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CN108164564A - A kind of metal iridium complex and the organic electroluminescence device comprising the metal iridium complex - Google Patents

A kind of metal iridium complex and the organic electroluminescence device comprising the metal iridium complex Download PDF

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CN108164564A
CN108164564A CN201810134626.XA CN201810134626A CN108164564A CN 108164564 A CN108164564 A CN 108164564A CN 201810134626 A CN201810134626 A CN 201810134626A CN 108164564 A CN108164564 A CN 108164564A
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layer
thickness
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曹建华
隋岩
董梁
张建川
王士波
唐永顺
华瑞茂
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Priority to PCT/CN2019/073489 priority patent/WO2019154159A1/en
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    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
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    • H10K50/00—Organic light-emitting devices
    • 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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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
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  • Electroluminescent Light Sources (AREA)

Abstract

A kind of organic electroluminescence device the invention discloses metal iridium complex and comprising the metal iridium complex, the general structure of the metal iridium complex is shown in formula I.Metal iridium complex electroluminescent proposed by the present invention is green to red, and luminous efficiency is high, while the thermal stability of material is good, and material is easily prepared, is easily purified, and is the ideal chose as organic electroluminescence device luminescent material.

Description

Metal iridium complex and organic electroluminescent device containing same
Technical Field
The invention relates to the technical field of organic light-emitting diodes. And more particularly, to a metal iridium complex and an organic electroluminescent device including the same.
Background
Organic electroluminescence (abbreviated as OLED) and related research firstly discovered the electroluminescence phenomenon of organic compound single crystal anthracene in pope et al as early as 1963. Kodak company of the United states of 1987 made an amorphous film device by evaporating small organic molecules, and reduced the driving voltage to within 20V. The device has the advantages of ultra-light weight, full curing, self luminescence, high brightness, wide viewing angle, fast response speed, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristic, soft display realization and the like, and can be widely applied to flat panel displays and surface light sources, thereby being widely researched, developed and used.
Organic electroluminescent materials fall into two broad categories: organic electroluminescent materials and organic electrophosphorescent materials, in which organic electroluminescence is a result of radiative deactivation of singlet excitons, unlike photoluminescence, during which triplet excitons and singlet excitons are simultaneously generated. The generation ratio of singlet excitons and triplet excitons is generally 1: and 3, according to forbidden blocking effect of quantum statistics, triplet excitons mainly undergo non-radiative decay, have little contribution to luminescence, and only singlet excitons emit luminescence by radiation, so that the fundamental reason that the luminescence efficiency is difficult to improve for the organic/polymer electroluminescent device is that the luminescence process is the luminescence of singlet excitons.
In the early stage of organic light emitting device research, people put forward the assumption of triplet state luminescence, and the Forrest group made red electrophosphorescent light emitting devices by doping octaethylporphyrin platinum in a small molecular host material of octahydroxyquinoline aluminum, so that the external quantum efficiency reaches 4%, so far, the research of electrophosphorescence started to get great attention from academia, and the research of organic electrophosphorescence in the following years is rapidly developed. The iridium complex is a phosphorescent material which is developed most and has the best application prospect due to the short triplet state service life and the good luminescent performance, and the phosphorescent material has stronger triplet state quenching in a solid, so that generally the iridium complex is used as a doping object material, a material with a wider band gap is used as a doping host material, and high luminescent efficiency is obtained by energy transfer or direct exciton trapping on an object for luminescence.
Organic electroluminescent green phosphorescent materials are the earliest studied and the most mature materials. Hino et al in 2004 made phosphorescent devices by spin coating, the external quantum efficiency was at most 29cd/A, and the high efficiency achieved by this simple device structure was attributable to the good film-forming properties of the material and the energy transfer from host to guest material. Adachi et al doped (ppy)2Ir (acac) into TAZ and HMTPD as hole transport layer, obtained a green device with maximum external quantum efficiency of 20% and energy efficiency of 65lm/W, calculated that its internal quantum efficiency almost approached 100%, and triplet excitons and singlet excitons were simultaneously utilized.
In terms of light emission color, compared with phosphorescent materials of other colors, the development of blue electrophosphorescent materials is not only the latest but also the least desirable, and is still a very challenging subject. The mechanism research shows that as the triplet state energy level is increased, not only the rate of radiative transition is increased, but also the rate of non-radiative transition is increased, and the increasing amplitude of the latter is more obvious, and the total effect is rather to reduce the luminous efficiency, which leads to that the blue shift and the high efficiency of the luminous wavelength in the research of blue light materials are difficult to be simultaneously realized, and often the blue shift and the high efficiency are thin. Therefore, no blue phosphorescent material with excellent comprehensive performance has been reported so far.
