Arylamine-containing organic compound and application thereof

Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to an arylamine-containing organic compound and application thereof. The arylamine-containing organic compound provided by the invention can be used as a light-emitting auxiliary layer material to be applied to an organic electronic light-emitting device, so that the light-emitting efficiency of the device is improved, and the service life of the device is prolonged.

Description

Technical Field

[0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to an aromatic amine-containing organic compound and application thereof. Background Art

[0002] OLED (Organic Light-Emitting Diode) is an electroluminescent device. Its light-emitting principle is to use ITO transparent electrode and metal electrode as the anode and cathode of the device respectively. Under a certain voltage drive, electrons and holes are injected and migrated from the cathode and anode to the light-emitting layer respectively, and meet in the light-emitting layer to form a light-emitting phenomenon. OLED is mainly composed of a layered structure such as a light-emitting layer, an electron / hole injection layer, and an electron / hole transport layer. OLED is called the third generation display technology. Because of its characteristics of being lighter, thinner, more flexible, low energy consumption, high brightness, high contrast, wide viewing angle and good luminous efficiency, OLED technology is widely used in today's televisions, monitors, mobile phones, tablets and other fields.

[0003] Hole transport materials (HTMs) are functional layer materials in OLED devices, and their main function is to transport holes. Usually, electrons transferred from the electron transport layer to the light-emitting layer and holes transferred from the hole transport layer to the light-emitting layer combine in the light-emitting layer to form excitons. However, in the current device structure, the excitons generated in the light-emitting layer will be transferred to the hole transport layer, resulting in a charge imbalance in the light-emitting layer. Therefore, light emission will occur in the hole transport layer or at the interface of the hole transport layer, which reduces the color purity, efficiency and life of the organic electroluminescent device.

[0004] Therefore, in order to solve the above problems, a luminescent auxiliary layer is usually added between the hole transport layer and the light-emitting layer (i.e., a multi-layer hole transport layer is provided) to improve the life and efficiency of the device. The luminescent auxiliary layer can reduce the potential barrier between the hole transport layer and the light-emitting layer, reduce the driving voltage of the organic electroluminescent device, and further increase the utilization rate of holes, thereby improving the luminous efficiency and life of the device and reducing the driving voltage. However, there are few functional materials that can form a luminescent auxiliary layer. Therefore, it is necessary to develop new materials for luminescent auxiliary layers to improve the efficiency and life of organic electronic components. Summary of the invention

[0005] Based on this, the purpose of the present invention is to provide a novel aromatic amine-containing organic compound, which can be used as a light-emitting auxiliary layer material in organic electronic devices to improve the efficiency and life of the devices.

[0006] The technical solution of the present invention is:

[0007] An aromatic amine-containing organic compound having a structure as shown in formula (I):

[0008]

[0009] in,

[0010] R1 and R2, at each occurrence, are independently selected from -H, -D, a straight chain alkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl group having 3 to 20 carbon atoms;

[0011] Ar1, Ar2, Ar3, Ar4 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 30 ring atoms;

[0012] L1 and L2 are independently selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms;

[0013] The term "substituted or unsubstituted" means that the defined group is unsubstituted or substituted by one or more substituents R, wherein each occurrence of R is independently selected from -D, -F, -Cl, -Br, -I, -CN, a straight-chain alkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl group having 3 to 20 carbon atoms, an aromatic group having 6 to 30 carbon atoms, a heteroaromatic group having 5 to 30 ring atoms, or a group formed by the above groups.

[0014] Correspondingly, the present invention also provides a luminescent auxiliary layer material, wherein the luminescent auxiliary layer material is selected from the aromatic amine-containing organic compounds as described above.

[0015] Correspondingly, the present invention also provides an organic electronic device, comprising a cathode, an anode and at least one functional layer located between the cathode and the anode, characterized in that: the at least one functional layer comprises the aromatic amine-containing organic compound as described above.

[0016] Compared with the prior art, the present invention has at least the following beneficial effects:

[0017] The aromatic amine-containing organic compound of the present invention is introduced into The steric hindrance and solubility of the molecule are improved, which on the one hand improves the film-forming property of the molecule, and on the other hand makes the organic compound have good transmission performance and charge balance adjustment performance, thereby improving the luminous efficiency of the device and extending the service life of the light-emitting element. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] Figure 1 This is a structural diagram of the organic electronic light-emitting device in device embodiment 1 of the present invention.

[0019] Among them, 101 is a substrate; 102 is an anode layer; 103 is a hole injection layer; 104 is a hole transport layer; 105 is a light-emitting auxiliary layer; 106 is a light-emitting layer; 107 is an electron transport layer; 108 is an electron injection layer; and 109 is a cathode layer. DETAILED DESCRIPTION

[0020] The embodiments described in the present invention are only a part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without making creative work belong to the scope of protection of the present application. In addition, it should be understood that the specific embodiments described herein are only used to illustrate and explain the present application, and are not used to limit the present application.

[0021] In the present application, unless otherwise stated, the directional words used, such as "upper" and "lower", generally refer to the upper and lower parts of the device in actual use or working state. In addition, in the description of the present application, the term "including" means "including but not limited to", the term "plurality" means "two or more", and the various embodiments of the present application may exist in the form of a range; it should be understood that the description in the form of a range is only for convenience and brevity, and should not be understood as a rigid limitation on the scope of the present application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single numerical values ​​within the range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the range, such as 1, 2, 3, 4, 5 and 6.

[0022] The terms "and / or", "or / and", and "and / or" used in this article include any one of two or more related listed items, and also include any and all combinations of related listed items, and the arbitrary and all combinations include any two related listed items, any more related listed items, or a combination of all related listed items. It should be noted that when at least three items are connected by at least two conjunctions selected from "and / or", "or / and", and "and / or", it should be understood that in this application, the technical solution undoubtedly includes technical solutions that are all connected by "logical and", and undoubtedly includes technical solutions that are all connected by "logical or". For example, "A and / or B" includes three parallel solutions of A, B and A+B. For example, the technical solution of "A, and / or, B, and / or, C, and / or, D" includes any one of A, B, C, and D (that is, the technical solution that is all connected by "logical OR"), and also includes any and all combinations of A, B, C, and D, that is, the combination of any two or any three of A, B, C, and D, and also includes the combination of four of A, B, C, and D (that is, the technical solution that is all connected by "logical AND").

