CN109180528A - A kind of triarylamine derivative and its organic electroluminescence device - Google Patents

A kind of triarylamine derivative and its organic electroluminescence device Download PDF

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CN109180528A
CN109180528A CN201811156604.XA CN201811156604A CN109180528A CN 109180528 A CN109180528 A CN 109180528A CN 201811156604 A CN201811156604 A CN 201811156604A CN 109180528 A CN109180528 A CN 109180528A
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triarylamine derivative
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蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The invention discloses a kind of triarylamine derivative and its organic electroluminescence devices, belong to organic photoelectrical material technical field.Triarylamine derivative of the invention can effectively transmit electronics but also effective transporting holes, have good carrier transmission characteristics, make electrons and holes can be effective compound in luminescent layer, luminous efficiency is high.In addition the methylene fluorenes class group in triarylamine derivative of the invention increases the rigidity of structure, and it also introduces with large volume of substituent group, such as naphthalene, fluorenyl etc., the glass transition temperature and thermal stability of material are effectively raised, material filming is conducive to.Organic electroluminescence device of the invention includes anode, cathode and organic matter layer, and for organic matter layer between anode and cathode, organic matter layer contains triarylamine derivative of the invention.Organic electroluminescence device of the invention has lower driving voltage, higher luminous efficiency and longer service life.

Description

Triarylamine derivative and organic electroluminescent device thereof
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a triarylamine derivative and an organic electroluminescent device thereof.
Background
An Organic Light-Emitting Diode (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 organic electroluminescent device has a multi-layered structure including an anode, a cathode, and 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), interposed between the anode and the 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.
In the case of the light emitting layer, when only one material is used as the light emitting layer, concentration quenching occurs due to an interaction between molecules, resulting in a decrease in the light emitting efficiency of the organic electroluminescent device, and thus in order to increase the light emitting efficiency of the organic electroluminescent device, the light emitting layer is generally in a form in which a host material and a guest material are doped with each other.
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 light emitting layer, the conventionally used host materials generally fail to provide satisfactory light emitting characteristics, and therefore, there is still a need to design new host 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 a triarylamine derivative and an organic electroluminescent device thereof, wherein the triarylamine derivative is applied to the organic electroluminescent device as a host material, so that the organic electroluminescent device exhibits better use performance, and the problem of poor light emitting characteristics of the host material in the conventional organic electroluminescent device is solved.
The technical purpose of the invention is realized by the following technical scheme: a triarylamine derivative has a structural general formula shown in a structural formula I,
wherein R is selected from one of cyano, halogen, substituted or unsubstituted aryl of C6-C18, and substituted or unsubstituted heteroaryl of C3-C18;
said L1、L2Independently selected from a single bond, substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted heteroarylene of C3-C30;
n is selected from 0 or 1;
ar is2、Ar3Independently selected from one of substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C3-C30;
ar is1、Ar4Independently selected from one of the groups shown below,
rx and Ry are independently selected from one of substituted or unsubstituted C1-C10 alkyl and substituted or unsubstituted C6-C18 aryl,
l is selected from substituted or unsubstituted arylene of C6-C18,
a is selected from one of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl and substituted or unsubstituted indenyl,
and B is selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl and substituted or unsubstituted indenyl.
Preferably, R is selected from one of the following groups,
the R is1、R2、R3、R4、R5、R6、R7、R8Independently selected from one of hydrogen, cyano, halogen, trifluoromethyl, trichloromethyl, trifluoromethoxy, methyl, ethyl, propyl, butyl, pentyl and hexyl.
Preferably, said L1、L2Independently selected from single bond or selected from one of the following groups,
said X0Selected from O or S;
said X1、X2、X3、X4、X5、X6、X7、X8、X9、X10Independently selected from N or C (R)0) Said R is0One selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C1-C18 heteroaryl.
Preferably, Ar is1、Ar4Independently selected from one of the groups shown below,
preferably, R is selected from one of the following groups,
preferably, said L1、L2Independently selected from a single bond or one of the groups shown below,
preferably, Ar is2、Ar3Independently selected from one of the groups shown below,
preferably, the triarylamine derivative shown in the structural formula I is selected from one of the structural formulas shown in the following formulas,
further, the present invention also provides an organic electroluminescent device comprising an anode, a cathode and an organic layer, wherein the organic layer is located between the anode and the cathode, and the organic layer comprises the triarylamine derivative of the present invention.
Preferably, the organic layer includes a light-emitting layer including a host material containing the triarylamine derivative of the present invention and a guest material.
Has the advantages that: compared with the prior art, the triarylamine derivative has the advantages that methylene fluorene substituent groups in the triarylamine derivative have good electron acceptor properties, and aromatic amine groups have good electron donor properties, so that the triarylamine derivative can effectively transmit electrons and holes, has good carrier transmission characteristics, enables the electrons and the holes to be effectively compounded in a light-emitting layer, and has high light-emitting efficiency. In addition, the methylene fluorene group in the triarylamine derivative increases the structural rigidity, and substituent groups with larger volume, such as naphthyl, fluorenyl and the like, are introduced into the triarylamine derivative, so that the glass transition temperature and the thermal stability of the material are effectively improved, and the material is favorable for film formation.
