CN108929234B - Aromatic amine derivative and organic electroluminescent device thereof - Google Patents
Aromatic amine derivative and organic electroluminescent device thereof Download PDFInfo
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Abstract
The invention discloses an aromatic amine derivative and an organic electroluminescent device thereof, and relates to the technical field of organic photoelectric materials. The aromatic amine derivative is an electron-rich system and has a larger conjugated structure, so that the aromatic amine derivative has higher hole mobility and shows better hole transport performance. In addition, the aromatic amine derivative has a larger rigid structure due to the introduction of bulky groups, effectively improves the glass transition temperature and the thermal stability of the material, and is beneficial to film formation of the material. The organic electroluminescent device of the present invention comprises an anode, a cathode and one or more organic layers, the organic layers being located between the anode and the cathode, at least one of the organic layers containing the aromatic amine derivative of the present invention. The organic electroluminescent device has lower driving voltage, higher luminous efficiency and luminous brightness and longer service life.
Description
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to an aromatic amine derivative and an organic electroluminescent device thereof.
Background
Organic photovoltaic materials are organic materials that have the generation, conversion, and transport properties of photons and electrons. Currently, Organic photoelectric materials have been applied to Organic electroluminescent devices (OLEDs). An OLED refers to a device in which an organic photoelectric material emits light under the action of current or an electric field, and can directly convert electric energy into light energy. In recent years, OLEDs are receiving increasing attention as a new generation of flat panel display and solid state lighting technologies. Compared with the liquid crystal display technology, the OLED has the characteristics of low power consumption, active light emission, high response speed, high contrast, no visual angle limitation, capability of manufacturing flexible display and the like, and is increasingly applied to the fields of display and illumination.
Generally, an OLED has a multi-layer structure including an Indium Tin Oxide (ITO) anode and a metal cathode, and several organic layers, such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL), etc., interposed between the ITO anode and the metal cathode. Under the drive of a certain voltage, holes and electrons are respectively injected into the hole transport layer and the electron transport layer from the anode and the cathode, the holes and the electrons respectively migrate to the light emitting layer through the hole transport layer and the electron transport layer, when the holes and the electrons are combined in the light emitting layer in a meeting way, hole-electron composite excitons are formed, and the excitons return to the ground state in a light emitting relaxation way, so that the purpose of light emission is achieved.
The organic light emitting diode is used as a hole transport layer in an OLED, and basically has the functions of improving the transport efficiency of holes in the device, effectively blocking electrons in the light emitting layer and realizing the maximum recombination of current carriers; meanwhile, the energy barrier of the holes in the injection process is reduced, and the injection efficiency of the holes is improved, so that the brightness, the efficiency and the service life of the device are improved.
At present, organic electroluminescent devices generally have the problems of high operating voltage, low luminous efficiency, short service life and the like. Therefore, the search for new organic photoelectric materials for organic electroluminescent devices is a major direction of research by those skilled in the art. For the hole transport layer, the materials used conventionally do not generally provide satisfactory light emitting characteristics, and therefore, there is still a need to design new hole transport materials with better performance to improve the performance of the organic electroluminescent device.
Disclosure of Invention
The purpose of the invention is as follows: in view of the above problems, an object of the present invention is to provide an aromatic amine derivative and an organic electroluminescent device thereof, wherein the aromatic amine derivative is used as a hole transport material in the organic electroluminescent device, so as to reduce the driving voltage of the organic electroluminescent device, improve the luminous efficiency and brightness of the organic electroluminescent device, and prolong the service life of the organic electroluminescent device.
The technical purpose of the invention is realized by the following technical scheme: an aromatic amine derivative, which has a general structural formula shown in structural formula I:
wherein, Ar is1、Ar4Independently selected from one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
ar is2、Ar3Independently selected from one of the following groups,
x is selected from C (R)1)2、N(R1) O or S, the R1One selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C24 aryl, and substituted or unsubstituted C3-C24 heteroaryl, wherein A is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinolyl, substituted or unsubstituted phenanthryl or the following groups,
y is selected from N (R)2) O or S, the R2One selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C24 aryl, and substituted or unsubstituted C3-C24 heteroaryl;
said X1、X2、X3、X4、X5、X6Independently selected from C (R)3) Or N, said R3And B is selected from one of hydrogen, substituted or unsubstituted alkyl of C1-C10, substituted or unsubstituted aryl of C6-C24, and substituted or unsubstituted heteroaryl of C3-C24, wherein B is selected from one of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinolyl and substituted or unsubstituted phenanthryl.
