CN109970748A - A kind of organic luminescent compounds and preparation method thereof and device - Google Patents
A kind of organic luminescent compounds and preparation method thereof and device Download PDFInfo
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- CN109970748A CN109970748A CN201910323723.8A CN201910323723A CN109970748A CN 109970748 A CN109970748 A CN 109970748A CN 201910323723 A CN201910323723 A CN 201910323723A CN 109970748 A CN109970748 A CN 109970748A
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- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 238000002849 thermal shift Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005580 triphenylene group Chemical group 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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Abstract
The present invention relates to luminescent material technical fields, and in particular to a kind of organic luminescent compounds and preparation method thereof and device, the organic luminescent compounds structural formula as described in chemical formula 1:
Description
Technical field
The present invention relates to luminescent material technical fields, and in particular to a kind of organic luminescent compounds and preparation method thereof and device
Part.
Background technique
Organic light emission phenomenon refers to the phenomenon that converting electric energy to luminous energy using organic material.Utilize organic light emission phenomenon
Organic luminescent device usually has a structure in which comprising anode, cathode and organic material layer therebetween.
Organic material layer is formed as the multilayered structure formed by different materials to improve the efficiency of organic luminescent device and steady
It is qualitative, such as can be formed by hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer etc..In this way
OLED structure in, when applying voltage between two electrodes, hole and electronics are infused from anode and cathode respectively
Enter organic material layer, forms exciton when injected holes and electronics meet, and shine when these excitons return to ground state.
Material type and collocation form have the characteristics that rich and multifarious.In addition, for the OLED device of different structure
For part collocation, used photoelectric functional material has stronger selectivity, and identical material is in different structure device
Performance may also be completely totally different.Therefore, for the industry application requirement of current OLED device and the difference of OLED device
Functional film layer, the photoelectric characteristic demand of device, it is necessary to selection is more suitable for, the higher OLED functional material of performance or combination of materials,
Just it is able to achieve high efficiency, the overall characteristic of long-life and low-voltage of device.Current OLED is shown to the reality of Lighting Industry
For demand, the development of OLED material is also far from enough at present, lags behind the requirement of panel manufacturing enterprise, and as material, enterprise is opened
The organic functional material of hair higher performance is particularly important.
Summary of the invention
The object of the present invention is to provide a kind of new structural organic luminescent compounds and preparation method thereof and devices.
To achieve the goals above, technical solution of the present invention is specific as follows:
The present invention provides a kind of organic luminescent compounds, structural formula as described in chemical formula 1:
Wherein:
Ar1And Ar2Be each independently the aryl for being substituted or being unsubstituted, the arylamine group for being substituted or being unsubstituted,
Or the heterocycle for being substituted or being unsubstituted；
L1And L2Be same or different to each other, and be each independently direct key, the arlydene that is substituted or is unsubstituted,
Or the inferior heteroaryl for being substituted or being unsubstituted；
M and n are same or different to each other, and are each independently the integer more than or equal to 0；
R1To R6It is same or different to each other, and is each independently hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, carbonyl
Base, ester group, imide, amido, the silicyl for being substituted or being unsubstituted, the alkyl for being substituted or being unsubstituted, through taking
Generation or the naphthenic base being unsubstituted, the aryloxy group for being substituted or being unsubstituted, are substituted the alkoxy for being substituted or being unsubstituted
Or be unsubstituted alkyl sulfenyl, be substituted or be unsubstituted artyl sulfo, be substituted or be unsubstituted alkyl sulphonyl,
The aryl sulfonyl that is substituted or is unsubstituted, the alkenyl for being substituted or being unsubstituted, the aralkyl for being substituted or being unsubstituted,
The arylalkenyl that is substituted or is unsubstituted, the alkylaryl for being substituted or being unsubstituted, the aralkyl for being substituted or being unsubstituted
Amido, the arylamine group for being substituted or being unsubstituted, is substituted or is unsubstituted the heteroaryl amido for being substituted or being unsubstituted
Aryl phosphino-, the phosphine oxide group for being substituted or being unsubstituted, the aryl that is substituted or is unsubstituted or be substituted or not
The heterocycle or adjacent group being substituted are bonded to each other the ring to be formed and be substituted or be unsubstituted.
X is-O- ,-S- ,-SO2-、-C(R7)(R8)-、-N(R9)-、-Si(R10)(R11)-、-Sn(R12)(R13)-or-Ge
(R14)(R15)-；
R7~R15For the alkyl of the C1~C60 for being substituted or being unsubstituted, C3~C60 naphthenic base, be substituted or without
The alkenyl of substituted C2~C60, the cycloalkenyl of C3~C60, the alkynyl for the C3~C60 for being substituted or being unsubstituted, C3~C60
Cycloalkynyl radical, the C6~C60 aryl for being substituted or being unsubstituted, the C6~C60 aralkyl amido for being substituted or being unsubstituted, through taking
Generation or the C6~C60 heteroaryl amido being unsubstituted, the C6~C60 arylamine group for being substituted or being unsubstituted or C6~C60
Heteroaryl.
