CN110526901A - A kind of luminous organic material and its application for preparing organic electroluminescence device - Google Patents

A kind of luminous organic material and its application for preparing organic electroluminescence device Download PDF

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CN110526901A
CN110526901A CN201810515548.8A CN201810515548A CN110526901A CN 110526901 A CN110526901 A CN 110526901A CN 201810515548 A CN201810515548 A CN 201810515548A CN 110526901 A CN110526901 A CN 110526901A
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organic material
luminous
luminous organic
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independent
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邢其锋
黄鑫鑫
邵爽
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Beijing Eternal Material Technology Co Ltd
Guan Eternal Material Technology Co Ltd
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Beijing Eternal Material Technology Co Ltd
Guan Eternal Material Technology Co Ltd
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Abstract

The present invention relates to a kind of novel organic compounds, and in particular to a kind of luminous organic material, and preparation method is further disclosed, and is used to prepare the application of organic electroluminescence device.Luminous organic material of the present invention, the precursor structure of benzo carbazole or azepine benzo carbazole with conjugated polycyclic characteristic, interatomic bond energy is high, has good thermal stability, and be conducive to intermolecular solid-state accumulation, the service life for improving material is used as emitting layer material.

Description

A kind of luminous organic material and its application for preparing organic electroluminescence device
Technical field
The present invention relates to a kind of novel organic compounds, and in particular to a kind of luminous organic material, and it is further disclosed Preparation method, and it is used to prepare the application of organic electroluminescence device.
Background technique
Electroluminescent (electroluminescence, EL) refers to luminescent material under electric field action, by electric current and electricity Excitation and luminous phenomenon, it is a kind of luminescence process that electric energy is converted into luminous energy.Organic electroluminescent Display (hereinafter referred to as OLED) has from main light emission, low-voltage direct-current driving, all solidstate, visual angle are wide, it is light-weight, form and work The a series of advantages such as skill is simple, compared with liquid crystal display, display of organic electroluminescence does not need backlight, and visual angle Greatly, power is low, and for response speed up to 1000 times of liquid crystal display, manufacturing cost is but lower than the liquid crystal of same resolution ratio Show device.Therefore, organic electroluminescence device has very wide application prospect.
As OLED technology is in the continuous propulsion for illuminating and showing two big fields, people are for influencing OLED device performance The research of efficient organic material focuses more on, an excellent in efficiency service life long organic electroluminescence device be usually device architecture with Various organic materials optimization collocation as a result, this functionalization material for just designing and developing various structures for chemists provides Great opportunities and challenges.
Relative to phosphor, electroluminescent organic material has lot of advantages, such as: processing performance is good, can be with It is formed a film on any substrate by the method for vapor deposition or spin coating, Flexible Displays and large-area displays may be implemented；It can pass through The structure for changing molecule, adjusts optical property, electric property and stability of material etc., and the selection of material has very big sky Between.In the most common OLED device structure, the organic material of following type: hole-injecting material, hole transport is generally included Material, electron transport material, and assorted luminescent material (dyestuff or doping guest materials) and corresponding material of main part etc.. The phosphorescent light body material applied at present is all often with single carrier transmittability, such as hole class transmission main body and electricity Subclass transmits main body, and still, single carrier transport ability will cause the mismatch of electrons and holes in luminescent layer, to make At serious efficiency roll-off and the lost of life.
Currently, in the use process of phosphorescent light body material, using the either double material of main part collocation of bipolar materials Form is unbalanced to solve the problems, such as single material of main part carrier.Bipolar materials refer in a compound while realizing electricity The common transport of son and hole, but its molecular structure is complex；Double material of main parts then refer to be used using two kinds of material adapteds To realize the transmission and combination of electrons and holes in luminescent layer, wherein a kind of material is as electron type material, another material It is then used as cavity type material, electrons and holes combine after the conduction of two kinds of materials in interface.Compared to bipolarity material Expect, two kinds of material sources used in double material of main parts are more extensive, and it is real that combination of different materials mode can be taken Now better device performance.
