CN114430010A - Organic electroluminescent composition and organic electroluminescent device - Google Patents
Organic electroluminescent composition and organic electroluminescent device Download PDFInfo
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- CN114430010A CN114430010A CN202210038734.3A CN202210038734A CN114430010A CN 114430010 A CN114430010 A CN 114430010A CN 202210038734 A CN202210038734 A CN 202210038734A CN 114430010 A CN114430010 A CN 114430010A
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K50/14—Carrier transporting layers
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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Abstract
The invention relates to the field of organic electroluminescence, in particular to an organic electroluminescent composition and an organic electroluminescent device. The organic electroluminescent composition comprises arylamine derivatives shown in a formula I for forming a hole transport region and fused azulene derivatives shown in a formula II for forming a light-emitting layer,
and
Description
Technical Field
The invention relates to the field of organic electroluminescence, in particular to an organic electroluminescent composition and an organic electroluminescent device.
Background
The organic electroluminescent device technology can be used for manufacturing novel display products and novel illumination products, is expected to replace the existing liquid crystal display and fluorescent lamp illumination, and has wide application prospect. When voltage is applied to the electrodes at two ends of the organic electroluminescent device and an electric field acts on positive and negative charges in the organic layer functional material film layer, the positive and negative charges are further compounded in the organic light-emitting layer, and organic electroluminescence is generated.
The organic electroluminescent device generally has a multilayer structure, a reasonable device structure can effectively improve the performance of the device, specifically, various auxiliary functional layers except for a light emitting layer play a crucial role in the performance of the device, and hole transport regions such as an electron injection layer, an electron transport layer, a hole blocking layer, a second hole transport layer, a hole transport layer and a hole injection layer are widely used for improving the performance of the device.
Therefore, there is a continuing need to develop organic electroluminescent devices having excellent luminous efficiency and lifetime.
Disclosure of Invention
The invention provides an organic electroluminescent composition and an organic electroluminescent device, and aims to provide an organic electroluminescent device with characteristics of low driving voltage, high luminous efficiency and/or long service life.
The invention is realized by the following steps:
in a first aspect, embodiments of the present invention provide organic electroluminescent compositions comprising arylamine derivatives represented by formula I for forming a hole transport region and fused azulene derivatives represented by formula II for forming a light emitting layer,
wherein Ar is1And Ar2Independently selected from any one of the functional groups formed by substituted or unsubstituted C6-C24 aryl and substituted or unsubstituted 3-to 24-membered heteroaryl;
R′1-R′3each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted 3-to 18-membered heteroaryl, substituted or unsubstitutedAny one of the functional groups formed by substituted C3-C12 cycloalkyl and substituted or unsubstituted C1-C6 alkoxy; r'4Any one selected from hydrogen, methyl, ethyl, isopropyl and phenyl; or R'1-R′4A condensed ring is formed with the benzene ring and/or the adjacent ring;
ar is any one of functional groups formed by hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted 3-to 30-membered heteroaryl;
R1-R4each independently selected from any one of the group of functional groups consisting of hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C24 aryl, and substituted or unsubstituted 3-to 24-membered heteroaryl.
In a second aspect, embodiments of the present invention provide an organic electroluminescent device comprising a hole transport region formed from an arylamine derivative represented by formula i and a light-emitting layer formed from a fused azulene derivative represented by formula II, the hole transport region and the light-emitting layer being connected.
The invention has the beneficial effects that: the organic electroluminescent device formed by combining the compounds shown in the formula I and the compound shown in the formula II for forming the hole transport region through specific selection can have the characteristics of low driving voltage, high luminous efficiency and/or long service life.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The following provides a detailed description of an organic electroluminescent composition and an organic electroluminescent device according to embodiments of the present invention.
In a first aspect, embodiments of the present invention provide organic electroluminescent compositions comprising arylamine derivatives according to formula i for forming a hole transport region and fused azulene derivatives according to formula II for forming a light emitting layer.