The organic light-emitting device using the triarylamine derivative as an organic layer has lower driving voltage, higher luminous efficiency and longer 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 fall within the scope of the claims of this application after reading the present invention.
A triarylamine derivative has a structural general formula shown in a structural formula I,
wherein R is selected from one of cyano, halogen, substituted or unsubstituted aryl of C6-C18, and substituted or unsubstituted heteroaryl of C3-C18;
said L1、L2Independently selected from a single bond, substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted heteroarylene of C3-C30;
n is selected from 0 or 1;
ar is2、Ar3Independently selected from one of substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C3-C30;
ar is1、Ar4Independently selected from one of the groups shown below,
rx and Ry are independently selected from one of substituted or unsubstituted C1-C10 alkyl and substituted or unsubstituted C6-C18 aryl,
l is selected from substituted or unsubstituted arylene of C6-C18,
a is selected from one of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl and substituted or unsubstituted indenyl,
and B is selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl and substituted or unsubstituted indenyl.
Preferably, R is selected from one of the following groups,
the R is1、R2、R3、R4、R5、R6、R7、R8Independently selected from one of hydrogen, cyano, halogen, trifluoromethyl, trichloromethyl, trifluoromethoxy, methyl, ethyl, propyl, butyl, pentyl and hexyl.
Preferably, said L1、L2Independently selected from a single bond or one of the groups shown below,
said X0Selected from O or S;
said X1、X2、X3、X4、X5、X6、X7、X8、X9、X10Independently selected from N or C (R)0) Said R is0One selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C1-C18 heteroaryl.
Preferably, Ar is1、Ar4Independently selected from one of the groups shown below,
preferably, R is selected from one of the following groups,
preferably, said L1、L2Independently selected from a single bond or one of the groups shown below,
preferably, Ar is2、Ar3Independently selected from one of the groups shown below,
according to the invention, the substituents on the above alkyl groups are selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, nitro; or C1-C10 alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, cyclopropyl, cyclobutyl, cyclopentyl, etc.; or alkoxy of C1 to C10 such as methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.; or an aryl group having C6 to C24 such as phenyl, naphthyl, phenanthryl, fluorenyl, etc.; or a heteroaryl group of C3-C24, such as pyridyl, pyrimidyl, triazinyl, quinolyl, furyl, thienyl, dibenzofuryl, dibenzothienyl, carbazolyl, and the like.
The substituents on the aryl and the heteroaryl are independently selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen and nitro; or C1-C10 alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, etc.; or alkoxy of C1 to C10 such as methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.; or an aryl group having C6 to C24, such as phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, anthracenyl, triphenylene, fluorenyl, etc.; or a heteroaryl group of C3-C24, for example, pyridyl, pyrimidyl, triazinyl, quinolyl, furyl, thienyl, dibenzofuryl, dibenzothienyl, carbazolyl, etc.; alternatively, the arylamine group having C6 to C24 may be, for example, a diphenylamino group, a biphenylamino group or the like.
The substituents on the arylene and the heteroarylene are independently selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, nitro, 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 aryl of C6-C18 and the substituted or unsubstituted heteroaryl of C3-C18 refer to the total number of carbon atoms of the aryl and the heteroaryl before being substituted, which is 6-18 and 3-18 respectively, and the like.
The linear alkyl group having more than two carbon atoms such as propyl, butyl, pentyl, etc. in the present invention includes isomers thereof, such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, etc., but is not limited thereto.
By way of example, without particular limitation, the triarylamine derivative represented by structural formula I is selected from one of the structural formulae shown below,
the synthetic route of the triarylamine derivative of the invention is as follows:
(I) when n is a number of 0, the compound is,
obtained by carbon-carbon coupling reactionThe above intermediate products andobtained by reaction
The X is selected from Cl, Br or I; the R, L1、Ar1、Ar2As defined above.
(II) when n is 1,
obtained by carbon-carbon coupling reactionThe above intermediate products andobtained by carbon-carbon coupling reactionThe above intermediate products andobtained by reaction
The two xs are the same or different and are independently selected from Cl, Br or I(ii) a The R, L1、L2、Ar1、Ar2、Ar3、Ar4As defined above.
The invention also provides an organic electroluminescent device comprising an anode, a cathode and an organic layer, wherein the organic layer is positioned between the anode and the cathode, and the organic layer comprises the triarylamine derivative.
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 a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a buffer layer interposed between the anode and the hole injection layer. The thickness of the organic material layer of the present invention is not more than 6 μm, preferably not more than 0.5 μm, and more preferably 0.02 to 0.5. mu.m.
In the organic electroluminescent device of the present invention, the compound of formula I may be used in any one or any plurality of the above organic layers, and is preferably contained in the light-emitting layer. The content is not particularly limited and may be appropriately adjusted as needed.
