CN108623479A - A kind of organic luminescent compounds and its preparation method and application - Google Patents
A kind of organic luminescent compounds and its preparation method and application Download PDFInfo
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- CN108623479A CN108623479A CN201710158300.6A CN201710158300A CN108623479A CN 108623479 A CN108623479 A CN 108623479A CN 201710158300 A CN201710158300 A CN 201710158300A CN 108623479 A CN108623479 A CN 108623479A
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Abstract
The present invention provides a kind of compound and its preparation method and application, compound provided by the invention has 1 structure of chemical formula,[chemical formula 1], by selecting specific mother nucleus structure and substituent A, B, Ar1And Ar2So that obtained compound is applied to the luminous efficiency raising of device after organic electroluminescence device, and service life is long.
Description
Technical field
The present invention relates to organic luminescent device fields more particularly to a kind of compound and its preparation method and application.
Background technology
Organic luminescent device (OLED) is made of the organic matter layer being inserted between cathode, anode and cathode and anode,
Wherein, organic layer is generally made of multilayered structure, such as include hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and
Electron injecting layer etc.；Its effect is to improve the efficiency and stability of organic electroluminescence device.
Present Portable Displays lead to the higher consumption of benchmark Portable Displays requirement with the increase of panel size
Electric power.Thus, the battery of limited power supply source is difficult meet demand in Portable Displays, and uses organic electroluminescent
When device, efficiency and service life are must to solve the problems, such as.Efficiency and service life, driving voltage are coherent mutually, and general efficiency increases
Start voltage reduction, and organic matter can be caused by starting the resistance heating (Joule heating) occurred when voltage reduction driving
It crystallizes, as a result service life increased tendency.But improve the efficiency that above-mentioned organic layer is unable to organic electroluminescence device.Because respectively
Energy level and T1 values, the inherent characteristic of substance between organic layer（Degree of excursion, interfacial characteristics etc.）It can be only achieved and prolong when equal optimal combination
Long light-emitting device life period and raising efficiency of luminescent device purpose.
Traditional hole transmission layer develops the fast object of hole degree of excursion (hole mobility) to reduce driving voltage
Matter develops packing density (packing density) high HOMO valences to improve hole degree of excursion and is connect with luminescent layer HOMO valences
Close substance, but degree of excursion fast substance in hole generally results in the efficiency reduction of luminescent device.Because of organic electroluminescence device hole
When degree of excursion is faster than electronics degree of excursion (electron mobility), it may appear that electronics is unbalanced (charge unbalance)
Phenomenon eventually leads to the problem of luminous efficiency reduction and service life reduction.And use packing density (packing density) low
Substance reduces hole degree of excursion, and then adjusts the electronic equalizing situation in luminescent layer, but will appear low packing density
(packing density) and then driving voltage is improved, and the raising of driving voltage can increase electronics heating and shorten device lifetime,
Therefore it provides a kind of hole transport layer material makes it not only increase its service life applied to electroluminescent device, but also improve its hair
Light efficiency is current problem to be solved.
Invention content
In consideration of it, technical problem to be solved by the present invention lies in a kind of compound of offer and its preparation method and application,
Compound of the present invention is applied to luminescent device as hole transport layer material so that obtained device not only luminous efficiency
Height, and service life is long.
