Triarylamine compound and organic light-emitting device thereof

Abstract

The invention provides a triarylamine compound and an organic light-emitting device thereof, and relates to the technical field of organic photoelectric materials. According to the compound, triarylamine serves as the center and is connected with a benzofuran / thiophene group and a fluorene group, and a large-steric-hindrance naphthenic base group is fused on fluorene, so that planar triarylamine is not prone to stacking, fused naphthenic base has an electron-rich effect, hole mobility can be effectively improved, excellent hole transport performance is achieved, and the compound can be applied to the field of organic electroluminescent devices. The luminous efficiency of the device can be greatly improved; in addition, the intermolecular force of the compound is small, the crystallinity of molecules can be reduced, the film-forming property of the material is improved, and the service life of the organic light-emitting device is further prolonged. Meanwhile, when the compound is applied to the organic light-emitting device as a covering layer material, the light-emitting efficiency of the device can be improved, and the service life of the device can be prolonged. The compound can be widely applied to the fields of organic photovoltaic devices, organic light-emitting devices, organic solar cells, electronic paper, organic photoreceptors, organic thin film transistors and the like.

Description

Technical Field

[0001] The invention relates to the technical field of organic photoelectric materials, and in particular to a triarylamine compound and an organic light-emitting device thereof. Background Art

[0002] In recent years, organic light-emitting devices that can be driven at low voltage in a self-luminous manner have excellent viewing angles and contrast ratios compared to liquid crystal displays (LCDs), which are the mainstream flat panel display devices. They do not require backlight sources, so they can be made lighter and thinner, and are also advantageous in terms of power consumption. They also have a wide range of color reproduction, and are therefore attracting much attention as next-generation display devices.

[0003] Organic light-emitting devices mainly adopt a "sandwich" layered structure. According to the light emission path, organic light-emitting devices can be divided into: bottom-emitting organic light-emitting devices and top-emitting organic light-emitting devices. Among them, bottom-emitting organic light-emitting devices mainly include light-transmitting anodes, carrier (holes and electrons) injection layers, carrier (holes and electrons) transport layers, light-emitting layers, and cathodes; top-emitting organic light-emitting devices mainly include opaque anodes, carrier (holes and electrons) injection layers, carrier (holes and electrons) transport layers, light-emitting layers, light-transmitting cathodes, covering layers, etc. The structure and selected materials of organic light-emitting devices directly determine the luminous efficiency and service life of the devices.

[0004] There are many compounds used in organic light-emitting devices at present, but in the case of organic light-emitting devices using well-known substances, it is difficult to put them into practical use due to high driving voltage, low efficiency and short life. As for the substances used in the hole transport layer, since they need to have a low HOMO value, most materials have a low T1 value, so the excitons generated in the light-emitting layer will move to the hole transport layer, which will eventually lead to the imbalance of the charge balance in the light-emitting layer, and the problem of luminescence will occur at the interface of the hole transport layer, resulting in reduced color purity, reduced efficiency, shortened life and other problems. Therefore, in order to improve the luminous efficiency of the device and extend the service life of the device, the development of hole transport materials with good hole transport speed and good thermal stability, as well as covering layer materials with high refractive index, no absorption in the visible light band, resistance to UV damage, and good film stability has become the focus of research in the field of organic light-emitting devices. Summary of the invention

[0005] The purpose of the present invention is to provide a triarylamine compound and an organic light-emitting device thereof based on the prior art and with industrialization as the goal. The organic light-emitting device prepared using the triarylamine compound has the characteristics of high luminous efficiency and long life. The general molecular structure is shown in Formula I:

[0006]

[0007] Wherein, the ring A is selected from one of the groups represented by formula a, formula b, and formula c:

[0008]

[0009] The R m , R n Independently selected from any one of hydrogen, deuterium, C1-C6 alkyl, C3-C15 cycloalkyl, C6-C25 aryl; m is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; "*" is the connection site;

[0010] The X is selected from O, S or NR c , wherein R c is selected from a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C25 aryl group, a substituted or unsubstituted fused ring group of a C6-C30 aromatic ring and a C3-C30 aliphatic ring, a substituted or unsubstituted C2-C25 heteroaryl group, or R c The corresponding nitrogen atom is the site of connection with the bridge L2;

[0011] The ring B is selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, a substituted or unsubstituted triazine ring, a substituted or unsubstituted pyrazine ring, a substituted or unsubstituted pyridazine ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted quinazoline ring, a substituted or unsubstituted quinoxaline ring, a substituted or unsubstituted azaphenanthren ring, and a substituted or unsubstituted azaanthracene ring;

[0012] The R e are the same as or different from each other and are selected from one of hydrogen, deuterium, halogen atoms, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C25 heteroaryl; said e is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

[0013] Ar1 is selected from a substituted or unsubstituted C8-C25 fused aromatic group, a substituted or unsubstituted C6-C30 fused aromatic ring and a C3-C30 aliphatic ring, and a substituted or unsubstituted C2-C25 fused heteroaromatic group;

[0014] The L1, L2, and L3 are independently selected from a single bond, a substituted or unsubstituted C6-C25 arylene group, a substituted or unsubstituted C3-C10 aliphatic ring and a C6-C25 aromatic ring sub-condensed ring group, and a substituted or unsubstituted C2-C20 heteroarylene group;

[0015] The R1 and R2 are the same as or different from each other, and are independently selected from one of hydrogen, deuterium, halogen atoms, cyano groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 cycloalkyl groups, substituted or unsubstituted C2-C30 alkenyl groups, substituted or unsubstituted C6-C25 aryl groups, substituted or unsubstituted C6-C30 aromatic rings and C3-C30 aliphatic rings fused ring groups, substituted or unsubstituted C2-C25 heteroaryl groups, or adjacent R1 and adjacent R2 may be connected to form a ring structure;

[0016] The a is selected from 0, 1, 2, 3 or 4; the b is selected from 0, 1, 2 or 3.

[0017] The present invention 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 electrodes of the anode and the cathode, and the organic layer contains any one or a combination of at least two of the triarylamine compounds described in the present invention.

[0018] Beneficial effects of the present invention:

[0019] The present invention provides a triarylamine compound and an organic light-emitting device thereof. The compound of the present invention is centered on triarylamine, connecting a benzofuran / thiophene group and a fluorene group, and a large sterically hindered cycloalkyl group is fused on the fluorene, so that the planar triarylamine is not easy to stack, and the fused cycloalkyl has an electron-rich effect, which can effectively improve the hole mobility, has excellent hole transport performance, and can greatly improve the luminous efficiency of the device; in addition, the intermolecular force of the compound of the present invention is small, which can reduce the crystallinity of the molecule, improve the film-forming property of the material, and thus improve the life of the organic light-emitting device. At the same time, the compound of the present invention is applied to an organic light-emitting device as a covering layer material, which can effectively reduce the total reflection loss and waveguide loss in the OLED device, improve the light extraction efficiency, and thus improve the luminous efficiency of the device. In addition, the compound of the present invention has good physical and thermal stability, and can extend the service life of the device. DETAILED DESCRIPTION

[0020] The following will be described clearly and completely in conjunction with the technical solutions of the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present invention.

[0021] In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes the atom in both its natural isotopic abundance and unnatural abundance.

[0022] In the present invention, the use of "H" and "hydrogen" means that the hydrogen atoms in the chemical structure contain no more than the natural abundance of deuterium atoms or tritium atoms, for example, no more than 0.0156 atomic % of deuterium. "D" and "deuterium" mean that the abundance of deuterium content is above the natural abundance, for example, any value exceeding 0.1 atomic %, exceeding 1 atomic %, exceeding 10 atomic %, for example, about 95 atomic % of which is deuterium. In the present invention, the omitted hydrogen atoms represent "H" or "hydrogen".

[0023] 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 of the corresponding optional positions of the ring.

[0024] For example, Can be expressed Can be expressed Can be expressed And so on.

[0025] In this specification, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically, it can be connected to any of the corresponding optional sites of the ring. For example, Can be expressed Can be expressed Can be expressed And so on.

[0026] The halogen mentioned in the present invention refers to fluorine, chlorine, bromine and iodine.

[0027] The silyl group in the present invention refers to a silicon hydrocarbon group formed by removing a hydrogen atom from a silane hydrocarbon molecule. The present invention preferably uses a silyl group, which has -Si(R k )3, R kAny one selected from H, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C2-C30 heteroaryl, but not limited thereto. Substituted silyl groups specifically include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but not limited thereto. The above-mentioned silyl groups are preferably trimethylsilyl, triethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl.

