CN109369660A - Luminous organic material and its preparation method and organic electroluminescence device containing the material - Google Patents
Luminous organic material and its preparation method and organic electroluminescence device containing the material Download PDFInfo
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Abstract
The present invention relates to luminescent material technical fields, and in particular to a kind of luminous organic material and its preparation method and the organic electroluminescence device containing the material.The present invention provides a kind of luminous organic material of structure novel to solve the problems, such as that above-mentioned routine techniques exists.It realizes with excellent luminous efficiency and the organic electroluminescence device in significantly improved service life.Luminous organic material provided by the invention, the compound, which has, compared with conventional body material can show excellent Electroluminescence Properties, the device lifetime of length and appropriate chromaticity coordinates.The organic electroluminescence device of high efficiency provided by the invention and long-life, the device use luminous organic material of the present invention as electroluminescent material.The preparation method of luminous organic material provided by the invention, synthetic method is simple and easy, by the temperature and time of control reaction, can get the target product of high yield.
Description
Technical field
The present invention relates to luminescent material technical fields, and in particular to a kind of luminous organic material and its preparation method and contains the material
Organic electroluminescence device.
Background technique
The characteristics such as organic electroluminescence device has wide viewing angle, the response time is short, driving voltage is low, and can have by three kinds
Electroluminescent material (for red, green and blue) realizes full color OLED display.Important item is to develop to have
The electroluminescent material of high efficiency and long-life, to improve the overall characteristic of organic electroluminescent (EL) device.Recently, it develops high
The organic EL device of efficiency and long-life become a urgent project.It is high-purity, glass to property needed for material of main part
Change transition temperature and thermal decomposition temperature is sufficiently high, to guarantee thermal stability.In addition, material of main part should have high electrochemistry steady
It is qualitative, to provide the long-life.Amorphous phase film easy to form, and there is high adherence with other adjacent materials, but not occur
Middle layer migration.
Dinaphthyl anthracene (DNA) is widely applied blue light host compound.But the compound is applied to total colouring
When device, the service life only has thousands of hours, the reason is that excitation purity is reduced with the operating time.In blue coloured electroluminous situation, if
Electroluminescence wavelength slightly moves to more long wavelength, is advantageous in terms of luminous efficiency.But the because blue excitation purity of material
It is not high enough, therefore be difficult for material to be applied to the display of high quality.Moreover, because there are excitation purity, efficiency and thermal stability
Problem and there is an urgent need to research and develop this kind of material.
Summary of the invention
The invention solves in the prior art the technical issues of, provide a kind of luminous organic material and its preparation method and containing the material
The organic electroluminescence device of material.The present invention provides a kind of luminous organic materials of structure novel, with conventional body material phase
Excellent Electroluminescence Properties, long device lifetime and appropriate chromaticity coordinates can be shown by having than the compound.Use organic hair
Device of the luminescent material as electroluminescent material is realized with excellent luminous efficiency and the Organic Electricity in significantly improved service life
Electroluminescence device.
In order to solve the above-mentioned technical problem, technical solution of the present invention is specific as follows:
The present invention provides a kind of luminous organic material, and structural formula is as follows:
In formula:
X is oxygen；
R1To R8It each independently represents: hydrogen, halogen, C1-C60 alkyl, C6-C60 aryl, C3-C60 heteroaryl, C3-C60
Naphthenic base, three C1-C60 aIkylsilyl groups, two C1-C60 alkyl C6-C60 arylsilyl groups, three C6-C60 arylsilyls
Base, adamantyl, C2-C60 alkenyl, C2-C60 alkynyl, C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 aryl
Amino, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl；
Alternatively, R1To R8In each can be with adjacent substituent group cyclization or monocycle or polycyclic aromatic ring；
R9、R10、R12、R14And R15Each independently represent: hydrogen, halogen, C1-C60 alkyl, C6-C60 aryl, C3-C60 are miscellaneous
Aryl, heteroatomic 5- member or 6- membered heterocycloalkyl, C3-C60 naphthenic base, three C1-C60 containing one or more selected from N, O and S
AIkylsilyl groups, two C1-C60 alkyl C6-C60 arylsilyl groups, three C6-C60 arylsilyl groups, adamantyl, C7-
C60 bicyclic alkyl, C2-C60 alkenyl, C2-C60 alkynyl, C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 aryl
Amino, C6-C60 aryl C1-C60 alkyl, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitre
Base or hydroxyl；
L is indicated: chemical bond, C6-C60 arlydene or C3-C60 heteroarylidene；
Ar is indicated: C1-C60 alkyl, C6-C60 aryl, C3-C60 heteroaryl, containing one or more miscellaneous selected from N, O and S
The 5- member or 6- membered heterocycloalkyl, C3-C60 naphthenic base, three C1-C60 aIkylsilyl groups, two C1-C60 alkyl C6-C60 of atom
Arylsilyl groups, three C6-C60 arylsilyl groups, adamantyl, C7-C60 bicyclic alkyl, C2-C60 alkenyl, C2-C60 alkynes
Base, C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 arylamino, C6-C60 aryl C1-C60 alkyl, C6-
C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl.