The present invention provides a kind of compounds, have [chemical formula 1] structure,
[chemical formula 1]
Wherein, the Ar1、Ar2Independent aryl, substituted or non-substituted C6 ~ C50 selected from substituted or non-substituted C6 ~ C50
Condensed ring radical, the aromatic amino of substituted or non-substituted C5 ~ C50 or the heterocyclic aryl of substituted or non-substituted C5 ~ C50；It is preferred that
, Ar1、Ar2Independent aryl, the heterocycle of substituted or non-substituted C12 ~ C30 selected from substituted or non-substituted C12 ~ C30 are fragrant
The condensed ring radical of base, the aromatic amino of substituted or non-substituted C12 ~ C30, substituted or non-substituted C12 ~ C30；More preferably replace
Or the aryl of non-substituted C18 ~ C25, the heterocyclic aryl of substituted or non-substituted C15 ~ C20, substituted or non-substituted C18 ~ C25
Aromatic amino, substituted or non-substituted C15 ~ C25 condensed ring radical；
The independent cycloalkanes selected from hydrogen, the alkyl of substituted or non-substituted C1 ~ C30, substituted or non-substituted C3 ~ C30 of described A, B
Base, the aryl of substituted or non-substituted C6 ~ C60, the condensed ring radical of substituted or non-substituted C8 ~ C60 or described A, B and place
Carbon forms condensed ring；Preferably, the independent alkyl, substituted or non-substituted selected from hydrogen, substituted or non-substituted C5 ~ C15 of described A, B
The naphthenic base of C6 ~ C30, the aryl of substituted or non-substituted C12 ~ C30, substituted or non-substituted C13 ~ C40 condensed ring radical or
The carbon of A, B and place described in person form condensed ring；It is the alkyl of more preferably substituted or non-substituted C8 ~ C10, substituted or non-substituted
The naphthenic base of C8 ~ C15, the aryl of substituted or non-substituted C18 ~ C25, substituted or non-substituted C18 ~ C25 condensed ring radical or
Described A, B and the carbon at place form condensed ring；Specifically, described A, B are independent selected from hydrogen, methyl, ethyl, propyl, isopropyl, fourth
Base, isobutyl group, tertiary butyl, amyl, hexyl, 2- ethylhexyls, phenyl, xenyl, naphthalene, anthryl, phenanthryl or fluorenyl；
Wherein, the substituted alkyl, substituted naphthenic base, substituted aryl, substituted aromatic amino, substituted heterocyclic aryl
With the preferably independent selection alkyl of C1 ~ C30 of the substituent group on substituted condensed ring radical, the virtue of the naphthenic base of C3 ~ C30, C6 ~ C60
The condensed ring radical of base, the aryl of unsubstituted C6 ~ C60 or C8 ~ C60；The preferably alkyl of C5 ~ C15, the naphthenic base of C6 ~ C30, C12
The aryl of the aryl of ~ C30 or the condensed ring of C13 ~ C40, the more preferably alkyl of C8 ~ C10, the naphthenic base of non-C8 ~ C15, C18 ~ C25
Or the condensed ring radical of C18 ~ C25；Most preferably methyl, methyl, ethyl, propyl, isopropyl, butyl, isobutyl group, tertiary butyl, amyl,
Hexyl, 2- ethylhexyls, phenyl, xenyl, naphthalene, anthryl, phenanthryl or fluorenyl；Hetero atom on the heterocyclic aryl is preferably
One or more of nitrogen, oxygen and sulphur.
Preferably, Ar1And Ar2It is independent to be selected from methyl, ethyl, the fluoro- ethyls of 2-, 2- cyano-propyls, isopropyl, tertiary fourth
Base, pentyl, heptane base, dodecyl, formula（001）Formula（045）Structure；
Formula（001）, formula（002）, formula（003）, formula（004）,
Formula（005）, formula（006）, formula（007）, formula（008）, formula（009）,
Formula（010）, formula（011）, formula（012）, formula（013）, formula（014）,
Formula（015）, formula（016）, formula（017）, formula（018）, formula（019）,
Formula（020）, formula（021）, formula（022）, formula（023）, formula（024）, formula（025）,
Formula（026）, formula（027）, formula（028）, formula（029）,
Formula（030）, formula（031）, formula（032）,
Formula（033）, formula（034）, formula（035）, formula（036）, formula（037）,
Formula（038）, formula（039）, formula（040）, formula（041）,
Formula（042）, formula（043）, formula（044）, formula（045）；
Wherein, in substituent groupIndicate connecting key, simultaneouslyIt is not fixed to be connected on any one carbon and indicates that it can be
Any position of place aromatic rings.
Preferably, the compound is chemical formula（1-1）, chemical formula（1-2）, chemical formula（1-3）Or chemical formula（1-4）,
Chemical formula（1-1）, chemical formula（1-2）, chemical formula（1-3）, chemical formula（1-4）.
Preferably, the compound is structure shown in any one of chemical formula P1 ~ chemical formula P60：
P1, P2, P3,
P4, P5, P6,
P7, P8, P9,
P10, P11, P12,
P13, P14, P15,
P16, P17, P18,
P19, P20, P21,
P22, P23, P24,
P25, P26, P27,
P28, P29, P30,
P31, P32, P33,
P34, P35, P36,
P37, P38, P39,
P40, P41, P42,
P43, P44, P45,
P46, P47, P48,
P49, P50, P51,
P52, P53, P54,
P55, P56, P57,
P58, P59, P60.
Indeno fluorene kind derivative provided by the invention is in luminous efficiency and has preferable performance in terms of the service life.