In the present invention, term " be substituted or be unsubstituted " means through one or more substituent groups selected from the following
Replace: deuterium, halogen group, itrile group, nitro, hydroxyl, carbonyl, ester group, imide, amido, phosphine oxide group, alkoxy, virtue
Oxygroup, alkyl sulfenyl, artyl sulfo, alkyl sulphonyl, aryl sulfonyl, silicyl, boryl, alkyl, naphthenic base, alkenyl,
Aryl, aralkyl, arylalkenyl, alkylaryl, alkyl amine group, aralkyl amido, heteroaryl amido, arylamine group, aryl phosphino-
And heterocycle, or be unsubstituted；Or mean that two or more substituent groups in the substituent group through illustrating above connected takes
Replace for base, or is unsubstituted.For example, the substituent group of two or more substituent groups connection " it may include xenyl.Change speech
It, xenyl can be aryl, or may be interpreted as the substituent group of two phenyl connection.
In the present invention, adjacent group can refer to taking for the atom for replacing the atom replaced with corresponding substituent group to be directly connected to
Dai Ji, the substituent group being spatially arranged closest to corresponding substituent group, or the atom that replaces corresponding substituent group to replace are another
Substituent group.Ring is formed in conjunction with adjacent group is meant that the aliphatic hydrocarbon for being formed in conjunction with adjacent group and being substituted or being unsubstituted
Ring, the aromatics hydrocarbon ring for being substituted or being unsubstituted, the aliphatic heterocyclic for being substituted or being unsubstituted, the virtue for being substituted or being unsubstituted
Race's heterocycle or its condensed ring.
In the present invention, aryl is not particularly limited, but preferably has 6 to 60 carbon atoms, and can be monocyclic aryl
Or polyaromatic.According to an embodiment, the carbon atom number of aryl is 6 to 40.According to another embodiment, the carbon of aryl
Atomicity is 6 to 20.The example of monocyclic aryl may include phenyl, xenyl, terphenyl etc., but not limited to this.Polyaromatic
Example may include naphthalene, anthryl, phenanthryl, base, fluoranthene base, triphenylene, pyrenyl, aphthacene base, pentacene, fluorenyl,
Indenyl, acenaphthenyl, benzo fluorenyl, Spirofluorene-based etc., but not limited to this.
In the above-mentioned technical solutions, the preferably described organic luminescent compounds are selected from appointing in [chemical formula 2]-[chemical formula 6]
Meaning one:
In [chemical formula 2]-[chemical formula 6], L1、L2、Ar1、Ar2, m, n and R1To R6Restriction and chemical formula 1 in limit
Range it is identical.
In the above-mentioned technical solutions, preferably L1And L2It is same or different to each other, and is each independently selected from one kind below
Or more type: direct key, the phenylene for being substituted or being unsubstituted, the biphenylene for being substituted or being unsubstituted, through taking
Generation or the sub- terphenyl being unsubstituted are substituted or the sub- tetrad phenyl being unsubstituted, the sub- naphthalene for being substituted or being unsubstituted
Base, the anthrylene for being substituted or being unsubstituted, the fluorenylidene for being substituted or being unsubstituted, the Ya Fei for being substituted or being unsubstituted
Base, the sub- pyrenyl for being substituted or being unsubstituted are substituted or the sub- triphenylene being unsubstituted, the Asia for being substituted or being unsubstituted
Pyridyl group, the sub- triazine radical for being substituted or being unsubstituted, is substituted or is unsubstituted the sub- pyrimidine radicals for being substituted or being unsubstituted
Sub- quinolyl, be substituted or be unsubstituted sub- quinazolyl, be substituted or be unsubstituted sub- carbazyl, be substituted or not
The sub- dibenzofuran group being substituted and the dibenzothiophene for being substituted or being unsubstituted.
In the above-mentioned technical solutions, preferably Ar1And Ar2It is each independently the xenyl for being substituted or being unsubstituted, has
The polyaromatic for being substituted or being unsubstituted of 6 to 40 carbon atoms, arylamine group or tool with 6 to 40 carbon atoms
There is the heterocycle for being substituted or being unsubstituted of 2 to 40 carbon atoms.
In the above-mentioned technical solutions, preferably wherein-(L1)n-Ar1And-(L2)m-Ar2It is each independently selected from following knot
Any one of structure:
In the above-mentioned technical solutions, any one of the most preferably described organic luminescent compounds in following structures:
In the present invention, the compound with various energy bandgaps can pass through the Ar in above-mentioned nuclear structure1、Ar2And R1
To R6Various substituent groups are introduced at position to synthesize.In addition, in the present invention, HOMO and lumo energy can also be by with upper
State the Ar of the nuclear structure of structure1、Ar2And R1To R6Various substituent groups are introduced at position to control.
In addition, can synthesize and be taken with introduced by introducing various substituent groups to the nuclear structure with above structure
The compound of the unique property of Dai Ji.For example, being commonly used in the substituent group of following material by introducing to nuclear structure: for making
Hole injection layer material, hole transport layer material, emitting layer material and the electron transport layer materials for making organic luminescent device, can close
At the material for meeting the needs of needed for each organic material layer.
