CN109824672A - A kind of quinazo triazole derivatives and its application in field of organic electroluminescence - Google Patents
A kind of quinazo triazole derivatives and its application in field of organic electroluminescence Download PDFInfo
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Abstract
The invention discloses quinazo triazole derivatives shown in formula (1) and its applications in luminous organic material, the compound of the present invention realizes good electron injection and transporting, the compound of the present invention electron mobility with higher, when being applied in OLED device, the operating voltage for advantageously reducing device improves the luminous efficiency of device.
Description
Technical field
A new class of spread out the present invention relates to a kind of new organic heterocyclic molecule more particularly to containing quinazo triazole
Biology, and its application in organic electroluminescence device.
Background technique
Now with OLED technology in the continuous propulsion for illuminating and showing two big fields, people grind for its core material
Study carefully and focus more on, the excellent in efficiency service life organic electroluminescence device of length is usually device architecture and various organic materials
Optimize arranging in pairs or groups as a result, this functionalization material for just designing and developing various structures for chemists provides greatly opportunity and chooses
War.Common functionalization organic material has: hole-injecting material, hole mobile material, hole barrier materials, electron injection material
Material, electron transport material, electron-blocking materials and light emitting host material and light-emitting guest (dyestuff) etc..More for processability
Good luminescent device, industry have been devoted to develop luminous efficiency of the new electroluminescent organic material to further increase device
And the service life.
By years of researches and development, electroluminescent organic material and device have had reached practical level, hole
Transmission material, electron transport material, luminescent material, display device technology of preparing etc. have been achieved for considerable progress.Equally
Ground, transmittability is stronger, the higher all types of electron transport materials of stability, all has been reported that in previous article and patent.
In general, electron transport material is all the compound with the nitrogen-containing heterocycle group of electron deficient, they are mostly with higher
Electron affinity, thus have it is stronger connect nucleophobic ability, but relative to hole mobile material, common electron-transport material
The electron mobility of material such as AlQ3(8-hydroxyquinoline aluminum) will be far below hole mobile material hole mobility, thus
On the one hand will lead in OLED device carrier injection and transmission it is unbalanced caused by the recombination probability of hole and electronics drop
Low, to reduce the luminous efficiency of device, on the other hand the electron transport material with lower electron mobility will lead to device
Operating voltage increase, it is unfavorable to the saving of the energy to influence power efficiency.
In current OLED screen body manufacturer, the skill in ET material layer widely is doped to using Liq (8-hydroxy-quinoline lithium)
Art means, the low-voltage and high efficiency of Lai Shixian device, and it is improved the effect of device lifetime, Liq (8-hydroxy-quinoline lithium)
Effect essentially consist in can cathode injected electrons effect under restore micro lithium metal, to play to electron-transport
Material carries out the effect of n- doping so that the injection significant effect of electronics promotes, another aspect, lithium ion can by with electricity
The coordination of N atom in sub- transmission material plays the role of improving ET material electronics mobility, so that Liq (eight hydroxyls
Quinoline lithium) device of ET is adulterated with low operating voltage and high luminous efficiency.
International Patent Publication No. WO2006/049013 discloses a kind of chemical combination for using thick bicyclic radicals as skeleton structure
Object；U.S. Patent number 8,227,798B2 and South Korea patent application special open 10-2010-0108924 disclose a kind of compound,
Wherein nitrogenous heteroaryl such as triazine is bonded on dibenzo-carbazole nitrogen-atoms as organic electroluminescent compounds；Korean Patent
Number 10-1074193 discloses a kind of compound, wherein nitrogenous heteroaryl such as triazine is bonded on the nitrogen-atoms of benzo carbazole and makees
For organic electroluminescent compounds；International Patent Publication No. WO2012/121561 discloses a kind of compound, wherein nitrogenous heteroaryl
Base such as quinazoline is bonded on carbazole derivates nitrogen-atoms as organic electroluminescent compounds.However, above-mentioned bibliography
A kind of organic electroluminescent compounds are not disclosed particularly, wherein quinazo triazole introduces main body as short of electricity subbase group
In material structure.
In conclusion the demand and mobile that are constantly promoted for photoelectric properties of the further satisfaction to OLED device
Electronic device needs constantly to develop novel, efficient OLED material for energy-efficient demand, wherein exploitation it is new there is height
The electron transport material tool of mobility has very important significance.Summary of the invention
This is to solve the above problems, the present invention provides a kind of novel compound for organic electroluminescence device.The change
Object is closed by introducing quinazo triazole structure, realizes good electronic transmission performance.Specifically,
The present invention provides a kind of compound, the structure of a kind of compound, compound is indicated by following general formula (I),
Wherein:
L1And L2It is independent to be selected from singly-bound ,-O- ,-S- ,-NRa, C1-C5 alkylidene, (C1-C3 alkylidene)-O- (C1-
C3 alkylidene), the aryl of C6-C30, C3-C30 heteroaryl；
R1It is independent selected from H, substituted or unsubstituted C1~C12 alkyl, C1~C12 alkoxy, halogen, cyano, nitro,
Hydroxyl, silylation, the substituted or unsubstituted aryl of C6~C30, C3~C30 substituted or unsubstituted heteroaryl；R3's
Quantity is 1,2,3,4, works as R1Quantity be 2 or more when, R1It is same or different；
Ar1And Ar2It is independent selected from H, substituted or unsubstituted C1~C12 alkyl, C1~C12 alkoxy, halogen, cyano,
Nitro, hydroxyl, silylation, the substituted or unsubstituted aryl of C6~C30, C3~C30 substituted or unsubstituted heteroaryl；
Wherein Ar1And Ar2In at least one be substituted or unsubstituted fused-aryl, 2 or more phenyl ring are contained in the fused-aryl
The fused rings or R of formation1、Ar1And Ar2It is simultaneously phenyl.
In a preferred embodiment of the present invention, wherein Ar1And Ar2In at least one to be substituted or unsubstituted thick
Aryl is closed, the fused rings that the phenyl ring in the fused-aryl containing 2 or more is formed；And the fused-aryl with thereon
Substituent group either forms conjugatedπbond with the L1 or L2 for being connected to it, includes at least four phenyl ring in the conjugatedπbond, or
It includes at least three phenyl ring in conjugatedπbond that fused-aryl described in person, which is formed by itself,.
In a preferred embodiment of the present invention, at least one of described Ar1 and Ar2, which is selected from, replaces or does not take
Naphthalene, anthryl, fluoranthene base, fluorenyl, phenanthryl, pyrenyl, benzo anthryl, the benzo pyrenyl in generation；The substituent group is 1,2,3,4 only
It is vertical selected from H, substituted or unsubstituted C1~C12 alkyl, C1~C12 alkoxy, halogen, cyano, nitro, hydroxyl, silylation,
The substituted or unsubstituted heteroaryl of the substituted or unsubstituted aryl of C6~C18, C3~C11, the substituent group it is identical or
Person is different.
