CN107311925A - One kind contains acridine compounds and its organic luminescent device - Google Patents

One kind contains acridine compounds and its organic luminescent device Download PDF

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CN107311925A
CN107311925A CN201710568879.3A CN201710568879A CN107311925A CN 107311925 A CN107311925 A CN 107311925A CN 201710568879 A CN201710568879 A CN 201710568879A CN 107311925 A CN107311925 A CN 107311925A
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蔡辉
孙可
孙可一
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Changchun Haipurunsi Technology Co Ltd
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Abstract

Contain acridine compounds and its organic luminescent device the invention discloses one kind, the formula of the acridine compounds is：Wherein, L1~L3It is mutual the same or different hydrogen atom, substituted or unsubstituted C6~C60Aryl, substituted or unsubstituted C6~C60Aryl amine, substituted or unsubstituted C5~C60Condensed ring radical, substituted or unsubstituted C5~C60One kind in heterocyclic radical.The present invention's has high luminous efficiency containing acridine compounds.High luminous efficiency shows that the compound can be as electron transport material or light emitting host material, the green motif material of phosphorescence can be especially used as, apply in organic electronic light emitting device, its manufacturing cost is relatively low, the life-span of organic electronic light emitting device is extended, the manufacturing cost of organic electronic light emitting device is reduced.

Description

One kind contains acridine compounds and its organic luminescent device
Technical field
The present invention relates to field of organic electroluminescence, more particularly to a kind of acridine compounds and use prepared by the material having Machine luminescent device.
Background technology
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 (TIL), hole transmission layer (HTL), luminescent layer (EL), hole The negative electrodes such as barrier layer (HBL), electron transfer layer (ETL), electron injecting layer (EIL), LiAl are formed, and 1~2 can be omitted on demand has Machine layer.Voltage is formed between two electrodes of device while from cathode electronics injection, another side anode injects hole.Electronics and sky Cave is in luminescent layer in conjunction with excitation state is formed, and it is luminous that excitation state returns to stable ground state generation.Luminescent material is divided into fluorescent material And phosphor material, the forming method of luminescent layer is the method and fluorescence of doping phosphor material (organic metal) in fluorescent host material The method of material of main part doping fluorescent (organic matter for including nitrogen) dopant.Improvement emission wavelength is mixed by such, efficiency, Driving voltage, the factor such as life-span.It is containing in benzene, naphthalene, fluorenes, the fluorenes of spiral shell two, anthracene, acridine, carbazole etc. to generally form emitting layer material The part such as heart body and benzene, biphenyl, naphthalene, heterocycle；With contraposition, meta, the binding site at ortho position and cyano group, fluorine, methyl, the tert-butyl group etc. Replacing structure.
Maximization is developed into, it is necessary to the finer and smoother and distincter material of color in oled panel, wherein the emphasis solved is Luminous efficiency increase and the life problems of device.General electron mobility degree is slower than hole mobility, in order to which hole and electronics are moved Move speed to be adapted, effective electron-transporting material will be used to improve electron injection and migration blocking unit simultaneously since negative electrode Divide hole movement.The chromaticity coordinates and low driving voltage of another aspect emission wavelength, high efficiency light-emitting efficiency and heat endurance are good High glass transition temperature material be also what industry was badly in need of.
The content of the invention
The present invention develops that synthesis step is simple, the chemical combination of the structure containing acridine of the symmetrically or non-symmetrically structure of excellent performance Thing.And the luminescent device of excellent performance is developed using acridine compounds.
Present invention uses the new acridine compounds that following chemical formula 1 is represented:
[chemical formula 1]
Wherein, L1~L3It is mutual the same or different hydrogen atom, substituted or unsubstituted C6~C60Aryl, substitution or Unsubstituted C6~C60Aryl amine, substituted or unsubstituted C5~C60Condensed ring radical, substituted or unsubstituted C5~C60In heterocyclic radical One kind.