Wherein,
ar in formula I1And Ar2Independently selected from any one of the functional groups formed by substituted or unsubstituted C6-C24 aryl and substituted or unsubstituted 3-to 24-membered heteroaryl;
R′1-R′3each independently selected from any one of the functional groups formed by hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted 3-to 18-membered heteroaryl, substituted or unsubstituted C3-C12 cycloalkyl and substituted or unsubstituted C1-C6 alkoxy; r'4Any one selected from hydrogen, methyl, ethyl, isopropyl and phenyl; or R'1-R′4Form a condensed ring with the benzene ring and/or the adjacent ring.
R 'is defined as'1-R′4The definition of (1) includes 2 cases: (1) r'1-R′4No fused ring is formed, and the fused ring is only a substituent corresponding to any position of a benzene ring, and the substituent is any one of the functional group groups; (2) r'1-R′4At least one of which forms a fused ring, and which may be R'1-R′4The condensed ring formed with the benzene ring may be R'1-R′4Fused rings formed with the benzene ring in which it is located and with adjacent rings. At this time, R 'of a condensed ring is formed'1-R′4Is any one of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and substituted or unsubstituted cycloalkyl, and the rest is R'1-R′4Still is a substituent corresponding to any position of the benzene ring, and the substituent is selected from any one of the above functional group groups.
Further, Ar1And Ar2Independently selected from any one of the following groups of functional groups:
in addition, Ar is1And Ar2Ar is selected from substituted or unsubstituted (C6-C24) aryl, substituted or unsubstituted (3-to 24-membered) heteroaryl, or a group represented by the formula1And Ar2Any available position of the substituent shown is linked to N.
Further, R 'is'1-R′3The substituted or unsubstituted C1-C6 alkyl groups in the selection include, but are not limited to, methyl, ethyl, propyl, t-butyl, and the like, the substituted or unsubstituted C6-C24 aryl groups include, but are not limited to, phenyl, naphthyl, biphenyl, and the like, the substituted or unsubstituted 3-to 18-membered heteroaryl groups include, but are not limited to, phenylpyridyl, phenanthryl, dibenzofuranyl, dimethylfluorenyl, and furanyl, and the like, the substituted or unsubstituted C3-C12 cycloalkyl groups include, but are not limited to, cyclopropane groups, and the like, and the substituted or unsubstituted C1-C6 alkoxy groups include, but are not limited to, methoxy, ethoxy, and the like.
Preferably, R'1-R′2Any one of functional groups selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, methoxy, phenanthryl, dibenzofuranyl, and dimethylfluorenyl;
R′3and the functional group is any one of deuterium, methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, methoxy, phenanthryl, dimethylfluorenyl and furyl.
Further, the compound shown in the formula I is selected from any one of the compounds shown in the following structural formulas:
ar in the above formulae I-1 to I-31、Ar2And R'1-R′4Reference is made to the choices in formula I above.
Further, the compound shown in the formula I is selected from any one of the compounds shown in the following structural formulas:
the compounds of formula I provided in the examples of the present invention may be produced by reference to the following reaction scheme:
N2under protection, adding the reactant A, the reactant B, the tetrakis (triphenylphosphine) palladium and the potassium carbonate into a mixed solvent of toluene, ethanol and water respectively in a reaction vessel, heating to 105 ℃, reacting for 8 hours, cooling to room temperature after the reaction is finished, performing suction filtration after solid precipitation is finished, and drying a filter cake. Recrystallizing in 1, 4-dioxane to obtain formula I.
Further, the compound of formula II is:
wherein L represents any one of a connecting bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted 3-to 30-membered heteroarylene group;ar is any one of functional groups formed by hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted 3-to 30-membered heteroaryl; r1-R4Each independently selected from any one of the group of functional groups consisting of hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C24 aryl, and substituted or unsubstituted 3-to 24-membered heteroaryl; or R1-R4Form a condensed ring with the benzene ring and/or the adjacent ring.
In addition, R is1-R4Is the same as R 'in the formula I'1-R′4The same is explained for the definitions of (A).
