CN104513661B - A kind of luminous organic material and its application - Google Patents
A kind of luminous organic material and its application Download PDFInfo
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- CN104513661B CN104513661B CN201310460233.5A CN201310460233A CN104513661B CN 104513661 B CN104513661 B CN 104513661B CN 201310460233 A CN201310460233 A CN 201310460233A CN 104513661 B CN104513661 B CN 104513661B
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- 239000011368 organic material Substances 0.000 title abstract description 13
- 239000000463 material Substances 0.000 claims abstract description 89
- 238000005401 electroluminescence Methods 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 239000010410 layer Substances 0.000 claims description 63
- 230000005540 biological transmission Effects 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 12
- 238000004020 luminiscence type Methods 0.000 claims description 6
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 6
- 239000002346 layers by function Substances 0.000 claims 1
- 125000005259 triarylamine group Chemical group 0.000 abstract description 10
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract description 3
- 125000005842 heteroatom Chemical group 0.000 abstract description 3
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- 125000001931 aliphatic group Chemical group 0.000 abstract description 2
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- 125000003118 aryl group Chemical group 0.000 abstract description 2
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- 238000006243 chemical reaction Methods 0.000 description 27
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- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- XANHMTXPZQQSMK-UHFFFAOYSA-N Brc(cc1)cc2c1[nH]c1c2c(cccc2)c2c2c1c1ccccc1cc2 Chemical compound Brc(cc1)cc2c1[nH]c1c2c(cccc2)c2c2c1c1ccccc1cc2 XANHMTXPZQQSMK-UHFFFAOYSA-N 0.000 description 1
- JWVPJYBTYWMTGV-UHFFFAOYSA-N Cc(cc1)ccc1-[n](c(CC1)c2C=C1C=[BrH])c1c2c(cccc2)c2c2c1c1ccccc1cc2 Chemical compound Cc(cc1)ccc1-[n](c(CC1)c2C=C1C=[BrH])c1c2c(cccc2)c2c2c1c1ccccc1cc2 JWVPJYBTYWMTGV-UHFFFAOYSA-N 0.000 description 1
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- 150000004982 aromatic amines Chemical class 0.000 description 1
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Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to one kind such as formulas（I）A kind of shown luminous organic material, wherein：Ar1‑Ar9It is independently selected from the substituted or unsubstituted aromatic hydrocarbon group of H, C6 C30, the substituted or unsubstituted condensed-nuclei aromatics groups of C6 C30, the substituted or unsubstituted condensed hetero ring groups of C6 C30, or five yuan, hexa-atomic heterocycle or substituted heterocycle, the substituted or unsubstituted triaryl amine groups of C6 C30, or aryl oxide group, one kind in the substituted or unsubstituted aliphatic alkyl groups of C1 C12, Ar1‑Ar8It is asynchronously H.The present invention also protects application of such compound in organic electroluminescence device, especially as hole-injecting material, hole transport layer material, fluorescent host material or the luminescent material in OLED device.
Description
Technical field
The present invention relates to a kind of novel organic luminescent material more particularly to a kind of chemical combination for organic electroluminescence device
Object and the application in organic electroluminescence device.
Background technology
Display of organic electroluminescence（Hereinafter referred to as OLED）With from main light emission, low-voltage direct-current driving, all solidstate, regard
Angular width, light-weight, composition and a series of advantage such as simple for process, compared with liquid crystal display, display of organic electroluminescence
Backlight is not needed to, visual angle is big, and power is low, and up to 1000 times of liquid crystal display, manufacture cost is but less than response speed
The liquid crystal display of equal resolution ratio, therefore, organic electroluminescence device has broad application prospects.
What the generation of organic electroluminescent was leaned on is the carrier transmitted in organic electroluminescence material（Electrons and holes）Weight
Group, it is well known that the electric conductivity of organic material is very poor, does not have what is continued unlike inorganic semiconductor, in organic semiconductor
Energy band, the transmission of carrier commonly uses jump theory to describe, i.e., under the driving of an electric field, electronics is being excited or is being injected into point
In the lumo energy of son, achieve the purpose that charge transmits via the lumo energy for jumping to another molecule.In order to make have
Organic electroluminescence devices reach breakthrough in application aspect, it is necessary to overcome the difficulty of the injection of organic material charge and transmittability difference.
