CN113788807A - Fused ring aromatic amine compound for organic layer of OLED device and synthetic method and application thereof - Google Patents

Fused ring aromatic amine compound for organic layer of OLED device and synthetic method and application thereof Download PDF

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CN113788807A
CN113788807A CN202111150696.2A CN202111150696A CN113788807A CN 113788807 A CN113788807 A CN 113788807A CN 202111150696 A CN202111150696 A CN 202111150696A CN 113788807 A CN113788807 A CN 113788807A
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aromatic amine
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邱丽霞
孙玉倩
刘杨
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BOE Technology Group Co Ltd
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Abstract

The invention discloses a condensed ring aromatic amine compound used in an organic layer of an OLED device, wherein SP is connected between two benzene rings in the compound3The hybridized carbon atom can effectively cut off the conjugated structure of the molecule, increase the rigidity of the compound molecule, and simultaneously increase the steric hindrance of the compound molecule, so that the molecule has higher triplet stateThe energy level and the high glass transition temperature ensure the thermal stability and the oxidation stability of the compound, are beneficial to increasing the stability of the material and prolonging the service life of the material. Meanwhile, the five-membered heterocyclic ring between the two benzene rings increases the molecular conjugate plane, which is beneficial to improving the charge mobility, is easy for charge dispersion and migration and improves the device efficiency; and the higher triplet state energy level enables the compound to effectively block electrons from entering the luminescence auxiliary layer, so that more excitons are recombined and emit light in the luminescent layer, and the efficiency of the device is improved. Therefore, the OLED device prepared by using the condensed ring aromatic amine compound has higher efficiency, more stable performance and longer service life.

Description

Fused ring aromatic amine compound for organic layer of OLED device and synthetic method and application thereof
Technical Field
The invention relates to the technical field of materials. And more particularly, to a fused ring aromatic amine compound used in an organic layer of an OLED device, and a synthesis method and application thereof.
Background
OLED devices are known to emit light in an injection mode. Under voltage driving, the anode injects holes into the light-emitting layer, the cathode injects electrons into the light-emitting layer, the holes and the electrons meet and combine in the light-emitting layer to form excitons, and the excitons recombine and transfer energy to the light-emitting material, which emits light through a radiation relaxation process.
The basic structure of the OLED device is a simple sandwich-type device, and the organic electroluminescent device is formed by spin coating, dip coating or vacuum thermal evaporation of a luminescent material (a luminescent layer) on a conductive glass substrate, then plating a cathode material and connecting a power supply. In order to improve the stability and efficiency of the organic electroluminescent device, the injection of electrons and holes should be balanced. The introduction of the injection layer (EIL/HIL), the transport layer (ETL/HTL) and the formation of the multilayer structure device in the organic electroluminescent device is beneficial to the balance of electron and hole injection, thereby improving the recombination probability and the luminous quantum efficiency in the luminous layer.
At present, the preparation method of the OLED device generally adopts a vacuum evaporation mode, and organic molecules form a compact thin layer on a substrate through evaporation. At present, research on OLED materials has been widely conducted in academic and industrial fields, and a large number of OLED materials with excellent performance are developed in succession, and for common OLED materials, which are usually aromatic conjugated structures, particularly aromatic amine materials, during evaporation, due to severe molecular planarization and strong intermolecular force, a crystalline state or a molecular aggregation state is easily formed on a substrate. The molecular aggregation causes interface degradation, and is one of the main factors of low device efficiency and poor stability. How to design new OLED materials with better performance is always a problem to be solved by those skilled in the art.
Disclosure of Invention
The invention aims to provide a condensed ring aromatic amine compound used in an organic layer of an OLED device, which has good charge transmission capability, higher glass transition temperature, good thermal stability and oxidation stability, high triplet state energy level and is an excellent OLED material.
Another object of the present invention is to provide a method for synthesizing a fused ring aromatic amine compound used in an organic layer of an OLED device.
It is still another object of the present invention to provide an OLED device and a display device including the condensed ring aromatic amine-based compound.
In order to achieve the purpose, the invention adopts the following technical scheme:
a fused ring aromatic amine compound for use in an organic layer of an OLED device, the fused ring aromatic amine compound having the general formula shown in formula (1) and formula (2):
Figure BDA0003287110870000021
wherein R is1And R2Each independently is alkyl or aryl, or R1And R2Are linked to form a substituted or unsubstituted ring;
x is O or S;
L1、L2and L3Each independently is a single bond, aryl of C6-C24 or heteroaryl of C5-C30;
Ar1、Ar2and Ar3Each independently is hydrogen, substituted or unsubstituted aryl or heteroaryl, substituted or unsubstituted amine, and Ar1、Ar2And Ar3At least one of which is a substituted or unsubstituted amine group.
Preferably, the substituted or unsubstituted amine group has the general formula shown in formula (3):
Figure BDA0003287110870000022
wherein Ar is4、Ar5Each independently is a substituted or unsubstituted aryl or heteroaryl group.
Preferably, Ar is4、Ar5Each independently is one of the following groups:
Figure BDA0003287110870000023
wherein the content of the first and second substances,
Figure BDA0003287110870000024
represents a bond.
Preferably, the fused ring aromatic amine compound represented by the formula (1) is:
Figure BDA0003287110870000031
Figure BDA0003287110870000041
preferably, the fused ring aromatic amine compound represented by the formula (2) is:
Figure BDA0003287110870000042
Figure BDA0003287110870000051
Figure BDA0003287110870000061
Figure BDA0003287110870000071
in a second aspect, the present invention provides a method for synthesizing the fused ring aromatic amine compound.