Preferably, X is selected from N (R)1) O or S, the R1One selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl and substituted or unsubstituted C3-C18 heteroaryl.
Preferably, Y is selected from N (R)2) Said R is2One selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl and substituted or unsubstituted C3-C18 heteroaryl.
Preferably, Ar is1、Ar4Independently selected from one of substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C3-C30.
Preferably, Ar is1、Ar4Independently selected from one of the following groups,
wherein Z is selected from C (R)4)2、N(R4) O or S, the R4One selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C24 aryl, and substituted or unsubstituted C3-C24 heteroaryl;
the L is selected from one of single bond, substituted or unsubstituted arylene of C6-C24 and substituted or unsubstituted heteroarylene of C3-C24;
said Y is1、Y2、Y3、Y4、Y5、Y6、Y7、Y8Independently selected from C (R)5) Or N, said R5One selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C24 aryl, and substituted or unsubstituted C3-C24 heteroaryl.
Preferably, L is one selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted quinolylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.
Most preferably, the aromatic amine derivative of the present invention is selected from one of the following chemical structures,
further, the present invention also provides an organic electroluminescent device comprising an anode, a cathode and one or more organic layers, wherein the organic layers are located between the anode and the cathode, and at least one of the organic layers contains the aromatic amine derivative of the present invention.
Preferably, the organic layer includes a hole transport layer containing the aromatic amine derivative of the present invention.
Has the advantages that: the aromatic amine derivative is an electron-rich system and has a larger conjugated structure, so that the aromatic amine derivative has higher hole mobility and shows better hole transport performance. In addition, the aromatic amine derivative has a larger rigid structure due to the introduction of bulky groups, effectively improves the glass transition temperature and the thermal stability of the material, and is beneficial to film formation of the material.
The organic electroluminescent device using the aromatic amine derivative of the present invention as an organic layer has a low driving voltage, high luminous efficiency and luminance, and a long service life.
Detailed Description
The present invention is further illustrated by the following examples, which are intended to be purely exemplary and are not intended to limit the scope of the invention, as various equivalent modifications of the invention will occur to those skilled in the art upon reading the present disclosure and fall within the scope of the appended claims.
An aromatic amine derivative, which has a general structural formula shown in structural formula I:
wherein, Ar is1、Ar4Independently selected from one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
ar is2、Ar3Independently selected from one of the following groups,
x is selected from C (R)1)2、N(R1) O or S, the R1One selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C24 aryl, and substituted or unsubstituted C3-C24 heteroaryl, wherein A is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinolyl, substituted or unsubstituted phenanthryl or the following groups,
y is selected from N (R)2) O or S, the R2One selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C24 aryl, and substituted or unsubstituted C3-C24 heteroaryl;
said X1、X2、X3、X4、X5、X6Independently selected from C (R)3) Or N, said R3One selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C24 aryl and substituted or unsubstituted C3-C24 heteroaryl, wherein B is selected from hydrogen and substituted or unsubstituted C3-C24 heteroarylAnd (3) one of a phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted quinolyl group, and a substituted or unsubstituted phenanthryl group.
Preferably, X is selected from N (R)1) O or S, the R1One selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl and substituted or unsubstituted C3-C18 heteroaryl.
Preferably, Y is selected from N (R)2) Said R is2One selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl and substituted or unsubstituted C3-C18 heteroaryl.
Preferably, Ar is1、Ar4Independently selected from one of substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C3-C30.
Preferably, Ar is1、Ar4Independently selected from one of the following groups,
wherein Z is selected from C (R)4)2、N(R4) O or S, the R4One selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C24 aryl, and substituted or unsubstituted C3-C24 heteroaryl;
the L is selected from one of single bond, substituted or unsubstituted arylene of C6-C24 and substituted or unsubstituted heteroarylene of C3-C24;
said Y is1、Y2、Y3、Y4、Y5、Y6、Y7、Y8Independently selected from C (R)5) Or N, said R5Selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C3 to C24.
Preferably, L is one selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted quinolylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.
