CN107793419A - A kind of imidazo azole derivatives and its organic luminescent device - Google Patents

A kind of imidazo azole derivatives and its organic luminescent device Download PDF

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CN107793419A
CN107793419A CN201711005612.XA CN201711005612A CN107793419A CN 107793419 A CN107793419 A CN 107793419A CN 201711005612 A CN201711005612 A CN 201711005612A CN 107793419 A CN107793419 A CN 107793419A
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imidazo
substituted
layer
azole derivatives
luminescent device
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蔡辉
韩春雪
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of imidazo azole derivatives and its organic luminescent device, belongs to technical field of organic luminescence materials.The imidazo azole derivatives are by introducing condensed ring class rigidity, close packed structure, make that the imidazo azole derivatives thermal stability obtained by the present invention is high, good film-forming property, available for preparing organic luminescent device, especially as the hole mobile material in organic luminescent device, high efficiency, longevity advantage are shown, better than existing conventional OLED.The imidazo azole derivatives that the present invention obtains have good application effect in OLED luminescent devices, have good industrialization prospect.

Description

A kind of imidazo azole derivatives and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of imidazo azole derivatives and its organic hair Optical device.
Background technology
Aromatic diamines analog derivative was used first from 1987 as hole mobile material, is with 8-hydroxyquinoline aluminium (Alq3) Emitting layer material, prepare Organic Light Emitting Diode (the Organic Light- of high efficiency, high brightness and low driving voltage Emitting Diode, OLED) since, due to various features such as its is low in energy consumption, brightness is high, visual angle is wide, fast response times by Great concern is arrived, the research of organic electroluminescent (Emissive Layer, EL) has become current luminescence display field One of focus.People have been carried out largely from luminescent material, preparation technology to various aspects such as luminescence mechanism, device architectures Research work, the photoelectric properties of device are significantly improved, but the factor such as the luminous efficiency of device and life-span is still resistance Hinder one of commercialized bottlenecks of OLED.
Electroluminescent (EL) is double molecule course, to obtain larger luminous efficiency, does not require nothing more than electronics and hole is carried out Effective injection transport with it is compound, and need the injection in electronics and hole balanced, therefore, two electrodes and organic layer and two are organic Interlayer can seem particularly significant with matching to recombination luminescence.
At present, organic luminescent device develops towards practical, commercialization, but still needs in the efficiency of device and on the life-span Further to improve, this it is also proposed higher requirement to organic material.The more preferable material of new performance how is designed to carry out Regulation, is always those skilled in the art's urgent problem to be solved.
The content of the invention
It is an object of the invention to provide a kind of imidazo azole derivatives and its organic luminescent device, miaow provided by the invention Azoles and azole derivatives thermal stability height, good film-forming property, the organic luminescent device made of the derivative, show efficiently The advantages of rate, long-life, it is the luminous organic material of function admirable.
Present invention firstly provides a kind of imidazo azole derivatives, structural formula is：
Wherein, Ar1、Ar2, L independences the substituted or unsubstituted aryl selected from C6~C60, C10~C60 substitution or not Substituted fused ring aryl, C3~C60 substituted or unsubstituted heteroaryl, C9~C60 substituted or unsubstituted condensed ring heteroaryl One kind in base.
Preferably, Ar1、Ar2The substitution of the independent substituted or unsubstituted aryl selected from C6~C25, C10~C20 or not Substituted fused ring aryl, C3~C18 substituted or unsubstituted heteroaryl, C9~C20 substituted or unsubstituted condensed ring heteroaryl One kind in base；L be selected from C6~C20 substituted or unsubstituted aryl, C10~C20 substituted or unsubstituted fused ring aryl, One kind in C9~C20 substituted or unsubstituted fused ring heteroaryl.
Preferably, Ar1、Ar2It is independent selected from phenyl, naphthyl, phenanthryl, anthryl, pyrenyl, base, xenyl, terphenyl, Indenyl, indyl, pyridine radicals, pyrimidine radicals, triazine radical, furyl, thienyl, dibenzothiophenes base, dibenzofuran group, quinoline Base, isoquinolyl, phenoxazine base, phenothiazinyl, acridinyl, carbazyl, fluorenyl or the fluorenyl of spiral shell two.
