CN109134369A - A kind of Acridine derivatives and its organic luminescent device - Google Patents

A kind of Acridine derivatives and its organic luminescent device Download PDF

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CN109134369A
CN109134369A CN201811153931.XA CN201811153931A CN109134369A CN 109134369 A CN109134369 A CN 109134369A CN 201811153931 A CN201811153931 A CN 201811153931A CN 109134369 A CN109134369 A CN 109134369A
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韩春雪
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract

The present invention provides a kind of Acridine derivatives and its organic luminescent device, is related to organic optoelectronic materials technology.By in fluorenes alkene structure, connecting substituted or unsubstituted acridinyl group, there are a pair of of lone pair electrons on the nitrogen of No. 10 positions in acridine can freely match the present invention.Since it is with special rigid plane condensed cyclic structure, the movement of group entirety can be made relatively limited, effectively improve the glass transition temperature of derivative, be conducive to form a film.Such derivative preparation method is simple, raw material is easy to get, and is applied in OLED device as material of main part, can improve the luminous efficiency of device significantly, while the driving voltage of device can also be effectively reduced, be the OLED material of a kind of function admirable.

Description

A kind of Acridine derivatives and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical field more particularly to a kind of Acridine derivatives and its organic illuminator Part.
Background technique
The Tang etc. of Kodak Company in 1987 has invented sandwich type organic bilayer film luminescent device, this is breakthrough Progress allows it is seen that the great potential that OLED technology move towards functionization, moves towards commercial market, has started organic light-emitting diodes The research boom of pipe.Over 30 years, OLED technology achieves development with rapid changepl. never-ending changes and improvements, moves towards the industrialization life from laboratory research It produces.
Due to unique " sandwich " the type structure of Organic Light Emitting Diode (OLED) and its ultra-thin, light, high brightness, complete The excellent performances such as color transmitting, low driving voltage, response time be fast, it is fast-developing as potential in past twenties years Follow-on display and solid state illumination technology.Especially after the proposition of host-guest system concept, the efficiency of OLED has pole Big raising breaches the theoretical limitation of conventional fluorescent OLED internal quantum efficiency 25%.Currently, the development of OLED material has been arrived The stage of one comparative maturity, Materials Co., Ltd both domestic and external provide hundreds of innovative material and are provided with selecting.It is applied to The oled light sulfate ferroelectric functional material of OLED device can be divided into two major classes, i.e. charge injection transmission material and luminous material from purposes Material further can also inject charge into transmission material and be divided into electron injection transmission material and hole injection transmission material, can be with Luminescent material is divided into main body luminescent material and dopant material.Luminescent material needs to meet: (1) low concentration quenching phenomenon, suitably Emission wavelength, fluorescence quantum efficiency are as high as possible；(2) do not chemically reacted with electrode and carrier transmission material, heat, light, Chemical stability is good；(3) thickness control is between dozens to a few hundred nanometers, and film forming is good, and amorphous phase stability is good； (4) in molecule without or few faults of construction and have good processing performance；(5) excellent carrier transport ability；(6) HOMO and lumo energy differ less big with the work function of electrode material.Luminescent material generally comprises material of main part and object doping Material, wherein on the one hand the effect of material of main part is the transmission of equilbrium carrier, conducive to the compound of electrons and holes, on the other hand It is then the self-quenching for reducing excessive concentration.
All in all, the direction of the following OLED is to develop high efficiency, high brightness, the white light parts of low cost and full color to show Show device, but the technological industrialization process still faces many critical issues, how to design the better material of new performance and carry out It adjusts, is always those skilled in the art's urgent problem to be solved.
Summary of the invention
It is provided by the invention to organise the object of the present invention is to provide a kind of Acridine derivatives and its organic luminescent device Closing object has good electronic transmission performance, and thermal stability is good, and good film-forming property, synthetic method is simple to operation, uses the electronics There is the organic luminescent device of transmission material preparation good luminous efficiency and service life to show.
The present invention provides a kind of Acridine derivatives, and general formula of molecular structure is as shown in chemical formula I:
Wherein, Ar is selected from
Wherein, R be selected from substituted or unsubstituted C1~C8 alkyl, substituted or unsubstituted C6~C14 aryl, replace or not One of substituted C3~C13 heteroaryl；R5、R6、R7Independently selected from H, substituted or unsubstituted C1~C8 alkyl, replace Or one of unsubstituted C6~C14 aryl, substituted or unsubstituted C3~C13 heteroaryl；
R1、R2Independently selected from cyano, substituted or unsubstituted C1~C8 alkyl, substituted or unsubstituted C6~C14 virtue One of base, substituted or unsubstituted C3~C13 heteroaryl；
L is selected from singly-bound or following group:
Wherein, R3、R4Independently selected from H, substituted or unsubstituted C1~C8 alkyl, substituted or unsubstituted C6~C14 virtue One of base, substituted or unsubstituted C3~C13 heteroaryl.
