TW202216655A - Benzophenanthrene derivative and application thereof - Google Patents

Abstract

The invention relates to a benzophenanthrene derivative and application thereof. The structural formula of the benzophenanthrene derivative is shown as a formula (I). The benzophenanthrene derivativeis a novel organic electroluminescent compound with a fused ring structure of indole, benzofuran and benzothienobenzophenanthrene, the intramolecular electron density is increased on the basis of benzophenanthrene, meanwhile, substituent groups are adjusted to increase the molecular steric hindrance, the [pi]-[pi] interaction between molecules is weakened, the internal quantum efficiency of moleculesis improved, and a shorter emission wavelength than conventional compounds is achieved. Meanwhile, the benzophenanthrene derivative hinders the generation of an organic intermolecular excitation-excitation compound and increases the internal electron density and stability, so that the effect and the service life of the organic electroluminescent device prepared from the benzophenanthrene derivative are obviously improved and prolonged.

Description

A kind of triphenylene derivative and application thereof

The invention belongs to the technical field of organic electroluminescence, and particularly relates to a triphenylene derivative and an application thereof.

Most of the substances used in organic electroluminescent elements are pure organics or organometallic complexes in which organics and metals form complexes, which can be divided into hole injectors, hole transporters, light-emitting materials, and electron transporters according to their application. , electron injection, etc. Here, organic substances with relatively small ionization energy are mainly used as the hole injector or hole transporter, and organic substances with high electronegativity are mainly used as the electron injector or electron transporter. In addition, the substance used as the light-emitting auxiliary layer preferably satisfies the following characteristics.

First, the materials used in organic electroluminescent elements need good thermal stability. The reason is that Joule heat occurs in the organic electroluminescent element due to the migration of charges. At present, as a hole transport layer, it is usually used. The glass transition temperature of the material is low, so the phenomenon that the luminous efficiency decreases due to crystallization occurs when driving at a low temperature. Second, in order to reduce the driving voltage, the organic matter adjacent to the cathode and the anode needs to be designed to have a small charge injection barrier and a high charge mobility. Third, the interface between the electrode and the organic layer and the interface between the organic layer and the organic layer always have energy barriers and inevitably accumulate some charges, so it is necessary to use a substance with excellent electrochemical stability.

The light-emitting layer is composed of two substances, a host light-emitting body and a dopant. The dopant needs to have a high quantum efficiency. Compared with the dopant, the host light-emitting body needs to have a larger energy gap, so that energy transfer to the dopant is easy to occur. Displays used for TVs, mobile devices, etc. realize full color according to the three primary colors of red, green, and blue, and the light-emitting layer is composed of red host emitters/dopants, green host emitters/dopants, and blue host emitters/dopants, respectively. dopant composition. At present, blue light materials still have the problems of low luminescence quantum efficiency and poor color purity. The main reason for this situation is that blue light comes from the transition between energy levels with a wide energy gap, and organic compounds with wide band gaps have certain difficulties in molecular design. Secondly, there are strong blue light materials in the system. The π-π bond interaction has strong charge transfer properties, so that there are more non-radiative relaxation channels in the wide frequency gap, which aggravates the fluorescence quenching between molecules and reduces the quantum yield of the blue light system. Therefore, the design and synthesis of blue light materials with excellent comprehensive properties will become an important topic in the research of organic electroluminescent materials.

In view of the above reasons, the present invention is proposed.

In order to solve the above problems existing in the prior art, the present invention provides a triphenylene derivative and its application. The triphenylene derivative of the present invention is applied to organic electroluminescent materials, which can improve organic electroluminescent components. efficiency and longevity.

The first object of the present invention provides a kind of triphenylene derivative, and the structural formula of described triphenylene derivative is shown in formula (I):

Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , T ¹ , T ² are each independently selected from hydrogen, deuterium, straight-chain alkyl with C ₁ -C ₄₀ , with C ₁ - C ₄₀ straight chain heteroalkyl, C ₃ -C ₄₀ branched or cyclic alkyl, C ₃ -C ₄₀ branched or cyclic heteroalkyl, C ₂ -C ₄₀ alkene One of a radical or an alkynyl group, an aromatic ring system or a heteroaromatic ring system with 5 to 60 atoms, among R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , T ¹ , T ² Each group of can be substituted by one or more groups R;

Preferably, T ¹ and T ² are selected from O, S, S(=O), S(=O) ₂ , NR, C(R) ₂ , BR, PR, P(=O)R, Si(R ) the bridging bases of ₂ are bridged to each other;

X1 and X2 are shown in formula (II):

wherein G is C(R) ₂ , NR, oxygen or sulfur, Z is the same or different at each occurrence, selected from CR or N, and ^ indicates adjacent groups X ¹ , X ² in formula (I) ;

Said R is the same or different at each occurrence and is selected from hydrogen atom, deuterium atom, halogen atom, nitrile group, nitro group, N(Ar ¹ ) ₂ , N(R ⁷ ) ₂ , C(=O)Ar ¹ , C(=O)R ⁷ , P(=O)(Ar ¹ ) ₂ , straight-chain alkyl with C ₁ -C ₄₀ , straight-chain heteroalkyl with C ₁ -C ₄₀ , with C ₃ -C ₄₀ branched or cyclic alkyl, C3 _{- C40} branched or cyclic heteroalkyl, C2 _{- C40} alkenyl or alkynyl, 5 to 80, preferably 5 to One of an aromatic or heteroaromatic ring system of 60 atoms, an aryloxy or heteroaryloxy group of 5 to 60 atoms, each group in R may be replaced by one or more groups R ⁷ Substituted, or a combination of these systems, wherein one or more non-adjacent -CH ₂ - groups may be replaced by R ⁷ C=CR ⁷ , C≡C, Si(R ⁷ ) ₂ , Ge(R ⁷ ) ₂ , Sn(R ⁷ ) ₂ , C=O, C=S, C=Se, C=NR ⁷ , P(=O)(R ⁷ ), SO, SO ₂ , NR ⁷ , O, S or CONR ⁷ instead, and wherein one or more hydrogen atoms are replaced by deuterium atoms, halogen atoms, nitrile or nitro groups, wherein two or more adjacent Rs may be optionally joined or fused to form a monocyclic or polycyclic aliphatic , aromatic or heteroaromatic ring systems, which may be substituted by one or more groups R ⁷ ;

