CN108264521A - A kind of electroluminescent organic material and its organic luminescent device - Google Patents

A kind of electroluminescent organic material and its organic luminescent device Download PDF

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Publication number
CN108264521A
CN108264521A CN201810061607.9A CN201810061607A CN108264521A CN 108264521 A CN108264521 A CN 108264521A CN 201810061607 A CN201810061607 A CN 201810061607A CN 108264521 A CN108264521 A CN 108264521A
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organic
electroluminescent
aryl
unsubstituted
luminescent device
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孙可
孙可一
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of electroluminescent organic material and organic luminescent device, belongs to organic photoelectrical material technical field.Structure containing pyrene in the structure of electroluminescent organic material provided by the invention by connecting aryl silicon substrate, aryl phosphine oxygroup, aryl sulfuryl group, has effectively interrupted conjugated structure so that triplet higher.Simultaneously, the strong electron withdrawing group contained in the structure of electroluminescent organic material provided by the invention, so that it is with excellent electron transport ability, emitting layer material or electron transport layer materials can be used as to be applied in organic luminescent device, there is higher luminous efficiency and lower driving voltage.

Description

A kind of electroluminescent organic material and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of electroluminescent organic material and its organic hair Optical device.
Background technology
Organic electroluminescent refers to organic material under electric field action, luminous by the excitation of electric current and electric field to show As.Organic electroluminescent LED (OLED) is the display technology of new generation that display is realized using this phenomenon.From U.S. in 1987 State Kodak Company Tang C.W. and Vanslyke S.A. made the organic electroluminescence device of first function admirable with Come, ORGANIC ELECTROLUMINESCENCE DISPLAYS causes the great interest of people since it has the advantage that.
Existing blue phosphor dopant material essentially from German Novaled, Nippon Steel, light extraction Xing Chandeng overseas enterprises, Efficient dark blue luminescent material can not only be substantially reduced the power consumption of display device, be also used as the master of other low energy emissive materials Body material uses, while blue light material is also the indispensable component part for realizing white-light illuminating.But compared to green light and The device level of feux rouges has substantially met practical demand, and the level of blue-light device is lagged, and especially high-performance is deep Blue light material is still more rare, and this is mainly due to because blue light material requires to grip small and higher thermal stability altogether, this two It is conflicting between a requirement is inherent.The mentality of designing of main body blue light material is usually to be conjugated in smaller, plane group Introduce big non-co-planar group.Common core is the preferable anthracene of flatness and fluorenes, and the group for introducing non-co-planar is to subtract The muddy thermal stability to go out and improve amorphous thin film of small condensed light.Such as common Blue-light emitting host material AND, but it shines Performance is unsatisfactory.
Invention content
In view of this, it the purpose of the present invention is to provide a kind of electroluminescent organic material and its organic luminescent device, adopts The organic luminescent device prepared with electroluminescent organic material of the present invention has higher luminous efficiency and lower drive Dynamic voltage.
Present invention firstly provides a kind of electroluminescent organic materials, and general structure is as shown in I：
Wherein, R1、R2Independent is selected from H, substituted or unsubstituted C18-C50 aryl silicon substrate, substituted or unsubstituted C12- One kind in C50 aryl phosphines oxygroup, substituted or unsubstituted C6-C50 aryl sulfuryl, and R1、R2It is asynchronously H.
Preferably, R1、R2Independent is selected from H, substituted or unsubstituted triphenyl silicon substrate, substituted or unsubstituted diphenyl One kind in phosphine oxygroup, substituted or unsubstituted phenyl sulfuryl, and R1、R2It is asynchronously H.
Preferably, the electroluminescent organic material, any one in such as lower structure：
The present invention also provides a kind of organic luminescent device, including first electrode, second electrode and be placed in two electrode it Between one or more organic compound layers, at least one organic compound layer include organic electroluminescence material of the present invention Material.
Preferably, the organic compound layer includes luminescent layer, contains the organic electroluminescent in the luminescent layer Material.
Preferably, the organic compound layer includes electron transfer layer, containing described organic in the electron transfer layer Electroluminescent material.