[0023] In the present invention, "substituted" means that one or more hydrogen atoms in a substituted group are replaced by a substituent.

[0024] In the present invention, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0025] In the present invention, the "number of ring atoms" refers to the number of atoms in the atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The same is true for the "number of ring atoms" described below unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0026] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aromatic group having 6 to 30 ring atoms" refers to an aromatic group containing 6 to 30 ring atoms, preferably a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, particularly preferably a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, and the aromatic group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, naphthyl, fluorenyl, dinaphthylenyl, acenaphthene and derivatives thereof. It is understandable that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0027] "Heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, and the non-carbon atom may be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 30 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 20 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 10 ring atoms, and the heteroaryl group is optionally further substituted, and suitable examples include, but are not limited to, thienyl, furanyl, pyrrolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, etc. and their derivatives.

[0028] In the present invention, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The carbon number of the linear alkyl group may be 1 to 30, 1 to 20, 1 to 10 or 1 to 6; the carbon number of the branched alkyl group may be 3 to 30, 3 to 20, 3 to 10 or 3 to 6; the carbon number of the cyclic alkyl group may be 3 to 30, 3 to 20, 3 to 10 or 3 to 6. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, and the like.

[0029] In the present invention, "*" connected to a single bond indicates a connection or fusion site;

[0030] In the present invention, when a linking site is not specified in a group, it means that any linking site in the group can be used as a linking site;

[0031] In the present invention, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other. The six Rs on the benzene ring may be the same as or different from each other.

[0032] In the present invention, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example R is connected to any substitutable position of the benzene ring.

[0033] The “combination thereof”, “any combination thereof”, “combination of groups”, “combination” and the like used in the present invention include all suitable combinations of any two or more items in the listed groups.

[0034] In the present invention, “further”, “furthermore”, “particularly”, etc. are used for descriptive purposes to indicate differences in content, but should not be construed as limiting the scope of protection of the present invention.

[0035] In the present invention, "optionally", "optional", and "optional" mean optional, that is, any one of the two parallel solutions of "yes" or "no". If multiple "options" appear in a technical solution, unless otherwise specified and there is no contradiction or mutual restriction, each "optional" is independent.

[0036] The first aspect of the present invention provides an aromatic amine-containing organic compound having a structure as shown in formula (I):

[0037]

[0038] Wherein: R1 and R2, each occurrence, are independently selected from -H, -D, a straight chain alkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl group having 3 to 20 carbon atoms;

[0039] Ar1, Ar2, Ar3, Ar4 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 30 ring atoms;

[0040] L1 and L2 are independently selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms;

[0041] The term "substituted or unsubstituted" means that the defined group is unsubstituted or substituted by one or more substituents R, wherein each occurrence of R is independently selected from -D, -F, -Cl, -Br, -I, -CN, a straight-chain alkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl group having 3 to 20 carbon atoms, an aromatic group having 6 to 30 carbon atoms, a heteroaromatic group having 5 to 30 ring atoms, or a group formed by the above groups.

[0042] Preferably, each occurrence of R is independently selected from -D, -F, -Cl, -Br, -I, -CN, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, an aromatic group having 6 to 20 carbon atoms, a heteroaromatic group having 5 to 20 ring atoms, or a group formed by the above groups.

[0043] In one embodiment, each occurrence of R1 and R2 is independently selected from -H, -D, a linear alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms.

[0044] In a more specific embodiment, each occurrence of R1 and R2 is independently selected from -H, -D, and methyl.

[0045] Furthermore, the Selected from the following groups:

[0046]

[0047] Wherein: * indicates the connection site.

[0048] In one embodiment, Ar1 and Ar2 are independently selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 20 ring atoms.

[0049] Furthermore, Ar1 and Ar2 are preferably of the following structure:

[0050]

[0051] Wherein: X is independently selected from CR3 or N at each occurrence;

[0052] Each occurrence of R3 is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, a straight chain alkyl group having 1-20 carbon atoms, a branched or cyclic alkyl group having 3-20 carbon atoms, an aromatic group having 6-30 carbon atoms, a heteroaromatic group having 5-30 ring atoms, or a group formed by the above groups;

[0053] # indicates a fusion site, which is selected from a C atom.

[0054] Furthermore, the aromatic amine-containing organic compound has a structure as shown in any one of formulas (II-1) to (II-6):

[0055]

[0056] Further, each occurrence of R3 is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, a straight-chain alkyl group having 1-10 carbon atoms, a branched or cyclic alkyl group having 3-10 carbon atoms, an aromatic group having 6-20 carbon atoms, a heteroaromatic group having 5-20 ring atoms, or a group formed by the above groups.

[0057] Furthermore, each occurrence of R3 is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, methyl, ethyl, isopropyl, propyl, butyl, tert-butyl, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, naphthyl, or a group formed by the above groups.

[0058] In one embodiment, the formula (II-1) is selected from the following structures:

[0059]

[0060] Wherein: R3 each time appears, is independently selected from -D, -F, -Cl, -Br, -I, -CN, methyl, ethyl, isopropyl, propyl, butyl, tert-butyl, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, naphthyl, or a group formed by the above groups.

[0061] In one embodiment, L1 and L2 are independently selected from a single bond, a substituted or unsubstituted aromatic group having 6-20 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5-20 ring atoms.

[0062] In a specific embodiment, L1 and L2 are independently selected from a single bond, a phenyl group substituted or unsubstituted by -D, a naphthyl group substituted or unsubstituted by -D, a phenanthrenyl group substituted or unsubstituted by -D, or a pyridyl group substituted or unsubstituted by -D.

[0063] In one embodiment, Ar3 and Ar4 are independently selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 20 ring atoms.

[0064] Furthermore, Ar3 and Ar4 are independently selected from the following groups:

[0065]

[0066] in:

[0067] Each occurrence of V is independently selected from C, CR4 or N;

[0068] Each occurrence of Y is independently selected from a single bond, CR5R6, O, S, N, NR7;

[0069] Each occurrence of R4, R5, R6, and R7 is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, a straight chain alkyl group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, an aromatic group having 6 to 30 carbon atoms, a heteroaromatic group having 5 to 30 ring atoms, or a group formed by the above groups;

[0070] When V is the attachment site, V is selected from C atoms; when Y is the attachment site, Y is selected from N.