Disclosure of Invention
In order to solve the above technical problems, the present invention provides a metal iridium complex emitting light in a green to red color with high luminous efficiency and an organic electroluminescent device including the same.
The invention specifically provides a metal iridium complex shown as a formula I:
wherein:
R1and R2Each independently represents C1-C10 alkyl, C4-C10 cycloalkyl, deuterium substituted C1-C10 alkyl, deuterium substituted C4-C10 cycloalkyl, C1-C8 alkoxy, deuterium substituted C1-C8 alkoxy, C1-C8 alkylthio, deuterium substituted C1-C8 alkylthio, fluorine or cyano;
R3、R4、R5each independently represents hydrogen, deuterohydrogen, fluorine, C1-C8 alkyl, deuterium substituted C1-C8 alkyl, C1-C8 alkoxy, deuterium substituted C1-C8 alkoxy, C1-C8 silyl, substituted or unsubstituted C1-C8 alkyl6-C20Aryl, substituted or notSubstituted C6-C20Aryloxy, substituted or unsubstituted C6-C20Arylthio, fluoro or cyano;
said substituted C6-C20Aryl, substituted C6-C20Aryloxy and substituted C6-C20The substituents in the arylthio group are each independently selected from hydrogen, deuterohydrogen, halogen atom, hydroxyl, cyano, C1-C20Alkyl radical, C2-C20Alkenyl radical, C2-C20Alkynyl, C1-C20Alkoxy radical, C3-C20Cycloalkyl or C3-C20One or more kinds of cyclic olefin groups;
a represents C or N;
x represents O, S or Se;
each n independently represents 1, 2 or 3.
Preferably, the structural formula of the compound with the structural formula I is specifically shown as II and III, but not limited to the following structures:
wherein,
R1、R2、R3、R4、R5x and n are independently of R in formula I1、R2、R3、R4、R5X and n are the same.
Further preferably, the structural formula of the compound of formula II is specifically as shown in formulas II-01 to II-54 below, but not limited to the following structures:
further preferably, the structural formula of the compound of formula III is specifically as shown in formulas III-01 to III-51 below, but not limited to the following structures:
the invention also provides an organic electroluminescent device, which comprises a substrate, an anode layer arranged on the substrate, a hole transport layer arranged on the anode layer, an organic luminescent layer arranged on the hole transport layer, an electron transport layer arranged on the organic luminescent layer and a cathode layer arranged on the electron transport layer; wherein the material of the organic light-emitting layer comprises one or more of the metal complexes.
Preferably, a hole injection layer is further arranged between the anode layer and the hole transport layer in the organic electroluminescent device.
The substrate can be glass or a flexible substrate, and the flexible substrate is made of one of polyester and polyimide compounds;
preferably, the anode layer can be made of inorganic materials or organic conducting polymers, the inorganic materials are metal oxides such as Indium Tin Oxide (ITO), zinc oxide, tin zinc oxide and the like or metals with high functional functions such as gold, silver, copper and the like, the ITO is selected optimally, and the organic conducting polymers are preferably one of polythiophene/sodium polyvinylbenzene sulfonate (PEDOT: PSS) and polyaniline;
preferably, the cathode layer is an electrode layer formed by using metals with lower functional functions such as lithium, magnesium, silver, calcium, strontium, aluminum, indium and the like or alloys of the metals with copper, gold and silver or metal and metal fluoride alternately, and the invention is preferably a magnesium/silver alloy layer;
preferably, the hole transport layer and the hole injection layer can both adopt triarylamine materials, preferably NPB or DNTPD, and the structural formula is as follows:
preferably, the electron transport layer is generally a metal organic complex, preferably Alq3, Liq, BPhen, etc., having the formula:
preferably, the organic light emitting layer can generally adopt a small molecule material, and can be doped with a fluorescent material or a phosphorescent dye, the material of the organic light emitting layer of the present invention includes the metal complex proposed by the present invention, the metal complex can be used as a phosphorescent doped material to emit light in a corresponding host material, and the preferred host material is selected from one or more of the following compounds:
preferably, the preparation method of the organic electroluminescent device comprises the following steps:
1) cleaning a glass substrate with ITO by using a cleaning agent, deionized water and an organic solvent in several steps;
2) evaporating a hole injection layer containing the material of the invention by a vacuum evaporation method;
3) evaporating a hole transport layer of the device by a vacuum evaporation method;
4) then, continuously evaporating a luminescent layer containing the material of the invention;
5) continuously evaporating an electron transport layer containing the material of the invention;
6) and preparing the metal cathode by a method of evaporation plating, sputtering or spin coating.