The organic electroluminescent device of the present invention is preferably:
substrate/anode/hole transport layer/luminescent layer/electron transport layer/metal cathode; or,
substrate/anode/hole transport layer/luminescent layer/electron transport layer/electron injection layer/metal cathode; or,
substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/metal cathode; or,
substrate/anode/hole injection layer/hole transport layer/luminescent layer/electron transport layer/electron injection layer/metal cathode; or,
substrate/anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/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 substrate according to the present invention is preferably a substrate having high light transmittance, such as a glass plate, a quartz plate, a polymer plate, and the like, but is not limited thereto.
The anode of the present invention is preferably made of a material having a high work function, such as Ag, Au, Al, Cu, Ni, Mo, Ti, Zn, Pd, Pt, or an alloy thereof; oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); conductive polymers such as polyaniline and polypyrrole; carbon black, and the like, but not limited thereto. The anode may have a single-layer structure or a multilayer structure having two or more layers, and the anode material contained in each layer may be a single material or a mixed material.
The cathode of the present invention is preferably a material having a low work function, such as a metal or an alloy thereof, for example, Ag, Al, Mg, Ti, etc., but is not limited thereto. The cathode may have a single-layer structure or a multi-layer structure of two or more layers, and the cathode material contained in each layer may be a single material or a mixed material.
The hole injection material of the present invention is preferably a material having a good hole injection property, for example, molybdenum oxide, titanium oxide, silver oxide, triarylamine derivative, benzidine derivative, phthalocyanine derivative, naphthalocyanine derivative, porphyrin derivative, polyvinylcarbazole, polysilane, a conductive polymer, or the like, but is not limited thereto. The hole injection layer may have a single-layer structure or a multilayer structure having two or more layers, and the hole injection material included in each layer may be a single material or a mixed material.
The hole transporting material of the present invention is preferably a material having a good hole transporting property, for example, triarylamine derivatives, benzidine derivatives, carbazole derivatives, anthracene derivatives, poly (N-vinylcarbazole) (PVK for short), poly (4-vinyltriphenylamine) (PVTPA for short), and the like, but is not limited thereto. The hole transport layer may have a single-layer structure or a multilayer structure having two or more layers, and the hole transport material included in each layer may be a single material or a mixed material.
The light-emitting layer of the present invention may contain one kind of material or two or more kinds of mixed materials, and preferably contains a host and a doped mixed material including a fluorescent light-emitting material and a phosphorescent light-emitting material. The fluorescent light-emitting material includes a blue fluorescent light-emitting material, for example, a pyrene derivative,A derivative, a fluoranthene derivative, a fluorene derivative, a triarylamine derivative, or the like, a green fluorescent light-emitting material such as a carbazole derivative, a triarylamine derivative, or the like, a red fluorescent light-emitting material such as a carbazole derivative, a triarylamine derivative, or the like. The phosphorescent light emitting material includes a blue phosphorescent light emitting material such as an iridium complex, a platinum complex, an osmium complex, etc., a green phosphorescent light emitting material such as an iridium complex, etc., a red phosphorescent light emitting material such as an iridium complex, a platinum complex, an europium complex, etc. The host material is preferably a material having a higher lowest unoccupied orbital level and a lower highest occupied orbital level than the dopant material, and examples thereof include an aluminum complex, a carbazole derivative, an anthracene derivative, a benzimidazole derivative, and a triarylamine derivative. But is not limited thereto.
The electron transport material of the present invention is preferably a material having a good electron transport property, for example, an aluminum complex, a zinc complex, an imidazole derivative, a benzimidazole derivative, a triazine derivative, a phenanthroline derivative, or the like, but is not limited thereto. The electron transport layer may have a single-layer structure or a multilayer structure having two or more layers, and the electron transport material contained in each layer may be a single material or a mixed material.
The electron injecting material of the present invention is preferably a material having a good electron injecting property, for example, an alkali metal, an alkaline earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, or the like, but is not limited thereto. The electron injection layer may have a single-layer structure or a multilayer structure having two or more layers, and the electron injection material included in each layer may be a single material or a mixed material.
The method for forming each layer of the organic electroluminescent element of the present invention is not particularly limited, and known methods such as a dry film forming method and a wet film forming method can be used. The dry film formation method includes a vacuum deposition method, a sputtering method, a plasma method, and the like. The wet film formation method includes, but is not limited to, spin coating, dipping, ink jet, and the like.
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.
Synthesis example 1: preparation of Compound I-1
Under argon protection, compound A1(27.3g,100mmol), compound B1(25.4g,150mmol), sodium tert-butoxide (28.8g,300mmol), tris (dibenzylideneacetone) dipalladium (1.4g,1.5mmol), 1 '-binaphthyl-2, 2' -bis-diphenylphosphine (1.9g,3mmol) and toluene (350ml) were added to a reaction flask 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 compound D1(30.7g, 85%).
Under argon protection, compound D1(11.2g,31mmol), compound E1(8.77g,31mmol), sodium tert-butoxide (2.98g,31mmol), bis (triphenylphosphine) palladium (II) dichloride (0.5g,0.71mmol) and xylene (500ml) were added to a reaction flask 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 compound M1(9.60g, 60%).