Scientists are by the adjustment of device architecture, such as increase the number of device organic material layer, and play the part of different organic layers
Different roles is drilled, such as the functional material having helps electronics to be injected from cathode and hole from anode, some materials help electricity
The transmission of lotus, the material played the role of then plays blocking electronics and hole transport, most important certainly in organic electroluminescent
The luminescent material of a variety of colors will also achieve the purpose that match with adjacent functional material, the Organic Electricity of an excellent in efficiency long lifespan
Electroluminescence device is typically the optimization collocation as a result, this is just designed out for chemists of device architecture and various organic materials
The functionalization material for sending out structure various provides great opportunities and challenges.
The hole injection used always in organic electroluminescent device and transmission material are usually derivative of tri-arylamine group（Example
Such as light extraction patent：Publication number CN1152607C, publication date 2004,6,2）, it is general to be structurally characterized in that, as injection material,
Its triaryl amine structural unit is at least at three or more in a molecule, and is separated between two N with a phenyl ring, sees formula 1；Make
For transmission material, its triaryl amine structural unit is usually two in a molecule, and is separated between two N with biphenyl, at this
In class material, typical example is NPB, and structure is shown in formula 2.
In recent years, the research of this kind of material has some new progresses, introduce in the molecule one or more thienyls or
Person introduces one or more benzothienyls, sees formula 3 and formula 4（Light extraction patent：Publication number CN101506191A, publication date 2009,
8,12）, the result is that considerably increasing the Hole injection capacity of material；As transmission material, when by a triaryl amine in material
When structural unit carbazole or dibenzofurans replace, the transmittability of material all has a more substantial increase.See formula 5 and formula 6（Go out
Light patent：Publication number CN102334210A, the applying date 2012,1,25；Publication number：WO 2010/114017A1, publication date 2010,
10,7）.
Invention content
The purpose of the present invention is to provide a kind of novel organic luminescent material, such luminous organic material can be used for organic
Electroluminance display field.
For this purpose, the technical solution that the present invention takes is：
A kind of luminous organic material has such as formula（I）Shown structure：
Wherein：
Ar1-A9It is independently selected from H, the substituted or unsubstituted aromatic hydrocarbon groups of C6-C30, the substituted or unsubstituted condensed ring of C6-C30
Aromatic hydrocarbon group, the substituted or unsubstituted condensed hetero ring groups of C6-C30 or five yuan, hexa-atomic heterocycle or substituted heterocycle, C6-C30 take
Generation or unsubstituted triaryl amine group or aryl oxide group, one kind in the substituted or unsubstituted aliphatic alkyl groups of C1-C12,
It is H during Ar1-Ar8 differences.
Further, described Ar5, Ar6, Ar7, Ar8, Ar9 are simultaneously H.
Further, the Ar4 is selected from phenyl, substituted-phenyl, xenyl, naphthalene, anthryl, phenanthryl, base, pyrenyl.
Further, described Ar1, Ar2, Ar3 separately selected from phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, Qu Ji,
Base, substitution anthryl, carbazyl, triphenylene, substitution click are bent in benzo phenanthryl, substituted-phenyl, substituted naphthyl, substitution pyrenyl, substitution
Oxazolyl, dibenzothiophene, substituted diphenylamine bithiophene base, dibenzofuran group, substituted diphenylamine and furyl, take triarylamine
For triarylamine.
In order to become apparent from illustrating the content of present invention, lower mask body narration the present invention relates to compound preferred structure：
The present invention provides a kind of luminous organic material, applied in organic electroluminescence device.
Further, the luminous organic material can be used as hole-injecting material, hole in organic electroluminescence device
Transmission material or material of main part.
The present invention also provides a kind of organic electroluminescence devices, including substrate and sequentially form on the substrate
Anode layer, organic luminescence function layer and cathode layer；
The organic luminescence function layer includes hole transmission layer, organic luminous layer and electron transfer layer；
The host material of the hole transmission layer contains the luminous organic material.
The present invention also provides a kind of organic electroluminescence devices, including substrate and sequentially form on the substrate
Anode layer, organic luminescence function layer and cathode layer；
The organic luminescence function layer includes hole transmission layer, organic luminous layer and electron transfer layer；
The host material of the organic luminous layer contains the luminous organic material.
For the convenience of description, hole mobile material signified in the application subsequent content is the matrix material of hole transmission layer
Material, material of main part is the host material of organic luminous layer.