When the fused ring aromatic amine compound is represented by the general formula (1), the method comprises the following steps:
s1, mixing dibenzofuran-1-boric acid or its derivative, 2-bromo-4-chloro-1-iodobenzene or its derivative and Pd (Ph)3P)4Suspending in a solvent, adding a potassium carbonate solution, carrying out reflux reaction to obtain an intermediate product a,
Figure BDA0003287110870000072
s2, dissolving the intermediate product a in a solvent at-78 ℃ in an inert atmosphere, adding n-BuLi,
Figure BDA0003287110870000073
Reacting at room temperature to obtain an intermediate product b,
Figure BDA0003287110870000074
s3, dissolving the intermediate product b and the amine compound in a solvent in an inert atmosphere, and sequentially adding a tri-tert-butylphosphine solution and Pd2(dba)3And sodium tert-butoxide, heating and refluxing for reaction to obtain the compound shown in the formula (1).
When the fused ring aromatic amine compound is represented by the general formula (2), the method comprises the following steps:
n1, dibenzofuran-4-boronic acid or a derivative thereof, 2-bromo-4-chloro-1-iodobenzene or a derivative thereof and Pd (Ph)3P)4Suspending in a solvent, adding a potassium carbonate solution, carrying out reflux reaction to obtain an intermediate product c,
Figure BDA0003287110870000081
n2, dissolving the intermediate product c in a solvent at-78 ℃ in an inert atmosphere, adding N-BuLi,
Figure BDA0003287110870000082
Reacting at room temperature to obtain an intermediate product d,
Figure BDA0003287110870000083
n3, dissolving the intermediate product d and an amine compound in a solvent in an inert atmosphere, and sequentially adding a tri-tert-butylphosphine solution and Pd2(dba)3And sodium tert-butoxide, heating and refluxing to react to obtain a compound shown in a formula (2);
wherein R is1、R2、X、L1、L2And L3The group represented is the same as in the above formula (1) or formula (2);
r1、r2and r3Each independently is hydrogen, substituted or unsubstituted aryl or heteroaryl, halogen, and r1、r2And r3At least one halogen.
In a third aspect, the invention provides an OLED device comprising one or more of the above fused ring aromatic amine compounds.
Preferably, the material of at least one organic compound layer in the OLED device comprises one or more of the above fused ring aromatic amine compounds;
preferably, the OLED device includes an anode, a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a hole blocking layer, an electron transport layer, and a cathode, which are sequentially stacked; at least one layer of materials in the hole transport layer and the auxiliary light-emitting layer in the OLED device comprise one or more of the condensed ring aromatic amine compounds.
Preferably, the hole transport layer material comprises one or more of NPB, TPD, BAFLP, 4DFLDPBi, CBP or PCzPA.
Preferably, the host material of the light-emitting layer includes a blue light material anthracene derivative; wherein the blue light material anthracene derivatives comprise AND or/AND MAND;
the guest material of the light-emitting layer includes a pyrene derivative or/and a distyryl derivative DPVBi.
Preferably, the electron transport layer material comprises one or more of imidazole derivatives, oxazine derivatives, quinoline derivatives, isoquinoline derivatives or phenanthroline derivatives;
wherein the imidazole derivative comprises one or more of a benzimidazole derivative, an imidazopyridine derivative, or a benzimidazolophenanthridine derivative;
the oxazine derivative comprises a pyrimidine derivative or/and a triazine derivative.
Preferably, the electron transport layer material comprises one or more of PBD, OXD-7, TAZ, p-EtTAZ, BPhen, BCP, or TPBI. A fourth aspect of the invention provides a display apparatus comprising an OLED device as described above.
The invention has the following beneficial effects:
the invention provides a condensed ring aromatic amine compound used in an organic layer of an OLED device, wherein SP is connected between two benzene rings in the compound3The hybridized carbon atoms can effectively cut off a molecular conjugated structure, increase the rigidity of the compound molecules, and simultaneously increase the steric hindrance of the compound molecules, so that the molecules have higher triplet state energy levels and high glass transition temperatures, the thermal stability and the oxidation stability of the compound are ensured, the stability of the material is favorably improved, and the service life of the material is prolonged. Meanwhile, the five-membered heterocyclic ring between the two benzene rings increases the molecular conjugate plane, which is beneficial to improving the charge mobility, is easy for charge dispersion and migration and improves the device efficiency; and the higher triplet state energy level enables the compound to effectively block electrons from entering the luminescence auxiliary layer, so that more excitons are recombined and emit light in the luminescent layer, and the efficiency of the device is improved. Therefore, the OLED device prepared by using the condensed ring aromatic amine compound has higher efficiency, more stable performance and longer service life.
Drawings
The following describes embodiments of the present invention in further detail with reference to the accompanying drawings.
FIG. 1 shows the structural formula of a fused ring aromatic amine compound in the present invention.
Detailed Description
In order to more clearly illustrate the invention, the invention is further described below with reference to preferred embodiments and the accompanying drawings. Similar parts in the figures are denoted by the same reference numerals. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
In one aspect of the present invention, there is provided a condensed ring aromatic amine compound for use in an organic layer of an OLED device, the condensed ring aromatic amine compound having a general formula as shown in formula (1) or formula (2):
Figure BDA0003287110870000091
wherein R is1And R2Each independently is alkyl or aryl, or R1And R2Are linked to form a substituted or unsubstituted ring;
x is O or S;
L1、L2and L3Each independently is a single bond, aryl of C6-C24 or heteroaryl of C6-C24;
Ar1、Ar2and Ar3Each independently is hydrogen, substituted or unsubstituted aryl or heteroaryl, substituted or unsubstituted amine, and Ar1、Ar2And Ar3At least one of which is a substituted or unsubstituted amine group.
