CN111393424A - Fluoresenotrianiline compound, organic electronic device, and display device or lighting device - Google Patents

Fluoresenotrianiline compound, organic electronic device, and display device or lighting device Download PDF

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CN111393424A
CN111393424A CN202010366067.2A CN202010366067A CN111393424A CN 111393424 A CN111393424 A CN 111393424A CN 202010366067 A CN202010366067 A CN 202010366067A CN 111393424 A CN111393424 A CN 111393424A
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CN111393424B (en
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廖良生
蒋佐权
朱向东
屈扬坤
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Suzhou University
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Abstract

The invention provides a fluorene spiro triphenylamine compound, an organic electronic device, a display device or an electronic device, wherein the fluorene spiro triphenylamine compound has excellent film forming property and thermal stability by introducing a rigid structure of fluorene spiro triphenylamine, and can be used for preparing organic electroluminescent devices, organic field effect transistors and organic solar cells. The fluorene spiro triphenylamine compound of the present invention can be used as a constituent material of a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blocking layer, or an electron transport layer, and can reduce a driving voltage, improve efficiency, luminance, and lifetime. More importantly, the fluorene spiro triphenylamine compound can effectively isolate donor groups and acceptor groups, so that the fluorene spiro triphenylamine compound is an ideal framework for constructing a thermal activation delayed fluorescent material. The preparation method of the fluorene spiro triphenylamine compound is simple, the raw materials are easy to obtain, and the industrialized development requirements can be met.

Description

Fluoresenotrianiline compound, organic electronic device, and display device or lighting device
Technical Field
The invention relates to a fluorene spiro triphenylamine compound, an organic electronic device, a display device or a photo device, and belongs to the technical field of organic photoelectric materials.
Background
An organic light emitting diode (O L ED) is a self-light emitting device in which electrons injected from a cathode and holes injected from an anode are combined to form a molecular exciton at a light emitting center by applying a voltage, and the molecular exciton releases energy to emit light when returning to a ground state.
Currently commercialized organic electroluminescent materials are classified into conventional fluorescent materials and phosphorescent materials, wherein the fluorescent materials can only utilize 25% of singlet excitons, the remaining 75% of triplet excitons are lost by heat or other non-radiative means, and the phosphorescent materials can utilize 100% of excitons due to the heavy atom effect, although the luminous efficiency of the phosphorescent materials is far higher than that of the conventional fluorescent materials, most phosphorescent devices have a severe efficiency roll-off, that is, maximum efficiency at a lower luminance or a lower current density, and as the luminance or the current density increases, the external quantum efficiency of the devices generally suffers from severe reduction and is restricted by the price of precious metals. This undoubtedly increases the cost of the device, and affects the application of the organic electrophosphorescent device in illumination and full-color display.
It is a simple and practical way to improve the device efficiency and reduce the cost of organic electrophosphorescent devices by designing new thermally activated delayed fluorescence guest materials. The fluorene spiro triphenylamine compounds and the oxafluorene spiro triphenylamine compounds reported at present as guest materials can improve the device efficiency of the organic electrophosphorescent device and improve the efficiency roll-off of the device, but still have a space for further improvement.
Disclosure of Invention
The invention aims to provide a fluorene spiro triphenylamine compound, an organic electronic device, a display device or a photo device, which can effectively improve triplet state energy level, reduce the gap difference between singlet state and triplet state, and improve fluorescence quantum yield and thermal stability, thereby improving the performances of organic electroluminescent devices, such as luminous efficiency, efficiency roll-off, working voltage and the like.
In order to achieve the purpose, the invention provides the following technical scheme: a fluorene spiro triphenylamine compound, which is represented by the following general formula (1):
Figure BDA0002476783740000021
wherein R is1～R3Each independently represents cyano or optionally substituted by one or more R1Substituted, aromatic hydrocarbon radical having 6 to 30 carbon atoms or optionally substituted by one or more R1One or more substituted aromatic heterocyclic groups having 5 to 30 carbon atoms;
z represents CR1Or N;
R1represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, NO2、N(R2)2、OR2、SR2、C(＝O)R2、P(＝O)R2、Si(R2)3One or more of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 40 carbon atoms;
R2represents one or more of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms.
Further, said R1、R2And R3Each independently selected from cyano or any one of the following general formulae Ar-1 to Ar-39:
Figure BDA0002476783740000031
wherein, the wavy line represents a bond bonded with the mother nucleus of the fluorenylspirotriphenylamine,
R1have the meaning as defined in claim 1.
Further, R1And R2Represents one or more of phenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzothienocarbazole, benzofurocarbazole, benzofluorenocarbazole, benzanthracene, triphenylene, fluorenyl, spirobifluorenyl, triazinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, indenocarbazolyl, benzimidazolyl, diphenyl-oxadiazolyl, diphenylboryl, triphenylphosphinyl, diphenylphosphinyloxy, triphenylsilyl or tetraphenylsilyl.
Further, the fluorene spiro triphenylamine compound is selected from any one of the following general formulas 1-1 to 1-40:
Figure BDA0002476783740000051
Figure BDA0002476783740000061
the invention also provides a preparation method of the fluorene spiro triphenylamine compound, which comprises the following steps:
the R is introduced by the metal-catalyzed coupling reaction or the nucleophilic reaction of a lithium reagent of the fluorene spirotriphenylamine functionalized at the 2,4 and 7 positions1、R2And R3A group.