Preferably, Ar is selected from one of following group:
Preferably, R1、R2In at least one be cyano；
L is selected from singly-bound or following group:
Wherein, R3、R4Independently selected from one in H, methyl, ethyl, isopropyl, tert-butyl, phenyl, xenyl, naphthalene Kind.
Preferably, R1For cyano, R2Selected from cyano or following group:
Preferably, R is selected from methyl, ethyl, propyl, butyl, isopropyl, isobutyl group, tert-butyl, substituted or unsubstituted benzene Base, terphenyl, naphthalene, acridinyl, phenanthryl, triphenylene, phenoxazine base, phenothiazinyl, phenoxazine thiophene base, two fluorenyl of spiral shell, 9, 9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, 9- phenyl carbazole base, pyrenyl, quinolyl, isoquinolyl, purine radicals, indyl, Ferrosin base, pyridyl group, pyrimidine radicals, pyrazinyl, pyridazinyl, triazine radical, thienyl, furyl, benzothienyl, benzofuran Base, dibenzothiophene, dibenzofuran group, benzo dibenzothiophene, benzo dibenzofuran group, benzo 9,9- dimethyl One of fluorenyl；
Wherein, substituent group is methyl, ethyl, isopropyl, tert-butyl, phenyl, any one or more in naphthalene.
Preferably, L is selected from singly-bound or following group:
Preferably, R5Selected from one of methyl, phenyl, xenyl, naphthalene；R6、R7Independently selected from H, methyl, ethyl, Propyl, butyl, isopropyl, isobutyl group, tert-butyl, substituted or unsubstituted phenyl, terphenyl, naphthalene, acridinyl, phenanthryl, Triphenylene, phenoxazine base, phenothiazinyl, phenoxazine thiophene base, two fluorenyl of spiral shell, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, 9- Phenyl carbazole base, pyrenyl, quinolyl, isoquinolyl, purine radicals, indyl, pyridyl group, pyrimidine radicals, triazine radical, thienyl, furan It mutters base, benzothienyl, benzofuranyl, dibenzothiophene, dibenzofuran group, benzo dibenzothiophene, benzo two One of benzofuranyl, benzo 9,9- dimethyl fluorenyl；
Wherein, substituent group is methyl, ethyl, isopropyl, tert-butyl, phenyl, any one or more in naphthalene.
Most preferably, any one of Acridine derivatives of the invention in chemical structure as follows:
The present invention also provides a kind of organic luminescent device, the organic luminescent device includes cathode, anode and is placed in institute State between two electrodes and except one or more organic matter layers, the organic matter layer contains any a word used for translation of the present invention Pyridine analog derivative.
Preferably, organic matter layer of the present invention includes material of main part, is contained in material of main part of the present invention any Kind Acridine derivatives.
Beneficial effects of the present invention:
The present invention provides a kind of Acridine derivatives and its organic luminescent device, and the present invention is by fluorenes alkene structure, even Connect substituted or unsubstituted acridinyl group.On the one hand, there are a pair of of lone pair electrons in acridine on the nitrogen of No. 10 positions can be free Matching.Acridine also all has ideal photo electric as a kind of common electron rich organic functional group, compounds mostly It can be with outstanding charge transport ability；And since it is with special rigid plane condensed cyclic structure, group entirety can be made It moves relatively limited, can effectively improve the glass transition temperature of derivative, be conducive to form a film.
Acridine derivatives preparation method of the present invention is simple, and raw material is easy to get, and can satisfy industrialization demand.
Acridine derivatives of the present invention are applied in organic luminescent device, can be used as material of main part, using this hair The organic luminescent device of the bright Acridine derivatives preparation has good luminous efficiency and reduces the driving voltage of device.
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 a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, art technology Personnel's every other embodiment obtained without making creative work, belongs to protection scope of the present invention.
Alkyl of the present invention refers to alkyl made of minusing a hydrogen atom in alkane molecule, can be straight chain alkane Base, branched alkyl, naphthenic base, example may include methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth Base, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Aryl of the present invention refers to remove a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule after, be left the total of univalent perssad Claiming, can be monocyclic aryl or fused ring aryl, example may include phenyl, xenyl, naphthalene, acridinyl, phenanthryl or pyrenyl etc., But not limited to this.
Heteroaryl of the present invention refers to the group that one or more aromatic core carbon in aryl are substituted by hetero atom General name, the hetero atom include but is not limited to oxygen, sulphur or nitrogen-atoms, and the heteroaryl can be bicyclic heteroaryl or condensed ring heteroaryl Base, example may include pyridyl group, pyrrole radicals, pyrimidine radicals, thienyl, furyl, indyl, quinolyl, isoquinolyl, benzo thiophene Pheno base, benzofuranyl, dibenzofuran group, dibenzothiophene, carbazyl etc., but not limited to this.
