CN107235898A - A kind of acridine compounds and organic luminescent device - Google Patents

A kind of acridine compounds and organic luminescent device Download PDF

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CN107235898A
CN107235898A CN201710568878.9A CN201710568878A CN107235898A CN 107235898 A CN107235898 A CN 107235898A CN 201710568878 A CN201710568878 A CN 201710568878A CN 107235898 A CN107235898 A CN 107235898A
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chemical formula
acridine compounds
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蔡辉
刘喜庆
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Changchun Haipurunsi Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The invention discloses a kind of acridine compounds and its organic luminescent device.The Acridine derivatives of the present invention have high luminous efficiency.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

A kind of acridine compounds and organic luminescent device
Technical field
The present invention relates to field of organic electroluminescence, more particularly to a kind of acridine compounds and organic 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 acridine compounds that following chemical formula 1 is represented:
[chemical formula 1]
It is preferred that, the acridine compounds are selected from any one in following chemical formula [2~4]：
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
Ar1~Ar4It is mutual the same or different substituted or unsubstituted hydrogen atom, substituted or unsubstituted C6~C60 Aryl, substituted or unsubstituted C5~C60Condensed ring radical or heterocyclic radical；Ar1 and Ar2 or Ar3 and Ar4 can form the structure of ring Condensed ring radical or heterocyclic radical；Ar5Selected from hydrogen atom, substituted or unsubstituted C1~C60Alkyl, substituted or unsubstituted C1~C60Alkane Epoxide, substituted or unsubstituted C1~C60Ether alkyl, substituted or unsubstituted C6~C60Aryl, substituted or unsubstituted C5~C60 Condensed ring radical or heterocyclic radical.
It is preferred that, acridine compounds any one compound in following chemical formula：
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 only a part of embodiment of the invention, rather than whole embodiments.
By the present invention, there is provided the acridine compounds that following chemical formula 1 is represented：
[chemical formula 1]
It is preferred that, any one being selected from containing acridine derivatives in following chemical formula [2~4].
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
Ar1~Ar4It is mutual the same or different substituted or unsubstituted hydrogen atom, substituted or unsubstituted C6~C60 Aryl, substituted or unsubstituted C5~C60Condensed ring radical or heterocyclic radical；Ar1 and Ar2 or Ar3 and Ar4 can form the thick of ring structure Ring group or heterocyclic radical；A5Selected from hydrogen atom, substituted or unsubstituted C1~C60Alkyl, substituted or unsubstituted C1~C60Alcoxyl Base, substituted or unsubstituted C1~C60Ether alkyl, substituted or unsubstituted C6~C60Aryl, substituted or unsubstituted C5~C60It is thick Ring group or heterocyclic radical.
It is preferred that, acridine compounds any one compound in following chemical formula：
Present invention also offers a kind of organic luminescent device, including first electrode, second electrode and it is placed in two electrode Between one or more organic compound layers, at least one organic compound layer include at least one acridine of the present invention Compound.
Above-mentioned organic matter layer wherein at least includes hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole At least one layer in barrier layer, electron transfer layer, electron injecting layer.
The above-mentioned device of the present invention can be used in organic luminescent device (OLED), organic photovoltaic cell (OSC), Electronic Paper (e- Paper), Organophotoreceptor (OPC) or OTFT field.
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.
It is below the preparation method of above-mentioned acridine compounds of the invention, but example below is to understand present disclosure There 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.
The 2-15 synthesis of [embodiment 1] compound
* intermediate B -15-1 synthesis
