CN108218787A - A kind of pyrene compound and its organic luminescent device - Google Patents

A kind of pyrene compound and its organic luminescent device Download PDF

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CN108218787A
CN108218787A CN201810297270.1A CN201810297270A CN108218787A CN 108218787 A CN108218787 A CN 108218787A CN 201810297270 A CN201810297270 A CN 201810297270A CN 108218787 A CN108218787 A CN 108218787A
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unsubstituted
substituted
pyrene
alkyl
compound
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刘喜庆
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The invention discloses a kind of pyrene compound and its organic luminescent devices, are related to organic optoelectronic materials technology.On the one hand, pyrene ring structure shows the blue light performance haveing excellent performance because of its higher triplet and wider energy gap；On the other hand, by connecting benzimidazole, naphtho- imidazoles, phenanthro- imidazoles or pyridine imidazole group in molecule, the electron transport ability of structure is increased, by connecting tertiary aromatic amine structure, the cavity transmission ability of structure is enhanced, the combination of the two causes carrier transport to balance.It is applied to organic luminescent device, is used especially as the blue dopant material in luminescent layer, device shows the advantages of driving voltage is low, luminous efficiency is high, better than existing common OLED device.The good application effect shown in OLED luminescent devices, this point show it with good industrialization prospect.

Description

A kind of pyrene compound and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical field more particularly to a kind of pyrene compounds and its organic illuminator Part.
Background technology
Organic electroluminescent LED (Organic Light Emitting Diode, OLED) is to utilize electrons and holes The recombination luminescence in organic film and the luminescent device prepared, have the following advantages：(1) from main light emission, backlight is not needed to； (2) brightness is high, there is high contrast, pure in colour, the problem of almost without visible angle；(3) it is ultra-thin, by very thin organic Material coating and basis material are formed, small to be suitable for portable product；(4) power consumption is very small, environmental protection and energy saving；(5) it rings It answers speed fast, is the one thousandth of LCD；(6) use temperature range is wide, remains to normally show at -40 DEG C.
General organic luminescent device (OLED) is the organic matter layer structure by being inserted between cathode, anode and cathode and anode Into, the composition of device is transparent ITO anode, hole injection layer (TIL), hole transmission layer (HTL), luminescent layer (EL), hole The formation such as barrier layer (HBL), electron transfer layer (ETL), electron injecting layer (EIL), LiAl, cathode.
Luminescent material is the core of OLED technology, and the blue material as one of three primary colours is particularly critical, this is because not Only material can obtain blue-light device as luminescent layer in itself, can also adulterate thereto other luminescent colors material obtain it is white Light luminescent device.Up to the present, blue light material develop for green light and red light material more slowly, this mainly due to Blue light organic semiconducting materials forbidden band is wider, and electron energy level and device electronic level-density parameter are poor, affect carrier It is efficiently injected into so that such material is difficult the problems such as taking into account efficiency, stability and excitation purity.Therefore, develop function admirable Blue light material, it is particularly significant for the development of organic electroluminescence device.
In recent years, how construction unit of the pyrene as a kind of novel blue light material causes the extensive concern of researcher The luminescent material for designing the better pyrene class formation of new performance is adjusted, and being always that those skilled in the art are urgently to be resolved hurrily asks Topic.
Invention content
The object of the present invention is to provide a kind of pyrene compound and its organic luminescent devices.Pyrene class chemical combination provided by the invention Object thermal stability is high, glass transition temperature is high, by the compound for manufactured organic luminescent device in luminescent layer, shows The advantages of driving voltage is low, luminous efficiency is high is the luminous organic material of function admirable.
The present invention provides a kind of pyrene compounds, and general formula of molecular structure is as shown in I：
Wherein, Ar1、Ar2Independently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30 Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind or the two be interconnected cyclization；R is selected from substitution or not Substituted C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C50Heteroaryl in One kind；CY is substituted or unsubstituted C6~C30Aryl.
Preferably, a kind of pyrene compound, general formula of molecular structure such as II or III：
Wherein, Ar1、Ar2Independently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30 Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind or the two be interconnected cyclization；R is selected from substitution or not Substituted C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl in one kind；CY is selected from phenyl, naphthalene, anthryl, phenanthrene Base or pyrenyl.