Further, L is independently selected from any one of a linking bond, biphenyl, pyrimidinyl, triazinyl, and a group of functional groups formed from the group consisting of;
ar is any one of hydrogen, deuterium, methyl, pyrimidyl, triazinyl and a functional group formed by the following groups;
wherein R is5-R6Each independently selected from any one of the group of functional groups consisting of hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted 3-to 18-membered heteroaryl; for example, R5-R6And any one of functional groups formed by hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, pyrimidyl, triazinyl and methoxy. However, it is to be noted that R5-R6The above-mentioned specific groups are not limited, and the above-mentioned groups are merely examples.
Further, R1-R4Each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, pyrimidyl, triazinyl and methoxyAny one of them. However, it is to be noted that R1-R4The above-mentioned specific groups such as methyl, ethyl, naphthyl, triazinyl and methoxy are not limited thereto, and the above-mentioned groups are merely examples.
Further, the compound shown in the formula II is selected from any one of the compounds shown in the following structural formulas:
wherein L, Ar and R in the formulae II-1 to II-4 are1-R4With reference to L, Ar in formula II and R1-R4The definition of (1).
Further, the compound shown in the formula II is selected from any one of the compounds shown in the following structural formulas:
the compounds of formula II provided in the examples of the present invention may be produced by reference to the following reaction scheme:
in particular, N2Adding a reactant a and a reactant b into a reaction vessel to be dissolved under protectionAfter toluene, Pd was added2(dba)3、P(t-Bu)3t-BuONa. After the addition, the temperature was raised to 110 ℃ to react for 8 hours. Suction filtration is carried out with diatomaceous earth while hot, the salts and the catalyst are removed, the filtrate is cooled to room temperature, the solvent is removed with a rotary evaporator, the solid obtained is dried and passed through a silica gel funnel with dichloromethane: petroleum ether volume ratio of 1 (1-4) is used as eluent, filtrate is removed by a rotary evaporator, and the obtained solid is dried, and the formula II is shown.
The second aspect, hereinafter, will describe the present disclosure in detail. However, the following description is intended to explain the disclosure and is not meant to limit the scope of the disclosure in any way.
The present invention can provide an organic electroluminescent device having low driving voltage, high luminous efficiency and/or long life characteristics by including the compound represented by formula I in the second hole transport layer in a specific combination with the compound represented by formula II in the light emitting layer.
The organic electroluminescent device of the present invention may be of a top emission type, a bottom emission type, or a bidirectional emission type. The device of the invention can be used for an organic light-emitting device, an organic solar cell, electronic paper, an organic photoreceptor or an organic thin film transistor.
The organic electroluminescent device of the present invention includes a first electrode, a second electrode facing the first electrode, a light-emitting layer between the first electrode and the second electrode, a hole transport region between the first electrode and the light-emitting layer, and an electron transport region between the light-emitting layer and the second electrode. One of the first electrode and the second electrode is an anode, and the other is a cathode.
The organic light-emitting element may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a second hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting element is not limited thereto, and a smaller or larger number of organic layers may be included.
The organic light emitting element can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. The substrate can be produced by a Physical Vapor Deposition (PVD) method such as a sputtering method or an electron beam evaporation (ebeam evaporation) method.
A first electrode is formed by depositing metal or a metal oxide having conductivity or an alloy thereof on a substrate, an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the first electrode, and a substance which can be used as a second electrode is deposited on the organic layer. In addition to the above method, the second electrode material, the organic layer, and the first electrode material may be sequentially deposited on the substrate to manufacture the organic light-emitting element.
In addition, in the case of producing an organic light-emitting element, the compound represented by the formula I or II may be formed into an organic layer by not only a vacuum deposition method but also a solution coating method. The solution coating method is not limited to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like.
The first electrode is an anode, and the second electrode is a cathode.
The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material usable in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO A1 or SnO2A combination of a metal such as Sb and an oxide; and conductive polymers such as polypyrrole and polyaniline.
The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof: LiF/A1 or LiO2A multilayer structure substance such as/A1, Mg/Ag, etc.
The hole transport region means a region in which holes are transported between the first electrode and the light emitting layer. The hole transport region is a region that receives holes from the hole injection layer and transports the holes to the light emitting layer. A hole transport region may be placed between the anode (or hole injection layer) and the light emitting layer. The hole transport region may serve to smoothly move holes transferred from the anode to the light emitting layer and block electrons transferred from the cathode to remain in the light emitting layer.