SP is connected between two benzene rings in the compound3The hybridized carbon atoms can effectively cut off the conjugated structure in the molecule and increase the rigidity of the molecule; and the carbon atom is modified with R1And R2The group can increase the steric hindrance of the compound, so that the molecule has higher triplet state energy level and high glass transition temperature, the thermal stability and oxidation stability of the compound are ensured, and the service life of the material is further prolonged. Meanwhile, the five-membered heterocyclic ring between the two benzene rings increases the molecular conjugate plane, is favorable for improving the charge mobility, is easy to disperse and migrate charges and improves the efficiency of the device.
The compound has higher triplet state energy level, can effectively prevent electrons from entering a luminescence auxiliary layer, and enables more excitons to emit light in a light-emitting layer in a composite mode. Therefore, the OLED (organic electroluminescent device) prepared by using the condensed ring aromatic amine compound has good luminous efficiency, stable luminous performance and long service life.
In some preferred embodiments, the substituted or unsubstituted amine group has the general formula shown in formula (3):
Figure BDA0003287110870000101
wherein Ar is4、Ar5Each independently is a substituted or unsubstituted aryl or heteroaryl, that is, the fused ring aromatic amine compound of the present invention contains a tertiary amine group, and the hydrogen atoms bonded to the nitrogen atoms are all substituted by aryl or heteroaryl.
Further preferably, Ar is4、Ar5Each independently is one of the following groups:
Figure BDA0003287110870000102
wherein the content of the first and second substances,
Figure BDA0003287110870000103
represents a bond.
In some preferred examples, the fused ring aromatic amine compound represented by formula (1) is:
Figure BDA0003287110870000104
Figure BDA0003287110870000111
Figure BDA0003287110870000121
in some preferred examples, the fused ring aromatic amine compound represented by formula (2) is:
Figure BDA0003287110870000122
Figure BDA0003287110870000131
Figure BDA0003287110870000141
Figure BDA0003287110870000151
the above compounds comprise at least one SP located between two benzene rings3A hetero carbon atom, a five-membered heterocycle containing O or S between two benzene rings, and a nitrogen atom to which three aryl or heteroaryl groups are attached. Therefore, the compound has strong molecular rigidity, large steric hindrance, and good carrier mobility and performance stability.
It should be noted that the specific kinds of the fused ring aromatic amine compounds in the present application are not limited to the above listed ones, and the compounds of formula (1) or formula (2) described above are within the scope of the present application.
In another aspect of the present invention, there is provided a process for producing the fused ring aromatic amine compound as described above.
When the fused ring aromatic amine compound is represented by the general formula (1), the method comprises the following steps:
s1, mixing dibenzofuran-1-boric acid or its derivative, 2-bromo-4-chloro-1-iodobenzene or its derivative and Pd (Ph)3P)4Suspending in a solvent, adding a potassium carbonate solution, carrying out reflux reaction to obtain an intermediate product a,
Figure BDA0003287110870000152
s2, dissolving the intermediate product a in a solvent at-78 ℃ in an inert atmosphere, adding n-BuLi,
Figure BDA0003287110870000153
Reacting at room temperature to obtain an intermediate product b,
Figure BDA0003287110870000161
s3, dissolving the intermediate product b and the amine compound in a solvent in an inert atmosphere, and sequentially adding a tri-tert-butylphosphine solution and Pd2(dba)3And sodium tert-butoxide, heating and refluxing to react to obtain the compound shown in the formula (1);
wherein R is1、R2、X、L1、L2And L3The group represented is the same as in the above formula (1) or formula (2);
r1、r2and r3Each independently is hydrogen, substituted or unsubstituted aryl or heteroaryl, halogen, and r1、r2And r3At least one halogen.
When the fused ring aromatic amine compound is represented by the general formula (2), it is understood by those skilled in the art that the reactant dibenzofuran-1-boronic acid or its derivative in S1 is only required to be replaced by dibenzofuran-4-boronic acid or its derivative, and other reaction conditions are not changed. Of course, the intermediate product may be prepared in a different structural formula from the intermediate product a and the intermediate product b.
Specifically, when the fused ring aromatic amine compound is represented by the general formula (2), the synthesis method comprises the following steps:
n1, dibenzofuran-4-boronic acid or a derivative thereof, 2-bromo-4-chloro-1-iodobenzene or a derivative thereof and Pd (Ph)3P)4Suspending in a solvent, adding a potassium carbonate solution, carrying out reflux reaction to obtain an intermediate product c,
Figure BDA0003287110870000162
n2, dissolving the intermediate product c in a solvent at-78 ℃ in an inert atmosphere, adding N-BuLi,
Figure BDA0003287110870000163
Reacting at room temperature to obtain an intermediate product d,
Figure BDA0003287110870000164
n3, dissolving the intermediate product d and an amine compound in a solvent in an inert atmosphere, and sequentially adding a tri-tert-butylphosphine solution and Pd2(dba)3And sodium tert-butoxide, heating and refluxing to react to obtain a compound shown in a formula (2);
wherein R is1、R2、X、L1、L2And L3The group represented is the same as in the above formula (1) or formula (2);
r1、r2and r3Each independently is hydrogen, substituted or unsubstituted aryl or heteroaryl, halogen, and r1、r2And r3At least one halogen.