Beneficial effects of the present invention：
Structure containing pyrene in the structure of electroluminescent organic material provided by the invention, by connecting aryl silicon substrate, virtue Base phosphine oxygroup, aryl sulfuryl group, have effectively interrupted conjugated structure so that triplet higher.Meanwhile the present invention provides Electroluminescent organic material structure in the strong electron withdrawing group that contains so that its with excellent electron transport ability, Emitting layer material or electron transport layer materials can be used as to be applied in organic luminescent device, with higher luminous efficiency and more Low driving voltage.
Specific embodiment
It is clearly and completely described below in conjunction with the technical solution of the embodiment of the present invention, it is clear that described implementation Example is only part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, the common skill in this field Art personnel all other embodiments obtained without making creative work belong to the model that the present invention protects It encloses.
Present invention firstly provides a kind of electroluminescent organic materials, and general structure is as shown in I：
Wherein, R1、R2Independent is selected from H, substituted or unsubstituted C18-C50 aryl silicon substrate, substituted or unsubstituted C12- One kind in C50 aryl phosphines oxygroup, substituted or unsubstituted C6-C50 aryl sulfuryl, and R1、R2It is asynchronously H.
According to the present invention, the aryl silicon substrate refers to what three hydrogen atoms in three sub- silicon substrates of aryl substitution were formed The organic compound of a kind of univalent perssad.
The aryl phosphine oxygroup refers to that phosphono links a kind of univalent perssad being characterized by phosphorus atoms and aryl Organic compound.
The aryl sulfuryl refers to organising for a kind of univalent perssad that sulfonyl is characterized by sulphur with aryl connection Close object.
In heretofore described substituted aryl silicon substrate, the aryl phosphine oxygroup replaced, the aryl sulfuryl replaced, the substitution Base refers to the group that organic compound group removes one or several-H and is formed, such as methyl, ethyl, isopropyl, tertiary butyl, benzene Base, naphthalene, anthryl, phenanthryl, benzo phenanthryl,Base, pyrenyl, fluoranthene base, base, tolyl, methoxyl group, methyl mercapto, phenoxy group, Thiophenyl, fluorenyl, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, hexichol amido, dimethylamino, carbazyl, carbazole diindyl Base, phenyl substituted carbazole base, dibenzofuran group, dibenzothiophene, dibenzo dioxy thienyl, cyano, fluorine-based, deuterium base, Two phenenyl phosphinyl, phenyl sulfuryl, phenylsulfone base, triphenyl silicon substrate, trimethyl silicon substrate, phenothiazinyl, phenoxazine group, acridine Base, dimethyl acridinium, diphenylacridine, dibenzo piperidyl, pyridyl group, pyrimidine radicals, pyridazinyl, pyrazinyl, triazine radical, Evil bis- Oxazolyl, thiadiazolyl group, triazol radical, xenyl, terphenyl, indyl, indenyl, phenanthroline base, nitro etc., but be not limited to This.
Preferably, R1、R2Independent is selected from H, substituted or unsubstituted triphenyl silicon substrate, substituted or unsubstituted diphenyl One kind in phosphine oxygroup, substituted or unsubstituted phenyl sulfuryl, and R1、R2It is asynchronously H.
Any one it is furthermore preferred that electroluminescent organic material, in such as lower structure：
Electroluminescent organic material of the present invention can be prepared by dibromo pyrene by n-BuLi reaction：
Wherein, R1、R2Independent is selected from H, substituted or unsubstituted C18-C50 aryl silicon substrate, substituted or unsubstituted C12- One kind in C50 aryl phosphines oxygroup, substituted or unsubstituted C6-C50 aryl sulfuryl, and R1、R2It is asynchronously H.
The present invention also provides a kind of organic luminescent device, what the organic luminescent device was well known to those skilled in the art Organic luminescent device.Organic luminescent device of the present invention includes first electrode, second electrode and is placed between two electrodes One or more organic compound layers, at least one organic compound layer includes the invention electroluminescent organic material. The organic compound layer includes hole injection layer, hole transmission layer, luminescent layer, hole blocking layer, electron transfer layer and electronics At least one layer in implanted layer contains organic electroluminescence material of the present invention in the preferably described luminescent layer or electron-transport Material.
Embodiment 1：The preparation of compound 1
Step1. 100mmol 2- bromine pyrenes are taken, anhydrous THF dissolvings is added in, cools to -78 DEG C, add in the positive fourth of 1.5 equivalents Base lithium reacts 2 hours at such a temperature, adds in the tri-phenyl chloride of 1 equivalent, is gradually warming up to room temperature, reacts 1 hour.Instead It should add in after the completion, deionized water, organic phase is extracted with EtOAc, organic phase is dry, concentration, crosses column chromatography, obtains product 60mmol.Yield 60%.
