CN107056798A - A kind of thiophene or furan derivatives and the organic luminescent device using the derivative - Google Patents

A kind of thiophene or furan derivatives and the organic luminescent device using the derivative Download PDF

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CN107056798A
CN107056798A CN201710445149.4A CN201710445149A CN107056798A CN 107056798 A CN107056798 A CN 107056798A CN 201710445149 A CN201710445149 A CN 201710445149A CN 107056798 A CN107056798 A CN 107056798A
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unsubstituted
thiophene
layer
substituted
furan derivatives
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董秀芹
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The invention discloses a kind of thiophene or furan derivatives and using the organic luminescent device of the derivative, belong to organic photoelectrical material technical field.The derivative of the present invention is with thieno [3,2 b] thiophene, furans simultaneously [3,2 b] furans or thieno [3,2 b] thiophene 1,1,4,4 tetroxides are agent structure, by the on-link mode (OLM) for changing donor, molecular weight, pi-conjugated property and the electrophilicity of material, charge transport ability and photochromic etc. can be adjusted, and can effectively solve the problem that the unbalanced problem of unipolarity luminescent material carrier so that thiophene or furan derivatives of the invention has high luminescent properties and electronic transmission performance, membrane stability, heat endurance and with high triplet energy level.The features such as organic luminescent device prepared using the thiophene or furan derivatives of the present invention has outstanding electron chemistry and heat endurance and outstanding life-span, start voltage it is low in the case of also there is high luminous efficiency.

Description

A kind of thiophene or furan derivatives and the organic luminescent device using the derivative
Technical field
The present invention relates to organic photoelectrical material technical field, more particularly to a kind of thiophene or furan derivatives and spread out using this Biological organic luminescent device.
Background technology
U.S. Kodak Company Tang C.W and Vanslyke S.A is used as luminous material using 8-hydroxyquinoline aluminium within 1987 Material, the organic bilayer film electroluminescent device of first function admirable is prepared using sandwich structure, so that having evoked has The research boom of electroluminescent material and device, by the development of nearly 30 years, organic electroluminescent LED was imaged As Display Technique of new generation most with prospects, its have from main light emission, low-voltage direct-current driving, all solidstate, visual angle it is wide, Lightweight, composition and a series of advantage such as technique is simple, compared with liquid crystal display, display of organic electroluminescence need not Backlight, visual angle is big, and power is low, and its response speed is up to 1000 times of liquid crystal display, and its manufacturing cost is but less than same decile The liquid crystal display of resolution, therefore, organic electroluminescence device has broad application prospects.
General organic luminescent device (OLED) is the organic matter layer structure inserted between negative electrode, anode and negative electrode and anode Into, the composition of device is transparent ITO anode, hole injection layer (HIL), hole transmission layer (HTL), luminescent layer (EL), hole The negative electrodes such as barrier layer (HBL), electron transfer layer (ETL), electron injecting layer (EIL), Li/Al are formed, on demand can clipped Organic layer.Voltage is formed between two electrodes of device, while injecting electronics, another side anode injection hole from negative electrode.Electronics With hole in luminescent layer in conjunction with excitation state is formed, excitation state returns to stable ground state, so as to realize luminous.In practical application In, hole or electron-transporting type material of main part doping guest emitting material formation luminescent layer, but hole and electronics are each organic Transmission speed in layer is different, causes the two on deviation one side of luminescent layer recombination region meeting selectivity, so as to cause device Efficiency, photochromic, stability change, even more serious situation then can cause the energy between triplet to be quenched, so as to cause effect Rate is roll-offed seriously, so as to influence the service life and stability of device.
Following OLED direction is to develop high efficiency, high brightness, long-life, the white light parts and full-color EL display of low cost Device.Oled panel, which is shown, develops into maximization, it is necessary to the finer and smoother and distincter material of color, wherein the emphasis solved is hair It is round and smooth that light efficiency increase and the life problems of device, this hole being accomplished by luminescent layer and electronics combine progress.But general electricity Transport factor is slower than hole mobility, in order to which hole and Electronic Circle Slipped Clove Hitch are closed it is necessary to use effective electron-transporting material, from the moon Pole starts to improve electron injection and migration, while cut-off parts hole is moved.