According to the invention, the substituents on the alkyl groups are independently selected from hydrogen, deuterium, cyano, trifluoromethyl, C1-C10 alkyl, C1-C10 alkoxy, C6-C24 aryl or C3-C24 heteroaryl;
the substituents on the aryl and the heteroaryl are independently selected from hydrogen, deuterium, cyano, trifluoromethyl, alkyl of C1-C10, alkoxy of C1-C10, aryl of C6-C24 or heteroaryl of C3-C24.
The alkyl group in the present invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule, and may be a straight-chain alkyl group, a branched-chain alkyl group, or a cyclic alkyl group, and examples thereof include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, cyclopentyl, and cyclohexyl groups.
The aryl group in the present invention refers to a general term of monovalent group left after one hydrogen atom is removed from the aromatic nucleus carbon of the aromatic hydrocarbon molecule, and may be monocyclic aryl group or condensed ring aryl group, and examples may include phenyl group, biphenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, etc., but are not limited thereto.
The heteroaryl group in the present invention refers to a general term of a group obtained by replacing one or more aromatic nuclear carbons in an aryl group with a heteroatom including, but not limited to, oxygen, sulfur or nitrogen atom, and may be a monocyclic heteroaryl group or a fused ring heteroaryl group, and examples may include, but are not limited to, pyridyl, pyrrolyl, pyridyl, thienyl, furyl, indolyl, quinolyl, isoquinolyl, benzothienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, and the like.
The arylene group in the present invention refers to a general term of monovalent group remaining after two hydrogen atoms are removed from the aromatic nucleus carbon of the aromatic hydrocarbon molecule, and may be monocyclic arylene group or condensed ring arylene group, and examples may include phenylene group, biphenylene group, naphthylene group, anthracenylene group, phenanthrenylene group, pyrenylene group, or the like, but are not limited thereto.
The heteroarylene group in the present invention refers to a general term of a group in which one or more aromatic core carbons in an arylene group are replaced with a heteroatom including, but not limited to, oxygen, sulfur or nitrogen atom, and the heteroarylene group may be a monocyclic heteroarylene group or a fused-ring heteroarylene group, and examples may include, but are not limited to, a pyridylene group, a pyrenylene group, a pyridylene group, a thienylene group, a furanylene group, an indolyl group, a quinolylene group, an isoquinolylene group, a benzothienylene group, a benzofuranylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a carbazolyl group and the like.
The substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C24 aryl and substituted or unsubstituted C3-C24 heteroaryl refer to the total number of carbon atoms of the alkyl, the aryl and the heteroaryl before being substituted, which is 1-10, 6-24, 3-24 and the like.
By way of example, without particular limitation, the aromatic amine derivative of the present invention is selected from one of the chemical structures shown below,
the synthetic route of the aromatic amine derivative is as follows:
wherein, Ar is1、Ar4Independently selected from one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
ar is2、Ar3Independently selected from one of the following groups,
x is selected from C (R)1)2、N(R1) O or S, the R1One selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C24 aryl, and substituted or unsubstituted C3-C24 heteroaryl, wherein A is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinolyl, substituted or unsubstituted phenanthryl or the following groups,
y is selected from N (R)2) O or S, the R2Selected from substituted or unsubstitutedOne of substituted C1-C10 alkyl, substituted or unsubstituted C6-C24 aryl and substituted or unsubstituted C3-C24 heteroaryl;
said X1、X2、X3、X4、X5、X6Independently selected from C (R)3) Or N, said R3And B is selected from one of hydrogen, substituted or unsubstituted alkyl of C1-C10, substituted or unsubstituted aryl of C6-C24, and substituted or unsubstituted heteroaryl of C3-C24, wherein B is selected from one of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinolyl and substituted or unsubstituted phenanthryl.
The 4-bromo-4-iodobiphenyl and the compound generate a compound Sub II through carbon-nitrogen coupling reaction, and the compound Sub II and the compound Sub I generate a product shown in a structural formula I through carbon-nitrogen coupling reaction.
The synthetic route of the aromatic amine derivative of the present invention is not particularly limited, and conventional reactions well known to those skilled in the art may be employed.
The present invention also provides an organic electroluminescent device comprising an anode, a cathode and one or more organic layers, the organic layers being located between the anode and the cathode, at least one of the organic layers comprising the aromatic amine derivative of the present invention.