The invention also provides application of the fluorene spiro triphenylamine compound in preparing electronic devices, wherein the electronic devices are selected from organic electroluminescent devices, organic field effect transistors or organic solar cells, and especially application of luminescent guest materials, luminescent host materials, exciton blocking materials or electron transport materials in preparing organic electroluminescent devices.
The invention also provides an electronic device which is provided with the fluorene spiro triphenylamine compound.
Further, the electronic device is an organic electroluminescent device, the organic electroluminescent device comprises an organic light emitting layer, an exciton blocking layer and an electron transmission layer, and the organic electroluminescent device is provided with the fluorene spiro triphenylamine compound.
Compared with the prior art, the invention has the beneficial effects that: the fluorene spiro triphenylamine compound has excellent film forming property and thermal stability by introducing the rigid structure of the fluorene spiro triphenylamine, and can be used for preparing organic electroluminescent devices, organic field effect transistors and organic solar cells. The fluorene spiro triphenylamine compound of the present invention can be used as a constituent material of a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blocking layer, or an electron transport layer, and can reduce a driving voltage, improve efficiency, luminance, and lifetime. More importantly, the fluorene spiro triphenylamine compound can effectively isolate donor groups and acceptor groups, so that the fluorene spiro triphenylamine compound is an ideal framework for constructing a thermal activation delayed fluorescent material. The preparation method of the fluorene spiro triphenylamine compound is simple, the raw materials are easy to obtain, and the industrialized development requirements can be met.
The foregoing description is only an overview of the technical solutions of the present invention, and in order to make the technical solutions of the present invention more clearly understood and to implement them in accordance with the contents of the description, the following detailed description is given with reference to the preferred embodiments of the present invention and the accompanying drawings.
Drawings
FIG. 1 shows the ultraviolet absorption spectrum (UV-Vis), the room temperature fluorescence spectrum (P L) and the low temperature phosphorescence spectrum (Phos) of compounds 1 to 25 in example 5 of the present invention;
FIG. 2 is a graph showing the organic electroluminescence spectrum of an O L ED device in example 7 of the present invention.
Detailed Description
The following detailed description of embodiments of the present invention is provided in connection with the accompanying drawings and examples. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The invention provides a fluorene spiro triphenylamine compound, which is a compound containing a general formula (1) as follows:
Figure BDA0002476783740000081
wherein R is1～R3Each independently represents a hydrogen atom, a cyano group or optionally substituted by one or more R1Substituted, aromatic hydrocarbon radical having 6 to 30 carbon atoms or optionally substituted by one or more R1One or more substituted aromatic heterocyclic groups having 5 to 30 carbon atoms;
z represents CR1Or N;
R1represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, NO2、N(R2)2、OR2、SR2、C(＝O)R2、P(＝O)R2、Si(R2)3Substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkyl having 2 to 20 carbon atomsOne or more of a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 40 carbon atoms;
R2represents one or more of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms.
<R1And R3>
R1～R3Each independently represents a hydrogen atom, a cyano group or optionally substituted by one or more R1Substituted, aromatic hydrocarbon radical having 6 to 30 carbon atoms or optionally substituted by one or more R1One or more substituted aromatic heterocyclic groups having 5 to 30 carbon atoms.
From R1～R3The aromatic hydrocarbon group having 6 to 30 carbon atoms or the aromatic heterocyclic group having 5 to 30 carbon atoms represented may be exemplified by: phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, perylenyl, fluoranthenyl, benzofluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, biphenylyl, terphenyl, quaterphenyl, pentabiphenyl, terphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, hydropyranyl, cis-or trans-indenofluorenyl, cis-or trans-monobenzindenofluorenyl, cis-or trans-dibenzoindenofluorenyl, trimeric indenyl, isotridecyl, spirotrimeric indenyl, spiroisotridecyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, benzothienyl, benzothiophenocarbazolyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, indolocarbazolyl, indenocarbazolyl, pyridyl, bipyridyl, perylenyl, pyranthrylyl, benzopyrenyl, pentacenyl, benzopyrenyl, terphenyl, Terpyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, phenothiazineA group selected from the group consisting of a phenoxazinyl group, a pyrazolyl group, an indazolyl group, an imidazolyl group, a benzimidazolyl group, a naphthoimidazolyl group, a phenanthroimidazolyl group, a pyridoimidazolyl group, a pyrazinoimidazolyl group, a quinoxalinyl group, an oxazolyl group, a benzoxazolyl group, a benzooxadiazolyl group, a naphthooxazolyl group, an anthraoxazolyl group, a phenanthrooxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a benzothiadiazolyl group, a pyridazinyl group, a benzopyrazinyl group, a pyrimidinyl group, a benzopyrimidinyl group, a quinoxalinyl group, a quinazolinyl group, an azafluorenyl group, a diazenanthranyl group, a pyrenyl group, a tetraazaperylenyl group, a naphthyridinyl group, a pyrazinyl group, a phenoxazinyl group, a phenothiazinyl group, a fluorescenzinyl group, a naphthyridinyl group, an azacarbazolyl group, a benzocarbazinyl group, a phenanthrolin, Pteridinyl, indolizinyl, benzothiadiazolyl, pyridopyrrolyl, pyridotriazolyl, xanthenyl, benzofurocarbazolyl, benzofluorenocarbazolyl, N-phenylcarbazolyl, diphenyl-benzimidazolyl, diphenyl-oxadiazolyl, diphenyl boron, triphenylphosporyl, diphenylphosphinyloxy, triphenylsilyl, tetraphenylsilyl, and the like.
In the present invention, preferably, R1～R3Each independently selected from a hydrogen atom, a cyano group or the following group:
Figure BDA0002476783740000101
wherein the wavy line represents a bond to the parent nucleus, R1Have the meaning defined above.