The present invention provides a kind of preparation methods of indeno fluorene kind derivative, including：
The compound of the compound of Formulas I structure and Formula II structure is reacted, the indenofluorene class for obtaining 1 structure of chemical formula derives
Object；
Formulas I；Formula II；Chemical formula 1；
Wherein, X is halogen；The Ar1、Ar2It is independent aryl selected from substituted or non-substituted C6 ~ C50, substituted or non-substituted
The condensed ring radical of C6 ~ C50, the aromatic amino of substituted or non-substituted C5 ~ C50 or substituted or non-substituted C5 ~ C50 heterocycle virtue
Base；
The independent cycloalkanes selected from hydrogen, the alkyl of substituted or non-substituted C1 ~ C30, substituted or non-substituted C3 ~ C30 of described A, B
Base, the aryl of substituted or non-substituted C6 ~ C60, the condensed ring radical of substituted or non-substituted C8 ~ C60 or described A, B and place
Carbon forms condensed ring；
The preparation process of indeno fluorene kind derivative provided by the invention is simple, and has in luminous efficiency and in terms of the service life preferable
Performance.
The present invention provides a kind of luminescent devices, including the indeno fluorene kind derivative described in above-mentioned technical proposal.
Indeno fluorene kind derivative provided by the invention can be used for preparing at or it is non-to at luminescent device, this photophore
Part has preferable luminescent properties.
The preparation process of indeno fluorene kind derivative provided by the invention is simple, and has in luminous efficiency and in terms of the service life
Preferable performance.
The present invention provides a kind of luminescent devices, including the indeno fluorene kind derivative described in above-mentioned technical proposal.In this hair
In bright, the indeno fluorene kind derivative is consistent with the indeno fluorene kind derivative described in above-mentioned technical proposal, and details are not described herein.
In the present invention, the luminescent device preferably includes cathode, anode and the one or more being arranged between the cathode and anode
Compound layer, the compound layer include the indeno fluorene kind derivative described in above-mentioned technical proposal.In the present invention, the chemical combination
Nitride layer can be made of indeno fluorene kind derivative completely, can also be by the mixture group of indeno fluorene kind derivative and other substances
At.In the present invention, the compound layer includes hole injection layer, hole transmission layer, had both had hole injection but also with hole
The technical ability layer of transmission, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer, had both had electronics biography at electronic barrier layer
Defeated one or more of the technical ability layer but also with electron injection.In the present invention, the hole injection layer, hole transmission layer,
Both had hole injection but also with conventional hole injecting material, hole transport object may be used in the technical ability layer of hole transport
Matter had both had substance of the hole injection but also with hole transport technical ability, can also use the substance of electron-transporting material production.
In the present invention, the compound layer preferably includes hole transmission layer, and the hole transmission layer includes above-mentioned technology
Indeno fluorene kind derivative described in scheme.In the present invention, in the present invention, the hole transmission layer can be red, green
Or blue light-emitting layer.
In the present invention, the compound layer preferably includes hole transmission layer, and the hole transmission layer includes above-mentioned technology
Indeno fluorene kind derivative described in scheme.
The present invention does not have the preparation method of the luminescent device special limitation, use well known to those skilled in the art
The preparation method of luminescent device is prepared.In the present invention, film vapor deposition, electron beam evaporation, physics gas can be utilized
Mutually the methods of deposition evaporation metal, conductive oxide and their alloy on substrate forms anode；Cathode
Preparation method is consistent with anode preparation method；Hole injection layer, hole transport are deposited in order in the cathode surface being prepared
Layer, luminescent layer, air barrier and electron transfer layer.In the present invention, prepare hole injection layer, hole transmission layer, luminescent layer,
High molecular material solvent engineering can be used during the multilayered structures such as hole blocking layer and electron transfer layer and replace spin-coating
（spin-coating）, strip molding（tape-casting）, scraping blade method（doctor-blading）, silk-screen printing（Screen-
Printing）, the evaporation coating methods such as ink jet printing or thermal imaging (Thermal-Imaging) reduce the preparation of the number of plies.
Luminescent device provided by the invention is prepared using the indeno fluorene kind derivative described in above-mentioned technical proposal.It is this
Luminescent device has preferable luminescent properties, can front shine, back side illuminated or lighting at two sides.
In the present invention, the luminescent material can be used for organic luminescent device（OLED）, organic photovoltaic cell（OSC）, electricity
The philosophical works（e-Paper）, Organophotoreceptor（OPC）, organic transistor, polycrystalline organic thin film or ink-jet printing material.
Raw materials used following embodiment of the present invention is commercial goods.