Compared with prior art, the invention has the advantages that：
In the present invention, we have proposed a kind of new materials, are in parent nucleusUpper key connects one that a carbazole is general formula
Series compound, this new material be not only suitable as material of main part but also had made hole mobile material, when connecting condensed-nuclei aromatics on parent nucleus,
Such material is suitable as light emitting host material, applies on device, can improve a lot to luminous efficiency, device lifetime
It is longer.When being connected with triaryl amine or condensed hetero ring aromatic hydrocarbons on parent nucleus, for example, carbazole group, dibenzothiophenes group, dibenzo furan
It mutters group etc., such material is suitable as hole mobile material.This new material is used as hole transport material in red device
Material application is preferable, and the use of material of the present invention reduces the luminous efficiency for opening bright voltage, improving device of device, increases
The service life of device.
（2）Preparation is simple for the compounds of this invention, and these compounds have good thermal stability, high
Hole mobility, the electroluminescent device made of the material, the bright voltage that opens of device substantially reduce, and luminous efficiency is carried
Height, while the service life of device dramatically increases, and hole mobile material or organic can be used as in organic electroluminescence device
The material of main part of luminescent layer.
Description of the drawings
In order to be more easily understood present disclosure, Gaussian03B3LYP/6-31G is used in the present invention（d）Method
The highest occupied molecular orbital(HOMO) of compound is acquired respectively（HOMO）, lowest unoccupied molecular orbital（LUMO）And triplet（T1）.
Fig. 1 is the highest occupied molecular orbital(HOMO) of compound 9 in the embodiment of the present invention 10, and HOMO energy levels are -5.040ev, three
Line state energy level T1=1.7362ev；
Fig. 2 is the lowest unoccupied molecular orbital of compound 9 in the embodiment of the present invention 10, and lumo energy is -1.542ev.
Specific embodiment
Basic raw material used in the present invention, 6- bromines2,4- bis- bromo nitrobenzenes, 2,5- bis- bromo nitrobenzenes and bromine
For carbazole derivates, bromo dibenzofurans, bromo dibenzothiophenes, bromoDerivative, bromo triphenylene, bromo pyrene, bromine
It for anthracene derivant etc., major industrial chemicals can be commercially available at home, above-mentioned each bromo condensed-nuclei aromatics can use common lab side
Method synthesizes its boronic acid derivatives.
Embodiment 1
Preparation embodiment for intermediate of the present invention：
Main intermediateThe synthesis of -6- boric acid
By the 6- bromines of 6.12g（Molecular weight 306,0.02mol）It is dissolved in the THF of 100ml dryings, -80 DEG C are added dropwise positive fourth
Basis mechanism 10ml（2.5M, 0.025mol）, 15min is stirred, then triisopropyl borate 16ml is added dropwise.Hydrolysis adjusts pH to neutrality
White boronic acid derivatives 5.5g, yield intimate 100% is precipitated.
Embodiment 2
The synthesis of compound 1,
（1）The first step
1000 milliliters of a bite bottles with magnetic agitation, add in- 6- boric acid 5.5g（Molecular weight 272,0.02mol）, 2,4- bis-
Bromo nitrobenzene 5.84g（Molecular weight 278,0.021mol）, 4 usage amount 1.5g of Pd (PPh3)（Molecular weight 1154,0.0013mol）,
Sodium carbonate 150ml（2M）, toluene 150ml, ethyl alcohol 150ml.After argon gas displacement, reflux is monitored with TLC and reacted, reacted after 3 hours
Completely, cool down, separated base, be evaporated, carried out post separation with 1/10 ethyl acetate/petroleum ether, obtain, 7.82g products, point
Son amount 427, yield 91.5%.
（2）Second step
50 milliliters of a bite bottles with magnetic agitation, add in the final product 7.82g of the first step（Molecular weight 427,
0.0183mol）, triphenylphosphine 5.76g（Molecular weight 262,0.022mol）, o-dichlorohenzene 150ml.Mixture is heated to 175 DEG C,
Stirring with TCL board monitoring reaction process, is reacted 15 hours and is completed.Cooling, is evaporated in vacuo solvent, washes, dry, uses column chromatography
Separation, ethyl acetate and petroleum ether mixtures elution, obtain target molecule 6.5g, molecular weight 395, yield 89.6%.