From R1～R3The aromatic hydrocarbon group having 6 to 30 carbon atoms or the aromatic heterocyclic group having 5 to 30 carbon atoms represented may be unsubstituted, but may also have a substituent. Preferably, from Ar1～Ar6The aromatic hydrocarbon group having 6 to 30 carbon atoms or the aromatic heterocyclic group having 5 to 30 carbon atoms represented by1Substituted, aromatic hydrocarbon radicals having 5 to 30 carbon atoms or substituted by one or more R1Substituted byAnd an aromatic heterocyclic group having 5 to 30 carbon atoms.
<R1>
R1Represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, NO2、 N(R2)、OR2、SR2、C(＝O)R2、P(＝O)R2、Si(R2)3One or more of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 40 carbon atoms.
From R1The alkyl group having 1 to 20 carbon atoms represented may be exemplified by: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, 2-methylhexyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, 3-methylheptyl, n-nonyl, n-decyl, hexadecyl, octadecyl, eicosyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like. The alkyl group having 1 to 20 carbon atoms may be linear, branched or cyclic.
From R1The alkyl group having 1 to 20 carbon atoms represented may be unsubstituted, but may also have a substituent. Preferably, from R1Alkyl having 1 to 20 carbon atoms represented by one or more of the following R2And (4) substitution. In addition, one or more non-adjacent CH in the alkyl group2The group can be represented by R2C＝CR2、C≡C、Si(R2)3、C＝O、 C＝NR2、P(＝O)R2、SO、SO2、NR2O, S or CONR2And wherein one or more hydrogen atoms may be replaced by deuterium atoms, fluorine atomsChlorine atom, bromine atom, iodine atom, cyano-group and nitro-group.
From R1The alkenyl group having 2 to 20 carbon atoms represented may be exemplified by: vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, 2-ethylhexenyl, allyl, cyclohexenyl and the like. The alkenyl group having 2 to 20 carbon atoms may be linear, branched or cyclic.
From R1The alkenyl group having 2 to 20 carbon atoms represented may be unsubstituted or may have a substituent. The substituents can be exemplified by the group consisting of R1The alkyl group having 1 to 20 carbon atoms represented by (b) may have the same substituent as that represented by the substituent(s). The substituents may take the same pattern as that of the exemplary substituents.
From R1The alkynyl group having 2 to 20 carbon atoms represented may be exemplified by: ethynyl, isopropynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl and the like.
From R1The alkynyl group having 2 to 20 carbon atoms represented may be unsubstituted or may have a substituent. The substituents can be exemplified by the group consisting of R1The alkyl group having 1 to 20 carbon atoms represented by (b) may have the same substituent as that represented by the substituent(s). The substituents may take the same pattern as that of the exemplary substituents.
From R1The aromatic hydrocarbon group having 6 to 40 carbon atoms or the aromatic heterocyclic group having 5 to 40 carbon atoms represented by the above formula may be exemplified by the group consisting of Ar1～Ar6The aromatic hydrocarbon group having 6 to 30 carbon atoms or the aromatic heterocyclic group having 5 to 30 carbon atoms represented by the above formula represent the same groups.
From R1The aromatic hydrocarbon group having 6 to 40 carbon atoms or the aromatic heterocyclic group having 5 to 40 carbon atoms represented may be unsubstituted or may have a substituent. The substituents may beBy way of illustration with R1The alkyl group having 1 to 20 carbon atoms represented by (b) may have the same substituent as that represented by the substituent(s). The substituents may take the same pattern as that of the exemplary substituents. In addition, two adjacent R1Substituents or two adjacent R2The substituents optionally may form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more R2Substitution; where two or more substituents R1May be connected to each other and may form a ring.
Preferably represented by R1The aromatic hydrocarbon group having 6 to 40 carbon atoms or the aromatic heterocyclic group having 5 to 40 carbon atoms represented by (a) may be exemplified by: phenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzothienocarbazolyl, benzofurocarbazolyl, benzofluorenocarbazolyl, benzanthracenyl, benzophenanthryl, fluorenyl, spirobifluorenyl, triazinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, indenocarbazolyl, benzimidazolyl, diphenyl-oxadiazolyl, diphenyl boron, triphenyl phosphoxy, diphenyl phosphoxy, triphenyl silicon group, tetraphenyl silicon group, and the like. The aromatic hydrocarbon group having 6 to 40 carbon atoms or the aromatic heterocyclic group having 5 to 40 carbon atoms may be substituted with one or more R2And (4) substitution.
<R2>
R2Represents one or more of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms.
From R2The alkyl group having 1 to 20 carbon atoms represented by R1The alkyl groups represented by the formulae having 1 to 20 carbon atoms represent the same groups.
From R2An aromatic hydrocarbon group having 6 to 30 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group having 5 to 30 carbon atomsExamples of the aromatic heterocyclic group include those represented by the formula R1The same groups as those shown for the aromatic hydrocarbon group having 6 to 30 carbon atoms or the substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms.
From R2The alkyl group having 1 to 20 carbon atoms, the aromatic hydrocarbon group having 6 to 30 carbon atoms, or the substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms represented may be unsubstituted, or may also have a substituent. The substituents may be exemplified by: a deuterium atom; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; cyano, and the like.
<Z>
Z represents CR1Or N, e.g. N, C-H, C-F, C-Cl, C-Br, C-I, C-CN, C-NO2Carbon-phenyl, carbon-biphenyl, and the like.
R1Have the meaning as defined above.