Preferably, the hole injection layer has a thickness of 30 to 50nm, more preferably a hole injection layer thickness of 40nm,
preferably, the thickness of the hole transport layer is 5 to 15nm, and more preferably, the thickness of the hole transport layer is 10 nm.
Preferably, the thickness of the organic light emitting layer is 10 to 100nm, and more preferably, the thickness of the organic light emitting layer is 50 nm.
Preferably, the thickness of the electron transport layer is 10 to 30nm, and more preferably, the thickness of the electron transport layer is 20 nm.
Preferably, the thickness of the cathode layer is 90-110nm, more preferably the thickness of the cathode layer is 100 nm.
The invention also provides an organic electroluminescent material, and the raw material of the organic electroluminescent material comprises one or more of the metal complexes.
The invention also provides application of the metal complex in preparing an organic electroluminescent device.
The invention also provides application of the metal complex in preparing organic electroluminescent materials.
The use of the metal complexes of the invention as luminescent materials alone or as host materials or doping materials in the luminescent layer is also within the scope of protection.
Unless otherwise specified, all starting materials for use in the present invention are commercially available and any range recited herein includes any endpoints and any numerical values therebetween and any subranges therebetween.
The invention has the following beneficial effects:
the metal iridium complex provided by the invention is a series of pyridine metal complex electrophosphorescent luminescent materials with benzo heterocyclic structures, and is a series of phosphorescent materials prepared by taking modified benzofuran or benzothiophene as a raw material and modifying the modified benzofuran or benzothiophene with substituted 2-pyridyl; the metal complex involved in the invention has green to red electroluminescence, high luminous efficiency and good thermal stability, and the material is easy to prepare, sublimate and purify and has very wide market prospect.
Drawings
Fig. 1 is a schematic structural diagram of an OLED device in embodiment 10 of the present invention.
Detailed Description
In order to more clearly illustrate the invention, the invention is further described below with reference to preferred embodiments and the accompanying drawings. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
The following describes embodiments of the present invention in further detail with reference to the accompanying drawings.
Fig. 1 is a schematic structural diagram of an OLED device in embodiment 10 of the present invention. The organic electroluminescent device comprises a substrate 1, an anode layer 2, a hole injection layer 3, a hole transport layer 4, an organic light emitting layer 5, an electron transport layer 6 and a cathode layer 7.
In the present invention, the preparation methods are all conventional methods unless otherwise specified. The starting materials used are available from published commercial sources unless otherwise specified, and the percentages are by mass unless otherwise specified. The series of novel metal complexes provided by the present invention, all reactions being carried out under well-known suitable conditions, some involving simple organic preparations, for example the preparation of phenylboronic acid derivatives, can be synthesized by skilled operative skills and are not described in detail herein.
The synthetic route for the compounds of formula II of the present invention, represented by structural formula I, is shown below, and it will be understood by those skilled in the art that similar routes may also be used for the synthesis of other compounds.
The synthetic route for the compounds of formula III of the present invention, represented by structural formula I, is shown below, and it will be understood by those skilled in the art that similar routes may also be used for the synthesis of other compounds.
The reaction route gives an example of a synthetic route of a compound with a structural general formula I, and key intermediates Int-1, Int-2 and Int-3 are prepared. Wherein R is1、R2、R3、R4、R5X and n are as defined above;
the following abbreviations are used in the examples of the present invention:
TABLE 1 abbreviations and full names
Abbreviations Full scale
THF Tetrahydrofuran (THF)
n-BuLi Lithium ortho-radical
DCM Methylene dichloride
(PinB)2 Biboric acid pinacol ester
Pd(PPh3)4 Tetrakis (triphenylphosphine) palladium
DAST Diethylaminosulfur trifluoride
Example 1
Preparation of Compound II-05, the structural formula is as follows:
the preparation method of the compound II-05 comprises the following steps:
the first step is as follows: preparation of compound 3-bromo-2-hydroxybenzaldehyde
14.5g of anhydrous magnesium chloride is dispersed in 250ml of anhydrous tetrahydrofuran, 7.5g of paraformaldehyde and 21ml of triethylamine are added, after stirring reaction is carried out for 30 minutes, 17.5g of o-bromophenol is added, after the addition is finished, stirring and heating reflux reaction are carried out for 16 hours, cooling to room temperature is carried out, 500ml of dilute hydrochloric acid is added, extraction is carried out by ethyl acetate, an organic phase is dried by anhydrous sodium sulfate, filtration, decompression, concentration and drying are carried out, and separation and purification are carried out by a silica gel column, so that 30g of yellow oily matter is obtained.