（3）Third walks
500 milliliters of a bite bottles with magnetic agitation, add in second step final product 6.5g（Molecular weight 395,0.0164mol）,
To methiodide benzene 5.45g（Molecular weight 218,0.025mol）, cuprous iodide 1.0g（Molecular weight 190,0.00526mol）, potassium carbonate
8.3g（138,0.06mol）, DMPU solvents 100ml.Mixture is heated to 175 DEG C, stirring, with TCL board monitoring reaction process, instead
It answers 13 hours and completes.Cooling, is poured into water, filters out, dry, with pillar layer separation, ethyl acetate and petroleum ether mixtures elution,
Obtain target molecule 6.88g, molecular weight 487, yield 86.1%.
（4）4th step
1000 milliliters of a bite bottles with magnetic agitation, add in above-mentioned third step final product 6.88g（Molecular weight 487,
0.0141mol）, triphenylamine -4- boric acid 4.74g（Molecular weight 289,0.0164mol）, 4 usage amount 1.50g of Pd (PPh3)（Molecule
Amount 1154,0.0013mol）, aqueous sodium carbonate 130ml（2M）, toluene 130ml, ethyl alcohol 130ml.After argon gas displacement, reflux,
It is monitored and reacted with TLC, the reaction was complete after 4 hours, and cooling, product solid is largely precipitated, and filtering is purified with recrystallization method
（Post separation Methods For Purification can be also used when necessary）, obtain 6.73g products, molecular weight 636, yield 75%.
Embodiment 3
The synthesis of compound 2
Synthesis step is same as the four-step reaction in embodiment 2, only iodobenzene will be changed into methiodide benzene in third step, the
Triphenylamine -4- boric acid is changed into 4- by four steps（N- phenyl-（1- naphthalenes）Amino）Phenyl boric acid obtains compound 2.
Embodiment 4
The synthesis of compound 3
Synthesis step is same as the four-step reaction in embodiment 2, and methiodide benzene will be changed as 2- iodine naphthalenes in third step；4th
Step, changes into N- phenyl carbazole -3- boric acid by triphenylamine -4- boric acid, obtains compound 3.
Embodiment 5
The synthesis of compound 4
Synthesis step is same as the four-step reaction in embodiment 2, and methiodide benzene will be changed as 2- iodine naphthalenes in third step；4th
Step, changes into 6,9- diphenyl carbazole -3- boric acid by triphenylamine -4- boric acid, obtains compound 4.
Embodiment 6
The synthesis of compound 5
Synthesis step is divided into four steps, first three step is same as the preceding three-step reaction in embodiment 2, and methiodide benzene will be changed in third step
It is changed to 2- iodine naphthalenes；And four-step reaction is same as the three-step reaction in embodiment 2, only will change into 4- to methiodide benzene（Carbazole-
9- bases）Iodobenzene obtains compound 5.
Embodiment 7
The synthesis of compound 6
Synthesis step is divided into four steps, first three step is same as the preceding three-step reaction in embodiment 2, and methiodide benzene will be changed in third step
It is changed to 2- iodine naphthalenes；And four-step reaction is same as the three-step reaction in embodiment 2, and 3- phenyl clicks will be only changed into methiodide benzene
Azoles obtains compound 6.
Embodiment 8
The synthesis of compound 7
Synthesis step is same as the four-step reaction in embodiment 2, and methiodide benzene will be changed as 2- iodine naphthalenes in third step；4th
Step, changes into 8- phenyl dibenzothiophenes -2- boric acid by triphenylamine -4- boric acid, obtains compound 7.
Embodiment 9
The synthesis of compound 8
Synthesis step is same as the four-step reaction in embodiment 2, and only methiodide benzene will be changed as 2- iodine naphthalenes in third step；The
Triphenylamine -4- boric acid is changed into 8- phenyl dibenzofurans -2- boric acid, obtains compound 8 by four steps.
Embodiment 10
The synthesis of compound 9
Synthesis step is same as the four-step reaction in embodiment 2, and only methiodide benzene will be changed as 2- iodine naphthalenes in third step；The
Triphenylamine -4- boric acid is changed into 10- by four steps（2- naphthalenes）Anthracene -9- boric acid, obtains compound 9.
Embodiment 11
The synthesis of compound 10
Synthesis step is same as the four-step reaction in embodiment 2, and only methiodide benzene will be changed as 2- iodine naphthalenes in third step；The
Triphenylamine -4- boric acid is changed into pyrene -1- boric acid, obtains compound 10 by four steps.