The present invention also provides a kind of preparation methods of organic luminescent compounds, comprising the following steps:
The preparation of step 1, intermediate C
Raw material A and raw material B are dissolved in toluene under nitrogen atmosphere, sodium tert-butoxide and 2- dicyclohexyl phosphorus-is then added
2,4,6- tri isopropyl biphenyls, then add palladium acetate, will be stirred to react after reaction heating, after reaction, are cooled to
Toluene is concentrated, is recrystallized using ethyl alcohol, obtain intermediate C except desalting and catalyst by room temperature；Preferable reaction temperature is
100 DEG C, mixing time is 10 hours；
The preparation of step 2, intermediate E
After intermediate C and intermediate D are dissolved in toluene and tetrahydrofuran, p-methyl benzenesulfonic acid is added thereto, by institute
Be stirred to react after object heating, then after temperature is reduced to room temperature, distilled water is added into reaction solution and sodium carbonate neutralizes
Organic phase is concentrated into a little solvent by solution to neutrality, liquid separation, extraction, is added dropwise in cold ethyl alcohol, and precipitation obtains intermediate
E；Preferable reaction temperature is 50 DEG C, and mixing time is 2 hours；
The preparation of step 3, intermediate G
Intermediate E and intermediate F are dissolved into toluene/ethanol/water in the mixed solvent under nitrogen atmosphere, then thereto
Tetra-triphenylphosphine palladium and sodium carbonate is added, will be stirred to react after reaction heating, after reaction, is cooled to room temperature, liquid separation,
Extraction, concentration, are recrystallized using ethyl alcohol, obtain intermediate G；Preferable reaction temperature is 90 DEG C, and mixing time is 12 hours；
The preparation of compound shown in step 4, chemical formula 1
After intermediate G and intermediate H are dissolved in toluene under nitrogen atmosphere, sodium tert-butoxide is added thereto, is then added
Add tri-tert-butylphosphine and tris(dibenzylideneacetone) dipalladium, is stirred to react after gains are heated, then temperature is reduced to
After room temperature, gains are filtered toluene to be concentrated, and gains are crossed column using methylene chloride and petroleum ether except desalting, are made
It is standby to obtain compound shown in chemical formula 1；Preferable reaction temperature is 100 DEG C, and mixing time is 12 hours；
Its synthetic route is as follows:
Wherein, Y, Z and Hr are halogen, and Y and Z cannot be identical halogen, L simultaneously1、L2、Ar1、Ar2, m, n and R1Extremely
R6Restriction and chemical formula 1 in the range that limits it is identical.
The present invention also provides a kind of organic luminescent devices, comprising: first electrode, second electrode and setting are in first electricity
One or more organic material layers between pole and the second electrode, wherein one or more in the organic material layer
A layer includes organic luminescent compounds of the present invention.
It is preferred that the organic material layer includes luminescent layer, and the luminescent layer includes compound of the present invention as institute
State the main body of luminescent layer.It may include the phosphorescence host material of the compound that is indicated by chemical formula 1 as luminescent layer as an example
Material.
The further preferred organic material layer includes the compound as main body, and includes other organic compounds
Object, metal or metallic compound are as dopant.
As another example, the organic material layer comprising the compound indicated by chemical formula 1 includes to be indicated by chemical formula 1
Compound as main body, and the compound can be used together with based on the dopant of iridium (Ir).
It is preferred that the organic material layer includes electron transfer layer, electron injecting layer and carries out electron-transport and electricity simultaneously
One or more layers in the layer of son injection, and one or more layers in the layer include chemical combination of the present invention
Object.
It is preferred that the organic material layer includes hole injection layer, hole transmission layer and carries out hole injection and sky simultaneously
One or more layers in the layer of cave transmission, and one or more layers in the layer include chemical combination of the present invention
Object.
It is preferred that the organic material layer includes hole transmission layer, electronic barrier layer and hole transport and electronic barrier layer
In one or more layers, and one or more layers in the layer include compound of the present invention.
Common method for manufacturing organic luminescent device and material can be used to manufacture for organic luminescent device of the invention,
The difference is that one or more layers in organic material layer are formed using compound of the present invention.
When manufacturing organic luminescent device, solution coating process and vacuum deposition method can be used that compound is formed as organic
Material layer.In the present invention, solution coating process means spin coating, dip-coating, ink jet printing, silk-screen printing, spraying, roller coating etc., but not
It is limited to this.
The organic material layer of organic luminescent device of the invention is formed as single layer structure, but may be alternatively formed to its middle layer and contain
There are two or more organic material layer multilayered structure.For example, organic luminescent device of the invention may have a structure such that,
It includes hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer etc. as organic material layer.So
And the structure of organic luminescent device is without being limited thereto, it may include fewer number of organic material layer.
For example, organic luminescent device according to the present invention can be manufactured by following process: heavy by using physical vapor
Product (PVD) method (for example, sputtering or electron beam evaporation) makes conductive metal, metal oxide or its alloy deposition in base
Anode is formed on bottom, formation includes organic material of hole injection layer, hole transmission layer, luminescent layer and electron transfer layer on anode
Then the bed of material deposits the material that can be used as cathode on organic material layer.In addition to this method, organic luminescent device can also lead to
It crosses and is sequentially depositing cathode material, organic material layer and anode material in substrate to manufacture.
Organic material layer can have such multilayered structure comprising hole injection layer, hole transmission layer, luminescent layer, electricity
Sub- transport layer etc., but not limited to this, and can have single layer structure.In addition, various polymer materials can be used in organic material layer
By solvent method (such as spin coating, dip-coating, blade coating (doctorblading), silk-screen printing, ink jet printing or thermal shift assay) rather than
Sedimentation is prepared into fewer number of layer.
