R a , R b is the same as or different from each other and is independently selected from hydrogen, deuterium, halogen, methyl, ethyl, n-propyl, n-butyl, i-propyl, t-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, indenyl, and the foregoing groups can also be substituted with one or more of deuterium, methyl, ethyl, n-propyl, n-butyl, i-propyl, t-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, deuterated i-propyl, deuterated t-butyl, deuterated cyclohexyl, deuterated cyclopentyl, deuterated cyclobutyl, deuterated cyclopropyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl; or any two R a groups adjacent to each other are bonded together to form a substituted or unsubstituted benzene ring, or any two R bgroups are bonded together to form a substituted or unsubstituted phenyl ring.

[0125] More preferably, said R a , R b are the same or different, independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornyl, or one of the following substituents:

[0126]

[0127] Most preferably, said heterocyclic-containing arylamine compound is selected from any one of the following chemical structures:

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149] The preparation method of the heterocycle-containing arylamine compound of Formula I can be prepared by a conventional coupling reaction in the art, for example, can be prepared by the following synthetic route, but the present application is not limited thereto:

[0150] Case 1: L1, L2, L3 are single bond,

[0151]

[0152] The heterocycle-containing arylamine compound of Formula I is obtained by Buchwald-Hartwig coupling reaction to obtain intermediates A, B and C; raw material g and intermediate A are subjected to Buchwald-Hartwig coupling reaction to obtain intermediate I; intermediate I and intermediate B are subjected to Buchwald-Hartwig coupling reaction to obtain intermediate II; and intermediate II and intermediate C are subjected to Buchwald-Hartwig coupling reaction to finally obtain the compound of Formula I, wherein X1, X2, X3, X4, X5 and X6 are each independently selected from Cl, Br or I.

[0153] Case 2: L1, L2, L3 are not single bond,

[0154]

[0155] The heterocycle-containing arylamine compound of Formula I is obtained by conventional coupling reaction, wherein X1, X2, X3, X a , X b , X c are each independently selected from Cl, Br or I.

[0156] Cases 1 and 2 can also be combined, and the corresponding intermediates are selected according to L1, L2 and L3.

[0157] The source of the raw materials used in the above-mentioned reactions is not particularly limited, and commercially available products or raw materials obtained by a preparation method known to those skilled in the art can be used.

[0158] The present application also provides an organic light-emitting device comprising 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 of the anode and the cathode, and the organic layer contains any one or a combination of at least two of the heterocycle-containing arylamine compounds of the present application.

[0159] Preferably, the organic layer is located between the anode and the cathode, and the organic layer comprises a hole transport region, a light emitting layer, an electron transport region, the hole transport region and / or the light emitting layer comprising any one or a combination of at least two of the heterocyclic-containing arylamine compounds of the present application.

[0160] Preferably, the organic layer comprises a hole transport region, the hole transport region being located between the anode and the light emitting layer, and the hole transport region comprising any one or a combination of at least two of the heterocyclic-containing arylamine compounds of the present application.

[0161] Preferably, the hole transport region comprises a hole transport layer, the hole transport layer being located between the anode and the light emitting layer, and the hole transport layer comprising any one or a combination of at least two of the heterocyclic-containing arylamine compounds of the present application.

[0162] Preferably, the hole transport region comprises a hole transport layer (first hole transport layer) and / or a light emitting auxiliary layer (second hole transport layer), the light emitting auxiliary layer being located between the hole transport layer and the light emitting layer, and the hole transport layer and / or the light emitting auxiliary layer comprising any one or a combination of at least two of the heterocyclic-containing arylamine compounds of the present application.

[0163] Preferably, the organic layer comprises a light emitting layer, the light emitting layer being located between the hole transport region and the electron transport region, and the light emitting layer comprising any one or a combination of at least two of the heterocyclic-containing arylamine compounds of the present application.

[0164] Preferably, the light emitting layer comprises a host material and / or a dopant material, the host material comprising any one or a combination of at least two of the heterocyclic-containing arylamine compounds of the present application.

[0165] Preferably, the organic layer comprises an electron transport region, the electron transport region being located between the light emitting layer and the cathode, and the electron transport region comprising any one or a combination of at least two of the heterocyclic-containing arylamine compounds of the present application.

[0166] Preferably, the electron transport region comprises an electron transport layer, the electron transport layer being located between the light emitting layer and the cathode, and the electron transport layer comprising any one or a combination of at least two of the heterocyclic-containing arylamine compounds of the present application.

[0167] Preferably, the electron transport region comprises an electron transport layer and / or a hole blocking layer, the hole blocking layer being located between the light emitting layer and the electron transport layer, and the electron transport layer and / or the hole blocking layer comprising any one or a combination of at least two of the heterocyclic-containing arylamine compounds of the present application.

[0168] Preferably, the organic layer is located outside of any one of the anode and the cathode, and the organic layer comprises a cover layer containing any one or a combination of at least two of the heterocyclic-containing arylamine compounds according to the present application.

[0169] According to the direction of emitting light, the organic light-emitting diode provided by the present application can be any one of a top-emitting device, a bottom-emitting device, and a double-sided emitting device; and according to the substrate, the organic light-emitting diode provided by the present application can be a device with a rigid glass substrate or a device with a flexible substrate.

[0170] The organic light-emitting device provided by the present application can be a top-emitting light-emitting device, for example, a device comprising, in sequence on a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a transparent or semi-transparent cathode.

[0171] The organic light-emitting device provided by the present application can also be a bottom-emitting light-emitting device, for example, a device comprising, in sequence on a substrate, a transparent or semi-transparent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode structure.

[0172] The organic light-emitting device provided by the present application can also be a double-sided emitting light-emitting device, for example, a device comprising, in sequence on a substrate, a transparent or semi-transparent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a transparent or semi-transparent cathode structure.

[0173] The anode material is preferably a material with a large work function in order to enable smooth injection of holes into the organic layer. Specific examples of the anode material that can be used in the present application include metals such as vanadium, chromium, copper, zinc, gold, and alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), and combinations of metals and oxides such as ZnO:Al and SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0174] The cathode material is preferably a material with a small work function in order to enable easy injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; multi-layered structure materials such as LiF / Al and LiO2 / Al, but are not limited thereto.

[0175] The hole transport zone can include at least one selected from a hole injection layer, a hole transport layer, a hole buffer layer, and an electron blocking layer. The hole transport zone can have a single layer structure (such as a hole injection layer and / or a hole transport layer) or a single layer formed using a hole injection material and a hole transport material. In some embodiments, the hole transport zone can have, without limitation, a single layer formed using a plurality of different materials, or a multi-layer laminate structure of a hole injection layer / hole transport layer, a hole injection layer / hole transport layer / hole buffer layer, a hole injection layer / hole buffer layer, a hole transport layer / hole buffer layer, or a hole injection layer / hole transport layer / electron blocking layer laminated from the anode (e.g., on or over the anode). The thickness of the hole transport zone can be about 100 nm to about 150 nm.

[0176] The hole injection layer is a layer that injects holes from the electrode, and as a hole injection substance, a compound having a capability of transporting holes, having a hole injection effect from the anode, an excellent hole injection effect to the light emitting layer or light emitting material, preventing excitons generated in the light emitting layer from migrating to the electron injection layer or electron injection material, and having an excellent film formation capability is preferable. The HOMO (highest occupied molecular orbital) of the hole injection substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. As specific examples of the hole injection substance, there are metalloporphyrin, oligothiophene, arylamine-based organic substance, hexacyno hexaazatriphenylene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, and polyaniline and polythiophene-based conductive polymer, but are not limited thereto.