[0028] The alkyl group described in the present invention refers to a hydrocarbon group formed by missing a hydrogen atom in an alkane molecule, which can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but not limited thereto; the branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomeric groups of n-pentyl, isomeric groups of n-hexyl, isomeric groups of n-heptyl, isomeric groups of n-octyl, isomeric groups of n-nonyl, isomeric groups of n-decyl, etc., but not limited thereto. The above-mentioned alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.

[0029] The chain alkyl group with more than three carbon atoms described in the present invention includes its isomers, for example, propyl group includes n-propyl group and isopropyl group, butyl group includes n-butyl group, sec-butyl group, isobutyl group and tert-butyl group, and so on.

[0030] The cycloalkyl group of the present invention refers to a hydrocarbon group formed by removing a hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms, and examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, bornyl, norbornyl, etc., but are not limited thereto. The above cycloalkyl group is preferably cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, norbornyl.

[0031] Alkenyl of the present invention refers to a monovalent group obtained by removing a hydrogen atom from an olefin molecule, and the alkenyl includes monoalkenyl, dienyl, polyalkenyl, etc. Preferably, it has 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 6 carbon atoms. Examples of the alkenyl include vinyl, vinyl, 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 is preferably vinyl.

[0032] The alkenyl group with more than three carbon atoms described in the present invention includes isomers thereof, 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.

[0033] The aryl group described in the present invention refers to a general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic compound molecule, which can be a monocyclic aryl group, a polycyclic aryl group or a condensed aryl group, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group having only one aromatic ring in the molecule, such as phenyl, etc., but not limited thereto; the polycyclic aryl group refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited thereto; the condensed aryl group refers to an aryl group containing two or more aromatic rings in the molecule and fused to each other by sharing two adjacent carbon atoms, such as naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylene, fluoranthenyl, spirobifluorenyl, etc., but not limited thereto. The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group (preferably a 2-naphthyl group), an anthracenyl group (preferably a 2-anthryl group), a phenanthrenyl group, a pyrenyl group, a perylenyl group, a fluorenyl group, a benzofluorenyl group, a triphenylene group, or a spirobifluorenyl group.

[0034] The heteroaryl group described in the present invention refers to a general term for a group in which one or more aromatic carbon atoms in the aromatic group are replaced by heteroatoms, wherein the heteroatoms include but are 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, and most preferably 3 to 12 carbon atoms. The attachment site of the heteroaryl group may be located on a ring-forming carbon atom or a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a condensed-ring heteroaryl group. The monocyclic heteroaryl groups include pyridyl, pyrimidinyl, triazine, furanyl, thienyl, pyrrolyl, imidazolyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include bipyridyl, bipyrimidinyl, phenylpyridyl, etc., but are not limited thereto; the condensed ring heteroaryl groups include quinolyl, isoquinolyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, etc., but are not limited thereto. The above-mentioned heteroaryl group is preferably pyridyl, pyrimidinyl, thienyl, furyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, benzodibenzothienyl, benzodibenzofuranyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, and phenoxathiyl.

[0035] The arylene group described in the present invention refers to the general term for the divalent group left after two hydrogen atoms are removed from the aromatic core carbon of the aromatic compound molecule, which can be a monocyclic arylene group, a polycyclic arylene group or a condensed ring arylene group, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic arylene group includes phenylene, etc., but is not limited thereto; the polycyclic arylene group includes biphenylene, terphenylene, etc., but is not limited thereto; the condensed ring arylene group includes naphthylene, anthrylene, phenanthrenyl, fluorenylene, pyrenylene, triphenylene, fluoranthenylene, phenylenefluorenyl, etc., but is not limited thereto. The above-mentioned arylene group is preferably phenylene, biphenylene, terphenylene, naphthylene, fluorenylene, phenylenefluorenyl, etc.

[0036] The sub-condensed cyclic group of the aliphatic ring and the aromatic ring of the present invention refers to the general term for the divalent group left after the aliphatic ring and the aromatic ring are condensed together and two hydrogen atoms are removed. It preferably has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 12 carbon atoms. Examples may include benzocyclopropylene, benzocyclobutylene, benzocyclopentylene, benzocyclohexylene, benzocycloheptylene, benzocyclopentenylene, benzocyclohexenylene, naphthocyclopropylene, naphthocyclobutylene, naphthocyclopentylene, naphthocyclohexylene, but are not limited thereto.

[0037] The fused ring of an aromatic ring and an aliphatic ring described in the present invention refers to a ring containing one or more aromatic rings and one or more aliphatic rings fused to each other by sharing two adjacent carbon atoms in the molecule. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The aliphatic ring preferably 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 benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthylcyclopropanyl, naphthylcyclobutanyl, naphthylcyclopentanyl, naphthylcyclohexanyl, naphthylcyclopentenyl, naphthylcyclohexenyl, etc., but are not limited thereto.

[0038] The aliphatic ring described in the present invention refers to a cyclic hydrocarbon with aliphatic properties, containing a closed carbon ring in the molecule, preferably having 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 monocyclic hydrocarbon or a polycyclic hydrocarbon, which can be completely unsaturated or partially unsaturated. Specific examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited thereto. Multiple monocyclic hydrocarbons can also be connected in a variety of ways: two rings in the molecule can share a carbon atom to form a spirocycle; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings can also be connected to each other to form a cage structure.

[0039] The heteroarylene group of the present invention refers to a general term for a group obtained by replacing one or more aromatic carbon atoms in an arylene group with a heteroatom, wherein the heteroatom includes but is not limited to an oxygen, sulfur, nitrogen or phosphorus atom. It preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The attachment site of the heteroarylene group may be located on a ring-forming carbon atom or a ring-forming nitrogen atom. The heteroarylene group may be a monocyclic heteroarylene group, a polycyclic heteroarylene group or a condensed ring heteroarylene group. The monocyclic heteroaryl groups include pyridylene, pyrimidylene, triazineylene, furanylene, thienylene, etc., but are not limited thereto; the polycyclic heteroaryl groups include bipyridylene, bipyrimidylene, phenylpyridylene, etc., but are not limited thereto; the condensed-ring heteroaryl groups include quinolylene, isoquinolylene, indolylene, benzothienylene, benzofuranylene, benzoxazolylene, benzimidazolylene, benzothiazolylene, dibenzofuranylene, benzofuranylene, dibenzothienylene, benzothienylene, carbazolylene, benzocarbazolylene, acridinylene, phenoxazinylene, phenothiazinylene, phenoxathiylene, etc., but are not limited thereto. The above heteroaryl group is preferably a pyridylene group, a pyrimidylene group, a thienylene group, a furylene group, a benzothienylene group, a benzofuranylene group, a benzoxazolylene group, a benzimidazolyl group, a benzothiazolylene group, a dibenzofuranyl group, a dibenzothienylene group, a carbazolylene group, a benzofuranyl group, a benzothienylene group, or an acridinylene group.

[0040] The term "substituted..." as used herein, such as substituted silyl, substituted alkyl, substituted cycloalkyl, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted aromatic ring and aliphatic ring fused ring, substituted arylene, substituted aliphatic ring and aromatic ring fused ring, substituted heteroarylene, etc., refers to a group independently selected from, but not limited to, deuterated, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C15 heteroaryl, substituted or unsubstituted amino, etc., which is mono- or poly-substituted. The substituted groups are preferably monosubstituted or polysubstituted by a group selected from deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, peryl, pyrenyl, benzyl, tolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, diphenylamino, dimethylamino, carbazolyl, 9-phenylcarbazolyl, acridinyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, phenothiazinyl, phenoxazinyl, indolyl. In addition, the above substituents may be substituted by one or more substituents selected from deuterium, halogen atoms, cyano, alkyl, cycloalkyl, silyl, and aryl.

[0041] Unless otherwise specified, the term "ring" used herein refers to a condensed ring consisting of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, or a heterocyclic ring having 2 to 60 carbon atoms, or a combination thereof, which includes a saturated or unsaturated ring.