As anode material, it is usually preferred to the material with big work function, so that smoothly injecting holes into organic
In material layer.The specific example that can be used in anode material of the invention includes metal, for example, vanadium, chromium, copper, zinc or gold or its
Alloy；Metal oxide, such as zinc oxide, indium oxide, tin indium oxide (ITO) or indium zinc oxide (IZO)；Metal and oxide
Combination, such as ZnO:Al or SnO2:Sb；Conducting polymer, such as poly- (3- methyl compound), poly- [3,4- (ethylidene -1,2-
Two oxygroups) compound] (PEDOT), polypyrrole or polyaniline, but not limited to this.
As cathode material, it is usually preferred to the material with small work function, so that smoothly injecting electrons into organic
In material layer.The specific example that can be used in cathode material of the invention includes metal, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium,
Lithium, gadolinium, aluminium, silver, tin or lead or its alloy；Sandwich, such as LiF/Al or LiO2/ Al etc., but not limited to this.
As hole-injecting material, have anode material work function and around organic material layer highest occupied molecular
The material of highest occupied molecular orbital (HOMO) between track (HOMO) is preferably as being conducive to connect from anode at low voltage
Receive the material in hole.The specific example of hole-injecting material includes metalloporphyrin, Oligopoly thiophene, organic material based on arylamine
Material, the organic material based on six nitriles, six azepine triphenylene, the organic material based on quinacridone, based on organic material,
Anthraquinone, based on polyaniline or the conducting polymer based on polythiophene etc., but not limited to this.
As hole mobile material, the material with high hole mobility is suitable for receiving from anode or hole injection layer
Hole and by the material of hole transport to luminescent layer.Its specific example includes organic material, conducting polymer based on arylamine
Or there is the block copolymer etc. of conjugate moiety and non-conjugated portion simultaneously, but not limited to this.
As luminescent material, be conducive to the material of the quantum efficiency of fluorescence or phosphorescence preferably as difference can be passed through
Hole and electronics are received from hole transmission layer and electron transfer layer and make hole and electronics in conjunction with come the light that issues visible light region
Material.Its specific example includes 8- Hydroxy-quinolin aluminum complex (Alq3), the compound based on carbazole, two polystyrene-based
Compound, BAlq, 10- hydroxy benzo quinoline-metallic compound, the compound based on benzothiazole and based on benzimidazole, base
In polymer, spiro-compound, polyfluorene or the rubrene etc. of poly- (to phenylene vinylidene) (PPV), but not limited to this.
Organic material layer comprising the compound indicated by chemical formula 1 includes to be used as master by the compound that chemical formula 1 indicates
Body, and the compound can be used together with the dopant based on iridium (Ir).
As electron transport material, the material with high electron mobility is suitable for being conducive to receive electronics simultaneously from cathode
By the material of electron-transport to luminescent layer.Its specific example includes the Al complex of 8-hydroxyquinoline, comprising Alq3Complex,
Organic free radical compound or flavonol-metal complex etc., but not limited to this.
It can be top emission type, bottom emission type according to the organic luminescent device of this specification according to used material
Or dual-side luminescent type.
Compound according to the present invention can also be used in the organic electronic device using principle similar with organic luminescent device,
Including organic solar batteries, organic photoconductor, organic transistor etc..
The beneficial effects of the present invention are:
Organic luminescent compounds provided by the invention may be used as the material of the organic material layer of organic luminescent device.It uses
Organic luminescent compounds of the invention can improve efficiency, low driving voltage in an organic light emitting device and/or improve the application longevity
Life feature.Especially when the device prepared by organic luminescent compounds of the invention as luminescent layer material of main part is compared with device
Example 1 is compared, and either efficiency, voltage, brightness or the service life obtains larger change, especially device than known OLED material
Life time decay obtains biggish promotion.
Preparation method is simple for organic luminescent compounds provided by the invention, and yield is high, is easy to industrialization.
Specific embodiment
Hereinafter, by referring to following embodiment to the method for the compound for being used to prepare chemical formula 1 and be used for using
The method of the compound manufacture organic luminescent device is specifically described.However, being merely to illustrate that property of following embodiment
Purpose, and scope of the present disclosure without being limited thereto.
<intermediate Preparation>
The synthetic route of intermediate G and E ' are as follows:
The synthesis of<preparation example 1>compound G-1 and compound 1
1) synthesis of compound G-1
A) under nitrogen atmosphere in 500mL round-bottomed flask by raw material A -1 (14.0g, 50mmol) and raw material B (9.8g,
It 50mmol) is dissolved in the dry toluene of 300mL.And sodium tert-butoxide (9.6g, 100mmol) and bis- ring of 2- is added in backward flask
Hexyl phosphorus -2,4,6- tri isopropyl biphenyl (4.76g, 10mmol) then add palladium acetate (0.56g, 2.5mmol).It will reaction
100 DEG C are heated to, is stirred 10 hours.After reaction, it is cooled to room temperature, except desalting and catalyst, toluene is concentrated, is used
200mL ethyl alcohol is recrystallized, and intermediate C-1 (16.83g, yield: 85%) are obtained.