The specific kind of the intermediate product is not specifically required, and those skilled in the art can flexibly select dibenzofuran-1-boronic acid derivatives, dibenzofuran-4-boronic acid derivatives and 2-bromo-4-chloro-1-iodobenzene derivatives modified with suitable groups as raw materials according to the specific structures of the compounds to be synthesized as shown in formula (1) and formula (2), and match the raw materials
Figure BDA0003287110870000171
And amine compounds, which are not a limiting requirement of the present application.
In a specific example, dibenzofuran-1-boric acid and 2-bromo-4-chloro-1-iodobenzene are used as raw materials, and the preparation process comprises the following steps:
s1-1, dibenzofuran-1-boronic acid, 2-bromo-4-chloro-1-iodobenzene and Pd (Ph)3P)4Suspending in dioxane, slowly dropwise adding a potassium carbonate solution into the suspension, carrying out reflux reaction, cooling to room temperature after the reaction is finished, separating to obtain an organic phase, washing, removing the solvent by rotary evaporation, and passing through a silica gel column to obtain an intermediate product:
Figure BDA0003287110870000172
s2-1, dissolving the intermediate product synthesized by S1-1 in anhydrous THF in inert atmosphere, stirring at-78 deg.C for half an hour, dripping n-BuLi ethane solution, stirring, and dripping
Figure BDA0003287110870000173
A THF solution of (1); and (3) raising the temperature to room temperature for reaction, after the reaction is finished, extracting in ice water, washing with water, drying, removing the solvent by rotary evaporation, directly refluxing the crude product with 120ml of HCl and 1200ml of AcOH at 100 ℃ overnight, filtering, washing with water and alcohol, and recrystallizing to obtain an intermediate product:
Figure BDA0003287110870000174
s3-1, mixing the intermediate product prepared from S2-1 with amine compound
Figure BDA0003287110870000175
Dissolving in toluene solution, quickly dropping tri-tert-butyl phosphine solution and Pd in nitrogen environment2(dba)3Adding sodium tert-butoxide, heating and refluxing for reaction, extracting an organic phase after the reaction is finished, washing, drying, removing the solvent by rotary evaporation to obtain a crude product, purifying, and recrystallizing to obtain the following compound:
Figure BDA0003287110870000176
as can be understood by those skilled in the art, the compound shown in the following can be prepared by replacing the reactant dibenzofuran-1-boronic acid in S1-1 with dibenzofuran-4-boronic acid under the same reaction conditions,
Figure BDA0003287110870000181
the above synthetic process for preparing the compound is only exemplary, and those skilled in the art can flexibly select the dibenzofuran-1-boronic acid derivative, the dibenzofuran-4-boronic acid derivative and the 2-bromo-4-chloro-1-iodobenzene derivative modified with suitable groups as raw materials according to the specific structures of the compounds to be finally synthesized as shown in formula (1) and formula (2), and set the specific reaction conditions in the synthetic process, which is not limited in this application.
The third aspect of the invention also provides an OLED device comprising one or more of the fused ring aromatic amine compounds described above. The structure and the preparation method of the OLED device are not limited in the invention. The OLED device prepared from the condensed ring aromatic amine compound has high carrier transmission capability, long service life, stable performance and high efficiency.
In some preferred examples, the OLED device structure includes an anode, a cathode, and an organic layer between the two electrodes, and the material of at least one organic compound layer in the OLED device includes one or more of the above-mentioned fused ring aromatic amine compounds.
Further preferably, the organic layer in the OLED device is a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), a light emission auxiliary layer (Prime), an emission layer (EML), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), and a capping layer on the cathode in this order from the anode layer to the cathode side.
In some preferred examples, at least one of the materials of the Hole Transport Layer (HTL) and the auxiliary light emitting layer (Prime) in the OLED device includes one or more of the above-described condensed ring aromatic amine-based compounds.
When the condensed ring aromatic amine compound is used as an auxiliary luminescent layer material, the compound has a higher triplet state energy level (T1 is more than 2.4eV), so that the compound can effectively prevent electrons from entering a luminescent auxiliary layer, more excitons are subjected to composite luminescence in a luminescent layer, and the efficiency of a device is improved; meanwhile, the glass transition temperature is high (Tg is more than 120 ℃), the thermal stability and the oxidation stability of the compound are ensured, the stability of the material is favorably improved, and the service life of the material is prolonged.
When the condensed ring aromatic amine compound is used as a hole transport layer, the condensed ring aromatic amine compound has higher hole mobility due to the appropriate HOMO energy level, and the efficiency of a device is improved.
When the compound is used for preparing a double-layer HT device, the higher hole mobility of the compound enables more holes to enter an EML to form electron-hole pairs with electrons, so that the compound emits light compositely and the efficiency of the device is improved.
In some preferred examples, the materials of the organic layers in the OLED device are arranged as follows:
the Hole Injection Layer (HIL) may be an inorganic oxide such as molybdenum oxide, silver oxide, tungsten oxide, manganese oxide, etc., or may be a p-type dopant of a strong electron-withdrawing system and a dopant of a hole transport material such as F4TCNQ, HATCN, etc.;
the Hole Transport Layer (HTL) and the Electron Blocking Layer (EBL) or the luminescence auxiliary layer (Prime) may be aromatic amines or carbazole materials, such as NPB, TPD, BAFLP, 4DFLDPBi, CBP, PCzPA, etc.;
the light-emitting layer comprises a host material AND a guest material, wherein the host material can be a blue light material anthracene derivative such as AND, MAND AND the like, AND the guest material can be a pyrene derivative, a distyryl derivative DPVBi AND the like;
the Hole Blocking Layer (HBL) and the Electron Transport Layer (ETL) are generally aromatic heterocyclic compounds such as imidazole derivatives such as benzimidazole derivatives, imidazopyridine derivatives, benzimidazolophenanthidine derivatives and the like, oxazine derivatives such as pyrimidine derivatives, triazine derivatives and the like, and compounds containing a nitrogen-containing six-membered ring structure (including also compounds having a phosphine oxide-based substituent on the heterocyclic ring) such as quinoline derivatives, isoquinoline derivatives, phenanthroline derivatives and the like, and specifically include, but are not limited to, PBD, OXD-7, TAZ, p-etaz, BPhen, BCP, TPBI and the like;
the Electron Injection Layer (EIL) includes, but is not limited to, alkali metals or metals such as LiF, Yb, Mg, Ca, etc.