It is preferred that, any one containing acridine compounds in chemical formula 2 below~4：
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
Wherein, R1~R10It is hydrogen atom, substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C1~C60Alkane Epoxide, substituted or unsubstituted C6~C60Aryl, substituted or unsubstituted C5~C60Heterocyclic radical and condensed ring radical；Ar1、Ar2It is substitution Or unsubstituted C6~C60Aryl, substituted or unsubstituted C5~C60Heterocyclic radical and condensed ring radical；Ar5Selected from hydrogen atom, substitution or not Substituted C1~C60Alkyl, substituted or unsubstituted C1~C60Alkoxy, substituted or unsubstituted C1~C60Ether alkyl, substitution or Unsubstituted C6~C60Aryl, substituted or unsubstituted C5~C60Condensed ring radical and heterocyclic radical.
It is preferred that, containing acridine compounds in following chemical formula any one compound：
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 at least one acridine of the present invention Compound.
Beneficial effects of the present invention：
The invention provides high luminescent properties or electronic transmission performance, membrane stability, heat endurance and with high three The compound of weight state energy level.And the organic luminescent device of the compounds of this invention have outstanding electron chemistry and heat endurance and Life-span is outstanding, also has high luminous efficiency in the case where startup voltage is low.
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 is only a part of embodiment of the invention, rather than whole embodiments.Embodiment in the present invention, ordinary skill people The every other embodiment that member is obtained under the premise of creative work is not made, belongs to the scope of protection of the invention.
It should be noted that unless otherwise prescribed, the implication of scientific and technical terminology used in the present invention and people in the art The implication that member is generally understood is identical.
According to the present invention, there is provided a kind of acridine compounds that following chemical formula 1 is represented：
Wherein, L1~L3It is mutual the same or different hydrogen atom, substituted or unsubstituted C6~C60Aryl, substitution or Unsubstituted C6~C60Aryl amine, substituted or unsubstituted C5~C60Condensed ring radical, substituted or unsubstituted C5~C60In heterocyclic radical One kind.
It is preferred that, any one of the acridine compounds in chemical formula 2 below~4：
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
Wherein, A1~A4It is mutual the same or different hydrogen atom, substituted or unsubstituted C6~C60Aryl, substitution or Unsubstituted C5~C60Condensed ring radical, substituted or unsubstituted C5~C60One kind in heterocyclic radical；Ar1And Ar2Or Ar3And Ar4Can be with Form the condensed ring radical and heterocyclic radical of ring structure；Ar5Selected from substituted or unsubstituted hydrogen atom, substituted or unsubstituted C1~C60Alkane Base, substituted or unsubstituted C1~C60Alkoxy, substituted or unsubstituted C1~C60Ether alkyl, substituted or unsubstituted C6~C60 Aryl, substituted or unsubstituted C5~C60Condensed ring radical and heterocyclic radical.
It is preferred that, acridine compounds any one compound in following chemical formula：
The present invention's additionally provides a kind of organic luminescent device, including first electrode, second electrode and is placed in two electricity One or more organic compound layers between pole, it is characterised in that at least one organic compound layer includes at least one originally Invent the organic luminescent device of the new acridine compounds.
Above-mentioned organic matter layer wherein at least includes hole injection layer, hole transmission layer, had both possessed hole injection but also with sky Cave transmission technical ability layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and i.e. possess electronics biography Any one layer in the defeated layer but also with electron injection technical ability.
" organic matter layer " refers to the whole disposed between organic electronic device first electrode and second electrode in this patent The term of layer.
Such as, above-mentioned organic layer includes luminescent layer, and above-mentioned organic layer includes phosphorescence host, fluorescent host, phosphorescence doping And more than one in fluorescence doping, wherein above-mentioned luminescent layer include the above-mentioned new above-mentioned fluorescent hosts of acridine compounds i) can be with It is above-mentioned new acridine compounds ii) doping of above-mentioned fluorescence can be above-mentioned new acridine compounds part iii) above-mentioned fluorescence master It can be above-mentioned new acridine compounds that body and fluorescence, which adulterate,.