The organic layer of the organic electroluminescent device of the present invention may have a single-layer structure, or a multi-layer structure having two or more layers. The organic layer of the organic electroluminescent device of the present invention may comprise any one or any plurality of hole injection layer, hole transport layer, light emitting layer, electron transport layer, electron injection layer. The thickness of the organic layer containing the aromatic amine derivative of the present invention is not more than 6 μm, preferably not more than 0.3 μm, and more preferably 0.002 to 0.3. mu.m. The organic layer containing the aromatic amine derivative of the present invention may further comprise other materials known in the art capable of hole injection, hole transport, light emission, electron transport, and electron injection, if necessary.
The aromatic amine derivative can be particularly used as a hole transport material for preparing an organic electroluminescent device. The organic electroluminescent device used is preferably: ITO attached to the light-transmitting glass serves as an anode, a hole injection layer, a hole transport layer, a light-emitting layer (host material: guest material), an electron transport layer, an electron injection layer and a metal cathode.
The organic electroluminescent device of the present invention can be manufactured by a known method using a known material, however, the structure of the organic electroluminescent device is not limited thereto.
The organic electroluminescent device can be widely applied to the fields of flat panel display, solid illumination, organic photoreceptors or organic thin film transistors and the like.
The starting materials used in the following examples are not particularly limited, and may be commercially available products or prepared by methods known to those skilled in the art.
Example 1: preparation of Compound TM5
Preparation of compound a 1:
under the protection of argon, 5-chloro-1H-indole-2-boric acid (10.2g,52.3mmol), iodobenzene (21.3 g,104.7mmol), CuI (5g,26.2mmol), ethylenediamine (1.8ml,26.2mmol), and Cs are sequentially added into a reaction bottle2CO3(51.2g,157.0mmol) and toluene (250ml) and the reaction mixture was stirred for one day. The organic phase was extracted with ethyl acetate, the organic phase was concentrated, and purified by column chromatography to give compound a1(7.1g, 50%).
Under the protection of argon, 8-bromo-1-naphthylamine (13.3g,60.0mmol), compound a1(17.9g,66 mmol), NaOH (7.2g,180mmol), Pd (PPh) were added to the reaction flask in sequence3)4(3.47g,3mmol) and THF/H2O (80ml/40ml), stirring the reaction mixture at 80 deg.C for 12 hr, cooling to room temperature, and extracting with tolueneTo obtain, combine the organic phases, wash the organic phase with saturated brine, dry and concentrate the organic phase, and purify by column chromatography to obtain compound b1(17.7g, 80%).
Slowly pouring compound b1(16.6g,45.0mmol) into 5% hydrochloric acid (150ml), stirring for 30 min, and sequentially adding NaNO at 0 deg.C2(3.7g,54.0mmol) in water (30ml), NaN3(3.5g,54.0mmol) was stirred for 1 hour in an aqueous solution (30ml), after completion of the reaction, extraction was performed with toluene, the organic phases were combined, washed with a saturated sodium bicarbonate solution, a saturated brine and distilled water in this order, and the organic phase was dried, concentrated and purified by column chromatography to obtain compound c1(12.4g, 70%).
Compound c1(16.6g,30.0mmol) and 1, 2-dichlorobenzene (100ml) were added sequentially to the reaction flask, stirred at 180 ℃ for 2 hours, after the reaction was finished, cooled to room temperature, extracted with toluene, combined organic phases, concentrated and purified by column chromatography to give compound d1(6.1g, 55%).
Under the protection of argon, compound d1(8.4g,23.0mmol), iodobenzene (14.1g,69.0mmol), Cu (0.15g,2.3mmol) and K were added to a reaction flask in sequence2CO3(6.3g,46.0mmol)、Na2SO4(6.5g,46.0mmol) and nitrobenzene (150ml) were stirred at 200 ℃ for 2 hours, after the reaction was complete, cooled to room temperature, extracted with toluene, the organic phases combined, washed with saturated brine, dried, concentrated and purified by column chromatography to give compound a1(7.6g, 75%).
Preparation of Compound Sub I-1:
aniline (14.0g,150mmol), Compound A1(44.3g,100mmol), sodium tert-butoxide (28.8g,300mmol), tris (dibenzylideneacetone) dipalladium (1.4g,1.5mmol), 1 '-binaphthyl-2, 2' -bis-diphenylphosphine (1.9 g,3mmol) and toluene (350ml) were added to a flask under an argon atmosphere and reacted at 130 ℃ for 24 hours. After cooling, the mixture was filtered and the filtrate was concentrated under reduced pressure. The obtained crude product was subjected to column purification, recrystallization from toluene, filtration and drying to obtain intermediate Sub1-1(42.5g, 85%).