Substituted alkyl of the present invention, substituted aryl, substituted heteroaryl, the substituent group is independently selected from first Base, ethyl, isopropyl, tert-butyl, phenyl, xenyl, terphenyl, naphthalene, acridinyl, phenanthryl, benzo phenanthryl, base, pyrene Base, benzyl, fluorenyl, 9,9- dimethyl fluorenyl, hexichol amido, dimethylamino, carbazyl, 9- phenyl carbazole base, acridinyl, furan It mutters base, thienyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophene, deuterium base, phenothiazinyl, pheno Oxazines base, piperidyl, pyridyl group, pyrazinyl, pyridazinyl, quinazolyl, quinoxalinyl, indyl, triazine radical, pyrimidine radicals, three Methyl fluoride, cyano, halogen atom, nitro etc., but not limited to this.
The present invention provides a kind of Acridine derivatives, and general formula of molecular structure is as shown in chemical formula I:
Wherein, Ar is selected from
Wherein, R be selected from substituted or unsubstituted C1~C8 alkyl, substituted or unsubstituted C6~C14 aryl, replace or not One of substituted C3~C13 heteroaryl；R5、R6、R7Independently selected from H, substituted or unsubstituted C1~C8 alkyl, replace Or one of unsubstituted C6~C14 aryl, substituted or unsubstituted C3~C13 heteroaryl；
R1、R2Independently selected from cyano, substituted or unsubstituted C1~C8 alkyl, substituted or unsubstituted C6~C14 virtue One of base, substituted or unsubstituted C3~C13 heteroaryl；
L is selected from singly-bound or following group:
Wherein, R3、R4Independently selected from H, substituted or unsubstituted C1~C8 alkyl, substituted or unsubstituted C6~C14 virtue One of base, substituted or unsubstituted C3~C13 heteroaryl.
Preferably, Ar is selected from one of following group:
Preferably, R1、R2In at least one be cyano；
L is selected from singly-bound or following group:
Wherein, R3、R4Independently selected from one in H, methyl, ethyl, isopropyl, tert-butyl, phenyl, xenyl, naphthalene Kind.
Preferably, R1For cyano, R2Selected from cyano or following group:
Preferably, R is selected from methyl, ethyl, propyl, butyl, isopropyl, isobutyl group, tert-butyl, substituted or unsubstituted benzene Base, terphenyl, naphthalene, acridinyl, phenanthryl, triphenylene, phenoxazine base, phenothiazinyl, phenoxazine thiophene base, two fluorenyl of spiral shell, 9, 9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, 9- phenyl carbazole base, pyrenyl, quinolyl, isoquinolyl, purine radicals, indyl, Ferrosin base, pyridyl group, pyrimidine radicals, pyrazinyl, pyridazinyl, triazine radical, thienyl, furyl, benzothienyl, benzofuran Base, dibenzothiophene, dibenzofuran group, benzo dibenzothiophene, benzo dibenzofuran group, benzo 9,9- dimethyl One of fluorenyl；
Wherein, substituent group is methyl, ethyl, isopropyl, tert-butyl, phenyl, any one or more in naphthalene.
Preferably, L is selected from singly-bound or following group:
Preferably, R5Selected from one of methyl, phenyl, xenyl, naphthalene；R6、R7Independently selected from H, methyl, ethyl, Propyl, butyl, isopropyl, isobutyl group, tert-butyl, substituted or unsubstituted phenyl, terphenyl, naphthalene, acridinyl, phenanthryl, Triphenylene, phenoxazine base, phenothiazinyl, phenoxazine thiophene base, two fluorenyl of spiral shell, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, 9- Phenyl carbazole base, pyrenyl, quinolyl, isoquinolyl, purine radicals, indyl, pyridyl group, pyrimidine radicals, triazine radical, thienyl, furan It mutters base, benzothienyl, benzofuranyl, dibenzothiophene, dibenzofuran group, benzo dibenzothiophene, benzo two One of benzofuranyl, benzo 9,9- dimethyl fluorenyl；
Wherein, substituent group is methyl, ethyl, isopropyl, tert-butyl, phenyl, any one or more in naphthalene.
Most preferably, any one of Acridine derivatives of the invention in chemical structure as follows:
Acridine derivatives of the present invention are obtained by following synthetic route:
Wherein, Ar is selected from
Wherein, R be selected from substituted or unsubstituted C1~C8 alkyl, substituted or unsubstituted C6~C14 aryl, replace or not One of substituted C3~C13 heteroaryl；R5、R6Independently selected from H, substituted or unsubstituted C1~C8 alkyl, replace or not One of substituted C6~C14 aryl, substituted or unsubstituted C3~C13 heteroaryl；
R1、R2Independently selected from cyano, substituted or unsubstituted C1~C8 alkyl, substituted or unsubstituted C6~C14 virtue One of base, substituted or unsubstituted C3~C13 heteroaryl；
L is selected from singly-bound or following group:
Wherein, R3、R4Independently selected from H, substituted or unsubstituted C1~C8 alkyl, substituted or unsubstituted C6~C14 virtue One of base, substituted or unsubstituted C3~C13 heteroaryl.