In a particularly preferred embodiment of the invention:
wherein R is1、R2And R3Each independently selected from cyano or the following aromatic or heteroaromatic ring systems: pyridyl, diphenylamino, dimethylboryl, diphenyltriazinyl; the aromatic or heteroaromatic ring system may be substituted by one or more R1Substitution;
r at each position1The groups are independently selected from: hydrogen, linear alkyl having 1 to 5C atoms.
Preferably, the fluorene spiro triphenylamine compound is selected from any one of the following general formulas 1-1 to 1-40:
Figure BDA0002476783740000141
Figure BDA0002476783740000151
the invention also provides a preparation method of the fluorene spiro triphenylamine compound, which comprises the following steps:
the compounds according to the invention can be prepared by synthetic procedures known to those of ordinary skill in the art, such as bromination, Suzuki coupling, buhward-Hartwig coupling, etc.
The compound synthesis of the present invention generally starts with a fluorene spirotriphenylamine compound functionalized at the 2,4 and 7 positions, and then introduces R by a lithium reagent nucleophilic reaction or a metal catalyzed coupling reaction such as Suzuki coupling or Buhward-Hardwig-Buchwald coupling1、R2And R3A group.
In a preferred embodiment of the present invention, the fluorene spirotriphenylamine compound is a compound functionalized with a boric acid compound, and R is1、R2And R3The groups are derived from halogen functionalized compounds. In another preferred embodiment of the present invention, the fluorene spiro triphenylamine compound is a halogen-functionalized compound, and R R1、R2And R3The group is derived from a compound functionalized with a boronic acid compound.
In a third preferred embodiment of the present invention, the fluorene spiro triphenylamine compound is a halogen-functionalized compound, and is reacted with an amine compound under the action of a palladium catalyst to introduce R1、R2And R3A group. Among these, halogen functionalization is preferably bromination, chlorination, iodination, and particularly bromination.
In a fourth preferred embodiment of the present invention, the fluorene spiro triphenylamine compound is a halogen-functionalized compound, and is reacted with a phosphorus-based or silicon-based or boron-based compound under the action of a lithium reagent to introduce R1、R2And R3A group. Among these, halogen functionalization is preferably bromination, chlorination, iodination, and particularly bromination.
Specifically, as described above for the first preferred embodiment, a boronic acid functionalized fluorene spiro triphenylamine compound (intermediate M3) is prepared, and preferred preparation steps are exemplified as follows:
Figure BDA0002476783740000161
by controlling the reaction conditions, the yield of M1 can reach 80-92%, the yield of M2 can reach 60-80%, and the yield of M3 can reach 70-85%. After obtaining intermediate M3, an optional R is added to the system1、R2And R3Halogen functional compounds of the group such as 2, 4-dichloro-6-phenyl-1, 3, 5-triazine or melamine, and a certain amount of palladium catalyst such as tetrakis (triphenylphosphine palladium), anhydrous potassium carbonate, tetrahydrofuran and water, are reacted under nitrogen protection at 50-80 ℃ for 30-35 hours, and the reaction is completed. Evaporating the solvent, dissolving the residue with dichloromethane and water, washing with water, separating organic layer, extracting water layer with dichloromethane, mixing organic layers, washing with water twice to neutrality, evaporating to remove solvent, separating by column chromatography, and drying to obtain the product. The molar ratio of intermediate M3 to tetrakis (triphenylphosphine palladium) is in the range of 15-20:1, preferably 18: 1; by adjusting the reaction conditions, the yield is 65-85%.
In the second preferred embodiment, as mentioned above, preferably using M2 and the compound pyridine-3-boric acid functionalized by boric acid compound to react, adding tetrakis (triphenylphosphine) palladium, anhydrous potassium carbonate, tetrahydrofuran and water into the system, and reacting for 30-35 hours at 50-80 ℃ under the protection of argon, and finishing the reaction. The post-treatment is the same as in the first preferred embodiment. The final product yield can reach 79 percent.
In the third preferred embodiment, M2 is preferably reacted with diphenylamine functionalized by amine compounds, and tris (dibenzylideneacetone) dipalladium, sodium tert-butoxide, tri-tert-butylphosphine tetrafluoroborate and toluene are added into the system, and the reaction is completed at 90-120 ℃ for 10-30 hours under the protection of argon. And (4) carrying out suction filtration, decompressing, steaming to remove the solvent, carrying out column chromatography separation, and drying to obtain the product. The molar ratio of intermediate M2 to tris (dibenzylideneacetone) dipalladium is 15-20:1, preferably 18: 1; by adjusting the reaction conditions, the yield can reach 78%.
As described above in the fourth preferred embodiment, it is preferable to dissolve M2 in tetrahydrofuran, add n-butyllithium dropwise at low temperature, stir at-78 ℃ for 1 hour, then slowly add a boron-functionalized compound such as bis (trimethylphenyl) boron fluoride dissolved in tetrahydrofuran dropwise into a reaction flask, automatically raise the temperature after 1 hour, and react overnight. Adding a small amount of water into a reaction bottle to quench the reaction, evaporating the solvent under reduced pressure, carrying out column chromatography separation, and drying to obtain the product, wherein the yield can reach 78%.
The invention also provides application of the fluorene spiro triphenylamine compound in preparing electronic devices, wherein the electronic devices are selected from organic electroluminescent devices, organic field effect transistors or organic solar cells, and especially application of luminescent host materials, exciton blocking materials or electron transport materials in preparing organic electroluminescent devices.