Preparation of Compound Sub II-1:
diphenylamine (5.2g,31mmol), 4-bromo-4-iodobiphenyl (11.1g,31mmol), sodium tert-butoxide (3g,31mmol), bis (triphenylphosphine) palladium (II) dichloride (0.5g,0.71mmol) and xylene (500ml) were added to a flask under argon protection and reacted at 130 ℃ for 24 hours. After cooling, water (1000ml) was added, the mixture was filtered, the filtrate was extracted with toluene, and the organic phase was dried over anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the resulting crude product was subjected to column purification, recrystallization from toluene, filtration and drying to obtain intermediate Sub II-1(8.1g, 65%).
Preparation of Compound TM5
Under an argon atmosphere, the intermediate Sub1-1(5.0g,10mmol), intermediate Sub2-1(4.0g,10 mmol), sodium tert-butoxide (1.3g,13.5mmol), tris (dibenzylideneacetone) dipalladium (0.046g,0.05mmol), tri-tert-butylphosphine (0.021g,0.1mmol) and dehydrated toluene (50ml) were added to a flask and reacted at 80 ℃ for 2 hours. After cooling, water (500ml) was added, the mixture was filtered, the filtrate was extracted with toluene, and the organic phase was dried over anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the resulting crude product was subjected to column purification, recrystallization from toluene, filtration and drying to obtain the product TM5(5.7 g, 70%). Mass spectrum m/z: theoretical value: 819.02, respectively; measured value: 821.63. theoretical element content (%) C60H42N4: c, 87.99; h, 5.17; n, 6.84; measured elemental content (%): c, 87.96; h, 5.22; n,6.82. The above results confirmed that the obtained product was the objective product.
Example 2: preparation of Compound TM13
The iodobenzene in example 1 was replaced with equimolar 1-ethyl-4-iodobenzene and the other steps were the same as in the synthesis of example 1 to obtain compound TM13(6.6g, 75%). Mass spectrum m/z: theoretical value: 875.13, respectively; measured value: 877.31. theoretical element content (%) C64H50N4: c, 87.84; h, 5.76; n, 6.40; measured elemental content (%): c, 87.81; h, 5.83; and N, 6.36. The above results confirmed that the obtained product was the objective product.
Example 3: preparation of Compound TM61
The diphenylamine in example 1 was replaced with equimolar N-phenyl-4-benzidine, and the other steps were the same as those in example 1 to obtain TM61(6.4g, 72%). Mass spectrum m/z: theoretical value: 895.12, respectively; measured value: 896.73. theoretical element content (%) C66H46N4: c, 88.56; h, 5.18; n, 6.26; measured elemental content (%): c, 88.54; h, 5.23; and N, 6.23. The above results confirmed that the obtained product was the objective product.
Example 4: preparation of Compound TM83
The same procedures used in example 1 were repeated except for changing the 5-chloro-1H-indole-2-boronic acid in example 1 to an equimolar amount of 6-chloro-1H-indole-2-boronic acid and the iodobenzene to an equimolar amount of 4-iodopyridine to obtain Compound TM83(5.3g, 65%). Mass spectrum m/z: theoretical value: 821.00, respectively; measured value: 823.51. theoretical element content (%) C58H40N6: c, 84.85; h, 4.91; n, 10.24; measured elemental content (%): c, 84.82; h, 4.97; n, 10.21. The above results confirmed that the obtained product was the objective product.
Example 5: preparation of Compound TM109
The iodobenzene in example 1 was replaced with an equimolar amount of iodomethane, the diphenylamine was replaced with an equimolar amount of N-phenyldibenzofuran-2-amine, and the other steps were the same as in the synthesis of example 1 to obtain TM109(5.4g, 69%). Mass spectrum m/z: theoretical value: 784.96, respectively; measured value: 786.03. theoretical element content (%) C56H40N4O: c, 85.69; h, 5.14; n, 7.14; o, 2.04; measured elemental content (%): c, 85.66; h, 5.21; n, 7.12; and O, 2.02. The above results confirmed that the obtained product was the objective product.