In yet another aspect of the present invention, there is provided a display apparatus including the OLED device described above. Therefore, the display device has better quality of the display picture. It will be understood by those skilled in the art that the display device has all the features and advantages of the OLED device described above, and will not be described in any greater detail herein.
According to the embodiment of the invention, the specific type of the display device has no special requirement, and a person skilled in the art can flexibly select the display device according to the actual requirement. In some embodiments, the display device may be a panel, a cell phone, a notebook, an iPad, a kindle, a game console, or the like.
As can be understood by those skilled in the art, the display device includes, in addition to the OLED device described above, necessary structures or components of a conventional display device, such as a TFT backplane, a color filter substrate, a frame sealing adhesive, and the like.
The present invention will be described with reference to specific examples.
Synthesis example
Synthesis example 1
Synthesis of intermediate a-1
Suspending 100g (462mmol) of dibenzofuran-1-boronic acid, 138g (438mmol) of 2-bromo-4-chloro-1-iodobenzene and 10.7g (9.2mmol) of Pd (Ph3P)4 in 980ml of dioxane, slowly adding 1000ml of 2M potassium carbonate solution dropwise to this suspension, refluxing for 16h, cooling to room temperature, separating the organic phase, washing with water for 3 times, rotary evaporating the organic solvent, passing the crude product through a silica gel column to give intermediate a-1 in 66.9g 43% yield;
synthesis of intermediate b-1
Putting 35.5g (100mmol) of intermediate product a-1 into a dry reaction bottle, injecting 300ml of anhydrous THF into the reaction bottle by using an injector, pumping nitrogen for 3 times, stirring at-78 ℃ for half an hour, dropwise adding 50ml of n-BuLi (2M ethane solution) into the reaction bottle, stirring for 1h, and dropwise adding 21.8g (120mmol) of benzophenone dissolved in 200ml of THF; the reaction was allowed to warm to room temperature overnight, at the end of the reaction was poured into ice water and extracted with DCM, washed 3 times with water, dried over anhydrous sodium sulphate and filtered, the organic solvent was spun off by rotary evaporation and the crude product was refluxed overnight at 100 ℃ directly with 120ml HCl and 1200ml AcOH. After cooling, the solid is filtered, washed with water for 1 time, washed with ethanol for 3 times, and recrystallized with heptane to obtain an intermediate product b-1, 33.2g of 75%;
Figure BDA0003287110870000201
synthesis of Compound 1-1
7.1g (22mmol) of biphenylidine and 8.9g (20mmol) of intermediate b-1 were dissolved in 200ml of a toluene solution, nitrogen gas was purged 3 times, and 6.8ml (2.88mmol) of a 10% tri-tert-butylphosphine solution and 1.32g (1.44mmol) of Pd were rapidly dropped into the reaction flask2(dba)3Then, quickly adding 5.8g (60mmol) of sodium tert-butoxide, heating and refluxing for reaction for 6h, after the reaction is finished, pouring the reactant into water, extracting an organic phase, washing for 3 times, drying with anhydrous sodium sulfate, filtering, carrying out rotary evaporation to spin-dry an organic solvent to obtain a crude product, quickly passing through a silica gel column, recrystallizing with heptane/toluene, and finally carrying out vacuum sublimation to obtain a compound 1-1 with the purity of HPLC 99.9%, wherein the mass is 10.1g, and the yield is 70%; molecular formula C55H37NO; relative molecular mass 727.28; the structural characterization data for compound 1-1 are as follows:
EA:C,90.75；H,5.12；N,1.92；
1HNMR:8.20ppm(1H)；7.98ppm(1H)；7.75ppm(4H)；7.69ppm(1H)；7.55-7.54ppm(5H)；7.52ppm(1H)；7.49ppm(4H)；7.35-7.41(8H)；7.25-7.31ppm(6H)；7.18ppm(2H)；7.10ppm(4H)。
Figure BDA0003287110870000202
synthesis example 2
Synthesis of Compound 1-2 in Synthesis example 2 the procedure for synthesizing Compound 1-1 was substantially the same as that of Compound 1-1 except that 7.9g (22mmol) of Biphenyl-4-yl- (9, 9-dimethyl-9H-fluoren-2-yl) amine was used in place of Biphenyl amine to obtain Compound 1-2 mass 10.4g, yield 68%, molecular formula C58H41NO, relative molecular mass 767.32; the structural characterization data for compounds 1-2 are as follows: EA: C, 90.71; h, 5.38; n, 1.82;
1HNMR:8.20ppm(1H)；7.98ppm(1H)；7.9-7.86ppm(2H)；7.75ppm(2H)；7.69ppm(1H)；7.55-7.54ppm(4H)；7.52ppm(1H)；7.49ppm(2H)；7.30-7.41(8H)；7.25-7.30ppm(6H)；7.18-7.16ppm(3H)；7.10-7.08ppm(4H)；1.65ppm(6H)。