The electronic device is preferably selected from organic electroluminescent devices (organic light emitting diodes, O L ED), organic field effect transistors (O-FETs), organic solar cells (O-SCs), organic thin film transistors (O-TFTs), organic light emitting transistors (O-L ET), organic integrated circuits (O-ICs), Organic Dye Sensitized Solar Cells (ODSSC), organic optical detectors, organic photoreceptors, organic field quenching devices (O-FQD), light emitting electrochemical cells (L EC), organic laser diodes (O-lasers), organic plasma emitting devices and the like, preferably organic electroluminescent devices (O L ED).
An O L ED generally includes a substrate such as, but not limited to, glass, plastic, metal, an anode such as an Indium Tin Oxide (ITO) anode, a hole injection layer (HI L), a hole transport layer (HT L), an electron blocking layer (EB L), an organic light emitting layer (EM L), an exciton blocking layer (EB L), an electron transport layer (ET L), an electron injection layer (EI L) such as L iq, Cs2CO3(ii) a A cathode, such as Al. However, it should be noted that there may be one or more layers per layer in between and that each layer need not be present.
The compounds of the present invention can be used in any one or more layers of the device, but are preferably used in the light emitting layer (EM L), more preferably the host material of the light emitting layer, because they have high triplet energy levels and good stability.
The organic light-emitting layer dopant of the present invention is not particularly limited, and is preferably a light-emitting metal complex, preferably a complex of iridium and platinum, and a light-emitting organic molecule, preferably a fluorescent compound and a thermally-excited delayed fluorescence compound. In order to improve the device performance, the mass ratio of the dopant is 6% to 30%, preferably 6% to 20%, and more preferably 6% to 15%.
In a preferred embodiment of the invention, O L ED comprises a substrate/anode/hole injection material (HI L)/hole transport material (HI L)/electron blocking layer (EB L)/organic light emitting layer (EM L)/electron transport layer (ET L)/cathode, wherein the substrate uses a glass substrate and ITO as anode material, the hole injection material uses 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN) commonly used in the prior art, the hole transport material uses 4,4' - (cyclohexane-1, 1-diyl) bis (N, N-di-p-Tolylaniline) (TAPC) commonly used in the prior art, the electron blocking layer uses tris (4- (9H-carbazol-9-yl) phenyl) amine (TCTA) commonly used in the prior art, the organic light emitting layer uses the compound of the invention doped with the host material 9,9' - (1, 3-phenyl) di-9H-carbazole (mCP) and 4' -biphenyl (9H-8-hydroxy-quinoline [ 8 ] also can be used as the electron transport material, the electron blocking layer, the compound of the prior art, or the compound of the prior art doped with the compound of the present invention doped with the present invention]Quinoline) beryllium (Be (bq)2) And tris (8-hydroxyquinoline) aluminum (Alq)3) The cathode has a structure of metal and its mixture, such as Mg: Ag, Ca: Ag, etc., or an electron injection layer/metal layer structure, such as L iF/Al, L iq/Al and L i2O/Al. the preferred electron injecting material of the present invention is L iq and the cathode material is Al.
The present invention is described below by referring to examples, and those skilled in the art will understand that the examples are only illustrative and not exhaustive, and that the preparation examples are compound synthesis examples, the chemical raw materials and reagents involved are all commercially available or synthesized according to the published literature, and the example is the preparation of a light emitting device O L ED.
Preparation examples
Synthesis of intermediate M3
The structural formula and the synthetic route of the intermediate M3 are shown as the following formula:
Figure BDA0002476783740000191
the compound of formula M1 is prepared by dissolving 1.6g (6.2mmol) of 4-bromo-fluorenone in 50M L dichloromethane in a 100M L two-neck flask, stirring in an ice bath, adding 0.67M L (12.8mmol) of liquid bromine dropwise through a constant pressure dropping funnel, gradually heating the system to room temperature after the addition is completed, reacting for 6 hours, pouring the reaction solution into a saturated sodium bisulfite solution after the reaction is completed, extracting with dichloromethane for 3 times, drying the organic phase with anhydrous sodium sulfate, and removing the solvent by spin-drying to obtain a crude product, separating and purifying the crude product on a silica gel column with an eluent of dichloromethane to petroleum ether (1: 5) (by volume) to obtain 2.3g M1 with a yield of 90%. MS (ei): M/z 417.05[ M (EI)+]. Calculated value of elemental analysis C13H5Br3O (%): c37.45, H1.21; measured value: c37.411.20
The compound of formula M2 is prepared by dissolving 1.6 (4.9mmol) 2-bromo-triphenylamine in 30M L anhydrous tetrahydrofuran in a 100M L two-necked flask under nitrogen protection, stirring, cooling to-78 deg.C, adding 2.3M L0 (5.5mmol)2.4M n-butyllithium dropwise to the solution via a constant pressure dropping funnel, stirring at-78 deg.C for 1 hour, dispersing 2.0g (4.9mmol) M1 in 30M L anhydrous tetrahydrofuran under nitrogen protection, adding dropwise to the reaction mixture, after completion of 865, gradually raising to room temperature, reacting for 12 hours, quenching with 5M L water after completion of the reaction, removing tetrahydrofuran by spin drying, dissolving the crude product in 150M L dichloromethane, washing with 60M L water for 3 times, removing the solvent to obtain crude product, heating the crude product to room temperature, adding dichloromethane to obtain dichloromethane, stirring to obtain intermediate product, heating the intermediate, stirring to room temperature, purifying, adding the intermediate product to obtain silica gel column, heating to obtain silica gel column, eluting with dichloromethane, drying, eluting with 300M 3625, filtering to obtain silica gel column, purifying, adding the crude product, filtering to obtain silica gel column, heating to obtain silica gel column, eluting with dichloromethane, eluting with 300M 3625, filtering to obtain silica gel column, eluting, filtering to obtain silica gel column, and filtering to obtain silica gel column, eluting with 5M 3, filtering to obtain silica gel column, eluting, filtering to obtain silica gel column, filteringMethane: petroleum ether is 1: 4 (volume ratio) eluent is separated and purified on a silica gel column to obtain 2.2g M2 with the yield of 70%. MS (EI) M/z 644.54[ M ]+]. Calculated value of elemental analysis C31H18Br3N (%): c57.80, H2.82, N2.17; measured value: c57.60, H2.80, N2.15.