In the prior art, as disclosed in Chinese patent CN103732590A it is a kind of suitable for organic electroluminescence device Benzo carbazole connects the compound of quinolines, but the electric segment of the suction of the compound is the structure of quinolines, and dibenzo-heterocyclic The segment of class is connected with quinolines segment can weaken whole electrophilic performance, lead to the injustice that charge transmits in molecular structure Weighing apparatus property causes the luminous efficiency for showing as material in the devices to reduce；Such material is due to inhaling electrically weaker, LUMO value simultaneously It is shallower, and thus cause electron injection there are barrier, the voltage for showing as device is higher.It is continuous in order to meet OLED device performance The demand of promotion needs to develop the superior organic material of performance, this has very important significance for the development tool of OLED industry.
Summary of the invention
For this purpose, technical problem to be solved by the present invention lies in a kind of luminous organic material is provided, and further provide Above-mentioned luminous organic material is used for the application in ORGANIC ELECTROLUMINESCENCE DISPLAYS field.
In order to solve the above technical problems, a kind of luminous organic material of the present invention, has shown in following general formula (I) Structure:
Wherein,
The X independent of each other is C, CH or N；
The Y independent of each other is C, CH or N；
The m is the integer of 0-6, and the n is the integer of 0-10, and the p is the integer of 0-2；
The L1、L2It is independent of each other to be selected from chemical bond, substituted or unsubstituted C6-C30It is arlydene, substituted or unsubstituted C3-C20Nitrogenous inferior heteroaryl, and the inferior heteroaryl preferably containing 1-2 N；
The Ar1、Ar2It is same or different, it is independent of each other to be selected from substituted or unsubstituted C6-C30Aryl or C3-C30 Heteroaryl；The adjacent Ar1、Ar2Between independently of one another, or be connected to each other cyclization by chemical bond；
The R and R1It is same or different, it is selected from H, C independently of one another1-C6Alkyl, substituted or unsubstituted C6-C30Aryl, Substituted or unsubstituted C3-C20Nitrogenous heteroaryl；
As m >=2, cyclization is condensed between the adjacent R group each other；And/or
When n >=2, the adjacent R1Cyclization is condensed between group each other；
The L1、L2、Ar1、Ar2、R、R1The substituent group of selected group is independent of each other to be selected from C1-C6Alkyl or C6-C30 One of aryl.
Preferably, in structure shown in the general formula (I), the number that the X in mother nucleus structure is N is 0-3, female The number that the Y in nuclear structure is N is 0-3.
The L1、L2It is independent of each other to be selected from singly-bound, phenylene, naphthylene, sub-pyridyl group, sub- quinolyl, sub- quinazolyl Or one of sub- isoquinolyl.
Further, the adjacent Ar1、Ar2Between be connected to each other cyclization by chemical bond, the L1And L2For chemical bond.
The Ar1And Ar2It is independent of each other be selected from substituted or unsubstituted following group: phenyl, xenyl, terphenyl, Naphthalene, fluorenyl, pyridyl group, pyrimidine radicals, quinolyl, isoquinolyl, dibenzofuran group, dibenzothiophene, carbazyl.
The R and R1It is independent of each other to be selected from hydrogen or substituted or unsubstituted following group: phenyl, xenyl, three Phenyl, naphthalene, triphenylene, pyridyl group, pyrimidine radicals, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, naphthyridines base, three Piperazine base, phenanthryl, 9,9- dimethyl fluorenyl, Spirofluorene-based group；
Also, as m >=2, cyclization is condensed between the adjacent R group each other, i.e., to form corresponding knot to its female ring The fused ring aryl or fused ring heteroaryl of structure；And/or
As n >=2, the adjacent R1Cyclization is condensed between group each other, i.e., to form corresponding construction with its female ring Fused ring aryl or fused ring heteroaryl；
The fused ring aryl or fused ring heteroaryl preferably include naphthalene, fluorenyl, quinolyl, isoquinolyl, quinazolyl, One of quinoxalinyl, cinnoline base, naphthyridines base, triazine radical, phenanthryl, 9,9- dimethyl fluorenyl, Spirofluorene-based.