Specific implementation mode
The technical scheme in the embodiments of the invention will be clearly and completely described below, it is clear that described embodiment is only
It is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, ordinary skill
Personnel it is improved or retouching all other example, shall fall within the protection scope of the present invention.
The synthesis of 1 Sub1 of embodiment
The synthesis of Sub1-1-1
Under condition of nitrogen gas, add 5- bromoacenaphthylenes 24.4g (105.52 mmol), 2- acetylphenyl boronic acids 17.3g in order
(105.52 mmol), potassium carbonate 18.23g (131.9 mmol), Isosorbide-5-Nitrae-dioxane 340ml, are stirred under the conditions of 70 DEG C, after
Continuous that tetra-triphenylphosphine palladium 2.54g (2.19 mmol) is added, distilled water 40ml return stirrings are stayed overnight.Organic layer is detached, methanol is added
Solid is precipitated in 100ml, and distilled water/methanol extraction liquid separation is used after solid filtering, adds toluene 300ml return stirrings complete in product
Cooling room temperature after fully dissolved, crosses filter solid and is washed later with toluene.Under the conditions of 50 DEG C, oven drying obtains 16.2g products
Sub1-1-1, yield 56.8%, theoretical value=270.10 (measured value C20H14O=270.32).
According to the synthetic method of Sub1-1-1, Sub1-2-1 and Sub1-3-1 is prepared with identical mole ratio, is prepared
The reaction mass of Sub1-2-1 and Sub1-3-1 is shown in Table 1.
Table 1 prepares the reaction mass of Sub1-2-1 and Sub1-3-1
The synthesis of Sub1-1-2
Under condition of nitrogen gas, tetrahydrofuran 300ml stirrings are added in 9.13g (33.77 mmol) intermediates Sub1-1-1.It is 0 DEG C cooling
Methyl-magnesium-chloride 101.3ml (303.98 mmol) is slowly added dropwise afterwards, after being stirred overnight, in 1.5L containers in reaction solution slowly
Ammonium chloride solution is added dropwise, extracts organic layer with ethyl acetate/distilled water, anhydrous sodium sulfate drying uses silica gel after being concentrated under reduced pressure
Pillar (ethyl acetate:Hex=1:9~1:3) isolated 6.29g white products Sub1-1-2, yield 65%, theoretical value=
286.14 (measured value C21H18O=286.37).
According to the synthetic method of Sub1-1-2, Sub1-2-2 ~ Sub1-4-2 is prepared with identical mole ratio, is prepared
The reaction mass of Sub1-2-2 ~ Sub1-4-2 is shown in Table 2.
Table 2 prepares the reaction mass of Sub1-2-2 ~ Sub1-4-2
The synthesis of Sub1-1-3
Under condition of nitrogen gas, by 4.99g (17.41mmol) intermediate Sub1-1-2 with after being completely dissolved in dichloromethane 270ml, drop
Add 5.65ml (87.09mmol) methanesulfonic acid (MSA).In reaction solution plus after methanol 200ml, it is concentrated under reduced pressure, uses methanol 200ml
Solid is precipitated in 1 hour in stirring.Use methanol cleaning product, after using acetone 400ml return stirrings to stay overnight again after filtering, cooling chamber
Warm filtering product.Using acetone 200ml cleaning products, under the conditions of 70 DEG C, it is dried to obtain 3.27g product Sub1-1-3, yield
It is 70%, theoretical value=268.13 (measured value C21H16=268.35).
According to the synthetic method of Sub1-1-3, Sub1-2-3 ~ Sub1-4-3 is prepared with identical mole ratio, is prepared
The reaction mass of Sub1-2-3 ~ Sub1-4-3 is shown in Table 3.
Table 3 prepares the reaction mass of Sub1-2-3 ~ Sub1-4-3
The synthesis of Sub1-1
It is completely dissolved with chloroform 600ml in reaction vessel plus after 31.4g (116.9mmol) intermediates Sub1-1-3, room temperature item
Under part plus N- bromo-succinimides 24.98g (140.4mmol) is stirred 1 hour, and methanol is slowly added dropwise in reaction solution after reaction
Stirring 2 hours inside 1300ml, the solid of generation are filtered under diminished pressure to obtain 20.3g product Sub1-1, yield 50%, and theoretical value=
346.04 (measured value C21H15Br=347.25).
According to the synthetic method of Sub1-4, Sub1-2 ~ Sub1-4 is prepared with identical mole ratio, prepare Sub2-4 ~
The reaction mass of Sub4-4 is shown in Table 3.