Embodiment 2：The preparation of compound 3
Step1. carbazole 100mmol, m-dibromobenzene 100mmol, potassium tert-butoxide 300mmol, Pd are added in reaction vessel2 (dba)31mmol, the dimethylbenzene of ultrasonic deoxygenation, stirring and dissolving, displaced air three times, add in ligand tri-tert phosphorus 4% (4mmol, 50%m/V), again displaced air three times, back flow reaction 6h.It is cooled to room temperature, adds in enough dichloromethane so that producing Product are completely dissolved, and excessively a small amount of silica gel funnel removes catalyst and salt.Filtrate be concentrated into it is thick, cross column chromatography, obtain product 3- 1 80mmol。
Step2. 3-1 80mmol are taken, anhydrous THF dissolvings is added in, cools to -78 DEG C, add in the n-BuLi of 1.5 equivalents, It reacts 2 hours at such a temperature, adds in the diphenyl dichlorosilane of 0.5 equivalent, be gradually warming up to room temperature, react 1 hour.Reaction It adds in after the completion, deionized water, organic phase is extracted with EtOAc, organic phase is dry, concentration, crosses column chromatography, obtains product 3-2 32mmol.Yield 80%.
Step3. 32mmol 2- bromine pyrenes are taken, anhydrous THF dissolvings is added in, cools to -78 DEG C, add in the normal-butyl of 1.5 equivalents Lithium reacts 2 hours at such a temperature, adds in the 3-2 of 1 equivalent, is gradually warming up to room temperature, reacts 1 hour.Add after the completion of reaction Enter, deionized water, organic phase is extracted with EtOAc, organic phase is dry, concentration, crosses column chromatography, obtains product 19.2mmol.Yield 60%.
Embodiment 3：The preparation of compound 19
Step1. carbazole 100mmol, m-dibromobenzene 100mmol, potassium tert-butoxide 300mmol, Pd are added in reaction vessel2 (dba)31mmol, the dimethylbenzene of ultrasonic deoxygenation, stirring and dissolving, displaced air three times, add in ligand tri-tert phosphorus 4% (4mmol, 50%m/V), again displaced air three times, back flow reaction 6h.It is cooled to room temperature, adds in enough dichloromethane so that producing Product are completely dissolved, and excessively a small amount of silica gel funnel removes catalyst and salt.Filtrate be concentrated into it is thick, cross column chromatography, obtain product 19-1 80mmol。
Step2. product 19-1 80mmol, 5% equivalent of cupric sulfate pentahydrate, 5 equivalents of KOH, DMF are added in reaction vessel For solvent, the water of DMF 10% (V) is added in as mixed solvent.After pouring Ar gas, 1, the 2- dithioglycols of 0.55 equivalent are added in, In this Ar displacements three times, it is reacted 24 hours at 120 DEG C.After the completion of reaction, room temperature is cooled to, adds in water, extracted with EtOAC, Washing, dry, concentration, cross silicagel column and obtain product 19-2 50mmol.
Step3. 19-2 50mmol, 2- bromine pyrene 50mmol, potassium tert-butoxide 150mmol, Pd are added in reaction vessel2 (dba)30.5mmol, the dimethylbenzene of ultrasonic deoxygenation, stirring and dissolving, displaced air three times, add in ligand tri-tert phosphorus 4% (2mmol, 50%m/V), again displaced air three times, back flow reaction 6h.It is cooled to room temperature, adds in enough dichloromethane so that producing Product are completely dissolved, and excessively a small amount of silica gel funnel removes catalyst and salt.Filtrate be concentrated into it is thick, cross column chromatography, obtain product 19-3 40mmol。
Step4. 19-3 40mmol are taken, are dissolved in DCM, are cooled to 0 degree Celsius, add in the m-CPBA of 2 equivalents, gradually Room temperature is warming up to, is stirred to react 6 hours, after the completion of reaction, is washed with the anhydrous sodium hydrogensulfite of saturation, organic phase drying is spin-dried for, Obtained product crosses silicagel column, obtains 19 30mmol of target product.