The hole transport region comprises a hole injection layer, a first hole transport layer and a second hole transport layer, wherein the second hole transport layer can also be used as a light-emitting auxiliary layer or an electron blocking layer in the embodiment of the invention.
In the present invention, the hole injection layer is preferably a p-doped hole injection layer, which means a hole injection layer doped with a p-dopant. The p-dopant is a material capable of imparting p-type semiconductor characteristics. The p-type semiconductor characteristics mean the characteristics of injecting holes or transporting holes at the HOMO level, that is, the characteristics of a material having high hole conductivity.
The second hole transport layer may be placed between the anode and the light emitting layer, or between the cathode and the light emitting layer. When the second hole transport layer is placed between the anode and the light emitting layer, it may be used to facilitate hole injection and/or hole transport, or to prevent electron overflow. When the second hole transport layer is placed between the cathode and the light emitting layer, it may be used to facilitate electron injection and/or electron transport, or to prevent holes from overflowing.
The light-emitting substance in the light-emitting layer is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having a high quantum efficiency with respect to fluorescence or phosphorescence.
The light emitting layer may include a host material and a dopant material.
The electron transport region may include at least one of an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and preferably at least one of an electron transport layer and an electron injection layer. The electron transport region is a layer capable of improving the problem of deterioration of light emission luminance due to a change in current characteristics in the device when the device is exposed to high temperature during the process of manufacturing the panel, and it can control charge flow characteristics.
There is no particular limitation on the material of the other layers in the OLED device, except for the specific combination of formula I in the second hole transport layer and formula II in the light emitting layer disclosed herein. Existing hole injection materials, hole transport materials, dopant materials, hole blocking layer materials, electron transport layer materials, and electron injection materials may be used.
Examples of the hole injection layer material include metalloporphyrin, oligothiophene, arylamine derivatives, hexanenitrile hexaazatriphenylene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer, and the P-doped P-dopant can be exemplified by the following compounds, but is not limited thereto.
The first hole transport material may be selected from arylamine derivatives, conductive polymers, block copolymers in which a conjugated portion and a non-conjugated portion are present at the same time, and the like, and specifically, the first hole transport material is selected from the following compounds, but is not limited thereto.
The second hole transport layer is a compound represented by the general formula I.
The main material is a compound shown as a general formula II in the invention.
The dopant material is selected from red light dopant material, aromatic amine derivative, styryl amine compound, boron complex, fluoranthene compound, metal complex, etc. Specifically, the red-light-doped material of the present invention is selected from the following compounds, but is not limited thereto.
The material of the electron transport layer (hole blocking layer), derivatives such as oxazole, imidazole, thiazole, triazine, metal chelate compounds, quinoline derivatives, quinoxaline derivatives, diazaanthracene derivatives, phenanthroline derivatives, heterocyclic compounds containing silicon, perfluorinated oligomers, and the like, and specifically, the material of the electron transport layer is selected from the following compounds, but is not limited thereto.
Specific examples of the electron injection layer material include, but are not limited to, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, derivatives thereof, metal complexes, and nitrogen-containing 5-membered ring derivatives.
The organic electroluminescent composition and the organic electroluminescent device provided by the present invention are specifically described below with reference to specific examples.