Preferably, a kind of pyrene compound, general formula of molecular structure such as IV or V：
Wherein, Ra~RdIndependently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30's Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind；R is selected from substituted or unsubstituted C1~C10Alkyl, take Generation or unsubstituted C6~C30Aryl in one kind；CY is selected from phenyl, naphthalene, anthryl, phenanthryl or pyrenyl.
Preferably, the CY is selected from naphthalene, anthryl, phenanthryl or pyrenyl.
Preferably, the Ar1、Ar2Independently selected from one kind in lower structure：
Wherein, R1~R7Independently selected from hydrogen, substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C1~ C10Alkoxy, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind；More Preferably, R1~R7Independently selected from hydrogen, methyl, methoxyl group, ethyl, isopropyl, tertiary butyl, cyclohexyl, phenyl, naphthalene, phenanthrene Base, anthryl, pyrenyl, base, indenyl, triphenylene, furyl, thienyl, pyrrole radicals, dibenzofurans, dibenzothiophenes, click Oxazolyl, fluorenyl, two fluorenyl of spiral shell, acridinyl, phenothiazinyl, phenoxazine groups or indyl；R8~R11Independently selected from substitution or not Substituted C1~C10Alkyl, substituted or unsubstituted C1~C10Alkoxy, substituted or unsubstituted C6~C30Aryl in One kind；It is furthermore preferred that R8~R11Independently selected from methyl, methoxyl group, ethyl, isopropyl, tertiary butyl, cyclohexyl, phenyl or Naphthalene；A is selected from 0~3 integer.
Further preferably, any one of a kind of pyrene compound in chemical constitution as follows：
The present invention also provides a kind of organic luminescent devices, including first electrode, second electrode and are placed in two electrode Between one or more organic compound layers, the organic compound layer contains a kind of pyrene class chemical combination of any one of them Object.
Preferably, organic compound layer includes luminescent layer, contains a kind of pyrene compound of any one of them in luminescent layer.
Beneficial effects of the present invention：
The present invention provides a kind of pyrene compounds, on the one hand, pyrene ring structure is because of its higher triplet and wider Energy gap, show the blue light performance haveing excellent performance；On the other hand, by connecting benzimidazole, naphtho- imidazoles, phenanthro- in molecule Imidazoles or pyridine imidazole group increase the electron transport ability of structure, by connecting tertiary aromatic amine structure, enhance the sky of structure Cave transmittability, the combination of the two cause carrier transport to balance.It is applied to organic luminescent device, especially as luminous Blue dopant material in layer uses, and device shows the advantages of driving voltage is low, luminous efficiency is high, better than existing common OLED Device.The good application effect shown in OLED luminescent devices, this point show it with good industrialization prospect.
Specific embodiment：
It is clearly and completely described below in conjunction with the technical solution of the embodiment of the present invention, it is clear that described implementation Example is only part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, art technology Personnel's all other embodiments obtained without making creative work, belong to protection scope of the present invention.
Alkyl of the present invention refers to minus the alkyl that a hydrogen atom forms in alkane molecule, can be straight chain alkane Base, branched alkyl, cycloalkyl, 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 after removing a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule, is left the total of univalent perssad Claiming, can be monocyclic aryl or fused ring aryl, example may include phenyl, xenyl, naphthalene, anthryl, phenanthryl or pyrenyl etc., but It is without being limited thereto.
Heteroaryl of the present invention refers to the group that one or more of aryl aromatic core carbon is substituted by hetero atom General name, the hetero atom include but 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, pyridyl group, thienyl, furyl, indyl, quinolyl, isoquinolyl, benzo thiophene Fen base, benzofuranyl, dibenzofuran group, dibenzothiophene, carbazyl etc., but not limited to this.
The present invention provides a kind of pyrene compounds, and general formula of molecular structure is as shown in I：
Wherein, Ar1、Ar2Independently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30 Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind or the two be interconnected cyclization；R is selected from substitution or not Substituted C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C50Heteroaryl in One kind；CY is substituted or unsubstituted C6~C30Aryl.