The second step is that: preparation of compound 7-bromo-2-nitrobenzofuran
Dissolving 20g of the oily substance obtained in the first step by using 250ml of acetone, adding 28g of anhydrous potassium carbonate under the protection of nitrogen, cooling to 10 ℃ by using an ice water bath, adding 28g of bromonitromethane, keeping the temperature, stirring, reacting for 2 hours, filtering, concentrating the filtrate under reduced pressure, adding 10ml of concentrated hydrochloric acid and 200ml of methanol, heating, refluxing, reacting for 30 minutes, cooling to room temperature, filtering, and washing the filter cake by using methanol to obtain 18.5g of yellow solid.
The third step: preparation of compound 7-bromo-2-aminobenzofuran
Dissolving 18g of the product of the second step, namely 7-bromo-2-nitrobenzofuran, by using 100ml of ethanol and 100ml of tetrahydrofuran, adding 10ml of water and 36g of ammonium chloride, adding 20g of iron powder under stirring at room temperature, stirring for reacting for 16 hours, filtering, concentrating the filtrate under reduced pressure to dryness, and purifying the residue by using an acid-base method to obtain 11g of yellow solid.
The fourth step: preparation of Compound int. -1
600ml of glacial acetic acid and 20ml of water are added into a reaction bottle, the reaction bottle is heated to reflux, 10g of 7-bromo-2-aminobenzofuran and 18.2g of trifluoroacetylacetone are slowly added dropwise while stirring, dissolved in 100ml of dry DMF solution, and after the dropwise addition, the reflux reaction is carried out for 3 hours, the mixture is cooled to room temperature, and the mixture is concentrated under reduced pressure and dried, and is separated and purified by a silica gel column to obtain 13g of Int-1, white solid.
The fifth step: preparation of Compound Int-2
Mixing 10.0g of the compound Int-1 obtained in the fourth step, 8.5g of triisopropyl borate and 200ml of dry tetrahydrofuran, cooling to-78 ℃ by using liquid nitrogen under the protection of nitrogen, slowly dropwise adding 14.5ml of a 2.5M n-butyllithium-hexane solution, keeping the temperature for reacting for 1 hour, raising the temperature to room temperature, stirring for reacting for 30 minutes, dropwise adding 100ml of dilute hydrochloric acid, stirring for reacting for 30 minutes, separating an organic phase, extracting an aqueous phase by using ethyl acetate, drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, dispersing the residue by using petroleum ether, and filtering to obtain 7.3g of Int-2, white solid.
And a sixth step: preparation of Compound Int-3
5.5g of the intermediate Int-2 obtained in the fifth step, 4.4g of 2-bromopyridine, 8.0g of anhydrous sodium carbonate, 50ml of toluene, 20ml of ethanol and 20ml of water are mixed, 40mg of catalyst Pd (PPh3)4 is added, the mixture is heated under reflux for 12 hours under the protection of nitrogen, the mixture is cooled to room temperature, an organic phase is separated, the aqueous phase is extracted by ethyl acetate, the organic phase is dried and filtered, the filtrate is concentrated under reduced pressure to be dry, and the residue is separated and purified by a silica gel column to obtain 5.0g of Int-3 as a yellow solid.
The seventh step: preparation of Compound II-05
5.0g of the compound Int-3 of the sixth step and 3.6g of the iridium chelate SM-10 are dispersed in 120ml of ethylene glycol ethyl ether and 120ml of dry DMF, and under the protection of nitrogen, the mixture is heated to 135 ℃ and stirred for reaction for 24 hours, cooled to room temperature, and then the solvent is removed by concentration under reduced pressure, and the mixture is separated and purified by a silica gel column to obtain 2.7g of a compound II-05, a yellow solid, TOF-MS: m/z (%). 829.1676[ M++1]The correctness of Compound II-05 was confirmed.
Example 2
Preparation of Compound II-23, the structural formula is as follows:
preparation of the above compound II-23, intermediate int. -4 was prepared according to the preparation method of the first to sixth steps in example 1, and the preparation method of other compounds included the following steps:
the first step is as follows: preparation of Compound int. -5
6.0g of intermediate int. -4 is dispersed in 150ml of deuterated ethanol, 2.5g of sodium ethoxide solid is added, the mixture is stirred, heated and refluxed for 3 days, cooled to room temperature, decompressed and concentrated to dryness, 150ml of ice water and 150ml of ethyl acetate are added, an organic phase is separated, an aqueous phase is extracted by ethyl acetate, dried and filtered, a filtrate is decompressed and concentrated to dryness, and the mixture is separated and purified by a silica gel column to obtain 5.0g of white solid.