[0042] The bonding to form a ring structure in the present invention means that two groups are connected to each other by a chemical bond and are optionally aromatized. For example:

[0043]

[0044] In the present invention, the ring formed by connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring or a condensed ring, such as benzene, naphthalene, fluorene, cyclopropane, cyclobutane, cyclopentene, cyclopentane, cyclohexene, cyclohexane, cyclopentane acene, cyclohexane acene, quinoline, isoquinoline, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.

[0045] In the present invention, the term "at least one" means, under permitted conditions, one, two, three, four, five, six or more. In the present invention, the term "one or more" means, under permitted conditions, one, two, three, four, five, six or more.

[0046] The present invention provides a triarylamine compound, the molecular structure of which is shown in Formula I:

[0047]

[0048] Wherein, the ring A is selected from one of the groups represented by formula a, formula b, and formula c:

[0049]

[0050] The R m , R n Independently selected from any one of hydrogen, deuterium, C1-C6 alkyl, C3-C15 cycloalkyl, C6-C25 aryl; m is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; "*" is the connection site;

[0051] The X is selected from O, S or NR c , wherein R c is selected from a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C25 aryl group, a substituted or unsubstituted fused ring group of a C6-C30 aromatic ring and a C3-C30 aliphatic ring, a substituted or unsubstituted C2-C25 heteroaryl group, or R cThe corresponding nitrogen atom is the site of connection with the bridge L2;

[0052] The ring B is selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, a substituted or unsubstituted triazine ring, a substituted or unsubstituted pyrazine ring, a substituted or unsubstituted pyridazine ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted quinazoline ring, a substituted or unsubstituted quinoxaline ring, a substituted or unsubstituted azaphenanthren ring, and a substituted or unsubstituted azaanthracene ring;

[0053] The R e are the same as or different from each other and are selected from one of hydrogen, deuterium, halogen atoms, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C25 heteroaryl; said e is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

[0054] Ar1 is selected from a substituted or unsubstituted C8-C25 fused aromatic group, a substituted or unsubstituted C6-C30 fused aromatic ring and a C3-C30 aliphatic ring, and a substituted or unsubstituted C2-C25 fused heteroaromatic group;

[0055] The L1, L2, and L3 are independently selected from a single bond, a substituted or unsubstituted C6-C25 arylene group, a substituted or unsubstituted C3-C10 aliphatic ring and a C6-C25 aromatic ring sub-condensed ring group, and a substituted or unsubstituted C2-C20 heteroarylene group;

[0056] The R1 and R2 are the same as or different from each other, and are independently selected from one of hydrogen, deuterium, halogen atoms, cyano groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 cycloalkyl groups, substituted or unsubstituted C2-C30 alkenyl groups, substituted or unsubstituted C6-C25 aryl groups, substituted or unsubstituted C6-C30 aromatic rings and C3-C30 aliphatic rings fused ring groups, substituted or unsubstituted C2-C25 heteroaryl groups, or adjacent R1 and adjacent R2 may be connected to form a ring structure;

[0057] The a is selected from 0, 1, 2, 3 or 4; the b is selected from 0, 1, 2 or 3.

[0058] Preferably, the formula a is selected from one of the following groups:

[0059]

[0060] The formula b is selected from one of the following groups:

[0061]

[0062] The formula C is selected from one of the following groups:

[0063]

[0064] Preferably, the Any one selected from the following groups:

[0065]

[0066] The X is selected from O, S or NR c , wherein R c R is selected from hydrogen, deuterium, trifluoromethyl, a substituted or unsubstituted one of the following groups: trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, indanyl, indenyl, benzocyclobutyl, benzocyclopropyl, or R c The corresponding nitrogen atom is the site of connection with the bridge L2;

[0067] The R e are the same as or different from each other and are selected from one of hydrogen, deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, trideuterophenylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, bornyl, indanyl, indenyl, benzocyclobutyl, benzocyclobutenyl, benzocyclopropyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, anthracenyl, phenanthryl, triphenylene, deuterated phenyl, deuterated naphthyl and deuterated biphenyl; wherein R e It can also be R ee Replaced by R eeOne or more selected from hydrogen, deuterium, trimethylsilyl, triphenylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, tolyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, anthracenyl, phenanthryl; when substituted by multiple substituents, the multiple substituents are the same or different from each other;

[0068] The e1 is selected from 0 or 1; the e2 is selected from 0, 1 or 2; the e3 is selected from 0, 1, 2 or 3; the e4 is selected from 0, 1, 2, 3 or 4; the e5 is selected from 0, 1, 2, 3, 4 or 5; the e6 is selected from 0, 1, 2, 3, 4, 5 or 6; the e7 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the e8 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the e9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0069] Preferably, Ar1 is selected from any one of the following groups:

[0070]

[0071] wherein the ring C is selected from a substituted or unsubstituted three-membered, four-membered, five-membered, six-membered, seven-membered or eight-membered saturated or unsaturated aliphatic ring; the ring D is selected from a substituted or unsubstituted benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a triazine ring, a pyrazine ring, a pyridazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, an azaphenanthren ring, and an azaanthracene ring;

[0072] X1 is selected from O, S or NR s , wherein R s One selected from hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C25 heteroaryl;

[0073] Said X2 is selected from O or S;

[0074] The X3 is selected from CR7R8, O, S or NR9, wherein the R7 and R8 are independently selected from one of substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, and substituted or unsubstituted C6-C25 aryl; the R9 is selected from one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C25 heteroaryl;

[0075] The R3 is selected from hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C3-C60 heteroaryl; or the nitrogen atom corresponding to R3 is the site of connection with the bridge L1;

[0076] The R4 and R5 are independently selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C25 heteroaryl, or adjacent R4 and R5 can be connected to form a ring structure;

[0077] The R h , R k are the same as or different from each other and are each independently selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C25 heteroaryl, or adjacent R h Can be connected into a ring structure;

[0078] The h1 is selected from 0, 1, 2 or 3; the h2 is selected from 0, 1, 2, 3 or 4; the h5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the h7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the k is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.

[0079] Further preferably, the Ar1 is selected from any one of the following groups:

[0080]

[0081]

[0082]

[0083] The R h are the same as or different from each other and are selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, a substituted or unsubstituted one of the following groups: trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, indenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, wherein R k the same as or different from each other, and are selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one of the following groups: trimethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, indenyl, pyridyl, pyrimidyl , pyridazinyl, pyrazinyl, wherein the "substituted or unsubstituted" substituent is selected from one or more of hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, camphenyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl;

[0084] h0 is selected from 0, 1 or 2; h1 is selected from 0, 1, 2 or 3; h2 is selected from 0, 1, 2, 3 or 4; h3 is selected from 0, 1, 2, 3, 4 or 5; h4 is selected from 0, 1, 2, 3, 4, 5 or 6; h5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; h6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; h7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; h8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; h9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; 10 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; said h 12 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14;

[0085] The k1 is selected from 0, 1 or 2; the k2 is selected from 0, 1, 2, 3 or 4; the k3 is selected from 0, 1, 2, 3, 4, 5 or 6; the k4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the k5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0086] Preferably, R3 and R6 are independently selected from hydrogen, deuterium, or one of the following substituted or unsubstituted groups: trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazolyl, tetrakis The “substituted or unsubstituted” substituent is selected from one of hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, camphenyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl and one or more thereof. When substituted by multiple substituents, the multiple substituents are the same or different from each other.

[0087] Preferably, L1, L2, and L3 are independently selected from a single bond, a group as shown below, and a combination thereof:

[0088]

[0089] The R r are the same as or different from each other and are selected from any one of hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, and a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring;

[0090] The r0 is selected from 0, 1 or 2; the r1 is selected from 0, 1, 2, 3 or 4; the r2 is selected from 0, 1, 2, 3, 4, 5 or 6; the r3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the r4 is selected from 0, 1, 2 or 3;

[0091] The R x , R y Independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl or substituted or unsubstituted groups: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothienyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazolyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, indenyl.

[0092] Further preferably, the R r The same or different substituents are selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted one or more of the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, indenyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl. When substituted by multiple substituents, the multiple substituents are the same or different from each other.

[0093] Most preferably, L1, L2, L3 are independently selected from a single bond or one of the following groups:

[0094]

[0095] Most preferably, the triarylamine compound is selected from any one of the chemical structures shown below:

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120] The present invention 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 electrodes of the anode and the cathode, and the organic layer contains any one or a combination of at least two of the triarylamine compounds described in the present invention.