R ⁷ is the same or different at each occurrence and is selected from the group consisting of hydrogen atom, deuterium atom, halogen atom, nitrile group, nitro group, N(Ar ¹ ) ₂ , N(R ⁸ ) ₂ , C(=O)Ar ¹ , C(=O)R ⁸ , P(=O)(Ar ¹ ) ₂ , linear alkyl with C ₁ -C ₄₀ , linear heteroalkyl with C ₁ -C ₄₀ , linear heteroalkyl with C ₃ -C ₄₀ branched or cyclic alkyl groups, branched or cyclic heteroalkyl groups with C ₃ -C ₄₀ , alkenyl or alkynyl groups with C ₂ -C ₄₀ , aromatic rings with 5 to 60 atoms or one of heteroaromatic ring systems, aryloxy or heteroaryloxy groups having ⁵ to 60 atoms, each group in R may be ^substituted with one or more groups R, or any of these systems Combinations where one or more non-adjacent -CH ₂ - groups may be replaced by R ⁸ C=CR ⁸ , C≡C, Si(R ⁸ ) ₂ , Ge(R ⁸ ) ₂ , Sn(R ⁸ ) ₂ , C=O, C=S, C=Se, C=NR ⁸ , P(=O)(R ⁸ ), SO, SO ₂ , NR ⁸ , O, S or CONR ⁸ instead, and one or more of them Hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile or nitro groups, wherein two or more adjacent substituents R may be optionally joined or fused to form monocyclic or polycyclic aliphatic, aromatic or a heteroaromatic ring system, which may be substituted with one or more groups ^R8 ;

Ar ¹ is the same or different at each occurrence and is selected from aromatic or heteroaromatic ring systems having 5 to 30 atoms, which may be substituted by one or more non-aromatic groups R ⁸ ; here The two groups Ar ¹ bound to the same nitrogen or phosphorus atom can also be bridged to each other by a single bond or a bridging group selected from N(R ⁸ ), C(R ⁸ ) ₂ , oxygen or sulfur;

R ⁸ is selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, aliphatic hydrocarbon group with C ₁ -C ₂₀ , aromatic ring or heteroaromatic ring system with 5~30 atoms, wherein one or more hydrogen Atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R ⁸ may form with each other a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system.

Further, the R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , T ¹ , T ² are each independently selected from hydrogen, deuterium, alkyl groups with C ₁ -C ₄₀ , alkyl groups with C ₃ -C ₄₀ branched or cyclic alkyl group, one of aromatic ring systems or heteroaromatic ring systems with 5 to 60 atoms, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ Each of , T ¹ , T ² may be substituted with one or more groups R.

Further, the R is the same or different at each occurrence, and is selected from a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, N(Ar ¹ ) ₂ , a straight-chain alkyl group with C ₁ -C ₄₀ , a group with C ₁ -C ₄₀ straight chain heteroalkyl, branched or cyclic alkyl with C ₃ -C ₄₀ , branched or cyclic heteroalkyl with C ₃ -C ₄₀ , with C ₂ -C ₄₀ alkenyl or alkynyl, aromatic or heteroaromatic ring systems having 5 to 80, preferably 5 to 60, atoms;

Ar ¹ is the same or different at each occurrence and is selected from aromatic or heteroaromatic ring systems having 5 to 30 atoms, which may be substituted by one or more non-aromatic groups R ⁸ ; here The two groups Ar ¹ bound to the same nitrogen or phosphorus atom can also be bridged to each other by a single bond or a bridging group selected from N(R ⁸ ), C(R ⁸ ) ₂ , oxygen or sulfur;

R ⁸ is selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, aliphatic hydrocarbon group with C ₁ -C ₂₀ , aromatic ring or heteroaromatic ring system with 5~30 atoms, wherein one or more hydrogen Atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R ⁸ may form with each other a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system.

Aryl in the sense of the present invention contains 6 to 60 carbon atoms, and heteroaryl in the sense of the present invention contains 2 to 60 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5 ; the heteroatom is preferably selected from N, O or S. Aryl or heteroaryl here is taken to mean simple aromatic rings, i.e., benzene, naphthalene, etc., or simple heteroaromatic rings, such as pyridine, pyrimidine, thiophene, etc., or fused aryl or heteroaryl groups bases, such as anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic rings connected to each other by single bonds, such as biphenyls, are on the contrary not referred to as aryl or heteroaryl groups, but as aromatic ring systems.

An aromatic or heteroaromatic ring system in the sense of the present invention is intended to be taken to mean a system which does not necessarily have to contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups can also consist of non-aromatic units For example C, N, O or S atoms are attached. Thus, for example, as in systems in which two or more aryl groups are linked by, for example, short alkyl groups, such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, Systems of diaryl ethers and the like are also taken to mean aromatic ring systems in the sense of the present invention.

For aliphatic hydrocarbon radicals or alkyl radicals or alkenyl radicals or alkynyl radicals which contain 1 to 40 carbon atoms in the sense of the present invention and in which the individual hydrogen atoms or -CH ₂ - groups can also be substituted by the aforementioned radicals are preferably considered to be Refers to the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptyl Alkenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. The alkoxy groups preferably have 1 to 40 carbon atoms are considered to be methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy base, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-heptyloxy Octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy. Heteroalkyl groups preferably have 1 to 40 carbon atoms, and refer to groups in which individual hydrogen atoms or -CH ₂ - groups may be replaced by oxygen, sulfur, halogen atoms, and are considered to mean alkoxy, Alkylthio, fluoroalkoxy, fluoroalkylthio, especially methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy Oxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio group, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2,2-trifluoroethoxy, 2,2,2-trifluoroethylthio, vinyloxy, vinylthio radical, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio base, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio group, hexynyloxy, hexynylthio.

In general, cycloalkyl, cycloalkenyl according to the present invention can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl , cycloheptenyl, wherein one or more -CH2- groups can be replaced by the above-mentioned groups; in addition, one or more hydrogen atoms can also be replaced by deuterium atoms, halogen atoms or nitrile groups.