Above-mentioned luminescent layer is can also red, yellow or cyan luminescent layer.Such as, it is above-mentioned new during above-mentioned luminescent layer cyan Acridine compounds are used there is provided high efficiency, high brightness, high-resolution and long-life to be had in cyan main body or cyan doping purposes Machine luminescent device.
And above-mentioned organic layer includes electron transfer layer, above-mentioned electron transfer layer includes above-mentioned new amine (Amine) and changed Compound.Wherein above-mentioned electron transfer layer is to include the compound containing other metals beyond above-mentioned new acridine compounds again.
Above-mentioned organic layer all includes luminescent layer and electron transfer layer, and above-mentioned luminescent layer and electron transfer layer each include above-mentioned (above-mentioned luminescent layer and electron transfer layer include above-mentioned new acridine compounds can also be identical for new amine (Amine) compound Can also be different).
Above-mentioned organic electronic device is had using the new acridine compounds and conventional material described in chemical formula 1 and preparation It is prepared by the method for machine electronic device.
Another aspect of the present invention is that above-mentioned device can be used in organic luminescent device (OLED), organic photovoltaic cell (OSC), Electronic Paper (e-Paper), Organophotoreceptor (OPC) or polycrystalline organic thin film
Organic luminescent device utilizes method gold evaporations on substrate such as film vapor deposition, electron beam evaporation, physical vapour deposition (PVD) Category and conductive oxide and their alloy formation anode, its above-mentioned hole injection layer, hole are passed on layer, lighted Layer, hole blocking layer and electron transfer layer, the preparation method of negative electrode are same as above.Cathode substance, organic matter layer, sun are pressed on substrate Pole material order evaporation makes organic luminescent device.
Above-mentioned organic matter layer includes hole injection layer, hole and passes on layer, luminescent layer, hole blocking layer and electron transfer layer etc. Sandwich construction, and above-mentioned organic matter layer substitutes evaporation coating method using various high polymer material solvent engineering, such as and, rotation is applied Film (spin-coating), strip shaping (tape-casting), scraping blade method (doctor-blading), silk-screen printing (Screen-Printing), the method such as ink jet printing or thermal imaging (Thermal-Imaging) reduces number of plies manufacture.
According to the organic assembly of the present invention, the material used can be above luminous, back side illuminated or lighting at two sides.
A kind of acridine compounds of the present invention can use organic photovoltaic cell, illumination OLED, flexibility OLED, organic Organic luminescent device can also be applicable in the organic assemblies such as photoreceptor, organic transistor.
Prompting another aspect of the present invention is to provide above-mentioned new acridine compounds preparation method, but example below below It is to understand that present disclosure is provided, the content of the invention is not limited to this scope.
In addition the manufacture method that the present invention is not introduced specifically is the conventional synthetic method of the industry and implemented with reference to other Example is recorded.
[embodiment 1] compound 2-33 synthesis
* intermediate B -33-1 synthesis
3,6- dibromos acridine (5.69,16.9mmol), anthracene boric acid (3.79g, 17.07mmol), four are added in reaction vessel Triphenylphosphine palladium (0.7g, 1.08mmol), potassium carbonate (5.3g, 38.3mmol), toluene 60mL, ethanol 20mL and distilled water 20mL To stir 3h at 120 DEG C.Distilled water stopping reaction being extracted with ethyl acetate after reaction terminates.Organic layer is dried with MgSO4. Vacuum distillation obtains compound B-33-1 (5.87g, 80%) after removing solvent with silicon gel column purification.