In a preferred embodiment of the present invention, the Ar1And Ar2At least one of for naphthalene or formula (II) institute
The group shown, wherein * indicates connection site, formula (II) it is optional by 1,2,3,4 it is independent selected from H, it is substituted or unsubstituted
C1~C12 alkyl, C1~C12 alkoxy, phenyl, halogen, cyano, nitro, hydroxyl substituent group replaced, the substitution base phase
It is same or different；Wherein Ar3Selected from selected from H, substituted or unsubstituted C1~C12 alkyl, C1~C12 alkoxy, halogen, cyanogen
Base, nitro, hydroxyl, the substituted or unsubstituted aryl of C6~C12, C3~C11 substituted or unsubstituted heteroaryl；Work as formula
(II) there are two Ar in3When, two Ar3It is same or different；
In a preferred embodiment of the present invention, the L1 and L2It is independently singly-bound, phenyl, furyl, thiophene
Base, pyrrole radicals, pyridyl group, xenyl, terphenyl or naphthalene.
In a preferred embodiment of the present invention, the Ar3It is independent to be selected from hydrogen, phenyl, naphthalene, furyl, thiophene
Pheno base, pyrrole radicals, pyridyl group, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, indenyl, fluorenyl and its derivative, fluoranthene base,
Triphenylene, pyrenyl, base,Base, aphthacene base, triarylamine, 9,9- dimethyl fluorenyl, diphenylethyllene phenyl, benzo
Fluorenyl, indeno fluorenyl or indenyl.
In a preferred embodiment of the present invention, work as Ar1And Ar2In one of them for shown in naphthalene or formula (II)
Group when, another for hydrogen, phenyl, naphthalene, furyl, thienyl, pyrrole radicals, pyridyl group, xenyl, terphenyl,
Naphthalene, anthryl, phenanthryl, indenyl, fluorenyl and its derivative, fluoranthene base, triphenylene, pyrenyl, base,Base, aphthacene base, three
Aryl amine, 9,9- dimethyl fluorenyl, diphenylethyllene phenyl, benzo fluorenyl, indeno fluorenyl or indenyl.
The above-mentioned alkyl as C1~C12, the more preferably alkyl of C1~C4, preferably methyl, ethyl, isopropyl, ring
Hexyl；As the alkoxy of C1~C12, the more preferably alkoxy of C1~C4, methoxyl group, ethoxy can be enumerated as concrete example
Base, propoxyl group, isopropoxy etc..
It should be noted that in the present invention, the expression way of Ca~Cb represents the carbon atom number that the group has as a~b,
Unless specifically indicated, it is however generally that the carbon atom number does not include the carbon atom number of substituent group.
In the present invention, the statement for chemical element includes the concept of chemical property identical isotope, such as " hydrogen "
Statement also includes the concept of chemical property identical " deuterium ", " tritium ".
Hetero atom in the present invention is often referred to selected from B, N, O, S, P, P (=O), Si and atom or atomic group in Se.
In order to improve the electron injection and transmission performance of material, the group for selecting to have compared with the sub- affinity of forceful electric power is needed,
The group of common electron transport material includes the groups such as pyridine, quinoline, Phen, triazine, and the compound in the present invention is adopted
With a kind of novel group with the very sub- affinity of forceful electric power: quinazo triazole, Gaussian Computation obtain quinazo
The LUMO of triazole parent compound be about -1.651eV, significantly lower than common drawing electron group such as pyridine (-
0.61eV), the lumo energy of quinoline (- 1.38eV), Phen (- 1.41eV) shows that quinazo triazole group has
High electron affinity, is a kind of excellent drawing electron group, and the compound with such substituent group is infused with good electronics
Enter performance.There is extraordinary coplanar conjugated structure additionally, due to quinazo triazole, so that having such substituent group
π-π between group interaction can sufficiently occur in the solid state for the compound molecule of group, to be conducive to electronics in material point
Transmitting between son, so that this kind of material has very high electron mobility.This kind of material is applied to be conducive in OLED device
The operating voltage for reducing device, improves the luminous efficiency of device.
Compound in the present invention, the on the one hand high electron affinity as specific to precursor structure, thus with cathode material
The work function of material is more nearly, and allows the material to easily obtain electronics from cathode, has the sub- injection of forceful electric power；Another party
This material of face has very high electron mobility.In summary two o'clock, material of the present invention is in the case where exclusive use, it will be able to
Technical effect achieved by the common ET collocation QLi of industry is realized, to avoid taking using the QLi to water and environment sensitive
With conventional ET material, on the one hand reduce the use type of material on shielding scale of construction producing line in this way, advantageously reduce material at
This, on the other hand can reduce the evaporation source number of volume production equipment, to reduce the design and manufacture cost and complex process of equipment
Property, there is very big meaning.
Inventors have found that having most suitable when quinazo triazole compound is replaced by anthryl
HOMO, lumo energy, resulting compound are suitble to become electrons and holes transmission channel, and charge-transporting with higher
Can, this may be distributed in related in anthryl functional group with HOMO, LUMO.In addition, anthryl functional group can assign compound can
Inverse electrochemical redox characteristic, this makes the compounds of this invention containing anthryl functional group show excellent electron-transport
Performance, therefore the electron transport material as device is preferred.
The compound of the present invention can be applied in organic electronic device, organic electronic device such as organic electroluminescence
Part, illumination component, Organic Thin Film Transistors, organic field effect tube, organic thin film solar cell, information labels, electronics
Large area sensor, Electronic Paper and the organic EL panels such as artificial skin sheet material, sheet material type scanner etc..
The present invention also provides above-mentioned quinazo triazole derivatives to prepare the purposes in organic electroluminescence device.
Wherein, the quinazo triazole derivatives may be used as but be not limited to electron transport layer materials or luminescent layer material of main part.
Organic electroluminescence device structure of the invention and well known device have no difference, generally comprise first electrode, the
One or more layers organic layer between two electrodes and the insertion first electrode and second electrode, which is characterized in that described organic
Layer includes above-mentioned quinazo triazole derivatives.
As the organic layer between first electrode and second electrode, generally comprises electron injecting layer, electron transfer layer, shines
The organic layers such as layer, hole transmission layer, hole injection layer, the compound of the present invention may be used as but be not limited to electron transfer layer material
Material.
As the present invention relates to the preferred structure of compound can enumerate following compound, but be not limited to these chemical combination
Object.
The present invention provides a kind of quinazo triazole derivatives in organic electroluminescence device as electron-transport material
The application of material.
The present invention also provides a kind of organic electroluminescence devices, including substrate, and successively take shape on the substrate
Anode layer, organic layer and cathode layer；
The organic layer includes hole transmission layer, luminescent layer and electron transfer layer, and the organic luminous layer includes main body
Material and dopant dye, the electron transport layer materials or luminescent layer material of main part are derivative using the quinazo triazole
Object.