、苝、熒蒽、並四苯、並五苯、苯並芘、聯苯、偶 苯、三聯苯、三聚苯、芴、螺二芴、二氫菲、二氫芘、四氫芘、順式或反式茚並芴、順式或反式茚並哢唑、順式或反式吲哚並哢唑、三聚茚、異三聚茚、螺三聚茚、螺異三聚茚、呋喃、苯並呋喃、異苯並呋喃、二苯並呋喃、噻吩、苯並噻吩、異苯並噻吩、二苯並噻吩、吡咯、吲哚、異吲哚、哢唑、吡啶、喹啉、異喹啉、吖啶、菲啶、苯並[5,6]喹啉、苯並[6,7]喹啉、苯並[7,8]喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯並咪唑、萘並咪唑、菲並咪唑、吡啶並咪唑、吡嗪並咪唑、喹喔啉並咪唑、噁唑、苯並噁唑、萘並噁唑、蒽並噁唑、菲並噁唑、異噁唑、1,2-噻唑、1,3-噻唑、苯並噻唑、噠嗪、六氮雜苯並菲、苯並噠嗪、嘧啶、苯並嘧啶、喹喔啉、1,5-二氮雜蒽、2,7-二氮雜芘、2,3-二氮雜芘、1,6-二氮雜芘、1,8-二氮雜芘、4,5-二氮雜芘，4,5,9,10-四氮雜苝、吡嗪、吩嗪、吩噁嗪、吩噻嗪、熒紅環、萘啶、氮雜哢唑、苯並哢啉、哢啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯並三唑、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲嗪和苯並噻二唑或者衍生自這些體系的組合的基團。 The aromatic or heteroaromatic ring atoms according to the invention, aromatic or heteroaromatic ring systems which in each case may also be substituted by the abovementioned radicals R ⁸ , in particular refer to radicals derived from benzene, Naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,

, perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, benzene, terphenyl, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis Indenofluorenes of formula or trans, cis or trans indenozazoles, cis or trans indolopyrazoles, trimerindene, heterotrimerindene, spirotrimerindene, spiroheterotrimerindene, furan , benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, azole, pyridine, quinoline, isoquinoline Line, acridine, phenanthridine, benzo[5,6]quinoline, benzo[6,7]quinoline, benzo[7,8]quinoline, phenothiazine, phenoxazine, pyrazole, indium azole, imidazole, benzimidazole, naphthimidazole, phenanthroimidazole, pyridimidazole, pyrazinimidazole, quinoxalineimidazole, oxazole, benzoxazole, naphthoxazole, anthraxazole, phenanthrene oxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1 ,5-diazathene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diaza Heteropyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorochrome, naphthyridine, azaazole, benzoquinoline, quinoline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2 ,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3 ,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1, 2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole or groups derived from combinations of these systems.

Further, the structures of the triphenylene derivatives mainly include CJHB271~CJHB480, wherein G is selected from oxygen, sulfur, CH ₂ , C(CH ₃ ) ₂ , C(C ₆ H ₅ ) ₂ , N-CH ₃ , one of NC ₂ H ₅ , NC ₆ H ₅ :

The second object of the present invention is to provide an application of the triphenylene derivative in an organic electroluminescent material.

Further, the organic electroluminescent material is a material for an organic electroluminescent element, a material for an organic field effect transistor or a material for an organic thin film solar cell.

The organic electroluminescent material may be constituted by using the triphenylene derivative of the present invention alone, or may contain other compounds simultaneously.

The third object of the present invention is to provide an organic electroluminescence device, the organic electroluminescence device includes a first electrode, a second electrode, and at least one layer of organic electroluminescence disposed between the first electrode and the second electrode. layer, at least one organic layer contains the triphenylene derivative.

The organic electroluminescent device includes a cathode, an anode, and at least one light-emitting layer. In addition to these layers, it may also contain other layers, for example in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, excitation layers Sub-blocking layer, electron blocking layer and/or charge generating layer. An intermediate layer having, for example, an exciton blocking function can likewise be introduced between the two light-emitting layers. It should be noted, however, that each of these layers does not have to be present. The organic electroluminescent device described herein may comprise one light-emitting layer, or it may comprise multiple light-emitting layers. That is, various light-emitting compounds capable of emitting light are used in the light-emitting layer. Particular preference is given to systems having three emitting layers, wherein the three layers can exhibit blue, green and red emission. If more than one light-emitting layer is present, according to the invention, at least one of these layers comprises a compound of the invention.

Further, the organic electroluminescent device according to the present invention does not comprise a separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, ie the light emitting layer and the hole injection layer or The anode is directly adjacent, and/or the light emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode.

In the other layers of the organic electroluminescent device according to the invention, in particular in the hole injection and hole transport layers as well as in the electron injection and electron transport layers, all materials can be prepared in the manner generally used according to the prior art use. A person skilled in the art will therefore be able to use all materials known for organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive step.

Furthermore, preference is given to organic electroluminescent devices which are characterized in that one or more layers are applied by means of a sublimation method, wherein the vacuum sublimation device is passed through at an initial pressure of less than 10 ⁻⁵ Pa, preferably less than 10 ⁻⁶ Pa Vapor deposition to apply the material. However, the initial pressure may also be even lower, eg below 10 ⁻⁷ Pa.

Preference is likewise given to organic electroluminescent devices characterized in that the layer or layers are applied by means of an organic vapour deposition method or by means of sublimation of a carrier gas, wherein the applied layer or layers are applied at a pressure of between 10 ⁻⁵ Pa and 1 Pa. mentioned materials. A particular example of this method is the organic vapor jet printing method, in which the material is applied directly through a nozzle and is thus structured.

Also preferred are organic electroluminescent devices, from solution, for example by spin coating, or by means of any desired printing method such as screen printing, flexographic printing, lithographic printing, photoinduced thermography, thermal transfer printing, spraying Ink printing or nozzle printing to create one or more layers. Soluble compounds are obtained, for example, by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Also possible are hybrid methods in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapour deposition.

These methods are generally known to those skilled in the art, and they can apply them to organic electroluminescent elements comprising the compounds according to the invention without inventive effort.