[0121] Preferably, the organic layer comprises an organic layer in a hole transport region, and at least one layer in the hole transport region contains any one or a combination of at least two of the triarylamine compounds described in the present invention.

[0122] Preferably, the hole transport region comprises a hole injection layer, a hole transport layer and an electron blocking layer, and the hole transport layer contains any one or a combination of at least two of the triarylamine compounds described in the present invention.

[0123] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and the first hole transport layer and / or the second hole transport layer contains any one or a combination of at least two of the triarylamine compounds described in the present invention.

[0124] Preferably, the organic layer is located between the anode and the cathode, the organic layer comprises a first light-emitting portion, a second light-emitting portion and a charge generating layer, the first light-emitting portion is located between the anode and the cathode, the second light-emitting portion is located between the first light-emitting portion and the cathode, the charge generating layer is located between the first light-emitting portion and the second light-emitting portion, and the charge generating layer comprises at least one of the triarylamine compounds described in the present invention.

[0125] Preferably, the charge generation layer is composed of an N-type charge generation layer arranged adjacent to the first light-emitting portion and a P-type charge generation layer arranged adjacent to the second light-emitting portion, and the organic layer contains the P-type charge generation layer, and the P-type charge generation layer contains at least one of the triarylamine compounds described in the present invention.

[0126] Preferably, the organic layer is located outside one or more electrodes of the anode and the cathode, and the organic layer comprises a covering layer, and the covering layer contains any one or a combination of at least two of the triarylamine compounds described in the present invention.

[0127] The light emitting device of the present invention is usually formed on a substrate. The substrate may be any substrate as long as it does not change when forming the electrode or the organic layer, for example, a substrate of glass, plastic, polymer film, silicon, etc. When the substrate is opaque, the electrode opposite thereto is preferably transparent or translucent.

[0128] The anode material may be, for example, a material having a large work function so that holes can be smoothly injected into the organic layer. For example, it may be carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, etc. and alloys thereof, oxidized metals such as tin oxide and indium oxide used in ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole, etc., but is not limited thereto.

[0129] The cathode material may be, for example, a material having a small work function so that electrons are smoothly injected into the organic layer. The cathode material may be, for example, a metal or a multilayer structure material. Magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, etc. and alloys thereof may be used, but are not particularly limited thereto. Examples of the alloy include magnesium / silver, magnesium / indium, lithium / aluminum, etc. The cathode material is preferably selected from magnesium and silver, but is not limited thereto.

[0130] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a hole transport layer (HTL) of a single-layer structure, including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multi-layer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0131] In addition to the triarylamine compounds of the present invention, the materials of the hole transport region can be selected from small molecule materials such as aromatic amine derivatives, carbazole derivatives, stilbene derivatives, triphenyldiamine derivatives, styrene compounds, butadiene compounds, and polymer materials such as polyparaphenylene derivatives, polyaniline and its derivatives, polythiophene and its derivatives, polyvinylcarbazole and its derivatives, polysilane and its derivatives, but are not limited thereto. Preferably, the hole transport layer uses any one or a combination of at least two of the triarylamine compounds described in the present invention, which can be a single structure composed of a single substance, or a single-layer structure or a multi-layer structure formed by different substances. The materials of the hole transport region can include the first hole transport layer material and / or the second hole transport layer material.

[0132] The hole injection layer is a layer for injecting holes from the electrode, and metal porphyrin, oligothiophene, aromatic amine organic matter, hexanitrile hexaazatriphenylene organic matter, quinacridone organic matter, perylene organic matter, anthraquinone, polyaniline and polythiophene conductive polymers can be selected, but it is not limited to these.

[0133] The luminescent material of the luminescent layer is preferably a material with high quantum efficiency for fluorescence or phosphorescence, such as 8-hydroxyquinoline aluminum complex; carbazole compounds; diphenylethylene compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzoazole, benzothiazole and benzimidazole compounds; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0134] The light-emitting layer may include a host material and a dopant material. The host material includes an aromatic fused ring derivative or a heterocyclic compound. Specifically, as the aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as the heterocyclic compound, there are carbazole derivatives, dibenzofuran derivatives, etc., but it is not limited thereto.

[0135] The dopant material includes aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, as aromatic amine derivatives, there are aromatic condensed ring derivatives of substituted or unsubstituted arylamine groups, such as pyrene and anthracene of arylamine groups, and as styrylamine compounds, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0136] The light-emitting layer includes a light-emitting material that can emit light of different wavelength spectra, and may also include a host material. The light-emitting layer may be a monochromatic light-emitting layer that emits a single color such as red, green, and blue. Multiple monochromatic light-emitting layers of different colors may be arranged in a plane according to a pixel pattern, or may be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they may be separated from each other or may be connected to each other. The light-emitting layer may also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0137] According to different technologies, the light-emitting layer material can be made of different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescent materials. In an organic light-emitting device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

[0138] The optimal doping ratio of the main material and the guest material of the light-emitting layer may vary depending on the materials used. Usually, the doping mass percentage of the guest material of the light-emitting layer is 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

[0139] The electron transport region is located between the light-emitting layer and the cathode. The electron transport region can be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region can also be a multi-layer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0140] The electron transport layer may include a first electron transport layer material and a second electron transport layer material. Commonly used materials for electron transport materials are well-known triazine derivatives, oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethane and its derivatives, fluorenone derivatives, di-p-benzoquinone derivatives, 8-hydroxyquinoline and its derivatives of metal complexes, which may be a single structure composed of a single substance, or a single-layer structure or a multi-layer structure formed by different substances.

[0141] The electron injection layer is located between the electron transport layer and the cathode, and the electron injection layer may include alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof. Alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of alkali metals, alkaline earth metals, and rare earth metals. Alkali metals may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, or Cs. Alkali metal compounds may be selected from alkali metal oxides (e.g., Li2O, Cs2O, and / or K2O) and alkali metal halides (e.g., LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI). Alkaline earth metals may be selected from Mg, Ca, Sr, and Ba. Alkaline earth metal compounds may be selected from alkaline earth metal oxides (e.g., BaO, SrO, CaO). The rare earth metal may be selected from scandium (Sc), yttrium (Y), cerium (Ce), ytterbium (Yb) and gadolinium (Gd). The rare earth metal compound may be selected from YbF3, ScF3, Sc2O3, Y2O3 and TbF3. It may be a single structure composed of a single substance, or a single-layer structure or a multi-layer structure formed by different substances.

[0142] The covering layer material generally has a high refractive index, which can help improve the light efficiency of the organic light-emitting device, especially help improve the external light-emitting efficiency. Preferably, the covering layer material of the present invention is selected from any one or a combination of at least two of the triarylamine compounds of the present invention.

[0143] The thickness of the hole transport layer and the electron transport layer may vary depending on the material used, as long as the driving voltage and the luminous efficiency can be selected according to the conditions that can achieve appropriate values, but the thickness must at least not cause pinholes. If it is too thick, the driving voltage of the device will increase, which is not ideal. Therefore, the thickness of the hole transport layer and the electron transport layer is, for example, 1nm to 1um, preferably 2nm to 500nm, and more preferably 5nm to 200nm.

[0144] The organic light-emitting device of the present invention may be a top-emitting type, a bottom-emitting type or a bidirectional-emitting type. The preparation and formation methods of each layer in the organic light-emitting device are not particularly limited, and any of dry film-forming methods such as vacuum evaporation, sputtering, plasma, and ion plating, and wet film-forming methods such as spin coating, dip coating, and flow coating may be used. In the present invention, the vacuum evaporation method is preferably used. The compound used as the organic layer may be an organic small molecule, an organic macromolecule, a polymer, and a combination thereof.

[0145] The organic light-emitting device of the present invention can be widely used in the fields of organic photovoltaic devices, organic light-emitting devices, organic solar cells, electronic paper, organic photoreceptors, organic thin film transistors, etc.

[0146] The present invention also provides a preparation method of formula I, but the preparation method of the present invention is not limited thereto. The structure of formula I can be prepared by the following reaction route (1) or (2):

[0147]

[0148] The X1 and X2 are independently selected from any one of I, Br and Cl.

[0149] The present invention has no particular restrictions on the sources of the raw materials used in the above-mentioned various reactions, and commercially available raw materials or preparation methods well known to those skilled in the art can be used. The present invention has no particular restrictions on the above-mentioned reactions, and conventional reactions well known to those skilled in the art can be used. The compound synthesis steps of the present invention are few, the method is simple, and it is conducive to industrial production.