B) in 500mL round-bottomed flask by intermediate C-1 (15.0g, 37.88mmol) and intermediate D-1 (7.42g,
After 37.88mmol) being dissolved completely in the mixed solution of 150mL toluene and 50mL tetrahydrofuran, added thereto to toluene sulphur
Gains are heated to 50 DEG C and stirred 2 hours by sour (8.6g, 50mmol).After temperature is reduced to room temperature again, into reaction solution
It is added in distilled water 100mL and sodium carbonate and solution to neutrality.Organic phase is concentrated into a little solvent by liquid separation, extraction, is dripped
It adds in cold ethyl alcohol, precipitation is obtained into intermediate E -1 (13.40g, yield 90%).
C) under nitrogen atmosphere in 500mL round-bottomed flask, by intermediate E -1 (13.0g, 33.07mmol) and intermediate F-1
Phenyl boric acid (4.44g, 36.38mmol) is dissolved into 150mL toluene/50mL ethyl alcohol/50mL water in the mixed solvent.Then thereto
Tetra-triphenylphosphine palladium (0.76g, 0.66mmol) and sodium carbonate (9.13g, 66.14mmol) is added.Reaction is heated to 90 DEG C, is stirred
It mixes 12 hours.After reaction, it is cooled to room temperature, liquid separation, extraction, concentration recrystallized using 200mL ethyl alcohol, is obtained
Mesosome G-1 (11.51g, yield 80%).
2) synthesis of compound 1
Under nitrogen atmosphere in 500mL round-bottomed flask by intermediate G-1 (11.0g, 25.28mmol) and bromobenzene (4.34g,
After 27.81mmol) being dissolved completely in 200mL dry toluene, sodium tert-butoxide (4.85g, 50.56mmol) is added thereto, so
Tri-tert-butylphosphine (1.11g, 5.06mmol) and tris(dibenzylideneacetone) dipalladium (0.23g, 0.25mmol) are added afterwards, by gained
Object is heated to 100 DEG C and stirs 12 hours.After temperature is reduced to room temperature again, gains are filtered to remove and desalt, toluene is dense
Contracting, and use methylene chloride: gains are crossed column with prepare compound 1 (10.6g, yield: 82%) by petroleum ether=1:5.
ESI-MS (m/z) (M+): theoretical value 511.19, measured value 511.75.
The synthesis of<preparation example 2>compound 7
1) intermediate G-7 is prepared according to the synthetic method of intermediate G-1 in preparation example 1, the difference is that using intermediate
Body A-7, C-7, E-7 replace A-1, C-1, E-1.
2) according to the synthetic method prepare compound 7 of 1 compound 1 of preparation example, the difference is that using intermediate G-7,
H-7 replaces intermediate G-1, H-1.Obtain compound 7 (14.73g, yield: 79%).ESI-MS (m/z) (M+): theoretical value is
676.25 measured value 676.55
The synthesis of<preparation example 3>compound 23
Intermediate G-23 is prepared according to the synthetic method of intermediate G-1 in preparation example 1, the difference is that using intermediate
A-23, C-23, E-23, F-23 replace A-1, C-1, E-1, F-1.
2) according to the synthetic method prepare compound 23 of 1 compound 1 of preparation example, the difference is that using intermediate G-
23, H-23 replaces intermediate G-1, H-1.Obtain compound 23 (16.22g, yield: 83%).ESI-MS (m/z) (M+): theoretical
Value is 651.22, measured value 651.37.
The synthesis of<preparation example 4>compound 32
Intermediate G-32 is prepared according to the synthetic method of intermediate G-1 in preparation example 1, the difference is that using intermediate
A-32, C-32, E-32, F-23 replace A-1, C-1, E-1, F-1.
2) according to the synthetic method prepare compound 32 of 1 compound 1 of preparation example, the difference is that using intermediate G-
32, H-32 replaces intermediate G-1, H-1.Obtain compound 32 (12.05g, yield: 78%).ESI-MS (m/z) (M+): theoretical
Value is 618.18, measured value 618.83.
The synthesis of<preparation example 5>compound 36
1) intermediate G-36 is prepared according to the synthetic method of intermediate G-1 in preparation example 1, the difference is that using intermediate
Body A-36, C-36, E-36 replace A-1, C-1, E-1.
2) according to the synthetic method prepare compound 36 of 1 compound 1 of preparation example, the difference is that using intermediate G-
36, H-36 replaces intermediate G-1, H-1.Obtain compound 36 (13.33g, yield: 85%).ESI-MS (m/z) (M+): theoretical
Value is 627.26, measured value 627.13.
The synthesis of<preparation example 6>compound 50
1) intermediate G-50 is prepared according to the synthetic method of intermediate G-1 in preparation example 1, the difference is that using intermediate
Body A-50, C-50, E-50, F-50 replace A-1, C-1, E-1, F-1.
2) according to the synthetic method prepare compound 50 of 1 compound 1 of preparation example, the difference is that using intermediate G-
50, H-50 replaces intermediate G-1, H-1.Obtain compound 50 (15.59g, yield: 75%).ESI-MS (m/z) (M+): theoretical
Value is 831.30, measured value 831.21.