Accordingly, the invention also relates to a method for producing an organic electroluminescent device according to the invention, characterized in that at least one layer is applied by means of a sublimation method, and/or characterized in that it is sublimated by means of an organic vapor deposition method or by means of a carrier gas to apply at least one layer, and/or characterized in that at least one layer is applied from solution by spin coating or by means of a printing method.

Furthermore, the present invention relates to containing at least one fused-ring aromatic compound of the present invention as indicated above. The same preferences as indicated above for organic electroluminescent devices apply to the fused-ring aromatic compounds of the present invention. In particular, the fused-ring aromatic compound may preferably contain other compounds in addition. Processing the fused-ring aromatic compounds according to the invention from the liquid phase, for example by spin coating or by printing methods, requires a formulation of the compounds according to the invention. These formulations can be, for example, solutions, dispersions or emulsions. For this purpose, mixtures of two or more solvents may preferably be used. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, Tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2, 4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanol Hexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indan, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenethyl ether, 1,4 -Diisopropylbenzene, Dibenzyl Ether, Diethylene Diethylene Alcohol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol Alcohol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, or a mixture of these solvents.

Further, the organic layer further includes one of an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, and a light emitting layer.

、苯並蒽和並五苯及其衍生物中的一種。 Further, the light-emitting layer includes a dopant and a light-emitting host, the dopant includes the triphenylene derivative, and the light-emitting host is the triphenylene derivative, naphthalene, anthracene , pyrene, perylene, phenanthrene, fluoranthene,

, one of benzanthracene and pentacene and their derivatives.

Further, the quality ratio of the dopant to the light-emitting host is 1:99-50:50.

Compared with the prior art, the beneficial effects of the present invention are:

The triphenylene derivative of the present invention is a novel organic electroluminescent compound with condensed ring structures of indole, benzofuran, and benzothiphenanthrene, which increases intramolecular luminescence on the basis of triphenylene. At the same time, adjusting the substituent group increases molecular steric hindrance, weakens the π-π interaction between molecules, improves the internal quantum efficiency of the molecule, and has a shorter emission wavelength than existing compounds. At the same time, the triphenylene derivative hinders the formation of organic intermolecular exciter-excited complexes, and increases the internal electron density and stability. Therefore, the triphenylene derivative of the present invention is used to prepare an organic electroluminescent device. The effect and life are significantly improved. In addition, the triphenylene derivative improves the solubility of the solution and solves the problems of productivity and cost of the process that the blue light material has in the past, and it is not a vapor deposition process in the original process. , but can also be used to prepare light-emitting layers in other solution processes.

1: Substrate

2: Anode

3: hole injection layer

4: hole transport/electron blocking layer

5: Light-emitting layer

6: Hole blocking/electron transport layer

7: Electron injection layer

8: Cathode

In order to illustrate the embodiments of the present invention or the technical solutions in the prior art more clearly, the following briefly introduces the accompanying drawings that need to be used in the description of the embodiments or the prior art. Obviously, the drawings in the following description are only the For some embodiments of the invention, for those of ordinary skill in the art, other drawings can also be obtained according to these drawings without any creative effort.

1 is a schematic diagram of a bottom emission example of the organic electroluminescence device of the present invention;

FIG. 2 is a schematic diagram of a top emission example of the organic electroluminescent device of the present invention.

In order to make the objectives, technical solutions and advantages of the present invention clearer, the technical solutions of the present invention will be described in detail below. Obviously, the described embodiments are only some, but not all, embodiments of the present invention. Based on the embodiments of the present invention, all other implementations obtained by those of ordinary skill in the art without creative work fall within the protection scope of the present invention.

The following test instruments and methods for performance testing of OLED materials and components are as follows:

OLED component performance testing conditions:

Luminance and chromaticity coordinates: tested with the spectral scanner PhotoResearch PR-715;

Current density and lighting voltage: tested with Keithley 2420 digital source meter;

Power Efficiency: Tested with NEWPORT 1931-C;

Life Test: Use LTS-1004AC Life Test Device.

Example 1

The preparation method of compound CJHB271 comprises the following steps:

Step 1: Preparation of Compound Int.-1

Under nitrogen protection, 24.5g (127.0mmol) of p-chlorobromobenzene was dissolved in 300mL of dry tetrahydrofuran, cooled to -78°C with liquid nitrogen, 56.0mL of 2.5M n-butyllithium n-hexane solution was slowly added dropwise, and stirred. React for 1 hour, add dropwise a solution of 19.5 g (140.0 mmol) of p-chlorobenzonitrile dissolved in 50 mL of dry tetrahydrofuran, warm to room temperature and stir for 2 hours, add 50 mL of saturated aqueous ammonium chloride solution, stir for 30 minutes, separate The organic phase and the aqueous phase were extracted with ethyl acetate, the organic phase was collected and dried, filtered, the filtrate was concentrated to dryness under reduced pressure, and separated and purified by a silica gel column to obtain 27.7 g of a white solid with a yield of 87%.

The second step: preparation of compound Int.-2

Under nitrogen protection, 12.6 g (50.0 mmol) of Int.-1 prepared in the first step was dissolved in 200 mL of dichloromethane, cooled to 0 °C in an ice-water bath, and 20.0 g of carbon tetrabromide and 12.5 g of phosphorous acid were added. Triisopropyl ester, stirred for 30 minutes, raised to room temperature and reacted for 1 hour, added dropwise 50 mL of 1N dilute hydrochloric acid aqueous solution, stirred for 30 minutes, separated the organic phase, extracted the aqueous phase with dichloromethane, collected the organic phase, dried Dry, filter, concentrate the filtrate to dryness under reduced pressure, and separate and purify with silica gel column to obtain white solid Int.-2 with a yield of 92%.

The third step: preparation of compound Int.-3

Mix 20.0 g (50.0 mmol) of the intermediate Int.-2 prepared in the second step with 100 mL of 1,4-dioxane, under nitrogen protection, add 110.0 mmol of benzofuran-2-boronic acid or benzoic acid Thiophene-2-boronic acid or 1-substituted indole-2-boronic acid or 1,1-substituted indene-2-boronic acid and 112.5 mg of palladium acetate catalyst, 410.5 mg of 2-dicyclohexylphosphine-2',6'- Dimethoxybiphenyl and 80.0 mmol of hydrated potassium phosphate were added, then 40 mL of water was added, the temperature was raised to 60°C and stirred for 12 hours, cooled to room temperature, 100 mL of ethyl acetate and 100 mL of water were added, and the organic phase was separated, The aqueous phase was extracted with ethyl acetate, the organic phase was collected and washed with saturated brine, the organic phase was dried and filtered, the filtrate was concentrated to dryness under reduced pressure, and separated and purified with a silica gel column to obtain Int.-3 as a white solid in a yield of 60-65%.