[0071] In a preferred embodiment, each occurrence of R5 and R6 is independently selected from -H, -D, a straight chain alkyl group having 1 to 10 carbon atoms, a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic group having 6 to 10 carbon atoms.

[0072] Furthermore, each occurrence of R5 and R6 is independently selected from -H, -D, or methyl, or phenyl.

[0073] In one embodiment, each occurrence of R7 is independently selected from -H, -D, unsubstituted or replaced by R a Substituted phenyl, unsubstituted or replaced by R a substituted pyridyl, unsubstituted or replaced by Ra Substituted pyrimidinyl, unsubstituted or replaced by R a substituted naphthyl, or unsubstituted or replaced by R a Substituted phenanthroline; said R a Each occurrence is independently selected from -D, -F, -Cl, -Br, -I, -CN, a straight chain alkyl group having 1-10 carbon atoms, a branched or cyclic alkyl group having 3-10 carbon atoms, an aromatic group having 6-10 carbon atoms, a heteroaromatic group having 5-10 ring atoms, or a group formed by the above groups.

[0074] In a specific embodiment, the R a Each occurrence is independently selected from -D, -F, -Cl, -Br, -I, -CN, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, cyclohexyl, adamantyl, phenyl, biphenyl, naphthyl, quinolyl, isoquinolyl, phenanthrenyl, or a group formed by the above groups.

[0075] In one embodiment, each occurrence of R4 is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, a straight chain alkyl group having 1-10 carbon atoms, a branched or cyclic alkyl group having 3-10 carbon atoms, an aromatic group having 6-10 carbon atoms, a heteroaromatic group having 5-10 ring atoms, or a group formed by the above groups.

[0076] In a preferred embodiment, Ar3 and Ar4 are independently selected from the following groups:

[0077]

[0078]

[0079] in:

[0080] Each occurrence of R8 is independently selected from -D, -F, -Cl, -Br, -I, -CN, a straight chain alkyl group having 1-10 carbon atoms, a branched or cyclic alkyl group having 3-10 carbon atoms, an aromatic group having 6-10 carbon atoms, a heteroaromatic group having 5-10 ring atoms, or a group formed by the above groups;

[0081] Each occurrence of n1 is independently selected from 0, 1, 2, 3, 4 or 5;

[0082] n2, at each occurrence, is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0083] n3, at each occurrence, is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

[0084] Each occurrence of n4 is independently selected from 0, 1, 2, 3 or 4;

[0085] Each occurrence of n5 is independently selected from 0, 1, 2, 3, 4, 5 or 6.

[0086] Furthermore, each occurrence of R8 is independently selected from -D, -F, -Cl, -Br, -I, -CN, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or a phenyl group, or a group composed of the above groups.

[0087] In one embodiment, the aromatic amine-containing organic compound according to the present invention is selected from the following structures:

[0088]

[0089] Wherein: R3 each time appears, is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, methyl, ethyl, isopropyl, propyl, butyl, tert-butyl, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, naphthyl, or a group formed by the above groups.

[0090] Specifically, the aromatic amine-containing organic compound according to the present invention is selected from the following structures, but is not limited thereto:

[0091]

[0092]

[0093]

[0094] The present invention further relates to a luminescent auxiliary layer material, wherein the luminescent auxiliary layer material is selected from the aromatic amine-containing organic compounds as described above.

[0095] The present invention further relates to an organic electronic device, which comprises the aromatic amine-containing organic compound as described above. The organic electronic device according to the present invention can be selected from, but not limited to, organic light emitting diodes (OLEDs), organic photovoltaic cells, organic field effect transistors, organic lasers, organic spintronic devices, organic sensors and organic plasmon emitting diodes, etc., and is particularly preferably OLEDs.

[0096] Furthermore, the organic electronic device comprises an anode, a cathode, and at least one functional layer located between the anode and the cathode, and the at least one functional layer comprises the aromatic amine-containing organic compound as described above.

[0097] Optionally, the functional layer comprises a hole transport layer, a luminescence auxiliary layer and a luminescent layer, the hole transport layer is located between the anode and the luminescent layer, the luminescence auxiliary layer is located between the hole transport layer and the luminescent layer, and the luminescence auxiliary layer comprises the aromatic amine-containing organic compound as described above.

[0098] In a specific embodiment, the organic electronic device according to the present invention comprises an anode, a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, an electron transport layer, an electron injection layer and a cathode stacked in sequence from bottom to top; the luminescence auxiliary layer comprises the aromatic amine-containing organic compound as described above. Figure 1 described.

[0099] In some embodiments, the organic electronic device further comprises a substrate. The substrate may be located on the side of the anode away from the light-emitting layer, or may be located on the side of the cathode away from the light-emitting layer. The substrate may be opaque or transparent. The substrate may also be rigid or flexible, for example, the material of the substrate may be plastic, metal, semiconductor wafer or glass. Preferably, the substrate has a smooth surface, and a substrate without surface defects is a particularly ideal choice. In a preferred embodiment, the substrate is glass, polyethylene terephthalate (PET) or polyethylene glycol (2,6-naphthalene) (PEN).

[0100] The material of the anode can be an anode material known in the art for organic electronic devices, such as a conductive metal, a conductive metal oxide or a conductive polymer. As an example, the material of the anode can be selected from but not limited to at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO and aluminum-doped zinc oxide (AZO). Other suitable anode materials are known and can be easily selected and used by those of ordinary skill in the art.

[0101] The cathode material may be a cathode material known in the art for organic electronic devices, such as a conductive metal or a conductive metal oxide. As an example, the cathode material may be selected from but not limited to at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt and ITO. The cathode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0102] The hole injection layer has the functions of reducing the surface roughness of ITO, reducing internal defects of the device, and reducing the hole injection barrier. The material of the hole injection layer can be a material known in the art for a hole injection layer, for example, it can be selected from but not limited to HATCN, F4-TCQN, 1-TNATA, 2-TNATA, m-MTDATA, PEDOT:PSS, MoO3, AgO, etc.