The present invention is not particularly limited the source of raw material employed in this above-mentioned all kinds of reaction, can be used commercially available Products material is spread out using the acridine that preparation method well-known to those skilled in the art obtains chemical formula I of the present invention Biology.
The present invention limitation not special to above-mentioned reaction be using popular response well-known to those skilled in the art Can, the preparation method is simple, easily operated.
The present invention also provides a kind of organic luminescent device, the organic luminescent device includes cathode, anode and is placed in institute State between two electrodes and except one or more organic matter layers, the organic matter layer contains acridine of the present invention and spreads out Biology.The organic matter layer of organic luminescent device of the invention can have single layer structure, or with two layers or more of multilayer knot Structure.Wherein organic matter layer may include hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electronics Transport layer, electron injecting layer, coating or any one layer being placed in the buffer layer between anode and hole injection layer or Any multilayer.Wherein luminescent layer of the present invention can be light emitting host doping and shine and can be also possible to single object in the form of Matter is as luminescent layer.
Preferably, the organic matter layer includes material of main part, contains any acridine of the present invention in material of main part Analog derivative.
Preferably, anode of the present invention commonly uses transparent indium tin oxide (indium tin oxide, ITO) glass.
Preferably, hole injection layer of the present invention is selected from 2-TNATA, HAT-CN, TDATA, MTDATA, DNTPD etc., The single structure that can be single substance composition can also be the single layer structure or multilayered structure of different material formation.
Preferably, hole transmission layer of the present invention is selected from NPB, TPD, CBP, spiro-TAD etc..
Preferably, electronic barrier layer of the present invention can be selected from α-NPD, TDATA, TPD, TAPC, Spiro-TAD etc..
Preferably, luminescent layer material of main part of the present invention be selected from ADN, CPB, mCP, TCTA, α-ADN, 4P-NPB, TCP, TCTA etc. can be the single layer structure of single substance composition, can also be the single layer structure or multilayer of different material formation Structure.
Preferably, green light emitting layer object of the present invention is selected from Ir (ppy)3、Ir(ppy)2(acac)、DMQA、DBQA、 TMDBQA etc..
Preferably, red light luminescent layer object of the present invention is selected from Ir (piq)3、Ir(piq)2(acac)、DCJTB、DCJT、 DCM, DCM2 etc..
Preferably, hole blocking layer of the present invention is selected from BCP, TPBi, Alq3, Liq, BAlq and TAZ etc..
Preferably, electron transfer layer of the present invention is selected from BCP, TPBi, Alq3, Liq, BAlq and TAZ etc..
Preferably, electron injecting layer of the present invention can be selected from LiF.
Preferably, cathode of the present invention is mostly frequently with the metal of low work function (Mg, Al, Ga, Ag, Mg-Ag alloy etc.).
Its structure of Acridine derivatives and its organic luminescent device of the present invention is preferred are as follows: substrate/anode/hole note Enter layer/hole transmission layer/luminescent layer/electron transfer layer/electron injecting layer/cathode.However, the structure of organic luminescent device is unlimited In this.Acridine derivatives and its organic luminescent device of the present invention can according to the characteristic of device parameter requirements and material into Row selection and combination, can also add or omit part organic layer.
Acridine derivatives of the present invention are used as material of main part, preferably to manufacture the organic of construction same as below Luminescent device:
ITO/2-TNATA (50nm)/NPB (30nm)/Acridine derivatives of the present invention: Ir (ppy)3(30nm)/ TPBi(30nm)/LiF(0.5nm)/Al(200nm)。
ITO/2-TNATA (50nm)/NPB (30nm)/Acridine derivatives of the present invention: Ir (piq)2(acac) (30nm)/TPBi(30nm)/LiF(0.5nm)/Al(200nm)。
The preparation of organic matter layer can be vacuum vapour deposition, spin-coating method, vapor deposition, knife coating, laser thermal transfer, EFI Rubbing method, slit coating method, any one in dipping formula rubbing method, preferably use the side of vacuum evaporation in the present invention Method.
Organic luminescent device of the present invention can be widely applied to Display panel, lighting source, flexibility OLED, Electronic Paper, The fields such as Organophotoreceptor or Organic Thin Film Transistors, direction board, signal lamp.