Table 4 prepares the reaction mass of Sub1-2 ~ Sub1-4
The synthesis of 2 Sub2 of embodiment
The synthesis of Sub 2-3
In reaction vessel in order plus 2- bromo biphenyls (32.2g, 138mmol), two fluorenes -2- amine of 9,9'- spiral shells (41.6g,
125.5mmol), three（Dibenzalacetone）Two palladiums (5.74g, 6.3mmol), tri-tert-butylphosphine (2.54g, 12.5mmol),
After sodium tert-butoxide (36.2g, 376.4mmol), toluene 1320mL, reacted under the conditions of 100 DEG C.Ether after reaction terminates
Organic matter is extracted with water, enriched product silicagel column and recrystallization method obtain 46.7g productions after organic layer is dried with magnesium sulfate
Object Sub2-3, yield 77%.
The synthesis of Sub 2-14
Add 3- (4- bromophenyls) -9- phenyl -9H- carbazoles (55g, 138mmol), two fluorenes of 9,9'- spiral shells-in reaction vessel in order
2- amine (41.6g, 125.5mmol), three（Dibenzalacetone）Two palladiums (5.74g, 6.3mmol), tri-tert-butylphosphine (2.54g,
12.5mmol), it is reacted under the conditions of 100 DEG C after sodium tert-butoxide (36.2g, 376.4mmol), toluene 1320mL.Reaction knot
Shu Yihou ether and water extract organic matter, concentration, product silicagel column and recrystallization side after organic layer is dried with magnesium sulfate
Method obtains 57g product Sub2-14, yield 70%.
The synthesis of Sub2-28
In reaction vessel in order plus 4- bromobenzenes simultaneously [b, d] furans (34g, 138mmol), triphenylene -2- amine (30.5g,
125.5mmol), three（Dibenzalacetone）Two palladiums (5.74g, 6.3mmol), tri-tert-butylphosphine (2.54g, 12.5mmol),
It is reacted under the conditions of 100 DEG C after sodium tert-butoxide (36.2g, 376.4mmol), toluene 1320mL.After reaction terminates, use
Ether and water extract organic matter, and organic layer is dried with magnesium sulfate and concentrated, and product silicagel column and recrystallization method obtain 41g products
Sub2-28, yield 80%.
It is prepared containing Ar using the synthetic method described in Sub2-3, Sub2-14, Sub2-28 in the synthesis of Sub21
And Ar2Intermediate Sub2-1 ~ Sub2-54 of substituent group, concrete structure formula is as follows, and Structural Identification is carried out to obtained compound,
Its mass spectrum is shown in Table 3.
The mass spectrometry value of 3 Sub2-1 of table ~ Sub2-54
The synthesis of 3 target product of embodiment
The synthesis of P1
Add Sub1-1 (14.83g, 42.7mmol), Sub2-1 (15g, 46.9mmol), three in reaction vessel in order（Two is sub-
Benzylacetone）Two palladiums (1.95g, 2.13mmol), tri-tert-butylphosphine (0.86g, 4.3mmol), sodium tert-butoxide (12.3g,
128mmol), toluene 300mL is stirred under the conditions of 100 DEG C, and reaction with dichloromethane and water extracts organic matter after terminating, organic
Layer is dried with anhydrous magnesium sulfate.Product is concentrated under reduced pressure, and product silicagel column and recrystallization method obtain 17.57g's (70%) later
Product P1.
The synthesis of P7
By Sub 1-1 (14.9g, 42.9mmol), Sub 2-7 (26.4g, 47.2mmol), three（Dibenzalacetone）Two
Palladium (1.97g, 2.15mmol), tri-tert-butylphosphine (0.87g, 4.3mmol), sodium tert-butoxide (12.4g, 128.8mmol), toluene
The substances such as 450mL obtain the product P7 of 23.74g (67%) according to P1 synthetic methods.
The synthesis of P13
Use Sub 1-1 (10g, 28.9mmol), Sub 2-13 (16.75g, 31.8mmol), three（Dibenzalacetone）
Two palladiums (1.32g, 1.45mmol), tri-tert-butylphosphine (0.59g, 2.89mmol), sodium tert-butoxide (8.34g, 86.8mmol),
The substances such as toluene 250mL obtain the product P13 of 17.65g (77%) according to P1 synthetic methods.