The second step is that: preparation of Compound II-23
5.0g of the first-step compound int. -5 and 3.4g of iridium chelate SM-10 were dispersed in 120ml of ethylene glycol ethyl ether and 120ml of dry DMF, and the mixture was heated to 135 ℃ under nitrogen protection, stirred and reacted for 24 hours, cooled to room temperature, and concentrated under reduced pressure to remove the solvent, and subjected to silica gel column separation and purification to obtain 2.0g of compound II-23, a yellow solid, TOF-MS: m/z (%). 841.3182[ M++1]Thus, it was confirmed that Compound II-23 was correct.
Example 3
Preparation of compound II-26, structural formula:
preparation of the above-mentioned compound II-26, intermediate int. -6 was prepared according to the preparation method of the first step to the sixth step in example 1, and the preparation method of other compounds included the following steps:
the first step is as follows: preparation of Compound int. -7
Dispersing 10.0g of the intermediate int. -6 in 150ml of deuterated ethanol, adding 3.5g of sodium ethoxide solid, stirring, heating, refluxing for 5 days, cooling to room temperature, concentrating under reduced pressure to dryness, adding 150ml of ice water and 150ml of ethyl acetate, separating an organic phase, extracting an aqueous phase with ethyl acetate, drying, filtering, concentrating a filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain 7.5g of white solid.
The second step is that: preparation of Compound II-26
5.0g of the first-step compound int. -7 and 2.7g of iridium chelate SM-10 were dispersed in 120ml of ethylene glycol ethyl ether and 120ml of dry DMF, and the mixture was heated to 135 ℃ under nitrogen protection, stirred and reacted for 24 hours, cooled to room temperature, and concentrated under reduced pressure to remove the solvent, and subjected to silica gel column separation and purification to obtain 2.4g of compound II-26, a yellow solid, TOF-MS: m/z (%). 933.4588[ M++1]The correctness of Compound II-26 was confirmed.
Example 4
Preparation of Compound II-51, the structural formula is as follows:
the preparation method of the compound II-51 comprises the following steps:
the first step is as follows: preparation of Compound int. -8
Adding 300ml of glacial acetic acid and 10ml of water into a reaction bottle, heating to reflux, slowly dropwise adding 5.0g of 7-bromo-2-aminobenzofuran and 11.0g of 2-tetrahydrofuryl acetone under stirring, dissolving in 50ml of dry DMF solution, after dropwise adding, refluxing for 3 hours, cooling to room temperature, concentrating under reduced pressure, and separating and purifying by using a silica gel column to obtain 7.5g of int. -8 white solid.
The second step is that: preparation of compound int
Dissolving 7.0g of the compound Int. -8 obtained in the first step in 120ml of dry tetrahydrofuran, cooling to-78 ℃ by using liquid nitrogen under the protection of nitrogen, slowly dropwise adding 10ml of 2.5M n-butyllithium-hexane solution, keeping the temperature for reaction for 30 minutes, dropwise adding 6.0g of triisopropyl borate, heating to room temperature, stirring for reaction for 1 hour, dropwise adding 100ml of dilute hydrochloric acid, stirring for reaction for 30 minutes, separating out an organic phase, extracting an aqueous phase by using ethyl acetate, drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, dispersing the residue by using petroleum ether, and filtering to obtain 4.5g of Int. -9 as a white solid.
The third step: preparation of Compound int. -10
Preparation of compound int. -10 referring to the sixth step of example 1, compound int. -10 was prepared as a white solid by replacing intermediate int. -2 of the sixth step of example 1 with product int. -9 of the second step of this example.
The fourth step: preparation of Compound II-51
5.0g of the third step compound Int. -10 and 3.6g of iridium chelate SM-10 are dispersed in 120ml of ethylene glycol ethyl ether and 120ml of dry DMF, the mixture is heated to 135 ℃ under the protection of nitrogen, stirred and reacted for 24 hours, cooled to room temperature, decompressed and concentrated to remove the solvent, and separated and purified by a silica gel column to obtain 3.5g of compound II-51, a yellow solid, TOF-MS: m/z (%). 831.2217[ M++1]The compound II-51 was confirmed to be correct.
Example 5
Preparation of Compound II-52, the structural formula is as follows:
preparation of the above compound II-52, intermediate int. -10 was prepared according to the preparation method of the first to third steps in example 4, and the preparation method of the other compound included the following steps:
the first step is as follows: preparation of compound int. -11
Dispersing 10.0g of the intermediate int. -10 in 150ml of deuterated ethanol and 10ml of deuterated tetrahydrofuran, adding 4.5g of sodium ethoxide solid, stirring, heating, refluxing for 5 days, cooling to room temperature, concentrating under reduced pressure to dryness, adding 150ml of ice water and 150ml of ethyl acetate, separating an organic phase, extracting an aqueous phase with ethyl acetate, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain 9.5g of white solid.