[0150] By the following examples, the present invention is explained in more detail, but it is not intended to limit the present invention. On the basis of this description, those of ordinary skill in the art will be able to implement the present invention and prepare other compounds and devices according to the present invention within the entire disclosed range without paying creative work.

[0151] Preparation and characterization of compounds

[0152] Description of raw materials, reagents and characterization equipment:

[0153] Mass spectrometry was performed using a British Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent;

[0154] The elemental analysis was performed using a Vario EL cube organic element analyzer from Elementar, Germany, with a sample mass of 5 to 10 mg.

[0155] Synthesis Example 1: Preparation of Compound 1

[0156]

[0157] Preparation of intermediate A-1:

[0158] Under nitrogen protection, toluene (400 ml), a-1 (20.09 g, 55.00 mmol), b-1 (11.51 g, 55.00 mmol), palladium acetate (0.25 g, 1.10 mmol), sodium tert-butoxide (10.57 g, 110.00 mmol) and tri-tert-butylphosphine (2.20 mL, 1.10 mmol, 0.50 M in toluene solution) were added to the reaction bottle in sequence, the mixture was stirred, and heated under reflux for 4.5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, extracted with dichloromethane, the organic phase was collected, dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The intermediate A-1 (21.18 g, 78%) was recrystallized with toluene: ethanol (9:1) to obtain the solid purity of ≥99.80% by HPLC. Mass spectrum m / z: 493.2417 (theoretical value 493.2406). Preparation of compound 1:

[0159] Under nitrogen protection, toluene (300 ml), intermediate A-1 (17.28 g, 35.00 mmol), c-1 (9.56 g, 35.00 mmol), Pd2(dba)3 (0.32 g, 0.35 mmol), sodium tert-butoxide (6.73 g, 70.00 mmol) and BINAP (0.44 g, 0.70 mmol) were added to the reaction bottle in sequence, the mixture was stirred, and heated to reflux for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, extracted with dichloromethane, the organic phase was collected, dried with anhydrous magnesium sulfate, filtered, the solvent was removed by vacuum distillation, and recrystallized with toluene to obtain compound 1 (18.00 g, yield 75%). The solid purity was ≥99.97% detected by HPLC. Mass spectrum m / z: 685.2966 (theoretical value: 685.2981). Theoretical element content (%) C 50 H 39 NO2: C, 87.56; H, 5.73; N, 2.04. Measured element content (%): C, 87.59; H, 5.70; N, 2.02.

[0160] Synthesis Example 2: Preparation of Compound 16

[0161]

[0162] According to the same preparation method of compound 1 in Synthesis Example 1, b-1 was replaced with an equal molar amount of b-16, and the other steps were the same to obtain compound 16 (17.05 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 695.3199 (theoretical value: 695.3188). Theoretical element content (%) C 52 H41 NO: C, 89.75; H, 5.94; N, 2.01. Measured element content (%): C, 89.78; H, 5.92; N, 2.00.

[0163] Synthesis Example 3: Preparation of Compound 21

[0164]

[0165] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 was replaced with an equal molar amount of b-21, and the other steps were the same to obtain compound 21 (16.45 g); HPLC purity ≥ 99.93%. Mass spectrum m / z: 745.3352 (theoretical value: 745.3345). Theoretical element content (%) C 56 H 43 NO: C, 90.17; H, 5.81; N, 1.88. Measured element content (%): C, 90.15; H, 5.84; N, 1.86.

[0166] Synthesis Example 4: Preparation of Compound 40

[0167]

[0168] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 was replaced with an equal molar amount of b-40, and the other steps were the same to obtain compound 40 (18.18 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 701.3132 (theoretical value: 701.3116). Theoretical element content (%) C 51 H 43 NS: C, 87.26; H, 6.17; N, 2.00. Measured element content (%): C, 87.29; H, 6.15; N, 2.00.

[0169] Synthesis Example 5: Preparation of Compound 73

[0170]

[0171] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 was replaced with an equal molar amount of b-73, and the other steps were the same to obtain compound 73 (21.54 g); HPLC purity ≥ 99.98%. Mass spectrum m / z: 809.3649 (theoretical value: 809.3658). Theoretical element content (%) C 61 H 47 NO: C, 90.45; H, 5.85; N, 1.73. Measured element content (%): C, 90.47; H, 5.83; N, 1.71.

[0172] Synthesis Example 6: Preparation of Compound 93

[0173]

[0174] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-73 and c-93, respectively, and the other steps were the same to obtain compound 93 (19.94 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 813.3922 (theoretical value: 813.3909). Theoretical element content (%) C 61 H 43 D4NO: C, 90.00; H, 6.31; N, 1.72. Measured element content (%): C, 90.00; H, 6.34; N, 1.70.

[0175] Synthesis Example 7: Preparation of Compound 127

[0176]

[0177] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-127 and c-127, respectively, and the other steps were the same to obtain compound 127 (18.77 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 837.3960 (theoretical value: 837.3971). Theoretical element content (%) C 63 H 51 NO: C, 90.29; H, 6.13; N, 1.67. Measured element content (%): C, 90.26; H, 6.15; N, 1.65.

[0178] Synthesis Example 8: Preparation of Compound 155

[0179]

[0180] According to the same preparation method as compound 1 in Synthesis Example 1, c-1 was replaced with an equal molar amount of c-155, and the other steps were the same to obtain compound 155 (19.75 g); HPLC purity ≥ 99.92%. Mass spectrum m / z: 909.3983 (theoretical value: 909.3971). Theoretical element content (%) C 69 H 51 NO: C, 91.06; H, 5.65; N, 1.54. Measured element content (%): C, 91.02; H, 5.68; N, 1.52.

[0181] Synthesis Example 9: Preparation of Compound 156

[0182]

[0183] According to the same preparation method as compound 1 in Synthesis Example 1, c-1 was replaced with an equal molar amount of c-156, and the other steps were the same to obtain compound 156 (19.63 g); HPLC purity ≥ 99.93%. Mass spectrum m / z: 889.4298 (theoretical value: 889.4284). Theoretical element content (%) C 67 H 55 NO: C, 90.40; H, 6.23; N, 1.57. Measured element content (%): C, 90.40; H, 6.24; N, 1.56.

[0184] Synthesis Example 10: Preparation of Compound 167

[0185]

[0186] According to the same preparation method as compound 1 in Synthesis Example 1, c-1 was replaced with an equal molar amount of c-167, and the other steps were the same to obtain compound 167 (18.97 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 859.3823 (theoretical value: 859.3814). Theoretical element content (%) C 65 H 49 NO: C, 90.77; H, 5.74; N, 1.63. Measured element content (%): C, 90.75; H, 5.78; N, 1.62.

[0187] Synthesis Example 11: Preparation of Compound 213

[0188]

[0189] According to the same preparation method as compound 1 in Synthesis Example 1, c-1 was replaced with an equal molar amount of c-213, and the other steps were the same to obtain compound 213 (20.16 g); HPLC purity ≥ 99.94%. Mass spectrum m / z: 885.3982 (theoretical value: 885.3971). Theoretical element content (%) C 67 H 51 NO: C, 90.81; H, 5.80; N, 1.58. Measured element content (%): C, 90.84; H, 5.80; N, 1.55.

[0190] Synthesis Example 12: Preparation of Compound 274

[0191]

[0192] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-73 and c-274, respectively, and the other steps were the same to obtain compound 274 (18.06 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 859.3806 (theoretical value: 859.3814). Theoretical element content (%) C 65 H 49 NO: C, 90.77; H, 5.74; N, 1.63. Measured element content (%): C, 90.73; H, 5.76; N, 1.65.

[0193] Synthesis Example 13: Preparation of Compound 294

[0194]

[0195] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-294 and c-294, respectively, and the other steps were the same to obtain compound 294 (16.32 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 685.3358 (theoretical value: 685.3345). Theoretical element content (%) C 51 H 43 NO: C, 89.31; H, 6.32; N, 2.04. Measured element content (%): C, 89.34; H, 6.30; N, 2.02.

[0196] Synthesis Example 14: Preparation of Compound 317

[0197]

[0198] According to the same preparation method as compound 1 in Synthesis Example 1, c-1 was replaced with an equal molar amount of c-317, and the other steps were the same to obtain compound 317 (18.37 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 819.4450 (theoretical value: 819.4440). Theoretical element content (%) C 61 H 57 NO: C, 89.34; H, 7.01; N, 1.71. Measured element content (%): C, 89.31; H, 7.03; N, 1.72.