Preferably, L is selected from following structure：
Wherein, R1、R2、R3The independent alkyl selected from C1~C10, C6~C20 substituted or unsubstituted aryl, C10~ One kind in C20 substituted or unsubstituted fused ring aryl.
Preferably, any one of a kind of imidazo azole derivatives in structure as shown below：
The present invention also provides a kind of application of imidazo azole derivatives in an organic light emitting device.
Preferably, organic luminescent device includes negative electrode, anode and is placed in one or more organic between two electrode Compound layer, organic compound layer contain a kind of imidazo azole derivatives.
Preferably, organic compound layer includes hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole resistance At least one layer in barrier, electron transfer layer, electron injecting layer；It is at least one layer of in the organic compound layer to contain a kind of imidazoles And azole derivatives.
Preferably, a kind of imidazo azole derivatives are contained in hole transmission layer.
Beneficial effects of the present invention:
Present invention firstly provides a kind of imidazo azole derivatives, the imidazo azole derivatives have to be tied shown in formula (I) Structure, by introducing condensed ring class rigidity, close packed structure, make the imidazo azole derivatives thermal stability obtained by the present invention it is high, Good film-forming property, available for organic luminescent device is prepared, especially as the hole mobile material in organic luminescent device, show High efficiency, longevity advantage, better than existing conventional OLED.Imidazo azole derivatives of the present invention light in OLED There is good application effect in device, there is good industrialization prospect.
Embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described with reference to embodiment, still It should be appreciated that these descriptions are simply further explanation the features and advantages of the present invention, rather than to the claims in the present invention Limitation.
Alkyl of the present invention refers to minus the alkyl that a hydrogen atom forms in alkane molecule, and it can be straight chain alkane Base, branched alkyl, cycloalkyl, example may include methyl, ethyl, propyl group, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth Base, amyl group, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Aryl of the present invention refers to after removing a hydrogen atom on the aromatic core carbon of phenyl molecule, is left the total of univalent perssad Claiming, example may include phenyl, 4- aminomethyl phenyls, 4- tert-butyl-phenyls, 2- ethylphenyls, xenyl or terphenyl etc., but not It is limited to this.
Fused ring aryl of the present invention refers to after removing a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule, is left univalent perssad General name, example may include 1- naphthyls, 2- naphthyls, anthryl, phenanthryl, pyrenyl or base etc., but not limited to this.
Heteroaryl of the present invention refers to the base that one or more of phenyl molecule aromatic core carbon substitutes to obtain by hetero atom The general name of group, the hetero atom include but is not limited to oxygen, sulphur or nitrogen-atoms, example may include pyridine radicals, pyrimidine radicals, pyrrole radicals, Thienyl, furyl, Evil oxazolyls or triazine radical etc., but not limited to this.
Fused ring heteroaryl of the present invention refers to that one or more of aromatic hydrocarbon molecule aromatic core carbon substitutes to obtain by hetero atom Group general name, the hetero atom includes but is not limited to oxygen, sulphur or nitrogen-atoms, and example may include indyl, quinolyl, isoquinoline Quinoline base, benzothienyl, benzofuranyl, dibenzofuran group, dibenzothiophenes base or carbazyl etc., but not limited to this.
Present invention firstly provides a kind of imidazo azole derivatives, structural formula is：
Wherein, Ar1、Ar2, L independences the substituted or unsubstituted aryl selected from C6~C60, C10~C60 substitution or not Substituted fused ring aryl, C3~C60 substituted or unsubstituted heteroaryl, C9~C60 substituted or unsubstituted condensed ring heteroaryl One kind in base.
Preferably, Ar1、Ar2The substitution of the independent substituted or unsubstituted aryl selected from C6~C25, C10~C20 or not Substituted fused ring aryl, C3~C18 substituted or unsubstituted heteroaryl, C9~C20 substituted or unsubstituted condensed ring heteroaryl One kind in base；L be selected from C6~C20 substituted or unsubstituted aryl, C10~C20 substituted or unsubstituted fused ring aryl, One kind in C9~C20 substituted or unsubstituted fused ring heteroaryl.
According to the present invention, described substituted aryl, substitution five-ring heterocycles, substitution hexa-member heterocycle, substitution it is thick miscellaneous In ring, substituent independence is selected from alkyl, alkoxy, amino, halogen, cyano group, nitro, hydroxyl or sulfydryl.