Preferably, the L1、L2、Ar1、Ar2、R、R1The substituent group of selected group is independent of each other to be selected from C1-C4Alkyl Or phenyl.
More preferably, the luminous organic material is selected from structure shown in following A1-A40:
The invention also discloses the applications that the luminous organic material is used to prepare organic electroluminescence device.
The luminous organic material is used as light emitting host material.
The invention also discloses a kind of organic electroluminescence devices, including substrate, and sequentially form on the substrate Anode layer, organic layer and cathode layer；
The organic layer includes organic luminous layer, and the material of main part of the organic luminous layer includes at least one described having Machine luminescent material.
Further, the organic luminescence function layer further include hole injection layer, hole transmission layer, electron transfer layer and Electron injecting layer.
Luminous organic material of the present invention, the mother of benzo carbazole or azepine benzo carbazole with conjugated polycyclic characteristic Body structure, interatomic bond energy is high, has good thermal stability, and is conducive to intermolecular solid-state accumulation, is used as luminescent layer The service life of materials'use raising material.
Benzo carbazole derivative of the present invention is connected with arylamine class segment on benzo carbazole mother nucleus structure, described Derivative can significantly improve compound for the injection in hole and the ability of transmission, effectively improve hole mobility；And work as benzene And the mother nucleus structure of carbazole, with when inhaling electric segment and being connected, gained compound can be used as ambipolar compound as luminescent layer Material of main part is conducive to the balance of charge, realizes very high luminous efficiency；When the mother nucleus structure and aromatic rings segment of benzo carbazole When being connected, the material that the compound can be used as cavity type makes in double main body luminescent materials with the collocation of electron type material of main part With, due to itself very high hole mobility, also can be realized very high luminous efficiency, have superior performance.Meanwhile this Inventing the compound, preparation is simple, and raw material is easy to get, and is suitable for volume production amplification.
Specific embodiment
Synthetic example
The synthesis path of benzo carbazole derivative of the present invention is as follows:
Based on above-mentioned synthesis equation, the different benzo carbazole derivative of the present invention is in the synthesis process, it is only necessary to It is different by replacing according to the structure feature of target productDifferent targets can be obtained by carrying out synthesis Compound.It is but and unlimited and it should be noted that use buchwald hartwig coupling reaction in above-mentioned synthetic method In the coupling method, other suitable methods in the prior art can also be chosen according to the structure of target product.Following synthesis Embodiment carries out the elaboration of phase synthesis process using partial target compound as representative.
The synthesis of 1 compound A1 of synthetic example
In reaction flask, the bromo- benzo carbazole 29.5g (100mmol) of 7-, diphenylamines 18.4g (110mmol), Pd is added2 (dba)30.9g (0.785mmol, 0.5%), toluene 1500ml, potassium carbonate 43.3g (314mmol), 100 DEG C of reaction 3.5h.Instead Stopping reaction after answering, and reactant is cooled to room temperature, filters, obtained solid passes through recrystallization purifying in toluene, Obtain white powder M1.
In reaction flask, 21.8g (100mmol) above-mentioned product M1 is added, and the chloro- 4- phenylquinazoline 16.5g of 2- is added (110mmol) and DMF 500ml, potassium carbonate 43.3g (314mmol), in 140 DEG C of reaction 5h.Stop reaction after completion of the reaction, and Reactant is cooled to room temperature, is filtered, obtained solid obtains white powder A1 by recrystallization purifying in toluene.
1H NMR (CDCl3,400MHz) 8.54 (s, 1H), 8.11 (d, J=10.0Hz, 3H), 7.99 (d, J=6.4Hz, 1H), 7.80 (d, J=8.0Hz, 3H), 7.63 (d, J=12.0Hz, 2H), 7.57-7.37 (m, 9H), 7.36 (d, J=8.0Hz, 2H),7.24(m,3H),7.08(m,2H),7.00(s,2H)。
The synthesis of 2 compound A15 of synthetic example
In reaction flask, 4- phenyl naphthalene boronic acids 24.8g (100mmol), the bromo- nitrobenzene 22g (110mmol) of 2-, four is added (triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500ml, ethyl alcohol 1000ml, potassium carbonate 43.3g (314mmol)/ Water 1000ml, 80 DEG C of reaction 3.5h.Stop reaction after completion of the reaction, and reactant is cooled to room temperature, filters, it is obtained solid Body obtains white powder M1 by recrystallization purifying in toluene.
