An arylamine derivative and an organic light-emitting device thereof

Abstract

The application provides an arylamine derivative and an organic light-emitting device thereof, and relates to the technical field of organic photoelectric materials.The derivative of the application takes triarylamine as a center, connects a dibenzo five-membered ring at the 9-position of a fluorenyl group as a substituent on the triarylamine, the introduction of the substituent can reduce the conjugation degree of the derivative, thereby reducing the hole mobility, meanwhile, the introduction of a silyl group in formula I has stronger electron-donating capacity, and further enhances the electron-donating capacity of the derivative.The derivative of the application has suitable hole mobility, is a good hole transport material, and can improve the light-emitting efficiency of the organic light-emitting device and the service life of the device.The derivative of the application can be widely applied to the fields of panel display, lighting sources, flexible OLEDs, organic solar cells, organic photosensitive bodies, indicator boards, signal lamps and the like.

Description

Technical Field

[0001] This invention relates to the field of organic optoelectronic materials technology, and in particular to an aromatic amine derivative and its organic light-emitting device. Background Technology

[0002] Organic light emission generally refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) utilizing organic light emission exhibit characteristics such as wide viewing angle, excellent contrast ratio, fast response time, excellent brightness, driving voltage, and response speed, and have therefore been the subject of much research.

[0003] Organic light-emitting devices (OLEDs) typically have a structure including an anode, a cathode, and an organic material layer between or outside the anode and cathode. When a voltage is applied between the two electrodes, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode. When the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons return to their ground state. Based on the light emission path, OLEDs can be classified into bottom-emitting OLEDs and top-emitting OLEDs. A bottom-emitting OLED structure generally includes a transparent ITO anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode. A top-emitting OLED structure generally includes an opaque ITO anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a cathode, and a capping layer. The hole / electron injection layer is mainly used to reduce the injection barrier between the electrode and the corresponding carrier transport layer, thereby improving the carrier injection efficiency and reducing the device driving voltage. The hole / electron transport layer is used for the migration of corresponding carriers in the device, mainly to improve the carrier mobility and luminous efficiency. The light-emitting layer can be composed of a single material or a host material and a guest doped material. The capping layer is mainly used in top-emitting organic light-emitting devices, located on the side of the cathode away from the anode. It usually uses organic electroluminescent materials with a high refractive index to reduce total internal reflection of light inside the device, thereby improving the luminous efficiency of the device.

[0004] In recent years, with the continuous advancement of industrial technology, the luminous efficiency and lifespan of organic light-emitting devices have made great progress. However, the imbalance of charge carrier injection inside the device and the low light extraction efficiency have always been major problems plaguing the industry. Therefore, developing a material that can promote the balance of charge carrier injection and improve the light extraction efficiency has become an urgent problem to be solved. Summary of the Invention

[0005] The purpose of this invention is, based on existing technology and with industrialization as the goal, to provide an aromatic amine derivative and its organic light-emitting device. The organic light-emitting device prepared using this aromatic amine derivative can be applied to a hole transport layer or an auxiliary hole transport layer (second hole transport layer) to develop organic light-emitting devices with high luminous efficiency and long lifetime. Its general molecular structure is shown in Formula I:

[0006] An aromatic amine derivative, characterized in that its molecular structure is shown in Formula I:

[0007]

[0008] Wherein, X is selected from O, S or NR. e The R e It is selected from one of the following: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring.

[0009] Ar1 and Ar2 are independently selected from one of the following: 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 C2-C25 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring.

[0010] The R is selected from one of hydrogen, deuterium, tritium, cyano, halogen, 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 C2-C25 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group;

[0011] The L0, L1, L2, L a It is independently selected from one of the following: single bond, substituted or unsubstituted C6-C25 arylene, substituted or unsubstituted C2-C25 heteroarylene, substituted or unsubstituted C3-C10 aliphatic ring and C6-C25 aromatic ring fused and cycloalgyl groups;

[0012] The R a R b R c R dThey may be identical or different from each other, and each is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, halogen, 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 C2-C25 heteroaryl, substituted or unsubstituted aromatic rings of C6-C30 and fused rings of C3-C30 aliphatic rings, or adjacent R a Adjacent R b Adjacent R c Adjacent R d They can be connected to form a ring structure;

[0013] The value of 'a' is selected from 0, 1, 2, 3, or 4; the value of 'b' is selected from 0, 1, 2, 3, or 4.

[0014] c is selected from 0, 1, 2, or 3; d is selected from 0, 1, 2, or 3;

[0015] The Ar1, Ar2, R, R a R b R c R d R e L0, L1, L2, L a At least one of the substituted or unsubstituted silyl groups is substituted.

[0016] 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 aromatic amine derivatives described in the present invention.

[0017] The beneficial effects of this invention are:

[0018] This invention provides an aromatic amine derivative and its organic light-emitting device. The derivative of this invention is centered on a triarylamine, with a dibenzo5-membered ring attached at the 9-position of the fluorene group as a substituent on the triarylamine. The introduction of this substituent reduces the conjugation degree of the derivative, thereby reducing the hole mobility. At the same time, the introduction of a silyl group in Formula I has a stronger electron-donating ability, further enhancing the electron-donating ability of the derivative. The derivative of this invention has a suitable hole mobility and is a good hole transport material, which can improve the luminous efficiency and lifespan of organic light-emitting devices. Detailed Implementation

[0019] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of the present invention.

[0020] In the compounds of the present invention, any atom not specified as a particular isotope is included as any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances.

[0021] In this invention, the use of "H" and "hydrogen" refers to the presence of no more than the natural abundance of deuterium or tritium atoms in the chemical structure, for example, no more than 0.0156 atomic% of deuterium. "D" and "deuterium" refer to a deuterium abundance greater than the natural abundance, for example, any value exceeding 0.1 atomic%, 1 atomic%, or 10 atomic%, such as approximately 95 atomic% of deuterium. In this invention, the omission of undrawn hydrogen atoms signifies "H" or "hydrogen".

[0022] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring.

[0023] For example, Can represent Can represent Can represent And so on.

[0024] The halogens mentioned in this invention refer to fluorine, chlorine, bromine, and iodine.

[0025] The silyl group mentioned in this invention refers to a silane group formed by removing one hydrogen atom from a silane molecule. Preferably, the silyl group has the -Si(R) group. k The structure shown in Figure 3, R k The silyl group is selected from any one of H, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C15 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl groups, and substituted or unsubstituted C2-C30 heteroaryl groups, but is not limited thereto. The substituted silyl group specifically includes trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but is not limited thereto. The silyl group is preferably trimethylsilyl, triethylsilyl, triphenylsilyl, diphenylsilyl, or phenylsilyl.

[0026] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. It 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 is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomers of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0027] The chain alkyl groups with more than three carbon atoms described in this invention include their isomers. For example, propyl includes n-propyl and isopropyl, and butyl includes n-butyl, sec-butyl, isobutyl, and tert-butyl. And so on.

[0028] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one 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. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, camphenyl, norbornyl, etc., but are not limited thereto. The cycloalkyl group is preferably cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, or norbornyl.

[0029] The alkenyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from an olefin molecule. The alkenyl group 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 group 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 preferred alkenyl group is vinyl.

[0030] The alkenyl groups with more than three carbon atoms described in this invention include their isomers. For example, propenyl groups include 1-propenyl or 2-propenyl groups; butenyl groups include 1-butenyl, 2-butenyl, or 3-butenyl groups; pentenyl groups include 1-pentenyl, 2-pentenyl, 3-pentenyl, and 4-pentenyl groups; and hexenyl groups include 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, and 5-hexenyl groups. And so on.