The preparation method of the organic electroluminescent device comprises the following steps:
a. an ITO anode: cleaning an ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate with the coating thickness of 150nm in distilled water for 2 times, ultrasonically cleaning for 30min, repeatedly cleaning for 2 times by using distilled water, ultrasonically cleaning for 10min, transferring to a spin dryer for spin-drying after the cleaning is finished, finally baking for 2 hours at 220 ℃ by using a vacuum oven, and cooling after the baking is finished. The substrate is taken as an anode, a device evaporation process is carried out by using an evaporation machine, and other functional layers are sequentially evaporated on the substrate;
b. HIL (hole injection layer): to be provided with
The hole injection layer materials HT-a and P-dopant are vacuum evaporated, and the chemical formulas are shown as follows. The evaporation rate ratio of HT-a to P-dock is 97: 3, the thickness is 10 nm;
c. HTL (first hole transport layer): to be provided with
The evaporation rate of (2), and evaporating 125nm HT-a on the hole injection layer in vacuum to form a hole transport layer;
d. second hole transport layer: to be provided with
Vacuum evaporation of 90nm of the compound of formula I provided in the examples of the present invention or comparative compounds 1 to 9, respectively, as a second hole transport layer on top of the hole transport layer;
e. EML (light-emitting layer): and then on the second hole transport layer, to
The Host material (Host) and the Dopant material (Dopant-1) of the compound represented by the formula II provided in the example of the present invention or the comparative compound 10-14 were vacuum-evaporated to a thickness of 40nm, respectively, as the light emitting layer, wherein the ratio of the evaporation rates of Host and Dopant was 97: 3;
f. HB (hole blocking layer): to be provided with
The evaporation rate of (1) and vacuum evaporation of the hole blocking layer HB-1 with the thickness of 5.0 nm;
g. ETL (electron transport layer): to be provided with
And vacuum evaporating ET-1 and Liq with the thickness of 30nm as electron transport layers, wherein the evaporation rate ratio of ET-1 to Liq is 50: 50;
h. EIL (electron injection layer): to be provided with
The evaporation rate of (1.0 nm) of the Yb film layer is evaporated to form an electron injection layer;
i. cathode: to be provided with
The evaporation rate ratio of (1) is 18nm, the evaporation rate ratio of magnesium to silver is 1:9, and a cathode is formed;
j. light extraction layer: to be provided with
The evaporation rate of (1), CPL-1 with a thickness of 70nm is evaporated on the cathode in vacuum to be used as a light extraction layer;
k. and packaging the substrate subjected to evaporation. Firstly, coating the cleaned back cover plate by using UV glue by using gluing equipment, then moving the coated cover plate to a pressing working section, placing the evaporated base plate on the upper end of the cover plate, finally, attaching the base plate and the cover plate under the action of attaching equipment, and simultaneously, finishing the illumination and curing of the UV glue.
Structure of organic electroluminescent device:
ITO/Ag/ITO/HT-a: P-dot (10nm)/HT-a (125 nm)/compound of formula I or comparative compound 1-9(90 nm)/compound of formula II or comparative compound 10-14: dot-1 (40nm)/HB (5nm)/ET-1: Liq (30nm)/Yb (1nm)/Mg: Ag (18nm)/CPL (70 nm).
Wherein the structural formula of the specific compound is shown in table 1:
structural formula of the Compound of Table 1
It should be noted that the synthesis of HT-1, HT-4, HT-8, HT-9, HT-10, HT-11, HT-12, HT-17, HT-20, HT-24, HT-29, HT-31, HT-36, HT-38, HT-40 and HT-44 described above can be found in CN111440156A, CN111785841A, and the detailed description of the embodiments of the present invention is omitted.
The synthesis of RH-23, RH-37, RH-44, RH-60 and RH-78 can be found in CN110268542A, and the detailed description of the embodiments of the present invention is omitted.
The specific examples are as follows:
examples 1 to 16
The organic electroluminescent devices of examples 1 to 16 were prepared according to the above-described method for preparing organic electroluminescent devices, using the compound RH-23 shown in Table 1 as a host material of the light emitting layer, and HT-1, HT-4, HT-8, HT-9, HT-10, HT-11, HT-12, HT-17, HT-20, HT-24, HT-29, HT-31, HT-36, HT-38, HT-40, and HT-44 were used to form the second hole transporting layer.
Comparative examples 1 to 9
An organic electroluminescent device was prepared according to the above-described method for preparing an organic electroluminescent device, using compound RH-23 shown in table 1 as a host material, and comparative compound 1 to comparative compound 9 for forming a second hole transport layer.
Comparative examples 10 to 25
The organic electroluminescent device was prepared according to the above-described method for preparing an organic electroluminescent device, using comparative compound 10 shown in Table 1 as a host material, and HT-1, HT-4, HT-8, HT-9, HT-10, HT-11, HT-12, HT-17, HT-20, HT-24, HT-29, HT-31, HT-36, HT-38, HT-40, and HT-44 were used to form the second hole transport layer.
