CN108516960A - A kind of glyoxaline compound and its organic luminescent device - Google Patents

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

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CN108516960A
CN108516960A CN201810297287.7A CN201810297287A CN108516960A CN 108516960 A CN108516960 A CN 108516960A CN 201810297287 A CN201810297287 A CN 201810297287A CN 108516960 A CN108516960 A CN 108516960A
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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 glyoxaline compound and its organic luminescent devices, are related to organic optoelectronic materials technology.On the one hand, triphenylene 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 makes carrier transport balance.It is applied to organic luminescent device, is used especially as the blue dopant material in luminescent layer, device shows the advantage that driving voltage is low, luminous efficiency is high, is 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 glyoxaline compound and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical field more particularly to a kind of glyoxaline 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； (2) brightness is high, there is high contrast, pure in colour, the problem of almost without visible angle；(3) ultra-thin, by very thin organic Material coating and basis material are constituted, 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 At, 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 itself can obtain blue-light device as luminescent layer, 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 motor 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, construction unit of the imidazoles as a kind of novel blue light material, causes the extensive concern of researcher, such as The luminescent material what designs the new better imidazoles class formation of performance is adjusted, and is always that those skilled in the art are urgently to be resolved hurrily The problem of.
Invention content
The object of the present invention is to provide a kind of glyoxaline compound and its organic luminescent devices.Imidazoles provided by the invention Compound thermal stability is high, glass transition temperature is high, by the compound for manufactured organic luminescent device in luminescent layer, table Reveal the advantage that driving voltage is low, luminous efficiency is high, is the luminous organic material of function admirable.
The present invention provides a kind of glyoxaline compounds, and general formula of molecular structure is as shown in I：
Wherein, A is substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C2~C30Amino, substitution or Unsubstituted C3~C30Heteroaryl in one kind；R is selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C50Heteroaryl in one kind；CY is substituted or unsubstituted C6~C30's Aryl.
Preferably, the A is the C of substitution2~C30Amino, substituted or unsubstituted C3~C30Heteroaryl in one Kind；R is selected from substituted or unsubstituted C1~C10Alkyl, substituted 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, a kind of glyoxaline compound, general formula of molecular structure is as shown in II, III or IV：
Wherein, Ar1、Ar2Independently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30 Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind；Ra~RdIndependently selected from substituted or unsubstituted C1~ C10Alkyl, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind；R is selected From substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl in one kind；CY is selected from naphthalene, anthracene Base, 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 glyoxaline compound in chemical constitution as follows：
The present invention also provides 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, the organic compound layer contains a kind of imidazoles chemical combination of any one of them Object.
Preferably, organic compound layer includes luminescent layer, contains a kind of imidazoles chemical combination of any one of them in luminescent layer Object.
Beneficial effects of the present invention：
The present invention provides a kind of glyoxaline compounds, on the one hand, triphenylene structure because of its higher triplet and Wider energy gap shows the blue light performance haveing excellent performance；On the other hand, in molecule by connect benzimidazole, naphtho- imidazoles, Phenanthro- imidazoles or pyridine imidazole group, increase the electron transport ability of structure, by connecting tertiary aromatic amine structure, enhance structure Cavity transmission ability, the combination of the two makes carrier transport balance.It is applied to organic luminescent device, especially as Blue dopant material in luminescent layer uses, and device shows the advantage that driving voltage is low, luminous efficiency is high, common better than existing OLED device.The good application effect shown in OLED luminescent devices, this point show it with good industrialization Foreground.
Specific implementation mode：
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 The every other embodiment that personnel are 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 refer to aromatic hydrocarbon molecule aromatic core carbon on remove a hydrogen atom after, be left univalent perssad it is total 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 Pheno base, benzofuranyl, dibenzofuran group, dibenzothiophene, carbazyl etc., but not limited to this.
Amino of the present invention refers to being made of a nitrogen-atoms and two hydrogen atoms, chemical formula-NH2, can be alkane Amino or aryl amine, example may include-N (CH3)2、-N(CH2CH3)2With such as lower structure, but not limited to this
The present invention provides a kind of glyoxaline compounds, and general formula of molecular structure is as shown in I：
Wherein, A is substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C2~C30Amino, substitution or Unsubstituted C3~C30Heteroaryl in one kind；R is selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C50Heteroaryl in one kind；CY is substituted or unsubstituted C6~C30's Aryl.