In the above-mentioned technical solutions, the arlydene of the L or heteroarylidene are further one or more from the following
Substituent group replaces: C1-C60 alkyl, halogen, cyano, C1-C60 alkoxy, C3-C60 naphthenic base, C6-C60 aryl, C3-C60 are miscellaneous
Aryl, adamantyl, C7-C60 bicyclic alkyl, cyano, C1-C60 alkyl amino, C6-C60 arylamino, C6-C60 aryl C1-
C60 alkyl, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro, hydroxyl, three C1-C30 alkane
Base silicyl, two C1-C30 alkyl C6-C30 arylsilyl groups and three C6-C30 arylsilyl groups.
In the above-mentioned technical solutions, the luminous organic material is selected from by following below formula (2-1) to one of (5-4) table
The compound shown:
Wherein, L, Ar, R1To R8, R9、R10、R12、R14And R15According to above-mentioned definition；
R16To R18It each independently represents: hydrogen, alkyl, alkoxy, aryl, heteroaryl, Heterocyclylalkyl, naphthenic base, three alkane
Base silicyl, dialkyiarylsilyl, diarye silyl, adamantyl, bicyclic alkyl, alkenyl, alkynyl, alkyl
Amino or arylamino.Can further be replaced by substituent group selected from the following: halogen, C1-C60 alkyl, C6-C60 aryl,
C3-C60 heteroaryl, containing one or more heteroatomic 5- members selected from N, O and S or 6- membered heterocycloalkyl, C3-C60 naphthenic base,
Three C1-C60 aIkylsilyl groups, two C1-C60 alkyl C6-C60 arylsilyl groups, three C6-C60 arylsilyl groups, Buddha's warrior attendant
Alkyl, C7-C60 bicyclic alkyl, C2-C60 alkenyl, C2-C60 alkynyl, C1-C60 alkoxy, cyano, C1-C60 alkyl amino,
C6-C60 arylamino, C6-C60 aryl C1-C60 alkyl, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl
Base, carboxyl, nitro or hydroxyl.
Term " alkyl " of the present invention and " alkoxy " and any substituent group comprising " alkyl " part include straight
Chain and branching types.
In the above-mentioned technical solutions, the luminous organic material is selected from the chemical combination that following formula 1 is indicated to one of 76
Object:
The present invention also provides a kind of preparation methods of luminous organic material, comprising the following steps:
The preparation of step 1, intermediate 1
Reaction vessel is added in compound 1, N-bromosuccinimide and dichloromethane solvent, the mixing is stirred at room temperature
Water is added when the reactions are completed in object thereto, and mixture is extracted with dichloromethane, the lower filtering of extract liquor decompression, gained compound
It is recrystallized from ethyl alcohol, obtains intermediate 1；
The preparation of step 2, intermediate 2
By intermediate 1, Pd2(dba)3, connection pinacol borate and potassium acetate be dissolved in Isosorbide-5-Nitrae-dioxane, in nitrogen
In atmosphere, reactant is flowed back and is stirred to react, extracted again with methylene chloride and distilled water after reaction, then use magnesium sulfite
Dry extraction product simultaneously filters, and is then concentrated under reduced pressure filtration product, purifies enriched product by silica gel column chromatography, obtains intermediate
Body 2；
The preparation of step 3, intermediate 3
Intermediate 2, compound 2, potassium carbonate are added to toluene/ethanol/water in the mixed solvent, replaced using nitrogen empty
Three times, four (triphenyl phosphorus) palladiums are added in gas, again three times with nitrogen displaced air, react under nitrogen protection, TLC monitoring；To
After reaction, it is cooled to room temperature under nitrogen protection, carries out liquid separation using separatory funnel, retain organic phase；Use diatomite
Catalyst is removed, washes diatomite to no product with DCM；Filtrate is concentrated to a small amount of, silica gel mixed sample, is divided using silica gel funnel
From obtaining intermediate 3；
The preparation of step 4, intermediate 4
Reaction vessel is added in intermediate 3, N-bromosuccinimide and dichloromethane solvent, the mixing is stirred at room temperature
Water is added when the reactions are completed in object thereto, and mixture is extracted with dichloromethane, the lower filtering of extract liquor decompression, gained compound
It is recrystallized from ethyl alcohol, obtains intermediate 4；
The preparation of compound shown in step 5, chemical formula 1
Intermediate 4, compound 3, potassium carbonate are added to toluene/ethanol/water in the mixed solvent, replaced using nitrogen empty
Three times, four (triphenyl phosphorus) palladiums are added in gas, again three times with nitrogen displaced air, react under nitrogen protection, TLC monitoring；To
After reaction, it is cooled to room temperature under nitrogen protection；Liquid separation is carried out using separatory funnel, retains organic phase；Use diatomite
Catalyst is removed, washes diatomite to no product with DCM；Filtrate is concentrated to a small amount of, silica gel mixed sample, is divided using silica gel funnel
From obtaining compound shown in chemical formula 1；
Its synthetic route is as follows:
In the above-mentioned technical solutions, the time being stirred at room temperature in step 1 be 18-22 hours, be stirred to react in step 2 when
Between be 10-14 hour, the temperature reacted in step 3 is 80-100 DEG C, and the time being stirred to react in step 4 is 18-22 hours, is walked
The temperature reacted in rapid 5 is 80-100 DEG C.