The organic electroluminescent devices obtained in examples 1 to 16 and comparative examples 1 to 25 were characterized at a luminance of 6000(nits), and the driving voltage, the luminous efficiency, and the lifetime were measured, and the test results are shown in table 2:
TABLE 2 test results of luminescence characteristics (luminance value of 6000nits)
Examples 17 to 32
The organic electroluminescent devices of examples 17 to 32 were prepared according to the above-described method for preparing organic electroluminescent devices, and HT-1, HT-4, HT-8, HT-9, HT-10, HT-11, HT-12, HT-17, HT-20, HT-24, HT-29, HT-31, HT-36, HT-38, HT-40, and HT-44, which were the compounds shown in Table 1, were used to form the second hole transport layer, as host materials.
Comparative examples 26 to 34
An organic electroluminescent device was prepared according to the above-described method for preparing an organic electroluminescent device, using the compound RH-37 shown in table 1 as a host material, and comparative compound 1 to comparative compound 9 for forming a second hole transport layer.
Comparative examples 35 to 50
An organic electroluminescent device was prepared according to the above-described method for preparing an organic electroluminescent device, using comparative compound 11 shown in Table 1 as a host material, and HT-1, HT-4, HT-8, HT-9, HT-10, HT-11, HT-12, HT-17, HT-20, HT-24, HT-29, HT-31, HT-36, HT-38, HT-40, and HT-44 were used to form the second hole transport layer.
The organic electroluminescent devices obtained in the above device examples 17 to 32 and device comparative examples 26 to 50 were characterized for driving voltage, luminous efficiency, and lifetime at 6000(nits) luminance, and the test results are as follows in table 3:
TABLE 3 test results of luminescence characteristics (luminance value of 6000nits)
Examples 33 to 48
The organic electroluminescent devices of examples 33 to 48 were fabricated according to the above-described fabrication method of organic electroluminescent devices, and HT-1, HT-4, HT-8, HT-9, HT-10, HT-11, HT-12, HT-17, HT-20, HT-24, HT-29, HT-31, HT-36, HT-38, HT-40, and HT-44, which are compounds shown in Table 1, were used as host materials to form the second hole transport layer.
Comparative examples 51 to 59
The organic electroluminescent device was prepared according to the above-described method for preparing an organic electroluminescent device, using the compound RH-44 shown in table 1 as a host material, and the comparative compound 1 to the comparative compound 9 for forming a second hole transport layer.
Comparative examples 60 to 75
An organic electroluminescent device was prepared according to the above method for preparing an organic electroluminescent device, using comparative compound 12 shown in Table 1 for the host material, and HT-1, HT-4, HT-8, HT-9, HT-10, HT-11, HT-12, HT-17, HT-20, HT-24, HT-29, HT-31, HT-36, HT-38, HT-40, and HT-44 for forming the second hole transport layer.
The organic electroluminescent devices obtained in the above device examples 33 to 48 and device comparative examples 51 to 75 were characterized at a luminance of 6000(nits) for driving voltage, luminous efficiency, and lifetime, and the test results are shown in the following table 4:
TABLE 4 test results of luminescence characteristics (luminance value of 6000nits)
Examples 49 to 64
The organic electroluminescent devices of examples 49 to 64 were prepared according to the above-described method of preparing organic electroluminescent devices, and the compounds RH-60 shown in Table 1 were used as host materials, and HT-1, HT-4, HT-8, HT-9, HT-10, HT-11, HT-12, HT-17, HT-20, HT-24, HT-29, HT-31, HT-36, HT-38, HT-40, and HT-44 were used to form the second hole transporting layer.
Comparative examples 76 to 84
The organic electroluminescent device was prepared according to the above-described method for preparing an organic electroluminescent device, using the compound RH-60 shown in table 1 as a host material, and comparative compound 1 to comparative compound 9 for forming a second hole transport layer.
Comparative examples 85 to 100
An organic electroluminescent device was prepared according to the above-described method for preparing an organic electroluminescent device, using comparative compound 13 shown in Table 1 for the host material, and HT-1, HT-4, HT-8, HT-9, HT-10, HT-11, HT-12, HT-17, HT-20, HT-24, HT-29, HT-31, HT-36, HT-38, HT-40, and HT-44 for forming the second hole transport layer.