According to the present invention, the substituted alkyl, the aryl replaced, the heterocycle replaced, the choosing of the substituent group independence From methyl, ethyl, isopropyl, tertiary butyl, phenyl, naphthalene, anthryl, phenanthryl, benzo phenanthryl, base, pyrenyl, benzyl, methoxy Base, methyl mercapto, phenoxy group, thiophenyl, fluorenyl, 9,9- dimethyl fluorenyl, hexichol amido, dimethylamino, carbazyl, 9- phenyl clicks Oxazolyl, furyl, thienyl, cyano, fluorine-based, deuterium base, triphenyl silicon substrate, trimethyl silicon substrate, phenothiazinyl, phenoxazine group, a word used for translation Piperidinyl, piperidyl, pyridyl group, pyrimidine radicals, xenyl, terphenyl, nitro etc., but not limited to this.
Preferably, a kind of pyrene compound, general formula of molecular structure such as II or III：
Wherein, Ar1、Ar2Independently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30 Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind or the two be interconnected cyclization；R is selected from substitution or not Substituted C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl in one kind；CY is selected from phenyl, naphthalene, anthryl, phenanthrene Base or pyrenyl.
Preferably, a kind of pyrene compound, general formula of molecular structure such as IV or V：
Wherein, Ra~RdIndependently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30's Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind；R is selected from substituted or unsubstituted C1~C10Alkyl, take Generation or unsubstituted C6~C30Aryl in one kind；CY is selected from phenyl, naphthalene, anthryl, phenanthryl or pyrenyl.
Preferably, CY is selected from naphthalene, anthryl, phenanthryl or pyrenyl.
Preferably, the Ar1、Ar2Independently selected from one kind in lower structure：
Wherein, R1~R7Independently selected from hydrogen, substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C1~ C10Alkoxy, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind；More Preferably, R1~R7Independently selected from hydrogen, methyl, methoxyl group, ethyl, isopropyl, tertiary butyl, cyclohexyl, phenyl, naphthalene, phenanthrene Base, anthryl, pyrenyl, base, indenyl, triphenylene, furyl, thienyl, pyrrole radicals, dibenzofurans, dibenzothiophenes, click Oxazolyl, fluorenyl, two fluorenyl of spiral shell, acridinyl, phenothiazinyl, phenoxazine groups or indyl；R8~R11Independently selected from substitution or not Substituted C1~C10Alkyl, substituted or unsubstituted C1~C10Alkoxy, substituted or unsubstituted C6~C30Aryl in One kind；It is furthermore preferred that R8~R11Independently selected from methyl, methoxyl group, ethyl, isopropyl, tertiary butyl, cyclohexyl, phenyl or Naphthalene；A is selected from 0~3 integer.
Further preferably, a kind of pyrene compound, any one in chemical constitution as follows：
A kind of pyrene compound of the present invention, preparation route are started with dibromo pyrene, are coupled with imidazoles class formation via C-C Intermediate 1 is obtained by the reaction, centre 1 obtains target product compound I, the master being related to tertiary aromatic amine structure via C-N coupling reactions Want compound as follows：
The present invention special limitation no to above-mentioned reaction is using popular response well-known to those skilled in the art Can, the preparation method is easy to operate, is readily produced.
The present invention also provides a kind of organic luminescent devices, including first electrode, second electrode and are placed in two electrode Between one or more organic compound layers, organic compound layer include hole injection layer, hole transmission layer, electronic blocking Layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer at least one layer；At least one in the organic compound layer Layer includes a kind of pyrene compound of the present invention.
Preferably, a kind of pyrene compound can be as the emitting layer material in organic luminescent device.The device of use Part structure is preferably specially：NPB is used as hole transmission layer substance, and AND is used as main substance, and the pyrene compound is used as mixing Miscellaneous material, TPBi is used as electron-transporting material, to manufacture the organic luminescent device of construction same as below：ITO/NPB/AND: Pyrene compound (doping concentration 5wt%)/TPBi/LiF/Al of the present invention.The organic electroluminescence device can be used for tablet The application fields such as display, lighting source, direction board, signal lamp.