* intermediate B -33-2 synthesis
In reaction vessel add B-33-1 (3.5g, 8.05mmol), 4- dibenzofurans boric acid (3.58g, 16.9mmol), Tetra-triphenylphosphine palladium (0.7g, 1.08mmol), potassium carbonate (5.3g, 38.3mmol), toluene 60mL, ethanol 20mL and distilled water 20mL, stirs 3h at 120 DEG C.Distilled water stopping reaction being extracted with ethyl acetate after reaction terminates.Organic layer is dry with MgSO4 It is dry.Vacuum distillation obtains compound B-33-2 (2.73g, 65%) after removing solvent with silicon gel column purification.
* intermediate B -33-3 synthesis
30mL dichloromethane is added in reactor, B-33-2 (8.81g, 16.9mmol) is then cooled to 0 DEG C, adds NBS (4.51g, 25.35mmol), lucifuge 5h, reaction uses NaHSO after terminating3Washing, removes upper strata solvent, removes layer organic phase dense Contracting, crosses silicagel column and purifies to obtain compound B-33-3 (6.09g, 60%).
* compound 2-33 synthesis
B-33-3 (10.15g, 16.9mmol), phenyl boric acid (2.24g, 18.4mmol), four triphenyls are added in reaction vessel Phosphine palladium (0.7g, 1.08mmol), potassium carbonate (5.3g, 38.3mmol), toluene 60mL, ethanol 20mL and distilled water 20mL, 120 DEG C Lower stirring 3h.Distilled water stopping reaction being extracted with ethyl acetate after reaction terminates.Organic layer MgSO4Dry.Vacuum distillation Remove solvent and obtain compound 2-33 (6.56g, 65%) with silicon gel column purification later.
[embodiment 2] compound 2-42 synthesis
2-42 (6.80g, 68%) is obtained according to 2-33 synthetic methods
[embodiment 3] compound 2-60 is synthesized
2-60 (6.46g, 60%) is obtained according to 2-33 synthetic methods.
[embodiment 4] compound 3-30 synthesis
* intermediate C-30-1 synthesis
HCl (35.0~37.0%, 20mL) is added in reactor and 1,4- dioxanes (120mL) are sufficiently mixed, and is reacted Jia 3 in system, 6- dibromos acridine (15.16g, 45mmol) and paraformaldehyde (4.0g, 113mmol), return stirring 2h.Then it is normal Temperature stirring 16h.Organic layer is separated with dichloromethane after being terminated with water reaction, is dried with MgSO4.Solvent is removed in vacuum distillation, The organic layer bromo- 9-chloroacridines of the isolated compound 3,6- bis- of silica gel column chromatography (14.11g, 84%).
The bromo- 9-chloroacridines (6.76g, 18.2mmol) of 3,6- bis-, DMSO (21mL) are added under condition of nitrogen gas in reaction vessel Stir 30min.Sodium (0.5g, 21.7mmol) is dissolved in ethanol, then adds nitropropane stirring 3h.Obtained material plus DMSO is anti- Answer and 3h is stirred in system.Reaction terminate after be filtrated to get added water in solid matter, filtrate after with dichloromethane extraction and subtract Pressure distillation obtains compound C-30-1 (3.12g, 47%).
* intermediate C-30-2 synthesis
In reaction vessel plus C-30-1 (6.17g, 16.9mmol), 4- dibenzofurans boric acid (3.58g, 17.01mmol), Tetra-triphenylphosphine palladium (0.7g, 1.08mmol), potassium carbonate (5.3g, 38.3mmol), toluene 60mL, ethanol 20mL and distilled water 20mL, stirs 3h at 120 DEG C.Distilled water stopping reaction being extracted with ethyl acetate after reaction terminates.Organic layer is dry with MgSO4 It is dry.Vacuum distillation obtains compound C-30-2 (5.08g, 65%) after removing solvent with silicon gel column purification.