To the reaction flask were added compound M1(55.0g,106.6mmol), pinacol diboron (29.8g,117.3mmol), KOAc (31.4g,319.8mmol), Pd (dba) in this order2(1.7g,3mmol)、PCy3(1.7g,6mmol) and dioxane (500ml) were stirred under reflux for 12 h. After the reaction was completed, it was cooled to room temperature, filtered, and the filtrate was spin-dried to give a crude product, which was recrystallized from chloroform/ethyl acetate to give compound Sub-1(48.0g, 80%).
The compound 2-bromo-9-fluorenone (5.72g,22.1mmol), the compound Sub-1(12.44g,22.1mmol), Pd (PPh) were added to the reaction flask in this order3)4(0.81g,0.7mmol)、K2CO3(6.11g,44.2mmol)、THF(110ml)、H2O (55ml), stirred under reflux for 12 hours. After the reaction was completed, it was cooled to room temperature, extracted with dichloromethane, dried, filtered, and the crude product was purified by column chromatography to give compound G1(8.84G, 65%).
In a reaction flask, compound G1(8.00G,13.00mmol) was completely dissolved in 50ml of N, N-dimethylformamide, and the resulting solution was stirred at room temperature. To the reaction solution was added compound F1(1.00g,15.0mmol), and then the resulting solution was stirred at room temperature for 1 hour. After the reaction was completed, water was added thereto, and a precipitate produced by stirring the resulting solution for 10 minutes was filtered to obtain a residueThe resultant was diluted with ethyl acetate, water was removed over anhydrous magnesium sulfate, the residue was filtered, then concentrated under reduced pressure, and the concentrated solution was purified by silica gel column chromatography to prepare compound I-1(4.31g, 50%). Mass spectrum m/z: theoretical value: 663.82, respectively; measured value: 663.25. theoretical element content (%) C49H33N3: c, 88.66; h, 5.01; n, 6.33; measured elemental content (%): c, 88.64; h, 5.05; and N, 6.31. The above results confirmed that the obtained product was the objective product.
Synthesis example 2: preparation of Compound I-13
In the preparation method of compound G1 in synthesis example 1, compound G2(9.66G, 71%) was obtained by replacing compound E1 with an equimolar of compound E2, 2-bromo-9-fluorenone with an equimolar of 3-bromo-9-fluorenone, and the other steps were the same.
To a reaction flask were added compound G2(8.00G,13.0mmol), compound F2(1.52G,13.0mmol), sodium ethoxide (1.77G,26.0mmol) and ethanol (30ml) in this order, and the mixture was stirred under reflux for 2 hours. After completion of the reaction, it was cooled to room temperature, extracted with ethyl acetate, and the organic phases were combined, washed with water, dried, concentrated under reduced pressure, and purified by column chromatography to give compound I-13(5.39g, 58%). Mass spectrum m/z: theoretical value: 714.91, respectively; measured value: 714.29. theoretical element content (%) C54H38N2: c, 90.72; h, 5.36; n, 3.92; measured elemental content (%): c, 88.72; h, 5.40; and N, 3.90. The above results confirmed that the obtained product was the objective product.
Synthetic example 3: preparation of Compound I-16
In the preparation method of Compound I-13 in Synthesis example 2, Compound I-16(6.18g, 60%) was obtained in the same manner except that Compound A1 was replaced with equimolar Compound A2, Compound E2 was replaced with equimolar Compound E1, and Compound F2 was replaced with equimolar Compound F3. Mass spectrum m/z: theoretical value: 793.03, respectively; measured value: 792.37. theoretical element content (%) C60H44N2: c, 90.87; h, 5.59; n, 3.53; measured elemental content (%): c, 90.84; h, 5.64; n, 3.51. The above results confirmed that the obtained product was the objective product.
Synthetic example 4: preparation of Compound I-20
In the preparation method of Compound I-13 in Synthesis example 2, Compound I-20(5.56g, 53%) was obtained in the same manner except that Compound A1 was replaced with equimolar Compound A3, Compound E2 was replaced with equimolar Compound E1, and Compound F2 was replaced with equimolar Compound F4. Mass spectrum m/z: theoretical value: 807.05, respectively; measured value: 806.39. theoretical element content (%) C61H46N2: c, 90.78; h, 5.75; n, 3.47; measured elemental content (%): c, 90.74; h, 5.81; and N, 3.45. The above results confirmed that the obtained product was the objective product.
Synthesis example 5: preparation of Compound I-23
In the preparation method of Compound I-13 in Synthesis example 2, Compound I-23(5.32g, 51%) was obtained in the same manner except that Compound A1 was replaced with equimolar Compound A4, Compound B1 was replaced with equimolar Compound B2, and Compound E2 was replaced with equimolar Compound E1. Mass spectrum m/z: theoretical value: 803.02, respectively;measured value: 802.32. theoretical element content (%) C61H42N2: c, 91.24; h, 5.27; n, 3.49; measured elemental content (%): c, 91.22; h, 5.31; and N, 3.47. The above results confirmed that the obtained product was the objective product.