The content of the invention
It is an object of the invention to provide a kind of thiophene or furan derivatives and using the organic luminescent device of the derivative, Derivative of the present invention is with thieno [3,2-b] thiophene, furans simultaneously [3,2-b] furans or thieno [3,2-b] thiophene 1,1,4,4- Tetroxide is core, by connecting different groups, so as to adjust the molecular weight of material, pi-conjugated property and electrophilicity, electric charge transmission energy Power, can effectively solve the unbalanced problem of unipolarity luminescent material carrier, so as to improve the efficiency of device and its photochromic Stability.
Contain thiophene or furan derivatives the invention provides one kind, its structural formula is as follows：
[chemical formula 1]
Any one representation in the chemical formula 1, such as following chemical formula 2- chemical formulas 4：
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
Wherein, R1~R4Selected from hydrogen atom, substituted or unsubstituted C1-C40Alkyl, substituted or unsubstituted C6-C60Virtue Base, substituted or unsubstituted C10-C60Condensed ring radical, substituted or unsubstituted C8-C60Condensed hetero ring base, substituted or unsubstituted C5-C60 Heterocyclic radical in one kind, R1-R4Structure can be identical, also can be different.
It is preferred that, R1-R4Selected from hydrogen atom, substituted or unsubstituted C1-C20Alkyl, substituted or unsubstituted C6-C30Virtue Base, substituted or unsubstituted C10-C30Condensed ring radical, substituted or unsubstituted C8-C30Condensed hetero ring base, substituted or unsubstituted C5-C30 Heterocyclic radical in one kind, R1~R4Structure can be identical, also can be different.
Further preferably, R1~R4Selected from hydrogen atom, substituted or unsubstituted C2-C12Alkyl, substituted or unsubstituted C6-C24 Aryl, substituted or unsubstituted C10-C20Condensed ring radical, substituted or unsubstituted C8-C20Condensed hetero ring base, substituted or unsubstituted C5- C14Heterocyclic radical in one kind, R1-R4Structure can be identical, also can be different.
Further preferably, thiophene or furan derivatives provided by the present invention are any one in chemical constitution as follows Kind：
Present invention also offers a kind of organic luminescent device, including anode, negative electrode and be placed between two electrode one Individual or multiple organic compound layers, it is characterised in that the organic compound layer includes hole injection layer, hole transmission layer, electricity At least one layer in sub- barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer；The organic compound layer In at least one layer contain thiophene of the present invention or furan derivatives.
It is preferred that, the organic luminescent device can be applied to organic photovoltaic cell, Electronic Paper, Organophotoreceptor or organic Field of thin film transistors.
Beneficial effects of the present invention：
The present invention provides a kind of thiophene or furan derivatives, with thieno [3,2-b] thiophene, furans simultaneously [3,2-b] furans, Or thieno [3,2-b] thiophene 1, Isosorbide-5-Nitrae, 4- tetroxides are agent structure, by changing the on-link mode (OLM) of donor, can be adjusted The molecular weight of material, pi-conjugated property and electrophilicity, charge transport ability and photochromic etc., and can effectively solve the problem that unipolarity lights material Expect the unbalanced problem of carrier so that thiophene or furan derivatives of the invention has high luminescent properties and electron-transporting Energy, membrane stability, heat endurance and with high triplet energy level.Using prepared by the thiophene or furan derivatives of the present invention having The features such as machine luminescent device has outstanding electron chemistry and heat endurance and outstanding life-span, start voltage it is low in the case of With high luminous efficiency.
Embodiment：
Technical scheme below in conjunction with the embodiment of the present invention is clearly and completely described, it is clear that described implementation Example only a part of embodiment of the invention, rather than whole embodiments.Based on the embodiment in the present invention, art technology The every other embodiment that personnel obtain under the premise of creative work is not made, belongs to the scope of protection of the invention.
The present invention provides a kind of thiophene or furan derivatives that following chemical formula 1 is represented：
[chemical formula 1]
Any one representation in the chemical formula 1, such as following chemical formula 2- chemical formulas 4：
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
Wherein, R1~R4Selected from hydrogen atom, substituted or unsubstituted C1-C40Alkyl, substituted or unsubstituted C6-C60Virtue Base, substituted or unsubstituted C10-C60Condensed ring radical, substituted or unsubstituted C8-C60Condensed hetero ring base, substituted or unsubstituted C5-C60 Heterocyclic radical in one kind, R1-R4Structure can be identical, also can be different.