The second step is that: preparation of Compound II-52
5.0g of the first-step compound int. -11 and 3.5g of iridium chelate SM-10 were dispersed in 120ml of ethylene glycol ethyl ether and 120ml of dry DMF, and the mixture was heated to 135 ℃ under nitrogen protection, stirred and reacted for 24 hours, cooled to room temperature, and concentrated under reduced pressure to remove the solvent, and subjected to silica gel column separation and purification to obtain 3.0g of compound II-52, a yellow solid, TOF-MS: m/z (%). 840.2845[ M+]Confirmation of Compound II-52 nAnd (8) determining.
Example 6
Preparation of Compound III-01, the structural formula is as follows:
the preparation method of the compound III-01 comprises the following steps:
the first step is as follows: preparation of Compound int. -12
10.0g of the compound SM-20 (prepared by the method described in Chemistry-A European Journal,2016,22(30), P10415) was dispersed in 250ml of ethanol, and 4.5g of acetamidine hydrochloride and 10.0g of potassium hydroxide were added thereto, and the mixture was stirred at an elevated temperature under reflux for 2 hours, cooled to room temperature, concentrated to dryness under reduced pressure, and 150ml of ice water was added thereto, followed by filtration, washing of the cake with water, drying, and separation and purification with a silica gel column to obtain 7.3g of a yellow solid.
The second step is that: preparation of compound int. -13
Preparation of compound int. -13 referring to the second step of example 4, intermediate int. -8 of the second step of example 4 was replaced with product int. -12 of the first step of this example to prepare compound int. -13 as a white solid.
The third step: preparation of compound int. -14
Preparation of compound int. -14 referring to the third step of example 4, compound int. -14 was prepared as a yellow solid by replacing intermediate int. -9 of the third step of example 4 with product int. -13 of the second step of this example.
The fourth step: preparation of Compound III-01
5.0g of the third compound int. -14 and 4.3g of the iridium chelate SM-10 are dispersed in 120ml of ethylene glycol ethyl ether and 120ml of dry DMF, the mixture is heated to 135 ℃ under the protection of nitrogen, stirred and reacted for 24 hours, cooled to room temperature, and then the solvent is removed by concentration under reduced pressure, and the mixture is separated and purified by a silica gel column to obtain 3.7g of compound III-01, a yellow solid, TOF-MS: m/z (%). 776.1918[ M++1]Thus, it was confirmed that Compound III-01 was correct.
Example 7
Preparation of Compound III-18, the structural formula is as follows:
the first step is as follows: preparation of Compound int. -15
10.0g of the compound SM-30 (prepared by the method described in chemical-A European Journal,2016,22(30), P10415) was dispersed in 250ml of ethanol, and 4.9g of isopropyl formamidine hydrochloride and 8.8g of potassium hydroxide were added thereto, and the mixture was stirred, heated under reflux for 2 hours, cooled to room temperature, concentrated to dryness under reduced pressure, and 150ml of ice water was added thereto, followed by filtration, washing of the cake with water, drying, and separation and purification with a silica gel column to obtain 8.2g of a yellow solid.
The second step is that: preparation of Compound int. -16
Preparation of compound int. -16 referring to the second step of example 4, intermediate int. -8 of the second step of example 4 was replaced with product int. -15 of the first step of this example to prepare compound int. -16 as a yellow solid.
The third step: preparation of compound int. -17
Preparation of compound int. -17 referring to the third step of example 4, compound int. -17 was prepared as a yellow solid by replacing intermediate int. -9 of the third step of example 4 with product int. -16 of the second step of this example.
The fourth step: preparation of Compound III-18
5.0g of the third compound int. -16 and 3.3g of the iridium chelate SM-10 are dispersed in 120ml of ethylene glycol ethyl ether and 120ml of dry DMF, the mixture is heated to 135 ℃ under the protection of nitrogen, stirred and reacted for 24 hours, cooled to room temperature, and then the solvent is removed by concentration under reduced pressure, and the mixture is separated and purified by a silica gel column to obtain 2.5g of compound III-18, a yellow solid, TOF-MS: m/z (%). 858.2692[ M++1]The correctness of Compound III-18 was confirmed.
Example 8
Preparation of Compound III-12, the structural formula is as follows:
the preparation method of the compound III-12 comprises the following steps:
the first step is as follows: preparation of Compound Int-18
10.0g of compound SM-20 and 100g of urea are mixed, stirred, heated to reflux, stirred and reacted for 2 hours, cooled to 100 ℃, and added dropwise with 10% sodium hydroxide aqueous solution, stirred to room temperature, added dropwise with dilute hydrochloric acid for neutralization, filtered, washed with water, dried and recrystallized by ethanol to obtain 8.2g of compound Int-18, a white solid.