The synthesis of<preparation example 7>compound 54
Under nitrogen atmosphere in 500mL round-bottomed flask by raw material A ' -54 (12.30g, 50mmol) and raw material B (9.8g,
It 50mmol) is dissolved in the dry toluene of 300mL.And sodium tert-butoxide (9.6g, 100mmol) and bis- ring of 2- is added in backward flask
Hexyl phosphorus -2,4,6- tri isopropyl biphenyl (4.76g, 10mmol) then add palladium acetate (0.56g, 2.5mmol).It will reaction
100 DEG C are heated to, is stirred 10 hours.After reaction, it is cooled to room temperature, except desalting and catalyst, toluene is concentrated, is used
200mL ethyl alcohol is recrystallized, and intermediate C ' -54 (15.44g, yield: 86%) are obtained.
In 500mL round-bottomed flask by intermediate C ' -54 (15.0g, 41.77mmol) and intermediate D-1 (8.19g,
After 41.77mmol) being dissolved completely in the mixed solution of 150mL toluene and 50mL tetrahydrofuran, added thereto to toluene sulphur
Gains are heated to 50 DEG C and stirred 2 hours by sour (8.63g, 50.12mmol).After temperature is reduced to room temperature again, Xiang Fanying
It is added in liquid in distilled water 100mL and sodium carbonate and solution to neutrality.Organic phase is concentrated into a little solvent by liquid separation, extraction, will
It is added dropwise in cold ethyl alcohol dissolution, and precipitation is obtained intermediate E ' -54 (13.80g, yield 92%).
By intermediate E ' -54 (13.0g, 36.2mmol) and intermediate F ' -54 in 500mL round-bottomed flask under nitrogen atmosphere
After (9.85g, 36.2mmol) is dissolved completely in 200mL dry toluene, thereto add sodium tert-butoxide (6.95g,
72.4mmol), then add tri-tert-butylphosphine (1.46g, 7.24mmol) and tris(dibenzylideneacetone) dipalladium (0.33g,
0.36mmol), gains are heated to 100 DEG C and stirred 12 hours.After temperature is reduced to room temperature again, by gains filter with
Except desalting, toluene is concentrated, and uses methylene chloride: gains are crossed column with prepare compound 54 by petroleum ether=1:5
(16.76g, yield: 84%).ESI-MS (m/z) (M+): theoretical value 551.22, measured value 551.25.
The synthesis of<preparation example 8>compound 65
Intermediate E ' -54 is prepared according to the synthetic method of intermediate E ' -54 in preparation example 7
According to the synthetic method prepare compound 65 of 7 compound 54 of preparation example, the difference is that using intermediate F ' -65
Instead of intermediate F ' -54.Obtain compound 65 (17.7g, yield: 80%).ESI-MS (m/z) (M+): theoretical value 612.22,
Measured value is 612.21.
The synthesis of<preparation example 9>compound 75
Intermediate E ' -75 are prepared according to the synthetic method of intermediate E ' -54 in preparation example 7, the difference is that in use
Mesosome A ' -75, C ' -75 replace A ' -54, C ' -54.
According to the synthetic method prepare compound 75 of 7 compound 54 of preparation example, the difference is that using intermediate E '-
75, F ' -75 replaces intermediate E ' -54, F ' -54.Obtain compound 75 (17.58g, yield: 79%).ESI-MS (m/z) (M+):
Theoretical value is 618.21, measured value 618.71.
The synthesis of<preparation example 10>compound 90
Intermediate E ' -90 are prepared according to the synthetic method of intermediate E ' -54 in preparation example 7, the difference is that in use
Mesosome A ' -90, C ' -90, D-90 replace A ' -54, C ' -54, D-54.
According to the synthetic method prepare compound 90 of 7 compound 54 of preparation example, the difference is that using intermediate E '-
90, F ' -90 replaces intermediate E ' -54, F ' -54.Obtain compound 90 (15.05g, yield: 81%).ESI-MS (m/z) (M+):
Theoretical value is 513.17, measured value 513.46.
The synthesis of<preparation example 11>compound 94
Intermediate E ' -94 are prepared according to the synthetic method of intermediate E ' -54 in preparation example 7, the difference is that in use
Mesosome A ' -94, C ' -94, D-94 replace A ' -54, C ' -54, D-54.
According to the synthetic method prepare compound 94 of 7 compound 54 of preparation example, the difference is that using intermediate E '-
94, F ' -94 replaces intermediate E ' -54, F ' -54.Obtain compound 94 (20.41g, yield: 77%).ESI-MS (m/z) (M+):
Theoretical value is 732.31, measured value 732.42.
Device embodiments 1: a kind of electroluminescent device, preparation step include:
A) the ito anode layer on transparent substrate layer is cleaned, cleans each 15 points with deionized water, acetone, EtOH Sonicate respectively
Then clock is handled 2 minutes in plasma cleaner；B) on ito anode layer, hole note is deposited by vacuum evaporation mode
Enter layer material HAT-CN, with a thickness of 10nm, this layer is as hole injection layer；C) on hole injection layer, by vacuum evaporation side
Hole mobile material NPB is deposited in formula, and with a thickness of 60nm, which is hole transmission layer；D) it is deposited and shines on hole transmission layer
Layer uses the compound 1 in embodiment 1 as material of main part, and Ir (ppy) 3 is used as dopant material, Ir (ppy) 3 and compound 1
Mass ratio be 10:90, with a thickness of 30nm；F) on luminescent layer, electron transport material is deposited by vacuum evaporation mode
TPBI, with a thickness of 40nm；G) on electron transfer layer, vacuum evaporation electron injecting layer LiF, with a thickness of 1nm, which is electronics
Implanted layer；H) on electron injecting layer, vacuum evaporation cathode Al (100nm), the layer is cathode reflection electrode layer.