[0031] The aryl group described in this invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, 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 refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited thereto; the polycyclic aryl 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 fused-ring aryl refers to an aryl group containing two or more aromatic rings fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, perylene, fluorene, benzo[a]fluorene, triphenylene, fluoranyl, spirodifluorene, etc., but not limited thereto. The aryl group is preferably phenyl, biphenyl, terphenyl, naphthyl (preferably 2-naphthyl), anthracene (preferably 2-anthrayl), phenanthryl, pyrene, peryl, fluorene, benzo[a]fluorene, triphenylene, or spirodifluorene.

[0032] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. 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 linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. The monocyclic heteroaryl groups include, but are not limited to, pyridinyl, pyrimidinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridinyl, bipyrimidinyl, phenylpyridinyl, etc.; the fused-ring heteroaryl groups include, but are not limited to, quinolinyl, isoquinolinyl, indolyl, benzothiopheneyl, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiapheneyl, carbazolyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, etc., but are not limited to. The aforementioned heteroaryl groups are preferably pyridyl, pyrimidinyl, thiophene, furanyl, benzothiophene, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophene, benzodibenzothiophene, benzodibenzofuranyl, carbazolyl, acridinel, phenoxazinyl, phenthiazinyl, and phenoxthialyl.

[0033] The arylene group referred to in this invention refers to the general term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, 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 includes, but is not limited to, phenylene; the polycyclic arylene includes, but is not limited to, biphenylene, terphenylene; and the fused-ring arylene includes, but is not limited to, naphthylene, anthracene, phenanthrene, fluorene, pyrene, trimethyleneene, fluorene, and phenylfluorene. The aforementioned arylene groups are preferably phenylene, biphenylene, terphenylene, naphthyl, fluorene, or phenylfluorene.

[0034] The fused aliphatic and aromatic rings and cycloalkanes mentioned in this invention refer to the general term for divalent groups remaining after removing two hydrogen atoms from the fused aliphatic and aromatic rings. Preferably, they have 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 12 carbon atoms. Examples may include, but are not limited to, benzo[a]cyclopropyl, benzo[a]cyclobutyl, benzo[a]cyclopentyl, benzo[a]cyclohexyl, benzo[a]cycloheptyl, benzo[a]cyclopentenyl, benzo[a]cyclohexenyl, benzo[a]cycloheptenyl, naphtho[a]cyclopropyl, naphtho[a]cyclobutyl, naphtho[a]cyclopentyl, and naphtho[a]cyclohexyl, etc.

[0035] The fused ring of aromatic and aliphatic rings described in this invention refers to a molecule containing one or more aromatic rings and one or more aliphatic rings fused together by sharing two adjacent carbon atoms. 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 benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0036] The aliphatic ring described in this invention refers to a cyclic hydrocarbon with aliphatic properties, containing a closed carbon ring in the molecule, preferably with 3 to 60 carbon atoms, more preferably 3 to 30 carbon atoms, even more preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. It can form monocyclic or polycyclic hydrocarbons, and can be completely unsaturated or partially unsaturated. Specific examples include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited to these. Multiple monocyclic hydrocarbons can also be connected in various ways: two rings in the molecule can share a carbon atom to form a spiro ring; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings can also be interconnected to form a cage-like structure.

[0037] The term "substituted..." as used in this invention refers to monosubstituted or polysubstituted groups, such as substituted silyl, substituted alkyl, substituted cycloalkyl, substituted alkenyl, substituted aryl, substituted fused cyclic groups of aromatic and aliphatic rings, substituted arylene, substituted fused and cyclic groups of aliphatic and aromatic rings, etc., which are independently selected from, but not limited to, deuteryl, 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., preferably selected from deuteryl. The substituents may be mono- or poly-substituted with groups such as methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzo[a]phenanthrene, perylene, pyrene, benzyl, tolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, diphenylamino, dimethylamino, carbazole, 9-phenylcarbazole, acridine, furanyl, thiophene, benzofuranyl, benzothiophene, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophene, phenothiazinyl, phenothiazinyl, and indole. Furthermore, the above substituents may also be substituted by one or more of the substituents described above, such as deuterium, halogen, cyano, alkyl, cycloalkyl, or aryl.

[0038] Unless otherwise stated, the term "ring" as used herein refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a combination thereof, which may contain saturated or unsaturated rings.

[0039] The cyclic structure formed by bonding as described in this invention refers to two groups being linked together by chemical bonds and optionally aromatized. Examples are shown below:

[0040]

[0041] In this invention, the ring formed by the 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 fused ring, such as benzene, naphthalene, fluorene, cyclopropane, cyclobutane, cyclopentene, cyclopentane, cyclohexene, cyclohexane, cyclopentanophenene, cyclohexanophenene, quinoline, isoquinoline, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0042] In this invention, "at least one" means, under permissible conditions, one, two, three, four, five, six or more.

[0043] In this invention, "one or more" means, under permissible conditions, one, two, three, four, five, six or more.

[0044] This invention provides an aromatic amine derivative with the molecular structure shown in Formula I:

[0045]

[0046] Wherein, X is selected from O, S or NR. e The R e It is selected from one of the following: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring.

[0047] Ar1 and Ar2 are independently selected from one of the following: 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 C2-C25 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring.

[0048] The R is selected from one of hydrogen, deuterium, tritium, cyano, halogen, 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 C2-C25 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group;

[0049] The L0, L1, L2, L aIt is independently selected from one of the following: single bond, substituted or unsubstituted C6-C25 arylene, substituted or unsubstituted C2-C25 heteroarylene, substituted or unsubstituted C3-C10 aliphatic ring and C6-C25 aromatic ring fused and cycloalgyl groups;

[0050] The R a R b R c R d They may be identical or different from each other, and each is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, halogen, 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 C2-C25 heteroaryl, substituted or unsubstituted aromatic rings of C6-C30 and fused rings of C3-C30 aliphatic rings, or adjacent R a Adjacent R b Adjacent R c Adjacent R d They can be connected to form a ring structure;

[0051] The value of 'a' is selected from 0, 1, 2, 3, or 4; the value of 'b' is selected from 0, 1, 2, 3, or 4.

[0052] c is selected from 0, 1, 2, or 3; d is selected from 0, 1, 2, or 3;

[0053] The Ar1, Ar2, R, R a R b R c R d R e L0, L1, L2, L a At least one of the substituted or unsubstituted silyl groups is substituted.

[0054] Preferably, the substituted or unsubstituted silyl group is selected from the group shown in Formula A:

[0055]

[0056] The R1, R2, and R3 are the same or different and are selected from any one of the following: deuterium, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C25 heteroaryl groups, substituted or unsubstituted C6-C30 aromatic rings, and C3-C30 aliphatic ring fused ring groups.

[0057] Preferably, formula A is selected from one of the following groups:

[0058]

[0059] Preferably, Ar1, Ar2, R, R a R b R c R d R e L0, L1, L2, L a At least one of the substituted or unsubstituted silyl groups is substituted.

[0060] Preferably, at least one of Ar1 and Ar2 is substituted by one or more of the groups shown in Formula A.

[0061] Preferably, one or both of the Ar1 and Ar2 are each substituted by one or more of the groups shown in Formula A.

[0062] Preferably, L0, L1, L2, L a At least one of the groups is replaced by one or more of the groups shown in Formula A.

[0063] Preferably, L0, L1, L2, L a One, two, three, or four of them are each replaced by one or more of the groups shown in Formula A.

[0064] Preferably, the R, R a R b R c R d R e At least one of the groups is replaced by one or more of the groups shown in Formula A.

[0065] Preferably, the R, R a R b R c R d R e One, two, three, four, five, or six of them are each substituted by one or more of the groups shown in Formula A.