Figure BDA0003287110870000211
synthesis example 3
Synthesis of intermediate c-1
100g (462mmol) of dibenzofuran-4-boronic acid, 138g (438mmol) of 2-bromo-4-chloro-1-iodobenzene and 10.7g (9.2mmol) of Pd (Ph)3P)4Suspending in 980ml dioxane, slowly dropwise adding 1000ml 2M potassium carbonate solution into the suspension, refluxing for 16h, cooling to room temperature, separating the organic phase, washing with water for 3 times, performing rotary evaporation to spin dry the organic solvent, and passing the crude product through a silica gel column to obtain an intermediate product c-1 with the mass of 70g and the yield of 45%;
synthesis of intermediate d-1
Putting 35.5g (100mmol) of c-1 into a dry reaction bottle, injecting 300ml of anhydrous THF into the reaction bottle by using an injector, pumping nitrogen for 3 times, stirring at-78 ℃ for half an hour, dropwise adding 50ml of n-BuLi (2M ethane solution) into the reaction bottle, stirring for 1h, and dropwise adding 21.8g (120mmol) of benzophenone dissolved in 200ml of THF; the reaction was allowed to warm to room temperature overnight, at the end of the reaction was poured into ice water and extracted with DCM, washed 3 times with water, dried over anhydrous sodium sulphate and filtered, the organic solvent was spun off by rotary evaporation and the crude product was refluxed overnight at 100 ℃ directly with 120ml HCl and 1200ml AcOH. After cooling, the solid was filtered, washed with water 1 time, ethanol 3 times, and recrystallized with heptane to give intermediate d-1, 31g in mass, 70% yield;
Figure BDA0003287110870000212
synthesis of Compound 2-1
7.1g (22mmol) of biphenylidine and 8.9g (20mmol) of intermediate d-1 were dissolved in 200ml of a toluene solution, nitrogen gas was purged 3 times, and 6.8ml (2.88mmol) of a 10% tri-tert-butylphosphine solution and 1.32g (1.44mmol) of Pd were rapidly dropped into a reaction flask2(dba)3Then, quickly adding 5.8g (60mmol) of sodium tert-butoxide, heating and refluxing for reaction for 6h, after the reaction is finished, pouring the reactant into water, extracting an organic phase, washing for 3 times, drying with anhydrous sodium sulfate, filtering, carrying out rotary evaporation to spin-dry an organic solvent to obtain a crude product, quickly passing through a silica gel column, recrystallizing with heptane/toluene, and finally carrying out vacuum sublimation to obtain a compound 2-1 with the purity of HPLC 99.9%, wherein the mass is 9.45g, and the yield is 65%; molecular formula C55H37NO, relative molecular weight 727.28. The structural characterization data for compound 2-1 is as follows:
EA:C,90.75；H,5.12；N,1.92；
1HNMR:8.20ppm(1H)；7.98-7.90ppm(2H)；7.75ppm(4H)；7.55-7.54ppm(5H)；7.50ppm(1H)；7.49-7.45ppm(4H)；7.35-7.40(8H)；7.25-7.35ppm(5H)；7.15-7.25ppm(3H)；7.10-7.05ppm(4H)。
Figure BDA0003287110870000221
synthesis example 4
Synthesis of Compound 2-2
Synthesis example 4A Synthesis procedure of the compound 2-2 was substantially the same as that of the compound 2-1 except that 7.9g (22mmol) of biphenyl-4-yl- (9, 9-dimethyl-9H-fluoren-2-yl) amine was used in place of biphenylamine to obtain a compound 2-2 of 10.3g in mass, 67% yield and the formula C58H41NO, relative molecular mass 767.32; the structural characterization data for compound 2-2 is as follows: EA: c, 90.71; h, 5.38; n, 1.82;
1HNMR:8.20ppm(1H)；7.98-7.95ppm(2H)；7.9-7.85ppm(2H)；7.75-7.70ppm(2H)；7.55-7.54ppm(4H)；7.52ppm(1H)；7.49ppm(2H)；7.30-7.43(8H)；7.25-7.30ppm(5H)；7.25-7.15ppm(4H)；7.10-7.08ppm(4H)；1.65ppm(6H)；
Figure BDA0003287110870000222
some examples of Synthesis
Other amine compounds, such as those shown in Table 1, can be obtained by reacting the intermediate product b-1 with other amine compounds instead of the biphenylamine in Synthesis example 1.
TABLE 1 some of the compounds having the structure represented by the general formula (1)
Figure BDA0003287110870000223
Figure BDA0003287110870000231
Some examples of Synthesis
Some other amine compounds, such as those shown in Table 2, can be obtained by substituting the biphenyl amines of Synthesis example 3 with the intermediate d-1.
TABLE 2 some of the compounds having the structure represented by the general formula (2)
Figure BDA0003287110870000232
Synthesis example 5
Synthesis of intermediate a-2 and intermediates b-2 and b-3
The synthesis of intermediate a-2 is similar to that of intermediate a-1 except that the reactants are replaced, as shown in the following equation.
The synthesis of intermediates b-2 and b-3 is similar to the synthesis of intermediate b-1 except that the reactants are replaced, as shown in the following reaction equation.