[0103] The hole transport layer has the function of improving the transport efficiency of holes in the device and blocking electrons in the light-emitting layer. The material of the hole transport layer can be a hole transport layer material known in the art, for example, it can be selected from aromatic amine organic compounds, including but not limited to NPB, CBP, TFB, TCTA, TAPC, TPD, Spiro-TAD, etc.

[0104] The light-emitting layer may include a host material and a doping material. The host material is preferably selected from heterocyclic compounds and the like. Specifically, examples of the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, pyrimidine derivatives, triazine derivatives, etc., but are not limited thereto. The doping material may be selected from metal complex materials, preferably from Ir-based metal complexes. The weight doping ratio of the host material and the doping material may vary depending on the materials used, and the doping ratio of the doping material is usually 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

[0105] The electron transport layer can play a role in promoting electron transport. The electron transport material is a material that advantageously receives electrons from the cathode and transports the electrons to the light-emitting layer, and a material with high electron mobility is suitable. The electron transport layer can include a compound containing a heterocycle, such as a pyridine derivative, a pyrimidine derivative, a triazine derivative, and the like.

[0106] The electron injection layer serves to reduce the electron injection barrier between the cathode and the organic layer, so that electrons are effectively injected into the organic layer. The electron injection layer material includes but is not limited to the following materials, metals, metal compounds, metal oxides, etc. Specific examples may include lithium (Li), lithium fluoride (LiF), 8-hydroxyquinoline lithium (Liq), cesium fluoride (CsF), lithium oxide (Li2O), cesium carbonate (Cs2CO3), etc., but are not limited thereto.

[0107] The present invention also relates to an electronic device comprising the organic electronic device. The present invention relates to the application of the electroluminescent device in various electronic devices. The electronic device may be, but is not limited to, a display device, a lighting device, a light source, a sensor, etc.

[0108] The present invention will be specifically described below through specific examples. The following examples are only partial embodiments of the present invention and are not intended to limit the present invention. Specific embodiments

[0110] The present invention will be described below in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the attached claims summarize the scope of the present invention. Under the guidance of the concept of the present invention, those skilled in the art should be aware that certain changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

[0111] Here, the aromatic amine-containing organic compound and its application according to the present invention are exemplified, but the present invention is not limited to the following embodiments.

[0112] Synthesis Example 1: Synthesis of Compound (2)

[0113]

[0114] Synthesis of compound 1-1:

[0115] Accurately weigh carbazole (8.4g, 50.00mmol), compound 2,7-dibromo-9,10-dihydrophenanthrene (18.6g, 55mmol), 1,1-bis(diphenylphosphino)diphenylferropalladium dichloride (PdCl2(dppf), 366mg, 0.5mmol), sodium tert-butoxide (7.2g, 75mmol), add them to a 500mL three-necked flask, add 250mL toluene, replace nitrogen three times, add 7mL of tri-tert-butylphosphine (10% mass ratio), heat at 90℃ and react for 8h. After the reaction is completed, cool to room temperature, add water to quench the reaction, extract three times with dichloromethane, combine the organic phases, dry with anhydrous magnesium sulfate, concentrate in vacuo, slurry the residue with methanol, and filter, and finally obtain about 17.96g of compound 1-1, yield: 84.5%, MS: 425.18.

[0116] Synthesis of compound (2):

[0117] Accurately weigh compound 1-1 (1.4 g, 3.30 mmol), 1-2 (0.74 g, 3.00 mmol), 1,1-bis(diphenylphosphino)diferronichloridopalladium (PdCl2(dppf), 22 mg, 0.03 mmol), sodium tert-butoxide (432 mg, 4.50 mmol), add 0.5 mL of tri-tert-butylphosphine (10% mass ratio) and add them into a 100 mL three-necked flask, add 20 mL of toluene, replace nitrogen three times, heat at 90°C and react for 8 h. After the reaction is completed, cool to room temperature, add water to quench the reaction, extract with ethyl acetate three times, combine the organic phases, dry with anhydrous sodium sulfate, concentrate in vacuo, slurry the residue with methanol, and filter to finally obtain about 1.21 g of compound (2), with a yield of 68.4% and MS of 589.66.

[0118] Synthesis Example 2: Synthesis of Compound (16)

[0119]

[0120] Compound 1-1 (2.34 g, 5.50 mmol), compound 2-1 (1.81 g, 5.00 mmol), 1,1-bis(diphenylphosphino)diferronichloridopalladium (PdCl2(dppf), 36 mg, 0.05 mmol), sodium tert-butoxide (720 mg, 7.50 mmol) were accurately weighed and added to a 100 mL three-necked flask in sequence. 30 mL of toluene was added, nitrogen was replaced three times, 0.8 mL of tri-tert-butylphosphine (10% mass ratio) was added, and the mixture was heated at 90°C for 8 h. After the reaction was completed, the mixture was cooled to room temperature, water was added to quench the reaction, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate, and concentrated in vacuo. The residue was slurried with methanol and filtered to obtain about 2.13 g of compound (16) with a yield of 60.5% and MS of 704.54.

[0121] Synthesis Example 3: Synthesis of Compound (19)

[0122]

[0123] Compound 1-1 (2.34 g, 5.50 mmol), compound 3-1 (2.05 g, 5.00 mmol), 1,1-bis(diphenylphosphino)diferronichloridopalladium (PdCl2(dppf), 36 mg, 0.05 mmol), sodium tert-butoxide (720 mg, 7.50 mmol) were accurately weighed and added to a 100 mL three-necked flask in sequence. 30 mL of toluene was added, nitrogen was replaced three times, 0.8 mL of tri-tert-butylphosphine (10% mass ratio) was added, and the mixture was heated at 90°C for 8 h. After the reaction was completed, the mixture was cooled to room temperature, water was added to quench the reaction, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate, and concentrated in vacuo. The residue was slurried with methanol and filtered to obtain about 2.94 g of compound (19) with a yield of 78.0% and MS of 753.69.