The organic electroluminescent devices obtained in the above device examples 49 to 64 and device comparative examples 76 to 100 were characterized for driving voltage, luminous efficiency, and lifetime at 6000(nits) luminance, and the test results are shown in the following table 5:
TABLE 5 test results of luminescence characteristics (luminance value of 6000nits)
Examples 65 to 80
The organic electroluminescent devices of examples 65 to 80 were fabricated according to the above-described fabrication methods of organic electroluminescent devices, and HT-1, HT-4, HT-8, HT-9, HT-10, HT-11, HT-12, HT-17, HT-20, HT-24, HT-29, HT-31, HT-36, HT-38, HT-40, and HT-44, which are compounds shown in Table 1, were used to form the second hole transport layer, using the compounds RH-78 as host materials.
Comparative examples 101-109
The organic electroluminescent device was prepared according to the above-described method for preparing an organic electroluminescent device, using the compound RH-78 shown in table 1 as a host material, and comparative compound 1 to comparative compound 9 for forming a second hole transport layer.
Comparative example 110-
The organic electroluminescent device was prepared according to the above-described method for preparing an organic electroluminescent device, using comparative compound 14 shown in Table 1 for the host material, and HT-1, HT-4, HT-8, HT-9, HT-10, HT-11, HT-12, HT-17, HT-20, HT-24, HT-29, HT-31, HT-36, HT-38, HT-40, and HT-44 for forming the second hole transport layer.
The organic electroluminescent devices obtained in the device examples 65 to 80 and the device comparative example 101-125 were characterized at 6000(nits) luminance for driving voltage, luminous efficiency, and lifetime, and the test results are shown in the following table 6:
TABLE 6 test results of luminescence characteristics (luminance value of 6000nits)
As can be illustrated from the above tables 2 to 6, examples 1 to 80 exhibited lower driving voltage, higher luminous efficiency, and/or longer life than comparative examples by using the fused azulene derivative compound represented by formula II that forms the light emitting layer and the compound represented by formula I that forms the second hole transporting layer.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and various modifications and changes may be made to the present invention by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. An organic electroluminescent composition comprising an arylamine derivative represented by the formula I for forming a hole transport region and a condensed azulene derivative represented by the formula II for forming a light-emitting layer,
R′1-R′3each independently selected from any one of the functional groups formed by hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted 3-to 18-membered heteroaryl, substituted or unsubstituted C3-C12 cycloalkyl and substituted or unsubstituted C1-C6 alkoxy; r'4Any one selected from hydrogen, methyl, ethyl, isopropyl and phenyl; or R'1-R′4Form a condensed ring with the benzene ring and/or the adjacent ring;
ar is any one of functional groups formed by hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted 3-to 30-membered heteroaryl;
R1-R4each independently selected from any one of the group of functional groups consisting of hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C24 aryl, and substituted or unsubstituted 3-to 24-membered heteroaryl; or R1-R4Form a condensed ring with the benzene ring and/or the adjacent ring.
2. The organic electroluminescent composition according to claim 1, wherein the compound represented by formula I is selected from any one of the following compounds represented by the following structural formula:
preferably, the arylamine derivative represented by formula I is used to form the second hole transport layer of the hole transport region.
3. The organic electroluminescent composition according to claim 1 or 2, wherein Ar is Ar1And Ar2Independently selected from any one of the following groups of functional groups:
4. organic electroluminescent composition according to claim 1 or 2, characterized in that R'1-R′3Selected from hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridylAny one of functional groups formed by methoxyl, phenanthryl, dibenzofuryl, dimethylfluorenyl and furyl;
preferably, R'1-R′2Any one of functional groups selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, methoxy, phenanthryl, dibenzofuranyl, and dimethylfluorenyl;
R′3and the functional group is any one of deuterium, methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, methoxy, phenanthryl, dimethylfluorenyl and furyl.