According to the present invention, the substituted alkyl, substituted aryl, substituted heterocycle, the independent choosing of substituent group 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, the A is the C of substitution2~C30Amino, substituted or unsubstituted C3~C30Heteroaryl in one Kind；R is selected from substituted or unsubstituted C1~C10Alkyl, substituted 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, a kind of glyoxaline compound, general formula of molecular structure is as shown in II, III or IV：
Wherein, Ar1、Ar2Independently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30 Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind；Ra~RdIndependently selected from substituted or unsubstituted C1~ C10Alkyl, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind；R is selected From substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl in one kind；CY is selected from naphthalene, anthracene Base, 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 glyoxaline compound, any one in chemical constitution as follows：
A kind of glyoxaline compound of the present invention, preparation route is started with 2,7- dibromo triphenylenes, with imidazoles class formation Intermediate 1 is obtained via C-C coupling reactions, centre 1 obtains mesh with tertiary aromatic amine structure, 9H- carbazole structures or acridine structural response Product Compound I is marked, the main compound being related to is as follows：
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 easy to operate, is readily produced.
The present invention also provides 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, organic compound layer include hole injection layer, hole transmission layer, electronic blocking At least one layer of layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer；At least one in the organic compound layer Layer includes a kind of glyoxaline compound of the present invention.
Preferably, a kind of glyoxaline compound can be used as the emitting layer material in organic luminescent device.It uses Device architecture is preferably specially：2-TNATA is used as hole injection layer substance, and NPB is used as hole transmission layer substance, the imidazoles Class compound is used as luminescent layer main substance, adulterates the Ir (PPy) of 5wt%3, Alq3As electron-transporting material, to have manufactured The organic luminescent device of construction same as below：ITO/2-TNATA/NPB/ glyoxaline compounds of the present invention:Ir(PPy)3(doping is dense Degree is 5wt%)/Alq3/LiF/Al.The organic electroluminescence device can be used for flat-panel monitor, lighting source, direction board, The application fields such as 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 into there-necked flask 1, after grignard reagent causes, the anhydrous THF solution 50mL of 2,7- dibromos triphenylene (19.1g, 0.05mol) is added, in ice water The lower reaction of bath 3 hours, after the anhydrous n,N-Dimethylformamide of 4.2mL then is added dropwise into reaction solution, is slowly ramped to room temperature, after Continuous reaction is reacted after 3 hours to be stopped.1M hydrochloric acid is added, the extraction of 100mL ethyl acetate uses distilled water, saturated salt solution clear successively Organic layer is washed, organic phase and drying are merged, concentration column chromatography obtains 7- bromine triphenylene -2- formaldehyde (13.4g, yield 80%).
Under the protection of nitrogen, to 7- bromine triphenylene -2- formaldehyde (2.9g, 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 cooling and filters.Filter cake is dissolved with chloroform, is then concentrated column chromatography and is obtained intermediate 1 (4.0g, yield 75%).
Mass spectrum m/z：622.05 (calculated values：622.10).Theoretical elemental content (%) C41H23BrN2：C,78.97；H, 3.72；Br,12.81；N, 4.49 actual measurement constituent contents (%)：C,78.98；H,3.72；Br,12.83；N,4.47.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 (113.8g, 183mmol) in degassed toluene (1L), and the mixture is heated 2 hours under reflux.This is anti- It answers mixture to be cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, toluene is used in combination to carry It takes, and merges organic phase, it is evaporated under vacuum.The residue is filtered via silica gel, and is recrystallized. To compound A2 (104.1g, yield 80%).
Mass spectrum m/z：711.23 (calculated values：711.27).Theoretical elemental content (%) C53H33N3：C,89.42；H,4.67； N, 5.90 actual measurement constituent contents (%)：C,89.43；H,4.66；N,5.91.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 as the synthesis of embodiment 1, obtain target product compound A13.Mass spectrum m/z：801.23 (calculated values：801.28).It is theoretical Constituent content (%) C59H35N3O：C,88.37；H,4.40；N,5.24；O, 2.00 actual measurement constituent contents (%)：C,88.35；H, 4.42；N,5.21；O,2.02.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：709.27 (calculated values：709.25).Theoretical elemental contains Measure (%) C53H31N3：C,89.68；H,4.40；N, 5.92 actual measurement constituent contents (%)：C,89.66；H,4.42；N,5.92.It is above-mentioned As a result confirm that it is target product to obtain product.
The synthesis of [embodiment 4] compound A27
Change the diphenylamines in the synthesis of 1 compound A2 of embodiment into equimolar phenoxazine, other steps with implementation The synthesis of example 1 is identical, obtains target product compound A27.Mass spectrum m/z：725.22 (calculated values：725.25).Theoretical elemental contains Measure (%) C53H31N3O：C,87.70；H,4.30；N,5.79；O, 2.20 actual measurement constituent contents (%)：C,87.72；H,4.31；N, 5.76；O,2.21.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 5] compound B2
The synthesis of intermediate 2
Under the protection of nitrogen, to 7- bromine triphenylene -2- formaldehyde (2.9g, 8.6mmol), phenanthrenequione (2.0g, 9.9mmol), Ammonium acetate (2.59g, 33.6mmol) and acetic acid (60mL) are added in the mixture of aniline (3.4g, 42.9mmol), is heated to back Stream.After 2 hours, mixture is cooling and filters.Filter cake is dissolved with chloroform, is then concentrated column chromatography and is obtained intermediate 2 (8.1g, production 80%) rate is.