The second step is that: preparation of Compound Int-19
8.0g of compound Int-18 and 48ml of DAST are mixed, heated to 40 ℃ under the protection of nitrogen, stirred and reacted for 24 hours, cooled to room temperature, concentrated under reduced pressure, dried, added with 100ml of ice water, filtered, washed by water, dried in vacuum, and separated and purified by a silica gel column to obtain 7.6g of compound Int-19 as a yellow solid.
The third step: preparation of Compound int. -20
Preparation of compound int. -20 referring to the fifth step of example 1, compound int. -20 was prepared as a yellow solid by replacing intermediate int. -1 of the fifth step of example 1 with product int. -19 of the second step of this example.
The fourth step: preparation of compound int. -21
Preparation of compound int. -21 referring to the third step of example 4, compound int. -21 was prepared as a yellow solid by replacing intermediate int. -9 of the third step of example 4 with product int. -20 of the third step of this example.
The fifth step: preparation of Compound III-12
5.0g of the compound int. -21 of the fourth step and 4.2g of the iridium chelate SM-10 are dispersed in 120ml of ethylene glycol ethyl ether and 120ml of dry DMF, the mixture is heated to 135 ℃ under the protection of nitrogen, stirred and reacted for 24 hours, cooled to room temperature, and then the solvent is removed by concentration under reduced pressure, and the mixture is separated and purified by a silica gel column to obtain 3.3g of a compound III-12, a yellow solid, TOF-MS: m/z (%). 780.1665[ M++1]The correctness of Compound III-12 was confirmed.
Example 9
Preparation of compound III-39, the structural formula is as follows:
preparation of the above-mentioned compound III-39, intermediate int. -22 was prepared according to the preparation method of the first to third steps in example 6, and the preparation method of the other compound included the following steps:
the first step is as follows: preparation of compound int. -23
Dispersing 10.0g of the intermediate int. -22 in 150ml of deuterated ethanol, adding 4.0g of sodium ethoxide solid, stirring, heating, refluxing for 5 days, cooling to room temperature, concentrating under reduced pressure to dryness, adding 150ml of ice water and 150ml of ethyl acetate, separating an organic phase, extracting an aqueous phase with ethyl acetate, drying, filtering, concentrating a filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain 10.0g of yellow solid.
The second step is that: preparation of Compound III-39
5.0g of the first-step compound int. -23 and 3.3g of iridium chelate SM-10 were dispersed in 120ml of ethylene glycol ethyl ether and 120ml of dry DMF, and the mixture was heated to 135 ℃ under nitrogen protection, stirred and reacted for 24 hours, cooled to room temperature, and concentrated under reduced pressure to remove the solvent, and subjected to silica gel column separation and purification to obtain 2.1g of compound III-39, a yellow solid, TOF-MS: m/z (%). 858.3406[ M++1]The correctness of Compound III-39 was confirmed.
Example 10
An OLED device, as shown in fig. 1, includes a substrate 1, an anode layer 2 disposed on the substrate 1, a hole injection layer 3 disposed on the anode layer 2, a hole transport layer 4 disposed on the hole injection layer 3, an organic light emitting layer 5 disposed on the hole transport layer 4, an electron transport layer 6 disposed on the organic light emitting layer 5, and a cathode layer 7 disposed on the electron transport layer 6.