Preferably, Ar1、Ar2It is independent selected from phenyl, naphthyl, phenanthryl, anthryl, pyrenyl, base, xenyl, terphenyl, Indenyl, indyl, pyridine radicals, pyrimidine radicals, triazine radical, furyl, thienyl, dibenzothiophenes base, dibenzofuran group, quinoline Base, isoquinolyl, phenoxazine base, phenothiazinyl, acridinyl, carbazyl, fluorenyl or the fluorenyl of spiral shell two.
Most preferably L is selected from following structure：
Wherein, R1、R2、R3The independent alkyl selected from C1~C10, C6~C20 substituted or unsubstituted aryl, C10~ One kind in C20 substituted or unsubstituted fused ring aryl.
Any one specifically, a kind of imidazo azole derivatives, in structure as shown below：
A kind of imidazo azole derivatives of the present invention, its preparation method are as follows：
Wherein, Ar1、Ar2, L independences the substituted or unsubstituted aryl selected from C6~C60, C10~C60 substitution or not Substituted fused ring aryl, C3~C60 substituted or unsubstituted heteroaryl, C9~C60 substituted or unsubstituted condensed ring heteroaryl One kind in base.
According to the present invention, the compound shown in structure formula (I) is prepared according to method as follows：
Under nitrogen protection, palladium and tri-butyl phosphine be catalyst, in the case that sodium tert-butoxide is alkali, by secondary amine and Two bromo-derivatives react to obtain intermediate B.
Material a is added in round-bottomed flask, adding toluene makes its dissolving, and unifor is added into solution, After reaction terminates, continue to sequentially add intermediate B and K into reaction solution2CO3, after back flow reaction, reaction solution is cooled to room temperature, It is washed with deionized, organic phase obtains target product (I) through drying, concentration, column chromatography.
The present invention reacts no special limitation to described, is using coupling reaction well-known to those skilled in the art Can, the preparation method is simple, and raw material is easy to get.
The present invention also provides a kind of application of above-mentioned imidazo azole derivatives in an organic light emitting device, and of the invention one Kind imidazo azole derivatives can be applied as hole transport layer material in terms of organic luminescent device, organic hair Optical device includes anode, negative electrode and organic matter layer, and organic matter layer includes hole injection layer, hole transmission layer, electronic barrier layer, hair At least one layer in photosphere, hole blocking layer, electron transfer layer, electron injecting layer；At least one layer in the organic matter layer contains There are a kind of imidazo azole derivatives described above.The organic luminescent device of the present invention be show in flat panel, plane is sent out Body of light, illuminate the light for using face illuminating OLED illuminator, flexible illuminator, duplicator, printer, LCD backlight lamp or dosing machine class Source, display board, mark etc. use.
The present invention has no particular limits to the raw material employed in following examples, can be for commercially available prod or using this Preparation method known to art personnel is prepared.
Embodiment 1：The synthesis of compound 1
(1) sequentially added into round-bottomed flask compound I-1 (21.85g, 73.8mmol), compound II-1 (20.88g, 73.8mmol), t-BuONa (10.7g, 111mmol), Pd (OAc)2(0.33g, 1.47mmol) and the toluene of ultrasonic deoxygenation (1.5L), flowed back liquid under nitrogen protection, and ethyl acetate and water process, and the organic layer that will be obtained are used after the cooling of question response liquid Use MgSO4Dry, decompression boils off solvent, obtains compound III-1 crude product, using silica gel as stationary phase, dichloromethane/hexane is Eluant, eluent, crude product is subjected to column chromatography, obtains compound III-1 (40.58g, 78%).
(2) compound III-1 (35.25g, 50mmol) is added in round-bottomed flask, adding appropriate anhydrous THF makes It dissolves, and at a temperature of -78 DEG C, n-BuLi (4.9ml, 60mmol) is added dropwise into reaction bulb, after reacting 0.5h, to reaction solution Middle fast drop trimethyl borate (11.41g, 75mmol), room temperature is slowly increased to by temperature, continues to react 30min, reaction finishes Afterwards, reaction solution is poured into diluted hydrochloric acid aqueous solution, there is solid matter to separate out filtering, crude product crosses silicagel column and obtains compound IV-1 (11.41g, 75%).
(3) compound V-1 (6.61g, 30mmol) is added in round-bottomed flask, adding toluene makes its dissolving, Xiang Rong Unifor (8.4g, 45mmol) is added in liquid, after reacting 2h under conditions of 80 DEG C, the sequentially adding into reaction solution Compound IV-1 (13.69g, 45mmol) and K2CO3(12.4g, 90mmol), back flow reaction 5h, reaction solution is cooled to room temperature, used Deionized water washing reaction liquid, organic phase obtain compound (9.04g, 67%) through drying, concentration, column chromatography.