The synthesis of [embodiment 1] compound 1
Step1: compound b (3.42g, 13.20mmol) is dissolved completely in 50ml N, N- in 250ml round-bottomed flask In dimethylformamide, acquired solution is then stirred at normal temperature.Into the reaction solution add malononitrile (1.05g, 15.84mmol), then acquired solution is stirred at normal temperature 1 hour.After reaction terminates, water is added thereto, and is filtered logical It crosses and acquired solution is stirred into 10 minutes sediments generated.Gained residue is diluted with ethyl acetate, is removed through anhydrous magnesium sulfate Then moisture, filtration residue are concentrated under reduced pressure.The solution silica gel column chromatography (Hex:EA=3:1) of concentration is purified to make Standby compound c (2.10g, 52%).
Step2: being added compound a (16.46g, 50mmol) in reactor, compound c (15.36g, 50mmol), and four or three Phenylphosphine palladium (1.15g, 1mmol) and sodium carbonate (41.4g, 300mmol), by weighed reactant be dissolved in toluene (1L)/ In EtOH (200mL)/distilled water (200mL) solvent, 90 DEG C are heated 2 hours.The reaction mixture is cooled to room temperature, first is used Benzene is diluted and is filtered via diatomite.The filtrate water is diluted, and is extracted with toluene, and merges organic phase, by its It is evaporated under vacuum.The residue is filtered via silica gel, and is recrystallized.Obtaining compound 1, (17.40g, yield are 68%).
Mass spectrum m/z:511.21 (calculated value: 511.20).Theoretical elemental content (%) C37H25N3: C, 86.86；H, 4.93； N, 8.21 actual measurement constituent content (%): C, 86.86；H, 4.92；N, 8.22.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 2] compound 3
Step1: intermediate g (11.82g, 41mmol), compound 3-e (10.54g, 41.5mmol), cuprous iodide are weighed (3.9g, 20.5mmol), ethylenediamine (1.4mL, 20.5mmol) and cesium carbonate (40g, 123mmol), and be added by said sequence To in toluene (250mL), return stirring.It vacuum distillation, methylene chloride and hexane is extracted with ethyl acetate crosses pillar and obtain chemical combination Object 3-a (14.10g, 83%).
Step2: compound 3-a (15.58g, 37.6mmol) is dissolved in tetrahydrofuran (140mL), under the conditions of -78 DEG C After hexane solvent and 2.5M n-BuLi (18mL, 45.1mmol) is added dropwise, stir 1 hour.Trimethylborate is slowly added dropwise again After (13mL, 56.4mmol), 2h is stirred.2M hydrochloric acid is added dropwise again to neutralize, extract product with ethyl acetate and water.Use methylene chloride Compound 3-A (9.55g, 67%) is recrystallized to give with hexane.
Step3: compound b (3.42g, 13.20mmol) is dissolved completely in 50ml N, N- in 250ml round-bottomed flask In dimethylformamide, acquired solution is then stirred at normal temperature.Into the reaction solution add malononitrile (1.05g, 15.84mmol), then acquired solution is stirred at normal temperature 1 hour.After reaction terminates, water is added thereto, and is filtered logical It crosses and acquired solution is stirred into 10 minutes sediments generated.Gained residue is diluted with ethyl acetate, is removed through anhydrous magnesium sulfate Then moisture, filtration residue are concentrated under reduced pressure.The solution silica gel column chromatography (Hex:EA=3:1) of concentration is purified to make Standby compound c (2.10g, 52%).
Step4: being added compound 3-A (18.96g, 50mmol) in reactor, compound c (15.30g, 50mmol), and four Triphenylphosphine palladium (1.15g, 1mmol) and sodium carbonate (41.4g, 300mmol), by weighed reactant be dissolved in toluene (1L)/ In EtOH (200mL)/distilled water (200mL) solvent, 90 DEG C are heated 2 hours.The reaction mixture is cooled to room temperature, first is used Benzene is diluted and is filtered via diatomite.The filtrate water is diluted, and is extracted with toluene, and merges organic phase, by its It is evaporated under vacuum.The residue is filtered via silica gel, and is recrystallized.Obtaining compound 3, (18.25g, yield are 65%).
Mass spectrum m/z:561.23 (calculated value: 561.22).Theoretical elemental content (%) C41H27N3: C, 87.67；H, 4.85； N, 7.48 actual measurement constituent content (%): C, 87.68；H, 4.85；N, 7.47.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 3] compound 4
The compound 3-e in 2 compound 3 of embodiment is changed into equimolar compound 4-e, according to 2 compound 3 of embodiment Synthetic method obtain compound 4 (19.27g, 63%).
Mass spectrum m/z:611.27 (calculated value: 611.24).Theoretical elemental content (%) C45H29N3: C, 88.35；H, 4.78； N, 6.87 actual measurement constituent content (%): C, 88.35；H, 4.79；N, 6.86.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 4] compound 16
The compound 3-e in 2 compound 3 of embodiment is changed into equimolar compound 16-e, according to 2 compound of embodiment 3 synthetic method obtains compound 16 (18.05g, 60%).