According to the present invention, the substituted alkyl, the aryl of substitution, the condensed ring radical of substitution, the condensed hetero ring base of substitution, substitution Heterocyclic radical in, the substituent may be selected from deuterium, C1-C10 alkyl, halogen, cyano group or nitro, preferably deuterium, C1-C4 alkyl, Fluorine or cyano group, more preferably cyano group.In the condensed hetero ring base or heterocyclic radical, the hetero atom is preferably N, O or S.
It is preferred that the R1-R4Selected from hydrogen atom, substituted or unsubstituted C1-C20Alkyl, substituted or unsubstituted C6-C30 Aryl, substituted or unsubstituted C10-C30Condensed ring radical, substituted or unsubstituted C8-C30Condensed hetero ring base, substituted or unsubstituted C5- C30Heterocyclic radical in one kind, R1~R4Structure can be identical, also can be different.More preferably described R1~R4Selected from hydrogen atom, substitution Or unsubstituted C2-C12Alkyl, substituted or unsubstituted C6-C24Aryl, substituted or unsubstituted C10-C20Condensed ring radical, substitution Or unsubstituted C8-C20Condensed hetero ring base, substituted or unsubstituted C5-C14Heterocyclic radical in one kind, R1-R4Structure can be identical, Also can be different.
As an example, it is not particularly limited, thiophene or furan derivatives of the present invention may be selected from chemistry as follows Any one in structure：
It is enumerated above some concrete structures of thiophene of the present invention or furan derivatives, but thiophene of the present invention Or furan derivatives are not limited to these listed chemical constitutions, every based on structure shown in chemical formula 1-4, R1-R4For Group as defined above is included in this patent protection domain.
The preparation method of thiophene or furan derivatives shown in chemical formula 1 of the present invention, can be by by the compound shown in formula A Prepared by bromination, Suzuki coupling reactions and oxidation reaction, such as when the furans shown in chemical formula 1 or thiophene derive , can be by the way that the compound shown in formula A be passed through into bromination, Suzuki coupling reactions when thing is structure shown in chemical formula 2 or chemical formula 3 Prepare, can be by by the institute of chemical formula 3 when the furans or thiophene derivant shown in chemical formula 1 are structure shown in chemical formula 4 The compound shown is prepared through peroxidization again.
The present invention does not have particular/special requirement to the reaction condition of above-mentioned all kinds of reactions, is well known to those skilled in the art such The normal condition of reaction, wherein R1、R2、R3、R4Selection with described above, will not be repeated here.
Present invention also offers a kind of organic luminescent device, including anode, negative electrode and be placed between two electrode one Individual or multiple organic compound layers, the organic matter layer comprising hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, At least one layer in hole blocking layer, electron transfer layer, electron injecting layer；At least one layer in the organic compound layer contains Thiophene or furan derivatives of the present invention.
Thiophene or furan derivatives of the present invention can be contained in singular form or with other material mixing forms In above-mentioned organic compound layer.
It is preferred that, thiophene or furan derivatives of the present invention can be used as the fluorescence master in organic luminescent device luminescent layer Body material, fluorescence dopant material or alone as luminescent layer, more preferably as luminescent layer fluorescence dopant material.
It is preferred that, thiophene or furan derivatives of the present invention are alternatively arranged as the electron transfer layer material of organic luminescent device Material or electron injecting layer material, more preferably as electron transport layer materials.
Organic luminescent device of the present invention can be applied to organic photovoltaic cell, Electronic Paper, Organophotoreceptor or organic thin Film transistor field.
[embodiment 1] compound 3-1 synthesis
* intermediate C-1-1 synthesis
Thieno [3,2-b] thiophene (4.21g, 30mmol) is put into reactor, under nitrogen protection, second is added in reactor Sour 30ml, chloroform 50ml, by 20mmol Br2It is slowly dropped into reactor and reacts, 1h is stirred afterwards, then be gradually added 15mmol's Br2, 1h is stirred, flows back a night, is cooled to room temperature, solid precipitation is obtained, is successively washed with deionized water and methanol, dry, obtain To crude product cross silicagel column, obtain compound C-1-1 (12.72g, 93%).
* compound 3-1 synthesis
In reaction vessel plus C-1-1 (1.91g, 4.2mmol), (4- cyano-phenyls) boric acid (2.5g, 18.4mmol), four or three Phenylphosphine palladium (0.7g, 1.08mmol), potassium carbonate (5.3g, 38.3mmol), toluene 60mL, ethanol 20mL and distilled water 20mL with 3h is stirred under the conditions of 120 DEG C afterwards.Distilled water stops reaction after reaction terminates, and is extracted with ethyl acetate.Organic layer MgSO4It is dry It is dry.Vacuum distillation obtains compound 3-1 (1.56g, 68%) after removing solvent with silicon gel column purification.