Synthetic example 6: preparation of Compound I-31
In the preparation method of Compound I-13 in Synthesis example 2, Compound I-31(4.82g, 49%) was obtained by replacing Compound A1 with equimolar Compound A5, Compound B1 with equimolar Compound B2, Compound E2 with equimolar Compound E1, and Compound F2 with equimolar Compound F5, in the same manner as the other steps. Mass spectrum m/z: theoretical value: 756.92, respectively; measured value: 756.26. theoretical element content (%) C56H37FN2: c, 88.86; h, 4.93; f, 2.51; n, 3.70; measured elemental content (%): c, 88.83; h, 4.99; f, 2.50; and N, 3.68. The above results confirmed that the obtained product was the objective product.
Synthetic example 7: preparation of Compound I-122
In the preparation method of Compound I-13 in Synthesis example 2, Compound I-122(5.60g, 46%) was obtained in the same manner except that Compound A1 was replaced with equimolar Compound A6, Compound E2 was replaced with equimolar Compound E1, and Compound F2 was replaced with equimolar Compound F6. Mass spectrum m/z: theoretical value: 936.03, respectively; measured value: 935.24. theoretical element content (%) C65H37F4N3: c, 83.41; h, 3.98; f, 8.12; n, 4.49; measured elemental content (%): c, 83.39; h, 4.02; f, 8.11; and N, 4.48. The above results confirmed that the obtained product was the objective product.
Synthesis example 8: preparation of Compound I-137
In the preparation method of Compound I-13 in Synthesis example 2, Compound I-137(6.45g, 57%) was obtained in the same manner except that Compound A1 was replaced with equimolar Compound A7, Compound E2 was replaced with equimolar Compound E3, and Compound F2 was replaced with equimolar Compound F7. Mass spectrum m/z: theoretical value: 871.14, respectively; measured value: 870.36. theoretical element content (%) C66H50N2: c, 91.00; h, 5.79; n, 3.22; measured elemental content (%): c, 90.97; h, 5.85; n, 3.19. The above results confirmed that the obtained product was the objective product.
Synthetic example 9: preparation of Compound I-148
In the preparation method of Compound I-13 in Synthesis example 2, Compound A1 was replaced with equimolar Compound A8, Compound B1 was replaced with equimolar B3, Compound E2 was replaced with equimolar E4, and Compound F2 was replaced with equimolar Compound F8, and the other steps were carried out in the same manner, to give Compound I-148(5.95g, 48%). Mass spectrum m/z: theoretical value: 953.03, respectively; measured value: 952.26. theoretical element content (%) C66H37F5N2: c, 83.18; h, 3.91; f, 9.97; n, 2.94; measured elemental content (%): c, 83.22; h, 3.91; f, 9.95; and N, 2.92. The above results confirmed that the obtained product was the objective product.
Synthetic example 10: preparation of Compound I-173
Synthesis example 2In the preparation of Compound I-13, Compound I-173(5.32g, 45%) was prepared by substituting compound A1 for equimolar Compound A9, Compound B1 for equimolar B2, Compound E2 for equimolar E5, and Compound F2 for equimolar F9. Mass spectrum m/z: theoretical value: 909.99, respectively; measured value: 909.22. theoretical element content (%) C63H35F4N3: c, 83.15; h, 3.88; f, 8.35; n, 4.62; measured elemental content (%): c, 83.12; h, 3.94; f, 8.33; and N, 4.61. The above results confirmed that the obtained product was the objective product.
Synthetic example 11: preparation of Compound I-181
In the preparation method of Compound I-13 in Synthesis example 2, Compound E2 was replaced with equimolar E6, and the other steps were carried out in the same manner to give Compound I-181(4.70g, 48%). Mass spectrum m/z: theoretical value: 753.91, respectively; measured value: 753.25. theoretical element content (%) C55H35N3O: c, 87.62; h, 4.68; n, 5.57; o, 2.12; measured elemental content (%): c, 87.59; h, 4.74; n, 5.55; o, 2.11. The above results confirmed that the obtained product was the objective product.
Synthetic example 12: preparation of Compound I-205
2-Bromofluorenone (2.59g,10mmol), compound D1(3.61g,10mmol), 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 under an argon atmosphere 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 compound G12(3.78G, 70%).
In a reaction flask, compound G12(7.02G,13.00mmol) was completely dissolved in 50ml of N, N-dimethylformamide, and the resulting solution was stirred at room temperature. To the reaction solution was added compound F1(1.00g,15.0mmol), and then the resulting solution was stirred at room temperature for 1 hour. After the reaction was completed, water was added thereto, and a precipitate generated by stirring the obtained solution for 10 minutes was filtered, the obtained residue was diluted with ethyl acetate, water was removed over anhydrous magnesium sulfate, the residue was filtered and then concentrated under reduced pressure, and the concentrated solution was purified by silica gel column chromatography to prepare compound I-205(4.28g, 56%). Mass spectrum m/z: theoretical value: 587.73, respectively; measured value: 587.22. theoretical element content (%) C43H29N3: c, 87.88; h, 4.97; n, 7.15; measured elemental content (%): c, 87.84; h, 5.03; and N, 7.13. The above results confirmed that the obtained product was the objective product.