The intermediate M3 is prepared by charging 2.0g M2(3.05mmol) and 50M L tetrahydrofuran in a 100M L Schlenk reaction flask under the protection of argon gas, dissolving, cooling, dropping 2.4M n-butyllithium 1.3M L (3.2mmol) at-78 deg.C, stirring for 1 hour, dropping 0.8 g (4.5mmol) triisopropyl borate, stirring for 1 hour, automatically heating, reacting overnight, adding 10M L ammonium chloride aqueous solution, quenching, transferring the reaction mass to a single-neck flask, distilling off the solvent under reduced pressure, adding 80M L dichloromethane and 80M L water in the flask, dissolving, washing with water, layering, extracting the aqueous layer with 15M L dichloromethane twice, combining the organic phases, washing with 80M L water twice, neutralizing, removing the aqueous layer, adding 15g anhydrous sodium sulfate to the organic layer, drying for 3 hours, distilling off the solvent under reduced pressure to obtain 1.3g white solid MS, obtaining yield 80M 8632M 539.19M 36z: (M.3M)+]. Calculated value of elemental analysis C31H24B3NO6(%): c69.08, H4.49, N2.60; measured value: c68.95, H4.40, N2.58.
Example 1
The structural formulas and synthetic routes of the compounds 1-27 are shown as follows:
Figure BDA0002476783740000201
under the protection of nitrogen, 1.6g (2.5mmol) of M2, 1.11 g (9mmol) of pyridine-3-boric acid, toluene 50M L, ethanol 10M L, 2M aqueous sodium carbonate solution 10M L and tetrakistriphenylphosphine palladium 0.15g (1.25mmol) are sequentially added into a 100M L two-neck flask, stirred and heated to 106 ℃ for reaction for 24 hours, after the reaction is completed, the reaction system is cooled to room temperature, dichloromethane is used for extraction for three times, an organic phase is dried by anhydrous sodium carbonate and then is spin-dried to remove the solvent, a crude product is obtained, and the crude product is eluted by dichloromethane, petroleum ether and the volume ratio of the eluent is 7: 3 (dichloromethane: petroleum ether)Separation and purification are carried out on a triethylamine basified silica gel column to obtain 1.3g of 1-27 with the yield of 79%. MS (EI) M/z 638.52[ M ]+]. Calculated value of elemental analysis C46H30N4(%): c86.49, H4.73, N8.77; measured value: c86.39, H4.70, N8.72.
Example 2
The structural formulas and synthetic routes of the compounds 1-28 are shown as follows:
Figure BDA0002476783740000211
under the protection of nitrogen, 1.6g (2.5mmol) of M2, 1.11 g (3mmol) of pyridine-4-boric acid, toluene 50M L, ethanol 10M L, 2M aqueous sodium carbonate solution 10M L and tetrakistriphenylphosphine palladium 0.15g (1.25mmol) are sequentially added into a 100M L two-neck flask, stirred and heated to 106 ℃ for reaction for 24 hours, after the reaction is completed, the reaction system is cooled to room temperature, dichloromethane is used for extraction for three times, an organic phase is dried by anhydrous sodium carbonate and then is spin-dried to remove the solvent, a crude product is obtained, and the crude product is separated and purified on an alkalized silica gel column by triethylamine by using an eluent of dichloromethane to petroleum ether (volume ratio) to obtain 1.3g of 1-28, wherein the yield is 79%. MS (EI): M/z 638.52[ M3-28 (volume ratio)+]. Calculated value of elemental analysis C46H30N4(%): c86.49, H4.73, N8.77; measured value: c86.38, H4.68, N8.70.
Example 3
The structural formulas and the synthetic routes of the compounds 1-6 are shown as follows:
Figure BDA0002476783740000212
under the protection of nitrogen, 1.4g (2.5mmol) of M3, 2.4g (7.8mmol) of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, 50M L of toluene, 10M L of ethanol, 10M L of 2M sodium carbonate aqueous solution and 0.15g (1.25mmol) of palladium tetratriphenylphosphine are sequentially added into a 100M L two-mouth bottle, stirred and heated to 106 ℃ for 24 hours to react, after the reaction is completed, the reaction system is cooled to room temperature, extracted with dichloromethane for three times, an organic phase is dried by anhydrous sodium carbonate and then spin-dried to remove the solvent, and the organic phase is obtainedTo crude product, crude product was purified with dichloromethane: petroleum ether is 7: 3 vol% of eluent was applied to silica gel column for separation and purification to obtain 2.2g of 1-6 in 79% yield. MS (EI) M/z 1100.25[ M ]+]. Calculated value of elemental analysis C76H48N10(%): c82.89, H4.39, N12.72; measured value: c82.80, H4.37, N12.74.