[0199] Synthesis Example 15: Preparation of Compound 338

[0200]

[0201] According to the same preparation method as compound 1 in Synthesis Example 1, c-1 was replaced with an equal molar amount of c-338, and the other steps were the same to obtain compound 338 (19.07 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 837.3963 (theoretical value: 837.3971). Theoretical element content (%) C 63 H 51 NO: C, 90.29; H, 6.13; N, 1.67. Measured element content (%): C, 90.32; H, 6.11; N, 1.68.

[0202] Synthesis Example 16: Preparation of Compound 354

[0203]

[0204] According to the same preparation method as compound 1 in Synthesis Example 1, c-1 was replaced with an equal molar amount of c-354, and the other steps were the same to obtain compound 354 (20.08 g); HPLC purity ≥ 99.99%. Mass spectrum m / z: 807.3518 (theoretical value: 807.3501). Theoretical element content (%) C 61 H 45 NO: C, 90.67; H, 5.61; N, 1.73. Measured element content (%): C, 90.70; H, 5.60; N, 1.71.

[0205] Synthesis Example 17: Preparation of Compound 371

[0206]

[0207] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-371 and c-371, respectively, and the other steps were the same to obtain compound 371 (17.02 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 725.3669 (theoretical value: 725.3658). Theoretical element content (%) C 54 H 47 NO: C, 89.34; H, 6.53; N, 1.93. Measured element content (%): C, 89.30; H, 6.57; N, 1.95.

[0208] Synthesis Example 18: Preparation of Compound 403

[0209]

[0210] According to the same preparation method as compound 1 in Synthesis Example 1, c-1 was replaced with an equal molar amount of c-403, and the other steps were the same to obtain compound 403 (19.90 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 823.3441 (theoretical value: 823.3450). Theoretical element content (%) C 61 H 45 NO2: C, 88.91; H, 5.50; N, 1.70. Measured element content (%): C, 88.94; H, 5.48; N, 1.70.

[0211] Synthesis Example 19: Preparation of Compound 413

[0212]

[0213] According to the same preparation method as compound 1 in Synthesis Example 1, c-1 was replaced with an equal molar amount of c-413, and the other steps were the same to obtain compound 413 (16.86 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 659.2838 (theoretical value: 659.2824). Theoretical element content (%) C 48 H 37 NO2: C, 87.38; H, 5.65; N, 2.12. Measured element content (%): C, 87.41; H, 5.62; N, 2.10.

[0214] Synthesis Example 20: Preparation of Compound 430

[0215]

[0216] According to the same preparation method as compound 1 in Synthesis Example 1, c-1 was replaced with an equal molar amount of c-430, and the other steps were the same to obtain compound 430 (16.10 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 666.3255 (theoretical value: 666.3264). Theoretical element content (%) C 48 H 30 D7NO2: C, 86.45; H, 6.65; N, 2.10. Measured element content (%): C, 86.40; H, 6.68; N, 2.12.

[0217] Synthesis Example 21: Preparation of Compound 433

[0218]

[0219] According to the same preparation method as compound 1 in Synthesis Example 1, c-1 was replaced with an equal molar amount of c-433, and the other steps were the same to obtain compound 433 (17.89 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 709.2967 (theoretical value: 709.2981). Theoretical element content (%) C 52 H 39 NO2: C, 87.98; H, 5.54; N, 1.97. Measured element content (%): C, 87.95; H, 5.52; N, 1.99.

[0220] Synthesis Example 22: Preparation of Compound 503

[0221]

[0222] According to the same preparation method as compound 1 in Synthesis Example 1, c-1 was replaced with an equal molar amount of c-503, and the other steps were the same to obtain compound 503 (19.97 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 814.3844 (theoretical value: 814.3861). Theoretical element content (%) C 60 H 42 D4N2O: C, 88.42; H, 6.18; N, 3.44. Measured element content (%): C, 88.45; H, 6.20; N, 3.40.

[0223] Synthesis Example 23: Preparation of Compound 515

[0224]

[0225] According to the same preparation method as compound 1 in Synthesis Example 1, c-1 was replaced with an equal molar amount of c-515, and the other steps were the same to obtain compound 515 (20.72 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 810.3622 (theoretical value: 810.3610). Theoretical element content (%) C 60 H 46 N2O: C, 88.86; H, 5.72; N, 3.45. Measured element content (%): C, 88.88; H, 5.70; N, 3.43.

[0226] Synthesis Example 24: Preparation of Compound 542

[0227]

[0228] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-542 and c-542, respectively, and the other steps were the same to obtain compound 542 (18.62 g); HPLC purity ≥ 99.93%. Mass spectrum m / z: 805.3732 (theoretical value: 805.3740). Theoretical element content (%) C 58 H 51 NOSi: C, 86.42; H, 6.38; N, 1.74. Measured element content (%): C, 86.40; H, 6.37; N, 1.78.

[0229] Synthesis Example 25: Preparation of Compound 568

[0230]

[0231] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-542 and c-568, respectively, and the other steps were the same to obtain compound 568 (17.68 g); HPLC purity ≥ 99.94%. Mass spectrum m / z: 814.3958 (theoretical value: 814.3971). Theoretical element content (%) C 61 H 42 D5NO: C, 89.89; H, 6.43; N, 1.72. Measured element content (%): C, 89.86; H, 6.46; N, 1.71.

[0232] Synthesis Example 26: Preparation of Compound 575

[0233]

[0234] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-73 and c-575, respectively, and the other steps were the same to obtain compound 575 (19.37 g); HPLC purity ≥ 99.94%. Mass spectrum m / z: 747.3511 (theoretical value: 747.3501). Theoretical element content (%) C 56 H 45 NO: C, 89.92; H, 6.06; N, 1.87. Measured element content (%): C, 89.90; H, 6.10; N, 1.85.

[0235] Synthesis Example 27: Preparation of Compound 577

[0236]

[0237] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-73 and c-577, respectively, and the other steps were the same to obtain compound 577 (21.26 g); HPLC purity ≥ 99.93%. Mass spectrum m / z: 809.3642 (theoretical value: 809.3658). Theoretical element content (%) C 61 H 47 NO: C, 90.45; H, 5.85; N, 1.73. Measured element content (%): C, 90.46; H, 5.84; N, 1.72.

[0238] Synthesis Example 28: Preparation of Compound 708

[0239]

[0240] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-73 and c-708, respectively, and the other steps were the same to obtain compound 708 (21.10 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 825.3415 (theoretical value: 825.3429). Theoretical element content (%) C 61 H 47 NS: C, 88.69; H, 5.73; N, 1.70. Measured element content (%): C, 88.72; H, 5.70; N, 1.70.

[0241] Synthesis Example 29: Preparation of Compound 709

[0242]

[0243] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-709 and c-709, respectively, and the other steps were the same to obtain compound 709 (19.53 g); HPLC purity ≥ 99.93%. Mass spectrum m / z: 763.3286 (theoretical value: 763.3273). Theoretical element content (%) C 56 H 45 NS: C, 88.03; H, 5.94; N, 1.83. Measured element content (%): C, 88.00; H, 5.96; N, 1.81.

[0244] Synthesis Example 30: Preparation of Compound 747

[0245]

[0246] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-747 and c-747, respectively, and the other steps were the same to obtain compound 747 (20.12 g); HPLC purity ≥ 99.92%. Mass spectrum m / z: 957.4355 (theoretical value: 957.4368). Theoretical element content (%) C 71 H 59 NS: C, 88.99; H, 6.21; N, 1.46. Measured element content (%): C, 88.99; H, 6.24; N, 1.43.

[0247] Synthesis Example 31: Preparation of Compound 767

[0248]

[0249] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-709 and c-767, respectively, and the other steps were the same to obtain compound 767 (21.96 g); HPLC purity ≥ 99.98%. Mass spectrum m / z: 935.4538 (theoretical value: 935.4525). Theoretical element content (%) C 69 H 61 NS: C, 88.51; H, 6.57; N, 1.50. Measured element content (%): C, 88.50; H, 6.53; N, 1.53.