The synthesis of P17
Use Sub1-1 (21.2g, 61.1mmol), Sub2-17 (48.52g, 67.3mmol), three（Dibenzalacetone）Two palladiums
(2.8g, 3.06mmol), tri-tert-butylphosphine (1.24g, 6.11mmol), sodium tert-butoxide (17.63g, 183.4mmol), toluene
The substances such as 500mL obtain the product P17 of 33.78g (56%) according to P1 synthetic methods.
The synthesis of P23
Use Sub 1-1 (7.7g, 22.1mmol), Sub 2-23 (9.61g, 24.3mmol), three（Dibenzalacetone）
Two palladiums (1.01g, 1.10mmol), tri-tert-butylphosphine (0.45g, 2.21mmol), sodium tert-butoxide (6.37g,
66.3mmol), the substances such as toluene 200mL obtain the product P23 of 7.46g (51%) according to P1 synthetic methods.
The synthesis of P29
Use Sub 1-1 (20.1g, 57.85mmol), Sub 2-29 (30g, 63.63mmol), three（Dibenzalacetone）
Two palladiums (2.64g, 2.89mmol), tri-tert-butylphosphine (1.17g, 5.78mmol), sodium tert-butoxide (16.7g,
173.5mmol), the substances such as toluene 600mL obtain the product P29 of 28.17g (66%) according to P1 synthetic methods.
The synthesis of P33
Use Sub1-1 (16g, 46.1mmol), Sub 2-33 (28.3g, 50.7mmol), three（Dibenzalacetone）Two
Palladium (2.11g, 2.3mmol), tri-tert-butylphosphine (0.93g, 4.6mmol), sodium tert-butoxide (13.3g,
138.3mmol), the substances such as toluene 450mL obtain the product P33 of 25.83g (68%) according to P1 synthetic methods.
The synthesis of P36
Use Sub1-1 (21.22g, 61.1mmol), Sub2-36 (33.75g, 67.3mmol), three（Dibenzylidene third
Ketone）Two palladiums (2.8g, 3.06mmol), tri-tert-butylphosphine (1.24g, 6.11mmol), sodium tert-butoxide (17.63g,
183.4mmol), the substances such as toluene 500mL obtain the product P36 of 28.15g (60%) according to P1 synthetic methods.
The synthesis of P41
Use Sub 1-1 (20g, 57.85mmol), Sub 7-41 (30g, 63.63mmol), three（Dibenzalacetone）Two
Palladium (2.64g, 2.89mmol), tri-tert-butylphosphine (1.17g, 5.78mmol), sodium tert-butoxide (16.7g,
173.5mmol), the substances such as toluene 600mL obtain the product P41 of 22.1g (46%) according to P1 synthetic methods.
The synthesis of P46
Use Sub 1-1 (16.2g, 46.7mmol), Sub 2-46 (29,51.3mmol), three（Dibenzalacetone）
Two palladiums (2.14g, 2.33mmol), tri-tert-butylphosphine (0.94g, 4.67mmol), sodium tert-butoxide (13.5g, 140mmol),
The substances such as toluene 390mLL obtain the product P46 of 17.42g (45%) according to P1 synthetic methods.
Using the method described in P1 in the synthesis of target product, the compound system synthesized according to embodiment 1 and embodiment 2
Standby to obtain indenofluorene class target compound P1 ~ P60, mass spectrometry value is indicated in table 4：
P1, P2, P3,
P4, P5, P6,
P7, P8, P9,
P10, P11, P12,
P13, P14, P15,
P16, P17, P18,
P19, P20, P21,
P22, P23, P24,
P25, P26, P27,
P28, P29, P30,
P31, P32, P33,
P34, P35, P36,
P37, P38, P39,
P40, P41, P42,
P43, P44, P45,
P46, P47, P48,
P49, P50, P51,
P52, P53, P54,
P55, P56, P57,
P58, P59, P60.
The mass spectrometry value of 4 target product P1 ~ P60 of table
The preparation of 4 organic luminescent device of embodiment
Compound prepared by embodiment 3 is used to prepare green organic electrofluorescence device as hole transport layer material, specifically
Preparation method is：
ITO first（Anode）N1- (2- naphthalenes)-N4, N4- bis- (4- (2- naphthalenes (phenyl) amino) phenyl)-N1- benzene is deposited above
And then compound P1 60nm, main substance 4 that the present invention synthesizes is deposited in base benzene-Isosorbide-5-Nitrae-diamines (" 2-TNATA ") 60nm,
Bis- carbazoles of 4'-N, N'--biphenyl (" CBP "), and dopant three（2- phenylpyridines）Iridium (" Ir (ppy) 3 ") 90:10 weights
Amount is than mixing vapor deposition 30nm, vapor deposition hole blocking layer (" BAlq ") 10nm thickness, vapor deposition " Alq3 " 40nm thickness, vapor deposition electricity
Sub- implanted layer LiF0.2nm, evaporation cathode Al 150nm forms prepare organic luminescent device.