Mass spectrum m/z:601.24 (calculated value: 601.22).Theoretical elemental content (%) C43H27N3O:C, 85.83；H, 4.52； N, 6.98；O, 2.66 actual measurement constituent content (%): C, 85.84；H, 4.52；N, 6.98；O, 2.65.The above results confirmation is produced Object is target product.
The synthesis of [embodiment 5] compound 22
The compound 3-e in 2 compound 3 of embodiment is changed into equimolar compound 22-e, according to 2 compound of embodiment 2 synthetic method obtains compound 22 (15.63g, 61%).
Mass spectrum m/z:512.17 (calculated value: 512.20).Theoretical elemental content (%) C36H24N4.:C, 84.35；H, 4.72； N, 10.93 actual measurement constituent content (%): C, 84.36；H, 4.71；N, 10.93.The above results confirm to obtain product as target production Product.
The synthesis of [embodiment 6] compound 27
The compound 3-e in 2 compound 3 of embodiment is changed into equimolar compound 27-e, according to 2 compound of embodiment 2 synthetic method obtains compound 27 (16.88g, 60%).
Mass spectrum m/z:563.23 (calculated value: 563.22).Theoretical elemental content (%) C40H26N4: C, 85.38；H, 4.66； N, 9.96 actual measurement constituent content (%): C, 85.39；H, 4.66；N, 9.95.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 7] compound 48
Step1: being added compound a (16.46g, 50mmol) in reactor, compound f (17.95g, 50mmol), and four or three Phenylphosphine palladium (1.15g, 1mmol) and sodium carbonate (41.4g, 300mmol), by weighed reactant be dissolved in toluene (1L)/ In EtOH (200mL)/distilled water (200mL) solvent, 90 DEG C are heated 2 hours.The reaction mixture is cooled to room temperature, first is used Benzene is diluted and is filtered via diatomite.The filtrate water is diluted, and is extracted with toluene, and merges organic phase, by its It is evaporated under vacuum.The residue is filtered via silica gel, and is recrystallized.Obtain compound 48-A (17.56g, yield For 68%).
Other synthesis steps obtain compound 48 (19.58g, 59%) according to the synthetic method of compound 1.
Mass spectrum m/z:663.29 (calculated value: 663.27).Theoretical elemental content (%) C49H33N3: C, 88.66；H, 5.01； N, 6.33 actual measurement constituent content (%): C, 88.67；H, 5.01；N, 6.32.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 8] compound 54
In 250ml round-bottomed flask by compound b (2.50g, 8.92mmol), compound p (2.22g, 10.70mmol) and Sodium ethoxide (1.82g, 26.76mmol) is dissolved completely in 30ml ethyl alcohol, is then heated and is stirred acquired solution.React end Afterwards, the residue that obtains and being concentrated under reduced pressure products therefrom is diluted with tetrahydrofuran, and with water and salt water washing.It collects Organic solvent layer removes moisture through anhydrous magnesium sulfate, then filtration residue is concentrated under reduced pressure.The solution silica gel of concentration Column chromatography (Hex:EA=1:1) is purified with prepare compound t (2.40g, 60%).
Compound a (16.46g, 50mmol) is added in reactor, compound t (22.41g, 50mmol), four triphenylphosphines Weighed reactant is dissolved in toluene (1L)/EtOH by palladium (1.15g, 1mmol) and sodium carbonate (41.4g, 300mmol) In the solvent of (200mL)/distilled water (200mL), 90 DEG C are heated 2 hours.The reaction mixture is cooled to room temperature, it is dilute with toluene It releases and is filtered via diatomite.The filtrate water is diluted, and is extracted with toluene, and merges organic phase, by it in vacuum Under be evaporated.The residue is filtered via silica gel, and is recrystallized, compound 54 (20.56g, 63%) is obtained.
Mass spectrum m/z:652.20 (calculated value: 652.19).Theoretical elemental content (%) C42H25F5N2: C, 77.29；H, 3.86；F, 14.55；N, 4.29 actual measurement constituent content (%): C, 77.28；H, 3.85；F, 14.55；N, 4.29.The above results card The real product that obtains is target product.
The synthesis of [embodiment 9] compound 55
The compound p in 8 compound 54 of embodiment is changed into equimolar compound k, according to the synthesis side of compound 54 Method obtains compound 55 (21.11g, 64%).
Mass spectrum m/z:545.14 (calculated value: 545.12).Theoretical elemental content (%) C43H25F4N3: C, 78.29；H, 3.82；F, 11.52；N, 6.37 actual measurement constituent content (%): C, 78.28；H, 3.82；F, 11.52；N, 6.38.The above results card The real product that obtains is target product.
The synthesis of [embodiment 10] compound 60
The compound p in 8 compound 54 of embodiment is changed into equimolar compound m, according to the synthesis side of compound 54 Method obtains compound 60 (18.56g, 62%).