Acridine (3.59g, 20mmol) is added in reaction vessel, solvent concentrated sulfuric acid 30mL, stirring and dissolving is cooled to 0 DEG C of left side Concentrated nitric acid 50mmol is slowly added dropwise under the right side, stirring, control temperature does not surpass 5 DEG C, reacts 2h.After the completion of add frozen water, extracted with toluene Crude product is obtained, crude product crosses silicagel column, obtain 2,7- dinitros acridine (2.69g, 50%).
2,7- dinitros acridine (5.38g, 20mmol), absolute ethyl alcohol, and appropriate palladium-carbon catalyst are added in reaction vessel, In a hydrogen atmosphere, 24h is reacted at room temperature.Celite pillars are crossed after the completion of reaction.It is spin-dried for solvent and obtains 2,7- proflavins (3.8g, 93%).
The NaNO of 1.1 equivalents is added in there-necked flask with thermometer2, the concentrated sulfuric acid, nitrogen protection under cool to 2 DEG C.Will 2,7- proflavins (3.14g, 15mmol) dissolve in glacial acetic acid, are slowly dropped in above-mentioned mixed liquor, then at 5-8 DEG C React 2h.Then -5 DEG C are cooled to, a large amount of ether are added, continues to stir 25min at -5 DEG C.Filtering, obtained filter cake ether Washing.Obtained solid is added in the CuBr and 48% HBr aqueous solution at room temperature, and flow back 2h at 64 DEG C, obtained solid mistake Filter, is washed with deionized, and dries.Obtained crude product crosses silicagel column, obtains compound B-15-1 (2.67g, 85%).
* intermediate B -15-2 synthesis
In reaction vessel plus N- phenyl -3- carbazoles boric acid (4.85g, 16.9mmol), B-15-1 (2.71g, 8.05mmol), 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-15-2 (5.49g, 65%) after removing solvent with silicon gel column purification.
* intermediate B -15-3 synthesis
Add B-15-2 (8.44g, 16.9mmol), anthracene boric acid (3.79g, 17.07mmol), four triphenylphosphines in reaction vessel Palladium (0.7g, 1.08mmol), potassium carbonate (5.3g, 38.3mmol), toluene 60mL, ethanol 20mL and distilled water 20mL, at 120 DEG C Stir 3h.Distilled water stopping reaction being extracted with ethyl acetate after reaction terminates.Organic layer is dried with MgSO4.Vacuum distillation is gone Fall solvent and obtain compound 2-15 (8.07g, 80%) with silicon gel column purification later.
* intermediate B -15-4 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 (6.85g, 60%).
* compound 2-15 synthesis
B-15-4 (11.41g, 16.9mmol), positive third borine (0.95g, 6.76mmol) is added to be dissolved in first in reaction vessel The mixed solvent of benzene, 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 is dried with MgSO4.Vacuum distillation uses silicagel column after removing solvent Son purification obtains compound 2-15 (9.82g, 91%).
[embodiment 2] compound 2-19 synthesis
2-19 (7.64g, 88%) is obtained according to 2-15 synthetic methods
[embodiment 3] compound 2-30 synthesis
2-30 (9.89g, 93%) is obtained according to 2-15 synthetic methods
[embodiment 4] compound 2-39 synthesis
Compound 2-39 intermediate is prepared to intermediate B -15-4 synthetic methods according to 2-15 intermediate B -15-1 B-39-4
* compound 2-39 synthesis
Add B-39-4 (10.39g, 16.9mmol), phenyl boric acid (2.24g, 18.4mmol), four triphenylphosphines in reaction vessel Palladium (0.7g, 1.08mmol), potassium carbonate (5.3g, 38.3mmol), toluene 60mL, ethanol 20mL and distilled water 20mL, at 120 DEG C Stir 3h.Distilled water stopping reaction being extracted with ethyl acetate after reaction terminates.Organic layer is dried with MgSO4.Vacuum distillation is gone Fall solvent and obtain compound 2-39 (7.05g, 68%) with silicon gel column purification later.
[embodiment 5] compound 2-48 synthesis
2-48 (6.64g, 62%) is obtained according to 2-39 synthetic methods
[embodiment 6] compound 2-60 synthesis
2-60 (8.03g, 67%) is obtained according to 2-39 synthetic methods
[embodiment 7] compound 3-15 synthesis
* intermediate C-15-1 synthesis
Synthetic method according to intermediate B -15-1 obtains C-15-1
* intermediate C-15-2 synthesis
HCl (35.0~37.0%, 20mL) is added in reactor and 1,4- dioxanes (120mL) are sufficiently mixed, and is reacted Add 2,7- dibromos acridine (15.16g, 45mmol) and paraformaldehyde (4.0g, 113mmol) return stirring 2h later in system.So Stirring at normal temperature 16h afterwards.Organic layer is separated with dichloromethane after being terminated with water reaction, is dried with MgSO4.Vacuum distillation is removed molten Agent, the organic layer isolated compound 2 of silica gel column chromatography, the bromo- 9-chloroacridines of 7- bis- (13.61g, 81%).