[0124] Synthesis Example 4: Synthesis of Compound (23)

[0125]

[0126] Synthesis of compound 4-3:

[0127] Accurately weigh compound 4-1 (0.89 g, 5.50 mmol), compound 4-2 (1.25 g, 5.00 mmol), 1,1-bis(diphenylphosphine)diferronipalladium dichloride (PdCl2(dppf), 36 mg, 0.05 mmol), sodium tert-butoxide (720 mg, 7.50 mmol), add them to a 100 mL three-necked flask, add 30 mL toluene, replace nitrogen three times, add 0.8 mL of tri-tert-butylphosphine (10% mass ratio), heat at 90 ° C and react for 8 hours. After the reaction is completed, cool to room temperature, add water to quench the reaction, extract three times with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, concentrate in vacuo, slurry the residue with methanol, and filter to finally obtain about 1.22 g of compound 4-3, yield: 73.7%, MS: 330.98.

[0128] Synthesis of compound (23):

[0129] Compound 1-1 (1.40 g, 3.30 mmol), compound 4-3 (0.99 g, 3.00 mmol), 1,1-bis(diphenylphosphino)diferronichloridopalladium (PdCl2(dppf), 22 mg, 0.03 mmol), sodium tert-butoxide (432 mg, 4.50 mmol) were accurately weighed and added to a 100 mL three-necked flask in sequence. 20 mL of toluene was added, nitrogen was replaced three times, 0.5 mL of tri-tert-butylphosphine (mass ratio 10%) was added, and the mixture was heated at 90°C for 8 h. After the reaction was completed, the mixture was cooled to room temperature, water was added to quench the reaction, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate, and concentrated in vacuo. The residue was slurried with methanol and filtered to obtain about 1.15 g of compound (23) with a yield of 56.9% and MS of 673.52.

[0130] Synthesis Example 5: Synthesis of Compound (31)

[0131]

[0132] Compound 1-1 (2.34 g, 5.50 mmol), compound 5-1 (1.48 g, 5.00 mmol), 1,1-bis(diphenylphosphino)diferronichloridopalladium (PdCl2(dppf), 36 mg, 0.05 mmol), sodium tert-butoxide (720 mg, 7.50 mmol) were accurately weighed and added to a 100 mL three-necked flask in sequence. 30 mL of toluene was added, nitrogen was replaced three times, 0.8 mL of tri-tert-butylphosphine (mass ratio 10%) was added, and the mixture was heated at 90°C for 8 h. After the reaction was completed, the mixture was cooled to room temperature, water was added to quench the reaction, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate, and concentrated in vacuo. The residue was slurried with methanol and filtered to obtain about 2.34 g of compound (31), with a yield of 73.2% and MS of 639.44.

[0133] Synthesis Example 6: Synthesis of Compound (36)

[0134]

[0135] Compound 1-1 (2.34 g, 5.50 mmol), compound 6-1 (1.96 g, 5.00 mmol), 1,1-bis(diphenylphosphino)diferronichloridopalladium (PdCl2(dppf), 36 mg, 0.05 mmol), sodium tert-butoxide (720 mg, 7.50 mmol) were accurately weighed and added to a 100 mL three-necked flask in sequence. 30 mL of toluene was added, nitrogen was replaced three times, 0.8 mL of tri-tert-butylphosphine (mass ratio 10%) was added, and the mixture was heated at 90°C for 8 h. After the reaction was completed, the mixture was cooled to room temperature, water was added to quench the reaction, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate, and concentrated in vacuo. The residue was slurried with methanol and filtered to obtain about 2.32 g of compound (36) with a yield of 63.1% and MS of 735.62.

[0136] Synthesis Example 7 Synthesis of Compound (42):

[0137]

[0138] Synthesis of compound 7-3:

[0139] Accurately weigh compound 7-1 (1.40 g, 11.00 mmol), compound 7-2 (2.46 g, 10.00 mmol), tetrakistriphenylphosphine palladium (Pd(PPh3)4, 116 mg, 0.10 mmol), potassium carbonate (4.15 g, 30.00 mmol), add them to a 100 mL three-necked flask in sequence, add 60 mL of THF, replace nitrogen three times, and heat to reflux for 8 hours. After the reaction is completed, cool to room temperature, add water to quench the reaction, extract three times with dichloromethane, combine the organic phases, dry with anhydrous magnesium sulfate, concentrate in vacuo, recrystallize the residue with chloroform and ethyl acetate, and filter to finally obtain about 1.82 g of compound 7-3, yield: 73.2%, MS: 248.51.

[0140] Synthesis of compound 7-5:

[0141] Accurately weigh compound 7-4 (1.86g, 5.50mmol), 7-3 (1.24g, 5.00mmol), 1,1-bis(diphenylphosphine)diferronipalladium dichloride (PdCl2(dppf), 36mg, 0.05mmol), sodium tert-butoxide (720mg, 7.50mmol), add them to a 100mL three-necked flask, add 30mL toluene, replace nitrogen three times, add 0.8mL tri-tert-butylphosphine (10% mass ratio), heat to 90℃ for 8h. After the reaction is completed, cool to room temperature, add water to quench the reaction, extract three times with dichloromethane, combine the organic phases, dry with anhydrous magnesium sulfate, concentrate in vacuo, slurry the residue with methanol, and filter to finally obtain about 1.92g of compound 7-5, yield: 75.9%, MS: 506.19.

[0142] Synthesis of compound (42):

[0143] Compound 7-5 (1.67 g, 3.30 mmol), compound 1-2 (0.74 g, 3.00 mmol), 1,1-bis(diphenylphosphino)diferronichloridopalladium (PdCl2(dppf), 22 mg, 0.03 mmol), sodium tert-butoxide (432 mg, 4.50 mmol) were accurately weighed and added to a 100 mL three-necked flask in sequence, and 20 mL of toluene was added. The nitrogen was replaced three times, and 0.5 mL of tri-tert-butylphosphine (mass ratio 10%) was added. The mixture was heated at 90°C for 8 h. After the reaction was completed, the mixture was cooled to room temperature, water was added to quench the reaction, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate, and concentrated in vacuo. The residue was slurried with methanol and filtered to obtain about 1.28 g of compound (42) with a yield of 63.6% and MS of 670.46.