In the above-mentioned technical solutions, the time being stirred at room temperature in step 1 is 20 hours, the time being stirred to react in step 2
It is 12 hours, the temperature reacted in step 3 is 90 DEG C, and the time being stirred to react in step 4 is 20 hours, is reacted in step 5
Temperature is 90 DEG C.
In the above-mentioned technical solutions, toluene/ethanol/water volume ratio described in step 3 and step 5 is 3:1:1.
The present invention also provides a kind of organic electroluminescence device containing above-mentioned luminous organic material, including first electrode,
Two electrodes, and at least one layer of organic layer being inserted between the first electrode and second electrode；Wherein, the organic layer includes electricity
Electroluminescent layer, the electroluminescence layer include luminous organic material shown in chemical formula 1.
In the above-mentioned technical solutions, the organic layer includes one or more compounds selected from anthracene class.
The organic layer further includes electron injecting layer, electron transfer layer, hole blocking layer, electronic barrier layer, hole transport
At least one layer in layer, hole injection layer.
The beneficial effects of the present invention are:
The present invention provides a kind of luminous organic material of structure novel to solve the problems, such as that above-mentioned routine techniques exists.It is real
Show with excellent luminous efficiency and the organic electroluminescence device in significantly improved service life.
Luminous organic material provided by the invention, the compound is excellent electroluminescent with that can show compared with conventional body material
Luminosity, the device lifetime of length and appropriate chromaticity coordinates.
The organic electroluminescence device of high efficiency provided by the invention and long-life, the device use of the present invention organic
Luminescent material is as electroluminescent material.
The preparation method of luminous organic material provided by the invention, synthetic method is simple and easy, by control reaction temperature and
Time can get the target product of high yield.
Specific embodiment
The present invention provides a kind of luminous organic material, and structural formula is as follows:
In formula: X is oxygen；R1To R8Each independently represent: hydrogen, halogen, C1-C60 alkyl, C6-C60 aryl, C3-C60 are miscellaneous
Aryl, C3-C60 naphthenic base, three C1-C60 aIkylsilyl groups, two C1-C60 alkyl C6-C60 arylsilyl groups, three C6-
C60 arylsilyl groups, adamantyl, C2-C60 alkenyl, C2-C60 alkynyl, C1-C60 alkoxy, cyano, C1-C60 alkyl ammonia
Base, C6-C60 arylamino, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl；
Alternatively, R1To R8In each can be with adjacent substituent group cyclization or monocycle or polycyclic aromatic ring；R9、R10、R12、R14And
R15Each independently represent: hydrogen, C1-C60 alkyl, C6-C60 aryl, C3-C60 heteroaryl, is selected from containing one or more halogen
N, the heteroatomic 5- member or 6- membered heterocycloalkyl, C3-C60 naphthenic base, three C1-C60 aIkylsilyl groups, two C1-C60 of O and S
Alkyl C6-C60 arylsilyl groups, three C6-C60 arylsilyl groups, adamantyl, C7-C60 bicyclic alkyl, C2-C60 alkene
Base, C2-C60 alkynyl, C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 arylamino, C6-C60 aryl C1-
C60 alkyl, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl；L is indicated: chemistry
Key, C6-C60 arlydene or C3-C60 heteroarylidene；Ar is indicated: C1-C60 alkyl, C3-C60 heteroaryl, contains C6-C60 aryl
Heteroatomic 5- member or 6- membered heterocycloalkyl, C3-C60 naphthenic base, three C1-C60 alkyl first of the one or more selected from N, O and S
Silylation, two C1-C60 alkyl C6-C60 arylsilyl groups, three C6-C60 arylsilyl groups, adamantyl, C7-C60 bis-
Naphthenic base, C2-C60 alkenyl, C2-C60 alkynyl, C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 arylamino,
C6-C60 aryl C1-C60 alkyl, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl
Base.