Mass spectrum m/z：449.20 (calculated values：449.19).Theoretical elemental content (%) C32H23N3：C,85.50；H,5.16； N, 9.35 actual measurement constituent contents (%)：C,85.51；H,5.15；N,9.35.The above results confirm that it is target product to obtain product.
Embodiment 2：The synthesis of compound 5
Synthetic method according to compound 1 obtains compound 5 (9.93g, 63%).
Mass spectrum m/z：525.23 (calculated values：525.22).Theoretical elemental content (%) C38H27N3：C,86.83；H,5.18； N, 7.99 actual measurement constituent contents (%)：C,86.83；H,5.19；N,7.98.The above results confirm that it is target product to obtain product.
Embodiment 3：The synthesis of compound 8
Synthetic method according to compound 1 obtains compound 8 (10.72g, 65%).
Mass spectrum m/z：549.23 (calculated values：549.22).Theoretical elemental content (%) C40H27N3：C,87.40；H,4.95； N, 7.64 actual measurement constituent contents (%)：C,87.41；H,4.94；N,7.64.The above results confirm that it is target product to obtain product.
Embodiment 4：The synthesis of compound 9
Synthetic method according to compound 1 obtains compound 9 (9.61g, 64%).
Mass spectrum m/z：500.21 (calculated values：500.20).Theoretical elemental content (%) C35H24N4：C,83.98；H,4.83； N, 11.19 actual measurement constituent contents (%)：C,83.98；H,4.82；N,11.20.The above results confirm that obtain product produces for target Product.
Embodiment 5：The synthesis of compound 13
Synthetic method according to compound 1 obtains compound 13 (8.92g, 66%).
Mass spectrum m/z：450.19 (calculated values：450.18).Theoretical elemental content (%) C31H22N4：C,82.64；H,4.92； N, 12.44 actual measurement constituent contents (%)：C,82.64；H,4.91；N,12.45.The above results confirm that obtain product produces for target Product.
Embodiment 6：The synthesis of compound 31
Synthetic method according to compound 1 obtains compound 31 (10.85g, 67%).
Mass spectrum m/z：539.21 (calculated values：539.20).Theoretical elemental content (%) C38H25N3O：C,84.58；H,4.67； N,7.79；O, 2.96 actual measurement constituent contents (%)：C,84.59；H,4.66；N,7.78；O,2.97.The above results confirm to be produced Thing is target product.
Embodiment 7：The synthesis of compound 89
Synthetic method according to compound 1 obtains compound 89 (9.93g, 63%).
Mass spectrum m/z：525.23 (calculated values：525.22).Theoretical elemental content (%) C38H27N3：C,86.83；H,5.18； N, 7.99 actual measurement constituent contents (%)：C,86.83；H,5.19；N,7.98.The above results confirm that it is target product to obtain product.
Embodiment 8：The synthesis of compound 114
Synthetic method according to compound 1 obtains compound 114 (11.13g, 67%).
Mass spectrum m/z：553.26 (calculated values：553.25).Theoretical elemental content (%) C40H31N3：C,86.77；H,5.64； N, 7.59 actual measurement constituent contents (%)：C,86.78；H,5.63；N,7.59.The above results confirm that it is target product to obtain product.
Embodiment 9：The synthesis of compound 115
Synthetic method according to compound 1 obtains compound 115 (12.50g, 69%).
Mass spectrum m/z：603.28 (calculated values：603.27).Theoretical elemental content (%) C44H33N3：C,87.53；H,5.51； N, 6.96 actual measurement constituent contents (%)：C,87.53；H,5.52；N,6.95.The above results confirm that it is target product to obtain product.
Contrast Application Example 1
Ito glass substrate is placed in distilled water and cleaned 2 times, ultrasonic washing 15 minutes is different after distilled water cleaning terminates Ultrasonic washing is dried later in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.Hole injection layer 2- is successively deposited on the ito transparent electrode being already prepared to TNATA/50nm, evaporation hole transmission layer NPB or material of the embodiment of the present invention/30nm, evaporation main body 3Ph-Anthracene：Mix Miscellaneous Ir (tpy)310% mixing/30nm and then evaporation electron transfer layer TPBi/30nm, negative electrode LiF/0.5nm, Al/200nm.
[Application Example 1-9]
By the NPB contrasted in Application Example 1 change into shown compound 1 in Application Example 1-9,5,8,9,13,31, 89、114、115。
Table 1 is compound prepared by the embodiment of the present invention and compares the characteristics of luminescence test of the luminescent device of material preparation As a result.
The characteristics of luminescence test of [table 1] luminescent device
Result above shows that a kind of imidazo azole derivatives of the invention are applied in organic luminescent device, especially As hole transport layer material, the advantages of showing high-luminous-efficiency, long-life, be luminous organic material of good performance.
Obviously, the explanation of above example is only intended to help the method and its core concept for understanding the present invention.It should refer to Go out, under the premise without departing from the principles of the invention, can also be to this hair for the those of ordinary skill of the technical field Bright to carry out some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.