[0144] Synthesis Example 8: Synthesis of Compound (44)

[0145]

[0146] Synthesis of compound 8-2:

[0147] Accurately weigh compound 7-4 (3.72g, 11.00mmol), 8-1 (2.23g, 10.00mmol), 1,1-bis(diphenylphosphine)diferronipalladium dichloride (PdCl2(dppf), 72mg, 0.10mmol), sodium tert-butoxide (14.4mg, 15.00mmol), add to a 100mL three-necked flask, add 30mL toluene, replace nitrogen three times, add 1.6mL tri-tert-butylphosphine (10% mass ratio), heat to 90°C for 8h. After the reaction is completed, cool to room temperature, add water to quench the reaction, extract three times with dichloromethane, combine the organic phases, dry with anhydrous magnesium sulfate, concentrate in vacuo, slurry the residue with methanol, and filter to finally obtain about 3.30g of compound 8-2, yield: 68.6%, MS: 480.76.

[0148] Synthesis of compound (44):

[0149] Compound 8-2 (1.59 g, 3.30 mmol), 8-3 (0.90 g, 3.00 mmol), 1,1-bis(diphenylphosphino)diferronichloridopalladium (PdCl2(dppf), 22 mg, 0.03 mmol), sodium tert-butoxide (432 mg, 4.50 mmol) were accurately weighed and added to a 100 mL three-necked flask in sequence. 20 mL of toluene was added, nitrogen was replaced three times, 0.5 mL of tri-tert-butylphosphine (mass ratio 10%) was added, and the mixture was heated at 90°C for 8 h. After the reaction was completed, the mixture was cooled to room temperature, water was added to quench the reaction, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was slurried with methanol and filtered to obtain about 1.37 g of compound (44) with a yield of 65.1% and MS of 701.05.

[0150] Synthesis Example 9: Synthesis of Compound (56)

[0151]

[0152] Synthesis of compound 9-2:

[0153] Accurately weigh compound 7-4 (1.86g, 5.50mmol), compound 9-1 (1.25g, 5.00mmol), 1,1-bis(diphenylphosphine)diferronipalladium dichloride (PdCl2(dppf), 36mg, 0.05mmol), sodium tert-butoxide (720mg, 7.50mmol), add them to a 100mL three-necked flask, add 30mL toluene, replace nitrogen three times, add 0.8mL tri-tert-butylphosphine (10% mass ratio), heat to 90°C for 8h. After the reaction is completed, cool to room temperature, add water to quench the reaction, extract three times with dichloromethane, combine the organic phases, dry with anhydrous magnesium sulfate, concentrate in vacuo, slurry the residue with methanol, and filter to finally obtain about 1.94g of compound 9-2, with a yield of 76.5% and MS of 506.93.

[0154] Synthesis of compound (56):

[0155] Compound 9-2 (1.67 g, 3.30 mmol), compound 9-3 (0.78 g, 3.00 mmol), 1,1-bis(diphenylphosphino)diferronichloridopalladium (PdCl2(dppf), 22 mg, 0.03 mmol), sodium tert-butoxide (432 mg, 4.50 mmol) were accurately weighed and added to a 100 mL three-necked flask in sequence. 20 mL of toluene was added, nitrogen was replaced three times, 0.5 mL of tri-tert-butylphosphine (mass ratio 10%) was added, and the mixture was heated at 90°C for 8 h. After the reaction was completed, the mixture was cooled to room temperature, water was added to quench the reaction, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was slurried with methanol and filtered to obtain about 1.25 g of compound (56) with a yield of 60.8% and MS of 685.41.

[0156] Synthesis Example 10: Synthesis of Compound (60)

[0157]

[0158] Compound 8-2 (1.58 g, 3.30 mmol), compound 10-3 (1.23 g, 3.00 mmol), 1,1-bis(diphenylphosphino)diferronichloridopalladium (PdCl2(dppf), 22 mg, 0.03 mmol), sodium tert-butoxide (432 mg, 4.50 mmol) were accurately weighed and added to a 100 mL three-necked flask in sequence. 20 mL of toluene was added, nitrogen was replaced three times, 0.5 mL of tri-tert-butylphosphine (mass ratio 10%) was added, and the mixture was heated at 90°C for 8 h. After the reaction was completed, the mixture was cooled to room temperature, water was added to quench the reaction, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate, and concentrated in vacuo. The residue was slurried with methanol and filtered to obtain about 1.92 g of compound (60) with a yield of 79.0% and MS of 809.98.

[0159] Synthesis Example 11: Synthesis of Compound (62)

[0160]

[0161] Synthesis of compound 11-3:

[0162] Accurately weigh compound 11-2 (4.34 g, 11.00 mmol), compound 11-1 (3.62 g, 10.00 mmol), 1,1-bis(diphenylphosphine)diferronipalladium dichloride (PdCl2(dppf), 73 mg, 0.10 mmol), sodium tert-butoxide (1.44 g, 15.00 mmol), add them to a 100 mL three-necked flask, add 30 mL of toluene, replace nitrogen three times, add 1.6 mL of tri-tert-butylphosphine (10% mass ratio), and heat to 90 ° C for 8 h. After the reaction is completed, cool to room temperature, add water to quench the reaction, extract three times with dichloromethane, combine the organic phases, dry with anhydrous magnesium sulfate, concentrate in vacuo, slurry the residue with methanol, and filter to finally obtain about 4.84 g of compound 11-3, with a yield of 71.7% and MS of 675.29.

[0163] Synthesis of compound (62):

[0164] Compound 11-3 (2.23 g, 3.30 mmol), carbazole (0.50 g, 3.00 mmol), 1,1-bis(diphenylphosphino)diferronichloridopalladium (PdCl2(dppf), 22 mg, 0.03 mmol), sodium tert-butoxide (432 mg, 4.50 mmol) were accurately weighed and added to a 100 mL three-necked flask in sequence. 20 mL of toluene was added, nitrogen was replaced three times, 0.5 mL of tri-tert-butylphosphine (mass ratio 10%) was added, and the mixture was heated at 90°C for 8 h. After the reaction was completed, the mixture was cooled to room temperature, water was added to quench the reaction, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was slurried with methanol and filtered to obtain about 1.31 g of compound (62) with a yield of 57.4% and MS of 761.24.