Equally, it changes P1 into other compounds described in embodiment 3 of the present invention, is then prepared a series of
Organic luminescent device.
[comparative example 1] ~ [comparative example 3]
Device is prepared according to 1 same method of embodiment, wherein comparing 1 alternative compounds P1 of compound in [comparative example 1], [comparing
Example 2] 2 alternative compounds P1 of middle comparison compound, [comparative example 3] middle relatively 3 alternative compounds P1 of compound.
(comparing compound 1) (comparing compound 2) (comparing compound 3)
1 ~ embodiment of the embodiment of the present invention 60, organic luminescent device biasing (bias prepared by 1 ~ comparative example of comparative example 3
Voltage the PR650 spectral scan radiancy measurement examination electroluminescence characters of PhotoResearch companies of the U.S.) are used later
(EL), under 5000Cd/ ㎡ Benchmark brightness, the standby service life equipment Test T95 of mcscience corporations is used.Measurement result is in table 5
It indicates.
Table 5
As can be seen from Table 5, the compound of the present invention is applied to organic luminescent device relative to existing sky as hole material
Cave material can improve the luminous efficiency and service life of luminescent device.
The explanation of above example is only intended to facilitate the understanding of the method and its core concept of the invention.It should be pointed out that pair
For those skilled in the art, without departing from the principle of the present invention, the present invention can also be carried out
Some improvements and modifications, these improvement and modification are also fallen within the protection scope of the claims of the present invention.
Claims (10)
1. a kind of compound has 1 structure of chemical formula,
[chemical formula 1]
Wherein, the Ar1、Ar2The independent Ar1、Ar2Independent aryl selected from substituted or non-substituted C6 ~ C50, substitution
Or aromatic amino or the substituted or non-substituted C5 ~ C50 of the condensed ring radical of non-substituted C6 ~ C50, substituted or non-substituted C5 ~ C50
Heterocyclic aryl；Described A, B it is independent selected from hydrogen, the alkyl of substituted or non-substituted C1 ~ C30, substituted or non-substituted C3 ~
The naphthenic base of C30, the aryl of substituted or non-substituted C6 ~ C60, the condensed ring radical of substituted or non-substituted C8 ~ C60 or the A,
B and the carbon at place form condensed ring.
2. compound according to claim 1, which is characterized in that described A, B are independent selected from hydrogen, substituted or non-substituted
The alkyl of C5 ~ C15, the naphthenic base of substituted or non-substituted C6 ~ C30, substituted or non-substituted C12 ~ C30 aryl, substitution or
The condensed ring radical of non-substituted C13 ~ C40 or described A, B and the carbon at place form condensed ring.
3. compound according to claim 1, which is characterized in that described A, B are independent selected from hydrogen, methyl, ethyl, third
Base, isopropyl, butyl, isobutyl group, tertiary butyl, amyl, hexyl, 2- ethylhexyls, phenyl, xenyl, naphthalene, anthryl, phenanthryl
Or fluorenyl.
4. compound according to claim 1, which is characterized in that the Ar1And Ar2It is independent selected from substituted or non-substituted
The aryl of C12 ~ C30, the condensed ring radical of substituted or non-substituted C13 ~ C40, substituted or non-substituted C12 ~ C30 aromatic amino
Or the heterocyclic aryl of substituted or non-substituted C12 ~ C30.
5. compound according to claim 1, which is characterized in that Ar1Or Ar2It is independent to be selected from methyl, ethyl, the fluoro- second of 2-
Base, 2- cyano-propyls, isopropyl, tertiary butyl, pentyl, heptane base, dodecyl, formula（001）~ formula（045）Structure；
Formula（001）, formula（002）, formula（003）, formula（004）,
Formula（005）, formula（006）, formula（007）, formula（008）, formula（009）,
Formula（010）, formula（011）, formula（012）, formula（013）, formula（014）,
Formula（015）, formula（016）, formula（017）, formula（018）, formula（019）,
Formula（020）, formula（021）, formula（022）, formula（023）, formula（024）, formula（025）,
Formula（026）, formula（027）, formula（028）, formula（029）,
Formula（030）, formula（031）, formula（032）,
Formula（033）, formula（034）, formula（035）, formula（036）, formula（037）,
Formula（038）, formula（039）, formula（040）, formula（041）,
Formula（042）, formula（043）, formula（044）, formula（045）；
Wherein, in substituent groupIndicate connecting key, simultaneouslyIt is not fixed to be connected on any one carbon and indicates that it can be
Any position of place aromatic rings.