The substrate in conventional organic luminescence device can be used in organic electroluminescence device substrate of the invention, such as: glass
Glass or plastics are, it is preferable to use glass substrate.
Anode material can use transparent high conductivity material, such as indium tin oxygen (ITO), indium zinc oxygen (IZO), titanium dioxide
Tin (SnO2), zinc oxide (ZnO) etc..It is preferable to use ITO to make anode material in device of the present invention.
In device of the invention, for thickness of hole transport layer generally at 5nm-5 μm, hole transmission layer can use N, N '-
Two (3- tolyl)-N, N '-diphenyl-[1,1- xenyl] -4,4 '-diamines (TPD) or N, N '-diphenyl-N, N '-two (1-
Naphthalene) the tri-arylamine groups material such as-(1,1 '-xenyl) -4,4 '-diamines (NPB).Device architecture can also be with for single-shot photosphere
It is multi-luminescent layer structure；Every layer of luminescent layer can be also possible to doped structure for single-shot body of light luminescent material structure；Luminescent dopant
Agent can select phosphor material；Luminescent color is unlimited, can be such as red, yellow, blue, green.
Cathode can use metal and its mixture structure, such as Mg:Ag, Ca:Ag, be also possible to electron injecting layer/gold
Belong to layer structure, such as LiF/Al, Li2The common cathodes structure such as O/Al.Wherein electron injecting layer can for alkali metal, alkaline-earth metal,
Simple substance, compound or the mixture of transition metal are also possible to the composite cathode structure of multilayer material composition.
In general, organic electroluminescence device includes the multilayer organic layer between cathode and anode comprising empty
Cave transport layer, luminescent layer, electron transfer layer and electron injecting layer etc..In cited in lower general remark and embodiment
It is well known by persons skilled in the art to be related to other technology contents of organic electroluminescence device other than appearance, for example, production method and
General ingredient etc., is also applied in the present invention.
Specific embodiment
Referring to following examples set forth the preparation methods of representation compound of the invention.Since the compounds of this invention has
Identical skeleton, those skilled in the art be based on these preparation methods, can by known functional group's conversion method, be readily synthesized
Other the compound of the present invention.Hereinafter, also providing the preparation method and luminosity survey of the luminescent device comprising the compound
It is fixed.
Unless otherwise indicated, raw materials used, intermediate is commercial goods in the present invention；Mass spectrum uses ZAB- in the present invention
HS type mass spectrograph measures (manufacture of MicroMass company, Britain).
Representative synthesis path:
Embodiment 1: the preparation of compound C2
The preparation of compound 1-1
After 2,4- dichloroquinazoline (500g, 2.5mol) is dissolved in 10L ethyl alcohol in flask, in 5 DEG C of dropwise addition water under stirring
It closes hydrazine (470g, 7.5mol, 80% aqueous solution), process is added dropwise, temperature is kept to be lower than 10 DEG C.Nature is added dropwise to be warmed to room temperature instead
Answer 1 hour, filter the solid of precipitation, washed respectively with water and ethyl alcohol, dry to obtain off-white powder compound 1-1 (415g,
86%).
The preparation (bibliography J.Heterocyclic chem.27,497,1990) of compound 1-2
Compound 1-1 (200g, 1.03mol) is added in the flask containing 2L ethyl alcohol, lower dropwise addition benzaldehyde is stirred at room temperature
(120g, 1.13mol) is added dropwise and continues to be stirred to react 30 minutes, filters obtained solid, is drenched respectively with ethyl alcohol and n-hexane
It washes, dry yellow solid compound 1-2 (184g, 63%).
The preparation of compound 1-3
Compound 1-2 (184g, 652.4mmol) is added in the flask containing 4L ethyl alcohol, is stirred at room temperature down and is added portionwise
Iodobenzene acetate (252g, 782.9mmol), finishes, and continues to be stirred to react 1.5 hours, and TLC shows fully reacting.Be added 4L just oneself
Alkane stirs filters the solid of precipitation after five minutes, n-hexane elution, dry light brown yellow solid chemical compound 1-3 (130g,
71%).
The preparation of compound 1-4
By bromo- 9,10- bis- (B- the naphthalene)-anthracene (508g, 1mol) of 2-, pinacol borate (381g, 1.5mol), potassium acetate
(294g, 3mol), which is added, to be contained in Isosorbide-5-Nitrae-dioxane (3L) flask, and Pd (dppf is added after lower displacement nitrogen is stirred at room temperature2)Cl2
(7.32g,0.01mol).It finishes, is stirred at reflux reaction 24 hours, TLC monitors reaction end.Filter the solid being precipitated.Washing,
It is dried to obtain compound 1-4 (500.4g, yield 90%).
The preparation of compound C2
By compound 1-3 (5g, 18mmol), compound 1-4 (10g, 18mmol), potassium carbonate (7.45g, 54mmol) is added
Contain Isosorbide-5-Nitrae-dioxane: in the flask of water (150mL:50mL), Pd (PPh is added after lower displacement nitrogen is stirred at room temperature3)4
(208mg,0.18mmol).It finishes, nitrogen atmosphere stirs lower heating reflux reaction 12 hours, TLC display fully reacting.Filtering is precipitated
Yellow solid.Methylene chloride dissolution, anhydrous sodium sulfate is dry, and column chromatography (eluant, eluent is methylene chloride) obtains yellow solid
It closes object C2 (8.5g, yield 70%).Molecular weight calculated value: 674.25, measured value C/Z:674.2.
Embodiment 2: the preparation of compound C14
The preparation of compound 2-1
Compound 1-1 (20g, 103mmol) is added in the flask containing 200mL ethyl alcohol, lower addition hexichol is stirred at room temperature
And furans -2- formaldehyde (24.5g, 125mmol), finish and continue to be stirred to react 30 minutes, filter obtained solid, respectively with ethyl alcohol and
N-hexane elution, dry yellow solid compound 2-1 (25.6g, 67%).
The preparation of compound 2-2
Compound 2-1 (25.6g, 69mmol) is added in the flask containing 200L ethyl alcohol, is stirred at room temperature down and is added portionwise
Iodobenzene acetate (26.7g, 82.8mmol) finishes and continues to be stirred to react 1.5 hours, and TLC shows fully reacting.200mL is added just
Hexane, stirring filter obtained solid after five minutes, n-hexane elution, dry yellow-brown solid compound 2-2 (17.8g,
70%).