The synthesis of [embodiment 1] compound A2
The synthesis of intermediate 1
Under the protection of nitrogen, anhydrous THF solution 15mL, magnesium rod (1.44g, 0.06mol), iodine are added in into there-necked flask 1, after grignard reagent causes, the anhydrous THF solution 50mL of 1,6- dibromos pyrene (17.9g, 0.05mol) is added in, under ice-water bath Reaction 3 hours after the anhydrous n,N-Dimethylformamide of 4.2mL then is added dropwise into reaction solution, is slowly ramped to room temperature, continues anti- It reacts and stops after answering 3 hours.1M hydrochloric acid is added in, the extraction of 100mL ethyl acetate has been cleaned successively with distilled water, saturated salt solution Machine layer, merges organic phase and drying, and concentration column chromatography obtains 6- bromine pyrene -1- formaldehyde (12.3g, yield 80%).
Under the protection of nitrogen, to 6- bromine pyrene -1- formaldehyde (2.6g, 8.6mmol), pyrene -4,5- diketone (2.3g, 9.9mmol), ammonium acetate (2.59g, 33.6mmol) and acetic acid (60mL) are added in the mixture of aniline (3.4g, 42.9mmol), It is heated to flowing back.After 2 hours, mixture is cooled down and is filtered.Filter cake is dissolved with chloroform, is then concentrated column chromatography and is obtained intermediate 1 (3.8g, yield 75%).
Mass spectrum m/z：596.05 (calculated values：596.09).Theoretical elemental content (%) C39H21BrN2：C,78.40；H, 3.54；Br,13.37；N, 4.69 actual measurement constituent contents (%)：C,78.42；H,3.55；Br,13.35；N,4.68.The above results Confirm that it is target product to obtain product.
The synthesis of compound A2
By tri-tert-butylphosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g, 1.83mmol) and sodium tert-butoxide (22.8g, 238mmol) is added to diphenylamines (31.6g, 187mmol) and intermediate 1 The solution of (109.0g, 183mmol) in degassed toluene (1L), and the mixture is heated 2 hours under reflux.This is anti- Mixture is answered to be cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and is carried with toluene It takes, and merges organic phase, it is evaporated under vacuum.The residue is filtered, and recrystallize via silica gel. To compound A2 (100.3g, yield 80%).
Mass spectrum m/z：685.23 (calculated values：685.25).Theoretical elemental content (%) C51H31N3：C,89.32；H,4.56； N, 6.13 actual measurement constituent contents (%)：C,89.31；H,4.55；N,6.14.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 2] compound A13
Change the aniline in the synthesis of 1 intermediate 1 of embodiment into equimolar 3- aminodiphenyls and furans, other steps are equal It is identical with the synthesis of embodiment 1, obtain target product compound A13.Mass spectrum m/z：775.23 (calculated values：775.26).It is theoretical Constituent content (%) C57H33N3O：C,88.24；H,4.29；N,5.42；O, 2.06 actual measurement constituent contents (%)：C,88.22；H, 4.29；N,5.43；O,2.06.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 3] compound A24
Change the diphenylamines in the synthesis of 1 compound A2 of embodiment into equimolar 9H- carbazoles, other steps with implementation The synthesis of example 1 is identical, obtains target product compound A24.Mass spectrum m/z：683.27 (calculated values：683.24).Theoretical elemental contains Measure (%) C51H29N3：C,89.58；H,4.27；N, 6.15 actual measurement constituent contents (%)：C,89.59；H,4.26；N,6.15.It is above-mentioned As a result confirm that it is target product to obtain product.