[0165] Synthesis Example 12: Synthesis of Compound (66)

[0166]

[0167] Compound 11-3 (2.23 g, 3.30 mmol), compound 12-1 (0.73 g, 3.00 mmol), 1,1-bis(diphenylphosphino)diferronichloridopalladium (PdCl2(dppf), 22 mg, 0.03 mmol), sodium tert-butoxide (432 mg, 4.50 mmol) were accurately weighed and added to a 100 mL three-necked flask in sequence. 20 mL of toluene was added, nitrogen was replaced three times, 0.5 mL of tri-tert-butylphosphine (mass ratio 10%) was added, and the mixture was heated at 90°C for 8 h. After the reaction was completed, the mixture was cooled to room temperature, water was added to quench the reaction, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was slurried with methanol and filtered to obtain about 1.36 g of compound (66) with a yield of 54.1% and MS of 837.75.

[0168] Synthesis Example 13: Synthesis of Compound (77)

[0169]

[0170] Synthesis of compound 13-2:

[0171] Accurately weigh compound 7-4 (1.86g, 5.50mmol), compound 13-1 (1.09g, 5.00mmol), 1,1-bis(diphenylphosphine)diferronipalladium dichloride (PdCl2(dppf), 36mg, 0.05mmol), sodium tert-butoxide (720mg, 7.50mmol), add them to a 100mL three-necked flask, add 30mL toluene, replace nitrogen three times, add 0.8mL tri-tert-butylphosphine (10% mass ratio), heat to 90°C for 8h. After the reaction is completed, cool to room temperature, add water to quench the reaction, extract three times with dichloromethane, combine the organic phases, dry with anhydrous magnesium sulfate, concentrate in vacuo, slurry the residue with methanol, and filter to finally obtain about 1.89g of compound 13-2, with a yield of 79.6% and MS of 474.82.

[0172] Synthesis of compound (77):

[0173] Compound 13-2 (1.57 g, 3.30 mmol), compound 13-3 (0.93 g, 3.00 mmol), 1,1-bis(diphenylphosphino)diferronichloridopalladium (PdCl2(dppf), 22 mg, 0.03 mmol), sodium tert-butoxide (432 mg, 4.50 mmol) were accurately weighed and added to a 100 mL three-necked flask in sequence. 20 mL of toluene was added, nitrogen was replaced three times, 0.5 mL of tri-tert-butylphosphine (mass ratio 10%) was added, and the mixture was heated at 90°C for 8 h. After the reaction was completed, the mixture was cooled to room temperature, water was added to quench the reaction, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was slurried with methanol and filtered to obtain about 1.56 g of compound (77) with a yield of 74.0% and MS of 703.14.

[0174] Synthesis Example 14: Synthesis of Compound (89)

[0175]

[0176] Synthesis of compound 14-2:

[0177] Accurately weigh compound 7-4 (1.86g, 5.50mmol), compound 14-1 (1.09g, 5.00mmol), 1,1-bis(diphenylphosphine)diferronipalladium dichloride (PdCl2(dppf), 36mg, 0.05mmol), sodium tert-butoxide (720mg, 7.5mmol), add them to a 100mL three-necked flask, add 30mL toluene, replace nitrogen three times, add 0.8mL tri-tert-butylphosphine (10% mass ratio), heat to 90℃ for 8h. After the reaction is completed, cool to room temperature, add water to quench the reaction, extract three times with dichloromethane, combine the organic phases, dry with anhydrous magnesium sulfate, concentrate in vacuo, slurry the residue with methanol, and filter to finally obtain about 1.74g of compound 14-2, with a yield of 73.3% and MS of 474.93.

[0178] Synthesis of compound (89):

[0179] Compound 14-2 (1.57 g, 3.30 mmol), compound 14-3 (1.02 g, 3.00 mmol), 1,1-bis(diphenylphosphino)diferronichloridopalladium (PdCl2(dppf), 22 mg, 0.03 mmol), sodium tert-butoxide (432 mg, 4.5 mmol) were accurately weighed and added to a 100 mL three-necked flask, 20 mL of toluene was added, nitrogen was replaced three times, 0.5 mL of tri-tert-butylphosphine (10% mass ratio) was added, and the mixture was heated at 90°C for 8 h. After the reaction was completed, the mixture was cooled to room temperature, water was added to quench the reaction, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was slurried with methanol and filtered to obtain about 1.35 g of compound (89) with a yield of 61.2% and MS of 735.81.

[0180] Preparation and characterization examples of OLED devices:

[0181] Device Example 1:

[0182] like Figure 1 As shown, the device structure is shown, and the device preparation method includes the following steps:

[0183] a. Cleaning of ITO conductive glass substrate: Clean the anode layer of ITO conductive glass with detergent, rinse it and then use deionized water, acetone and isopropanol to ultrasonically clean it for 15 minutes, then blow it dry with nitrogen and treat it in a plasma cleaner for 5 minutes to improve the electrode work function.

[0184] b. Preparation of hole injection layer: The ITO conductive glass substrate was moved into a vacuum vapor deposition device and heated in a high vacuum (1×10 -6 Under the condition of 1000 mbar, the hole injection layer material HATCN was evaporated to a thickness of 30 nm.

[0185] c. Preparation of hole transport layer: The hole transport material compound HT is evaporated on the hole injection layer with a thickness of 60 nm to form a hole transport layer.

[0186] d. Preparation of the light-emitting auxiliary layer: Compound (2) was evaporated on the hole transport layer with a thickness of 10 nm to form a light-emitting auxiliary layer.

[0187] e. Preparation of the light-emitting layer: a light-emitting layer is evaporated on the light-emitting auxiliary layer, wherein the main material is selected from the compound RH, the guest light-emitting material is selected from RD, the mass ratio of RH:RD is 97:3, and the thickness is 25 nm, to form a light-emitting layer;

[0188] f. Preparation of electron transport layer: In a vacuum chamber, the electron transport materials ET and Liq are placed in different evaporation crucibles, and ET and Liq are co-deposited at a weight ratio of 5:5 under a high vacuum environment to form an electron transport layer with a thickness of 30 nm;

[0189] g. Forming an electron injection layer: forming an electron injection layer with a thickness of 1 nm on the electron transport layer by vacuum evaporating an electron injection material Liq.

[0190] h. Forming a cathode layer: Al is deposited on the electron injection layer by vacuum evaporation to obtain an Al cathode layer with a thickness of 100 nm.