[0066] More preferably, the Ar1 is substituted with one or more of the groups shown in Formula A.

[0067] More preferably, the Ar2 is substituted with one or more of the groups shown in Formula A.

[0068] Preferably, Ar1 and Ar2 are independently selected from any one of the following groups:

[0069]

[0070] Wherein, Y is selected from O, S or NR. y The R y It is selected from one of the following: formula A, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, or substituted or unsubstituted C6-C60 aryl;

[0071] The y is selected from CH or N atoms;

[0072] V is selected from O, S, NR u or CR v R w The R u Selected from one of formula A, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; or R u The corresponding nitrogen atom is the site connected to bridging L1 or L2;

[0073] The R v R w Independently selected from formula A, hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, or one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, tetrahydronaphthyl, dihydronaphthyl, indenyl, indenyl, or adjacent R v R w Groups can bond together to form substituted or unsubstituted cyclic structures; or R v R w The carbon atom corresponding to one of them is the site connected to bridging L1 or L2;

[0074] The z that are the same or different are selected from CR n Or N atoms, and at least one z is selected from N atoms, wherein R nThe groups are identical or different from each other, selected from formula A, hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, or substituted or unsubstituted from one of the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, indenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene. The substituents in "substituted or unsubstituted" are selected from one or more of deuterium, tritium, cyano, halogen, trifluoromethyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, phenyl, biphenyl, and naphthyl, or optionally two adjacent R groups. n Groups can bond together to form substituted or unsubstituted benzene rings, substituted or unsubstituted pyridine rings, substituted or unsubstituted pyrimidine rings, or substituted or unsubstituted three- to eight-membered aliphatic rings; when substituted by multiple substituents, the multiple substituents may be the same as or different from each other;

[0075] The n1 is selected from 1, 2, 3, 4 or 5; the n2 is selected from 1, 2, 3 or 4.

[0076] More preferably, Ar1 and Ar2 are independently selected from any one of the following groups:

[0077]

[0078] The n1 is selected from 1, 2, 3, 4 or 5; the n2 is selected from 1, 2, 3 or 4; the n3 is selected from 1, 2 or 3; the n4 is selected from 1 or 2; the n5 is selected from 1, 2, 3, 4, 5, 6 or 7; and the n6 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0079] More preferably, Ar1 and Ar2 are independently selected from any one of the following groups:

[0080]

[0081]

[0082]

[0083] The R mThe substituents are selected from one or more of the following groups, whether identical or different from each other: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, and naphthyl, and the substituents in the "substituted or unsubstituted" group are selected from one or more of the following groups: deuterium, cyano, fluorine, trifluoromethyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, and naphthyl. In the case of substitution by multiple substituents, the multiple substituents are identical or different from each other.

[0084] The n0 is selected from 1; the n1 is selected from 1, 2, 3, 4, or 5; the n2 is selected from 1, 2, 3, or 4; the n3 is selected from 1, 2, or 3; the n4 is selected from 1 or 2; the n5 is selected from 1, 2, 3, 4, 5, 6, or 7; the n6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the n7 is selected from 1, 2, 3, 4, 5, or 6; the n8 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; the n9 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; n 10 Choose from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11.

[0085] Preferably, the R of the present invention v R w The substituent is independently selected from one or more of the following groups, which are of formula A, hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, tetrahydronaphthyl, dihydronaphthyl, indene, indene; wherein the substituent in "substituted or unsubstituted" is selected from one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl.

[0086] Preferably, the R of the present invention nThe groups are identical or different from each other, selected from formula A, hydrogen, deuterium, tritium, cyano, fluorine, trifluoromethyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, tetrahydronaphthyl, dihydronaphthyl, indenyl, indenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, pyridyl, pyrimidinyl; wherein the substituents in "substituted or unsubstituted" are selected from one or more of deuterium, tritium, cyano, fluorine, trifluoromethyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, or optionally two adjacent R groups. n Groups can bond together to form substituted or unsubstituted benzene rings or substituted or unsubstituted five- or six-membered aliphatic rings; when substituted by multiple substituents, the substituents may be the same as or different from each other.

[0087] Preferably, the R of the present invention u Selected from the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphenyl, trimethylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriethylene, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazoyl, tetrahydronaphthyl, dihydronaphthyl, The substituent is selected from one of indanyl, indole, pyridyl, pyrazinyl, pyridazinyl, and triazinyl; wherein the substituent in "substituted or unsubstituted" is selected from one or more of deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, and deuterated naphthyl.

[0088] More preferably, the R u It is selected from one of methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphenyl, trimethylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, tetrahydronaphthyl, dihydronaphthyl, indanyl, indole, deuterated phenyl, deuterated biphenyl, and deuterated naphthyl.

[0089] In a preferred embodiment, R n At least one of them is selected from formula A.

[0090] Preferred, R n One, two, three or more selected from formula A.

[0091] More preferably, R n One or two of them are selected from formula A.

[0092] The optimal choice, R n One of them is selected from formula A.

[0093] Preferably, Ar1's R n One, two, or three of them are selected from formula A.

[0094] Preferably, the R of Ar2 n One, two, or three of them are selected from formula A.

[0095] Preferably, Ar1's R n One or two of them and Ar2's R n One, two, or any of the following groups are selected from formula A. Preferably, R is selected from hydrogen, deuterium, substituted or unsubstituted groups, including: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, adamantyl, norbornel, phenyl, pentadeuterated phenyl, deuterated naphthyl, tolyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, spirodifluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothiophene, and dibenzofuranyl.

[0096] More preferably, R is selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, adamantyl, norbornel, or one of the following groups:

[0097]

[0098] Preferably, the R a R b R c R dThey may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, adamantyl, norbornel, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenyl-naphthyl, acridine, spirodifluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, carbazole, 9-phenylcarbazole, pyrene, indole, acridine, pyridyl, furanyl, thiophene. Benzothiophene, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzothiophene, dibenzofuranyl, phenthiazinyl, phenoxazinyl, deuterated adamantyl, deuterated norbornel, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, deuterated terphenyl, deuterated anthracene, deuterated phenanthrene, deuterated triphenylene, deuterated phenyl-naphthyl, deuterated phenyl-deuterated naphthyl, phenyl-deuterated naphthyl, deuterated dibenzothiophene, deuterated dibenzofuranyl, deuterated 9,9-dimethylfluorenyl, or adjacent R a Adjacent R b Adjacent R c Adjacent R d They can be connected to form a ring structure.

[0099] Preferably, the R a R b R c R d They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, adamantyl, norbornel, or one of the following substituents:

[0100]

[0101]

[0102] Or adjacent R a Adjacent R b Adjacent R c Adjacent R d They can be linked together to form benzene rings or naphthalene rings.

[0103] Preferably, L0, L1, L2, L a Independently selected from single bonds or one of the following groups:

[0104]

[0105] The R rThey may be 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, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group;

[0106] 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.

[0107] The R x R y The group is independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, or substituted or unsubstituted of the following groups: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, anthracene, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazoyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, and indole;

[0108] The R z Selected from the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazoyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, and indanyl.

[0109] Preferably, the R r The group is selected from formula A, hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, and one or more of the following groups, substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, tetrahydronaphthyl, dihydronaphthyl, indanyl, indenyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, where, in the case of substitution by multiple substituents, the multiple substituents are the same as or different from each other.

[0110] More preferably, L0, L1, L2, L a Independently selected from a single bond or one of the following groups:

[0111]

[0112] Each H atom in the above groups is either unsubstituted or substituted by one or more D atoms, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, tetrahydronaphthyl, dihydronaphthyl, indanyl, indenyl, phenyl, biphenyl, terphenyl, and naphthyl.