[0250] Synthesis Example 32: Preparation of Compound 783

[0251]

[0252] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-294 and c-783, respectively, and the other steps were the same to obtain compound 783 (16.48 g); HPLC purity ≥ 99.91%. Mass spectrum m / z: 702.3081 (theoretical value: 702.3069). Theoretical element content (%) C 50 H 42 N2S: C, 85.43; H, 6.02; N, 3.99. Measured element content (%): C, 85.40; H, 6.05; N, 3.99.

[0253] Synthesis Example 33: Preparation of Compound 924

[0254]

[0255] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-924 and c-924, respectively, and the other steps were the same to obtain compound 924 (18.64 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 691.2378 (theoretical value: 691.2367). Theoretical element content (%) C 48 H 37 NS2: C, 83.32; H, 5.39; N, 2.02. Measured element content (%): C, 83.35; H, 5.36; N, 2.00.

[0256] Synthesis Example 34: Preparation of Compound 969

[0257]

[0258] According to the same preparation method as compound 1 in Synthesis Example 1, c-1 was replaced with an equal molar amount of c-969, and the other steps were the same to obtain compound 969 (20.98 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 899.4138 (theoretical value: 899.4127). Theoretical element content (%) C 68 H 53 NO: C, 90.73; H, 5.93; N, 1.56. Measured element content (%): C, 90.75; H, 5.91; N, 1.54.

[0259] Synthesis Example 35: Preparation of Compound 979

[0260]

[0261] According to the same preparation method as compound 1 in Synthesis Example 1, b-1 and c-1 were replaced by equimolar amounts of b-979 and c-979, respectively, and the other steps were the same to obtain compound 979 (18.72 g); HPLC purity ≥ 99.91%. Mass spectrum m / z: 848.4121 (theoretical value: 848.4130). Theoretical element content (%) C 60 H 52 N2: C, 90.53; H, 6.17; N, 3.30. Measured element content (%): C, 90.56; H, 6.15; N, 3.29. Green organic light-emitting device (hole transport layer)

[0262] [Comparative Example 1-2]:

[0263] Comparative Example 1: Preparation of organic light-emitting devices by vacuum thermal evaporation. The experimental steps are as follows: the ITO-Ag-ITO substrate is washed three times in distilled water, ultrasonically washed for 15 minutes, and after the distilled water washing is completed, ultrasonically washed with isopropanol, acetone, methanol and other solvents in sequence, dried at 120°C, and sent to the evaporator.

[0264] On the prepared ITO-Ag-ITO substrate, the hole injection layer HAT-CN / 30nm, the hole transport layer HT-1 / 100nm, the main GH: doped GD (mass ratio 92%: 8% mixed) / 29nm, and then the electron transport layer ET and Liq (doping ratio is 1:1 by mass ratio) / 30nm, the electron injection layer LiF / 1nm, the cathode Mg-Ag (Mg: Ag mass ratio = 1:9) / 13nm, and the cover layer CP / 70nm is evaporated on the cathode. The device is sealed in a glove box to prepare an organic light-emitting device. After completing the production of the organic light-emitting device according to the above steps, the photoelectric performance of the device is measured. The molecular structure formula of the relevant materials is as follows:

[0265]

[0266] Comparative Example 2: The hole transport layer material HT-1 in Comparative Example 1 was replaced with HT-2, and the organic light-emitting device of Comparative Example 2 was manufactured in the same manner as Comparative Example 1.

[0267] [Device Example 1-35]

[0268] Device Examples 1-35: The hole transport layer material HT-1 of the organic light-emitting device is replaced with compounds 1, 16, 21, 40, 73, 93, 127, 155, 156, 167, 213, 274, 294, 317, 338, 354, 371, 403, 413, 430, 433, 503, 515, 542, 568, 575, 577, 708, 709, 747, 767, 783, 924, 969, and 979 of the present invention in sequence, and the other steps are the same as those in Comparative Example 1.

[0269] The test software, computer, K2400 digital source meter produced by Keithley Company of the United States and PR788 spectrum scanning luminance meter of PhotoResearch Company of the United States are combined into a joint IVL test system to test the luminous efficiency of organic light-emitting devices. The life test adopts the M6000 OLED life test system of McScience Company. The test environment is the atmospheric environment and the temperature is room temperature. The test results of the luminous characteristics of the organic light-emitting device are shown in Table 1. Table 1 shows the test results of the luminous characteristics of the light-emitting device prepared by the compound prepared in the embodiment of the present invention and the comparative substance.

[0270] [Table 1] Luminous characteristics test of light emitting device

[0271]

[0272]

[0273] Note: T97 refers to the current density of 10mA / cm 2 Under the condition of , the time taken by the device brightness to decay to 97%;

[0274] It can be seen from the results in Table 1 that the compounds of the present invention are applied to organic light-emitting devices as hole transport layer materials. Compared with Comparative Example 1, it can be seen that the effects of condensed aromatic groups (such as naphthalene, anthracene, phenanthrene, benzoaliphatic rings, fluorenes, etc.) and condensed heteroaromatic groups (such as dibenzofuran / thiophene, spirofluorene oxygen anthracene, etc.) are better than biphenyl, which has a greater impact on improving the luminous efficiency and service life.

[0275] Red organic light-emitting device (second hole transport layer)

[0276] [Comparative Example 3] Device Preparation Example:

[0277] Comparative Example 3: Preparation of organic light-emitting devices by vacuum thermal evaporation. The experimental steps are as follows: the ITO-Ag-ITO substrate is washed three times in distilled water, ultrasonically washed for 15 minutes, and after the distilled water washing is completed, ultrasonically washed with isopropanol, acetone, methanol and other solvents in sequence, dried at 120°C, and sent to the evaporator.

[0278] On the prepared ITO-Ag-ITO substrate, the hole injection layer HAT-CN / 30nm, the first hole transport layer HT / 65nm, the second hole transport layer HT-1 / 35nm, the main body RH: doping material RD (mass ratio 97%: 3% mixed) / 30nm, then the electron transport layer ET and Liq (doping ratio is 1:1) / 30nm, the electron injection layer LiF / 1nm, the cathode Mg-Ag (Mg: Ag mass ratio = 1:9) / 13nm, and the cover layer CP / 69nm is evaporated on the cathode. The device is sealed in a glove box to prepare an organic light-emitting device. After completing the production of the organic light-emitting device according to the above steps, the photoelectric performance of the device is measured. The molecular structure formula of the relevant materials is as follows:

[0279]

[0280] [Examples 36-60]

[0281] Examples 36-60: The second hole transport layer material of the organic light-emitting device is replaced with compounds 1, 16, 40, 73, 93, 127, 213, 274, 294, 317, 354, 371, 403, 413, 430, 433, 515, 568, 577, 708, 767, 783, 924, 969, 979 of the present invention in sequence, and the other steps are the same as those of Comparative Example 3. The instruments, models and test environment used to test the driving voltage, luminous efficiency and life of the organic light-emitting device are the same as those in Table 1. The test results of the luminescent characteristics of the obtained device are shown in Table 2. Table 2 shows the test results of the luminescent characteristics of the compounds prepared in the examples of the present invention and the luminescent devices prepared by the comparative substances.

[0282] [Table 2] Luminous characteristics test of light emitting device

[0283]

[0284]

[0285] It can be seen from the results in Table 2 that the aromatic amine derivatives of the present invention are applied to organic light-emitting devices as the second hole transport layer material, which significantly improves the luminous efficiency and service life of the organic light-emitting device compared with Comparative Example 3, and is an organic light-emitting material with good performance.

[0286] Blue organic light emitting device (covering layer)

[0287] [Comparative Example 4]:

[0288] Comparative Example 4: Preparation of organic light-emitting devices by vacuum thermal evaporation. The experimental steps are as follows: the ITO-Ag-ITO substrate is washed three times in distilled water, ultrasonically washed for 15 minutes, and after the distilled water washing is completed, ultrasonically washed with isopropanol, acetone, methanol and other solvents in sequence, dried at 120°C, and sent to the evaporator.