[0177] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and a substance having a large hole mobility is preferable. As specific examples, there are arylamine-based organic substance, conductive polymer, and block copolymer having both a conjugated portion and a non-conjugated portion, but are not limited thereto.

[0178] The electron blocking layer is a layer that prevents holes injected from the hole injection layer from passing through the light emitting layer to enter the electron injection layer, and thus can improve the service life and efficiency of the device, and if necessary, a known material can be used to form a suitable portion between the light emitting layer and the electron injection layer.

[0179] The light emitting substance of the light emitting layer is a substance that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine them to emit light in the visible region, and a substance having a high quantum efficiency for fluorescence or phosphorescence is preferable. As specific examples, there are 8-hydroxyquinoline aluminum complex (Alq3); carbazole-based compound; dimeric styryl compound; BAlq; 10-hydroxybenzoquinoline metal compound; benzoxazole, benzothiazole, and benzimidazole-based compound; poly(p-phenylenevinylene)-based polymer; spiro compound; polyfluorene, rubrene, and the like, but are not limited thereto.

[0180] The light-emitting layer can include a host material and a dopant material. The host material is an aromatic condensed ring derivative or a heterocycle-containing compound, etc. Specifically, as the aromatic condensed ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as the heterocycle-containing compound, there are carbazole derivatives, diphenyl furan derivatives, etc., but not limited thereto. The host material can be a single structure composed of a single substance, or a single layer structure or a multi-layer structure formed of different substances, and the host material can include a single layer, or a light-emitting layer composed of a first host material and a second host material or more.

[0181] The dopant material is an aromatic amine derivative, a styryl heterocycle-containing arylamine compound, a boron complex, a fluoranthene compound, a metal complex, etc. Specifically, as the aromatic amine derivative, it is an aromatic condensed ring derivative having a substituted or unsubstituted arylamine group, and there are pyrene, anthracene, diindenopyrene, etc. having an arylamine group, and as the styryl heterocycle-containing arylamine compound, it is a compound substituted with at least one arylvinyl group on a substituted or unsubstituted arylamine, which is substituted or unsubstituted with one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as the metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto. The dopant material can be a single structure composed of a single substance, or a single layer structure or a multi-layer structure formed of different substances.

[0182] The electron transport region can include at least one of an electron injection layer, an electron transport layer, a buffer layer, a hole blocking layer. It can be a single structure composed of a single substance, or a single layer structure or a multi-layer structure formed of different substances, and the electron transport layer can include a single layer, or a first electron transport layer and a second electron transport layer or more. The type of the electron transport region can be an electron injection layer / electron transport layer structure, an electron injection layer / electron transport layer / buffer layer structure, an electron injection layer / buffer layer structure, an electron transport layer / buffer layer structure, or an electron injection layer / electron transport layer / hole blocking layer structure, in which the layers of each structure are sequentially stacked from the cathode in the order described, but the structure of the electron transport region is not limited thereto.

[0183] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and as an electron transport substance, is a substance that can receive electrons from the cathode and transfer them to the light emitting layer, and is preferably a substance having a large electron mobility. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavone-metal complexes, and the like, but are not limited thereto. In particular, examples of a suitable cathode substance are generally substances having a low work function accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium, each of which is accompanied by an aluminum layer or a silver layer.

[0184] The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound having the ability to transport electrons, having an electron injection effect from the cathode, an excellent electron injection effect to the light emitting layer or the light emitting material, preventing the migration of excitons generated in the light emitting layer to the hole injection layer, and having excellent film formation ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenylquinone, oxazole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylmethane, anthrone, and the like, as well as their derivatives, metal complexes, and nitrogen-containing 5-membered ring derivatives, but are not limited thereto. The metal complexes are lithium 8-hydroxyquinolate, zinc bis(8-hydroxyquinolate), copper bis(8-hydroxyquinolate), manganese bis(8-hydroxyquinolate), aluminum tris(8-hydroxyquinolate), aluminum tris(2-methyl-8-hydroxyquinolate), gallium tris(8-hydroxyquinolate), beryllium bis(10-hydroxybenzo[h]quinoline), zinc bis(10-hydroxybenzo[h]quinoline), gallium bis(2-methyl-8-quinoline) chloride, gallium bis(2-methyl-8-quinoline)(o-cresol), aluminum bis(2-methyl-8-quinoline)(1-naphthol), and the like, but are not limited thereto.

[0185] The hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed using the same conditions as the hole injection layer. Specifically, there are diazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

[0186] The cover layer can be selected from Alq3, TPBi, and the like, and other known materials suitable for a cover layer can also be selected, and the heterocycle-containing arylamine compound described in the present application can also be selected.

[0187] The method of forming each layer in the organic light emitting device is not particularly limited, and can be formed using a vacuum evaporation method, a spin coating method, a vapor deposition method, a doctor blade method, a Langmuir-Blodgett method, a laser printing method, a laser-induced thermal imaging (LITI) method.

[0188] The organic light emitting device described in the present application can be widely used in the fields of panel displays, illumination light sources, flexible OLEDs, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, signboards, signal lights, and the like.

[0189] The present application is explained in greater detail by the following examples, but is not intended to be limited thereby. On the basis of this description, a person of ordinary skill in the art will be able to implement the present application and prepare other compounds and devices according to the present application within the entire scope disclosed, without paying creative labor.

[0190] Explanation of raw materials, reagents and characterization equipment:

[0191] The present application does not have a particular limitation on the source of raw materials used in the following examples, which can be commercially available products or prepared by methods well known to those skilled in the art.

[0192] Mass spectrometry uses a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer in the United Kingdom, with chloroform as the solvent;

[0193] Elemental analysis uses a Vario EL cube organic elemental analyzer from Elementar, Germany, with a sample mass of 5-10 mg.

[0194] Synthesis Example 1: Preparation of compound 10

[0195]

[0196] Preparation of intermediate A-10:

[0197] Under nitrogen protection, a-10 (10.52 g, 67.00 mmol), b-10 (6.24 g, 67.00 mmol), sodium tert-butoxide (11.53 g, 120.00 mmol) were added to 350 ml of toluene, Pd(dppf)Cl2(0.59 g, 0.80 mmol) was added with stirring, and the mixture was heated to reflux for 4.5 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, and dichloromethane was used for extraction, and the organic layer was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure, and the crystals were separated by cooling, filtered, and the obtained solid was recrystallized with ethyl acetate to obtain intermediate A-10 (9.30 g, 82%), with a solid purity of ≧99.66% detected by HPLC. Mass spectrometry m / z: 169.0899 (theoretical value: 169.0891).

[0198] Preparation of intermediate B-10:

[0199] Under nitrogen protection, c-10 (14.58 g, 90.00 mmol), b-10 (8.38 g, 90.00 mmol), sodium tert-butoxide (13.45 g, 140.00 mmol) were added into 350 mL of toluene, Pd(dppf)Cl2(0.73 g, 1.00 mmol) was added under stirring, the mixture was heated to reflux for 5 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and dichloromethane was used for extraction, the organic phase was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure, and the solid was obtained by crystallization, which was recrystallized with ethyl acetate to obtain intermediate B-10 (13.17 g, 84%), the solid purity was ≧99.68% by HPLC detection. Mass spectrum m / z: 174.1218 (theoretical value: 174.1205).

[0200] Preparation of intermediate I-10:

[0201] Under nitrogen protection, intermediate A-10 (9.48 g, 56.00 mmol), g-10 (17.69 g, 56.00 mmol), sodium tert-butoxide (9.61 g, 100.00 mmol) were added into 270 mL of toluene, Pd(OAc)2(0.14 g, 0.64 mmol), P(t-Bu)3(2.56 mL of 0.5 M toluene solution, 1.28 mmol) were added under stirring, the mixture was heated to reflux for 6 h. After the reaction was completed, the mixture was cooled to room temperature, dichloromethane and distilled water were added for extraction, the organic phase was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure, and purified by silica gel column chromatography with petroleum ether / dichloromethane (volume ratio 9:1) to obtain intermediate I-10 (17.43 g, 77%), the solid purity was ≧99.78% by HPLC detection. Mass spectrum m / z: 403.0545 (theoretical value: 403.0531).