Device embodiments 2: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 7.
Device embodiments 3: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 23.
Device embodiments 4: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 32.
Device embodiments 5: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 36.
Device embodiments 6: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 50.
Device embodiments 7: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 54.
Device embodiments 8: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 65.
Device embodiments 9: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 75.
Device embodiments 10: the present embodiment is with device embodiments 1 the difference is that the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 90.
Device embodiments 11: the present embodiment is with device embodiments 1 the difference is that the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 94.
Device comparative example 1: the present embodiment is with device embodiments 1 the difference is that the luminescent layer master of electroluminescent device
Body material is CBP.
The Electroluminescence Properties of the OLED of manufacture
Voltage, electric current according to measurement device embodiment 1~11 and the organic electroluminescence device of the manufacture of comparative example 1 is close
Degree, brightness and service life, as a result as following table indicates.
It can be seen that organic luminescent compounds of the present invention can be applied to the production of OLED luminescent device by the result in table,
And compared with device comparative example 1, either efficiency, voltage, brightness or service life obtain larger change than known OLED material
It sees, especially the life time decay of device obtains biggish promotion.
Obviously, the above embodiments are merely examples for clarifying the description, and does not limit the embodiments.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And it is extended from this it is obvious variation or
It changes still within the protection scope of the invention.
Claims (10)
1. a kind of organic luminescent compounds, which is characterized in that its structural formula as described in chemical formula 1:
Wherein:
Ar1And Ar2Be each independently the aryl for being substituted or being unsubstituted, the arylamine group for being substituted or being unsubstituted or
The heterocycle for being substituted or being unsubstituted；
L1And L2Be same or different to each other, and be each independently direct key, the arlydene that is substituted or is unsubstituted or
The inferior heteroaryl for being substituted or being unsubstituted；
M and n are same or different to each other, and are each independently the integer more than or equal to 0；
R1To R6It is same or different to each other, and is each independently hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, carbonyl, ester
Base, amido, the silicyl for being substituted or being unsubstituted, the alkyl for being substituted or being unsubstituted, is substituted or not imide
The naphthenic base that is substituted, the alkoxy for being substituted or being unsubstituted, the aryloxy group for being substituted or being unsubstituted, be substituted or without
Substituted alkyl sulfenyl, the alkyl sulphonyl for being substituted or being unsubstituted, is substituted the artyl sulfo for being substituted or being unsubstituted
Or be unsubstituted aryl sulfonyl, be substituted or be unsubstituted alkenyl, be substituted or be unsubstituted aralkyl, be substituted
Or be unsubstituted arylalkenyl, be substituted or be unsubstituted alkylaryl, be substituted or be unsubstituted aralkyl amido, warp
Replace or be unsubstituted heteroaryl amido, the arylamine group for being substituted or being unsubstituted, the aryl that is substituted or is unsubstituted
It phosphino-, the phosphine oxide group for being substituted or being unsubstituted, the aryl for being substituted or being unsubstituted or is substituted or is unsubstituted
Heterocycle or adjacent group be bonded to each other the ring to be formed and be substituted or be unsubstituted；
X is-O- ,-S- ,-SO2-、-C(R7)(R8)-、-N(R9)-、-Si(R10)(R11)-、-Sn(R12)(R13)-or-Ge (R14)
(R15)-；
R7~R15For the alkyl of the C1~C60 for being substituted or being unsubstituted, C3~C60 naphthenic base, be substituted or be unsubstituted
The alkenyl of C2~C60, the cycloalkenyl of C3~C60, the alkynyl for the C3~C60 for being substituted or being unsubstituted, C3~C60 cycloalkyne
Base, the C6~C60 aryl for being substituted or being unsubstituted, the C6~C60 aralkyl amido for being substituted or being unsubstituted, be substituted or
C6~C60 heteroaryl amido for being unsubstituted, the C6~C60 arylamine group for being substituted or being unsubstituted or C6~C60 it is miscellaneous
Aryl.
2. organic luminescent compounds according to claim 1, which is characterized in that it is selected from [chemical formula 2]-[chemical formula 6]
In any one:
3. organic luminescent compounds according to claim 1, which is characterized in that L1And L2It is same or different to each other, and each
From one or more of seed types independently selected from the following: direct key, the phenylene for being substituted or being unsubstituted are substituted or not
The biphenylene that is substituted, the sub- terphenyl for being substituted or being unsubstituted, the sub- tetrad phenyl for being substituted or being unsubstituted, warp
Replace or be unsubstituted naphthylene, be substituted or be unsubstituted anthrylene, be substituted or be unsubstituted fluorenylidene, through taking
Generation or the phenanthrylene being unsubstituted, the sub- pyrenyl for being substituted or being unsubstituted, the sub- triphenylene for being substituted or being unsubstituted, warp
Replace or be unsubstituted sub-pyridyl group, the sub- pyrimidine radicals for being substituted or being unsubstituted, the sub- triazine that is substituted or is unsubstituted
Base, the sub- quinazolyl that is substituted or is unsubstituted, is substituted or is unsubstituted the sub- quinolyl for being substituted or being unsubstituted
Sub- carbazyl is substituted or the sub- dibenzofuran group being unsubstituted and the dibenzothiophene for being substituted or being unsubstituted.