The fourth step: preparation of compound Int.-4

20.0 mmol of the intermediate Int-3 prepared in the third step was mixed with 100 mL of chloroform and 20 mL of nitromethane, and then 1.6 g of anhydrous ferric chloride was added, heated to reflux for 24 hours, cooled to room temperature, and added 50 mL of dilute aqueous hydrochloric acid solution was extracted with dichloromethane, the organic phase was collected, dried, filtered, the filtrate was concentrated to dryness under reduced pressure, and separated and purified with a silica gel column to obtain the intermediate Int.-4 in a yield of 55~65%.

Step 5: Preparation of Compound CJHB271

Disperse 5.0 mmol of the intermediate Int.-4 prepared in the fourth step in 60 mL of toluene, add 12.0 mmol of diphenylamine, then add 1.5 g (15.0 mmol) of sodium tert-butoxide, 55.0 mg (0.05 mmol) of Pd2 (dba) 3CHCl3 catalyst and 0.1 mL of 10% tert-butylphosphorus toluene solution, heat up to 100 ° C and stir for 12 hours, after the reaction, 50 mL of water was added to separate the organic phase, the aqueous phase was extracted with toluene-THF, collected The organic phase was dried, filtered, the filtrate was concentrated to dryness under reduced pressure, separated and purified with a silica gel column, and then recrystallized with dichloromethane and ethanol to obtain CJHB271, a yellow solid.

The experimental data are shown in Table 1:

Example 2

The preparation method of compound CJHB387 comprises the following steps:

The first step: preparation of compound Int.-5

Under nitrogen protection, 12.8 g (50.0 mmol) of 2,7-dimethoxyxanthene-9-one was dissolved in 200 mL of dichloromethane, cooled to 0 °C in an ice-water bath, and 20.0 g of tetrabromide was added. Carbon and 12.5 g of triisopropyl phosphite were stirred for 30 minutes, raised to room temperature and reacted for 1 hour, 50 mL of 1N dilute hydrochloric acid aqueous solution was added dropwise, stirred for 30 minutes, the organic phase was separated, and the aqueous phase was extracted with dichloromethane , collect organic phase, dried, filtered, the filtrate was concentrated to dryness under reduced pressure, and separated and purified by silica gel column to obtain Int.-5 as a white solid with a yield of 94%.

The second step: preparation of compound Int.-6

Referring to the preparation method of the third step of Example 1, only Int.-2 in the third step of Example 1 was replaced with the intermediate Int.-5 to prepare the intermediate Int.-6 with a yield of 80-90%.

The third step: preparation of compound Int.-7

Referring to the preparation method of the fourth step of Example 1, only Int.-3 in the fourth step of Example 1 was replaced by the intermediate Int.-6, and the reaction was stirred at room temperature for 12 hours to prepare the intermediate Int.-7, The yield is 65~75%.

The fourth step: preparation of compound Int.-8

Under nitrogen protection, 20.0 mmol of intermediate Int.-7 was dissolved in 120 mL of dry dichloromethane, cooled to -40°C with liquid nitrogen, and a solution of 40.0 mmol of boron tribromide dissolved in dichloromethane was added dropwise, The reaction was stirred for 2 hours, warmed to room temperature, 50 mL of 1N diluted hydrochloric acid aqueous solution was added dropwise, and stirred for 1 hour At the time, the organic phase was separated, the aqueous phase was extracted with dichloromethane, the organic phase was dried, filtered, the filtrate was concentrated to dryness under reduced pressure, and was separated and purified with a silica gel column to obtain solid Int.-8 with a yield of 90-94%.

Step 5: Preparation of Compound Int.-9

Under nitrogen protection, 20.0 mmol of intermediate Int.-8 was dissolved in 120 mL of dry dichloromethane, 60.0 mmol of pyridine was added, cooled to 0 °C with an ice-water bath, and 48.0 mmol of trifluoromethanesulfonic anhydride was added dropwise to dissolve The solution in dichloromethane was stirred for 2 hours, raised to room temperature and stirred for 2 hours, 50 mL of 1N dilute hydrochloric acid aqueous solution was added, the organic phase was separated, the aqueous phase was extracted with dichloromethane, the organic phase was dried, filtered, and the filtrate was reduced. Pressed and concentrated to dryness, separated and purified by silica gel column to obtain solid Int.-9 with a yield of 92-96%.

Step 6: Preparation of Compound CJHB387

Disperse 5.0 mmol of the intermediate Int.-9 prepared in the fifth step in 60 mL of toluene, add 12.0 mmol of 4,4'-dimethyldiphenylamine, and then add 2.0 g (20.0 mmol) of sodium tert-butoxide, 55.0mg (0.05mmol) of Pd2(dba)3CHCl3 catalyst and 0.1mL of 10% tert-butylphosphorus toluene solution were heated to 100°C and stirred for 12 hours. After the reaction was completed, 50mL of water was added to separate the organic phase, water The phase was extracted with ethyl acetate-THF, the organic phase was collected and dried, filtered, the filtrate was concentrated to dryness under reduced pressure, separated and purified with a silica gel column, and then recrystallized with THF-toluene to obtain CJHB387, a yellow solid.

The experimental data are shown in Table 2.

Example 3

Preparation of compounds CJHB270~CJHB324, CJHB386, CJHB388~CJHB403:

With reference to the preparation method of Examples 1 ~ 2, only the diphenylamine of the fifth step in Example 1 or the 4,4'-dimethyldiphenylamine of the sixth step in Example 2 is replaced by different amines, and other experimental parameters Make general adjustments.