[0202] Preparation of compound 10:

[0203] To a mixture of intermediate 1-10 (14.15 g, 35.00 mmol), intermediate B-10 (12.20 g, 70.00 mmol), sodium tert-butoxide (6.73 g, 70.00 mmol) in 160 mL of toluene was added under nitrogen atmosphere, Pd2(dba)3(0.40 g, 0.43 mmol), X-Phos (0.41 g, 0.85 mmol) was added with stirring, the mixture was heated to reflux for 5.5 h. After completion of the reaction, the mixture was cooled to room temperature, distilled water was added, extracted with dichloromethane, allowed to separate, the organic layer was collected and dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated under reduced pressure, the solid was obtained by cooling and crystallization, the solid was recrystallized from toluene to obtain compound 10 (18.09 g, 76%), the purity of the solid was > 99.94% as determined by HPLC. Mass (m / z): 679.3400 (calculated: 679.3408). Theoretical elemental content (%) C 48 H 25 D 10 N3O: C, 84.80; H, 6.67; N, 6.18. Found: C, 84.86; H, 6.61; N, 6.22.

[0204] Synthesis Example 2: Preparation of compound 19

[0205]

[0206] Intermediate B-10 was obtained according to the same preparation method as intermediate B-10 in synthesis example 1.

[0207] To a mixture of intermediate B-10 (18.30 g, 105.00 mmol), g-19 (14.17 g, 35.00 mmol), sodium tert-butoxide (6.73 g, 70.00 mmol) in 200 mL of toluene was added under nitrogen atmosphere, Pd2(dba)3(0.38 g, 0.42 mmol), P(t-Bu)3(1.68 mL of 0.5 M solution in toluene, 0.84 mmol) was added with stirring, the mixture was heated to reflux for 5 h. After completion of the reaction, the mixture was cooled to room temperature, dichloromethane and distilled water were added to the mixture and extracted, allowed to separate, the organic layer was collected and dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated under reduced pressure, the solid was obtained by cooling and crystallization, the solid was recrystallized from toluene to obtain compound 19 (16.54 g, 69%), the purity of the solid was > 99.93% as determined by HPLC. Mass (m / z): 684.3708 (calculated: 684.3722). Theoretical elemental content (%) C 48 H 20 D 15N3O: C, 82.36; H, 9.35; N, 6.00. Found: C, 82.38; H, 9.32; N, 6.04.

[0208] [Synthesis Example 3] Synthesis of compound 30

[0209]

[0210] According to the same preparation method as synthesis example 2, b-10 was replaced by equimolar b-30, g-19 was replaced by equimolar g-30, to obtain compound 30 (16.66 g), solid purity ≥ 99.96% detected by HPLC. Mass m / z: 699.4671 (theoretical value: 699.4663). Theoretical elemental content (%) C 48 H5D 30 N3O: C, 82.36; H, 9.35; N, 6.00. Found: C, 82.38; H, 9.32; N, 6.04.

[0211] [Synthesis Example 4] Synthesis of compound 41

[0212]

[0213] According to the same preparation method as synthesis example 1, a-10 was replaced by equimolar a-41, c-10 was replaced by equimolar c-41, g-10 was replaced by equimolar g-41, to obtain compound 41 (22.86 g), solid purity ≥ 99.93% detected by HPLC. Mass m / z: 906.4272 (theoretical value: 906.4284). Theoretical elemental content (%) C 66 H 38 D9N3O: C, 87.38; H, 6.22; N, 4.63. Found: C, 87.40; H, 6.19; N, 4.65.

[0214] [Synthesis Example 5] Synthesis of compound 50

[0215]

[0216] According to the same preparation method as synthesis example 2, c-10 was replaced by equimolar a-50, to obtain compound 50 (21.41 g), solid purity ≥ 99.95% detected by HPLC. Mass m / z: 912.4677 (theoretical value: 912.4661). Theoretical elemental content (%) C 66 H 32 D 15N3O: C, 86.81 ; H, 6.84; N, 4.60. Found ( % ) : C, 86.85; H, 6.80; N, 4.63.

[0217] [Synthesis Example 6] Synthesis of compound 66

[0218]

[0219] According to the same preparation method as synthesis example 2, c-10 was replaced with equimolar a-66, b-10 was replaced with equimolar b-30, compound 66 (24.74 g) was obtained, solid purity ≥ 99.97% detected by HPLC. Mass m / z: 1140.5610 (theoretical value: 1140.5600). Theoretical elemental content (%) C 84 H 44 D 15 N3O: C, 88.39; H, 6.53; N, 3.68. Found ( % ) : C, 88.43; H, 6.50; N, 3.66.

[0220] [Synthesis Example 7] Synthesis of compound 78

[0221]

[0222] According to the same preparation method as synthesis example 2, c-10 was replaced with equimolar a-78, b-10 was replaced with equimolar b-30, g-10 was replaced with equimolar g-30, compound 78 (18.99 g) was obtained, solid purity ≥ 99.94% detected by HPLC. Mass m / z: 834.4180 (theoretical value: 834.4191). Theoretical elemental content (%) C 60 H 26 D 15 N3O: C, 86.30; H, 6.76; N, 5.03. Found ( % ) : C, 86.35; H, 6.74; N, 5.01.

[0223] [Synthesis Example 8] Synthesis of compound 85

[0224]

[0225] According to the same preparation method as synthesis example 1, a-10 was replaced with equimolar a-85, b-10 in intermediate A-10 was replaced with equimolar b-30, c-10 was replaced with equimolar c-41, compound 85 (22.52 g) was obtained, solid purity ≥ 99.95% detected by HPLC. Mass m / z: 959.4636 (theoretical value: 959.4629). Theoretical elemental content (%) C70 H 37 D 12 N3O: C, 87.56; H, 6.40; N, 4.38. Found: C, 87.59; H, 6.37; N, 4.40.

[0226] [Synthesis Example 9] Synthesis of compound 115

[0227]

[0228] According to the same preparation method as synthesis example 1, a-10 is replaced with an equal mole of a-115, b-10 in intermediate A-10 is replaced with an equal mole of b-115, to obtain compound 115 (17.74 g, 64%), solid purity ≥ 99.92% detected by HPLC. Mass spectrum m / z: 791.4672 (theoretical value: 791.4660). Theoretical elemental content (%) C 56 H 41 D 10 N3O: C, 84.92; H, 7.76; N, 5.30. Found: C, 84.95; H, 7.72; N, 5.33

[0229] [Synthesis Example 10] Synthesis of compound 125

[0230]

[0231] According to the same preparation method as synthesis example 2, c-10 is replaced with an equal mole of a-125, b-10 is replaced with an equal mole of b-30, and g-19 is replaced with an equal mole of g-30, to obtain compound 125 (27.41 g), solid purity ≥ 99.96% detected by HPLC. Mass spectrum m / z: 1086.7000 (theoretical value: 1086.7008). Theoretical elemental content (%) C 78 H 62 D 15 N3O: C, 86.14; H, 8.52; N, 3.86. Found: C, 86.17; H, 8.50; N, 3.83.