The preparation of compound C14
By compound 2-2 (6.66g, 18mmol), compound 1-4 (10g, 18mmol), potassium carbonate (7.45g, 54mmol)
It is added and contains Isosorbide-5-Nitrae-dioxane: in the flask of water (150mL:50mL), Pd (PPh is added after lower displacement nitrogen is stirred at room temperature3)4
(208mg,0.18mmol).It finishes, nitrogen atmosphere stirs lower heating reflux reaction 12 hours, TLC display fully reacting.Filtering gained
Yellow solid.Methylene chloride dissolution, anhydrous sodium sulfate is dry, and column chromatography (eluant, eluent is methylene chloride) obtains yellow solid chemical combination
Object C14 (10g, yield 73%).Molecular weight calculated value: 764.26, measured value C/Z:764.3.
Embodiment 3: the preparation of compound C26
The preparation of compound 3-1
After the chloro- 7- bromine quinazoline (50g, 0.181mol) of 2,4- bis- is dissolved in 1L ethyl alcohol in flask, dripped under stirring at 5 DEG C
Add hydrazine hydrate (34g, 0.543mol, 80% aqueous solution), process is added dropwise, temperature is kept to be lower than 10 DEG C.Nature is added dropwise and rises to room
Temperature reaction 1 hour, filters obtained solid, washs solid respectively with water and ethyl alcohol, dry to obtain faint yellow solid compound 3-1
(39.4g, 80%).
The preparation of compound 3-2
Compound 3-1 (39.4g, 0.145mol) is added in the flask containing 0.4L ethyl alcohol, lower dropwise addition benzene is stirred at room temperature
Formaldehyde (18.4g, 0.174mol) is added dropwise and continues to be stirred to react 30 minutes, filters obtained solid, uses ethyl alcohol and just oneself respectively
Alkane elution, dry faint yellow solid compound 3-2 (34g, 65%).
The preparation of compound 3-3
Compound 3-2 (34g, 94.3mmol) is added in the flask containing 0.6L ethyl alcohol, is stirred at room temperature down and is added portionwise
Iodobenzene acetate (36.4g, 113.2mmol), finishes, and continues to be stirred to react 1.5 hours, and TLC shows fully reacting.0,6L is added just
Hexane stirring filters obtained solid after five minutes, n-hexane elution, dry faint yellow solid compound 3-3 (23.6g, 70%).
The preparation of compound 3-4
By compound 3-3 (6.44g, 18mmol), compound 1-4 (10g, 18mmol), potassium carbonate (7.45g, 54mmol)
It is added and contains Isosorbide-5-Nitrae-dioxane: in the flask of water (150mL:50mL), Pd (PPh is added after lower displacement nitrogen is stirred at room temperature3)4
(208mg,0.18mmol).It finishes, nitrogen atmosphere stirs lower heating reflux reaction 12 hours, TLC display fully reacting.Filtering gained
Yellow solid.Methylene chloride dissolution, anhydrous sodium sulfate is dry, and column chromatography (eluant, eluent is methylene chloride) obtains yellow solid chemical combination
Object 3-4 (10.2g, yield 75%).
The preparation of compound C26
By phenyl boric acid (1.65g, 13.56mmol), compound 3-4 (10.2g, 13.56mmol), potassium carbonate (5.6g,
It 40.7mmol) is added containing in Isosorbide-5-Nitrae-dioxane/water (150mL/50mL) flask, Pd is added after lower displacement nitrogen is stirred at room temperature
(PPh3)4(157mg,0.136mmol).It finishes, is stirred at reflux reaction 8 hours, TLC monitors reaction end.What filtering was precipitated consolidates
Body.Liquid phase liquid separation, water phase are extracted with dichloromethane, and merge organic phase, and anhydrous sodium sulfate dries, filters, and decompression rotation removes solvent.It closes
And solid crude product, column chromatography for separation purify (eluant, eluent is methylene chloride), obtain compound C26 (7.1g, yield 70%).Molecule
Measure calculated value: 750.28, measured value C/Z:750.3.
Embodiment 4: the preparation of compound C32
The preparation of compound 4-1
Compound 1-1 (20g, 0.103mol) is added in the flask containing 0.4L ethyl alcohol, lower addition is stirred at room temperature to bromine
Benzaldehyde (22.8g, 0.124mol) is added dropwise and continues to be stirred to react 30 minutes, filters obtained solid, respectively with ethyl alcohol and just
Hexane, dry faint yellow solid compound 4-1 (24.1g, 65%).
The preparation of compound 4-2
Compound 4-1 (24.1g, 66.9mmol) is added in the flask containing 0.4L ethyl alcohol, is stirred at room temperature down and adds in batches
Enter iodobenzene acetate (225.9g, 80.3mmol), finish and continue to be stirred to react 1.5 hours, TLC shows fully reacting.0.4L is added
N-hexane stirring filters obtained solid after five minutes, n-hexane elution, dry light brown yellow solid chemical compound 4-2 (16.8g,
70%).
The preparation of compound 4-3
By phenyl boric acid (5.71g, 46.83mmol), compound 4-2 (16.8g, 46.83mmol), potassium carbonate (19.4g,
It 140.5mmol) is added containing in Isosorbide-5-Nitrae-dioxane/water (150mL/50mL) flask, is added after lower displacement nitrogen is stirred at room temperature
Pd(PPh3)4(541mg,0.468mmol).It finishes, is stirred at reflux reaction 8 hours, TLC monitors reaction end.Liquid separation, water phase are used
Methylene chloride extraction, merges organic phase, and anhydrous sodium sulfate dries, filters, and decompression rotation removes solvent.Column chromatography for separation purification (elution
Agent is Shi You Mi ﹕ methylene chloride=5 1~3:1 of ﹕), obtain compound 4-3 (12.5g, yield 67%).
The preparation of compound C32
By compound 4-3 (7.2g, 18mmol), compound 1-4 (10g, 18mmol), potassium carbonate (7.45g, 54mmol) adds
Enter containing Isosorbide-5-Nitrae-dioxane: in the flask of water (150mL:50mL), Pd (PPh is added after lower displacement nitrogen is stirred at room temperature3)4
(208mg,0.18mmol).It finishes, nitrogen atmosphere stirs lower heating reflux reaction 12 hours, TLC display fully reacting.Filtering gained
Yellow solid.Methylene chloride dissolution, anhydrous sodium sulfate is dry, and column chromatography (eluant, eluent is methylene chloride) obtains yellow solid chemical combination
Object C32 (10.8g, yield 80%).Molecular weight calculated value: 750.28, measured value C/Z:750.3.
Embodiment 5: the preparation of compound C43
The preparation of compound 5-1
Will be to chlorophenylboronic acid (8.36g, 53.6mmol), compound 1-3 (15g, 53.6mmol), potassium carbonate (22.2g,
It 160.8mmol) is added containing in Isosorbide-5-Nitrae-dioxane/water (300mL/100mL) flask, Pd is added after lower displacement nitrogen is stirred at room temperature
(PPh3)4(619mg,0.536mmol).It finishes, is stirred at reflux reaction 8 hours, TLC monitors reaction end.Liquid separation, water phase is with two
Chloromethanes extraction, merges organic phase, and anhydrous sodium sulfate dries, filters, and decompression rotation removes solvent.Column chromatography for separation purifies (eluant, eluent
For Shi You Mi ﹕ methylene chloride=5 1~2:1 of ﹕), compound 5-1 (14.1g, yield 74%) is obtained.