[embodiment 2] compound 3-21 synthesis
* intermediate C-21-1 synthesis
30mlDMF is added in reactor, thieno [3,2-b] thiophene (2.31g, 16.5mmol) is then cooled to 0 DEG C, NBS (8.81g, 49.5mmol) is added, lucifuge reaction 12h, reaction uses NaHSO after terminating3Washing, removes upper strata solvent, removes Layer organic phase concentration, crosses silicagel column and purifies to obtain compound C-21-1 (4.67g, 95%).
* compound 3-21 synthesis
Add C-21-1 (2.5g, 8.4mmol), anthracene boric acid (3.79g, 17.07mmol), tetra-triphenylphosphine palladium in reaction vessel 120 DEG C after (0.7g, 1.08mmol), potassium carbonate (5.3g, 38.3mmol), toluene 60mL, ethanol 20mL and distilled water 20mL Under the conditions of stir 3h.Distilled water stops reaction after reaction terminates, and is extracted with ethyl acetate.Organic layer MgSO4Dry.Decompression Distillation obtains compound 3-21 (3.23g, 78%) after removing solvent with silicon gel column purification.
[embodiment 3] compound 3-28 synthesis
* intermediate C-28-1 synthesis
Addition C-1-1 (9.12g, 20mmol) in reactor, acetic acid 500ml, toluene 200ml, Zn powder (2.62g, 40mmol), hydrochloric acid solution is slowly dropped into course of reaction, excites Zn powder activity, question response terminates, and flows back a night, then cooling To room temperature, solution is concentrated, is filtrated to get compound C-28-1 (5.36g, 90%).* intermediate C-28-2 synthesis
Add C-28-1 (2.5g, 8.4mmol), luxuriant and rich with fragrance boric acid (3.79g, 17.07mmol), tetra-triphenylphosphine palladium in reaction vessel 120 DEG C after (0.7g, 1.08mmol), potassium carbonate (5.3g, 38.3mmol), toluene 60mL, ethanol 20mL and distilled water 20mL Under the conditions of stir 3h.Distilled water stops reaction after reaction terminates, and is extracted with ethyl acetate.Organic layer MgSO4Dry.Decompression Distillation obtains compound C-28-2 (3.1g, 75%) after removing solvent with silicon gel column purification.
* compound C-28-3 synthesis
30mlDMF, C-28-2 (8.13g, 16.5mmol) are added in reactor, 0 DEG C is then cooled to, NBS is added (8.81g, 49.5mmol), lucifuge reaction 12h, reaction uses NaHSO after terminating3Washing, removes upper strata solvent, removes a layer organic phase Concentration, crosses silicagel column and purifies to obtain compound C-28-3 (9.87g, 92%).* compound 3-28 synthesis
In reaction vessel plus C-28-3 (5.46g, 8.4mmol), positive third borine (0.95g, 6.76mmol) be dissolved in toluene, The mixed solvent of ethanol water, adds potassium phosphate (10.76g, 50.7mmol) 3 equivalent, and nitrogen protection is lower to add catalyst Pd (OAc)2(0.19g, 0.85mmol), add under the conditions of part 0.17mmol, 100 DEG C and stir 6h.Reaction is added after terminating Distilled water, stops reaction, is extracted with ethyl acetate.Organic layer MgSO4Dry.Vacuum distillation uses silicagel column after removing solvent Son purification obtains compound 3-28 (4.41g, 91%).
[embodiment 4] compound 4-1 synthesis
Under argon gas protection, by 20ml H2O2Slowly it is added drop-wise to 3-1 (8.4mmol) acetic acid (60ml) and DCM (25ml) In the mixed solvent.Reaction system is reacted after 1h at room temperature, is heated to 90 DEG C, reacts 36h, and the head product of reactant is extracted with DCM After taking, white solid (2.61g, 51%) is obtained by post separation.
Thiophene or the FD-MS values of furan derivatives prepared by the embodiment of the present invention is as shown in table 1.