It is preferred that the arlydene or heteroarylidene of the L are further replaced by one or more from the following substituent group: C1-
C60 alkyl, halogen, cyano, C1-C60 alkoxy, C3-C60 naphthenic base, C6-C60 aryl, C3-C60 heteroaryl, adamantyl,
C7-C60 bicyclic alkyl, cyano, C1-C60 alkyl amino, C6-C60 arylamino, C6-C60 aryl C1-C60 alkyl, C6-C60
Aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro, hydroxyl, three C1-C30 aIkylsilyl groups, two
C1-C30 alkyl C6-C30 arylsilyl groups and three C6-C30 arylsilyl groups.
The further preferably described luminous organic material is selected from the compound indicated by one of following below formula (2-1) to (5-4):
Wherein, L, Ar, R1To R8, R9、R10、R12、R14And R15According to above-mentioned definition；
R16To R18It each independently represents: hydrogen, alkyl, alkoxy, aryl, heteroaryl, Heterocyclylalkyl, naphthenic base, three alkane
Base silicyl, dialkyiarylsilyl, diarye silyl, adamantyl, bicyclic alkyl, alkenyl, alkynyl, alkyl
Amino or arylamino.Can further be replaced by substituent group selected from the following: halogen, C1-C60 alkyl, C6-C60 aryl,
C3-C60 heteroaryl, containing one or more heteroatomic 5- members selected from N, O and S or 6- membered heterocycloalkyl, C3-C60 naphthenic base,
Three C1-C60 aIkylsilyl groups, two C1-C60 alkyl C6-C60 arylsilyl groups, three C6-C60 arylsilyl groups, Buddha's warrior attendant
Alkyl, C7-C60 bicyclic alkyl, C2-C60 alkenyl, C2-C60 alkynyl, C1-C60 alkoxy, cyano, C1-C60 alkyl amino,
C6-C60 arylamino, C6-C60 aryl C1-C60 alkyl, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl
Base, carboxyl, nitro or hydroxyl.
The most preferably described luminous organic material is selected from the compound that following formula 1 is indicated to one of 76:
The present invention also provides a kind of preparation methods of luminous organic material, comprising the following steps:
The preparation of step 1, intermediate 1
Reaction vessel is added in compound 1, N-bromosuccinimide and dichloromethane solvent, the mixing is stirred at room temperature
Water is added when the reactions are completed in object thereto, and mixture is extracted with dichloromethane, the lower filtering of extract liquor decompression, gained compound
It is recrystallized from ethyl alcohol, obtains intermediate 1；
The preparation of step 2, intermediate 2
By intermediate 1, Pd2(dba)3, connection pinacol borate and potassium acetate be dissolved in Isosorbide-5-Nitrae-dioxane, in nitrogen
In atmosphere, reactant is flowed back and is stirred to react, extracted again with methylene chloride and distilled water after reaction, then use magnesium sulfite
Dry extraction product simultaneously filters, and is then concentrated under reduced pressure filtration product, purifies enriched product by silica gel column chromatography, obtains intermediate
Body 2；
The preparation of step 3, intermediate 3
Intermediate 2, compound 2, potassium carbonate are added to toluene/ethanol/water in the mixed solvent, replaced using nitrogen empty
Three times, four (triphenyl phosphorus) palladiums are added in gas, again three times with nitrogen displaced air, react under nitrogen protection, TLC monitoring；To
After reaction, it is cooled to room temperature under nitrogen protection, carries out liquid separation using separatory funnel, retain organic phase；Use diatomite
Catalyst is removed, washes diatomite to no product with DCM；Filtrate is concentrated to a small amount of, silica gel mixed sample, is divided using silica gel funnel
From obtaining intermediate 3；
The preparation of step 4, intermediate 4
Reaction vessel is added in intermediate 3, N-bromosuccinimide and dichloromethane solvent, the mixing is stirred at room temperature
Water is added when the reactions are completed in object thereto, and mixture is extracted with dichloromethane, the lower filtering of extract liquor decompression, gained compound
It is recrystallized from ethyl alcohol, obtains intermediate 4；
The preparation of compound shown in step 5, chemical formula 1
Intermediate 4, compound 3, potassium carbonate are added to toluene/ethanol/water in the mixed solvent, replaced using nitrogen empty
Three times, four (triphenyl phosphorus) palladiums are added in gas, again three times with nitrogen displaced air, react under nitrogen protection, TLC monitoring；To
After reaction, it is cooled to room temperature under nitrogen protection；Liquid separation is carried out using separatory funnel, retains organic phase；Use diatomite
Catalyst is removed, washes diatomite to no product with DCM；Filtrate is concentrated to a small amount of, silica gel mixed sample, is divided using silica gel funnel
From obtaining compound shown in chemical formula 1；
Its synthetic route is as follows:
The time being stirred at room temperature in preferred steps 1 is 18-22 hours, and the time being stirred to react in step 2 is that 10-14 is small
When, the temperature reacted in step 3 is 80-100 DEG C, and the time being stirred to react in step 4 is 18-22 hours, is reacted in step 5
Temperature is 80-100 DEG C.The time being further preferably stirred at room temperature in step 1 is 20 hours, and the time being stirred to react in step 2 is 12
Hour, the temperature reacted in step 3 is 90 DEG C, and the time being stirred to react in step 4 is 20 hours, the temperature reacted in step 5
It is 90 DEG C.Toluene/ethanol/water volume ratio described in preferred steps 3 and step 5 is 3:1:1.