In N2Protection, be added 35g (100mmol) above-mentioned product M1, and be added 17.7g triphenylphosphine (100mmol), 1000ml o-dichlorohenzene, is heated to reflux, and reacts 12h, solvent is evaporated off after completion of the reaction, silica gel column chromatography obtains M2 intermediate.
The above-mentioned intermediate M2 of 31.8g (100mmol) is taken, and 200mlDMF is added, is added dropwise to bromine (100mmol), room temperature About for 24 hours, water is added in reaction solution for reaction, filters, and washing obtains intermediate M3.
In reaction flask, 37.1g (100mmol) above-mentioned product M3 and diphenylamines 18.4g (110mmol), Pd is added2 (dba)30.9g (0.785mmol, 0.5%), toluene 1500ml, potassium carbonate 43.3g (314mmol), 100 DEG C of reaction 3.5h.Instead Stop reaction after answering, reactant is cooled to room temperature, filter, obtained solid is obtained by recrystallization purifying in toluene To white powder M4.
In reaction flask, 50g (100mmol) above-mentioned product M4 and 3- (3- chlorphenyl)-pyridine 20.8g is added (110mmol)、Pd2(dba)30.9g (0.785mmol, 0.5%), toluene 1500ml, potassium carbonate 43.3g (314mmol), 100 DEG C reaction 3.5h, stops reaction, reactant is cooled to room temperature, and filters, and obtained solid passes through weight in toluene after completion of the reaction Crystallization purifying obtains white powder A15.
1H NMR (CDCl3,400MHz) 9.24 (s, 1H), 8.97 (s, 2H), 8.70 (s, 1H), 8.27 (d, J=8.0Hz, 1H), 8.00 (s, 1H), 7.93 (s, 1H), 7.86 (d, J=12.0Hz, 3H), 7.99-7.68 (m, 4H), 7.79 (s, 2H), 7.99-7.51 (m, 8H), 7.49-7.25 (m, 4H), 7.24 (s, 1H), 7.10 (d, J=12.0Hz, 2H), 7.00 (s, 1H).
Other of the invention optional compounds can the raw material of -2 thinking selection suitable construction in accordance with the above-mentioned embodiment 1 carry out The synthesis of approximation, details are not described herein again.
Device embodiments
The Organic Light Emitting Diode selected in device embodiments of the present invention includes the first electrode and second on substrate Electrode, and the organic layer between electrode, the organic layer can be multilayered structure.For example, the organic material layer can be with Including hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer.
The substrate is using conventional base plate used in organic light emitting display in the prior art, for example, glass, polymeric material Material and the glass with TFT component and polymer material etc..
The anode material can be indium tin oxygen (ITO) well known in the prior art, indium zinc oxygen (IZO), stannic oxide (SnO2), the transparent conductive materials such as zinc oxide (ZnO), be also possible to the metal materials such as silver and its alloy, aluminium and its alloy, can also To be the multilayered structure of the organic conductive materials such as PEDOT and above-mentioned material.
The cathode material can be selected from but not limited to metals, metal mixture, the oxygen such as magnesium silver mixture, LiF/Al, ITO The materials such as compound and structure.
It can also include hole injection layer, the hole transmission layer between luminescent layer and anode in the OLED device, These layers can be, but not limited to one or more combinations of following enumerated HT1-HT31.
Device luminescent layer may include material of main part and luminescent dye, wherein material of main part is including but not limited to as follows One or more combinations of conventional material shown in GPH1-GPH80.
The luminescent dye can be selected but be not limited to one or more combinations of following enumerated GPD1-GPD57.