* intermediate C-30-3 synthesis
Two (4- xenyls) amine (29.22g, 59.1mmol), C-30-2 are added under condition of nitrogen gas in reaction vessel The palladium (0.1g) of (27.04g, 58.51mmol), three (dibenzalacetone) two, tri-butyl phosphine (15%, 0.15g), sodium tert-butoxide (0.9g), toluene (400ml) is stirred 12 hours at 60 DEG C.Silica gel filter cone for filtration after reaction solution cooling, two after solution concentration Chloromethanes and hexane carry out column chromatography and obtain compound C-30-3 (27.24g, 68%).
* compound 3-30 synthesis
Under condition of nitrogen gas, 75mL dimethylformamides DMF, C-30-3 (18.48g, 27mmol), Jiao Ya are added in reactor Sodium sulphate (6.16g, 32.4mmol), N- phenyl o-phenylenediamine (4.99g, 27.11mmol), is heated to reflux 5h, after the completion of reaction Aqueous precipitation, through being filled into brown ceramic powder.Methanol washes water removal twice and obtains compound 3-30 (20.86g, 89%).
[embodiment 5] compound 3-78 synthesis
3-78 (20.91,83%) is obtained according to 3-30 synthetic methods.
[embodiment 6] compound 3-96 synthesis
3-96 (20.66g, 78%) is obtained according to 3-30 synthetic methods.
[embodiment 7] compound 4-18 synthesis
* intermediate D-18-1
Obtained according to C-30-1 synthetic methods
* intermediate D-18-2 synthesis
Under condition of nitrogen gas in reaction vessel add carbazole (9.88g, 59.10mmol), C-30-1 (21.35g, 58.51mmol), three (dibenzalacetone) two palladium (0.1g), tri-butyl phosphine (15%, 0.15g), sodium tert-butoxide (0.9g), Stirred 12 hours under toluene (400ml), 60 DEG C of parts.Silica gel filter cone for filtration after reaction solution cooling, dichloromethane after solution concentration Column chromatography, which is carried out, with hexane obtains 4-18 (19.8g, 75%).
* compound 4-18 synthesis
After D-18-2 synthesis, 4-18 (18.51g, 80%) is obtained according to 3-30 synthetic method.
[embodiment 8] compound 4-15 synthesis
4-15 (14.13g, 65%) is obtained according to 4-18 synthetic methods.
[embodiment 9] compound 4-20 synthesis
4-20 (18.61g, 85%) is obtained according to 4-18 synthetic methods.
The FD-MS values of new acridine compound prepared by methods described are that table 1 is represented.
The FD-MS values of new acridine compounds prepared by [table 1]
Compound FD-MS
2-33 M/z=597.21 (C45H27NO=597.72)
2-42 M/z=663.2 (C49H29NS=663.84)
2-60 M/z=709.28 (C55H35N=709.89)
3-30 M/z=867.35 (C64H43N4=868.08)
3-78 M/z=932.38 (C68H46N5=933.15)
3-96 M/z=980.38 (C72H46N5=981.20)
4-18 M/z=856.34 (C62H42N5=857.05)
4-15 M/z=804.31 (C58H38N5=804.98)
4-20 M/z=810.27 (C56H36N5S=811.0)
Device prepares embodiment 1：
It is by Fisher Co., Ltd's coating layer thicknessIto glass substrate be placed in distilled water clean 2 times, ultrasonic wave is washed Wash 30 minutes, cleaned repeatedly with distilled water 2 times, ultrasonic washing 10 minutes, after distilled water cleaning terminates, isopropanol, acetone, first Alcohol equal solvent is dried after ultrasonic washing in order, is transferred in plasma washing machine, and aforesaid substrate is washed 5 minutes, It is sent in evaporator.
Hole injection layer 2-TNATA evaporations will be deposited on the ito transparent electrode being already prepared toHole transmission layer A-NPD (N, N'- bis- (1- naphthyls)-N, N'- diphenyl-(1,1'- biphenyl) -4,4'- diamines) is depositedEmbodiment chemical combination Thing and compare material 3Ph-anthracene ((2,9,10- triphenyls anthracene)) and doping Ir (tpy) 310% evaporationsHole Barrier layer and hole transmission layer TPBiNegative electrode LiFAlSaid process organic matter vaporization plating speed is to maintainLiF isAl is
Table 2 is part of compounds prepared by the embodiment of the present invention and compares the characteristics of luminescence of the luminescent device of material preparation Test result.