Synthetic example 13: preparation of Compound I-219
In the preparation method of Compound I-205 in Synthesis example 12, Compound D1 was replaced with equimolar D13 and Compound F1 was replaced with equimolar F10, and the other steps were carried out in the same manner to obtain Compound I-219(4.70g, 52%). Mass spectrum m/z: theoretical value: 736.87, respectively; measured value: 736.25. theoretical element content (%) C53H34F2N2: c, 86.39; h, 4.65; f, 5.16; n, 3.80; measured elemental content (%): c, 86.36; h, 4.70; f, 5.15; n, 3.79. The above results confirmed that the obtained product was the objective product.
Synthesis example 14: preparation of Compound I-221
In the preparation method of Compound I-205 in Synthesis example 12, Compound I-221(4.80g, 49%) was obtained by replacing compound D1 with equimolar D14 and compound F1 with equimolar F8. Mass spectrum m/z: theoretical value: 752.79, respectively; measured value: 752.22. theoretical element content (%) C50H29F5N2: c, 79.78; h, 3.88; f, 12.62; n, 3.72; measured elemental content (%): c, 79.76; h, 3.94; f, 12.61; and N, 3.70. The above results confirmed that the obtained product was the objective product.
Synthetic example 15: preparation of Compound I-224
In the preparation method of Compound I-205 in Synthesis example 12, Compound D1 was replaced with equimolar D4 and Compound F1 was replaced with equimolar F6, and the other steps were carried out in the same manner to give Compound I-224(5.21g, 51%). Mass spectrum m/z: theoretical value: 785.85, respectively; measured value: 785.24. theoretical element content (%) C53H31F4N3: c, 81.01; h, 3.98; f, 9.67; n, 5.35; measured elemental content (%): c, 81.00; h, 4.04; f, 9.64; n, 5.33. The above results confirmed that the obtained product was the objective product.
Synthetic example 16: preparation of Compound I-226
In the preparation method of Compound I-205 in Synthesis example 12, Compound D1 was replaced with equimolar D16 and Compound F1 was replaced with equimolar F9, and the other steps were carried out in the same manner to give Compound I-226(5.91g, 53%). Mass spectrum m/z: theoretical value: 857.91, respectively; measured value: 857.22. theoretical element content (%) C59H31F4N3: c, 82.60; h, 3.64; f, 8.86; n, 4.90; measured elemental content (%): c, 82.58; h, 3.70; f, 8.85; and N, 4.87. The above results confirmed that the obtained product was the objective product.
Synthetic example 17: preparation of Compound I-229
In the preparation of Compound I-205 in Synthesis example 12, 2-bromofluorenone was changed to equimolar 2, 7-dibromofluorenone, and Compound D1 was changed to twice the molar D17, and the other steps were the same, to give Compound I-229(5.68g, 55%). Mass spectrum m/z: theoretical value: 795.00, respectively; measured value: 794.33. theoretical element content (%) C58H42N4: c, 87.63; h, 5.33; n, 7.05; measured elemental content (%): c, 87.61; h, 5.37; and N, 7.03. The above results confirmed that the obtained product was the objective product.
Other target products shown in structural formula I were synthesized by reference to the synthetic methods of examples 1-17 above.
Application example 1: preparation of organic electroluminescent device 1
Selecting ITO glass as an anode, ultrasonically cleaning, drying in a vacuum cavity, and vacuumizing to 5 x 10-5Pa, 2-TNATA was vacuum-deposited as a hole injection layer on the anode substrate to a thickness of 60 nm. NPB was vacuum-deposited on the hole injection layer as a hole transport layer, and the thickness of the deposition was 20 nm. Vacuum evaporation of host Material Compound I-13 of the invention, 10 wt% of guest Material Ir (ppy)3The light-emitting layer was deposited to a thickness of 30 nm. BAlq was vacuum-deposited on the light-emitting layer as a hole-blocking layer to a thickness of 10 nm. Vacuum evaporation of Alq on hole blocking layer3The electron transport layer was deposited to a thickness of 40 nm. LiF is evaporated on the electron transport layer in vacuum to form an electron injection layer, and 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 organic electroluminescent device 2
Compound I-13 in practical example 1 was replaced with Compound I-16, and the other procedures were the same as in practical example 1.
Application example 3: preparation of organic electroluminescent device 3
Compound I-13 in application example 1 was replaced with Compound I-20, and the other procedures were the same as in application example 1.
Application example 4: preparation of organic electroluminescent device 4
Compound I-13 in application example 1 was replaced with Compound I-23, and the other procedures were the same as in application example 1.
Application example 5: preparation of organic electroluminescent device 5
Compound I-13 in application example 1 was replaced with Compound I-137, and the other procedures were the same as in application example 1.