Claims (8)

1. a kind of imidazo azole derivatives, it is characterised in that shown in general structure such as formula (I)：
Wherein, Ar1、Ar2, L independences the substituted or unsubstituted aryl selected from C6~C60, C10~C60 substitution or unsubstituted Fused ring aryl, C3~C60 substituted or unsubstituted heteroaryl, in C9~C60 substituted or unsubstituted fused ring heteroaryl One kind.
A kind of 2. imidazo azole derivatives according to claim 1, it is characterised in that Ar1、Ar2It is independent selected from C6~ C25 substituted or unsubstituted aryl, C10~C20 substituted or unsubstituted fused ring aryl, C3~C18 substitution or do not take One kind in the heteroaryl in generation, C9~C20 substituted or unsubstituted fused ring heteroaryl；L is selected from C6~C20 substitution or not taken The aryl in generation, C10~C20 substituted or unsubstituted fused ring aryl, C9~C20 substituted or unsubstituted fused ring heteroaryl in One kind.
A kind of 3. imidazo azole derivatives according to claim 1, it is characterised in that Ar1、Ar2Independent is selected from benzene Base, naphthyl, phenanthryl, anthryl, pyrenyl, base, xenyl, terphenyl, indenyl, indyl, pyridine radicals, pyrimidine radicals, triazine radical, Furyl, thienyl, dibenzothiophenes base, dibenzofuran group, quinolyl, isoquinolyl, phenoxazine base, phenothiazinyl, a word used for translation Piperidinyl, carbazyl, fluorenyl or the fluorenyl of spiral shell two.
4. a kind of imidazo azole derivatives according to claim 1, it is characterised in that L is selected from following structure：
Wherein, R1、R2、R3The independent alkyl selected from C1~C10, C6~C20 substituted or unsubstituted aryl, C10~C20 Substituted or unsubstituted fused ring aryl in one kind.
A kind of 5. imidazo azole derivatives according to claim 1, it is characterised in that described imidazo pyrrole derivatives Any one of thing in structure as shown below：
6. a kind of organic luminescent device, it is characterised in that the organic luminescent device includes negative electrode, anode and is placed in two electricity One or more organic compound layers between pole, described organic compound layer contain described in claim any one of 1-5 A kind of imidazo azole derivatives.
7. according to a kind of organic luminescent device described in claim 6, it is characterised in that the organic compound layer includes sky Cave implanted layer, hole transmission layer, in electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer extremely It is few one layer；At least one layer is spread out containing a kind of imidazo pyrroles described in claim any one of 1-5 in the organic compound layer Biology.
8. according to a kind of organic luminescent device described in claim 7, it is characterised in that wanted in hole transmission layer containing having the right Seek a kind of imidazo azole derivatives described in 1-5.
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CN110734440A (en) * 2018-07-19 2020-01-31 北京鼎材科技有限公司 imidazole substituted spirofluorene compound and application thereof

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Cited By (6)

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Publication number Priority date Publication date Assignee Title
CN107652286A (en) * 2017-10-25 2018-02-02 长春海谱润斯科技有限公司 A kind of derivative of tri-arylamine group and its organic luminescent device
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CN110734440A (en) * 2018-07-19 2020-01-31 北京鼎材科技有限公司 imidazole substituted spirofluorene compound and application thereof
CN110734440B (en) * 2018-07-19 2022-05-20 北京鼎材科技有限公司 Imidazole-substituted spirofluorene compound and application thereof

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