The preparation of compound 5-2
By compound 5-1 (14.1g, 39.7mmol), pinacol borate (15.1g, 59.5mmol), potassium phosphate
(25.2g, 119.1mmol) is added containing in Isosorbide-5-Nitrae-dioxane (300mL) flask, and Pd is added after lower displacement nitrogen is stirred at room temperature2
(dba)3(364mg, 0.397mmol), Sphos (488mg, 1.191mmol).It finishes, is stirred at reflux reaction 24 hours, TLC prison
Control reaction end.Liquid separation is washed, water phase is extracted with dichloromethane, and merges organic phase, and anhydrous sodium sulfate dries, filters, decompression rotation
Except solvent.Column chromatography for separation purification (eluant, eluent be Shi You Mi ﹕ methylene chloride=3 ﹕ 1), be dried to obtain compound 5-2 (15.1g,
Yield 85%).
The preparation of compound C43
By the bromo- 10- naphthyl anthracene (7.64g, 20mmol) of 9-, compound 5-2 (8.96g, 20mmol), potassium carbonate (8.3g,
It 60mmol) is added and contains Isosorbide-5-Nitrae-dioxane: in the flask of water (150mL:50mL), Pd is added after lower displacement nitrogen is stirred at room temperature
(PPh3)4(231mg,0.2mmol).It finishes, nitrogen atmosphere stirs lower heating reflux reaction 12 hours, TLC display fully reacting.It crosses
Filter gained yellow solid.Methylene chloride dissolution, anhydrous sodium sulfate is dry, and it is solid that column chromatography (eluant, eluent is methylene chloride) obtains yellow
Body compound C43 (10.2g, yield 82%).Molecular weight calculated value: 624.23, measured value C/Z:624.2.
Embodiment 6: the preparation of compound C53
The preparation of compound 6-1
By compound 4-3 (15g, 37.5mmol), pinacol borate (14.3g, 56.3mmol), potassium acetate (11g,
It 112.5mol) is added and contains in Isosorbide-5-Nitrae-dioxane (300mL) flask, Pd (dppf is added after lower displacement nitrogen is stirred at room temperature2)Cl2
(275mg,0.375mmol).It finishes, is stirred at reflux reaction 24 hours, TLC monitors reaction end.Filter the solid being precipitated.Dichloro
Methane dissolution, anhydrous sodium sulfate is dry, and column chromatographs (eluant, eluent is petroleum ether: methylene chloride=2:1), is dried to obtain compound 6-
1 (14.1g, yield 84%).
The preparation of compound C53
By the bromo- 10- naphthyl anthracene (7.64g, 20mmol) of 9-, compound 6-1 (9g, 20mmol), potassium carbonate (8.3g,
It 60mmol) is added and contains Isosorbide-5-Nitrae-dioxane: in the flask of water (150mL:50mL), Pd is added after lower displacement nitrogen is stirred at room temperature
(PPh3)4(231mg,0.2mmol).It finishes, nitrogen atmosphere stirs lower heating reflux reaction 12 hours, TLC display fully reacting.It crosses
Filter gained yellow solid.Methylene chloride dissolution, anhydrous sodium sulfate is dry, and it is solid that column chromatography (eluant, eluent is methylene chloride) obtains yellow
Body compound C53 (10.7g, yield 86%).Molecular weight calculated value: 624.23, measured value C/Z:624.2.
Embodiment 7: the preparation of compound C63
The preparation of compound 7-1
By phenyl boric acid (3.66g, 30mmol), compound 3-3 (10.7g, 30mmol), potassium carbonate (12.4g, 90mmol) adds
Enter and Pd (PPh is added containing in Isosorbide-5-Nitrae-dioxane/water (150mL/50mL) flask, being stirred at room temperature after lower displacement nitrogen3)4
(347mg,0.3mmol).It finishes, is stirred at reflux reaction 8 hours, TLC monitors reaction end.Liquid separation, water phase are extracted with methylene chloride
It takes, merges organic phase, anhydrous sodium sulfate dries, filters, and decompression rotation removes solvent.(eluant, eluent is Shi You Mi ﹕ for column chromatography for separation purification
Methylene chloride=5 ﹕ 1), obtain compound 7-1 (7.8g, yield 65%).
The preparation of compound 7-2
By compound 7-1 (7.8g, 19.5mmol), pinacol borate (7.44g, 29.3mmol), potassium acetate (5.7g,
It 58.5mol) is added and contains in Isosorbide-5-Nitrae-dioxane (200mL) flask, Pd (dppf is added after lower displacement nitrogen is stirred at room temperature2)Cl2
(143mg,0.195mmol).It finishes, is stirred at reflux reaction 24 hours, TLC monitors reaction end.Wash liquid separation, water phase dichloro
Methane extraction, merges organic phase, and anhydrous sodium sulfate dries, filters, and decompression rotation removes solvent.(eluant, eluent is for column chromatography for separation purification
Shi You Mi ﹕ methylene chloride=3 ﹕ 1), it is dried to obtain compound 7-2 (7.7g, yield 88%).
The preparation of compound C63
By the bromo- 10- naphthyl anthracene (6.57g, 17.2mmol) of 9-, compound 6-1 (7.7g, 17.2mmol), potassium carbonate
(7.1g, 51.6mmol), which is added, contains Isosorbide-5-Nitrae-dioxane: in the flask of water (150mL:50mL), lower displacement nitrogen is stirred at room temperature
Pd (PPh is added afterwards3)4(200mg,0.17mmol).It finishes, heating reflux reaction 12 hours under nitrogen atmosphere stirs, TLC is shown instead
It should be complete.Filtering gained yellow solid.Methylene chloride dissolution, anhydrous sodium sulfate is dry, and column chromatographs (eluant, eluent is methylene chloride)
Obtain yellow solid compound C63 (9.3g, yield 87%).Molecular weight calculated value: 624.23, measured value C/Z:624.2.
Embodiment 8: the preparation of compound C75
The preparation of compound 8-1
By phenyl boric acid (3.66g, 30mmol), 2,7- dibromos phenanthrene (10g, 30mmol), potassium carbonate (12.4g, 90mmol) adds
Enter and Pd (PPh is added containing in Isosorbide-5-Nitrae-dioxane/water (150mL/50mL) flask, being stirred at room temperature after lower displacement nitrogen3)4
(347mg,0.3mmol).It finishes, is stirred at reflux reaction 8 hours, TLC monitors reaction end.Liquid separation, water phase are extracted with methylene chloride
It takes, merges organic phase, anhydrous sodium sulfate dries, filters, and decompression rotation removes solvent.(eluant, eluent is Shi You Mi ﹕ for column chromatography for separation purification
Methylene chloride=10 ﹕ 1), obtain compound 8-1 (8.5g, yield 85%).