[0191] i. Packaging: The device is packaged with UV-curable resin in a nitrogen glove box.

[0192]

[0193] The preparation methods of device examples 2-14 are the same as those of device example 1, except that: the materials in the light-emitting auxiliary layer are different. Specifically, the organic compound (2) in device example 1 is replaced by organic compound (16), organic compound (19), organic compound (23), organic compound (31), organic compound (36), organic compound (42), organic compound (44), organic compound (56), organic compound (60), organic compound (62), organic compound (66), organic compound (77) and organic compound (89), respectively. See Table 1 for details.

[0194] Device Comparison Examples 1 and 2:

[0195] The preparation methods of device comparison examples 1 and 2 are the same as those of device example 1, except that the materials in the light-emitting auxiliary layer are different. Specifically, the organic compound (2) in device example 1 is replaced by compound Ref-1 and compound Ref-2, respectively.

[0196] The current-voltage (JV) characteristics of each OLED device were characterized by a characterization device, and the LT95 lifetime and luminous efficiency were recorded at the same time. LT95 represents the time required for the device brightness to decay to 95% of the initial brightness. The results are shown in Table 1.

[0197] Table 1

[0198]

[0199]

[0200] From the results in Table 1, it can be seen that the organic compound provided by the present invention is used as a light-emitting auxiliary material in an organic electroluminescent device, and exhibits better photoelectric performance than the device comparison examples 1 and 2. The reason is that the aromatic amine-containing organic compound of the present invention is introduced into The steric hindrance and solubility of the molecule are improved, which on the one hand improves the film-forming property of the molecule, and on the other hand makes the organic compound have good transmission performance and charge balance adjustment performance, thereby improving the luminous efficiency of the device and extending the service life of the light-emitting element.

[0201] The technical features of the above-described embodiments may be arbitrarily combined. To make the description concise, not all possible combinations of the technical features in the above-described embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0202] The above-mentioned embodiments only express several implementation methods of the present invention, and the descriptions thereof are relatively specific and detailed, but they cannot be understood as limiting the scope of the invention patent. It should be pointed out that, for ordinary technicians in this field, several variations and improvements can be made without departing from the concept of the present invention, and these all belong to the protection scope of the present invention. Therefore, the protection scope of the patent of the present invention shall be subject to the attached claims.

Claims

1. An aromatic amine-containing organic compound, characterized in that: The aromatic amine-containing organic compound has a structure as shown in formula (I): in, R1 and R2, at each occurrence, are independently selected from -H, -D, a straight chain alkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl group having 3 to 20 carbon atoms; Ar1, Ar2, Ar3, Ar4 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 30 ring atoms; L1 and L2 are independently selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms; The term "substituted or unsubstituted" means that the defined group is unsubstituted or substituted by one or more substituents R, wherein each occurrence of R is independently selected from -D, -F, -Cl, -Br, -I, -CN, a straight-chain alkyl group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, an aromatic group having 6 to 30 carbon atoms, a heteroaromatic group having 5 to 30 ring atoms, or a group formed by the above groups.

2. The aromatic amine-containing organic compound according to claim 1, characterized in that: Said Selected from the following groups: Wherein, * indicates the connection site.

3. The aromatic amine-containing organic compound according to claim 1, characterized in that: The Ar1 and Ar2 are independently selected from any of the following groups: in, Each occurrence of X is independently selected from CR3 or N; Each occurrence of R3 is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, a straight chain alkyl group having 1-20 carbon atoms, a branched or cyclic alkyl group having 3-20 carbon atoms, an aromatic group having 6-30 carbon atoms, a heteroaromatic group having 5-30 ring atoms, or a group formed by the above groups; # indicates a fusion site, which is selected from a C atom.

4. The aromatic amine-containing organic compound according to claim 3, characterized in that: The aromatic amine-containing organic compound has a structure as shown in any one of formulas (II-1) to (II-6):

5. The aromatic amine-containing organic compound according to claim 4, characterized in that: Ar3 and Ar4 are independently selected from any of the following groups: in, Each occurrence of V is independently selected from C, CR4 or N; Each occurrence of Y is independently selected from a single bond, CR5R6, O, S, N, NR7; Each occurrence of R4, R5, R6, and R7 is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, a straight chain alkyl group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, an aromatic group having 6 to 30 carbon atoms, a heteroaromatic group having 5 to 30 ring atoms, or a group formed by the above groups; When V is the attachment site, V is selected from C atoms; when Y is the attachment site, Y is selected from N.

6. The aromatic amine-containing organic compound according to any one of claims 1 to 4, characterized in that: Ar3 and Ar4 are independently selected from any of the following groups: in, Each occurrence of R8 is independently selected from -D, -F, -Cl, -Br, -I, -CN, a straight chain alkyl group having 1-10 carbon atoms, a branched or cyclic alkyl group having 3-10 carbon atoms, an aromatic group having 6-10 carbon atoms, a heteroaromatic group having 5-10 ring atoms, or a group formed by the above groups; Each occurrence of n1 is independently selected from 0, 1, 2, 3, 4 or 5; n2, at each occurrence, is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; n3, at each occurrence, is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; Each occurrence of n4 is independently selected from 0, 1, 2, 3 or 4; n5, at each occurrence, is independently selected from 0, 1, 2, 3, 4, 5 or 6; * indicates the attachment site.

7. The aromatic amine-containing organic compound according to claim 6, characterized in that: The aromatic amine-containing organic compound is selected from the following structures: Wherein: R3 each time appears, is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, methyl, ethyl, isopropyl, propyl, butyl, tert-butyl, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, naphthyl, or a group formed by the above groups.

8. The aromatic amine-containing organic compound according to claim 1, characterized in that: The aromatic amine-containing organic compound is selected from any of the following structural formulas:

9. A light-emitting auxiliary layer material, characterized in that: The light-emitting auxiliary layer material is selected from the aromatic amine-containing organic compound according to any one of claims 1 to 8.

10. An organic electronic device comprising a cathode, an anode and at least one functional layer located between the cathode and the anode, characterized in that: The at least one functional layer comprises the aromatic amine-containing organic compound as claimed in any one of claims 1 to 8.

Images