Mass spectrum m/z:598.23 (calculated value: 598.22).Theoretical elemental content (%) C42H28F2N2: C, 84.26；H, 4.71；F, 6.35；N, 4.68 actual measurement constituent content (%): C, 84.27；H, 4.71；F, 6.35；N, 4.67.The above results confirm Acquisition product is target product.
The synthesis of [embodiment 11] compound 62
The compound p in 8 compound 54 of embodiment is changed into equimolar compound n, according to the synthesis side of compound 54 Method obtains compound 62 (20.35g, 66%).
Mass spectrum m/z:616.23 (calculated value: 616.21).Theoretical elemental content (%) C42H27F3N2: C, 81.80；H, 4.41；F, 9.24；N, 4.54 actual measurement constituent content (%): C, 81.80；H, 4.42；F, 9.24；N, 4.53.The above results confirm Acquisition product is target product.
The synthesis of [embodiment 12] compound 64
The compound p in 8 compound 54 of embodiment is changed into equimolar compound q, according to the synthesis side of compound 54 Method obtains compound 64 (18.28g, 63%).
Mass spectrum m/z:580.24 (calculated value: 580.23).Theoretical elemental content (%) C42H29FN2: C, 86.87；H, 5.03； F, 3.27；N, 4.82 actual measurement constituent content (%): C, 86.88；H, 5.03；F, 3.27；N, 4.81.The above results confirmation is produced Object is target product.
The synthesis of [embodiment 13] compound 73
The compound f in 7 compound 48 of embodiment is changed into equimolar compound j, according to the synthesis side of compound 48 Method obtains compound 73 (19.39g, 66%).
Mass spectrum m/z:587.25 (calculated value: 587.24).Theoretical elemental content (%) C43H29N3: C, 87.88；H, 4.97； N, 7.15 actual measurement constituent content (%): C, 87.88；H, 4.98；N, 7.14；N, 2.95.The above results confirm that obtaining product is mesh Mark product.
The synthesis of [embodiment 14] compound 133
The compound a in 1 compound 1 of embodiment is changed into equimolar compound s, according to the synthetic method of compound 1 Obtain compound 133 (17.04g, 58%).
Mass spectrum m/z:587.25 (calculated value: 587.24).Theoretical elemental content (%) C43H29N3: C, 87.88；H, 4.97； N, 7.15 actual measurement constituent content (%): C, 87.88；H, 4.96；N, 7.14.The above results confirm that obtaining product is target product.
[comparative example 1] device prepares embodiment:
Ito glass substrate is placed in distilled water and is cleaned 2 times, it is ultrasonic washing 15 minutes, 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 2-TNATA/50nm is successively deposited on the ito transparent electrode having had been prepared for, vapor deposition hole passes Defeated layer NPB/30nm, vapor deposition main body CBP: doping Ir (piq)2(acac) 5% mixing/30nm, then vapor deposition electron transfer layer TPBi/30nm, cathode LiF/0.5nm, Al/200nm.
[Application Example 1-6]
CBP in comparative example 1 is changed into the shown compound 16,22,27,54,55,62 in embodiment 1-14.
Table 1 is the compound of preparation of the embodiment of the present invention and the characteristics of luminescence test for comparing luminescent device prepared by substance As a result.
The characteristics of luminescence of [table 1] luminescent device is tested
[comparative example 2] device prepares embodiment:
Ito glass substrate is placed in distilled water and is cleaned 2 times, it is ultrasonic washing 15 minutes, 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 2-TNATA/50nm is successively deposited on the ito transparent electrode having had been prepared for, vapor deposition hole passes Defeated layer NPB/30nm, vapor deposition main body CBP: doping Ir (ppy)35% mixing/30nm, then vapor deposition electron transfer layer TPBi/ 30nm, cathode LiF/0.5nm, Al/200nm.
[Application Example 7-14]
CBP in comparative example 2 is changed into shown compound 1 in embodiment 1-14,3,4,48,60,64,73, 133。
Table 2 is the compound of preparation of the embodiment of the present invention and the characteristics of luminescence test for comparing luminescent device prepared by substance As a result.
The characteristics of luminescence of [table 2] luminescent device is tested
The above result shows that Acridine derivatives of the invention are applied in organic luminescent device, especially as main body Material shows the low advantage of high-luminous-efficiency, driving voltage, is luminous organic material of good performance.
It should be pointed out that the present invention is particularly described with individual embodiments, but before not departing from the principle of the invention It puts, 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 scope.

Claims (10)

1. a kind of Acridine derivatives, which is characterized in that general formula of molecular structure is as shown in chemical formula I:
Wherein, Ar is selected from
Wherein, R is selected from substituted or unsubstituted C1~C8 alkyl, substituted or unsubstituted C6~C14 aryl, substituted or unsubstituted One of C3~C13 heteroaryl；R5、R6、R7Independently selected from H, substituted or unsubstituted C1~C8 alkyl, replace or not One of substituted C6~C14 aryl, substituted or unsubstituted C3~C13 heteroaryl；
R1、R2Independently selected from cyano, substituted or unsubstituted C1~C8 alkyl, substituted or unsubstituted C6~C14 aryl, take One of generation or unsubstituted C3~C13 heteroaryl；
L is selected from singly-bound or following group:
Wherein, R3、R4Independently selected from H, substituted or unsubstituted C1~C8 alkyl, substituted or unsubstituted C6~C14 aryl, One of substituted or unsubstituted C3~C13 heteroaryl.