The present invention also provides a kind of organic electroluminescence device containing above-mentioned luminous organic material, including first electrode,
Two electrodes, and at least one layer of organic layer being inserted between the first electrode and second electrode；Wherein, the organic layer includes electricity
Electroluminescent layer, the electroluminescence layer include luminous organic material shown in chemical formula 1.It is preferred that the organic layer include it is a kind of or
A variety of compounds selected from anthracene class.It is preferred that the organic layer further includes electron injecting layer, electron transfer layer, hole blocking layer, electricity
Sub- barrier layer, hole transmission layer, at least one layer in hole injection layer.
The preparation embodiment of luminous organic material shown in chemical formula 1
The preparation of [preparation example 1] compound 1
The preparation of compound A-1
By 2,3- dibromoanthracene (15.0g 44.64mmol), phenyl boric acid (13.6g 111.6mmol), potassium carbonate (30.8g
223.2mmol) it is added to 500mL toluene/ethanol/water (volume ratio 3:1:1) in the mixed solvent.Use nitrogen displaced air three
It is secondary, four (triphenyl phosphorus) palladiums (2.58g 0.22mmol) are added, again three times with nitrogen displaced air, heat under nitrogen protection
To 90 DEG C.TLC monitoring.To after reaction, be cooled to room temperature under nitrogen protection.Liquid separation is carried out using separatory funnel, is retained
Organic phase.Catalyst is removed using diatomite, washes diatomite to no product with DCM.Filtrate is concentrated to a small amount of, silica gel mixed sample makes
It is separated with silica gel funnel, obtains intermediate A -1 (12.8g, yield=87%).
The preparation of compound B-1
By compound A-1 (12.8g 38.73mmol), N-bromosuccinimide (NBS) (6.89g 38.73mmol) and
Reaction vessel is added in dichloromethane solvent (250mL), the mixture is stirred at room temperature 20 hours.When the reactions are completed, thereto
It is added water (100mL milliliters), mixture is extracted with (300 milliliters) of methylene chloride.The lower filtering of extract liquor decompression, gained compound from
(500 milliliters) recrystallizations in ethyl alcohol, obtain target compound B-1 (14.27g yield=90%).
The preparation of compound C-1
By compound B-1 (14.0g 34.2mmol), Pd2(dba)3(0.31g 0.342mmol), connection pinacol borate
(13.0g 51.3mmol) and potassium acetate (10.0g 102.6mmol) are dissolved in the dry 1,4- dioxane of 300mL.In nitrogen
In gas atmosphere, reactant is flowed back and is stirred 12 hours, then extracted 3 times with methylene chloride and distilled water.It is dry with magnesium sulfite
Extraction product simultaneously filters, and is then concentrated under reduced pressure filtration product.Enriched product is purified by silica gel column chromatography, obtains compound C-
1 (12.96g yield=83%).
The preparation of compound D-1
Compound C-1 (28.26mmol), compound 1-1 (33.92mmol), potassium carbonate (84.76mmol) are added to
500mL toluene/ethanol/water (volume ratio 3:1:1) in the mixed solvent.Three times using nitrogen displaced air, four (triphenyls are added
Phosphorus) palladium (0.28mmol), it uses nitrogen displaced air three times again, is heated to 90 DEG C under nitrogen protection.TLC monitoring.Wait react
After, it is cooled to room temperature under nitrogen protection.Liquid separation is carried out using separatory funnel, retains organic phase.It is removed using diatomite
Catalyst washes diatomite to no product with DCM.Filtrate is concentrated to a small amount of, silica gel mixed sample, is separated, is obtained using silica gel funnel
To compound D-1 (12.27g yield=86%).
The preparation of compound E-1
By compound D-1 (23.5mmol), N-bromosuccinimide (NBS) (35.25mmol) and dichloromethane solvent
Reaction vessel is added in (300mL), the mixture is stirred at room temperature 20 hours.When the reactions are completed, water is added thereto
(100mL), mixture are extracted with methylene chloride (200mL).The lower filtering of extract liquor decompression, gained compound is from ethyl alcohol (300mL)
Middle recrystallization obtains compound E-1 (12.05 yield=87%).