【Table 1】Thiophene or the FD-MS values of furan derivatives prepared by the embodiment of the present invention
[embodiment 5] device prepares embodiment：
The glass substrate for being coated with transparent conductive layer is placed on sonic washing in cleaning agent, 3 are cleaned repeatedly with distilled water Secondary, after distilled water cleaning terminates, the ultrasonic washing in acetone, alcohol mixed solution is dried remove moisture afterwards, retransfers afterwards Wash, the ito substrate after processing is put into evaporator in plasma washing machine then.It is deposited in the following order：Hole Implanted layer 2-TNATA, thickness 50nm；Hole transmission layer a-NPD, thickness 30nm；Luminescent layer material of main part AND and dopant DPAP-DPPA or embodiments of the invention material (5%), luminescent layer evaporation film gross thickness are 30nm；Then hole barrier is deposited Layer and electron transfer layer TPBi, thickness 40nm；Negative electrode LiF, thickness 0.5nm, metal Al, thickness 60nm.
Table 2 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.
[table 2]
Result above shows that thiophene of the invention or furan derivatives are applied in organic luminescent device, especially as Luminescent layer doping guest materials, the luminous efficiency of its organic luminescent device is significantly increased, and thiophene of the invention or furans derive Thing is luminous organic material of good performance.
It should be pointed out that the present invention is particularly described with individual embodiments, but before the principle of the invention is not departed from Put, ordinary skill people can carry out the improvement on various forms or details to the present invention, these improvement also fall into this hair In bright protection domain.

Claims (6)

1. a kind of thiophene or furan derivatives, with structure shown in chemical formula 1：
[chemical formula 1]
Any one representation in the chemical formula 1, such as following chemical formula 2- chemical formulas 4：
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
Wherein, R1-R4Selected from hydrogen atom, substituted or unsubstituted C1-C40Alkyl, substituted or unsubstituted C6-C60Aryl, take Generation or unsubstituted C10-C60Condensed ring radical, substituted or unsubstituted C8-C60Condensed hetero ring base, substituted or unsubstituted C5-C60It is miscellaneous One kind in ring group, R1-R4Structure can be identical, also can be different.
2. a kind of thiophene according to claim 1 or furan derivatives, it is characterised in that R1-R4Selected from hydrogen atom, substitution Or unsubstituted C1-C20Alkyl, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C10-C30Condensed ring radical, substitution Or unsubstituted C8-C30Condensed hetero ring base, substituted or unsubstituted C5-C30Heterocyclic radical in one kind, R1-R4Structure can be identical, Also can be different.
3. a kind of thiophene according to claim 1 or furan derivatives, it is characterised in that R1-R4Selected from hydrogen atom, substitution Or unsubstituted C2-C12Alkyl, substituted or unsubstituted C6-C24Aryl, substituted or unsubstituted C10-C20Condensed ring radical, substitution Or unsubstituted C8-C20Condensed hetero ring base, substituted or unsubstituted C5-C14Heterocyclic radical in one kind, R1-R4Structure can be identical, Also can be different.
4. a kind of thiophene according to claim 1 or furan derivatives, it is characterised in that the thiophene or furan derivatives Any one in chemical constitution as follows：
5. a kind of organic luminescent device, including anode, negative electrode and one or more organic compounds for being placed between two electrode Nitride layer, it is characterised in that the organic compound layer comprising hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, At least one layer in hole blocking layer, electron transfer layer, electron injecting layer；At least one layer in the organic compound layer contains Any thiophene or furan derivatives described in claim 1-4 any one.
6. organic luminescent device according to claim 5, it is characterised in that the organic luminescent device can be applied to organic Solar cell, Electronic Paper, Organophotoreceptor or OTFT field.
CN201710445149.4A 2017-06-13 2017-06-13 A kind of thiophene or furan derivatives and the organic luminescent device using the derivative Withdrawn CN107056798A (en)

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Publication number Priority date Publication date Assignee Title
CN110818727A (en) * 2018-08-10 2020-02-21 上海和辉光电有限公司 Thermal activation delayed fluorescent material, preparation method and application thereof, and OLED device comprising thermal activation delayed fluorescent material
CN112542553A (en) * 2019-09-20 2021-03-23 Tcl集团股份有限公司 Compound and preparation method thereof and quantum dot light-emitting diode
CN111377943A (en) * 2020-03-31 2020-07-07 烟台显华化工科技有限公司 Quinary heterocyclic organic compound and application thereof
CN112409374A (en) * 2020-11-20 2021-02-26 四川师范大学 Preparation method of rigid core direct-connected graphene-like benzophenanthrene discotic liquid crystal and mesomorphism
CN114644610A (en) * 2020-12-17 2022-06-21 上海和辉光电股份有限公司 Organic light-emitting material, manufacturing method thereof and OLED device

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