Example 6: preparation of Compound TM125
The 5-chloro-1H-indole-2-boronic acid in example 1 was changed to an equimolar 6-chloro-1H-indole-2-boronic acid, diphenylamine was changed to an equimolar N-phenyl-2-naphthylamine, and the other steps were the same as those in the synthesis of example 1 to obtain TM1125(6.2g, 72%). Mass spectrum m/z: theoretical value: 869.08, respectively; measured value: 870.42. theoretical element content (%) C64H44N4: c, 88.45; h, 5.10; n, 6.45; measured elemental content (%): c, 88.42; h, 5.17; and N, 6.41. The above results confirmed that the obtained product was the objective product.
Example 7: preparation of Compound TM150
The iodobenzene in example 1 was replaced with an equimolar iodomethane, aniline was replaced with an equimolar benzidine, and diphenylamine was replaced with an equimolar 9, 9-dimethyl-N-phenyl-9 hydro-fluoren-3-amine, and the other steps were the same as in the synthesis of example 1, to obtain compound TM150 (6.2g, 70%). Mass spectrum m/z:theoretical value: 887.14, respectively; measured value: 889.22. theoretical element content (%) C65H50N4: c, 88.00; h, 5.68; n, 6.32; measured elemental content (%): c, 87.97; h, 5.72; and N, 6.31. The above results confirmed that the obtained product was the objective product.
Example 8: preparation of compound TM165
The 5-chloro-1H-indole-2-boronic acid in example 1 was changed to equimolar (6-bromobenzofuran-2-yl) boronic acid and diphenylamine was changed to equimolar N-phenyl-2-naphthylamine, and the other steps were the same as in the synthesis of example 1 to obtain TM165(4.9g, 62%). Mass spectrum m/z: theoretical value: 793.97; measured value: 795.43. theoretical element content (%) C58H39N3O: c, 87.74; h, 4.95; n, 5.29; o, 2.02; measured elemental content (%): c, 87.71; h, 5.01; n, 5.27; and O, 2.01. The above results confirmed that the obtained product was the objective product.
Example 9: preparation of Compound TM222
The 5-chloro-1H-indole-2-boronic acid in example 1 was replaced with equimolar (5-bromo-1-benzothien-2-yl) boronic acid, and the other steps were the same as those in the synthesis of example 1 to obtain compound TM222(4.9g, 60%). Mass spectrum m/z: theoretical value: 759.97, respectively; measured value: 760.62. theoretical element content (%) C54H37N3S: c, 85.34; h, 4.91; n, 5.53; s, 4.22; measured elemental content (%): c, 85.31; h, 4.97; n, 5.51; s, 4.21. The above results confirmed that the obtained product was the objective product.
Example 10: preparation of Compound TM227
The same procedures used in example 1 were repeated except for changing the 5-chloro-1H-indole-2-boronic acid in example 1 to equimolar (5-bromo-1-benzothien-2-yl) boronic acid, iodobenzene to equimolar iodomethane and aniline to equimolar benzidine, to thereby obtain Compound TM227(4.9g, 63%). Mass spectrum m/z: theoretical value: 774.00, respectively; measured value: 775.41. theoretical element content (%) C55H39N3S: c, 85.35; h, 5.08; n, 5.43; s, 4.14; measured elemental content (%): c, 85.31; h, 5.15; n, 5.41; and S, 4.13. The above results confirmed that the obtained product was the objective product.
Other target products were synthesized by referring to the synthesis methods of examples 1-10 above.
Application example 1: production of light-emitting device 1
Selecting ITO glass as an anode, ultrasonically cleaning, drying in a vacuum cavity, and vacuumizing to 5 x 10-5Pa, 2T-NATA was vacuum-deposited on the anode substrate as a hole injection layer to a thickness of 10 nm. The compound TM5 of the present invention was vacuum-deposited on the hole injection layer as a hole transport layer, and the deposition thickness was 30 nm. ADN was vacuum-deposited on the hole transport layer as a light-emitting material layer main body, 2% DPAVBi was doped, and the deposition thickness was 45 nm. Vacuum evaporation of Alq on the luminescent material layer3The electron transport layer was deposited to a thickness of 40 nm. And evaporating LiF on the electron transport layer to form an electron injection layer, wherein the evaporation thickness is 0.2 nm. Al was vacuum-deposited on the electron injection layer as a cathode, and the deposition thickness was 150 nm.