Figure BDA0003287110870000241
Synthesis of Compounds 1-7
Synthesis procedures for Compounds 1-7 in Synthesis example 5 were substantially the same as for Compound 1-1, except that intermediate b-1 was replaced with intermediate b-2. The mass of the synthesized compounds 1 to 7 was 9.45g, and the yield was 65%; molecular formula C55H37NO, relative molecular weight 727.28; the structural characterization data of the compounds 1-7 are EA: C, 90.75; h, 5.12; n, 1.92. The specific reaction process is as follows:
Figure BDA0003287110870000242
synthesis example 6
Synthesis of Compounds 1-8
Synthesis of Compounds 1-8 in Synthesis example 6 the procedure for synthesizing compounds 1-8 was essentially the same as for Compounds 1-7 except that diphenylamine was replaced with biphenyl-4-yl- (9, 9-dimethyl-9H-fluoren-2-yl) amine and Compounds 1-8 were synthesized with the molecular formula C58H41NO, relative molecular mass 767.32; structural characterization data for compounds 1-8 is EA: c, 90.71; h, 5.38; n, 1.82. The specific reaction process is as follows:
Figure BDA0003287110870000251
some examples of Synthesis
Some other amine compounds, such as those shown in Table 3, can be obtained by reacting the intermediate b-2 or b-3 with some other amine compounds in place of the biphenylamine in Synthesis example 5.
TABLE 3 some of the compounds having the structure represented by the general formula (1)
Figure BDA0003287110870000252
Figure BDA0003287110870000261
Some examples of Synthesis
Synthesis of intermediate c-2 and intermediates d-2 and d-3
The synthesis of intermediate c-2 is similar to that of intermediate c-1 except that the reactants are replaced, as shown in the following equation.
The synthesis of intermediates d-2 and d-3 is similar to the synthesis of intermediate d-1 except that the reactants are replaced, as shown in the following reaction equation.
Figure BDA0003287110870000262
The reaction process of the intermediate product d-2 or d-3 and the amine compound is similar to the reaction process of the intermediate product d-1 and the amine compound in the synthetic example 3,
some other amine compounds, for example, those shown in Table 4, can be obtained by reacting the intermediate d-2 or d-3 with some other amine compounds instead of the biphenylamine in Synthesis example 3.
TABLE 4 some of the compounds having the structure represented by the general formula (2)
Figure BDA0003287110870000271
Figure BDA0003287110870000281
Examples
The preparation process of the OLED device comprises the following steps:
forming a pixel driving circuit and an anode (ITO) on a glass substrate;
evaporating a Hole Injection Layer (HIL) and a Hole Transport Layer (HTL) by using an Open mask, wherein the thicknesses of the HIL and the HTL are respectively 5-20nm and 80-120 nm;
evaporating a light-emitting auxiliary layer (Prime) and a blue light-emitting layer (EML) by using a Fine Metal Mask (FMM), wherein the Prime thickness is 5-20nm, the EML comprises a blue light main Body (BH) and a blue light object (BD), the thickness is 10-30nm, and the doping proportion of the blue light object is 2-10%;
evaporating a Hole Blocking Layer (HBL) and an Electron Transport Layer (ETL) by using an Open mask, wherein the thicknesses of the HBL and the ETL are respectively 5-20nm and 20-50 nm;
finally, an Open mask is used to evaporate the metal cathode (Mg: Ag alloy).
The materials and thicknesses of the layers in the OLED device structures of examples 1-7 and comparative example 1 are shown in Table 5.
TABLE 5 materials and thicknesses of layers in OLED device structures of examples 1-7 and comparative example 1
Figure BDA0003287110870000282
Figure BDA0003287110870000291
Specific compounds are shown below:
Figure BDA0003287110870000292
some performance parameters were determined for compound NPB, compound 1-1, compound 1-2, compound TCTA, compound 1-5, compound 1-6, compound 1-7, compound 1-8: HOMO/LUMO energy levels were tested using AC3& CV & UV spectroscopy; the triplet level T1 was determined by means of a low-temperature phosphorescence spectrometer (T1 ═ 1240/PL peak) and the glass transition temperature Tg was measured by means of DSC. The structure is shown in the following table:
property parameters of the Compounds of Table 6
Figure BDA0003287110870000301
As can be seen from the results in Table 3, the fused ring fluorenamine compound synthesized in the invention has wide molecular optical band gap and strong molecular stability; meanwhile, the glass transition temperature Tg and the triplet state energy level T1 are also higher. In general, the fused ring aromatic amine compound synthesized by the method has more excellent overall performance and is more suitable for preparing OLED devices.
The performance of the OLED devices of examples 1-7 and comparative example 1 was determined, with the performance of the OLED device of comparative example 1 being 100% and the device performance of examples 1-7 being shown in Table 7:
TABLE 7 OLED device Performance in examples 1-7 and comparative example 1
OLED device Driving voltage Device efficiency Device lifetime
Comparative example 1 100％ 100％ 100％
Example 1 102％ 120％ 121％
Example 2 98％ 132％ 110％
Example 3 103％ 119％ 118％
Example 4 99％ 127％ 113％
Example 5 97％ 136％ 120％
Example 6 95％ 140％ 118％
Example 7 98％ 118％ 108％
As can be seen from table 4, in examples 1 to 4 and 7, when the fused ring aromatic amine compound of the present invention is used as an HTL material, the fluorene group in the compound is fused and conjugated with the aromatic ring group, so that the material has a large hole mobility, and more holes enter the EML layer to form a hole-electron pair with electrons, thereby performing recombination light emission and improving the efficiency of the OLED device. At the same time, the Tg is higher, so that the efficiency and the lifetime of the OLED devices in examples 1-4 are significantly improved.
In examples 5 and 6, when the compounds 1 to 5 and 1 to 6 are used as BHT materials, the molecules have dibenzofuran and carbazole groups, so that the triplet level is higher, the hole mobility is improved, electrons can be effectively blocked in the EML layer, more excitons are allowed to emit light compositely in the EML layer, and the device efficiency is improved; meanwhile, the compound has high Tg, strong stability and longer service life.
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.