[0232] [Synthesis Example 11] Synthesis of compound 127

[0233]

[0234] Following the same preparation method as in synthesis example 2, c-10 was replaced with an equivalent molar of a-127, b-10 was replaced with an equivalent molar of b-30, g-19 was replaced with an equivalent molar of g-30, to obtain compound 127 (21.62 g) with solid purity > 99.93% as detected by HPLC. Mass spectrum m / z: 894.6079 (theoretical value: 894.6069). Theoretical elemental content (%) C 63 H 50 D 15 N3O: C, 84.52; H, 9.00; N, 4.69. Actual elemental content (%) : C, 84.50; H, 9.05; N, 4.64

[0235] [Synthesis example 12] Synthesis of compound 129

[0236]

[0237] Following the same preparation method as in synthesis example 2, c-10 was replaced with an equivalent molar of a-129, b-10 was replaced with an equivalent molar of b-30, g-19 was replaced with an equivalent molar of g-30, to obtain compound 129 (19.71 g) with solid purity > 99.96% as detected by HPLC. Mass spectrum m / z: 804.4653 (theoretical value: 804.4661). Theoretical elemental content (%) C 57 H 32 D 15 N3O: C, 85.03; H, 7.76; N, 5.22. Actual elemental content (%) : C, 85.00; H, 7.79; N, 5.25.

[0238] [Synthesis example 13] Synthesis of compound 150

[0239]

[0240] Following the same preparation method as in synthesis example 1, a-10 was replaced with an equivalent molar of a-150, g-10 was replaced with an equivalent molar of g-85, to obtain compound 150 (19.96 g) with solid purity > 99.92% as detected by HPLC. Mass spectrum m / z: 863.4649 (theoretical value: 863.4660). Theoretical elemental content (%) C 62 H 41 D 10 N3O: C, 86.17; H, 7.11; N, 4.86. Actual elemental content (%) : C, 86.12; H, 7.08; N, 4.90.

[0241] [Synthesis example 14] Synthesis of compound 165

[0242]

[0243] Following the same preparation method as in synthesis example 2, replacing c-10 with an equal molar of a-165, g-19 with an equal molar of g-165, compound 165 (24.16 g) was obtained with a solid purity > 99.95% by HPLC. Mass m / z: 1029.5420 (calcd: 1029.5411). Theoretical elemental content (%) C 75 H 47 D 12 N3O: C, 87.43; H, 6.94; N, 4.08. Found elemental content (%) C, 87.41; H, 6.97; N, 4.05.

[0244] [Synthesis Example 15] Synthesis of compound 169

[0245]

[0246] Following the same preparation method as in synthesis example 2, replacing c-10 with an equal molar of a-169, b-10 with an equal molar of b-30, g-19 with an equal molar of g-30, compound 169 (24.56 g) was obtained with a solid purity > 99.92% by HPLC. Mass m / z: 1032.5610 (calcd: 1032.5600). Theoretical elemental content (%) C 75 H 44 D 15 N3O: C, 87.17; H, 7.22; N, 4.07. Found elemental content (%) C, 87.14; H, 7.18; N, 4.11.

[0247] [Synthesis Example 16] Synthesis of compound 198

[0248]

[0249] Following the same preparation method as in synthesis example 1, replacing a-10 with an equal molar of a-198, compound 198 (22.07 g) was obtained with a solid purity > 99.96% by HPLC. Mass m / z: 887.4651 (calcd: 887.4660). Theoretical elemental content (%) C 64 H 41 D 10 N3O: C, 86.55; H, 6.92; N, 4.73. Found elemental content (%) C, 86.52; H, 6.95; N, 4.70.

[0250] [Synthesis Example 17] Synthesis of compound 211

[0251]

[0252] Following the same preparation procedure as in the synthesis of Example 1, a-10 was replaced with an equivalent molar of a-211, b-10 was replaced with an equivalent molar of b-211, and g-10 was replaced with an equivalent molar of g-85 to give compound 211 (24.40 g) with a solid purity > 99.93% as determined by HPLC. Mass spectrum m / z: 1071.4960 (calcd 1071.4973). Theoretical elemental content (%) C 79 H 45 D 10 N3O: C, 88.48; H, 6.11; N, 3.92. Found: C, 88.45; H, 6.15; N, 3.90.

[0253] [Synthesis Example 18] Synthesis of compound 275

[0254]

[0255] Following the same preparation procedure as in the synthesis of Example 1, a-10 was replaced with an equivalent molar of a-275, and b-10 of intermediate A-10 was replaced with an equivalent molar of b-275 to give compound 275 (24.82 g) with a solid purity > 99.96% as determined by HPLC. Mass spectrum m / z: 1057.5760 (calcd 1057.5755). Theoretical elemental content (%) C 77 H 55 D 10 N3O: C, 87.38; H, 7.14; N, 3.97. Found: C, 87.36; H, 7.16; N, 3.94.

[0256] [Synthesis Example 19] Synthesis of compound 282

[0257]

[0258] Following the same preparation procedure as in the synthesis of Example 1, a-10 was replaced with an equivalent molar of a-282, and b-10 of intermediate A-10 was replaced with an equivalent molar of b-282 to give compound 282 (23.77 g) with a solid purity > 99.94% as determined by HPLC. Mass spectrum m / z: 983.5590 (calcd 983.5599). Theoretical elemental content (%) C 71 H 53 D 10 N3O: C, 86.63; H, 7.47; N, 4.27. Found: C, 86.66; H, 7.44; N, 4.23.

[0259] [Synthesis Example 20] Synthesis of compound 286

[0260]

[0261] According to the same preparation method as synthesis example 1, a-10 was replaced with an equal mole of a-286, c-10 was replaced with an equal mole of c-286, to obtain compound 286 (23.77 g), with solid purity ≥ 99.97% detected by HPLC. Mass spectrum m / z: 1033.5682 (theoretical value: 1033.5693). Theoretical elemental content (%) C 75 H 47 D 14 N3O: C, 87.09; H, 7.31; N, 4.06. Measured elemental content (%) C, 87.05; H, 7.35; N, 4.03.

[0262] [Synthesis Example 21] Synthesis of compound 301

[0263]

[0264] According to the same preparation method as synthesis example 1, a-10 was replaced with an equal mole of a-301, to obtain compound 301 (24.52 g), with solid purity ≥ 99.95% detected by HPLC. Mass spectrum m / z: 1029.5428 (theoretical value: 1029.5442). Theoretical elemental content (%) C 75 H 51 D 10 N3O: C, 87.43; H, 6.94; N, 4.08. Measured elemental content (%) C, 87.45; H, 6.91; N, 4.05.

[0265] [Synthesis Example 22] Synthesis of compound 330

[0266]

[0267] According to the same preparation method as synthesis example 2, c-10 was replaced with an equal mole of a-330, b-10 was replaced with an equal mole of b-30, g-19 was replaced with an equal mole of g-30, to obtain compound 330 (23.40 g), with solid purity ≥ 99.97% detected by HPLC. Mass spectrum m / z: 954.4048 (theoretical value: 954.4039). Theoretical elemental content (%) C 66 H 26 D 15 N3O4: C, 82.99; H, 5.91; N, 4.40. Measured elemental content (%) C, 82.94; H, 5.95; N, 4.43.

[0268] [Synthesis Example 23] Synthesis of compound 339

[0269]

[0270] According to the same preparation method as synthesis example 1, a-10 was replaced with an equal mole of a-339, b-10 of intermediate A-10 was replaced with an equal mole of b-387, and g-10 was replaced with an equal mole of g-85, to obtain compound 387 (21.90 g) with a solid purity ≥ 99.97% detected by HPLC. Mass spectrum m / z: 919.4001 (theoretical value: 919.4014). Theoretical elemental content (%) C 58 H 29 D 10 N3O2: C, 84.95; H, 6.02; N, 5.12. Measured elemental content (%) C, 84.92; H, 6.05; N, 5.09.