The preparation of compound C75
By compound 8-1 (8.5g, 25.5mmol), compound 7-2 (11.4g, 25.5mmol), potassium carbonate (10.5g,
It 76.5mmol) is added and contains Isosorbide-5-Nitrae-dioxane: in the flask of water (150mL:50mL), being added after lower displacement nitrogen is stirred at room temperature
Pd(PPh3)4(300mg,0.26mmol).It finishes, nitrogen atmosphere stirs lower heating reflux reaction 12 hours, TLC display fully reacting.
Filtering gained yellow solid.Methylene chloride dissolution, anhydrous sodium sulfate is dry, and column chromatography (eluant, eluent is methylene chloride) obtains yellow
Solid chemical compound C75 (12.9g, yield 88%).Molecular weight calculated value: 574.22, measured value C/Z:574.2.
Embodiment 9: the preparation of compound C89
The preparation of compound 9-1
By compound 8-1 (9.96g, 30mmol), pinacol borate (11.43g, 45mmol), potassium acetate (8.82g,
It 90mol) is added and contains in Isosorbide-5-Nitrae-dioxane (200mL) flask, Pd (dppf is added after lower displacement nitrogen is stirred at room temperature2)Cl2
(220mg,0.3mmol).It finishes, is stirred at reflux reaction 24 hours, TLC monitors reaction end.Liquid separation, water phase are extracted with methylene chloride
It takes, merges organic phase, anhydrous sodium sulfate dries, filters, and decompression rotation removes solvent.(eluant, eluent is Shi You Mi ﹕ for column chromatography for separation purification
Methylene chloride=5 ﹕ 1), it is dried to obtain compound 9-1 (9.12g, yield 80%).
The preparation of compound C89
By compound 9-1 (9.12g, 24mmol), compound 1-3 (6.72g, 24mmol), potassium carbonate (9.94g,
It 72mmol) is added and contains Isosorbide-5-Nitrae-dioxane: in the flask of water (150mL:50mL), Pd is added after lower displacement nitrogen is stirred at room temperature
(PPh3)4(277mg,0.24mmol).It finishes, nitrogen atmosphere stirs lower heating reflux reaction 12 hours, TLC display fully reacting.It crosses
Filter gained yellow solid.Methylene chloride dissolution, anhydrous sodium sulfate is dry, and it is solid that column chromatography (eluant, eluent is methylene chloride) obtains yellow
Body compound C89 (9.7g, yield 81%).Molecular weight calculated value: 498.18, measured value C/Z:498.2.
Embodiment 10: the preparation of compound C94
The preparation of compound 10-1
By 4- pyridine boronic acid (3.69g, 30mmol), 2,6- dibromo pyrenes (10.74g, 30mmol), potassium carbonate (12.4g,
It 90mmol) is added containing in Isosorbide-5-Nitrae-dioxane/water (150mL/50mL) flask, Pd is added after lower displacement nitrogen is stirred at room temperature
(PPh3)4(347mg,0.3mmol).It finishes, is stirred at reflux reaction 8 hours, TLC monitors reaction end.Liquid separation, water phase dichloro
Methane extraction, merges organic phase, and anhydrous sodium sulfate dries, filters, and decompression rotation removes solvent.(eluant, eluent is for column chromatography for separation purification
Methylene chloride), obtain compound 10-1 (8.57g, yield 80%).
The preparation of compound 10-2
By compound 10-1 (8.57g, 24mmol), pinacol borate (9.14g, 36mmol), potassium acetate (9.94g,
It 72mol) is added and contains in Isosorbide-5-Nitrae-dioxane (200mL) flask, Pd (dppf is added after lower displacement nitrogen is stirred at room temperature2)Cl2
(176mg,0.24mmol).It finishes, is stirred at reflux reaction 24 hours, TLC monitors reaction end.Wash liquid separation, water phase dichloro
Methane extraction, merges organic phase, and anhydrous sodium sulfate dries, filters, and decompression rotation removes solvent.(eluant, eluent is for column chromatography for separation purification
Methylene chloride: methanol=50:1), it is dried to obtain compound 10-2 (6.81g, yield 70%).
The preparation of compound C94
By compound 10-2 (6.81g, 16.8mmol), compound 1-3 (4.7g, 16.8mmol), potassium carbonate (6.96g,
It 50.4mmol) is added and contains Isosorbide-5-Nitrae-dioxane: in the flask of water (150mL:50mL), being added after lower displacement nitrogen is stirred at room temperature
Pd(PPh3)4(196mg,0.17mmol).It finishes, nitrogen atmosphere stirs lower heating reflux reaction 12 hours, TLC display fully reacting.
Filtering gained yellow solid.Methylene chloride dissolution, anhydrous sodium sulfate is dry, column chromatography (eluant, eluent is methylene chloride: methanol=
30:1) obtain yellow solid compound C94 (7.3g, yield 83%).Molecular weight calculated value: 523.18, measured value C/Z:
523.2。
Using mass spectral analysis, compound C1 to C97 is characterized, data are shown in Table 1.
1 synthetic example characterization of compound data of table
Device embodiment
Carry out OLED device evaluation and test using following device architecture: ITO/HAT/HIL/HTL/EML/ETL/LiF/Al is (above-mentioned
Abbreviation respectively correspond ito anode/hole injection layer/hole transmission layer/luminescent layer/electron transfer layer/electron injecting layer/LiF and
The cathode of Al, the meaning of above-mentioned abbreviation is identical below), the following formulae illustrate the structural formulas of the used material of functional layer each in device
(all material is purchased from lark prestige reagent, purity > 99.9%):
Device embodiments 1: use the compounds of this invention as electron transport material
The glass plate for being coated with ITO (150nm) transparency conducting layer is ultrasonically treated in commercial detergent, in deionized water
Middle flushing, in acetone: ultrasonic oil removing in alcohol mixed solvent (volume ratio 1: 1) is baked under clean environment and completely removes water
Part, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned
Vacuum evaporation HAT on anode tunic forms the first hole injection layer with a thickness of 10nm；The vacuum on the first hole injection layer
Vapor deposition 2-TNATA [4,4', 4 "-three (N, N- (2- naphthalene)-phenyl amino) triphenylamines], form the second hole with a thickness of 60nm
Implanted layer；The vacuum evaporation compound N PB on the second hole injection layer forms the hole transmission layer with a thickness of 20nm, vapor deposition
Rate is 0.1nm/s；
Electroluminescence layer, concrete operations are formed on above-mentioned hole transmission layer are as follows: by the Zn as luminous layer main body
(Bzp)2It is placed in the cell of vacuum phase deposition equipment, by (piq) as dopant2[two-(1- phenyl is different by Ir (acac)
Quinolyl) acetylacetone,2,4-pentanedione iridium (III)] it is placed in another room of vacuum phase deposition equipment, it is evaporated simultaneously with different rates
Two kinds of materials, (piq)2The concentration of Ir (acac) is 4%, and vapor deposition total film thickness is 30nm；
Vacuum evaporation the compounds of this invention C2 forms the electron transfer layer that thick film is 20nm, vapor deposition speed on luminescent layer
Rate is 0.1nm/s；
The LiF of vacuum evaporation 0.5nm is as electron injecting layer and with a thickness of the Al layer conduct of 150nm on the electron transport layer
The cathode of device.