Claims (14)

1. A fused ring aromatic amine compound used in an organic layer of an OLED device is characterized in that the fused ring aromatic amine compound has a general formula shown in formula (1) or formula (2):
Figure FDA0003287110860000011
wherein R is1And R2Each independently is alkyl or aryl, or R1And R2Are linked to form a substituted or unsubstituted ring;
x is O or S;
L1、L2and L3Each independently is a single bond, aryl of C6-C24 or heteroaryl of C5-C30;
Ar1、Ar2and Ar3Each independently is hydrogen, substituted or unsubstituted aryl or heteroaryl, substituted or unsubstituted amine, and Ar1、Ar2And Ar3At least one of which is a substituted or unsubstituted amine group.
2. A fused ring aromatic amine compound according to claim 1, wherein said substituted or unsubstituted amine group has a general formula shown in formula (3):
Figure FDA0003287110860000012
wherein Ar is4、Ar5Each independently is a substituted or unsubstituted aryl or heteroaryl group.
3. A fused ring aromatic amine compound according to claim 2, wherein Ar is4、Ar5Each independently is one of the following groups:
Figure FDA0003287110860000013
wherein the content of the first and second substances,
Figure FDA0003287110860000021
represents a bond.
4. A fused ring aromatic amine compound according to claim 1, wherein the fused ring aromatic amine compound represented by formula (1) is:
Figure FDA0003287110860000022
Figure FDA0003287110860000031
5. a fused ring aromatic amine compound according to claim 1, wherein the fused ring aromatic amine compound represented by formula (2) is:
Figure FDA0003287110860000041
Figure FDA0003287110860000051
Figure FDA0003287110860000061
6. a method for synthesizing a fused ring aromatic amine compound according to any one of claims 1 to 4,
when the fused ring aromatic amine compound is represented by the general formula (1), the method comprises the following steps:
s1, mixing dibenzofuran-1-boric acid or its derivative, 2-bromo-4-chloro-1-iodobenzene or its derivative and Pd (Ph)3P)4Suspending in a solvent, adding a potassium carbonate solution, carrying out reflux reaction to obtain an intermediate product a,
Figure FDA0003287110860000062
s2, dissolving the intermediate product a in a solvent at-78 ℃ in an inert atmosphere, adding n-BuLi,
Figure FDA0003287110860000063
Reacting at room temperature to obtain an intermediate product b,
Figure FDA0003287110860000071
s3, dissolving the intermediate product b and the amine compound in a solvent in an inert atmosphere, and sequentially adding a tri-tert-butylphosphine solution and Pd2(dba)3And sodium tert-butoxide, heating and refluxing to react to obtain the compound shown in the formula (1);
when the fused ring aromatic amine compound is represented by the general formula (2), the method comprises the following steps:
n1, dibenzofuran-4-boronic acid or a derivative thereof, 2-bromo-4-chloro-1-iodobenzene or a derivative thereof and Pd (Ph)3P)4Suspending in a solvent, adding a potassium carbonate solution, carrying out reflux reaction to obtain an intermediate product c,
Figure FDA0003287110860000072
n2, dissolving the intermediate product c in a solvent at-78 ℃ in an inert atmosphere, adding N-BuLi,
Figure FDA0003287110860000073
Reacting at room temperature to obtain an intermediate product d,
Figure FDA0003287110860000074
n3, dissolving the intermediate product d and an amine compound in a solvent in an inert atmosphere, and sequentially adding a tri-tert-butylphosphine solution and Pd2(dba)3And sodium tert-butoxide, heating and refluxing to react to obtain a compound shown in a formula (2);
wherein R is1、R2、X、L1、L2And L3The group represented is the same as in claim 1;
r1、r2and r3Each independently is hydrogen, substituted or unsubstituted aryl or heteroaryl, halogen, and r1、r2And r3At least one halogen.
7. An OLED device comprising one or more of the fused ring aromatic amine compounds of any one of claims 1 to 5.
8. The OLED device of claim 8, wherein at least one of the organic compound layers in the OLED device is made of a material comprising one or more of the fused ring aromatic amine compounds of any one of claims 1-5.
9. The OLED device according to claim 7, comprising an anode, a hole injection layer, a hole transport layer, an auxiliary light-emitting layer, a hole blocking layer, an electron transport layer, and a cathode, which are sequentially stacked; wherein at least one layer of the materials of the hole transport layer and the auxiliary light-emitting layer comprises one or more of the fused ring aromatic amine compounds according to any one of claims 1 to 5.
10. The OLED device of claim 9, wherein the hole transport layer material includes one or more of NPB, TPD, BAFLP, 4DFLDPBi, CBP, or PCzPA.
11. The OLED device of claim 9, wherein the host material of the light-emitting layer includes a blue light material anthracene derivative; the guest material of the light-emitting layer comprises a pyrene derivative or/and a distyryl derivative DPVBi;
wherein the blue light material anthracene derivatives comprise AND or/AND MAND.
12. The OLED device of claim 9, wherein the electron transport layer material comprises one or more of an imidazole derivative, an oxazine derivative, a quinoline derivative, an isoquinoline derivative, or a phenanthroline derivative;
wherein the imidazole derivative comprises one or more of a benzimidazole derivative, an imidazopyridine derivative, or a benzimidazolophenanthridine derivative;
the oxazine derivative comprises a pyrimidine derivative or/and a triazine derivative.
13. The OLED device of claim 12, wherein the electron transport layer material includes one or more of PBD, OXD-7, TAZ, p-etaz, BPhen, BCP, or TPBI.
14. A display device comprising an OLED device as claimed in any one of claims 7 to 13.
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