4. organic luminescent compounds according to claim 1, which is characterized in that Ar1And Ar2It is each independently and is substituted
Or be unsubstituted xenyl, the polyaromatic for being substituted or being unsubstituted with 6 to 40 carbon atoms, have 6 to 40
The arylamine group of carbon atom or the heterocycle for being substituted or being unsubstituted with 2 to 40 carbon atoms.
5. organic luminescent compounds according to claim 1, which is characterized in that wherein-(L1)n-Ar1And-(L2)m-Ar2
It is each independently selected from any one in flowering structure:
6. organic luminescent compounds according to claim 1, which is characterized in that it is any one in following structures
It is a:
7. a kind of preparation method of organic luminescent compounds described in claim 1, which comprises the following steps:
The preparation of step 1, intermediate C
Raw material A and raw material B are dissolved in toluene under nitrogen atmosphere, sodium tert-butoxide and 2- dicyclohexyl phosphorus -2,4 is then added,
6- tri isopropyl biphenyl, then adds palladium acetate, will be stirred to react after reaction heating, after reaction, is cooled to room temperature,
Except desalting and catalyst, toluene is concentrated, is recrystallized using ethyl alcohol, intermediate C is obtained；
The preparation of step 2, intermediate E
After intermediate C and intermediate D are dissolved in toluene and tetrahydrofuran, p-methyl benzenesulfonic acid is added thereto, by gains
It is stirred to react, then after temperature is reduced to room temperature, is added into reaction solution in distilled water and sodium carbonate and solution after heating
To neutrality, organic phase is concentrated into a little solvent by liquid separation, extraction, is added dropwise in cold ethyl alcohol, and precipitation obtains intermediate E；
The preparation of step 3, intermediate G
Intermediate E and intermediate F are dissolved into toluene/ethanol/water in the mixed solvent under nitrogen atmosphere, are then added thereto
Tetra-triphenylphosphine palladium and sodium carbonate will be stirred to react after reaction heating, after reaction, is cooled to room temperature, liquid separation, extraction
It takes, be concentrated, recrystallized using ethyl alcohol, obtain intermediate G；
The preparation of compound shown in step 4, chemical formula 1
After intermediate G and intermediate H are dissolved in toluene under nitrogen atmosphere, sodium tert-butoxide is added thereto, then adds three
Tert-butyl phosphine and tris(dibenzylideneacetone) dipalladium are stirred to react after heating gains, then temperature are reduced to room temperature
Afterwards, gains are filtered toluene to be concentrated, and gains are crossed column using methylene chloride and petroleum ether, be prepared into except desalting
To compound shown in chemical formula 1；
Its synthetic route is as follows:
Wherein, Y, Z and Hr are halogen, and Y and Z cannot be identical halogen simultaneously.
8. a kind of organic luminescent device, comprising: first electrode, second electrode and setting are in the first electrode and second electricity
One or more organic material layers between pole, which is characterized in that wherein one or more in the organic material layer
Organic hair that layer is prepared comprising organic luminescent compounds as claimed in any one of claims 1 to 6 or claim 7
Optical compounds.
9. organic luminescent device according to claim 8, which is characterized in that wherein the organic material layer includes shining
Layer, and the luminescent layer includes prepared by organic luminescent compounds as claimed in any one of claims 1 to 6 or claim 7
Material of main part of the organic luminescent compounds as the luminescent layer.
10. organic luminescent device according to claim 8, which is characterized in that
Wherein the organic material layer include electron transfer layer, electron injecting layer and carry out simultaneously electron-transport and electronics note
Enter one or more layers in layer, and one or more layers in the layer include claim 1-6 any one institute
The organic luminescent compounds for organic luminescent compounds or claim 7 preparation stated；
Or wherein the organic material layer includes hole injection layer, hole transmission layer and carries out hole injection and sky simultaneously
One or more layers in the transport layer of cave, and one or more layers in the layer include claim 1-6 any one
The organic luminescent compounds prepared by organic luminescent compounds or claim 7 described in；
Or wherein the organic material layer includes hole transmission layer, electronic barrier layer and hole transport and electronic barrier layer
In one or more layers, and one or more layers in the layer include it is as claimed in any one of claims 1 to 6
The organic luminescent compounds prepared by organic luminescent compounds or claim 7.
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| CN110373182A (en) * | 2019-07-10 | 2019-10-25 | 吉林奥来德光电材料股份有限公司 | A kind of organic luminescent compounds and preparation method thereof and device |
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| KR20140068772A (en) * | 2012-11-28 | 2014-06-09 | 에스에프씨 주식회사 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| WO2014104664A1 (en) * | 2012-12-24 | 2014-07-03 | 주식회사 두산 | Organic compound and organic electroluminescent element comprising same |
| US20140374724A1 (en) * | 2011-12-07 | 2014-12-25 | Doosan Corporation | Organic light-emitting compound and organic electroluminescent device using same |
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| KR20130115161A (en) * | 2012-04-10 | 2013-10-21 | 에스에프씨 주식회사 | Heterocyclic com pounds and organic light-emitting diode including the same |
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