Example 4

Preparation of compound CJHB336:

The first step: the preparation of compound Int.-11

The intermediate Int.-10 of 6.6mmol (referring to the synthetic method of embodiment 1, only replaces the p-chlorobromobenzene in the first step with bromobenzene to prepare the intermediate Int.-10) is dispersed in 100mL dry THF, in Under nitrogen protection, it was cooled to -78°C with liquid nitrogen, 3.2 mL of 2.5M tert-butyllithium was added dropwise, the reaction was stirred for 1 hour, and 10.0 mmol of trimethyl borate was added dropwise. After 1 hour of reaction, 50 mL of 2N diluted Aqueous hydrochloric acid solution, the organic phase was separated, the aqueous phase was extracted with ethyl acetate, the organic phase was collected and dried, filtered, the filtrate was concentrated to dryness under reduced pressure, washed with petroleum ether, and filtered to obtain a white solid with a yield of 65-75%.

The second step: preparation of compound CJHB336

Mix 5.0 mmol of the intermediate Int.-10 prepared in the first step with 40 mL of toluene, under nitrogen protection, add 4.0 mmol of 2-chloro-4,6-diphenyl-1,3,5-triazine, 10.0 mmol of anhydrous potassium carbonate and 58.0 mg of Pd(PPh3)4 catalyst were added, 20 mL of ethanol and 20 mL of water were added, the temperature was raised to reflux and stirred for 12 hours, cooled to room temperature, and 50 mL of dichloromethane and 100 mL of water were added. , separate the organic phase, extract the aqueous phase with dichloromethane again, collect the organic phase and wash it with saturated brine, dry the organic phase and filter, concentrate the filtrate to dryness under reduced pressure, and use a silica gel column for separation and purification to obtain a white solid CJHB336 in a yield of 75~ 86%.

The experimental data are shown in Table 3.

Example 5

Preparation of compounds CJHB325~CJHB335, CJHB337~CJHB385:

Referring to the preparation method of Example 4, only the 2-chloro-4,6-diphenyl-1,3,5-triazine in the second step in Example 4 was replaced by different halogenated compounds, and other experimental parameters were routinely adjusted. .

Example 6

The preparation method of compound CJHB413 comprises the following steps:

The first step: preparation of compound Int.-13

Take 22.0 g (50.0 mmol) of the intermediate Int.-12 (prepared with reference to the synthetic method of Example 2) and mix it with 100 mL of 1,4-dioxane, under nitrogen protection, add 110.0 mmol of benzofuran- 3-boronic acid Or benzothiophene-3-boronic acid or 1-substituted indole-3-boronic acid or 1,1-substituted indene-3-boronic acid and 112.5 mg of palladium acetate catalyst, 410.5 mg of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl and 80.0 mmol of hydrated potassium phosphate were added, 40 mL of water was added, the temperature was raised to 60 °C and the reaction was stirred for 12 hours, cooled to room temperature, 100 mL of ethyl acetate and 50 mL of water were added, and the mixture was separated. The organic phase and the aqueous phase were extracted with ethyl acetate. The organic phase was collected and washed with saturated brine. The organic phase was dried and filtered. The filtrate was concentrated to dryness under reduced pressure. 80%.

The second step: the preparation of compound Int.-14

Under nitrogen protection, 10.5 mmol of the intermediate Int.-13 prepared in the first step was dissolved in 200 mL of dichloromethane, 63.0 mmol of iodine was added, 10 mL of propylene oxide was added, and the reaction was stirred with 254 nm ultraviolet light irradiation. After 12 hours, concentrated to dryness under reduced pressure, added 100 mL of methanol to disperse, filtered, and the filter cake was separated and purified with a silica gel column to obtain a yellow solid intermediate Int.-14 with a yield of 85-95%.

The third step: preparation of compound Int.-15

With reference to the synthetic method of the fourth step of Example 2, only the intermediate Int.-7 in the fourth step of Example 2 is replaced by the intermediate Int.-13, and the intermediate Int.-15 is prepared, and the yield is 92～96 %.

The fourth step: preparation of compound Int.-16

With reference to the synthetic method of the fifth step of Example 2, only the intermediate Int.-8 in the fifth step of Example 2 is replaced by the intermediate Int.-15, and the intermediate Int.-16 is prepared, and the yield is 85～90 %.

Step 5: Preparation of Compound CJHB413

Disperse 5.0 mmol of the intermediate Int.-16 prepared in the fourth step in 60 mL of toluene, add 12.0 mmol of 4,4'-dimethyldiphenylamine, and then add 2.0 g (20.0 mmol) of sodium tert-butoxide, 55.0mg (0.05mmol) of Pd2(dba)3CHCl3 catalyst and 0.1mmol of Xanphos were heated to 90°C and stirred for 12 hours. After the reaction was completed, 50mL of water was added to separate the organic phase, and the aqueous phase was treated with ethyl acetate-THF. Extract, collect and dry the organic phase, filter, and concentrate the filtrate to dryness under reduced pressure, separate and purify with silica gel column, and then recrystallize with THF-toluene to obtain CJHB413, a yellow solid.

The experimental data are shown in Table 4:

Example 7

Preparation of compounds CJHB404~CJHB412, CJHB414~CJHB429:

Referring to the preparation method of Example 6, only the 4,4'-dimethyldiphenylamine in the fifth step in Example 6 was replaced by different amines, and other experimental parameters were routinely adjusted.

Example 8

Preparation of compounds CJHB430~CJHB480:

Referring to the preparation method of Example 4, only the 2-chloro-4,6-diphenyl-1,3,5-triazine in the second step in Example 4 was replaced by different halogenated compounds, and other experimental parameters were routinely adjusted. .

Test Example 1

As shown in FIG. 1, an OLED element, the preparation method of the OLED element shown includes the following steps:

1) The glass substrate coated with the ITO conductive layer was ultrasonically treated in a cleaning agent for 30 minutes, rinsed in deionized water, ultrasonicated in an acetone/ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dry, and used UV light washer was irradiated for 10 minutes and the surface was bombarded with a beam of low energy cations.