Comparative example 1
Selecting ITO glass as an anode, ultrasonically cleaning, drying in a vacuum cavity, and vacuumizing to 5 x 10-5Pa, 2-TNATA was vacuum-deposited as a hole injection layer on the anode substrate to a thickness of 60 nm. NPB was vacuum-deposited on the hole injection layer as a hole transport layer, and the thickness of the deposition was 20 nm. Vacuum evaporation of host material CBP, 10 wt% guest material Ir (ppy) on the hole transport layer3The light-emitting layer was deposited to a thickness of 30 nm. BAlq was vacuum-deposited on the light-emitting layer as a hole-blocking layer to a thickness of 10 nm. Vacuum evaporation of Alq on hole blocking layer3The electron transport layer was deposited to a thickness of 40 nm. LiF is evaporated on the electron transport layer in vacuum to form an electron injection layer, and 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 the test of the light emitting characteristics of the light emitting organic electroluminescent devices prepared in application examples 1 to 5 of the present invention and comparative example 1 are shown in table 1.
TABLE 1
Application example 6: preparation of organic electroluminescent device 6
Selecting ITO glass as an anode, ultrasonically cleaning, drying in a vacuum cavity, and vacuumizing to 5 x 10-5Pa, 2-TNATA was vacuum-deposited as a hole injection layer on the anode substrate to a thickness of 60 nm. NPB was vacuum-deposited on the hole injection layer as a hole transport layer, and the thickness of the deposition was 20 nm. Vacuum evaporation of 40 wt% Compound I-1 of the invention, 50 wt% TcTa, 10 wt% Ir (piq) on hole transport layer2(acac) as a light-emitting layer, the thickness of vapor deposition was 30 nm. BAlq was vacuum-deposited on the light-emitting layer as a hole-blocking layer to a thickness of 10 nm. Vacuum evaporation of Alq on hole blocking layer3The electron transport layer was deposited to a thickness of 40 nm. LiF is evaporated on the electron transport layer in vacuum to form an electron injection layer, and 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 7: preparation of organic electroluminescent device 7
Compound I-1 in application example 1 was replaced with Compound I-13, and the other procedures were the same as in application example 1.
Application example 8: preparation of organic electroluminescent device 8
Compound I-1 in application example 1 was replaced with Compound I-122, and the other procedures were the same as in application example 1.
Application example 9: preparation of organic electroluminescent device 9
Compound I-1 in practical example 1 was replaced with Compound I-148, and the other procedures were the same as in practical example 1.
Application example 10: preparation of organic electroluminescent device 10
Compound I-1 in application example 1 was replaced with Compound I-173, and the other procedures were the same as in application example 1.
Application example 11: preparation of organic electroluminescent device 1
Compound I-1 in application example 1 was replaced with Compound I-181, and the other procedures were the same as in application example 1.
Application example 12: preparation of organic electroluminescent device 12
Compound I-1 in application example 1 was replaced with Compound I-229, and the other procedures were the same as in application example 1.
Comparative example 2:
selecting ITO glass as an anode, ultrasonically cleaning, drying in a vacuum cavity, and vacuumizing to 5 x 10-5Pa, 2-TNATA was vacuum-deposited as a hole injection layer on the anode substrate to a thickness of 60 nm. NPB was vacuum-deposited on the hole injection layer as a hole transport layer, and the thickness of the deposition was 20 nm. Vacuum evaporation of 40 wt% SPPO13, 50 wt% TcTa, 10 wt% Ir (piq) on the hole transport layer2(acac) as a light-emitting layer, the thickness of vapor deposition was 30 nm. BAlq was vacuum-deposited on the light-emitting layer as a hole-blocking layer to a thickness of 10 nm. Vacuum evaporation of Alq on hole blocking layer3The electron transport layer was deposited to a thickness of 40 nm. LiF is evaporated on the electron transport layer in vacuum to form an electron injection layer, and 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 the test of the light emitting characteristics of the light emitting organic electroluminescent devices prepared in application examples 6 to 12 of the present invention and comparative example 2 are shown in table 2.
TABLE 2
Application example 13: preparation of organic electroluminescent device 13
Selecting ITO glass as an anode, ultrasonically cleaning, drying in a vacuum cavity, and vacuumizing to 5 x 10-5Pa, 2-TNATA was vacuum-deposited as a hole injection layer on the anode substrate to a thickness of 60 nm. NPB was vacuum-deposited on the hole injection layer as a hole transport layer, and the thickness of the deposition was 20 nm. Vacuum evaporation of 40 wt% of Compound I-205 of the present invention, 50 wt% of TcTa, 10 wt% of Ir (ppy)3The light-emitting layer was deposited to a thickness of 30 nm. BAlq was vacuum-deposited on the light-emitting layer as a hole-blocking layer to a thickness of 10 nm. Vacuum evaporation of Alq on hole blocking layer3The electron transport layer was deposited to a thickness of 40 nm. LiF is evaporated on the electron transport layer in vacuum to form an electron injection layer, and 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 14: preparation of organic electroluminescent device 14
Compound I-205 in application example 1 was replaced with Compound I-219, and the other procedures were the same as in application example 1.
Application example 15: preparation of organic electroluminescent device 15
Compound I-205 in application example 1 was replaced with Compound I-221, and the other procedures were the same as in application example 1.
Application example 16: preparation of organic electroluminescent device 16
Compound I-205 in application example 1 was replaced with Compound I-224, and the other procedures were the same as in application example 1.