5. The organic electroluminescent composition according to claim 1, wherein the compound represented by formula I is selected from any one of the following compounds represented by the following structural formulas:
6. the organic electroluminescent composition according to claim 1, wherein the compound represented by formula II is selected from any one of the following compounds represented by the following structural formula:
7. the organic electroluminescent composition according to claim 1 or 6, wherein L is independently any one selected from the group consisting of a linking bond, biphenyl, pyrimidinyl, triazinyl, and a functional group formed by the following groups; ar is independently selected from any one of hydrogen, deuterium, methyl, pyrimidyl, triazinyl and a functional group formed by the following groups;
preferably, R5-R6And any one of functional groups formed by hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, pyrimidyl, triazinyl and methoxy.
8. The organic electroluminescent composition according to claim 1 or 6, wherein R is1-R4Each independently selected from any one of the functional groups formed by hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, pyrimidyl, triazinyl and methoxy.
9. The organic electroluminescent composition according to claim 1, wherein the compound represented by formula II is selected from any one of the following compounds represented by the following structural formula:
10. an organic electroluminescent device comprising a hole transport region formed from an arylamine derivative represented by formula i and a light-emitting layer formed from a fused azulene derivative represented by formula II, wherein the hole transport region is connected to the light-emitting layer.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114975839A (en) * | 2022-07-26 | 2022-08-30 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent device, organic electroluminescent device and photoelectric equipment |
| CN115295745A (en) * | 2022-07-12 | 2022-11-04 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent device and display equipment |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110268542A (en) * | 2017-02-28 | 2019-09-20 | 罗门哈斯电子材料韩国有限公司 | Organnic electroluminescent device |
| CN111440156A (en) * | 2020-05-07 | 2020-07-24 | 吉林奥来德光电材料股份有限公司 | Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device |
| WO2020226298A1 (en) * | 2019-05-03 | 2020-11-12 | 덕산네오룩스 주식회사 | Organic electronic element including compound for organic electronic element, and electronic device therefor |
| CN112375002A (en) * | 2021-01-18 | 2021-02-19 | 苏州久显新材料有限公司 | 2,4, 7-trisubstituted fluorene compound and electronic device thereof |
| CN113264871A (en) * | 2021-04-23 | 2021-08-17 | 烟台显华化工科技有限公司 | Compound, electron transport material and organic electroluminescent device |
| CN113493422A (en) * | 2020-03-20 | 2021-10-12 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compound, organic electroluminescent material comprising same, and organic electroluminescent device |
| CN113816898A (en) * | 2021-03-29 | 2021-12-21 | 烟台显华化工科技有限公司 | Compound, electron transport material, organic electroluminescent device and display device |
-
2022
- 2022-01-13 CN CN202210038734.3A patent/CN114430010B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110268542A (en) * | 2017-02-28 | 2019-09-20 | 罗门哈斯电子材料韩国有限公司 | Organnic electroluminescent device |
| WO2020226298A1 (en) * | 2019-05-03 | 2020-11-12 | 덕산네오룩스 주식회사 | Organic electronic element including compound for organic electronic element, and electronic device therefor |
| CN113493422A (en) * | 2020-03-20 | 2021-10-12 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compound, organic electroluminescent material comprising same, and organic electroluminescent device |
| CN111440156A (en) * | 2020-05-07 | 2020-07-24 | 吉林奥来德光电材料股份有限公司 | Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device |
| CN112375002A (en) * | 2021-01-18 | 2021-02-19 | 苏州久显新材料有限公司 | 2,4, 7-trisubstituted fluorene compound and electronic device thereof |
| CN113816898A (en) * | 2021-03-29 | 2021-12-21 | 烟台显华化工科技有限公司 | Compound, electron transport material, organic electroluminescent device and display device |
| CN113264871A (en) * | 2021-04-23 | 2021-08-17 | 烟台显华化工科技有限公司 | Compound, electron transport material and organic electroluminescent device |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115295745A (en) * | 2022-07-12 | 2022-11-04 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent device and display equipment |
| CN114975839A (en) * | 2022-07-26 | 2022-08-30 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent device, organic electroluminescent device and photoelectric equipment |
| CN114975839B (en) * | 2022-07-26 | 2022-10-28 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent device, organic electroluminescent device and photoelectric equipment |
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