[0113] More preferably, L1 and L2 are independently selected from single bonds or one of the following groups:

[0114]

[0115] More preferably, L0, L a Independently selected from single bonds or one of the following groups:

[0116]

[0117]

[0118] Preferably, the aromatic amine derivative contains one, two, three, four or more formulas A.

[0119] Preferably, the aromatic amine derivative contains one, two, three, or four formulas A.

[0120] Most preferably, the aromatic amine derivative is selected from any one of the following chemical structures:

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148] The method for preparing the aromatic amine derivatives of Formula I of the present invention can be achieved through conventional coupling reactions in the art, for example, through the following synthetic route, but the present invention is not limited thereto:

[0149]

[0150] The method for preparing the aromatic amine derivative of Formula I of the present invention firstly involves preparing intermediate A, i.e., amine compound a reacts with halogen compound b under a nitrogen atmosphere via a Buchwald reaction to obtain intermediate A; intermediate c then reacts with intermediate A via a Buchwald reaction, and the reaction is carried out under appropriate catalysts, organic bases, ligands, solutions, and temperatures to obtain the compound of Formula I, wherein X a X b It represents Cl, Br, or I.

[0151] This invention does not impose any particular restrictions on the source of the raw materials used in the above-described reactions; commercially available raw materials or preparation methods well known to those skilled in the art can be used. This invention also does not impose any particular restrictions on the above reactions; conventional reactions well known to those skilled in the art can be used. The compounds described in this invention have few synthetic steps and simple methods, which is beneficial for industrial production.

[0152] 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 aromatic amine derivatives described in the present invention.

[0153] Preferably, the organic layer includes a hole transport layer, which contains any one or a combination of at least two of the aromatic amine derivatives described in this invention.

[0154] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, wherein the first hole transport layer and / or the second hole transport layer contains any one or a combination of at least two of the aromatic amine derivatives described in this invention.

[0155] The light-emitting device of the present invention is typically formed on a substrate. The substrate can be any material that remains unchanged during the formation of electrodes and organic layers; for example, substrates made of glass, plastic, polymer films, silicon, etc. When the substrate is opaque, the electrodes opposite it are preferably transparent or translucent.

[0156] The anode material is preferably a material with a high work function, such as metals or alloys of vanadium, chromium, copper, zinc, gold, etc.; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but is not limited to these.

[0157] The cathode material is preferably a material with a low work function, such as metals or alloys thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; multilayered materials such as LiF / Al or LiO2 / Al, but is not limited to these.

[0158] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), 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 multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0159] In addition to the aromatic amine derivatives of the present invention, the material for the hole transport region may be small molecule materials such as aromatic amine derivatives, carbazole derivatives, stilbene derivatives, triphenyldiamine derivatives, styrene compounds, butadiene compounds, as well as polymer materials such as poly(p-phenylene) derivatives, polyaniline and its derivatives, polythiophene and its derivatives, polyvinylcarbazole and its derivatives, polysilane and its derivatives, but is not limited thereto. Preferably, the hole transport layer of the present invention is selected from N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (abbreviated as NPB), N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (abbreviated as α-NPD), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (abbreviated as TPD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (abbreviated as TAPC), 2,2,7,7-tetra(diphenylamino)-9,9-spirodifluorene (abbreviated as Spiro-TAD), etc. It can be a single structure composed of a single substance, or a single-layer structure or a multi-layer structure formed by different substances. More preferably, the hole transport layer is selected from any one or a combination of at least two of the aromatic amine derivatives described in the present invention. The material of the hole transport region may include the material of the first hole transport layer and / or the material of the second hole transport layer.

[0160] The hole injection layer is a layer in which holes from the electrode are injected. It can be made of metalporphyrin, oligothiophene, arylamine organic compounds, hexanitrile hexaazabenzophenanthrene organic compounds, quinacridone organic compounds, perylene organic compounds, anthraquinone, and conductive polymers such as polyaniline and polythiophene, but it is not limited to these.

[0161] The electron blocking layer material can be selected from N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (abbreviated as: α-NPD), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (abbreviated as: TDATA), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (abbreviated as: TPD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (abbreviated as: TAPC), 2,2,7,7-tetra(diphenylamino)-9,9-spirodifluorene (abbreviated as: Spiro-TAD), etc. It can be a single structure composed of a single substance, or a single-layer structure or a multi-layer structure formed by different substances.

[0162] 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; dipolystyrene compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzoazole, benzothiazole and benzimidazole compounds; spirocyclic compounds; polyfluorene, fluorene, etc., but is not limited to these.

[0163] The luminescent layer can comprise a host material and a dopant material. The host material can be an aromatic fused-ring derivative or a heterocyclic compound. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives and dibenzofuran derivatives, but are not limited to these.

[0164] Dopant materials include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include substituted or unsubstituted aromatic fused-ring derivatives of aryl amines, such as pyrene and anthracene; styrene amine compounds include styrene amines, styrene diamines, styrene triamines, and styrene tetraamines, but are not limited to these. Furthermore, metal complexes include iridium complexes and platinum complexes, but are not limited to these.

[0165] The emissive layer includes luminescent materials capable of emitting different wavelengths of light, and may also include the host material. The emissive layer can be a monochromatic emissive layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or they can be stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single colored emissive layer capable of simultaneously emitting different colors such as red, green, and blue.

[0166] Depending on the technology used, the light-emitting layer material can be various, including fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescence materials. An organic light-emitting device can employ a single light-emitting technology or a combination of different technologies. These different light-emitting materials, categorized by technology, can emit light of the same color or different colors.

[0167] The optimal doping ratio of the host material and guest material of the light-emitting layer can vary depending on the material used. Typically, 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%.

[0168] 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 single-layer electron transport layers containing only one compound and single-layer electron transport layers containing multiple compounds. Alternatively, the electron transport region can be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0169] The electron transport layer may include a first electron transport layer material and a second electron transport layer material. Commonly used electron transport materials are metal complexes of 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, bi-benzoquinone derivatives, 8-hydroxyquinoline and its derivatives. These can be single structures composed of a single substance, or single-layer or multi-layer structures formed by different substances.

[0170] An electron injection layer is located between the electron transport layer and the cathode. The electron injection layer may comprise 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 of alkali metals, alkaline earth metals, and rare earth metals (e.g., fluorides, chlorides, bromides, or iodides). 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. Alkali earth metal compounds may be selected from alkaline earth metal oxides (e.g., BaO, SrO, CaO). Rare earth metals can be selected from scandium (Sc), yttrium (Y), cerium (Ce), ytterbium (Yb), and gadolinium (Gd). Rare earth metal compounds can be selected from YbF3, ScF3, Sc2O3, Y2O3, and TbF3. They can be a single structure composed of a single substance, or a single-layer or multi-layer structure formed by different substances.

[0171] A hole blocking layer is a layer that prevents holes from reaching the cathode, and it can generally be formed using the same conditions as a hole injection layer. Specifically, it can be a diazole or triazole derivative, a phenanthrene-rholine derivative, BCP, an aluminum complex, etc., but is not limited to these.

[0172] The capping material of the present invention can be any one or a combination of at least two of Alq3, TPBi, or the aromatic amine derivatives described in the present invention. Preferably, the capping material of the present invention is selected from any one or a combination of at least two of the aromatic amine derivatives described in the present invention.

[0173] The organic light-emitting device of the present invention can be selected and combined according to the device parameter requirements and material characteristics, and some organic layers can be added or omitted. For example, an electron buffer layer can be added between the electron transport layer and the electron injection layer; organic layers with the same function can also be made into a stacked structure of two or more layers, for example, the electron transport layer can also have a first electron transport layer and a second electron transport layer.