Example 4
The structural formulas and the synthetic routes of the compounds 1 to 10 are shown as follows:
Figure BDA0002476783740000221
dissolving 3.1g (4.9mmol) of M2 in 30M L anhydrous tetrahydrofuran in a 100M L two-necked flask under nitrogen, stirring, cooling to-78 deg.C, adding 2.3M L (5.5mmol) of 2.4M n-butyllithium dropwise to the solution via a constant-pressure dropping funnel, stirring at-78 deg.C for 1 hour, dispersing 3.9g (14.7mmol) of bis (trimethylphenyl) boron fluoride in 30M L anhydrous tetrahydrofuran under nitrogen, adding dropwise to the reaction mixture, gradually raising to room temperature, quenching the reaction for 12 hours after the reaction is complete, removing tetrahydrofuran by spin-drying, dissolving the crude product in 150M L dichloromethane, washing 3 times with 60M L water, removing the solvent by spin-drying to obtain the crude product, eluting with dichloromethane, petroleum ether (3: 1) (volume ratio: 1), purifying the crude product by silica gel column chromatography at EI/75M 36z, eluting with 75M silica gel column, (1151.69M) to obtain EI 75%, (III)+]. Calculated value of elemental analysis C85H84B3N (%): c88.62, H7.35, N1.22; measured value: c88.50, H7.30, N1.20.
Example 5
The structural formulas and the synthetic routes of the compounds 1 to 25 are shown as follows:
Figure BDA0002476783740000231
in a 100M L two-necked flask, 3.1g (4.9mmol) of M2, 1.5g (15.3 mmol) of cuprous cyanide were placed under nitrogenDissolving in 40M L N, N-dimethylformamide, stirring, heating to 150 deg.C, reacting for 24 hr, pouring the reaction solution into 50M L saturated sodium hydroxide solution, suction filtering to obtain crude product, dissolving in 150M L dichloromethane and washing with 60M L water 3 times, drying the organic phase with anhydrous sodium sulfate, removing solvent by rotary drying to obtain crude product, separating and purifying the crude product on silica gel column with dichloromethane and petroleum ether at volume ratio of 3: 2 to obtain 1.8g 1-25, and obtaining 77% yield of MS (EI) M/z 482.36[ M/z 482.36 (M/z 482.36) ]+]. Calculated value of elemental analysis C34H18N4(%): c84.63, H3.76, N11.61; measured value: c84.47, H3.71, N11.50.
Referring to FIG. 1, FIG. 1 shows the UV absorption spectra, UV-Vis absorption spectra (UV-Vis), room temperature fluorescence spectra (P L), and low temperature phosphorescence spectra (Phos) of products 1-25 in dilute solutions of dichloromethane and toluene, respectively (1 × 10)-5mol/L), low temperature phosphorescence spectrum in toluene solution (1 × 10)-3mol/L).
Example 6
The structural formulas and synthetic routes of the compounds 1-32 are shown as follows:
Figure BDA0002476783740000232
1.5g (2.3mmol) of M2, 1.5g (8.9mmol) of diphenylamine, 0.3g (2.9mmol) of sodium tert-butoxide, 0.1g (0.3mmol) of tri-tert-butylphosphine tetrafluoroborate and 0.27 g (0.3mmol) of tris (dibenzylideneacetone) dipalladium are sequentially added into a 250M L two-neck flask, the reaction system is degassed, 150M L of toluene is added under the protection of nitrogen, stirring and heating are carried out to 106 ℃ for reaction for 12 hours, after the reaction is completed, the system is cooled to room temperature, reduced pressure suction filtration is carried out, a large amount of dichloromethane is used for washing filter residue, the filtrate is concentrated to obtain a crude product, and the crude product is separated and purified on a silica gel column by using an eluent of petroleum ether, dichloromethane is 2: 3 (volume ratio), so that 1.9g of 1-32 of a target product is obtained, and the yield is 92%. MS/M/z (M) 908.30[ M908.30+]. Calculated value of elemental analysis C67H48N4(％)：C 88.52，H 5.32，N6.16; measured value: c88.45, H5.30, N6.13.
Device embodiments
Examples 7 to 15
The preparation of the device comprises the steps of carrying out ultrasonic treatment on a glass plate coated with an ITO transparent conductive layer in a commercial cleaning agent, washing the glass plate in deionized water, washing the glass plate in acetone and ethanol for three times respectively, baking the glass plate in a clean environment until the moisture is completely removed, washing the glass plate by using ultraviolet light and ozone, bombarding the surface by using low-energy cation beams, putting the ITO conductive glass into a vacuum chamber, and vacuumizing the vacuum chamber to 2 × 10-5-2×10-5Pa. A hole injection material (HI L), a hole transport material (HI L), an electron blocking layer (EB L), an organic luminescent layer (EM L), an electron transport layer (ET L) and a cathode are sequentially evaporated on the ITO conductive glass, wherein the evaporation rate of the organic material is 0.2nm/s, the evaporation rate of the metal electrode is more than 0.5nm/s, the luminescent layer is evaporated by a double-source co-evaporation method, the evaporation rate of the host material is 0.2nm/s, and the evaporation rate of the doping material is 0.03 nm/s.
Testing the performance of the device: the current-luminance-voltage characteristics of the device were obtained from a Keithley source measuring system (Keithley 2400Sourcemeter, Keithley 2000Currentmeter) with calibrated silicon photodiodes, the electroluminescence spectra were measured by a Photo research PR655 spectrometer, and the external quantum efficiencies of the devices were calculated by the method of the documents adv.mater, 2003,15, 1043-. All devices were encapsulated in a nitrogen atmosphere.