The preparation of compound 1
Compound E-1 (20.36mmol), 2- naphthalene boronic acids (24.43mmol), potassium carbonate (61.08mmol) are added to
500mL toluene/ethanol/water (volume ratio 3:1:1) in the mixed solvent.Three times using nitrogen displaced air, four (triphenyls are added
Phosphorus) palladium (0.2mmol), it uses nitrogen displaced air three times again, is heated to 90 DEG C under nitrogen protection.TLC monitoring.Wait react knot
Shu Hou is cooled to room temperature under nitrogen protection.Liquid separation is carried out using separatory funnel, retains organic phase.It is urged using diatomite removing
Agent washes diatomite to no product with DCM.Filtrate is concentrated to a small amount of, silica gel mixed sample, is separated, is obtained using silica gel funnel
Compound 1 (10.54g yield=80%), mass spectrometry value 623.25.
The preparation of [preparation example 2] compound 18
It, will in the way of preparation example 1It replaces withIt willIt replaces with
It willIt replaces withPrepare compound 18, mass spectrometry value 955.40.
The preparation of [preparation example 3] compound 19
It, will in the way of preparation example 18It replaces withPrepare compound 19, matter
Spectrum is 955.71.
The preparation of [preparation example 4] compound 20
It, will in the way of preparation example 18It replaces withPrepare compound 20, mass spectrum
Value is 956.24.
The preparation of [preparation example 5] compound 21
Except by its raw material 2,3- dibromoanthracene is replaced with outside 2- bromine anthracene, other steps are identical as preparing for compound 1, can be obtained
Compound 21, mass spectrometry value 549.69.
The preparation of [preparation example 6] compound 44
According to the preparation method of compound 19, by its raw material 2,3- dibromoanthracene replaces with 2- bromine anthracene, prepare compound 44, matter
Spectrum is 715.92.
The preparation of [preparation example 7] compound 45
It, will according to the preparation method of compound 44It replaces withPrepare compound 45,
Mass spectrometry value is 715.93.
The preparation of [preparation example 8] compound 47
According to the preparation method of compound 20,2,3- dibromoanthracene is replaced with into 2- bromine anthracene, prepare compound 47, mass spectrometry value is
715.91。
The preparation of [preparation example 9] compound 56
It, will according to the preparation method of compound 21It replaces withIt willReplacement
ForPrepare compound 56, mass spectrometry value 599.80.
The preparation of [preparation example 10] compound 72
It, will according to the preparation method of compound 56It replaces withIt willIt replaces withPrepare compound 72, mass spectrometry value 715.92.
The preparation of [preparation example 11] compound 73
It, will according to the preparation method of compound 72It replaces withPrepare compound 73,
Mass spectrometry value is 715.33.
The preparation of [preparation example 12] compound 75
It, will according to the preparation method of compound 72It replaces withPrepare compound 75, matter
Spectrum is 715.92.
OLED device is manufactured using the compound of the present invention.
[embodiment 1]
It is by Fisher Co., Ltd's coating layer thicknessIto glass substrate be placed in distilled water and clean 2 times, ultrasonic wave
Washing 30 minutes, cleaned repeatedly with distilled water 2 times, ultrasonic washing 10 minutes, distilled water clean after, isopropanol, acetone,
Ultrasonic washing is later dry in order for methanol equal solvent, is transferred in plasma washing machine, and aforesaid substrate is washed 5 points
Clock is sent in evaporator.The 4,4' for being 50nm by evaporation thickness on the ito transparent electrode having had been prepared for, 4 "-three [2- naphthalenes
Phenyl amino] triphenylamine (2-TNATA) be used as hole injection layer.On the hole injection layer of formation vacuum evaporation with a thickness of
N'- bis- (1- naphthalene)-N of 30nm, N'- diphenyl-(1,1'- biphenyl) -4,4'- diamines (NPB) are used as hole transmission layer.Then
The compound of the present invention 1 that evaporation thickness is 30nm on above-mentioned hole transmission layer is used as material of main part and dopant material 4,4'-
Bis- [4- (di-p-tolyl amino) styryl] biphenyl (DPAVBi).The weight ratio of material of main part and dopant material is 97:3.
Then on above-mentioned luminescent layer vacuum evaporation with a thickness of 10nm bis- (2- methyl -8-hydroxyquinoline-N1,08)-(1,1 '-biphenyl -
4- hydroxyl) aluminium (BAlq) be used as hole blocking layer.On above-mentioned hole blocking layer vacuum evaporation with a thickness of 40nm three (8- hydroxyls
Quinoline) aluminium (III) Alq3 is as electron transfer layer.Vacuum evaporation is on above-mentioned electron transfer layer with a thickness of 0.5nm lithium fluoride
(LiF), as electron injecting layer.The aluminium that last evaporation thickness is 150nm completes organic electroluminescence as cathode with this
The preparation of part.