[0174] The optimal thickness of the hole transport layer and electron transport layer varies depending on the materials used. It should be selected based on conditions that allow for appropriate driving voltage and luminous efficiency. However, it must be at least thick enough to avoid pinholes. Excessive thickness increases the driving voltage of the device, which is undesirable. Therefore, the thickness of the hole transport layer and electron transport layer is, for example, 1 nm to 1 μm, preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm.

[0175] The organic light-emitting device of the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0176] There are no particular limitations on the methods for preparing the layers in an organic light-emitting device. Any method can be employed, including vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slot coating, and dip coating. In this invention, vacuum evaporation is preferred. The compounds used as organic layers can be small organic molecules, large organic molecules, polymers, or combinations thereof.

[0177] The organic light-emitting device described in this invention can be widely used in panel displays, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photosensitive materials or organic thin-film transistors, signs, signal lights and other fields.

[0178] The invention is explained in more detail through the following examples, but is not intended to limit the invention. Based on this description, those skilled in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the entire scope disclosed without inventive effort.

[0179] Preparation and characterization of compounds

[0180] Description of raw materials, reagents, and characterization equipment:

[0181] The present invention does not impose any particular restrictions on the source of raw materials used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0182] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0183] Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0184] Synthesis Example 1: Preparation of Compound 5

[0185]

[0186] Preparation of intermediate A-5:

[0187] Under nitrogen protection, a-5 (12.07 g, 50.00 mmol), b-5 (11.66 g, 50.00 mmol), and sodium tert-butoxide (7.21 g, 75.00 mmol) were dissolved in 400 mL of toluene. Pd(OAc)₂ (0.11 g, 0.50 mmol) and P(t-Bu)₃ (2.00 mL, 1.00 mmol, 0.5 M toluene solution) were added with stirring. The mixture of the above reactants was heated under reflux for 5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography with n-hexane / dichloromethane (9:1 v / v) to give intermediate A-5 (14.76 g, 75%), with a solid purity ≥99.80% as determined by HPLC. Mass spectrometry m / z: 393.1922 (theoretical value: 393.1913).

[0188] Preparation of compound 5:

[0189] Under nitrogen protection, intermediates A-5 (11.81 g, 30.00 mmol), C-5 (17.82 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) were dissolved in 250 mL of toluene. Pd₂(dba)₃ (0.27 g, 0.30 mmol) and BINAP (0.39 g, 0.60 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 5.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene gave compound 5 (19.98 g, 70%), with a solid purity ≥ 99.96% as determined by HPLC. Mass spectrometry m / z: 950.4043 (theoretical value: 950.4056). Theoretical elemental content (%) C70 H 54 N₂Si: C, 88.38; H, 5.72; N, 2.94. Measured elemental content (%): C, 88.41; H, 5.68; N, 2.91.

[0190] Synthesis Example 2: Preparation of Compound 15

[0191]

[0192] Following the same preparation method as in Synthesis Example 1, b-5 was replaced with an equimolar amount of b-15 to obtain compound 15 (20.59 g, 68%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 1008.4830 (theoretical value: 1008.4839). Theoretical elemental content (%) C 74 H 64 N₂Si: C, 88.05; H, 6.39; N, 2.78. Measured elemental content (%): C, 88.01; H, 6.42; N, 2.82.

[0193] Synthesis Example 3: Preparation of Compound 27

[0194]

[0195] Following the same preparation method as in Synthesis Example 1, b-5 was replaced with an equimolar amount of b-27 to obtain compound 27 (19.84 g, 71%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 930.4380 (theoretical value: 930.4369). Theoretical elemental content (%) C 68 H 58 N₂Si: C, 87.70; H, 6.28; N, 3.01. Measured elemental content (%): C, 87.66; H, 6.32; N, 3.04.

[0196] Synthesis Example 4: Preparation of Compound 53

[0197]

[0198] Following the same preparation method as in Synthesis Example 1, a-5 and b-5 were replaced with equimolar amounts of a-53 and b-53, respectively, to obtain compound 53 (19.69 g, 69%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 950.4041 (theoretical value: 950.4056). Theoretical elemental content (%) C 70 H 54 N₂Si: C, 88.38; H, 5.72; N, 2.94. Measured elemental content (%): C, 88.40; H, 5.68; N, 2.97.

[0199] Synthesis Example 5: Preparation of Compound 59

[0200]

[0201] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-53, b-59, and c-59, respectively, to obtain compound 59 (18.13 g, 70%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 862.3763 ​​(theoretical value: 862.3743). Theoretical elemental content (%) C 63 H 50 N₂Si: C, 87.66; H, 5.84; N, 3.25. Measured elemental content (%): C, 87.70; H, 5.81; N, 3.20.

[0202] Synthesis Example 6: Preparation of Compound 63

[0203]

[0204] Following the same preparation method as in Synthesis Example 1, a-5 and b-5 were replaced with equimolar amounts of a-53 and b-63, respectively, to obtain compound 63 (18.88 g, 68%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 924.3914 (theoretical value: 924.3900). Theoretical elemental content (%) C 68 H 52 N₂Si: C, 88.27; H, 5.66; N, 3.03. Measured elemental content (%): C, 88.30; H, 5.62; N, 3.05.

[0205] Synthesis Example 7: Preparation of Compound 86

[0206]

[0207] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-53, b-86, and c-86, respectively, to obtain compound 86 (18.60 g, 71%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 872.3579 (theoretical value: 872.3587). Theoretical elemental content (%) C 64 H 48 N₂Si: C, 88.03; H, 5.54; N, 3.21. Measured elemental content (%): C, 88.08; H, 5.50; N, 3.18.

[0208] Synthesis Example 8: Preparation of Compound 93

[0209]

[0210] Following the same preparation method as in Synthesis Example 1, b-5 and c-5 were replaced with equimolar amounts of b-93 and c-93, respectively, to obtain compound 93 (19.93 g, 67%). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 990.4352 (theoretical value: 990.4369). Theoretical elemental content (%) C 73 H 58 N₂Si: C, 88.44; H, 5.90; N, 2.83. Measured elemental content (%): C, 88.40; H, 5.88; N, 2.79.

[0211] Synthesis Example 9: Preparation of Compound 127

[0212]

[0213] Following the same preparation method as in Synthesis Example 1, a-5 and b-5 were replaced with equimolar amounts of a-53 and b-127, respectively, to obtain compound 127 (19.01 g, 72%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 879.4071 (theoretical value: 879.4057). Theoretical elemental content (%) C 64 H 45 D5N2Si: C, 87.33; H, 6.30; N, 3.18. Measured elemental content (%): C, 87.35; H, 6.27; N, 3.22.

[0214] Synthetic Example 10: Preparation of Compound 136

[0215]

[0216] Following the same preparation method as in Synthesis Example 1, a-5 and b-5 were replaced with equimolar amounts of a-136 and b-136, respectively, to obtain compound 136 (19.22 g, 69%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 927.4402 (theoretical value: 927.4421). Theoretical elemental content (%) C 65 H 49 D7N2Si2: C, 84.09; H, 6.84; N, 3.02. Measured elemental content (%): C, 84.12; H, 6.80; N, 3.07.

[0217] Synthetic Example 11: Preparation of Compound 140

[0218]

[0219] Following the same preparation method as in Synthesis Example 1, b-5 was replaced with an equimolar amount of b-140 to obtain compound 140 (19.49 g, 68%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 954.4317 (theoretical value: 954.4307). Theoretical elemental content (%) C 70 H 50 D4N2Si: C, 88.01; H, 6.12; N, 2.93. Measured elemental content (%): C, 88.05; H, 6.09; N, 2.91.