The examples relate to compounds having the following structure:
Figure BDA0002476783740000251
the structures of examples 7-12 (devices O L ED1-6, respectively) and the film thicknesses of the respective layers were as follows:
OLED1：
ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/2wt％1-25:CBP(15 nm)/TmPyPB(50nm)/Liq(2nm)/Al(120nm)。
OLED2：
ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/2wt％1-10:CBP(15 nm)/TmPyPB(50nm)/Liq(2nm)/Al(120nm)。
OLED3：
ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/2wt％1-27:CBP(15 nm)/TmPyPB(50nm)/Liq(2nm)/Al(120nm)。
OLED4：
ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/2wt％1-28:CBP(15 nm)/TmPyPB(15nm)/Liq(2nm)/Al(120nm)。
OLED5：
ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/2wt％1-32:CBP(15 nm)/TmPyPB(50nm)/Liq(2nm)/Al(120nm)。
OLED6：
ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/2wt％1-6:CBP(15 nm)/TmPyPB(50nm)/Liq(2nm)/Al(120nm)。
comparative example
The preparation method of comparative example 1 is the same as that of the example, only the guest material is changed, and the device structure of comparative example 1 is as follows:
ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/2wt％ACRFLCN:CBP(15 nm)/TmPyPB(50nm)/Liq(2nm)/Al(120nm)。
the device performance data is shown in table 1:
table 1: device performance data
Figure BDA0002476783740000261
As can be seen from table 1, the compounds of the invention gave very good performance data. Comparative example 1 and example 7 use CBP as the host material, except that the guest material of example 7 is the compounds 1 to 25 of the present invention, and it can be seen from the comparison of the device performance data that example 7 has a lower operating voltage and a higher external quantum efficiency, and the device attenuation is significantly improved. Referring to fig. 2, the organic electroluminescence spectrum of example 7 is shown, which shows a strong luminescence intensity and sufficient energy transfer from the host material to the guest material. Therefore, compared with the materials commonly used in the prior art, the compound provided by the invention can effectively reduce the working voltage, improve the external quantum efficiency and improve the efficiency attenuation problem of the device.
In summary, the following steps: the fluorene spiro triphenylamine compound has excellent film forming property and thermal stability by introducing the rigid structure of the fluorene spiro triphenylamine, and can be used for preparing organic electroluminescent devices, organic field effect transistors and organic solar cells. The fluorene spiro triphenylamine compound of the present invention can be used as a constituent material of a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blocking layer, or an electron transport layer, and can reduce a driving voltage, improve efficiency, luminance, and lifetime. More importantly, the fluorene spiro triphenylamine compound can effectively isolate donor groups and acceptor groups, so that the fluorene spiro triphenylamine compound is an ideal framework for constructing a thermal activation delayed fluorescent material. The preparation method of the fluorene spiro triphenylamine compound is simple, the raw materials are easy to obtain, and the industrialized development requirements can be met.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.

Claims (8)

1. A fluorene spiro triphenylamine compound, which is represented by the following general formula (1):
Figure FDA0002476783730000011
wherein R is1、R2And R3Each independently selected from cyano, or optionally substituted by one orPlural R1Substituted, aromatic hydrocarbon radical having 6 to 30 carbon atoms, or optionally substituted by one or more R1One or more substituted aromatic heterocyclic groups having 5 to 30 carbon atoms;
z represents CR1Or N;
R1represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, NO2、N(R2)2、OR2、SR2、C(＝O)R2、P(＝O)R2、Si(R2)3One or more of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 40 carbon atoms;
R2represents one or more of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms.
2. The fluorene spirotriphenylamine compound according to claim 1, wherein R is1、R2And R3Each independently selected from cyano or any one of the following general formulae Ar-1 to Ar-39:
Figure FDA0002476783730000021
wherein, the wavy line represents a bond bonded with the mother nucleus of the fluorenylspirotriphenylamine,
R1have the meaning as defined in claim 1.
3. A fluorenylspirotriphenylamine compound according to claim 1 or 2, wherein R is1And R2Represents one or more of phenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzothienocarbazole, benzofurocarbazole, benzofluorenocarbazole, benzanthracene, triphenylene, fluorenyl, spirobifluorenyl, triazinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, indenocarbazolyl, benzimidazolyl, diphenyl-oxadiazolyl, diphenylboryl, triphenylphosphinyl, diphenylphosphinyloxy, triphenylsilyl or tetraphenylsilyl.
4. The fluorene spirotriphenylamine compound according to claim 1 or 2, wherein the fluorene spirotriphenylamine compound is selected from any one of the following chemical formulae 1-1 to 1-40:
Figure FDA0002476783730000041
Figure FDA0002476783730000051
5. an organic electronic device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and at least one organic layer interposed between the first electrode and the second electrode, the at least one organic layer containing the compound according to any one of claims 1 to 4.
6. The organic electronic device according to claim 5, wherein the organic layer is composed of one or more of a light emitting material, a sensitizing material, and a host material, and the compound is any one or more of the light emitting material, the sensitizing material, or the host material.
7. The organic electronic device according to claim 5, wherein the organic layer comprises one or more layers of a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, and an electron injection layer, and the compound is contained in a structure of the one or more layers of the hole injection layer, the hole transport layer, the electron blocking layer, the electron transport layer, and the electron injection layer.
8. A display device or a lighting device comprising an organic electronic device according to any one of claims 5 to 7.
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CN113150019A (en) * 2021-03-11 2021-07-23 上海和辉光电股份有限公司 Compound for organic electroluminescent device and application thereof

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CN102712842A (en) * 2009-11-13 2012-10-03 株式会社Lg化学 Novel compound having condensed ring, and organic electronic device using same
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