[embodiment 2]
Other than replacing compound 1 with compound 18, organic electroluminescence is prepared with method same as Example 1
Part.
[embodiment 3]
Other than replacing compound 1 with compound 19, organic electroluminescence is prepared with method same as Example 1
Part.
[embodiment 4]
Other than replacing compound 1 with compound 20, organic electroluminescence is prepared with method same as Example 1
Part.
[embodiment 5]
Other than replacing compound 1 with compound 21, organic electroluminescence is prepared with method same as Example 1
Part.
[embodiment 6]
Other than replacing compound 1 with compound 44, organic electroluminescence is prepared with method same as Example 1
Part.
[embodiment 7]
Other than replacing compound 1 with compound 45, organic electroluminescence is prepared with method same as Example 1
Part.
[embodiment 8]
Other than replacing compound 1 with compound 47, organic electroluminescence is prepared with method same as Example 1
Part.
[embodiment 9]
Other than replacing compound 1 with compound 56, organic electroluminescence is prepared with method same as Example 1
Part.
[embodiment 10]
Other than replacing compound 1 with compound 72, organic electroluminescence is prepared with method same as Example 1
Part.
[embodiment 11]
Other than replacing compound 1 with compound 73, organic electroluminescence is prepared with method same as Example 1
Part.
[embodiment 12]
Other than replacing compound 1 with compound 75, organic electroluminescence is prepared with method same as Example 1
Part.
[comparative example 1]
In addition to compound 9,10- is bis--(1- naphthalene) anthracene (ADN) replaces other than compound 1, with same as Example 1
Method prepares organic electroluminescence device.
The Electroluminescence Properties of the OLED of above-described embodiment manufacture.
Efficiency (the electricity for each organic electroluminescence device that evaluation is manufactured according to embodiment 1 to embodiment 12 and comparative example 1
Current density: 10mA/cm2) and service life (10mA/cm2T90 under current density).
Therefore, the compound of the present invention may be used as efficient blue electroluminescent material.In addition, applied the present invention
Compound make the device of material of main part and show significant improvement in terms of excitation purity.At two aspects of service life and luminous efficiency
Improving confirms that material of the invention has excellent property.
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, structural formula is as follows:
In formula:
X is oxygen；
R1To R8It each independently represents: hydrogen, halogen, C1-C60 alkyl, C6-C60 aryl, C3-C60 heteroaryl, C3-C60 cycloalkanes
Base, three C1-C60 aIkylsilyl groups, two C1-C60 alkyl C6-C60 arylsilyl groups, three C6-C60 arylsilyl groups,
Adamantyl, C2-C60 alkenyl, C2-C60 alkynyl, C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 aryl ammonia
Base, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl；
Alternatively, R1To R8In each can be with adjacent substituent group cyclization or monocycle or polycyclic aromatic ring；
R9、R10、R12、R14And R15It each independently represents: hydrogen, halogen, C1-C60 alkyl, C6-C60 aryl, C3-C60 heteroaryl
Base, heteroatomic 5- member or 6- membered heterocycloalkyl, C3-C60 naphthenic base, three C1-C60 alkane containing one or more selected from N, O and S
Base silicyl, two C1-C60 alkyl C6-C60 arylsilyl groups, three C6-C60 arylsilyl groups, adamantyl, C7-
C60 bicyclic alkyl, C2-C60 alkenyl, C2-C60 alkynyl, C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 aryl
Amino, C6-C60 aryl C1-C60 alkyl, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitre
Base or hydroxyl；
L is indicated: chemical bond, C6-C60 arlydene or C3-C60 heteroarylidene；
Ar is indicated: C1-C60 alkyl, C6-C60 aryl, C3-C60 heteroaryl, the hetero atoms containing one or more selected from N, O and S
5- member or 6- membered heterocycloalkyl, C3-C60 naphthenic base, three C1-C60 aIkylsilyl groups, two C1-C60 alkyl C6-C60 aryl
Silicyl, three C6-C60 arylsilyl groups, adamantyl, C7-C60 bicyclic alkyl, C2-C60 alkenyl, C2-C60 alkynyl,
C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 arylamino, C6-C60 aryl C1-C60 alkyl, C6-C60 virtue
Oxygroup, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl.
2. luminous organic material according to claim 1, which is characterized in that the arlydene or heteroarylidene of the L is into one
Step is replaced by one or more from the following substituent group: C1-C60 alkyl, halogen, cyano, C1-C60 alkoxy, C3-C60 ring
Alkyl, C6-C60 aryl, C3-C60 heteroaryl, adamantyl, C7-C60 bicyclic alkyl, cyano, C1-C60 alkyl amino, C6-
C60 arylamino, C6-C60 aryl C1-C60 alkyl, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl,
Carboxyl, nitro, hydroxyl, three C1-C30 aIkylsilyl groups, two C1-C30 alkyl C6-C30 arylsilyl groups and three C6-C30
Arylsilyl groups.