Application example 2: preparation of light-emitting device 2
The compound TM1 in application example 1 was replaced by the compound TM 13.
Application example 3: preparation of light-emitting device 3
The compound TM1 in application example 1 was replaced by the compound TM 61.
Application example 4: preparation of light-emitting device 4
The compound TM1 in application example 1 was replaced by the compound TM 83.
Application example 5: preparation of light-emitting device 5
Compound TM1 in application example 1 was replaced with compound TM 109.
Application example 6: preparation of light-emitting device 6
Compound TM1 in application example 1 was replaced by compound TM 125.
Application example 7: preparation of light-emitting device 7
Compound TM1 in application example 1 was replaced by compound TM 150.
Application example 8: preparation of light-emitting device 8
Compound TM1 in application example 1 was replaced by compound TM 165.
Application example 9: preparation of light-emitting device 9
The compound TM1 in application example 1 was replaced by the compound TM 222.
Application example 10: preparation of light emitting device 10
Compound TM1 in application example 1 was replaced by compound TM 227.
Comparative example 1
Selecting ITO glass as an anode, ultrasonically cleaning, drying in a vacuum cavity, and vacuumizing to 5 x 10-5Pa, 2T-NATA was vacuum-deposited on the anode substrate as a hole injection layer to a thickness of 10 nm. NPB was vacuum-deposited on the hole injection layer as a hole transport layer, and the thickness of the deposition was 30 nm. AND was vacuum-deposited on the hole transport layer as a light-emitting material layer main body, 2% DPAVBi was doped, AND the deposition thickness was 45 nm. Vacuum evaporation of Alq on the luminescent material layer3The electron transport layer was deposited to a thickness of 40 nm. And evaporating LiF on the electron transport layer to form an electron injection layer, wherein the evaporation thickness is 0.2 nm. Al was vacuum-deposited on the electron injection layer as a cathode, and the deposition thickness was 150 nm.
The results of testing the light emitting characteristics of the organic electroluminescent devices prepared in application examples 1 to 10 of the present invention and comparative example 1 are shown in table 1.
TABLE 1
As can be seen from table 1, the aromatic amine derivatives of the present invention are applied to an organic electroluminescent device as a hole transport material, and the organic electroluminescent device exhibits a lower driving voltage, a higher luminous efficiency and a longer lifespan, and has better durability and reliability.
Claims (6)
1. An aromatic amine derivative, which is characterized in that the aromatic amine derivative has a general structural formula shown as a structural formula I:
wherein, Ar is1、Ar4Independently selected from one of the following groups,
wherein Z is selected from C (R)4)2O or S, the R4One selected from methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl and tert-butyl;
l is selected from single bonds;
said Y is1、Y2、Y3、Y4、Y5、Y6、Y7、Y8Independently selected from C (R)5) Said R is5One selected from hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, phenyl and biphenyl;
ar is2One selected from the group consisting of,
ar is3One selected from the group consisting of,
x is selected from N (R)1) O or S, the R1One selected from the group consisting of methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyridyl, wherein A is selected from the group consisting of,
y is selected from N (R)2) Said R is2One selected from the group consisting of methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyridyl; in the substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl and substituted or unsubstituted pyridyl, the substituents are independently selected from hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl and phenyl;
said X1、X2、X3、X4、X5、X6Independently selected from C (R)3) Said R is3One selected from hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, phenyl and biphenyl, andb is selected from one of hydrogen and phenyl.
2. The aromatic amine derivative according to claim 1, wherein X is selected from N (R)1) O or S, the R1And is selected from one of methyl, ethyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl and substituted or unsubstituted pyridyl.
3. The aromatic amine derivative of claim 1, wherein Y is selected from N (R)2) Said R is2And is selected from one of methyl, ethyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl and substituted or unsubstituted pyridyl.
4. An aromatic amine derivative, which is characterized in that the aromatic amine derivative is selected from one of the chemical structures shown in the specification,
5. an organic electroluminescent device comprising an anode, a cathode and one or more organic layers disposed between the anode and the cathode, wherein at least one of the organic layers contains the aromatic amine derivative according to any one of claims 1 to 4.
6. An organic electroluminescent device according to claim 5, wherein the organic layer comprises a hole transport layer comprising the aromatic amine derivative according to any one of claims 1 to 4.
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