Application example 17: preparation of organic electroluminescent device 17
Compound I-226 in application example 1 was replaced with Compound I-226, and the other procedures were the same as in application example 1.
Comparative example 3:
selecting ITO glass as an anode, ultrasonically cleaning, drying in a vacuum cavity, and vacuumizing to 5 x 10-5Pa, 2-TNATA was vacuum-deposited as a hole injection layer on the anode substrate to a thickness of 60 nm. NPB was vacuum-deposited on the hole injection layer as a hole transport layer, and the thickness of the deposition was 20 nm. Vacuum evaporation of 40 wt% SPPO13, 50 wt% TcTa, 10 wt% Ir (ppy) on the hole transport layer3The light-emitting layer was deposited to a thickness of 30 nm. BAlq was vacuum-deposited on the light-emitting layer as a hole-blocking layer to a thickness of 10 nm. Vacuum evaporation of Alq on hole blocking layer3The electron transport layer was deposited to a thickness of 40 nm. LiF is evaporated on the electron transport layer in vacuum to form an electron injection layer, and 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 the test of the light emitting characteristics of the light emitting organic electroluminescent devices prepared in application examples 13 to 17 of the present invention and comparative example 3 are shown in Table 3.
TABLE 3
As can be seen from tables 1, 2 and 3, the organic electroluminescent device containing the host material of the present invention has a lower driving voltage, a higher luminous efficiency and a longer lifetime.

Claims (10)

1. A triarylamine derivative is characterized in that the triarylamine derivative has a structural general formula shown as a structural formula I,
wherein R is selected from one of cyano, halogen, substituted or unsubstituted aryl of C6-C18, and substituted or unsubstituted heteroaryl of C3-C18;
said L1、L2Independently selected from single bond, substituted or notOne of substituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C3-C30;
n is selected from 0 or 1;
ar is2、Ar3Independently selected from one of substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C3-C30;
ar is1、Ar4Independently selected from one of the groups shown below,
rx and Ry are independently selected from one of substituted or unsubstituted C1-C10 alkyl and substituted or unsubstituted C6-C18 aryl,
l is selected from substituted or unsubstituted arylene of C6-C18,
a is selected from one of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl and substituted or unsubstituted indenyl,
and B is selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl and substituted or unsubstituted indenyl.
2. A triarylamine derivative according to claim 1, wherein R is selected from one of the following groups,
the R is1、R2、R3、R4、R5、R6、R7、R8Independently selected from one of hydrogen, cyano, halogen, trifluoromethyl, trichloromethyl, trifluoromethoxy, methyl, ethyl, propyl, butyl, pentyl and hexyl.
3. According toA triarylamine derivative according to claim 1 wherein L is a compound represented by formula1、L2Independently selected from single bond or selected from one of the following groups,
said X0Selected from O or S;
said X1、X2、X3、X4、X5、X6、X7、X8、X9、X10Independently selected from N or C (R)0) Said R is0One selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C1-C18 heteroaryl.
4. A triarylamine derivative according to claim 1 wherein Ar is selected from the group consisting of1、Ar4Independently selected from one of the groups shown below,
5. a triarylamine derivative according to claim 1, wherein R is selected from one of the following groups,
6. a triarylamine derivative according to claim 1 wherein L is an aryl amine derivative1、L2Independently selected from a single bond or one of the groups shown below,
7. a triarylamine derivative according to claim 1 wherein Ar is selected from the group consisting of2、Ar3Independently selected from one of the groups shown below,
8. a triarylamine derivative according to claim 1, wherein the triarylamine derivative represented by formula I is selected from one of the following formulae,
9. an organic electroluminescent device comprising an anode, a cathode and an organic layer, the organic layer being located between the anode and the cathode, the organic layer comprising a triarylamine derivative according to any one of claims 1 to 8.
10. An organic electroluminescent device according to claim 9, wherein the organic layer comprises a light-emitting layer comprising a host material and a guest material, the host material comprising the triarylamine derivative according to any one of claims 1 to 8.
CN201811156604.XA 2018-09-30 2018-09-30 A kind of triarylamine derivative and its organic electroluminescence device Withdrawn CN109180528A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115636755A (en) * 2022-12-26 2023-01-24 烟台显华科技集团股份有限公司 Naphthyl substituted diarylamine compound and application thereof
CN115710186A (en) * 2022-10-27 2023-02-24 上海八亿时空先进材料有限公司 Fluorene derivative and application thereof
WO2024109552A1 (en) * 2022-11-22 2024-05-30 Tcl科技集团股份有限公司 Manufacturing method for light-emitting device, light-emitting device, and electronic apparatus

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115710186A (en) * 2022-10-27 2023-02-24 上海八亿时空先进材料有限公司 Fluorene derivative and application thereof
WO2024109552A1 (en) * 2022-11-22 2024-05-30 Tcl科技集团股份有限公司 Manufacturing method for light-emitting device, light-emitting device, and electronic apparatus
CN115636755A (en) * 2022-12-26 2023-01-24 烟台显华科技集团股份有限公司 Naphthyl substituted diarylamine compound and application thereof

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Application publication date: 20190111