3. luminous organic material according to claim 1, which is characterized in that it is selected from by following below formula (2-1) to (5-
One of 4) compound indicated:
R16To R18It each independently represents: hydrogen, alkyl, alkoxy, aryl, heteroaryl, Heterocyclylalkyl, naphthenic base, trialkyl first
Silylation, dialkyiarylsilyl, diarye silyl, adamantyl, bicyclic alkyl, alkenyl, alkynyl, alkyl amino
Or arylamino.
4. luminous organic material according to claim 1, which is characterized in that it is selected from following formula 1 to one of 76
The compound of expression:
5. a kind of preparation method of luminous organic material described in claim 1-4 any one, which is characterized in that including following step
It is rapid:
The preparation of step 1, intermediate 1
Reaction vessel is added in compound 1, N-bromosuccinimide and dichloromethane solvent, the mixture is stirred at room temperature,
When the reactions are completed, water is added thereto, mixture is extracted with dichloromethane, the lower filtering of extract liquor decompression, gained compound from
It is recrystallized in ethyl alcohol, obtains intermediate 1；
The preparation of step 2, intermediate 2
By intermediate 1, Pd2(dba)3, connection pinacol borate and potassium acetate be dissolved in Isosorbide-5-Nitrae-dioxane, in nitrogen atmosphere
In, reactant is flowed back and is stirred to react, is extracted again with methylene chloride and distilled water after reaction, then is dry with magnesium sulfite
Extraction product simultaneously filters, and is then concentrated under reduced pressure filtration product, purifies enriched product by silica gel column chromatography, obtains intermediate 2；
The preparation of step 3, intermediate 3
Intermediate 2, compound 2, potassium carbonate are added to toluene/ethanol/water in the mixed solvent, use nitrogen displaced air three
It is secondary, four (triphenyl phosphorus) palladiums are added, again three times with nitrogen displaced air, react under nitrogen protection, TLC monitoring；Wait react
After, it is cooled to room temperature under nitrogen protection, carries out liquid separation using separatory funnel, retain organic phase；It is removed using diatomite
Catalyst washes diatomite to no product with DCM；Filtrate is concentrated to a small amount of, silica gel mixed sample, is separated, is obtained using silica gel funnel
To intermediate 3；
The preparation of step 4, intermediate 4
Reaction vessel is added in intermediate 3, N-bromosuccinimide and dichloromethane solvent, the mixture is stirred at room temperature,
When the reactions are completed, water is added thereto, mixture is extracted with dichloromethane, the lower filtering of extract liquor decompression, gained compound from
It is recrystallized in ethyl alcohol, obtains intermediate 4；
The preparation of compound shown in step 5, chemical formula 1
Intermediate 4, compound 3, potassium carbonate are added to toluene/ethanol/water in the mixed solvent, use nitrogen displaced air three
It is secondary, four (triphenyl phosphorus) palladiums are added, again three times with nitrogen displaced air, react under nitrogen protection, TLC monitoring；Wait react
After, it is cooled to room temperature under nitrogen protection；Liquid separation is carried out using separatory funnel, retains organic phase；It is removed using diatomite
Catalyst washes diatomite to no product with DCM；Filtrate is concentrated to a small amount of, silica gel mixed sample, is separated, is obtained using silica gel funnel
To compound shown in chemical formula 1；
Its synthetic route is as follows:
6. the preparation method of luminous organic material according to claim 5, which is characterized in that the time being stirred at room temperature in step 1
It is 18-22 hours, the time being stirred to react in step 2 is 10-14 hours, and the temperature reacted in step 3 is 80-100 DEG C, step
The time being stirred to react in 4 is 18-22 hours, and the temperature reacted in step 5 is 80-100 DEG C.
7. the preparation method of luminous organic material according to claim 5, which is characterized in that the time being stirred at room temperature in step 1
It is 20 hours, the time being stirred to react in step 2 is 12 hours, and the temperature reacted in step 3 is 90 DEG C, is stirred in step 4 anti-
The time answered is 20 hours, and the temperature reacted in step 5 is 90 DEG C.
8. the preparation method of luminous organic material according to claim 5, which is characterized in that first described in step 3 and step 5
Benzene/ethanol/water volume ratio is 3:1:1.
9. a kind of organic electroluminescence device of luminous organic material described in any one of 1-4 containing claim, including first
Electrode, second electrode, and at least one layer of organic layer being inserted between the first electrode and second electrode；Wherein, described organic
Layer includes electroluminescence layer, which is characterized in that the electroluminescence layer includes luminous organic material shown in chemical formula 1.
10. organic electroluminescence device according to claim 9, which is characterized in that the organic layer includes a kind of or more
Kind is selected from the compound of anthracene class.
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