[0220] Synthesis Example 12: Preparation of Compound 167

[0221]

[0222] Following the same preparation method as in Synthesis Example 1, a-5 and b-5 were replaced with equimolar amounts of a-53 and b-167, respectively, to obtain compound 167 (19.63 g, 66%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 990.4353 (theoretical value: 990.4369). Theoretical elemental content (%) C 73 H 58 N₂Si: C, 88.44; H, 5.90; N, 2.83. Measured elemental content (%): C, 88.46; H, 5.87; N, 2.88.

[0223] Synthetic Example 13: Preparation of Compound 170

[0224]

[0225] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-170, b-170, and c-170, respectively, to obtain compound 170 (18.40 g, 67%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 914.4068 (theoretical value: 914.4056). Theoretical elemental content (%) C 67 H 54 N₂Si: C, 87.92; H, 5.95; N, 3.06. Measured elemental content (%): C, 87.89; H, 5.90; N, 3.08.

[0226] Synthetic Example 14: Preparation of Compound 171

[0227]

[0228] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-53, b-170, and c-171, respectively, to obtain compound 171 (18.53 g, 64%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 964.4231 (theoretical value: 964.4213). Theoretical elemental content (%) C 71 H 56 N₂Si: C, 88.34; H, 5.85; N, 2.90. Measured elemental content (%): C, 88.30; H, 5.87; N, 2.86.

[0229] Synthetic Example 15: Preparation of Compound 185

[0230]

[0231] Following the same preparation method as in Synthesis Example 1, a-5 and b-5 were replaced with equimolar amounts of a-53 and b-185, respectively, to obtain compound 185 (20.58 g, 66%). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 1038.4359 (theoretical value: 1038.4369). Theoretical elemental content (%) C 77 H 58 N₂Si: C, 88.98; H, 5.62; N, 2.70. Measured elemental content (%): C, 88.93; H, 5.59; N, 2.66.

[0232] Synthesis Example 16: Preparation of Compound 219

[0233]

[0234] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-53, b-219, and c-219, respectively, to obtain compound 219 (20.18 g, 63%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1066.4662 (theoretical value: 1066.4682). Theoretical elemental content (%) C 79 H 62 N₂Si: C, 88.89; H, 5.85; N, 2.62. Measured elemental content (%): C, 88.93; H, 5.80; N, 2.58.

[0235] Synthesis Example 17: Preparation of Compound 232

[0236]

[0237] Following the same preparation method as in Synthesis Example 1, b-5 was replaced with an equimolar amount of b-232 to obtain compound 232 (19.69 g, 68%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 964.3864 (theoretical value: 964.3849). Theoretical elemental content (%) C 70 H 52 N₂OSi: C, 87.10; H, 5.43; N, 2.90. Measured elemental content (%): C, 87.07; H, 5.48; N, 2.86.

[0238] Synthesis Example 18: Preparation of Compound 253

[0239]

[0240] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-53, b-253, and c-253, respectively, to obtain compound 253 (20.07 g, 65%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 1028.3787 (theoretical value: 1028.3798). Theoretical elemental content (%) C 74 H 52 N2O2Si: C, 86.35; H, 5.09; N, 2.72. Measured elemental content (%): C, 86.30; H, 5.11; N, 2.75.

[0241] Synthesis Example 19: Preparation of Compound 262

[0242]

[0243] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-262, b-262, and c-262, respectively, to obtain compound 262 (20.06 g, 66%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 1012.3833 (theoretical value: 1012.3849). Theoretical elemental content (%) C 74 H 52 N₂OSi: C, 87.71; H, 5.17; N, 2.76. Measured elemental content (%): C, 87.68; H, 5.21; N, 2.80.

[0244] Synthesis Example 20: Preparation of Compound 299

[0245]

[0246] Following the same preparation method as in Synthesis Example 1, a-5 and b-5 were replaced with equimolar amounts of a-53 and b-299, respectively, to obtain compound 299 (19.49 g, 68%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 954.3476 (theoretical value: 954.3464). Theoretical elemental content (%) C 68 H 50 N₂SSi: C, 85.50; H, 5.28; N, 2.93. Measured elemental content (%): C, 85.47; H, 5.32; N, 2.97.

[0247] Synthesis Example 21: Preparation of Compound 314

[0248]

[0249] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-314, b-314, and c-314, respectively, to obtain compound 314 (20.30 g, 62%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 1090.3785 (theoretical value: 1090.3777). Theoretical elemental content (%) C 79 H 54 N₂SSi: C, 86.94; H, 4.99; N, 2.57. Measured elemental content (%): C, 86.90; H, 4.96; N, 2.62.

[0250] Synthesis Example 22: Preparation of Compound 355

[0251]

[0252] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-53, b-355, and c-355, respectively, to obtain compound 355 (20.60 g, 66%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1039.4310 (theoretical value: 1039.4322). Theoretical elemental content (%) C 76 H 57 N3Si: C, 87.74; H, 5.52; N, 4.04. Measured elemental content (%): C, 87.72; H, 5.48; N, 4.07.

[0253] Synthesis Example 23: Preparation of Compound 393

[0254]

[0255] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-53, b-393, and c-393, respectively, to obtain compound 393 (19.93 g, 67%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 990.4023 (theoretical value: 990.4005). Theoretical elemental content (%) C 72 H 54 N₂OSi: C, 87.24; H, 5.49; N, 2.83. Measured elemental content (%): C, 87.26; H, 5.53; N, 2.79.

[0256] Synthesis Example 24: Preparation of Compound 410

[0257]

[0258] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-410, b-410, and c-170, respectively, to obtain compound 410 (19.33 g, 65%). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 990.4015 (theoretical value: 990.4005). Theoretical elemental content (%) C 72 H 54 N₂OSi: C, 87.24; H, 5.49; N, 2.83. Measured elemental content (%): C, 87.20; H, 5.52; N, 2.86.

[0259] Synthesis Example 25: Preparation of Compound 434

[0260]

[0261] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-434, b-434, and c-434, respectively, to obtain compound 434 (19.36 g, 64%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 1007.4255 (theoretical value: 1007.4271). Theoretical elemental content (%) C 72 H 57 N3OSi: C, 85.76; H, 5.70; N, 4.17. Measured elemental content (%): C, 85.80; H, 5.67; N, 4.21.

[0262] Synthesis Example 26: Preparation of Compound 476

[0263]

[0264] Following the same preparation method as in Synthesis Example 1, b-5 was replaced with an equimolar amount of b-476 to obtain compound 476 (20.25 g, 67%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 1006.3768 (theoretical value: 1006.3777). Theoretical elemental content (%) C 72 H 54 N₂SSi: C, 85.85; H, 5.40; N, 2.78. Measured elemental content (%): C, 85.83; H, 5.36; N, 2.81.

[0265] Synthesis Example 27: Preparation of Compound 512

[0266]

[0267] Following the same preparation method as in Synthesis Example 1, a-5 and b-5 were replaced with equimolar amounts of a-53 and b-512, respectively, to obtain compound 512 (18.97 g, 69%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 915.3658 (theoretical value: 915.3645). Theoretical elemental content (%) C 65 H 49 N3OSi: C, 85.21; H, 5.39; N, 4.59. Measured elemental content (%): C, 85.18; H, 5.43; N, 4.61.

[0268] Synthesis Example 28: Preparation of Compound 522

[0269]

[0270] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-53, b-522, and c-522, respectively, to obtain compound 522 (17.34 g, 71%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 813.3529 (theoretical value: 813.3539). Theoretical elemental content (%) C 58 H 47 N3Si: C, 85.57; H, 5.82; N, 5.16. Measured elemental content (%): C, 85.60; H, 5.78; N, 5.20.