The material of the present invention of device embodiments 2. is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound C2 is replaced
It is changed to C14.
The material of the present invention of device embodiments 3. is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound C2 is replaced
It is changed to C26.
The material of the present invention of device embodiments 4. is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound C2 is replaced
It is changed to C32.
The material of the present invention of device embodiments 5. is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound C2 is replaced
It is changed to C43.
The material of the present invention of device embodiments 6. is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound C2 is replaced
It is changed to C53.
The material of the present invention of device embodiments 7. is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound C2 is replaced
It is changed to C63.
The material of the present invention of device embodiments 8. is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound C2 is replaced
It is changed to C75.
The material of the present invention of device embodiments 9. is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound C2 is replaced
It is changed to C89.
The material of the present invention of device embodiments 10. is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound C2 is replaced
It is changed to C94.
Comparative device embodiment 1. uses Bphen as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound C2 is replaced with
Bphen。
Comparative device embodiment 2. uses LG201:QLi as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound C2 is replaced with
The LG201 and QLi of 1:1, the form for taking double source to steam altogether are realized.
Testing example 1
Under same brightness, use 2602 digital sourcemeter luminance meter of Keithley (photoelectric instrument factory, Beijing Normal University)
Measure the driving voltage and electric current of the organic electroluminescence device being prepared in device embodiments 1-10 and comparative example 1 and 2
Efficiency the results are shown in Table 2.
The driving voltage of 2 organic electroluminescence device of table and the measurement result of current efficiency
| Electron transport material | It is required that brightness (cd/m2) | Driving voltage (V) | Current efficiency (cd/A) | |
| Embodiment 1 | C2 | 1000 | 3.6 | 12.9 |
| Embodiment 2 | C14 | 1000 | 3.8 | 12.0 |
| Embodiment 3 | C26 | 1000 | 3.6 | 12.3 |
| Embodiment 4 | C32 | 1000 | 4.0 | 11.8 |
| Embodiment 5 | C43 | 1000 | 3.6 | 12.2 |
| Embodiment 6 | C53 | 1000 | 3.7 | 12.4 |
| Embodiment 7 | C63 | 1000 | 3.5 | 12.1 |
| Embodiment 8 | C75 | 1000 | 3.7 | 11.3 |
| Embodiment 9 | C89 | 1000 | 3.7 | 11.0 |
| Embodiment 10 | C94 | 1000 | 3.6 | 10.7 |
| Comparative example 1 | Bphen | 1000 | 4.5 | 9.0 |
| Comparative example 2 | LG201:QLi | 1000 | 4.1 | 10.5 |
Device embodiments 1-10 and comparative example 1, the identical feelings of other materials in organic electroluminescence device structure
Under condition, series compound of the present invention is instead of Bphen in comparative device embodiment 1 as electron transport material.Seriation of the present invention
Quinazo triazole system of the object due to using more electron deficient is closed, keeps electron injection more efficient, while good electronics
Mobility performance is easier to electron-transport, can more efficiently realize and balance with hole transport, thus can effectively reduce device
Part operating voltage improves current efficiency and improves the luminous efficiency of luminescent device under same device architecture.
Device embodiments 1-10 and comparative example 2, the identical feelings of other materials in organic electroluminescence device structure
Under condition, series compound of the present invention replaces the electron transport material LG201 being commercialized in comparative device embodiment 2 collocation QLi
As electron transport material, voltage is almost the same even lower, and efficiency also has to be promoted by a small margin.But LG201 is needed with to water
More sensitive QLi collocation use is compared, the compounds of this invention can without QLi, effectively realize by electronics from
Cathode is injected into the effect of luminescent layer, to reduce process complexity, while its higher electron mobility also contributes to mentioning
It rises luminous efficiency and reduces operating voltage.The above result shows that new organic materials of the invention are as organic electroluminescence
The electron transport material of part is organic luminescence function material of good performance, is expected to promote commercial applications.
The preferred embodiment of the present invention has been described above in detail, still, during present invention is not limited to the embodiments described above
Detail within the scope of the technical concept of the present invention can be with various simple variants of the technical solution of the present invention are made, this
A little simple variants all belong to the scope of protection of the present invention.
It is further to note that specific technical features described in the above specific embodiments, in not lance
In the case where shield, can be combined in any appropriate way, in order to avoid unnecessary repetition, the present invention to it is various can
No further explanation will be given for the combination of energy.
In addition, various embodiments of the present invention can be combined randomly, as long as it is without prejudice to originally
The thought of invention, it should also be regarded as the disclosure of the present invention.
Obviously, the above embodiments are merely examples for clarifying the description, and does not limit the embodiments.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And it is extended from this it is obvious variation or
It changes still within the protection scope of the invention.
Claims (11)
1. the structure of a kind of compound, compound is indicated by following general formula (I),
Wherein:
L1And L2It is independent to be selected from singly-bound ,-O- ,-S- ,-NRa, the alkylidene of C1-C5, (C1-C3 is sub- by (C1-C3 alkylidene)-O-
Alkyl), the sub- aryl of C6-C30, C3-C30 inferior heteroaryl；
R1It is independent selected from H, substituted or unsubstituted C1~C12 alkyl, C1~C12 alkoxy, halogen, cyano, nitro, hydroxyl,
Silylation, the substituted or unsubstituted aryl of C6~C30, C3~C30 substituted or unsubstituted heteroaryl；R1Quantity be
1,2,3,4, work as R1Quantity be 2 or more when, R1It is same or different；
Ar1And Ar2It is independent to be selected from H, substituted or unsubstituted C1~C12 alkyl, C1~C12 alkoxy, halogen, cyano, nitre
Base, hydroxyl, silylation, the substituted or unsubstituted aryl of C6~C30, C3~C30 substituted or unsubstituted heteroaryl；Its
Middle Ar1And Ar2In at least one be substituted or unsubstituted fused-aryl, 2 or more phenyl ring shapes are contained in the fused-aryl
At fused rings or R1、Ar1And Ar2It is simultaneously phenyl.