Embodiment 12
The synthesis of compound 11
Synthesis step is same as the four-step reaction in embodiment 2, and only methiodide benzene will be changed as 2- iodine naphthalenes in third step；The
Triphenylamine -4- boric acid is changed into triphenylene -2- boric acid, obtains compound 11 by four steps.
Embodiment 13
The synthesis of compound 12
Synthesis step is same as the four-step reaction in embodiment 2, and only methiodide benzene will be changed as 2- iodine naphthalenes in third step；The
Triphenylamine -4- boric acid is changed into -6- boric acid in the wrong, obtains compound 12 by four steps.
Embodiment 14
The synthesis of compound 13
Synthesis step is same as the four-step reaction in embodiment 2, and 2,4-, bis- bromo nitrobenzenes only are changed into 2 in the first step,
Bis- bromo nitrobenzenes of 5-；Methiodide benzene will be changed in third step as 2- iodine naphthalenes；Triphenylamine -4- boric acid is changed into 4- by the 4th step（N-
Phenyl-N（1- naphthalenes）Amino）Phenyl boric acid obtains compound 13.
Embodiment 15
The synthesis of compound 14
Synthesis step is same as the four-step reaction in embodiment 2, and 2,4-, bis- bromo nitrobenzenes only are changed into 2 in the first step,
Bis- bromo nitrobenzenes of 5-；Methiodide benzene will be changed in third step as 2- iodine naphthalenes；Triphenylamine -4- boric acid is changed into hexichol by the 4th step
Bithiophene -4- boric acid, obtains compound 14.
Embodiment 16
The synthesis of compound 15
Synthesis step is same as the four-step reaction in embodiment 2, and 2,4-, bis- bromo nitrobenzenes only are changed into 2 in the first step,
Bis- bromo nitrobenzenes of 5-；Methiodide benzene will be changed in third step as 2- iodine naphthalenes；Triphenylamine -4- boric acid is changed into 8- benzene by the 4th step
Base dibenzothiophenes -2- boric acid, obtains compound 15.
Embodiment 17
The synthesis of compound 16
Synthesis step is same as the four-step reaction in embodiment 2, and 2,4-, bis- bromo nitrobenzenes only are changed into 2 in the first step,
Bis- bromo nitrobenzenes of 5-；Methiodide benzene will be changed in third step as 2- iodine naphthalenes；Triphenylamine -4- boric acid is changed into 8- benzene in the 4th step
Base dibenzofurans -2- boric acid, obtains compound 16.
Embodiment 18
The synthesis of compound 17
Synthesis step is same as the four-step reaction in embodiment 2, and 2,4-, bis- bromo nitrobenzenes only are changed into 2 in the first step,
Bis- bromo nitrobenzenes of 5-；Methiodide benzene will be changed in third step as 2- iodine naphthalenes；Triphenylamine -4- boric acid is changed into 10- in the 4th step
（2- naphthalenes）Anthracene -9- boric acid, obtains compound 17.
Embodiment 19
The synthesis of compound 18
Synthesis step is same as the four-step reaction in embodiment 2, and 2,4-, bis- bromo nitrobenzenes only are changed into 2 in the first step,
Bis- bromo nitrobenzenes of 5-；Methiodide benzene will be changed in third step as 2- iodine naphthalenes；Triphenylamine -4- boric acid is changed into 4- in the 4th step
（10-（2- naphthalenes）Anthracene -9- bases）Phenyl boric acid obtains compound 18.
Embodiment 20
The synthesis of compound 19
Synthesis step is same as the four-step reaction in embodiment 2, and 2,4-, bis- bromo nitrobenzenes only are changed into 2 in the first step,
Bis- bromo nitrobenzenes of 5-；Methiodide benzene will be changed in third step as 2- iodine naphthalenes；The 4th step by triphenylamine -4- boric acid change into pyrene -
1- boric acid obtains compound 19.
Embodiment 21
The synthesis of compound 20
Synthesis step is same as the four-step reaction in embodiment 2, only will change into 2,4-, bis- bromo nitrobenzenes in the first step
2,5- bis- bromo nitrobenzenes；Methiodide benzene will be changed in third step as 2- iodine naphthalenes；Triphenylamine -4- boric acid is changed into the 4th step
12- phenyl bends -6- boric acid, obtains compound 20.