[0271] [Synthesis Example 24] Synthesis of compound 387

[0272]

[0273] According to the same preparation method as synthesis example 1, a-10 was replaced with an equal mole of a-339, b-10 of intermediate A-10 was replaced with an equal mole of b-387, and g-10 was replaced with an equal mole of g-85, to obtain compound 387 (21.90 g) with a solid purity ≥ 99.97% detected by HPLC. Mass spectrum m / z: 919.4001 (theoretical value: 919.4014). Theoretical elemental content (%) C 66 H 37 D8N3O2: C, 86.15; H, 5.80; N, 4.57. Measured elemental content (%) C, 86.13; H, 5.85; N, 4.54.

[0274] [Synthesis Example 25] Synthesis of compound 395

[0275]

[0276] According to the same preparation method as synthesis example 1, a-10 was replaced with an equal mole of a-339, b-10 of intermediate A-10 was replaced with an equal mole of b-387, and g-10 was replaced with an equal mole of g-85, to obtain compound 387 (21.90 g) with a solid purity ≥ 99.97% detected by HPLC. Mass spectrum m / z: 919.4001 (theoretical value: 919.4014). Theoretical elemental content (%) C 66 H 33 D 10 N3O3: C, 84.68; H, 5.70; N, 4.49. Measured elemental content (%) C, 84.66; H, 5.74; N, 4.45.

[0277] [Synthesis Example 26] Synthesis of compound 400

[0278]

[0279] According to the same preparation method as synthesis example 1, a-10 was replaced with an equal mole of a-400, g-10 was replaced with an equal mole of g-85, to obtain compound 400 (21.62 g), with solid purity ≥ 99.96% detected by HPLC. Mass spectrum m / z: 845.3819 (theoretical value: 845.3826). Theoretical elemental content (%) C 60 H 31 D 10 N3O2: C, 85.18; H, 6.07; N, 4.97. Measured elemental content (%) C, 85.14; H, 6.09; N, 4.93.

[0280] [Synthesis Example 27] Synthesis of compound 426

[0281]

[0282] According to the same preparation method as synthesis example 1, a-10 was replaced with an equal mole of a-426, c-10 was replaced with an equal mole of c-426, to obtain compound 426 (18.71 g), with solid purity ≥ 99.93% detected by HPLC. Mass spectrum m / z: 809.3340 (theoretical value: 809.3347). Theoretical elemental content (%) C 56 H 36 D6N3OS: C, 83.03; H, 5.85; N, 5.19. Measured elemental content (%) C, 83.06; H, 5.82; N, 5.16.

[0283] [Synthesis Example 28] Synthesis of compound 450

[0284]

[0285] According to the same preparation method as synthesis example 1, a-10 was replaced with an equal mole of a-450, b-10 in intermediate A-10 was replaced with an equal mole of b-30, c-10 was replaced with an equal mole of c-450, to obtain compound 450 (23.38 g), with solid purity ≥ 99.97% detected by HPLC. Mass spectrum m / z: 996.4604 (theoretical value: 996.4612). Theoretical elemental content (%) C 72 H 40 D 10 N4O: C, 86.72; H, 6.06; N, 5.62. Measured elemental content (%) C, 86.76; H, 6.00; N, 5.60.

[0286] [Synthesis Example 29] Synthesis of compound 452

[0287]

[0288] According to the same preparation method as synthesis example 1, a-10 was replaced with an equivalent of a-452 to obtain compound 452 (20.40 g) with solid purity ≥ 99.95% detected by HPLC. Mass spectrum m / z: 844.3979 (theoretical value: 844.3986). Theoretical elemental content (%) C 60 H 32 D 10 N4O: C, 85.28; H, 6.20; N, 6.63. Measured elemental content (%) : C, 85.24; H, 6.25; N, 6.59.

[0289] [Synthesis Example 30] Synthesis of compound 479

[0290]

[0291] According to the same preparation method as synthesis example 1, a-10 was replaced with an equivalent of a-479 to obtain compound 479 (22.57 g) with solid purity ≥ 99.92% detected by HPLC. Mass spectrum m / z: 920.4291 (theoretical value: 920.4299). Theoretical elemental content (%) C 66 H 36 D 10 N4O: C, 86.06; H, 6.13; N, 6.08. Measured elemental content (%) : C, 86.03; H, 6.15; N, 6.04.

[0292] [Synthesis Example 31] Synthesis of compound 481

[0293]

[0294] According to the same preparation method as synthesis example 1, a-10 was replaced with an equivalent of a-481 to obtain compound 481 (23.54 g) with solid purity ≥ 99.96% detected by HPLC. Mass spectrum m / z: 933.4130 (theoretical value: 933.4139). Theoretical elemental content (%) C 67 H 35 D 10 N3O2: C, 86.14; H, 5.93; N, 4.50. Measured elemental content (%) : C, 86.11; H, 5.95; N, 4.53.

[0295] [Synthesis Example 32] Synthesis of compound 508

[0296]

[0297] Following the same preparation method as in synthesis example 2, c-10 is replaced by an equivalent molar of a-508, g-19 is replaced by an equivalent molar of g-508, to obtain compound 508 (22.12 g) with a solid purity > 99.94% by HPLC. Mass spectrum m / z: 928.4440 (theoretical value: 928.4432). Theoretical elemental content (%) C 66 H 32 D 15 N3S: C, 85.31 ; H, 6.72; N, 4.52. Found elemental content (%) : C, 85.29; H, 6.75; N, 4.49.

[0298] [Synthesis example 33] Synthesis of compound 590

[0299]

[0300] Following the same preparation method as in synthesis example 1, a-10 is replaced by an equivalent molar of a-590, b-10 in intermediate A-10 is replaced by an equivalent molar of b-590, g-10 is replaced by an equivalent molar of g-590, to obtain compound 590 (24.71 g) with a solid purity > 99.93% by HPLC. Mass spectrum m / z: 993.3989 (theoretical value: 993.3996). Theoretical elemental content (%) C 69 H 39 D 10 N3S2: C, 83.35; H, 5.98; N, 4.23. Found elemental content (%) : C, 83.31 ; H, 5.99; N, 4.21.

[0301] [Synthesis example 34] Synthesis of compound 596

[0302]

[0303] The preparation method of intermediate A-10 is the same as that of intermediate A-10 in compound 10;

[0304] Preparation of intermediate I-596:

[0305] Into a reaction flask was placed g-596 (32.44 g, 90.00 mmol), A-10 (30.80 g, 182.00 mmol), Pd(OAc)2(0.22 g, 1.00 mmol), BINAP (1.25 g, 2.00 mmol), sodium tert-butoxide (17.30 g, 180.00 mmol) under nitrogen protection, then 300 mL of toluene was added, heated to reflux for 6 hours, after the reaction was completed. Naturally cooled to room temperature, filtered with diatomite, concentrated the filtrate by distillation under reduced pressure, purified by column chromatography (n-hexane: ethyl acetate = 9: 1) to obtain intermediate I-596 (34.80 g, yield 72%), the solid purity was ≥99.82% detected by HPLC. Mass spectrum m / z: 536.1644 (theoretical value: 536.1655).

[0306] Synthesis of compound 596

[0307] Into a reaction flask was placed intermediate I-596 (26.85 g, 50.00 mmol), intermediate i-596 (18.82 g, 50.00 mmol), K2CO3(20.73 g, 150.00 mmol), Pd(PPh3)4(0.75 g, 0.65 mmol) under nitrogen protection, 250 mL of tetrahydrofuran was added, the mixture was stirred, and the above reaction system was heated to reflux for 8 hours. After the reaction was completed, it was cooled to room temperature, toluene was added, and the phases were separated, the toluene phase was washed with distilled water three times, dried with anhydrous magnesium sulfate, concentrated the solvent by rotary evaporation, crystallized by cooling, filtered, and the obtained solid was recrystallized with toluene to obtain compound 596 (23.28 g, yield 62%). The solid purity was ≥99.94% detected by HPLC. Mass spectrum m / z: 750.3419 (theoretical value: 750.3407). Theoretical elemental content (%) 54 H 34 D5N3O: C, 86.37; H, 5.90; N, 5.60. Found elemental content (%): C, 86.40; H, 5.88; N, 5.60.