The electron transport layer materials include but is not limited to one or more combinations of the following ET1-ET57 enumerated.
It can also include the electron injecting layer between electron transfer layer and cathode, electron injecting layer material in the device Material includes but is not limited to LiQ, LiF, NaCl, CsF, Li in the prior art2O、Cs2CO3, it is a kind of in the materials such as BaO, Na, Li, Ca Or several combination.
Organic electroluminescence device preparation process is as follows in device embodiments of the present invention:
The glass plate for being coated with transparent conductive layer is ultrasonically treated in commercial detergent, is rinsed in deionized water, In acetone-ethanol in the mixed solvent ultrasound oil removing, it is baked under clean environment and completely removes moisture content, it is clear with ultraviolet light and ozone It washes, 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 HT-11 is as hole injection layer on anode tunic, and evaporation rate 0.1nm/s, vapor deposition film thickness is 10nm；
Hole transmission layer of the vacuum evaporation HT-5 as device on hole injection layer, evaporation rate 0.1nm/s steam Plating total film thickness is 80nm；
The luminescent layer of vacuum evaporation device on hole transmission layer, luminescent layer include material of main part and dye materials, benefit The method steamed altogether with multi-source is selected as the obtained material of main part of the present invention provided in the following table 1 is deposited or the present invention is made Material of main part steams altogether with GPH16, and the evaporation rate for adjusting material of main part is 0.1nm/s, 3% ratio of dyestuff GPD-1 evaporation rate Setting, vapor deposition total film thickness are 30nm；And device is made as control using material of main part R-1 in the prior art；
The electron transfer layer of vacuum evaporation device on luminescent layer, the selection of material ET42, evaporation rate 0.1nm/ S, vapor deposition total film thickness are 30nm；
On electron transfer layer (ETL) vacuum evaporation with a thickness of the LiF of 0.5nm as electron injecting layer, with a thickness of 150nm Cathode of the Al layer as device.
Following performance measurement is carried out to the organic electroluminescence device prepared by the above process:
Under same brightness, the Organic Electricity that embodiment and comparative example are prepared is measured using digital sourcemeter and luminance meter The driving voltage and current efficiency of electroluminescence device and the service life of device.Specifically, promoting electricity with the rate of 0.1V per second Pressure, measurement reach 10000cd/m when the brightness of organic electroluminescence device2When voltage, that is, driving voltage, while measuring at this time Current density；The ratio of brightness and current density is current efficiency；The life test of LT95 is as follows: being existed using luminance meter 10000cd/m2Under brightness, the electric current kept constant, the brightness for measuring organic electroluminescence device is reduced to 9500cd/m2Time, Unit is hour.
Organic electroluminescence device performance, which is made, with material of main part of the present invention and prior art material of main part see the table below 1 It is shown.
1 organic electroluminescence device results of property of table
Luminescent layer material of main part It is required that brightness cd/m2 Voltage V Current efficiency cd/A Service life (LT95) h
R-1 10000.00 5.7 50.5 38
A1 10000.00 5.2 58.6 45
A3 10000.00 5.1 57.8 48
A12 10000.00 5.3 60.1 46
A15 10000.00 5.3 61.5 47
A21 10000.00 5.4 60.9 49
A24 10000.00 5.4 62.4 45
A29 10000.00 5.1 59.6 50
A32 10000.00 5.0 61.3 47
GPH-16:A15 10000.00 5.4 68.5 53
GPH-16:A21 10000.00 5.5 71.1 56
GPH-16:A24 10000.00 5.4 70.2 52
It, can be effective from upper table data it is found that new organic materials produced by the present invention are used for organic electroluminescence device Reduction landing voltage, improve current efficiency, extend device lifetime, be material of main part of good performance, especially with the present invention Double material of main part devices that the material of main part is mixed with prior art material of main part, device performance are further promoted, especially It is that current efficiency is more excellent.