Embodiment 4：The preparation of compound 33
Step1. 100mmol 2- bromine pyrenes are taken, anhydrous THF dissolvings is added in, cools to -78 DEG C, add in the positive fourth of 1.5 equivalents Base lithium reacts 2 hours at such a temperature, adds in the diphenyl phosphorus chloride of 1 equivalent, is gradually warming up to room temperature, reacts 1 hour.Instead It should add in after the completion, deionized water, organic phase is extracted with EtOAc, organic phase is dry, concentration, crosses column chromatography, obtains product 33-1 80mmol.Yield 80%.
Step2. 33-1 80mmol are taken, are dissolved in DCM, are cooled to 0 degree Celsius, add in the m-CPBA of 2 equivalents, gradually Room temperature is warming up to, is stirred to react 6 hours, after the completion of reaction, is washed with the anhydrous sodium hydrogensulfite of saturation, organic phase drying is spin-dried for, Obtained product crosses silicagel column, obtains 33 64mmol of target product.Yield 80%.
Embodiment 5：The preparation of compound 49
Step1. 100mmol 2 is taken, 7- dibromo pyrenes add in anhydrous THF dissolvings, cool to -78 DEG C, add in 2.5 equivalents N-BuLi reacts 2 hours at such a temperature, adds in the tri-phenyl chloride of 2 equivalents, is gradually warming up to room temperature, and reaction 1 is small When.It is added in after the completion of reaction, deionized water, organic phase is extracted with EtOAc, organic phase is dry, concentration, crosses column chromatography, is produced Product 60mmol.Yield 60%.
Embodiment 6：The preparation of compound 54
Step1. 100mmol 2 is taken, 7- dibromo pyrenes add in anhydrous THF dissolvings, cool to -78 DEG C, add in 2.5 equivalents N-BuLi reacts 2 hours at such a temperature, adds in the 54-0 of 2 equivalents, is gradually warming up to room temperature, reacts 1 hour.It has reacted Into rear addition, deionized water, organic phase is extracted with EtOAc, organic phase is dry, concentration, crosses column chromatography, obtains product 54-1 80mmol.Yield 80%.
Step2. 54-1 80mmol are taken, are dissolved in DCM, are cooled to 0 degree Celsius, add in the m-CPBA of 2 equivalents, gradually Room temperature is warming up to, is stirred to react 6 hours, after the completion of reaction, is washed with the anhydrous sodium hydrogensulfite of saturation, organic phase drying is spin-dried for, Obtained product crosses silicagel column, obtains 54 64mmol of target product.Yield 80%.
Compound FD-MS values prepared by 1 embodiment of the present invention of table
Compound FD-MS
1 M/z:40627, C34H24Si (406.16)
3 M/z:625.44, C46H31NSi (625.22)
19 M/z:507.23, C34H21NO2S (507.13)
33 M/z:402.03, C28H19OP (402.12)
49 M/z:718.34, C52H38Si2 (718.25)
54 M/z:754.06, C52H36O2P2 (754.22)
Compare Application Example 1：
Ito glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleans Ultrasonic washing is later dry 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 is deposited successively on the ito transparent electrode being already prepared toHole is deposited Transport layerEmitting layer material AND is deposited:DopantThen vapor deposition electronics passes Defeated layerCathodeAbove process organic matter vaporization plating speed is to maintainLiF It isAl is
Application example 1：
Hole injection layer is deposited successively on the ito transparent electrode being already prepared toHole is deposited to pass Defeated layer NPBEmitting layer material AND is deposited:5% compound of dopantThen electron transfer layer is depositedCathodeAbove process organic matter vaporization plating speed is to maintainLiF isAl is
Application example 2：
Compound 1 in embodiment 1 is changed to compound 3.
Application example 3：
Compound 1 in embodiment 1 is changed to compound 19.
Application example 4：
Compound 1 in embodiment 1 is changed to compound 49.