[0308]

[0309] According to the same preparation method as in synthesis example 34, a-10 was replaced by an equal molar amount of a-643, and g-596 was replaced by an equal molar amount of g-643 to obtain compound 643 (29.13 g), the solid purity was ≥99.92% detected by HPLC. Mass spectrum m / z: 970.4104 (theoretical value: 970.4118). Theoretical elemental content (%) 70 H 46D5N3S: C, 86.56; H, 5.81; N, 4.33. Found (%): C, 86.58; H, 5.78; N, 4.31.

[0310]

[0311] Preparation of intermediate M: under nitrogen protection, raw material m (22.77 g, 105.00 mmol), raw material n (26.72 g, 105.00 mmol), Pd(PPh3)4(2.31 g, 2.00 mmol), K2CO3(25.57 g, 185.00 mmol), THF (300 mL), H2O (150 mL) were added and refluxed at 90 °C for 10 hours. When the reaction was completed, the temperature of the reaction product was cooled to room temperature, dichloromethane and distilled water were added to the mixture and extracted, and the organic layer was dried over MgSO4and concentrated, and the resulting compound was recrystallized with toluene to obtain intermediate M (23.90 g, 76%). The solid purity was > 99.34% detected by HPLC. Mass spectrum m / z: 297.9378 (theoretical value: 297.9396).

[0312] Preparation of intermediate N: under nitrogen protection, to intermediate M (22.47 g, 75.00 mmol) were added Pd(OAc)2(0.34 g, 1.50 mmol), 3-nitropyridine (0.19 g, 1.50 mmol), tert-butyl peroxybenzoate (27.61 g, 140.00 mmol), hexafluorobenzene 180 ml, N,N'-dimethylimidazolidinone 120 ml, and refluxed at 90 °C for 12 hours. When the reaction was completed, the temperature of the reaction product was cooled to room temperature, ethyl acetate and distilled water were added to the mixture and extracted. The organic layer was dried over MgSO4and concentrated, and the resulting compound was recrystallized with toluene to obtain intermediate N (13.83 g, 62%). The solid purity was > 99.41% detected by HPLC. Mass spectrum m / z: 295.9253 (theoretical value: 295.9240).

[0313] Preparation of intermediate g-662: under nitrogen protection, to intermediate N (13.39 g, 45.00 mmol) was added excess triflic acid, stirred at room temperature for 24 hours, then water and pyridine (8: 1) were slowly added and refluxed for 30 minutes. The temperature was reduced, and dichloromethane and distilled water were added to the mixture and extracted. The organic layer was dried over MgSO4and concentrated, and the resulting compound was recrystallized with toluene to obtain intermediate g-662 (15.27 g, 79%). The solid purity was > 99.52% detected by HPLC. Mass spectrum m / z: 427.870 (theoretical value: 427.8733).

[0314] The preparation of intermediate A-662, the preparation of intermediate B-41, the preparation of intermediate C-662 were obtained according to the same preparation method as intermediate A-10 in synthesis example 1.

[0315] Preparation of intermediate I-662:

[0316] Under nitrogen protection, intermediate B-41 (8.59 g, 35.00 mmol), intermediate g-662 (15.04 g, 35.00 mmol), sodium tert-butoxide (6.25 g, 65.00 mmol) were added into 250 ml of toluene, Pd(OAc)2(0.09 g, 0.38 mmol), P(t-Bu)3(1.52 mL of 0.5 M toluene solution, 0.76 mmol) were added with stirring, the mixture solution was heated to reflux for 6 h. After the reaction was completed, it was cooled to room temperature, dichloromethane and distilled water were added to the mixture for extraction, the organic phase was collected and dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated under reduced pressure, purified by silica gel column chromatography with n-hexane / dichloromethane (volume ratio 9:1) to obtain intermediate I-662 (15.06 g, 82%), the solid purity was > 99.61% by HPLC detection. Mass spectrum m / z: 523.0352 (theoretical value: 523.0339).

[0317] Preparation of intermediate II-662:

[0318] Under nitrogen protection, intermediate I-662 (14.70 g, 28.00 mmol), intermediate A-662 (6.87 g, 28.00 mmol), sodium tert-butoxide (4.32 g, 45.00 mmol) were added into 150 ml of toluene, Pd2(dba)3(0.26 g, 0.28 mmol), P(t-Bu)3(1.12 mL of 0.5 M toluene solution, 0.56 mmol) were added with stirring, the mixture solution was heated to reflux for 5 h. After the reaction was completed, it was cooled to room temperature, dichloromethane and distilled water were added to the mixture for extraction, the organic phase was collected and dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated under reduced pressure, purified by silica gel column chromatography with petroleum ether / ethyl acetate (volume ratio 8:1) to obtain intermediate II-662 (14.86 g, 77%), the solid purity was > 99.84% by HPLC detection. Mass spectrum m / z: 688.2296 (theoretical value: 688.2281).

[0319] Preparation of compound 662:

[0320] Under nitrogen protection, intermediate II-662 (13.79 g, 20.00 mmol), intermediate C-662 (6.53 g, 20.00 mmol), sodium tert-butoxide (3.84 g, 40.00 mmol) were added into 150 ml of toluene, Pd2(dba)3(0.23 g, 0.25 mmol), X-Phos (0.24 g, 0.50 mmol) were added under stirring, the mixture was heated to reflux for 5 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, separated by standing, the organic layer was collected and dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated by reduced pressure distillation, crystallized by cooling, filtered under suction, the obtained solid was recrystallized with toluene to obtain compound 662 (14.30 g, 73%), the solid purity was ≥99.94% detected by HPLC. Mass spectrum m / z: 978.4331 (theoretical value: 978.4346). Theoretical elemental content (%) C 72 H 46 D5N3O: C, 88.31; H, 5.76; N, 4.29. Measured elemental content (%): C, 88.29; H, 5.77; N, 4.30.

[0321] [Synthesis Example 37] Synthesis of compound 671

[0322]

[0323] According to the same preparation method as synthesis example 1, a-10 was replaced by an equal molar of a-671, b-10 in intermediate A-10 was replaced by an equal molar of b-30, c-10 was replaced by an equal molar of c-41, g-10 was replaced by an equal molar of g-85, to obtain compound 671 (21.59 g), the solid purity was ≥99.98% detected by HPLC. Mass spectrum m / z: 978.4331 (theoretical value: 978.4346). Theoretical elemental content (%) C 72 H 46 D5N3O: C, 88.31; H, 5.76; N, 4.29. Measured elemental content (%): C, 88.29; H, 5.77; N, 4.30.

[0324] [Synthesis Example 38] Synthesis of compound 705

[0325]

[0326] Following the same preparation method as in Synthesis Example 1, a-10 was replaced with an equal molar of a-705, b-10 in Intermediate A-10 was replaced with an equal molar of b-30, c-10 was replaced with an equal molar of c-705, to produce compound 705 (22.99 g) with a solid purity > 99.95% as tested by HPLC. Mass spectrum m / z: 924.4829 (calcd 924.4815). Theoretical elemental content (%) C 67 H 52 D5N3O: C, 86.98; H, 6.75; N, 4.54. Found elemental content (%) C, 86.96; H, 6.78; N, 4.55.