2. compound according to claim 1, which is characterized in that Ar1And Ar2In at least one to be substituted or unsubstituted
Fused-aryl, the fused rings that the phenyl ring in the fused-aryl containing 2 or more is formed；And the fused-aryl with thereon
Substituent group either be connected to its L1Or L2Conjugatedπbond is formed, includes at least four phenyl ring in the conjugatedπbond, or
It includes at least three phenyl ring in conjugatedπbond that fused-aryl described in person, which is formed by itself,.
3. compound according to claim 1 or 2, which is characterized in that the Ar1And Ar2At least one of selected from taking
Generation or unsubstituted naphthalene, anthryl, fluoranthene base, fluorenyl, phenanthryl, pyrenyl, triphenylene, base, Qu Ji；The substituent group be 1,
2,3,4 it is independent be selected from H, substituted or unsubstituted C1~C12 alkyl, C1~C12 alkoxy, halogen, cyano, nitro, hydroxyl
Base, silylation, the substituted or unsubstituted aryl of C6~C18, C3~C11 substituted or unsubstituted heteroaryl, it is described to take
It is same or different for base.
4. compound according to claim 1, it is characterised in that Ar1And Ar2At least one of for naphthalene or formula (II) institute
One of group shown, wherein * indicates connection site, formula (II) it is optional by 1,2,3,4 it is independent selected from H, replace or
Unsubstituted C1~C12 alkyl, C1~C12 alkoxy, phenyl, halogen, cyano, nitro, hydroxyl substituent group replaced, it is described
Substituent group is same or different；Wherein Ar3Selected from H, substituted or unsubstituted C1~C12 alkyl, C1~C12 alkoxy, halogen,
Cyano, nitro, hydroxyl, the substituted or unsubstituted aryl of C6~C12, C3~C11 substituted or unsubstituted heteroaryl；When
There are two Ar in formula (II)3When, two Ar3It is same or different；
5. compound according to claim 4, the L1And L2It is independently singly-bound, phenyl, furyl, thienyl, hexichol
And furyl, dibenzothiophene, pyrrole radicals, pyridyl group, xenyl, terphenyl or naphthalene.
6. compound according to claim 4 or 5, the Ar3It is independent selected from H, phenyl, naphthalene, furyl, thienyl,
Pyrrole radicals, pyridyl group, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, indenyl, fluorenyl and its derivative, fluoranthene base, Sanya
Phenyl, pyrenyl, base,Base, aphthacene base, triarylamine, 9,9- dimethyl fluorenyl, diphenylethyllene phenyl, benzo fluorenyl,
Indeno fluorenyl or indenyl.
7. compound according to claim 4 or 5, works as Ar1And Ar2In one of them for shown in naphthalene or formula (II)
When group, another is hydrogen, phenyl, naphthalene, furyl, thienyl, pyrrole radicals, pyridyl group, xenyl, terphenyl, naphthalene
Base, anthryl, phenanthryl, indenyl, fluorenyl and its derivative, fluoranthene base, triphenylene, pyrenyl, base,Base, aphthacene base, three virtues
Amido, 9,9- dimethyl fluorenyl, diphenylethyllene phenyl, benzo fluorenyl, indeno fluorenyl or indenyl.
8. compound according to claim 1, the compound is selected from one of following compound:
9. application of the compound according to any one of claims 1 to 8 in organic electronic device.
10. a kind of organic electroluminescence device, including first electrode, second electrode and the insertion first electrode and second electrode
Between one or more layers organic layer, compound according to any one of claims 1 to 8 is contained in the organic layer.
11. organic electroluminescence device according to claim 10, the organic layer include hole transmission layer, luminescent layer with
And electron transfer layer, the electron transfer layer contain any compound in claim 1~8.
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| PCT/CN2018/112442 WO2019100911A1 (en) | 2017-11-23 | 2018-10-29 | Compound and organic electroluminescent device using same |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019206242A1 (en) * | 2018-04-27 | 2019-10-31 | 北京鼎材科技有限公司 | Organic electroluminescent material and device |
| CN110407838A (en) * | 2018-04-27 | 2019-11-05 | 北京鼎材科技有限公司 | Electroluminescent organic material and device |
| CN111763208A (en) * | 2019-04-02 | 2020-10-13 | 北京鼎材科技有限公司 | Luminescent material and application thereof |
| CN112707908A (en) * | 2019-10-24 | 2021-04-27 | 北京鼎材科技有限公司 | Organic electronic material and application thereof |
| WO2024032784A1 (en) * | 2022-08-12 | 2024-02-15 | 浙江光昊光电科技有限公司 | Organic electroluminescent device and high polymer, composition, mixture, and organic compound for preparing same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101291935A (en) * | 2005-12-13 | 2008-10-22 | Lg化学株式会社 | Novel imidazoquinazoline derivative, process for preparing the same, and organic electronic device using the same |
| CN103221406A (en) * | 2010-09-17 | 2013-07-24 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN104672240A (en) * | 2013-12-26 | 2015-06-03 | 北京鼎材科技有限公司 | Carbazole type derivative and application thereof in organic electroluminescent device |
-
2017
- 2017-11-23 CN CN201711182740.1A patent/CN109824672A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101291935A (en) * | 2005-12-13 | 2008-10-22 | Lg化学株式会社 | Novel imidazoquinazoline derivative, process for preparing the same, and organic electronic device using the same |
| CN103221406A (en) * | 2010-09-17 | 2013-07-24 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN104672240A (en) * | 2013-12-26 | 2015-06-03 | 北京鼎材科技有限公司 | Carbazole type derivative and application thereof in organic electroluminescent device |
Non-Patent Citations (1)
| Title |
|---|
| MAGDY M.GINEINAH,等: "Synthesis and antiinflammatory evaluation of new 2- and 3-substituted 1,2,4-triazolo[4,3-c] and [1,5-c]quinazoline derivatives", 《MED CHEM RES》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019206242A1 (en) * | 2018-04-27 | 2019-10-31 | 北京鼎材科技有限公司 | Organic electroluminescent material and device |
| CN110407838A (en) * | 2018-04-27 | 2019-11-05 | 北京鼎材科技有限公司 | Electroluminescent organic material and device |
| CN111763208A (en) * | 2019-04-02 | 2020-10-13 | 北京鼎材科技有限公司 | Luminescent material and application thereof |
| CN111763208B (en) * | 2019-04-02 | 2023-04-07 | 北京鼎材科技有限公司 | Luminescent material and application thereof |
| CN112707908A (en) * | 2019-10-24 | 2021-04-27 | 北京鼎材科技有限公司 | Organic electronic material and application thereof |
| CN112707908B (en) * | 2019-10-24 | 2024-03-15 | 北京鼎材科技有限公司 | Organic electronic material and application thereof |
| WO2024032784A1 (en) * | 2022-08-12 | 2024-02-15 | 浙江光昊光电科技有限公司 | Organic electroluminescent device and high polymer, composition, mixture, and organic compound for preparing same |
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