6. compound according to claim 1, which is characterized in that the compound is chemical formula（1-1）, chemical formula（1-
2）, chemical formula（1-3）Or chemical formula（1-4）,
Chemical formula（1-1）, chemical formula（1-2）, chemical formula（1-3）, chemical formula（1-4）.
7. compound according to claim 1, which is characterized in that the compound has any one of formula P1 ~ formula P60
Shown in structure：
P1, P2, P3,
P4, P5, P6,
P7, P8, P9,
P10, P11, P12,
P13, P14, P15,
P16, P17, P18,
P19, P20, P21,
P22, P23, P24,
P25, P26, P27,
P28, P29, P30,
P31, P32, P33,
P34, P35, P36,
P37, P38, P39,
P40, P41, P42,
P43, P44, P45,
P46, P47, P48,
P49, P50, P51,
P52, P53, P54,
P55, P56, P57,
P58, P59, P60.
8. a kind of preparation method of the compound described in claim 1 ~ 7 any one, including：
The compound of the compound of Formulas I structure and Formula II structure is reacted, the indeno acenaphthylene class for obtaining 1 structure of chemical formula is spread out
Biology；
Formulas I；Formula II；Chemical formula 1；
Wherein, the Ar1、Ar2Independent aryl, substituted or non-substituted C6 ~ C50 selected from substituted or non-substituted C6 ~ C50
Condensed ring radical, the aromatic amino of substituted or non-substituted C5 ~ C50 or the heteroaryl of substituted or non-substituted C5 ~ C50；
The independent cycloalkanes selected from hydrogen, the alkyl of substituted or non-substituted C1 ~ C30, substituted or non-substituted C3 ~ C30 of described A, B
Base, the aryl of substituted or non-substituted C6 ~ C60, the condensed ring radical of substituted or non-substituted C8 ~ C60 or described A, B and place
Carbon formed condensed ring.
Described in compound or claim 8 9. a kind of organic electroluminescence device, including described in claim 1 ~ 7 any one
Preparation method prepare compound.
10. a kind of organic photoelectrical material, which is characterized in that including the compound or right described in claim 1 ~ 7 any one
It is required that compound prepared by the preparation method described in 8；The organic photoelectrical material includes organic photovoltaic cell, Electronic Paper, organic
Photoreceptor or organic transistor and ink-jet printing material.
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| CN108822018A (en) * | 2017-05-05 | 2018-11-16 | 吉林奥来德光电材料股份有限公司 | Electroluminescent organic material and preparation method thereof and organic electroluminescence device |
| CN114790145A (en) * | 2022-06-08 | 2022-07-26 | 上海钥熠电子科技有限公司 | Arylamine compound containing indenofluorene group and organic electroluminescent device |
| CN115894254A (en) * | 2021-09-30 | 2023-04-04 | 广州华睿光电材料有限公司 | Organic compound, mixture, composition and organic electronic device |
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| WO2011081429A2 (en) * | 2009-12-30 | 2011-07-07 | 주식회사 두산 | Organic compound, and organic electroluminescent device using same |
| KR101503796B1 (en) * | 2014-05-08 | 2015-03-18 | 성균관대학교산학협력단 | Organic electroluminescent compound, producing method of the same and organic electroluminescent device including the same |
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| WO2011081429A2 (en) * | 2009-12-30 | 2011-07-07 | 주식회사 두산 | Organic compound, and organic electroluminescent device using same |
| KR101503796B1 (en) * | 2014-05-08 | 2015-03-18 | 성균관대학교산학협력단 | Organic electroluminescent compound, producing method of the same and organic electroluminescent device including the same |
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| CN108822018A (en) * | 2017-05-05 | 2018-11-16 | 吉林奥来德光电材料股份有限公司 | Electroluminescent organic material and preparation method thereof and organic electroluminescence device |
| CN115894254A (en) * | 2021-09-30 | 2023-04-04 | 广州华睿光电材料有限公司 | Organic compound, mixture, composition and organic electronic device |
| CN114790145A (en) * | 2022-06-08 | 2022-07-26 | 上海钥熠电子科技有限公司 | Arylamine compound containing indenofluorene group and organic electroluminescent device |
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