[0327] [Synthesis Example 39] Synthesis of compound 711

[0328]

[0329] Following the same preparation method as in Synthesis Example 1, a-10 was replaced with an equal molar of a-711, b-10 in Intermediate A-10 was replaced with an equal molar of b-30, c-10 was replaced with an equal molar of c-450, g-10 was replaced with an equal molar of g-85, to produce compound 711 (22.23 g) with a solid purity > 99.91% as tested by HPLC. Mass spectrum m / z: 920.4061 (calcd 920.4077). Theoretical elemental content (%) C 66 H 36 D9N3O2: C, 86.06; H, 5.91; N, 4.56. Found elemental content (%) C, 86.07; H, 5.90; N, 4.53.

[0330] [Synthesis Example 40] Synthesis of compound 718

[0331]

[0332] Following the same preparation method as in Synthesis Example 1, a-10 was replaced with an equal molar of a-718, b-10 in Intermediate A-10 was replaced with an equal molar of b-30, c-10 was replaced with an equal molar of c-718, g-10 was replaced with an equal molar of g-85, to produce compound 718 (20.51 g) with a solid purity > 99.94% as tested by HPLC. Mass spectrum m / z: 944.4148 (calcd 944.4139). Theoretical elemental content (%) C 68 H 44 D5N3O2: C, 86.41; H, 5.76; N, 4.45. Found elemental content (%) C, 86.40; H, 5.75; N, 4.48.

[0333] Green organic light-emitting device (hole transport layer)

[0334] [Comparative Example 1-2] Device preparation example:

[0335] Comparative Example 1: An organic light-emitting device was prepared by a vacuum thermal evaporation method. The experimental steps were as follows: the ITO substrate was cleaned in distilled water for 3 times, ultrasonic washing for 15 minutes, after the distilled water cleaning, the solvents such as isopropanol, acetone, and methanol were sequentially ultrasonic washed, and then dried at 120℃, and sent to the evaporation machine.

[0336] On the prepared ITO transparent electrode, a hole injection layer HATCN / 42 nm was evaporated by layer-by-layer vacuum evaporation, a hole transport layer HT-1 / 60 nm was evaporated, a main body m-CBP: doped Ir(ppy)2acac (mass ratio 95%:5% mixture) / 21 nm was evaporated, and then an electron transport layer ETL and Liq (doping ratio mass ratio 1:1) / 29 nm, an electron injection layer LiF / 0.8 nm, and a cathode Al / 125 nm were evaporated. The device was sealed in a glove box, thereby preparing an organic light-emitting device. After the preparation of the organic light-emitting device was completed according to the above steps, the photoelectric performance of the device was measured, and the molecular structure of the related material is shown as follows:

[0337]

[0338] Comparative Example 2: The hole transport layer material HT-1 in Comparative Example 1 was replaced by HT-2, and the organic light-emitting device of Comparative Example 2 was manufactured in the same way as Comparative Example 1.

[0339] Comparative Example 3: The hole transport layer material HT-1 in Comparative Example 1 was replaced by HT-3, and the organic light-emitting device of Comparative Example 3 was manufactured in the same way as Comparative Example 1.

[0340] [Application Examples 1-40]

[0341] Application Examples 1-40: The hole transport layer material HT-1 of the organic light-emitting device was replaced by the compounds 10, 19, 30, 41, 50, 66, 78, 85, 115, 125, 127, 129, 150, 165, 169, 198, 211, 275, 282, 286, 301, 330, 339, 387, 395, 400, 426, 450, 452, 479, 481, 508, 590, 596, 643, 662, 671, 705, 711, 718 of the application in sequence, and the other steps were the same as those of Comparative Example 1.

[0342] The test software, computer, K2400 digital source meter produced by Keithley Company of USA and PR788 spectral scanning luminance meter of PhotoResearch Company of USA are combined into an integrated IVL test system to test the luminous efficiency of the organic light-emitting device. The life test adopts M6000 OLED life test system of McScience Company. The test environment is atmospheric environment, and the temperature is room temperature. The obtained test results of the luminous characteristics of the organic light-emitting device are shown in Table 1. Table 1 is the test results of the luminous characteristics of the organic light-emitting device prepared by the compound of the embodiment of the present application and the comparative material.

[0343] [Table 1] Test results of luminous characteristics of organic light-emitting device

[0344]

[0345]

[0346] Note: T95 refers to the time taken for the luminance of the device to decay to 95% under the condition that the current density is 10 mA / cm 2 ; and

[0347] It can be seen from the results in Table 1 that the heterocycle-containing arylamine compound of the present application applied to the organic light-emitting device as a hole transport layer material can significantly improve the performance of the device compared with Comparative Examples 1-3. Compared with the 1, 3 or 2, 4 positions of the dibenzofuran / dibenzothiophene group, the steric hindrance of the 1, 4 position is smaller, which is conducive to the film formation of the molecule, and thus the compound has better hole transport capacity. Moreover, the present application introduces deuterium atoms on the amine group, and the compound has better thermal stability, and exhibits the advantages of high luminous efficiency and long service life.

[0348] Red organic light-emitting device (light-emitting auxiliary layer)

[0349] [Comparative Examples 4-5] Device preparation examples:

[0350] Comparative Example 4: The organic light-emitting device is prepared by a vacuum thermal evaporation method. The experimental steps are as follows: the ITO substrate is cleaned in distilled water for 3 times, ultrasonic washing for 15 minutes, after the distilled water cleaning, the solvents such as isopropanol, acetone and methanol are sequentially ultrasonically washed, and then dried at 120°C and sent to the evaporation machine.

[0351] A hole injection layer HATCN / 42 nm, a hole transport layer TAPC / 45 nm, a light emitting auxiliary layer HT-1 / 15 nm, a host m-CBP: doped RD (mass ratio 96%:4% mixture) / 19 nm, and then an electron transport layer ETL and Liq (doping ratio of mass ratio 1:1) / 29 nm, an electron injection layer LiF / 0.8 nm, and a cathode Al / 123 nm were vacuum evaporated on the prepared ITO transparent electrode in a layer-by-layer manner. The device was sealed in a glove box to prepare an organic light emitting device. After the preparation of the organic light emitting device was completed according to the above steps, the photoelectric performance of the device was measured, and the molecular structure of the related material is shown below:

[0352]

[0353] Comparative Example 5: The light emitting auxiliary layer material HT-1 in Comparative Example 4 was replaced by HT-2, and the organic light emitting device of Comparative Example 5 was manufactured in the same manner as Comparative Example 4.

[0354] [Application Examples 41-70]

[0355] Application Examples 41-70: The light emitting auxiliary layer material HT-1 of the organic light emitting device was replaced by the compounds 10, 19, 30, 41, 50, 66, 78, 85, 115, 125, 127, 129, 150, 165, 169, 198, 282, 286, 301, 330, 339, 387, 395, 400, 479, 481, 508, 662, 671, 711 of the application in turn, and the other steps were the same as those of Comparative Example 4. The test results of the light emitting characteristics of the obtained organic light emitting device are shown in Table 2. Table 2 shows the test results of the light emitting characteristics of the light emitting devices prepared by the compounds of the application and the comparative substances.

[0356] [Table 2] Test of light emitting characteristics of light emitting devices

[0357]

[0358]

[0359] Note: T95 refers to the time taken for the device brightness to decay to 95% under a current density of 10 mA / cm 2 ; and

[0360] As can be seen from the results in Table 2, the heterocycle-containing arylamine compound of the application applied to the organic light emitting device as a light emitting auxiliary layer material can significantly improve the performance of the device compared with Comparative Examples 4-5, and exhibits the advantages of high light emitting efficiency and long service life.