2) Place the above-mentioned treated ITO glass substrate in a vacuum chamber, evacuate to 1 × 10 ^-5 ~ 9 × 10 ^-3 Pa, and continue to evaporate compound DNTPD as a hole injection layer on the above-mentioned anode layer film respectively. , the vapor-deposited film thickness is 300Å; NPD is continuously vapor-deposited on the above hole injection layer film as a hole transport layer, and the vapor-deposited film thickness is 2200Å;

3) Continue to evaporate a layer of compound HT202 as the electron blocking layer on the hole transport layer, and the evaporation film thickness is 100Å;

4) on the electron blocking layer, one of the triphenylene derivatives CJHB271～CJHB480 prepared by one layer of embodiment 1-8 and BH011 are used as the organic light-emitting layer, wherein, BH011 is the host material and the benzophenone of the present invention. The phenanthrene derivative is a doping material, the doping concentration of the triphenylene derivative in BH011 is 1~20%, and the evaporation film thickness is 500Å;

5) Continue to vapor-deposit a layer of compound TPBI as a hole blocking layer on the organic light-emitting layer, and the vapor-deposited film thickness is 50Å;

6) Continue to evaporate a layer of compound LiQ and ET205 on the hole blocking layer as the electron transport layer of the device, wherein the quality ratio of LiQ and ET205 is 1:1, and the thickness of the evaporated film is 200Å;

7) Continue to vapor-deposit a layer of compound LiF as the electron transport layer of the device on the above-mentioned hole blocking layer, and the thickness of the vapor-deposited film is 10Å; finally, vapor-deposit metal aluminum as the cathode layer of the element on the above-mentioned electron transport layer, and the vapor-deposited film Thickness is 1500Å.

Wherein, the structural formula of the compound used in Test Example 1 is as follows:

Test sample 1

The triphenylene derivative in Test Example 1 was CJHB271-1, and the other light-emitting elements were prepared according to the method of Test Example 1.

Test sample 2

The triphenylene derivative in Test Example 1 was CJHB271-4, and the other light-emitting elements were prepared according to the method of Test Example 1.

Test sample 3

The triphenylene derivative in Test Example 1 was CJHB387-1, and the other light-emitting elements were prepared according to the method of Test Example 1.

Test sample 4

The triphenylene derivative in Test Example 1 was CJHB387-4, and the other light-emitting elements were prepared according to the method of Test Example 1.

Test sample 5

The triphenylene derivative in Test Example 1 was CJHB336-2, and the other light-emitting elements were prepared according to the method of Test Example 1.

Test sample 6

The triphenylene derivative in Test Example 1 was CJHB413-2, and the other light-emitting elements were prepared according to the method of Test Example 1.

Test sample 7

The triphenylene derivative in Test Example 1 was CJHB413-5, and the other light-emitting elements were prepared according to the method of Test Example 1.

control sample 1

The triphenylene derivative in Test Example 1 was replaced with compound BD10, and other light-emitting elements were prepared according to the method of Test Example 1, wherein the structural formula of compound BD10 was as follows:

The performances of the light-emitting elements of test samples 1-7 and control sample 1 were tested, and the results are shown in Table 5.

As can be seen in Table 5 above, the data on the driving voltage, FWHM, current efficiency, and device lifetime ^LT90 % under the initial condition of brightness of 1000cd/m2 under the condition of a current density of 10mA/ ^cm2 are for the control. Sample 1 normalized.

Conclusion: It can be seen from Table 5 of the performance test results that the compound of the present invention can be used as a blue dye to obtain a deep blue organic electroluminescence device. Compared with the organic electroluminescence device using BD10 as a blue light doping material, the current efficiency of the element Higher, lower driving voltage, and the device's ^LT90 % lifetime has also been greatly improved at an initial brightness of 1000cd/m2.

Industrial application possibilities

The organic electroluminescence device of the present invention can be used in wall-mounted TVs, flat panel displays, flat illuminants for lighting, photocopiers, printers, backlights of liquid crystal displays, light sources for measuring instruments, etc., display panels, sign lamps, etc. application.

The above are only specific embodiments of the present invention, but the protection scope of the present invention is not limited to this. Any person skilled in the art can easily think of changes or substitutions within the technical scope disclosed by the present invention. should be included within the protection scope of the present invention. Therefore, the protection scope of the present invention should be based on the protection scope of the claims.

1: Substrate

2: Anode

3: hole injection layer

4: hole transport/electron blocking layer

5: Light-emitting layer

6: Hole blocking/electron transport layer

7: Electron injection layer

8: Cathode

Claims (10)

A kind of triphenylene derivative, it is characterized in that, the structural formula of described triphenylene derivative is shown in formula (I):

Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , T ¹ , T ² are each independently selected from hydrogen, deuterium, straight-chain alkyl with C ₁ -C ₄₀ , with C ₁ - C ₄₀ straight chain heteroalkyl, C ₃ -C ₄₀ branched or cyclic alkyl, C ₃ -C ₄₀ branched or cyclic heteroalkyl, C ₂ -C ₄₀ alkene One of a radical or an alkynyl group, an aromatic ring system or a heteroaromatic ring system with 5 to 60 atoms, among R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , T ¹ , T ² Each group of can be substituted by one or more groups R; Preferably, T ¹ and T ² are selected from O, S, S(=O), S(=O) ₂ , NR, C(R) ₂ , BR, PR, P(=O)R, Si(R ) the bridging bases of ₂ are bridged to each other; X ¹ and X ² are shown in formula (II):