Embodiment 22
The synthesis of compound 21
Synthesis step is same as the four-step reaction in embodiment 2, and 2,4-, bis- bromo nitrobenzenes only are changed into 2 in the first step,
Bis- bromo nitrobenzenes of 5-；Methiodide benzene will be changed in third step as 2- iodine naphthalenes；Triphenylamine -4- boric acid is changed into Sanya in the 4th step
Benzene -2- boric acid, obtains compound 21.
The Mass Spectrometer Method data and Elemental analysis data of gained compound 1-21 refer to table 1.
It is mass spectrum and Elemental analysis data of the compound of the present invention 1 to compound 21 below：
Embodiment 23
The Application Example of each compound of the present invention
Compare the performance of these hole mobile materials and fluorescent host material for convenience, the present invention devises a simple electricity
Luminescent device, we select HAT to hole injection layer material, and material is compared in hole mobile material NPB conducts.Organic luminous layer is by sending out
Light main body and dopant material composition, we are mixed using traditional light emitting host material EM1 as material, EM2 is compared as shining
The structure of miscellaneous material, wherein HAT, NPB, EM1, EM2 is respectively:
The structure of organic electroluminescence device is in the embodiment of the present invention：
Substrate/anode/hole injection layer (HIL)/hole transmission layer（HTL）/ organic luminous layer（EL）/ electron transfer layer
(ETL)/cathode.
Substrate can use the substrate in conventional organic luminescence device, such as：Glass or plastics.In the Organic Electricity of the present invention
Electroluminescence device selects glass substrate in making, and ITO makees anode material.
The various more arylamine for easily providing electronics can be used in electron injection material, it is possible to use more cyano of extreme electron deficient
Class material, such molecule usually use its lowest unoccupied molecular orbital（LUMO）To transmit electronics.Hole note used in the present invention
It is HAT to enter material.
Various tri-arylamine group materials may be used in hole transmission layer.The material stated in the present invention is in electroluminescence device
It can be used as hole mobile material, be compared with traditional hole mobile material NPB.
There are many plant for emitting layer material.The material stated in the present invention can be used as light emitting host material in electroluminescence device
Material, luminescent dopant material is EM2.
There are many plant for electron transport layer materials.In order to characterize the material stated in the present invention, we use common here
AlQ3 as electron transport material, it is therefore an objective to material property in more of the invention, do not lie in pursue device performance it is excellent.
Metal and its mixture structure, such as Mg may be used in cathode：Ag、Ca：Ag etc. or electron injecting layer/gold
Belong to layer structure, such as LiF/Al, Li2O/Al common cathode structure.It is selected in the organic electroluminescence device of the present invention makes
Cathode material is LiF/Al.
Embodiment 24
Compound in the present embodiment is prepared for multiple having altogether as the hole mobile material in organic electroluminescence device
Organic electroluminescence devices, structure are：ITO/HAT（5nm）/ hole mobile material（40nm）/EM1：EM2(30nm)/Alq3
（20nm）/LiF（0.5nm）/Al（150nm）；
One comparison organic electroluminescence device, hole mobile material select NPB, remaining organic electroluminescence device is selected
The material of the present invention.
Organic electroluminescence device preparation process is as follows in the present embodiment：
The glass plate for being coated with transparent conductive layer in commercial detergent is ultrasonically treated, is rinsed in deionized water,
In acetone：Ultrasonic oil removing in alcohol mixed solvent, is baked under clean environment and removes moisture content completely, 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 HAT is as hole injection layer on anode tunic, and evaporation rate 0.1nm/s, vapor deposition film thickness is 5nm；
The particular compound 1,3,4,6,7,8,11,13,14,15 in one layer of present invention is deposited again on hole injection layer
Or NPB, as hole transmission layer, evaporation rate 0.1nm/s, vapor deposition film thickness is 40nm；
The vacuum evaporation luminescent layer EM1 and EM2 on hole transmission layer（Ratio 95%：5%）, evaporation rate 0.1nm/s,
Vapor deposition total film thickness is 30nm；
One layer of AlQ3 of vacuum evaporation is distinguished on luminescent layer as electron transport material, evaporation rate 0.1nm/s,
Vapor deposition total film thickness is 20nm；
In electron transfer layer（ETL）Upper vacuum evaporation thickness is the LiF of 0.5nm as electron injecting layer, thickness 150nm
Cathode of the Al layers as device.