The characteristics of luminescence test result of [table 2] luminescent device
From the above-mentioned result of table 2, it is seen that a kind of organic luminescent device luminous efficiency of acridine compounds of the invention and Life characteristic increases significantly.
A kind of acridine compounds of the present invention are applied in organic luminescent device, can obtain luminous efficiency and the life-span is good Organic luminescent device, so the present invention is useful in the high OLED industries of practicality.The present invention organic luminescent device be Flat panel is shown, planar illuminant, illumination face illuminating OLED illuminator, flexible illuminator, duplicator, printer, the LCD back ofs the body Light lamp or the light source of dosing machine class, display board, mark etc. are suitable to be used.

Claims (5)

1. one kind contains acridine compounds, it is characterised in that the Acridine derivatives general molecular formula is：
[chemical formula 1]
Wherein, L1~L3It is mutual the same or different hydrogen atom, substituted or unsubstituted C6~C60Aryl, substitution do not take The C in generation6~C60Aryl amine, substituted or unsubstituted C5~C60Condensed ring radical, substituted or unsubstituted C5~C60One in heterocyclic radical Kind.
2. compound containing acridine according to claim 1, the acridine derivatives that contain are in chemical formula 2 below~4 Any one：
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
Wherein, A1~A4It is mutual the same or different hydrogen atom, substituted or unsubstituted C6~C60Aryl, substitution do not take The C in generation5~C60Condensed ring radical, substituted or unsubstituted C5~C60One kind in heterocyclic radical；Ar1And Ar2Or Ar3And Ar4It can be formed The condensed ring radical and heterocyclic radical of ring structure；Ar5Selected from substituted or unsubstituted hydrogen atom, substituted or unsubstituted C1~C60Alkyl, Substituted or unsubstituted C1~C60Alkoxy, substituted or unsubstituted C1~C60Ether alkyl, substituted or unsubstituted C6~C60Virtue Base, substituted or unsubstituted C5~C60Condensed ring radical and heterocyclic radical.
3. according to claim 1 contain acridine compounds, any one compound in including following chemical formula：
4. a kind of organic luminescent device, including first electrode, second electrode and it is placed in one or more between two electrode Organic compound layer, it is characterised in that at least one organic compound layer is comprising at least one as described in claims 1 to 3 Acridine compounds.
5. a kind of organic luminescent device according to claim 4, it is characterised in that the organic matter layer injects including hole Layer, hole transmission layer and i.e. possess hole injection but also with hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electricity Sub- implanted layer and both possesses electric transmission but also with electron injecting layer, the organic matter layer is comprised at least described in claim 1-3 A kind of new acridine compounds.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110423220A (en) * 2019-06-05 2019-11-08 维思普新材料（苏州）有限公司 A kind of preparation method of 9- phenylacridine class compound

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CN104650032A (en) * 2015-01-23 2015-05-27 北京鼎材科技有限公司 Acridine derivatives, and preparation method and application thereof
KR20160099254A (en) * 2015-02-12 2016-08-22 재단법인대구경북과학기술원 Hole transfer material, inorganic-organic hybrid solar cell using the same, and the manufacturing method thereof
CN106749215A (en) * 2016-12-09 2017-05-31 中节能万润股份有限公司 A kind of compound, preparation method and applications based on monosubstituted base acridine

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104650032A (en) * 2015-01-23 2015-05-27 北京鼎材科技有限公司 Acridine derivatives, and preparation method and application thereof
KR20160099254A (en) * 2015-02-12 2016-08-22 재단법인대구경북과학기술원 Hole transfer material, inorganic-organic hybrid solar cell using the same, and the manufacturing method thereof
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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