[0271] Synthesis Example 29: Preparation of Compound 555

[0272]

[0273] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-555, b-555, and c-555, respectively, to obtain compound 555 (17.64 g, 70%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 839.3566 (theoretical value: 839.3583). Theoretical elemental content (%) C 61 H 49 NOSi: C, 87.21; H, 5.88; N, 1.67. Measured elemental content (%): C, 87.19; H, 5.92; N, 1.70.

[0274] Synthesis Example 30: Preparation of Compound 571

[0275]

[0276] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-571, b-571, and c-555, respectively, to obtain compound 571 (20.25 g, 64%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1053.5316 (theoretical value: 1053.5305). Theoretical elemental content (%) C 77 H 71 NOSi: C, 87.70; H, 6.79; N, 1.33. Measured elemental content (%): C, 87.67; H, 6.83; N, 1.29.

[0277] Synthesis Example 31: Preparation of Compound 573

[0278]

[0279] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-53, b-573, and c-573, respectively, to obtain compound 573 (19.10 g, 68%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 935.3573 (theoretical value: 935.3583). Theoretical elemental content (%) C 69 H 49 NOSi: C, 88.52; H, 5.28; N, 1.50. Measured elemental content (%): C, 88.56; H, 5.30; N, 1.46.

[0280] Synthesis Example 32: Preparation of Compound 590

[0281]

[0282] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-53, b-590, and c-555, respectively, to obtain compound 590 (18.94 g, 66%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 955.4223 (theoretical value: 955.4209). Theoretical elemental content (%) C 70 H 57 NOSi: C, 87.92; H, 6.01; N, 1.46. Measured elemental content (%): C, 87.88; H, 6.03; N, 1.51.

[0283] Synthesis Example 33: Preparation of Compound 602

[0284]

[0285] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-53, b-602, and c-602, respectively, to obtain compound 602 (19.08 g, 65%). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 977.4948 (theoretical value: 977.4930). Theoretical elemental content (%) C 71 H 59 D4NOSi: C, 87.16; H, 6.90; N, 1.43. Measured elemental content (%): C, 87.20; H, 6.88; N, 1.47.

[0286] Synthesis Example 34: Preparation of Compound 628

[0287]

[0288] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-571, b-628, and c-555, respectively, to obtain compound 628 (18.06 g, 67%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 897.4224 (theoretical value: 897.4211). Theoretical elemental content (%) C 65 H 39 D 10 NOSi: C, 86.91; H, 6.62; N, 1.56. Measured elemental content (%): C, 86.88; H, 6.66; N, 1.51.

[0289] Synthesis Example 35: Preparation of Compound 715

[0290]

[0291] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-715, b-715, and c-715, respectively, to obtain compound 715 (16.68 g, 70%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 793.3632 (theoretical value: 793.3647). Theoretical elemental content (%) C 57 H 39 D6NOSi: C, 86.21; H, 6.47; N, 1.76. Measured elemental content (%): C, 86.16; H, 6.50; N, 1.78.

[0292] Synthesis Example 36: Preparation of Compound 884

[0293]

[0294] Following the same preparation method as in Synthesis Example 1, b-5 and c-5 were replaced with equimolar amounts of b-884 and c-884, respectively, to obtain compound 884 (18.76 g, 69%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 905.3140 (theoretical value: 905.3148). Theoretical elemental content (%) C 64 H 47 NOSSi: C, 84.82; H, 5.23; N, 1.55. Measured elemental content (%): C, 84.78; H, 5.25; N, 1.60.

[0295] Synthesis Example 37: Preparation of Compound 909

[0296]

[0297] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-909, b-909, and c-884, respectively, to obtain compound 909 (18.20 g, 67%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 904.3319 (theoretical value: 904.3307). Theoretical elemental content (%) C 64 H 48 N₂SSi: C, 84.92; H, 5.34; N, 3.09. Measured elemental content (%): C, 84.88; H, 5.30; N, 3.12.

[0298] Synthesis Example 38: Preparation of Compound 928

[0299]

[0300] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-928, b-928, and c-928, respectively, to obtain compound 928 (17.22 g, 68%). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 843.3275 (theoretical value: 843.3293). Theoretical elemental content (%) C 60 H 41 D4NSSi: C, 85.37; H, 5.85; N, 1.66. Measured elemental content (%): C, 85.33; H, 5.87; N, 1.70.

[0301] Synthesis Example 39: Preparation of Compound 934

[0302]

[0303] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-934, b-934, and c-884, respectively, to obtain compound 934 (16.49 g, 70%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 784.3368 (theoretical value: 784.3356). Theoretical elemental content (%) C 55 H 40 D5NSSi: C, 84.14; H, 6.42; N, 1.78. Measured elemental content (%): C, 84.18; H, 6.39; N, 1.80.

[0304] Synthesis Example 40: Preparation of Compound 967

[0305]

[0306] Following the same preparation method as in Synthesis Example 1, a-5, b-5, and c-5 were replaced with equimolar amounts of a-53, b-967, and c-967, respectively, to obtain compound 967 (18.66 g, 67%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 927.3879 (theoretical value: 927.3896). Theoretical elemental content (%) C 68 H 53 NOSi: C, 87.99; H, 5.76; N, 1.51. Measured elemental content (%): C, 87.94; H, 5.80; N, 1.48.

[0307] Red organic light-emitting device (hole transport layer)

[0308] [Comparative Examples 1-2] Device Fabrication Examples:

[0309] Comparative Example 1: Fabrication of organic light-emitting devices using vacuum thermal evaporation. The experimental steps were as follows: the ITO substrate was washed three times in distilled water, ultrasonically washed for 15 minutes, and after the distilled water washing was completed, it was ultrasonically washed in sequence with solvents such as isopropanol, acetone, and methanol, dried at 120°C, and then sent to the evaporation machine.

[0310] On a prepared ITO transparent substrate electrode, a hole injection layer HAT-CN / 29nm, a hole transport layer HT2-1 / 100nm, a bulk m-CBP:doped Ir(dmpq)2acac (97%:3% mass ratio) / 26nm were deposited by vacuum evaporation. Then, an electron transport layer TMPYPB and Liq (doping ratio 1:1 mass ratio) / 28nm, an electron injection layer LiF / 1nm, and a cathode Al / 125nm were deposited. The device was then sealed in a glove box, thus fabricating an organic light-emitting device. After completing the fabrication of the organic light-emitting device according to the above steps, the photoelectric performance of the device was measured. The molecular structures of the relevant materials are shown below:

[0311]

[0312] Comparative Example 2: The hole transport layer material HT2-1 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 in Comparative Example 1.

[0313] [Examples 1-40]

[0314] Examples 1-40: The hole transport layer material HT2-1 of the organic light-emitting device was replaced sequentially with compounds 5, 15, 27, 53, 59, 63, 86, 93, 127, 136, 140, 167, 170, 171, 185, 219, 232, 253, 262, 299, 314, 355, 393, 410, 434, 476, 512, 522, 555, 571, 573, 590, 602, 628, 715, 884, 909, 928, 934, and 967 of the present invention. All other steps were the same as in Comparative Example 1.

[0315] A combined IVL testing system was used to test the luminous efficiency of organic light-emitting devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, and the temperature was room temperature. The luminous characteristic test results of the obtained OLEDs are shown in Table 1. Table 1 presents the luminous characteristic test results of the OLEDs prepared by the compounds in the embodiments of this invention and the comparative materials.

[0316] [Table 1] Testing of the luminescent properties of light-emitting devices

[0317]

[0318]

[0319] Note: T97 refers to a current density of 10 mA / cm². 2 Under these conditions, the time it takes for the device's brightness to decay to 97%;

[0320] As can be seen from the results in Table 1, the aromatic amine derivatives of the present invention, when used as hole transport layer materials in organic light-emitting devices, exhibit the advantage of high luminous efficiency compared with comparative examples 1-2, and are high-performance hole transport materials for organic light-emitting devices.