[0361] Blue organic light emitting device (cover layer)

[0362] [Comparative examples 6-7] Device preparation examples:

[0363] Comparative example 6: Organic light emitting device was prepared by vacuum thermal evaporation method. The experimental steps were as follows: ITO-Ag-ITO substrate was cleaned in distilled water for 3 times, ultrasonic washing for 15 minutes, after distilled water cleaning, isopropyl alcohol, acetone, methanol and other solvents were sequentially ultrasonic washed, and then dried at 120℃, and sent to the evaporation machine.

[0364] Hole injection layer HATCN / 43nm, hole transport layer NPB / 70nm, light emitting layer (host BH: doped BD (mass ratio 98%:2% mixture)) / 20nm, then electron transport layer ETL: Liq (doping ratio is mass ratio 1:1) / 30nm, electron injection layer LiF / 1nm, cathode Mg-Ag (mass ratio 1:9) / 18nm, and cover layer CP-1 / 72nm were evaporated on the prepared ITO-Ag-ITO transparent electrode in a layer-by-layer vacuum evaporation manner. The device was sealed in a glove box, thereby preparing an organic light emitting device. After the preparation of the organic light emitting device was completed according to the above steps, the photoelectric performance of the device was measured, and the molecular structure of the related material was as follows:

[0365]

[0366] Comparative example 7: The cover layer material CP-1 in comparative example 6 was replaced by CP-2, and the organic light emitting device of comparative example 7 was manufactured in the same way as comparative example 6.

[0367] [Application examples 71-84]

[0368] Application examples 71-84: The cover layer material CP-1 of the organic light emitting device was replaced by the compounds 19, 41, 66, 78, 150, 169, 275, 301, 330, 339, 452, 481, 508, 643 of the application in turn, and other steps were the same as comparative example 6. The test results of the light emitting characteristics of the obtained organic light emitting device are shown in Table 3. Table 3 is the test results of the light emitting characteristics of the organic light emitting devices prepared by the compounds of the application examples and comparative substances.

[0369] [Table 3] Test of light emitting characteristics of light emitting device

[0370]

[0371]

[0372] Note: T90 refers to the time taken for the device brightness to decay to 90% of the initial brightness at a current density of 10 mA / cm 2 in the case of a current density of 10 mA / cm

[0373] As can be seen from the results in Table 3, the heterocycle-containing arylamine compound of the present application applied to the organic light-emitting device as a cover layer material can effectively improve light extraction efficiency, and further improve the light-emitting efficiency of the organic light-emitting device, compared with Comparative Examples 6-7, and is a good organic light-emitting device cover layer material.

[0374] Green organic light-emitting device (host material)

[0375] [Comparative Examples 8-9] Device preparation examples:

[0376] Comparative Example 8: An organic light-emitting device was prepared by a vacuum thermal evaporation method. The experimental steps were as follows: the ITO substrate was cleaned in distilled water for 3 times, ultrasonic washing for 15 minutes, after the distilled water cleaning, the solvents such as isopropanol, acetone, and methanol were sequentially ultrasonic washed, and then dried at 120°C, and sent to the evaporation machine.

[0377] A hole injection layer HATCN / 41 nm, a hole transport layer NPB / 70 nm, a host GH-1: doped Ir(ppy)2acac (mass ratio 93:7 mixed) / 21 nm, and then an electron transport layer ETL and Liq (doping ratio mass ratio 1:1) / 32 nm, an electron injection layer LiF / 0.8 nm, and a cathode Al / 121 nm were evaporated on the prepared ITO transparent electrode in a layer-by-layer vacuum evaporation manner. The device was sealed in a glove box, thereby preparing an organic light-emitting device. After the preparation of the organic light-emitting device was completed according to the above steps, the photoelectric performance of the device was measured, and the molecular structure of the related material is shown as follows:

[0378]

[0379] Comparative Example 9: The host material GH-1 in Comparative Example 8 was replaced by GH-2, and the organic light-emitting device of Comparative Example 9 was manufactured in the same manner as Comparative Example 8.

[0380] [Application Examples 85-101]

[0381] Application Examples 85-101: The host material GH-1 of the organic light-emitting device was replaced with the compounds 10, 19, 30, 41, 50, 66, 78, 115, 125, 127, 169, 330, 450, 452, 479, 508, 596 of the present application, respectively, and the other steps were the same as those of Comparative Example 8. The results of the luminescent property test of the obtained organic light-emitting device are shown in Table 4. Table 4 shows the results of the luminescent property test of the organic light-emitting device prepared using the compound of the present application and the comparative material.

[0382] [Table 4] Luminescent property test of the organic light-emitting device

[0383]

[0384] As can be seen from the results of Table 4, the heterocycle-containing arylamine compound of the present application applied to the organic light-emitting device as the host material has improved luminous efficiency and prolonged service life as compared with Comparative Examples 8-9, and is a good organic light-emitting device host material.

[0385] It should be noted that the present application is particularly described with individual embodiments, but those skilled in the art can make various forms or details of improvement to the present application without departing from the principles of the present application, and these improvements also fall within the scope of protection of the present application.

Claims

1. A heterocyclic-containing arylamine compound, characterized by, The molecular structure is shown as Formula I: The X0 is selected from O or S; The Ar1, Ar3, Ar5 are the same as or different from each other, and are independently selected from one of the following groups: The Ar2, Ar4, Ar6 are the same as or different from each other, and are independently selected from one of the following groups: The R1 is selected from methyl, ethyl, propyl, butyl, adamantyl; said R 1a selected from phenyl; said R 1b selected from hydrogen; The R2, R3, R6 are selected from hydrogen; said n2 is selected from 0, 1, 2, 3 or 4; said n3 is selected from 0, 1, 2 or 3; said n 3a selected from 1 ; said n4 is selected from 1 ; said n6 is selected from 0, 1, 2, 3, 4, 5 or 6; said R a , R b are selected from one another identically from hydrogen; The a is selected from 0, 1 or 2; the b is selected from 0, 1, 2 or 3; The L1, L2, L3, L4, L5, L6 are independently selected from a single bond or one of the following groups: said L a is selected from a single bond or one of the following groups: said L b , L c is selected from a single bond; At least one of the Ar1, Ar3, Ar5 contains a deuterated group.

2. The heterocyclic-containing arylamine compound according to claim 1, characterized by At least two of the Ar1, Ar3, Ar5 contain deuterated groups.

3. The heterocyclic-containing arylamine compound according to claim 1, wherein The Ar2, Ar4, Ar6 are the same as or different from each other, and are independently selected from one of the following groups:

4. The heterocyclic-containing arylamine compound according to claim 1, wherein The L1, L2, L3, L4, L5, L6 are independently selected from a single bond.

5. A heterocyclic-containing arylamine compound characterized in that, The heterocycle-containing arylamine compound is selected from any one of the following chemical structures:

6. An organic light emitting device comprising an anode, a cathode, an organic layer, said organic layer being located between said anode and said cathode or outside one or more of said anode and said cathode, characterized in that, The organic layer contains any one of the heterocycle-containing arylamine compounds or a combination of at least two of the heterocycle-containing arylamine compounds according to any one of claims 1-5.

7. An organic light emitting device according to claim 6, said organic layer being disposed between said anode and said cathode, said organic layer comprising a hole transport region, a light emitting region, and an electron transport region, characterized in that, The hole transport region and / or the light emitting layer contains any one of the heterocycle-containing arylamine compounds or a combination of at least two of the heterocycle-containing arylamine compounds according to any one of claims 1-5.

8. The organic light emitting device according to claim 6, wherein the organic layer is located outside of either of the anode and the cathode. The organic layer contains any one of the heterocycle-containing arylamine compounds or a combination of at least two of the heterocycle-containing arylamine compounds according to any one of claims 1-5.

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