The preparation method of the OLED device comprises the following steps:
1) the glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, washed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked to be completely dry in a clean environment, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the processed ITO glass substrate in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, continuously and respectively evaporating a compound DNTPD on the anode layer film to be used as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 40 nm; continuously evaporating NPB (nitrogen-phosphorus) on the hole injection layer film to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
3) and continuously evaporating a layer of the compound formula I and the mCBP of the invention on the hole transport layer to be used as a light-emitting layer of the device, wherein the mCP is a host material and the compound formula I of the invention is a doping material, and the evaporation rate ratio of the compound formula I to the mCBP is 1: 100, the doping concentration of the compound of formula I in mCBP is 1%, the total evaporation rate is 0.1nm/s, and the thickness of the evaporation film is 50 nm;
4) continuously evaporating a layer of Liq material on the cavity to be used as an electron transport layer of the device, wherein the plating rate is 0.1nm/s, and the thickness of the evaporated film is 20 nm; finally, a magnesium/silver alloy layer is sequentially evaporated on the electron transport layer to serve as a cathode layer of the device, wherein the evaporation rate of the magnesium/silver alloy layer is 2.0-3.0 nm/s, and the evaporation film thickness is 100 nm;
according to the same steps as the above, only replacing the compound shown as the formula I used in the step 3) with a compound II-05 to obtain the OLED-1 provided by the invention;
according to the same steps as the above, only replacing the compound shown as the formula I used in the step 3) with a compound II-23 to obtain the OLED-2 provided by the invention;
according to the same steps as the above, only replacing the compound shown as the formula I used in the step 3) with a compound II-26 to obtain the OLED-3 provided by the invention;
according to the same steps as the above, only replacing the compound shown as the formula I used in the step 3) with a compound II-51 to obtain the OLED-4 provided by the invention;
according to the same steps as the above, only replacing the compound shown as the formula I used in the step 3) with a compound II-52 to obtain the OLED-5 provided by the invention;
according to the same steps as the above, only replacing the compound shown as the formula I used in the step 3) with a compound III-01 to obtain the OLED-6 provided by the invention;
according to the same steps as the above, only replacing the compound shown as the formula I used in the step 3) with a compound III-12 to obtain the OLED-7 provided by the invention;
according to the same steps as the above, only replacing the compound shown as the formula I used in the step 3) with a compound III-18 to obtain the OLED-8 provided by the invention;
according to the same steps as the above, only replacing the compound shown as the formula I used in the step 3) with a compound III-39 to obtain the OLED-9 provided by the invention;
the results of the performance tests of the obtained devices OLED-1 to OLED-9 are shown in Table 2:
TABLE 2 Performance test results
And (4) conclusion: according to the analysis of performance test results, the metal iridium complex disclosed by the invention emits green light, the color purity is good, the chromaticity coordinate is in a green light region, the performance of the metal iridium complex exceeds that of the existing known green light material, and the light-emitting service life of the device is ideal under the condition that a test device is not packaged.
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.

Claims (10)

1. The metal iridium complex is characterized in that the metal iridium complex is a compound shown as a formula I
Wherein:
R1and R2Each independently represents C1-C10 alkyl, C4-C10 cycloalkyl, deuterium substituted C1-C10 alkyl, deuterium substituted C4-C10 cycloalkyl, C1-C8 alkoxy, deuterium substituted C1-Alkoxy of C8, alkylthio of C1-C8, deuterium substituted alkylthio of C1-C8, fluoro or cyano;
R3、R4、R5each independently represents hydrogen, deuterohydrogen, fluorine, C1-C8 alkyl, deuterium substituted C1-C8 alkyl, C1-C8 alkoxy, deuterium substituted C1-C8 alkoxy, C1-C8 silyl, substituted or unsubstituted C1-C8 alkyl6-C20Aryl, substituted or unsubstituted C6-C20Aryloxy, substituted or unsubstituted C6-C20Arylthio, fluoro or cyano;
said substituted C6-C20Aryl, substituted C6-C20Aryloxy and substituted C6-C20The substituents in the arylthio group are each independently selected from hydrogen, deuterohydrogen, halogen atom, hydroxyl, cyano, C1-C20Alkyl radical, C2-C20Alkenyl radical, C2-C20Alkynyl, C1-C20Alkoxy radical, C3-C20Cycloalkyl or C3-C20One or more kinds of cyclic olefin groups;
a represents C or N;
x represents O, S or Se;
each n independently represents 1, 2 or 3.
2. The iridium complex as claimed in claim 1, wherein the compound of formula I is a compound represented by formulae II-01 to II-45 and III-01 to III-51
3. An organic electroluminescent device comprising a substrate, an anode layer, a hole transport layer, an organic light-emitting layer, an electron transport layer and a cathode layer in this order, wherein the material of the organic light-emitting layer comprises one or more metal iridium complexes as claimed in claim 1 or 2.
4. The organic electroluminescent device of claim 3, wherein a hole injection layer is further disposed between the anode layer and the hole transport layer.
5. The organic electroluminescent device according to claim 4, wherein the hole injection layer has a thickness of 30 to 50 nm.
6. The organic electroluminescent device according to claim 4, wherein the hole injection layer has a thickness of 40 nm.
7. The organic electroluminescent device according to claim 3, wherein the hole transport layer has a thickness of 5 to 15 nm; the thickness of the organic light-emitting layer is 10-100 nm; the thickness of the electron transmission layer is 10-30 nm; the thickness of the cathode layer is 90-110 nm.
8. The organic electroluminescent device according to claim 3, wherein the hole transport layer has a thickness of 10 nm; the thickness of the organic light-emitting layer is 50 nm; the thickness of the electron transport layer is 20 nm; the thickness of the cathode layer is 100 nm.
9. An organic electroluminescent material, characterized in that a raw material of the organic electroluminescent material comprises one or more of the metal iridium complexes described in claim 1 or 2.
10. Use of the iridium metal complex according to claim 1 or 2 for the preparation of organic electroluminescent devices or organic electroluminescent materials.
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Application publication date: 20180615