Mass spectrum m/z：598.05 (calculated values：598.10).Theoretical elemental content (%) C39H23BrN2：C,78.13；H, 3.87；Br,13.33；N, 4.67 actual measurement constituent contents (%)：C,78.13；H,3.86；Br,13.34；N,4.67.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 (109.4g, 183mmol) in degassed toluene (1L), and the mixture is heated 2 hours under reflux.This is anti- It answers mixture to be cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, toluene is used in combination to carry It takes, and merges organic phase, it is evaporated under vacuum.The residue is filtered via silica gel, and is recrystallized. To compound B2 (54.7g, yield 80%).
Mass spectrum m/z：687.23 (calculated values：687.27).Theoretical elemental content (%) C51H33N3：C,89.06；H,4.84； N, 6.11 actual measurement constituent contents (%)：C,89.04；H,4.83；N,6.13.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 6] compound B-11 9
Change the diphenylamines in 5 compound B2 synthesis of embodiment into equimolar N- phenyl-1-naphthylamines, other steps with The synthesis of embodiment 1 is identical, obtains target product compound B-11 9.Mass spectrum m/z：737.23 (calculated values：737.28).Theoretical member Cellulose content (%) C55H35N3：C,89.52；H,4.78；N, 5.69 actual measurement constituent contents (%)：C,89.54；H,4.79；N,5.67. The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 7] 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 as the synthesis of embodiment 1, obtain target product compound C11.Mass spectrum m/ z：802.33 (calculated values：802.31).Theoretical elemental content (%) C59H38N4：C,88.25；H,4.77；N, 6.98 actual measurement elements Content (%)：C,88.26；H,4.77；N,6.97.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 8] compound C23
The synthesis of compound a
100mL THF are added into the there-necked flask equipped with 2,7- dibromos triphenylene (16.2g, 42.4mmol), nitrogen is protected Shield, -78 DEG C are stirred 30 minutes, and 21mL n-BuLis (2.5M) are then added, reacts 1 hour, adds triisopropyl borate ester 14g, low-temp reaction 1 hour, gradually restores room temperature.Last handling process, 2M hydrochloric acid is added in system makes solution pH value be 4-5, quiet Liquid separation is set, aqueous layer with ethyl acetate extraction merges organic layer, is spin-dried for, obtains compound a (11.8g, yield 80%).
The synthesis of compound b
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 2- bromines Solution of the triphenylene (57.2g, 187mmol) in degassed toluene (1L), and the mixture is heated 2 hours under reflux. The reaction mixture is cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, first is used in combination Benzene extracts, and merges organic phase, it is evaporated under vacuum.The residue is filtered via silica gel, knot of laying equal stress on It is brilliant.Obtain compound b (57.9g, yield 75%).
Mass spectrum m/z：422.06 (calculated values：422.04).Theoretical elemental content (%) C25H15BrN2：C,70.93；H, 3.57；Br,26.36；N, 18.88 actual measurement constituent contents (%)：C,70.93；H,3.58；Br,26.37；N,18.82.Above-mentioned knot Fruit confirms that it is target product to obtain product.
The synthesis of intermediate 3
Tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to intermediate 3 The solution of (59.3g, 183mmol) and compound a (77.2g, 183mmol) in degassing tetrahydrofuran (500mL), and should Mixture heats 4 hours under reflux.The reaction mixture is cooled to room temperature, rotation later removes solvent.Via silica gel column chromatography Obtain intermediate 3 (83.0g, theoretical value 70%).
Mass spectrum m/z：648.05 (calculated values：648.12).Theoretical elemental content (%) C43H25BrN2：C,79.51；H, 3.88；Br,12.30；N, 4.31 actual measurement constituent contents (%)：C,79.51；H,3.87；Br,12.31；N,4.31.The above results Confirm that it is target product to obtain product.
The synthesis of compound C23
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 compound b (118.5g, 183mmol) and diphenylamines The solution of (31.6g, 187mmol) in degassed toluene (1L), and the mixture is heated 2 hours under reflux.This is anti- It answers mixture to be cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, toluene is used in combination to carry It takes, and merges organic phase, it is evaporated under vacuum.The residue is filtered via silica gel, and is recrystallized. To compound C23 (86.5g, yield 80%).