[0321] Green organic light-emitting devices (second hole transport layer)

[0322] [Comparative Examples 3-4] Device Fabrication Examples:

[0323] Comparative Example 3: Fabrication of organic light-emitting devices using vacuum thermal evaporation. The experimental steps were as follows: the ITO transparent substrate was washed three times in distilled water, ultrasonically washed for 15 minutes, and after the distilled water washing was completed, it was ultrasonically washed in sequence with solvents such as isopropanol, acetone, and methanol, then dried at 120°C and sent to the evaporation machine.

[0324] On a prepared ITO transparent substrate electrode, a hole injection layer HAT-CN / 29nm, a first hole transport layer HT1 / 70nm, a second hole transport layer HT2-1 / 30nm, a bulk m-CBP:doped Ir(ppy)2acac (93%:7% mass ratio) / 27nm, an electron transport layer TMPYPB and Liq (doping ratio 1:1 mass ratio) / 28nm, an electron injection layer LiF / 1nm, and a cathode Al / 125nm were deposited by vacuum evaporation. The device was then sealed in a glove box to fabricate an organic light-emitting device. After completing the fabrication of the organic light-emitting device according to the above steps, the photoelectric performance of the device was measured. The molecular structure formulas of the relevant materials are shown below:

[0325]

[0326] Comparative Example 4: The second hole transport layer material HT2-1 in Comparative Example 3 was replaced with HT2-2, and the organic light-emitting device of Comparative Example 4 was manufactured in the same manner as in Comparative Example 3.

[0327] [Examples 41-78]

[0328] Implementation 41-78: The material of the second hole transport layer of the organic light-emitting device is replaced sequentially with compounds 5, 15, 27, 53, 59, 63, 86, 93, 127, 136, 140, 167, 170, 171, 185, 219, 232, 253, 262, 299, 314, 355, 393, 410, 476, 512, 555, 571, 573, 590, 602, 628, 715, 884, 909, 928, 934, and 967 of the present invention. All other steps are the same as in Comparative Example 3.

[0329] A combined IVL testing system was constructed using testing software, a computer, a K2400 digital source meter manufactured by Keithley, and a PR788 spectral scanning luminance meter manufactured by PhotoResearch, to test the luminous efficiency of organic light-emitting devices (OLEDs). The test results of the luminous characteristics of the OLEDs are shown in Table 2. Table 2 presents the luminous characteristic test results of the OLEDs prepared by the compounds prepared in the embodiments of this invention and the comparative materials.

[0330] [Table 2] Testing of the luminescent properties of light-emitting devices

[0331]

[0332]

[0333] Note: T97 refers to a current density of 10 mA / cm². 2 Under these conditions, the time it takes for the device's brightness to decay to 97%;

[0334] As can be seen from the results in Table 2, the aromatic amine derivatives of the present invention, when used as the second hole transport layer material in organic light-emitting devices, significantly improve the luminous efficiency and lifespan of organic light-emitting devices compared with comparative examples 3-4, and are high-performance organic light-emitting materials.

[0335] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. An aromatic amine derivative, characterized in that, The molecular structure is shown in Formula I: Wherein, X is selected from O, S or NR. e The R e Selected from one of the aryl groups of C6 to C14, whether substituted or unsubstituted; the term "substituted..." means monosubstituted or polysubstituted by a group independently selected from deuteryl or C1 to C6 alkyl. The Ar1 is selected from any one of the following groups: The Ar2 group is independently selected from any one of the following groups: The Y is selected from O or S; R in Ar1 n They are the same or different from each other, selected from formula A, hydrogen, deuterium; Ar1 R in n One or two of the R groups selected from the remaining groups of formula A and Ar1 n One of them is selected from formula A; R in Ar2 n They may be the same as or different from each other, and are selected from hydrogen, deuterium, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, adamantyl, phenyl; wherein the substituent in "substituted or unsubstituted" is selected from one or more of deuterium and tritium, or Choose any two adjacent R n Groups can bond together to form substituted or unsubstituted benzene rings; in the case of multiple substituents, the multiple substituents may be the same or different from each other; the "substituted..." in "substituted or unsubstituted benzene rings" refers to those that are monosubstituted or polysubstituted by a deuterium group; The R m They may be the same as or different from each other, selected from hydrogen, deuterium, or substituted or unsubstituted groups: methyl, in the case of being substituted by multiple substituents, the multiple substituents may be the same as or different from each other; the term "substituted..." refers to being mono- or poly-substituted by a deuterium group; The R v R w The substituent is independently selected from one of the following groups, either substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl; wherein the substituent in "substituted or unsubstituted" is selected from one or more of deuterium, methyl, isopropyl, and tert-butyl. The R u The substituent is selected from the following groups, either substituted or unsubstituted: phenyl, biphenyl, naphthyl; wherein the substituent in "substituted or unsubstituted" is selected from deuterium; The n1 is selected from 1, 2, 3, 4, or 5; the n2 is selected from 1, 2, 3, or 4; the n3 is selected from 1, 2, or 3; the n5 is selected from 1, 2, 3, 4, 5, 6, or 7; the n6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the n7 is selected from 1, 2, 3, 4, 5, or 6; the n8 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; and the n9 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. The R is selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, or one of the following groups: The L0, L a Independently selected from single bonds or one of the following groups: The L1 is selected from a single bond or one of the following groups: The L2 is selected from a single bond or one of the following groups: 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 R x R y The group is independently selected from the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl; the term "substituted..." refers to being mono- or poly-substituted by a deuterium group; The R r The same or different of one of the following groups, selected from hydrogen, deuterium, substituted or unsubstituted: methyl, in the case of being substituted by multiple substituents, the multiple substituents being the same or different from each other; the "substituted..." means being mono- or poly-substituted by a deuterium group; The R a R b R c R d They may be the same as or different from each other, and each is independently selected from one of hydrogen, deuterium, or adjacent R. a Adjacent R d They can be linked together to form a benzene ring; The value of 'a' is selected from 0, 1, 2, 3, or 4; the value of 'b' is selected from 0, 1, 2, 3, or 4. c is selected from 0, 1, 2, or 3; d is selected from 0, 1, 2, or 3; Equation A is: The same or different R1, R2, and R3 are selected from any one of substituted or unsubstituted C1-C6 alkyl groups or substituted or unsubstituted C6-C14 aryl groups; the term "substituted..." refers to a group that is monosubstituted or polysubstituted by a group independently selected from deuteryl or C1-C6 alkyl.

2. The aromatic amine derivative according to claim 1, characterized in that, Formula A is selected from one of the following groups:

3. The aromatic amine derivative according to claim 1, characterized in that, The Ar1 is selected from any one of the following groups: The Ar2 group is independently selected from any one of the following groups:

4. The aromatic amine derivative according to claim 1, characterized in that, The L0, L1, L2, L a Independently selected from single bonds or one of the following groups: The R r They may be the same or different from each other, and can be selected from either hydrogen or deuterium.

5. An aromatic amine derivative, characterized in that, The aromatic amine derivative is selected from any one of the following chemical structures:

6. 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, characterized in that, The organic layer contains any one or a combination of at least two of the aromatic amine derivatives described in any one of claims 1 to 5.

7. An organic light-emitting device according to claim 6, wherein the organic layer comprises a hole transport region, a light-emitting layer, an electron transport region, or a capping layer, characterized in that, The hole transport region contains any one or a combination of at least two of the aromatic amine derivatives according to any one of claims 1 to 5.

8. An organic light-emitting device according to claim 7, characterized in that, The hole transport region includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, wherein the hole transport layer contains any one or a combination of at least two of the aromatic amine derivatives according to any one of claims 1 to 5.

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