[0289] On the prepared ITO-Ag-ITO substrate, the hole injection layer HAT-CN / 30nm, the hole transport layer HT / 100nm, the main BH: doped BD (98%: 2% mixed) / 25nm, and then the electron transport layer ET and Liq (doping ratio is 1:1 by mass ratio) / 30nm, the electron injection layer LiF / 1nm, the cathode Mg-Ag (Mg: Ag mass ratio = 1:9) / 14nm, and the cover layer CP-1 / 72nm is evaporated on the cathode. The device is sealed in a glove box to prepare an organic light-emitting device. After completing the production of the organic light-emitting device according to the above steps, the photoelectric performance of the device is measured. The molecular structure formula of the relevant materials is as follows:

[0290]

[0291] [Device Examples 61-75]

[0292] Device Examples 61-75: The covering layer material CP-1 of the organic light-emitting device is replaced with the compounds 1, 16, 73, 127, 274, 294, 354, 403, 413, 430, 433, 577, 708, 767, 924 of the present invention in turn, and the other steps are the same as those of Comparative Example 4. The instruments, models and test environment used to test the driving voltage, luminous efficiency and life of the organic light-emitting device are the same as those in Table 1. The test results of the luminous properties of the obtained organic light-emitting device are shown in Table 3. Table 3 shows the test results of the luminous properties of the compounds prepared in the examples of the present invention and the light-emitting devices prepared by the comparative substances.

[0293] [Table 3] Luminous characteristics test of light emitting device

[0294]

[0295]

[0296] Note: T95 refers to the current density of 10mA / cm 2 Under the condition of , the time taken by the device brightness to decay to 95%;

[0297] It can be seen from the results in Table 3 that the triarylamine organic compound of the present invention is applied to an organic light-emitting device as a covering layer material. Compared with Comparative Example 4, it can effectively improve the light extraction efficiency, thereby improving the luminous efficiency of the organic light-emitting device, and is an organic light-emitting device covering layer material with good performance.

[0298] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. A triarylamine compound, characterized in that The molecular structure is shown in Formula I: Wherein, the ring A is selected from one of the groups represented by formula a, formula b, and formula c: The R m , R n Independently selected from any one of hydrogen, deuterium, C1-C6 alkyl, C3-C15 cycloalkyl, C6-C25 aryl; m is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; "*" is the connection site; The X is selected from O, S or NR c , wherein R c is selected from a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C25 aryl group, a substituted or unsubstituted fused ring group of a C6-C30 aromatic ring and a C3-C30 aliphatic ring, a substituted or unsubstituted C2-C25 heteroaryl group, or R c The corresponding nitrogen atom is the site of connection with the bridge L2; The ring B is selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, a substituted or unsubstituted triazine ring, a substituted or unsubstituted pyrazine ring, a substituted or unsubstituted pyridazine ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted quinazoline ring, a substituted or unsubstituted quinoxaline ring, a substituted or unsubstituted azaphenanthren ring, and a substituted or unsubstituted azaanthracene ring; The R e are the same as or different from each other and are selected from one of hydrogen, deuterium, halogen atoms, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C25 heteroaryl; said e is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; Ar1 is selected from a substituted or unsubstituted C8-C25 fused aromatic group, a substituted or unsubstituted C6-C30 fused aromatic ring and a C3-C30 aliphatic ring, and a substituted or unsubstituted C2-C25 fused heteroaromatic group; The L1, L2, and L3 are independently selected from a single bond, a substituted or unsubstituted C6-C25 arylene group, a substituted or unsubstituted C3-C10 aliphatic ring and a C6-C25 aromatic ring sub-condensed ring group, and a substituted or unsubstituted C2-C20 heteroarylene group; The R1 and R2 are the same as or different from each other, and are independently selected from one of hydrogen, deuterium, halogen atoms, cyano groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 cycloalkyl groups, substituted or unsubstituted C2-C30 alkenyl groups, substituted or unsubstituted C6-C25 aryl groups, substituted or unsubstituted C6-C30 aromatic rings and C3-C30 aliphatic rings fused ring groups, substituted or unsubstituted C2-C25 heteroaryl groups, or adjacent R1 and adjacent R2 may be connected to form a ring structure; The a is selected from 0, 1, 2, 3 or 4; the b is selected from 0, 1, 2 or 3.

2. A triarylamine compound according to claim 1, characterized in that: The formula a is selected from one of the following groups: The formula b is selected from one of the following groups: The formula C is selected from one of the following groups:

3. A triarylamine compound according to claim 1, characterized in that: Said Any one selected from the following groups: The X is selected from O, S or NR c , wherein R c R is selected from hydrogen, deuterium, trifluoromethyl, a substituted or unsubstituted one of the following groups: trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, indanyl, indenyl, benzocyclobutyl, benzocyclopropyl, or R c The corresponding nitrogen atom is the site of connection with the bridge L2; The R e are the same as or different from each other and are selected from one of hydrogen, deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, trideuterophenylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, bornyl, indanyl, indenyl, benzocyclobutyl, benzocyclobutenyl, benzocyclopropyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, anthracenyl, phenanthryl, triphenylene, deuterated phenyl, deuterated naphthyl and deuterated biphenyl; wherein R e It can also be R ee Replaced by R ee One or more selected from hydrogen, deuterium, trimethylsilyl, triphenylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, tolyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, anthracenyl, phenanthryl; when substituted by multiple substituents, the multiple substituents are the same or different from each other; The e1 is selected from 0 or 1; the e2 is selected from 0, 1 or 2; the e3 is selected from 0, 1, 2 or 3; the e4 is selected from 0, 1, 2, 3 or 4; the e5 is selected from 0, 1, 2, 3, 4 or 5; the e6 is selected from 0, 1, 2, 3, 4, 5 or 6; the e7 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the e8 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the e9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

4. A triarylamine compound according to claim 1, characterized in that: The Ar1 is selected from any one of the following groups: wherein the ring C is selected from a substituted or unsubstituted three-membered, four-membered, five-membered, six-membered, seven-membered or eight-membered saturated or unsaturated aliphatic ring; the ring D is selected from a substituted or unsubstituted benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a triazine ring, a pyrazine ring, a pyridazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, an azaphenanthren ring, and an azaanthracene ring; X1 is selected from O, S or NR s , wherein R s One selected from hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C25 heteroaryl; Said X2 is selected from O or S; The X3 is selected from CR7R8, O, S or NR9, wherein the R7 and R8 are independently selected from one of substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, and substituted or unsubstituted C6-C25 aryl; the R9 is selected from one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C25 heteroaryl; The R3 is selected from hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C3-C60 heteroaryl; or the nitrogen atom corresponding to R3 is the site of connection with the bridge L1; The R4 and R5 are independently selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C25 heteroaryl, or adjacent R4 and R5 can be connected to form a ring structure; The R h , R k are the same as or different from each other and are each independently selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C25 heteroaryl, or adjacent R h Can be connected into a ring structure; The h1 is selected from 0, 1, 2 or 3; the h2 is selected from 0, 1, 2, 3 or 4; the h5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the h7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the k is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.

5. A triarylamine compound according to claim 1, characterized in that: The L1, L2, and L3 are independently selected from a single bond, the following groups, and a combination thereof: The R r are the same as or different from each other and are selected from any one of hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, and a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring; The r0 is selected from 0, 1 or 2; the r1 is selected from 0, 1, 2, 3 or 4; the r2 is selected from 0, 1, 2, 3, 4, 5 or 6; the r3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the r4 is selected from 0, 1, 2 or 3; The R x , R y Independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl or substituted or unsubstituted groups: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothienyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazolyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, indenyl.

6. A triarylamine compound according to claim 1, characterized in that: The triarylamine compound is selected from any one of the following chemical structures:

7. 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, characterized in that: The organic layer contains any one or a combination of at least two of the triarylamine compounds according to any one of claims 1 to 6.

8. An organic light emitting device according to claim 7, characterized in that: The organic layer comprises a hole transport region, and at least one layer in the hole transport region comprises any one or a combination of at least two of the triarylamine compounds according to any one of claims 1 to 6.

9. The organic light emitting device according to claim 7, characterized in that: The organic layer includes a covering layer, and the covering layer contains any one or a combination of at least two of the triarylamine compounds according to any one of claims 1 to 6.

10. An organic light-emitting device according to claim 7, wherein the organic layer is located between the anode and the cathode, the organic layer comprises a first light-emitting portion, a second light-emitting portion and a charge generation layer, the first light-emitting portion is located between the anode and the cathode, the second light-emitting portion is located between the first light-emitting portion and the cathode, and the charge generation layer is located between the first light-emitting portion and the second light-emitting portion, characterized in that: The charge generating layer contains any one or a combination of at least two of the triarylamine compounds according to any one of claims 1 to 6.

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