The synthesis of [embodiment 4] compound A-13 9
Change the aniline in the synthesis of 1 intermediate 1 of embodiment into equimolar 1- amino naphthalenes, 1,6- dibromo pyrene, which changes into, etc. rubs Your 2,7- dibromo pyrenes, other steps are identical with the synthesis of embodiment 1, obtain target product compound A-13 9.Mass spectrum m/z： 735.21 (calculated values：735.27).Theoretical elemental content (%) C55H33N3：C,89.77；H,4.52；N, 5.71 actual measurement elements contain It measures (%)：C,89.75；H,4.53；N,5.72.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 5] compound A47
Change the aniline in the synthesis of 1 intermediate 1 of embodiment into bromo- 9, the 9- dimethyl fluorenes of equimolar 2-, 1,6- dibromo Pyrene changes equimolar 2,7- dibromos pyrene into, other steps are identical with the synthesis of embodiment 1, obtains target product compound A47. Mass spectrum m/z：801.21 (calculated values：801.31).Theoretical elemental content (%) C60H39N3：C,89.86；H,4.90；N, 5.24 is real Survey constituent content (%)：C,89.85；H,4.92；N,5.23.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 6] compound A-45 8
Change 1, the 6- dibromo pyrenes in the synthesis of 1 intermediate 1 of embodiment into equimolar 2,7- dibromos pyrene, other steps are equal Identical with the synthesis of embodiment 1, the diphenylamines in compound A2 synthesis changes equimolar 9,10- dihydros -9,9- dimethyl a word used for translation into Pyridine, other steps are identical with the synthesis of embodiment 1, obtain target product compound A-45 8.Mass spectrum m/z：725.21 (calculated values： 725.28).Theoretical elemental content (%) C54H35N3：C,89.35；H,4.86；N, 5.79 actual measurement constituent contents (%)：C,89.36； H,4.86；N,5.77.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 7] compound B2
The synthesis of intermediate 2
Under the protection of nitrogen, to 6- bromine pyrene -1- formaldehyde (2.6g, 8.6mmol), phenanthrenequione (2.0g, 9.9mmol), aniline Ammonium acetate (2.59g, 33.6mmol) and acetic acid (60mL) are added in the mixture of (3.4g, 42.9mmol), is heated to flowing back.2 After hour, mixture is cooled down and is filtered.Filter cake is dissolved with chloroform, is then concentrated column chromatography and is obtained intermediate 2 (3.9g, yield are 80%).
Mass spectrum m/z：572.05 (calculated values：572.09).Theoretical elemental content (%) C37H21BrN2：C,77.49；H, 3.69；Br,13.93；N, 4.88 actual measurement constituent contents (%)：C,77.49；H,3.68；Br,13.95；N,4.88.The above results Confirm that it is target product to obtain product.
The synthesis of compound B2
By tri-tert-butylphosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g, 1.83mmol) and sodium tert-butoxide (22.8g, 238mmol) is added to diphenylamines (31.6g, 187mmol) and intermediate 2 The solution of (104.7g, 183mmol) in degassed toluene (1L), and the mixture is heated 2 hours under reflux.This is anti- Mixture is answered to be cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and is carried with toluene It takes, and merges organic phase, it is evaporated under vacuum.The residue is filtered, and recrystallize via silica gel. To compound B2 (96.7g, yield 80%).
Mass spectrum m/z：661.23 (calculated values：661.25).Theoretical elemental content (%) C49H31N3：C,88.93；H,4.72； N, 6.35 actual measurement constituent contents (%)：C,88.93；H,4.73；N,6.34.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 8] compound B34
Change 1, the 6- dibromo pyrenes in the synthesis of 7 intermediate 2 of embodiment into equimolar 2,7- dibromos pyrene, other steps are equal It is identical with the synthesis of embodiment 1, obtain target product compound B34.Mass spectrum m/z：661.23 (calculated values：661.25).It is theoretical Constituent content (%) C49H31N3：C,88.93；H,4.72；N, 6.35 actual measurement constituent contents (%)：C,88.93；H,4.73；N, 6.34.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 9] compound C11
Change the aniline in the synthesis of 1 intermediate 1 of embodiment into equimolar N- phenyl -9H- carbazoles, pyrene -4,5- diketone Change equimolar beta-naphthoquinone into, other steps are identical with the synthesis of embodiment 1, obtain target product compound C11.Mass spectrum m/ z：776.23 (calculated values：776.29).Theoretical elemental content (%) C57H36N4：C,88.12；H,4.67；N, 7.21 actual measurement elements Content (%)：C,88.12；H,4.65；N,7.23.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 10] compound C51
The synthesis of intermediate 3
100mL THF are added in into the there-necked flask equipped with 2,7- dibromos pyrene (15.2g, 42.4mmol), nitrogen is protected, and -78 DEG C stirring 30 minutes, then add in 21mL n-BuLis (2.5M), react 1 hour, add triisopropyl borate ester 14g, low temperature Reaction 1 hour, gradually restores room temperature.Last handling process, 2M hydrochloric acid is added in system makes solution pH value stand liquid separation, water for 4-5 Layer is extracted with ethyl acetate, and merges organic layer, is spin-dried for, obtains intermediate 3 (10.1g, yield 80%).