Device performance of the present invention compares with comparative example device, and device made of material of the present invention is in voltage, efficiency and longevity Life aspect has promotion and improvement.This is primarily due to, in comparative example device in selected material of main part structure, dibenzo-heterocyclic class Segment be connected with quinolines segment and can weaken whole electrophilic performance, lead to the imbalance that charge transmits in molecular structure Property, cause the luminous efficiency for showing as material in the devices to reduce；Simultaneously such material due to inhale electrically it is weaker, LUMO value compared with Shallowly, and thus cause electron injection there are barrier, the voltage for showing as device is higher；And the lack of uniformity of charge transmission can be led Cause the device lifetime of material partially short.
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 (10)

1. a kind of luminous organic material, which is characterized in that have structure shown in following general formula (I):
Wherein,
The X independent of each other is C, CH or N；
The Y independent of each other is C, CH or N；
The m is the integer of 0-6, and the n is the integer of 0-10, and the p is the integer of 0-2；
The L1、L2It is same or different, it is independent of each other to be selected from chemical bond, substituted or unsubstituted C6-C30Arlydene, substitution Or unsubstituted C3-C20Nitrogenous inferior heteroaryl；
The Ar1、Ar2It is same or different, it is selected from substituted or unsubstituted C6-C30Aryl or C3-C30Heteroaryl；It is adjacent The Ar1、Ar2Between independently of one another, or be connected to each other cyclization by chemical bond；
The R and R1It is same or different, it is selected from H, C independently of one another1-C6Alkyl, C substituted or unsubstituted6-C30Aryl, substitution or Unsubstituted C3-C20Nitrogenous heteroaryl；
As m >=2, cyclization is condensed between the adjacent R group each other；And/or
When n >=2, the adjacent R1Cyclization is condensed between group each other；
The L1、L2、Ar1、Ar2、R、R1The substituent group of selected group is independent of each other to be selected from C1-C6Alkyl or C6-C30Virtue One of base.
2. luminous organic material according to claim 1, which is characterized in that female in structure shown in the general formula (I) The number that the X in nuclear structure is N is 0-3, and the number that the Y in mother nucleus structure is N is 0-3.
3. luminous organic material according to claim 1, which is characterized in that the L1、L2It is independent of each other selected from singly-bound, One of phenylene, naphthylene, sub-pyridyl group, sub- quinolyl, sub- quinazolyl or sub- isoquinolyl.
4. luminous organic material according to claim 1, which is characterized in that the adjacent Ar1、Ar2Between pass through chemical bond Be connected to each other cyclization, the L1And L2For chemical bond.
5. luminous organic material according to claim 4, which is characterized in that the Ar1And Ar2Independent of each other be selected from takes Generation or unsubstituted following group: phenyl, xenyl, terphenyl, naphthalene, fluorenyl, pyridyl group, pyrimidine radicals, quinolyl, isoquinoline Quinoline base, dibenzofuran group, dibenzothiophene, carbazyl.
6. luminous organic material according to claim 1, which is characterized in that the R and R1It is independent of each other selected from hydrogen or The substituted or unsubstituted following group of person: phenyl, xenyl, terphenyl, naphthalene, triphenylene, pyridyl group, pyrimidine radicals, quinoline It is quinoline base, isoquinolyl, quinazolyl, quinoxalinyl, naphthyridines base, triazine radical, phenanthryl, 9,9- dimethyl fluorenyl, Spirofluorene-based.
7. luminous organic material according to claim 1-6, which is characterized in that the luminous organic material is selected from Structure shown in following A1-A40:
8. application of any luminous organic material of claim 1-8 in organic electroluminescence device.
9. application according to claim 9, which is characterized in that the luminous organic material is used as light emitting host material.
10. a kind of organic electroluminescence device, including substrate, and sequentially form anode layer, organic layer on the substrate And cathode layer；It is characterized by:
The organic layer includes organic luminous layer, and the material of main part of the organic luminous layer includes at least one claim 1-7 Any luminous organic material.
CN201810515548.8A 2018-05-25 2018-05-25 A kind of luminous organic material and its application for preparing organic electroluminescence device Pending CN110526901A (en)

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