Organic electroluminescence device performance see the table below：
| Compound number | It is required that brightness cd/m2 | Voltage V | Current efficiency cd/A |
| NPB | 5000.00 | 6.8 | 25.1 |
| 1 | 5000.00 | 6.3 | 27.0 |
| 3 | 5000.00 | 6.5 | 27.2 |
| 4 | 5000.00 | 6.0 | 26.8 |
| 6 | 5000.00 | 6.1 | 28.1 |
| 7 | 5000.00 | 6.4 | 28.3 |
| 8 | 5000.00 | 6.2 | 28.1 |
| 11 | 5000.00 | 6.3 | 28.0 |
| 13 | 5000.00 | 6.6 | 27.9 |
| 14 | 5000.00 | 6.3 | 27.3 |
| 15 | 5000.00 | 6.2 | 27.6 |
Embodiment 25
Compound in the present embodiment is prepared for multiple having altogether as the hole mobile material in organic electroluminescence device
Organic electroluminescence devices, structure are：ITO/HAT（40nm）/NPB（40nm）/ light emitting host material：EM2(85%：15%,
30nm)/Alq3（20nm）/LiF（0.5nm）/Al（150nm）；
One comparison organic electroluminescence device, light emitting host material selection EM1, remaining organic electroluminescence device are selected
The material of the present invention.
Organic electroluminescence device preparation process is as follows in the present embodiment：
The glass plate for being coated with transparent conductive layer in commercial detergent is ultrasonically treated, is rinsed in deionized water,
In acetone：Ultrasonic oil removing in alcohol mixed solvent, is baked under clean environment and removes moisture content completely, 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 HAT is as hole injection layer on anode tunic, and evaporation rate 0.1nm/s, vapor deposition film thickness is 40nm；
One layer of NPB is deposited again on hole injection layer as hole transmission layer, evaporation rate 0.1nm/s, evaporation film
Thickness is 40nm；
Compound 1,9,11,12,17,18,19,20 in the vacuum evaporation luminescent layer present invention on hole transmission layer or
EM1, doping vapor deposition EM2（Ratio 85%：15%）, evaporation rate 0.1nm/s, vapor deposition total film thickness is 30nm；
One layer of AlQ3 of vacuum evaporation is distinguished on luminescent layer as electron transport material, evaporation rate 0.1nm/s,
Vapor deposition total film thickness is 20nm；
In electron transfer layer（ETL）Upper vacuum evaporation thickness is the LiF of 0.5nm as electron injecting layer, thickness 150nm
Cathode of the Al layers as device.
Luminescent device performance see the table below：
| Compound number | It is required that brightness cd/m2 | Voltage V | Current efficiency cd/A |
| EM1 | 5000.00 | 6.8 | 25.1 |
| 1 | 5000.00 | 6.3 | 26.9 |
| 9 | 5000.00 | 6.4 | 27.3 |
| 11 | 5000.00 | 6.3 | 27.7 |
| 12 | 5000.00 | 6.6 | 26.7 |
| 17 | 5000.00 | 6.2 | 28.1 |
| 18 | 5000.00 | 6.1 | 28.3 |
| 19 | 5000.00 | 6.5 | 28.5 |
| 20 | 5000.00 | 6.0 | 28.0 |
The above result shows that novel organic luminescent material of the invention is used for organic electroluminescence device, it can be effective
Landing voltage is reduced, current efficiency is improved, is hole mobile material and light emitting host material of good performance.
Although the present invention is described in conjunction with the embodiments, the invention is not limited in above-described embodiments, should manage
Solution, under the guiding of present inventive concept, those skilled in the art can carry out various modifications and improve, and appended claims summarise
The scope of the present invention.
Claims (2)
1. one kind is for the hole mobile material or the compound of hole-injecting material in organic electroluminescence device, selected from following
Structural formula：
2. a kind of organic electroluminescence device, including substrate and anode layer, organic light emission on the substrate are sequentially formed
Functional layer and cathode layer；
The organic luminescence function layer includes hole transmission layer, organic luminous layer and electron transfer layer, it is characterised in that：
The host material of the hole transmission layer contains the hole described in claim 1 in organic electroluminescence device and passes
The compound of defeated material or hole-injecting material.
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