The bromo- 9-chloroacridines (6.76g, 18.2mmol) of 2,7- 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-15-2 (3.19g, 48%).
* intermediate C-15-3 synthesis
Add C-15-2 (6.13g, 16.9mmol), naphthalene boronic acids (2.93g, 17.01mmol), four triphenylphosphines in reaction vessel Palladium (0.7g, 1.08mmol), potassium carbonate (5.3g, 38.3mmol), toluene 60mL, ethanol 20mL and distilled water 20mL, 120 DEG C, Stir 3h.Distilled water stopping reaction being extracted with ethyl acetate after reaction terminates.Organic layer is dried with MgSO4.Vacuum distillation is gone Fall solvent and obtain compound C-15-3 (4.52g, 65%) with silicon gel column purification later.
* intermediate C-15-4 synthesis
Two (4- xenyls) amine (29.22g, 59.1mmol), C-15-3 are added under condition of nitrogen gas in reaction vessel The palladium (0.1g) of (24.05g, 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-15-4 (25.95g, 68%).
* chemical combination 3-15 synthesis
Under condition of nitrogen gas, 75mL dimethylformamides DMF, C-15-4 (16.89,27mmol), 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 3-15 (19.62g, 89%).
[embodiment 8] compound 3-89 synthesis
3-89 (20.43g, 85%) is obtained according to 3-15 synthetic methods
[embodiment 9] compound 3-96 synthesis
[embodiment 10] compound 4-3 synthesis
Synthetic method according to 3-15 synthesizes compound 4-3, and wherein D-3-3 is synthesized according to C-15-4 synthetic methods, remaining step It is rapid identical, finally give compound 4-3 (20.09g, 87%).
[embodiment 11] compound 4-6 synthesis
Synthetic method according to 2-39 obtains 4-6, wherein D-6-3, D-6-4 reference C-15-4 synthetic method, final to obtain To compound 4-6 (10.27g, 68%)
[embodiment 11] compound 4-32 synthesis
Synthetic method according to 4-6 obtains 4-32 (7.97g, 65%).
The FD-MS values for the acridine compounds that the embodiment of the present invention is prepared such as table 1 is represented.
The FD-MS values of [table 1] acridine compounds
Compound FD-MS
2-15 M/z=638.27 (C48H34N2)=638.81)
2-19 M/z=513.21 (C38H27NO=513.64)
2-30 M/z=629.22 (C46H31NS=629.82)
2-39 M/z=613.19 (C45H27NS=613.78)
2-48 M/z=633.25 (C49H31N=633.79)
2-60 M/z=709.28 (C55H35N=709.89)
3-15 M/z=816.33 (C60H40N4=817.01)
3-89 M/z=890.34 (C66H42N4=891.09)
3-96 M/z=979.37 (C72H45N5=980.19)
4-3 M/z=855.34 (C62H41N5=856.05)
4-6 M/z=893.38 (C67H47N3=894.13)
4-32 M/z=725.27 (C49H31N3S2=725.93)
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 electron transfer 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 of [table 2] luminescent device
From the above-mentioned result of table 2, it is seen that the luminous efficiency and life characteristic of acridine compounds of the invention have significantly Improve.
The organic luminescent device that the present invention is prepared using acridine compounds, can obtain the knot of luminous efficiency and life-span well Really, so the present invention has higher practicality in OLED industries.The organic luminescent device of the present invention show in flat panel, put down Planar luminous body, illumination face illuminating OLED illuminator, flexible illuminator, duplicator, printer, LCD backlight lamp or dosing machine class The field such as light source, display board, mark can widely use.

Claims (4)

1. a kind of acridine compounds, it is characterised in that the acridine compounds general molecular formula is：
[chemical formula 1]
Any one 2. acridine compounds according to claim 1, in following chemical formula [2~4].
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
Ar1~Ar4It is mutual the same or different substituted or unsubstituted hydrogen atom, substituted or unsubstituted C6~C60Aryl, Substituted or unsubstituted C5~C60Condensed ring radical or heterocyclic radical；Ar1 and Ar2 or Ar3 and Ar4 can be formed ring structure condensed ring radical and Heterocyclic radical；Ar5Selected from hydrogen atom, substituted or unsubstituted C1~C60Alkyl, substituted or unsubstituted C1~C60Alkoxy, substitution Or unsubstituted C1~C60Ether alkyl, substituted or unsubstituted C6~C60Aryl, substituted or unsubstituted C5~C60Condensed ring radical or Heterocyclic radical.
3. acridine compounds according to claim 1 or 2, it is characterised in that any one is changed in following chemical formula Compound：
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 claims 1 to 3 is any one Acridine compounds described in.
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