Mass spectrum m/z：737.26 (calculated values：737.28).Theoretical elemental content (%) C55H35N3：C,89.52；H,4.78； N, 5.69 actual measurement constituent contents (%)：C,89.53；H,4.78；N,5.68.The above results confirm that it is target product to obtain product.
[comparison Application Example]
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and is exposed 30 minutes under ultraviolet light, Then handled 10 minutes with plasma.Then by treated, ito substrate is put into evaporated device.The 2- of one layer of 10nm is deposited first Then TNATA is deposited the NPB of one layer of 40nm as hole transmission layer, steams as hole injection layer, evaporation rate 0.1nm/s Plating rate is 0.1nm/s, then is the vapor deposition of luminescent layer, mixing vapor deposition CBP/Ir (PPy)3, doping concentration 5wt%, vapor deposition speed Rate is 0.005nm/s, evaporation thickness 30nm, and the Alq of 50nm is then deposited3As electron transfer layer, evaporation rate is 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 is cleaned by ultrasonic 15 minutes in isopropanol, and is exposed 30 minutes under ultraviolet light, Then handled 10 minutes with plasma.Then by treated, ito substrate is put into evaporated device.The 2- of one layer of 10nm is deposited first Then TNATA is deposited the NPB of one layer of 40nm as hole transmission layer, steams as hole injection layer, evaporation rate 0.1nm/s Plating rate is 0.1nm/s, then is the vapor deposition of luminescent layer, glyoxaline compound/Ir (PPy) of the mixing vapor deposition present invention3, adulterate dense Degree is 5wt%, evaporation rate 0.005nm/s, evaporation thickness 30nm, and the Alq of 50nm is then deposited3As electron-transport Layer, evaporation rate 0.1nm/s, on the electron transport layer successively vacuum evaporation LiF and Al as cathode, thickness 200nm.
The electron luminescence characteristic of the organic luminescent device of above method manufacture indicates in the following table：
The above result shows that a kind of glyoxaline compound of the invention is applied in organic luminescent device, especially as Luminescent material shows the advantage that 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 glyoxaline compound, which is characterized in that its general formula of molecular structure is as shown in I：
Wherein, A is substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C2~C30Amino, substitution or do not take The C in generation3~C30Heteroaryl in one kind；R is selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~ C30Aryl, substituted or unsubstituted C3~C50Heteroaryl in one kind；CY is substituted or unsubstituted C6~C30Aryl.
2. a kind of glyoxaline compound according to claim 1, which is characterized in that A is the C of substitution2~C30Amino, take Generation or unsubstituted C3~C30Heteroaryl in one kind；R is selected from substituted or unsubstituted C1~C10Alkyl, substitution or do not take The C in generation6~C30Aryl in one kind；CY is selected from phenyl, naphthalene, anthryl, phenanthryl or pyrenyl.
3. a kind of glyoxaline compound according to claim 1, which is characterized in that CY is selected from naphthalene, anthryl, phenanthryl or pyrene Base.
4. a kind of glyoxaline compound according to claim 1, which is characterized in that its general formula of molecular structure such as II, III or Shown in IV：
Wherein, Ar1、Ar2Independently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30Virtue Base, substituted or unsubstituted C3~C30Heteroaryl in one kind；Ra~RdIndependently selected from substituted or unsubstituted C1~C10's Alkyl, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind；R is selected from and takes Generation or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl in one kind；CY be selected from naphthalene, anthryl, Phenanthryl or pyrenyl.
5. a kind of glyoxaline compound according to claim 1, which is characterized in that Ar1、Ar2Independently selected from lower structure In 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.
6. a kind of glyoxaline compound according to claim 1, which is characterized in that in chemical constitution as follows Any one：
7. 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 One or more organic compound layers between pole, the organic compound layer contain claim 1~6 any one of them A kind of glyoxaline 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 glyoxaline compound of claim 1~6 any one of them in luminescent layer.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111675693A (en) * 2020-05-20 2020-09-18 华南理工大学 D-A type luminous micromolecules containing acridine and phenanthroimidazole and application thereof in electroluminescent device
WO2021176096A1 (en) 2020-03-05 2021-09-10 Krka, D.D., Novo Mesto Pharmaceutical composition comprising sglt2 inhibitor
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

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021176096A1 (en) 2020-03-05 2021-09-10 Krka, D.D., Novo Mesto Pharmaceutical composition comprising sglt2 inhibitor
CN111675693A (en) * 2020-05-20 2020-09-18 华南理工大学 D-A type luminous micromolecules containing acridine and phenanthroimidazole and application thereof in electroluminescent device
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

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