Measure embodiment 1：The luminescent properties of contrast sample and sample
Contrast sample and sample are using Keithley SMU235, PR650 evaluation luminous efficiencies and driving voltage, knot Fruit is listed in Table 2 below：
The characteristics of luminescence of luminescent device prepared by 2 embodiment of the present invention of table
Compare Application Example 2：
Ito glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleans Ultrasonic washing is later dry 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 TPT-1 is deposited successively on the ito transparent electrode being already prepared toHole is deposited to pass Defeated layer NPBEmitting layer material AND is deposited:DopantThen electron-transport is deposited Layer Alq3CathodeAbove process organic matter vaporization plating speed is to maintainLiF It isAl is
Application example 5：
Hole injection layer TPT-1 is deposited successively on the ito transparent electrode being already prepared toHole is deposited to pass Defeated layer NPBEmitting layer material AND is deposited:DopantThen electron-transport is deposited Layer compound 33CathodeAbove process organic matter vaporization plating speed is to maintain LiF isAl is
Application example 6：
Compound 33 in embodiment 5 is changed to compound 54.
Measure embodiment 2：The luminescent properties of contrast sample and sample
Contrast sample and sample are using Keithley SMU235, PR650 evaluation luminous efficiencies and driving voltage, knot Fruit is listed in Table 3 below：
The characteristics of luminescence of luminescent device prepared by 3 embodiment of the present invention of table
Although the present invention has carried out special description with exemplary embodiment, but it is understood that without departing from claim In the case of the spirit and scope of the invention limited, those of ordinary skill in the art can carry out various forms and details to it On change.

Claims (6)

1. a kind of electroluminescent organic material, general structure is as shown in I：
Wherein, R1、R2Independent is selected from H, substituted or unsubstituted C18-C50 aryl silicon substrate, substituted or unsubstituted C12-C50 One kind in aryl phosphine oxygroup, substituted or unsubstituted C6-C50 aryl sulfuryl, and R1、R2It is asynchronously H.
A kind of 2. electroluminescent organic material according to claim 1, which is characterized in that R1、R2Independent is selected from H, substitution Or one in unsubstituted triphenyl silicon substrate, substituted or unsubstituted diphenylphosphine oxygroup, substituted or unsubstituted phenyl sulfuryl Kind, and R1、R2It is asynchronously H.
3. a kind of electroluminescent organic material according to claim 1, which is characterized in that arbitrary in such as lower structure It is a kind of：
4. a kind of organic luminescent device, including first electrode, second electrode and the one or more being placed between two electrode Organic compound layer, which is characterized in that at least one organic compound layer contains having as described in claim any one of 1-3 Electroluminescent material.
5. a kind of organic luminescent device according to claim 4, which is characterized in that the organic compound layer includes shining Layer, the electroluminescent organic material as described in claim any one of 1-3 is contained in the luminescent layer.
6. a kind of organic luminescent device according to claim 4, which is characterized in that the organic compound layer includes electronics Transport layer contains the electroluminescent organic material as described in claim any one of 1-3 in the electron transfer layer.
CN201810061607.9A 2018-01-18 2018-01-18 A kind of electroluminescent organic material and its organic luminescent device Withdrawn CN108264521A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111793028A (en) * 2019-04-05 2020-10-20 三星显示有限公司 Organic electroluminescent device and compound for organic electroluminescent device
CN113416329A (en) * 2021-05-28 2021-09-21 南京邮电大学 Preparation method and application of high-temperature multi-threshold temperature indicating film with fluorescence changing in multiple colors visible to naked eyes
CN113667123A (en) * 2021-09-10 2021-11-19 中鼎凯瑞科技成都有限公司 Polyarylene sulfide compound with ultraviolet fluorescent tracing function and preparation method thereof

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111793028A (en) * 2019-04-05 2020-10-20 三星显示有限公司 Organic electroluminescent device and compound for organic electroluminescent device
US11844274B2 (en) 2019-04-05 2023-12-12 Samsung Display Co., Ltd. Organic electroluminescence device and compound for organic electroluminescence device
CN113416329A (en) * 2021-05-28 2021-09-21 南京邮电大学 Preparation method and application of high-temperature multi-threshold temperature indicating film with fluorescence changing in multiple colors visible to naked eyes
CN113416329B (en) * 2021-05-28 2022-03-11 南京邮电大学 Preparation method and application of high-temperature multi-threshold temperature indicating film with fluorescence changing in multiple colors visible to naked eyes
CN113667123A (en) * 2021-09-10 2021-11-19 中鼎凯瑞科技成都有限公司 Polyarylene sulfide compound with ultraviolet fluorescent tracing function and preparation method thereof
CN113667123B (en) * 2021-09-10 2023-11-07 中鼎凯瑞科技成都有限公司 Polyarylene sulfide compound with ultraviolet fluorescence tracing function and preparation method thereof

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