The synthesis of compound a
By tri-tert-butylphosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g, 1.83mmol) and sodium tert-butoxide (22.8g, 238mmol) is added to the bromo- 1H- benzimidazoles (36.0g, 183mmol) of 2- and to first Solution of the methoxyl bromobenzene (35.0g, 187mmol) in degassed toluene (1L), and it is small that the mixture is heated 2 under reflux When.The reaction mixture is cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and It is extracted with toluene, and merges organic phase, it is evaporated under vacuum.The residue is filtered via silica gel, and Recrystallization.Obtain compound a (44.2g, yield 80%).
Mass spectrum m/z：302.06 (calculated values：302.01).Theoretical elemental content (%) C14H11BrN2O：C,55.47；H, 3.66；Br,26.36；N,9.24；O, 5.28 actual measurement constituent contents (%)：C,55.47；H,3.65；Br,26.36；N,9.24；O, 5.29.The above results confirm that it is target product to obtain product.
The synthesis of compound b
By tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) added to intermediate 3 The solution of (59.3g, 183mmol) and compound a (55.2g, 183mmol) in degassing tetrahydrofuran (500mL), and should Mixture heats 4 hours under reflux.The reaction mixture is cooled to room temperature, rotation is except solvent later.Via silica gel column chromatography Obtain compound b (64.3g, theoretical value 70%).
Mass spectrum m/z：502.05 (calculated values：502.07).Theoretical elemental content (%) C30H19BrN2O：C,71.58；H, 3.80；Br,15.87；N,5.56；O, 3.18 actual measurement constituent contents (%)：C,71.56；H,3.83；Br,15.89；N,5.54；O, 3.18.The above results confirm that it is target product to obtain product.
The synthesis of compound C51
By tri-tert-butylphosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g, 1.83mmol) and sodium tert-butoxide (22.8g, 238mmol) added to compound b (91.9g, 183mmol) and diphenylamines (31.6g, 187mmol) the solution in degassed toluene (1L), and the mixture is heated 2 hours under reflux.By the reaction mixture It is cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and is extracted with toluene, and is closed And organic phase, it is evaporated under vacuum.The residue is filtered, and recrystallize via silica gel.Obtain compound C51 (86.5g, yield 80%).
Mass spectrum m/z：591.26 (calculated values：591.23).Theoretical elemental content (%) C42H29N3O：C,85.25；H,4.94； N,7.10；O, 2.70 actual measurement constituent contents (%)：C,85.23；H,4.94；N,7.12；O,2.71.The above results confirmation is produced Object is target product.
[comparison Application Example]
Transparent anode electrode ito substrate in isopropanol is cleaned by ultrasonic 15 minutes, and is exposed 30 minutes under ultraviolet light, Then handled 10 minutes with plasma.Then by treated, ito substrate is put into evaporated device.One layer of 70nm's of vapor deposition first NPB is as hole transmission layer, evaporation rate 0.1nm/s, followed by the vapor deposition of luminescent layer, mixing vapor deposition ADN/DPVBi, doping The TPBi of 50nm is then deposited as electron-transport in a concentration of 5wt%, evaporation rate 0.005nm/s, evaporation thickness 30nm Layer, evaporation rate 0.1nm/s, on the electron transport layer successively vacuum evaporation LiF and Al as cathode, thickness 200nm.
[Application Example]
Transparent anode electrode ito substrate in isopropanol is cleaned by ultrasonic 15 minutes, and is exposed 30 minutes under ultraviolet light, Then handled 10 minutes with plasma.Then by treated, ito substrate is put into evaporated device.One layer of 70nm's of vapor deposition first NPB is as hole transmission layer, evaporation rate 0.1nm/s, followed by the vapor deposition of luminescent layer, the pyrene of the mixing vapor deposition ADN/ present invention Class compound, doping concentration 5wt%, evaporation rate 0.005nm/s, evaporation thickness 30nm are then deposited 50nm's TPBi is as electron transfer layer, and evaporation rate 0.1nm/s, vacuum evaporation LiF and Al is used as the moon successively on the electron transport layer Pole, thickness 200nm.
The electron luminescence characteristic of the organic luminescent device of above method manufacture represents in the following table：
The above result shows that a kind of pyrene compound of the invention is applied in organic luminescent device, especially as hair Luminescent material shows the advantages of driving voltage is low, luminous efficiency is high, is luminous organic material of good performance.