wherein G is C(R) ₂ , NR, oxygen or sulfur, Z is the same or different at each occurrence, selected from CR or N, and ^ indicates adjacent groups X ¹ , X ² in formula (I) ; Said R is the same or different at each occurrence and is selected from hydrogen atom, deuterium atom, halogen atom, nitrile group, nitro group, N(Ar ¹ ) ₂ , N(R ⁷ ) ₂ , C(=O)Ar ¹ , C(=O)R ⁷ , P(=O)(Ar ¹ ) ₂ , straight-chain alkyl with C ₁ -C ₄₀ , straight-chain heteroalkyl with C ₁ -C ₄₀ , with C ₃ -C ₄₀ branched or cyclic alkyl, C3 _{- C40} branched or cyclic heteroalkyl, C2 _{- C40} alkenyl or alkynyl, 5 to 80, preferably 5 to One of an aromatic or heteroaromatic ring system of 60 atoms, an aryloxy or heteroaryloxy group of 5 to 60 atoms, each group in R may be replaced by one or more groups R ⁷ Substituted, or a combination of these systems, wherein one or more non-adjacent -CH ₂ - groups may be replaced by R ⁷ C=CR ⁷ , C≡C, Si(R ⁷ ) ₂ , Ge(R ⁷ ) ₂ , Sn(R ⁷ ) ₂ , C=O, C=S, C=Se, C=NR ⁷ , P(=O)(R ⁷ ), SO, SO ₂ , NR ⁷ , O, S or CONR ⁷ instead, and wherein one or more hydrogen atoms are replaced by deuterium atoms, halogen atoms, nitrile or nitro groups, wherein two or more adjacent Rs may be optionally joined or fused to form a monocyclic or polycyclic aliphatic , aromatic or heteroaromatic ring systems, which may be substituted by one or more groups R ⁷ ; R ⁷ is the same or different at each occurrence and is selected from the group consisting of hydrogen atom, deuterium atom, halogen atom, nitrile group, nitro group, N(Ar ¹ ) ₂ , N(R ⁸ ) ₂ , C(=O)Ar ¹ , C(=O)R ⁸ , P(=O)(Ar ¹ ) ₂ , linear alkyl with C ₁ -C ₄₀ , linear heteroalkyl with C ₁ -C ₄₀ , linear heteroalkyl with C ₃ -C ₄₀ branched or cyclic alkyl groups, branched or cyclic heteroalkyl groups with C ₃ -C ₄₀ , alkenyl or alkynyl groups with C ₂ -C ₄₀ , aromatic rings with 5 to 60 atoms or one of heteroaromatic ring systems, aryloxy or heteroaryloxy groups having ⁵ to 60 atoms, each group in R may be ^substituted with one or more groups R, or any of these systems Combinations where one or more non-adjacent -CH ₂ - groups may be replaced by R ⁸ C=CR ⁸ , C≡C, Si(R ⁸ ) ₂ , Ge(R ⁸ ) ₂ , Sn(R ⁸ ) ₂ , C=O, C=S, C=Se, C=NR ⁸ , P(=O)(R ⁸ ), SO, SO ₂ , NR ⁸ , O, S or CONR ⁸ instead, and one or more of them Hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile or nitro groups, wherein two or more adjacent substituents R may be optionally joined or fused to form monocyclic or polycyclic aliphatic, aromatic or a heteroaromatic ring system, which may be substituted with one or more groups ^R8 ; Ar ¹ is the same or different at each occurrence and is selected from aromatic or heteroaromatic ring systems having 5 to 30 atoms, which may be substituted by one or more non-aromatic groups R ⁸ ; here The two groups Ar ¹ bound to the same nitrogen or phosphorus atom can also be bridged to each other by a single bond or a bridging group selected from N(R ⁸ ), C(R ⁸ ) ₂ , oxygen or sulfur; R ⁸ is selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, aliphatic hydrocarbon group with C ₁ -C ₂₀ , aromatic ring or heteroaromatic ring system with 5~30 atoms, wherein one or more hydrogen Atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R ⁸ may form with each other a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system. The triphenylene derivative according to claim 1, wherein the R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , T ¹ , and T ² are each independently selected from hydrogen, deuterium, One of C ₁ -C ₄₀ alkyl group, branched or cyclic alkyl group with C ₃ -C ₄₀ , aromatic ring system or heteroaromatic ring system with 5-60 atoms, R ¹ , R ² Each of , R ³ , R ⁴ , R ⁵ , R ⁶ , T ¹ , T ² may be substituted with one or more groups R. The triphenylene derivative according to claim 2, wherein the R is the same or different at each occurrence, and is selected from the group consisting of hydrogen atom, deuterium atom, halogen atom, nitrile group, N(Ar ¹ ) ₂ , having C ₁ - _C40 straight-chain alkyl, _C1 - _C40 straight-chain heteroalkyl, C3 _{- C40} branched or cyclic alkyl, C3 _{- C40} branched or cyclic Heteroalkyl, alkenyl or alkynyl having C ₂ -C ₄₀ , aromatic or heteroaromatic ring systems having 5 to 80, preferably 5 to 60 atoms; Ar ¹ is the same or different at each occurrence and is selected from aromatic or heteroaromatic ring systems having 5 to 30 atoms, which may be substituted by one or more non-aromatic groups R ⁸ ; here The two groups Ar ¹ bound to the same nitrogen or phosphorus atom can also be bridged to each other by a single bond or a bridging group selected from N(R ⁸ ), C(R ⁸ ) ₂ , oxygen or sulfur; R ⁸ is selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, aliphatic hydrocarbon group with C ₁ -C ₂₀ , aromatic ring or heteroaromatic ring system with 5~30 atoms, wherein one or more hydrogen Atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R ⁸ may form with each other a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system. The triphenylene derivative according to any one of claims 1 to 3, wherein the structure of the triphenylene derivative mainly includes CJHB271 to CJHB480, wherein G is selected from oxygen, sulfur, CH ₂ , C(CH ₃ ) ₂ , one of C(C ₆ H ₅ ) ₂ , N-CH ₃ , NC ₂ H ₅ , NC ₆ H ₅ :

An application of a triphenylene derivative in an organic electroluminescent material, comprising the triphenylene derivative according to any one of claims 1 to 4. The application according to claim 5, wherein the organic electroluminescent material is a material for an organic electroluminescent element, a material for an organic field effect transistor or a material for an organic thin film solar cell. An organic electroluminescence device, wherein the organic electroluminescence device comprises a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode, the at least one organic layer comprising The triphenylene derivative according to any one of claims 1 to 4. The organic electroluminescence device according to claim 7, wherein the organic layer further comprises an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light-emitting layer one of the layers. The organic electroluminescence device according to claim 8, wherein the light-emitting layer comprises a dopant and a light-emitting host, and the dopant comprises the triphenylene derivative according to any one of claims 1 to 4 The light-emitting host is the triphenylene derivative, naphthalene, anthracene, pyrene, perylene, phenanthrene, fluoranthene,

, one of benzanthracene and pentacene and their derivatives. The organic electroluminescence device according to claim 9, wherein the mass ratio of the dopant to the light-emitting host is 1:99-50:50.

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