2. a kind of Acridine derivatives according to claim 1, which is characterized in that Ar is selected from one of following group:
3. a kind of Acridine derivatives according to claim 1, which is characterized in that R1、R2In at least one be cyano；
L is selected from singly-bound or following group:
Wherein, R3、R4Independently selected from one of H, methyl, ethyl, isopropyl, tert-butyl, phenyl, xenyl, naphthalene.
4. a kind of Acridine derivatives according to claim 1, which is characterized in that R1For cyano, R2Selected from cyano or as follows Group:
5. a kind of Acridine derivatives according to claim 1, which is characterized in that R is selected from methyl, ethyl, propyl, fourth Base, isopropyl, isobutyl group, tert-butyl, substituted or unsubstituted phenyl, terphenyl, naphthalene, acridinyl, phenanthryl, triphenylene Base, phenoxazine base, phenothiazinyl, phenoxazine thiophene base, two fluorenyl of spiral shell, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, 9- phenyl click Oxazolyl, pyrenyl, quinolyl, isoquinolyl, purine radicals, indyl, ferrosin base, pyridyl group, pyrimidine radicals, pyrazinyl, pyridazinyl, Triazine radical, thienyl, furyl, benzothienyl, benzofuranyl, dibenzothiophene, dibenzofuran group, benzo hexichol One of bithiophene base, benzo dibenzofuran group, benzo 9,9- dimethyl fluorenyl；
Wherein, substituent group is methyl, ethyl, isopropyl, tert-butyl, phenyl, any one or more in naphthalene.
6. a kind of Acridine derivatives according to claim 1, which is characterized in that L is selected from singly-bound or following group:
7. a kind of Acridine derivatives according to claim 1, which is characterized in that R5Selected from methyl, phenyl, xenyl, naphthalene One of base；R6、R7Independently selected from H, methyl, ethyl, propyl, butyl, isopropyl, isobutyl group, tert-butyl, substitution or not Substituted phenyl, terphenyl, naphthalene, acridinyl, phenanthryl, triphenylene, phenoxazine base, phenothiazinyl, phenoxazine thiophene base, spiral shell two Fluorenyl, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, 9- phenyl carbazole base, pyrenyl, quinolyl, isoquinolyl, purine radicals, Indyl, pyridyl group, pyrimidine radicals, triazine radical, thienyl, furyl, benzothienyl, benzofuranyl, dibenzothiophene, One of dibenzofuran group, benzo dibenzothiophene, benzo dibenzofuran group, benzo 9,9- dimethyl fluorenyl；Its In, substituent group is methyl, ethyl, isopropyl, tert-butyl, phenyl, any one or more in naphthalene.
8. a kind of Acridine derivatives according to claim 1, which is characterized in that in chemical structure as follows Any one:
9. a kind of organic luminescent device, which is characterized in that the organic luminescent device include cathode, anode and be placed in it is described two electricity Between pole and except one or more organic matter layers, the organic matter layer contains a word used for translation according to any one of claims 1 to 8 Pyridine analog derivative.
10. a kind of organic luminescent device according to claim 9, which is characterized in that the organic matter layer includes main body Material contains Acridine derivatives according to any one of claims 1 to 8 in material of main part.
CN201811153931.XA 2018-09-30 2018-09-30 A kind of Acridine derivatives and its organic luminescent device Withdrawn CN109134369A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109134348A (en) * 2018-09-30 2019-01-04 长春海谱润斯科技有限公司 A kind of carbazole compound and its organic luminescent device
CN109293610A (en) * 2018-10-31 2019-02-01 长春海谱润斯科技有限公司 A kind of dibenzofuran derivative and its organic electroluminescence device
CN112094638A (en) * 2019-06-18 2020-12-18 上海和辉光电有限公司 Organic light-emitting material and OLED device

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109134348A (en) * 2018-09-30 2019-01-04 长春海谱润斯科技有限公司 A kind of carbazole compound and its organic luminescent device
CN109293610A (en) * 2018-10-31 2019-02-01 长春海谱润斯科技有限公司 A kind of dibenzofuran derivative and its organic electroluminescence device
CN109293610B (en) * 2018-10-31 2021-09-07 长春海谱润斯科技股份有限公司 Dibenzofurane derivative and organic electroluminescent device thereof
CN112094638A (en) * 2019-06-18 2020-12-18 上海和辉光电有限公司 Organic light-emitting material and OLED device

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Application publication date: 20190104