Obviously, the explanation of above example is only intended to facilitate the understanding of the method and its core concept of the invention.It should refer to Go out, it, without departing from the principle of the present invention, can also be to this hair for the those of ordinary skill of the technical field Bright some improvement and modification can also be carried out, these improvement and modification are also fallen within the protection scope of the claims of the present invention.

Claims (8)

1. a kind of pyrene compound, which is characterized in that its general formula of molecular structure is as shown in I：
Wherein, Ar1、Ar2Independently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30Virtue Base, substituted or unsubstituted C3~C30Heteroaryl in one kind or the two be interconnected cyclization；R is selected from substitution or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C50Heteroaryl in one Kind；CY is substituted or unsubstituted C6~C30Aryl.
A kind of 2. pyrene compound according to claim 1, which is characterized in that its general formula of molecular structure such as II or III：
Wherein, Ar1、Ar2Independently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30Virtue Base, substituted or unsubstituted C3~C30Heteroaryl in one kind or the two be interconnected cyclization；R is selected from substitution or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl in one kind；CY be selected from phenyl, naphthalene, anthryl, phenanthryl or Pyrenyl.
3. a kind of pyrene compound according to claim 1, which is characterized in that its general formula of molecular structure such as IV or V：
Wherein, Ra~RdIndependently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30Virtue Base, substituted or unsubstituted C3~C30Heteroaryl in one kind；R is selected from substituted or unsubstituted C1~C10Alkyl, substitution Or unsubstituted C6~C30Aryl in one kind；CY is selected from phenyl, naphthalene, anthryl, phenanthryl or pyrenyl.
4. a kind of pyrene compound according to claim 1, which is characterized in that CY is selected from naphthalene, anthryl, phenanthryl or pyrene Base.
A kind of 5. pyrene compound according to claim 1, which is characterized in that Ar1、Ar2In with lower structure One kind：
Wherein, R1~R7Independently selected from hydrogen, substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C1~C10's Alkoxy, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind；R8~R11 Independently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C1~C10Alkoxy, substitution or do not take The C in generation6~C30Aryl in one kind；A is selected from 0~3 integer.
A kind of 6. pyrene compound according to claim 1, which is characterized in that appointing in chemical constitution as follows Meaning is a kind of：
7. a kind of organic luminescent device, which is characterized in that the organic luminescent device includes cathode, anode and is placed in two electricity One or more organic compound layers between pole, the organic compound layer contain claim 1~6 any one of them A kind of pyrene compound.
8. according to a kind of organic luminescent device described in claim 7, which is characterized in that the organic compound layer includes hair Photosphere contains a kind of pyrene compound of claim 1~6 any one of them in luminescent layer.
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020182070A1 (en) * 2019-03-08 2020-09-17 江苏三月光电科技有限公司 Compound using triarylamine containing pyrene or azapyrene as core and application thereof
CN113801066A (en) * 2020-08-25 2021-12-17 北京八亿时空液晶科技股份有限公司 Imidazole derivatives and use thereof
CN114507188A (en) * 2022-02-14 2022-05-17 季华恒烨(佛山)电子材料有限公司 Organic compound based on pyrene and benzimidazole, organic electroluminescent composition and organic electroluminescent device

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020182070A1 (en) * 2019-03-08 2020-09-17 江苏三月光电科技有限公司 Compound using triarylamine containing pyrene or azapyrene as core and application thereof
CN113801066A (en) * 2020-08-25 2021-12-17 北京八亿时空液晶科技股份有限公司 Imidazole derivatives and use thereof
CN113801066B (en) * 2020-08-25 2023-06-23 北京八亿时空液晶科技股份有限公司 Imidazole derivatives and uses thereof
CN114507188A (en) * 2022-02-14 2022-05-17 季华恒烨(佛山)电子材料有限公司 Organic compound based on pyrene and benzimidazole, organic electroluminescent composition and organic electroluminescent device
CN114507188B (en) * 2022-02-14 2023-08-11 季华恒烨(佛山)电子材料有限公司 Organic compound based on pyrene and benzimidazole, organic electroluminescent composition and organic electroluminescent device

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Application publication date: 20180629