CN110483500A - A kind of OLED material of main part and preparation method thereof and OLED device - Google Patents
A kind of OLED material of main part and preparation method thereof and OLED device Download PDFInfo
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
Abstract
The invention discloses a kind of OLED material of main part and preparation method thereof and OLED device.The mechanism type of the OLED material of main part is shown in formula I:In Formulas I, R1、R4For C1‑C20Alkyl, phenyl, 4- aminomethyl phenyl, 4- methoxyphenyl, one of furans -2- base, R2、R3For one of phenyl, naphthalene, furans, thiophene, benzofuran, benzo thiophene phenol, R5、R6、R7、R8For C1‑C20Alkyl, methoxyl group, one of phenyl.OLED material of main part of the present invention is a kind of material of main part with small organic molecule luminescent material with more preferable compatibility, thus the unstable problem of device caused by avoiding doped system from mutually separating, and alleviate efficiency roll-off to improve its device lifetime.
Description
Technical field
The present invention relates to organic photoelectric fields more particularly to a kind of OLED material of main part and preparation method thereof and OLED device
Part.
Background technique
Organic electroluminescence device (OLED) is low with its driving voltage, energy consumption is small, frivolous, face shines and foldable rollable
Etc. unique advantages, become the outstanding person of next-generation full-color display and solid-state lighting.Therefore OLED has huge application prospect
With potential economic benefit.But OLED still has deficiency.OLED asking there is device stability deviation in the prior art
Topic, small organic molecule luminescent material the excitation purity in terms of feux rouges and blue light and in terms of the OLED service life it is undesirable.
Therefore, the existing technology needs to be improved and developed.
Summary of the invention
In view of above-mentioned deficiencies of the prior art, the purpose of the present invention is to provide a kind of OLED material of main part and its preparation sides
Method and OLED device, it is intended to which solving existing OLED, there is device stability deviations, and small organic molecule luminescent material is in excitation purity
The problem of with being also lacking in terms of the service life.
A kind of OLED material of main part, wherein the structural formula of the OLED material of main part is shown in formula I:
In Formulas I, R1、R4It independently is C1-C20Alkyl, phenyl, 4- aminomethyl phenyl, 4- methoxyphenyl, furans -2- base
One of, R2、R3It independently is one of phenyl, naphthalene, furans, thiophene, benzofuran, benzo thiophene phenol, R5、R6、R7、R8
It independently is C1-C20Alkyl, methoxyl group, one of phenyl.
A kind of preparation method of OLED material of main part as described above, wherein comprising steps of
Propylene ketone compound shown in the compound of neighbour's aminopheny-lacetonitrile shown in Formula II, formula III is mixed with alcohols solvent, is carried out
Heating reaction obtains the first crude product, will obtain benzazolyl compounds shown in formula IV after the first crude product separating-purifying；
Formula II, formula III, in formula IV, R5、R6、R7、R8It independently is C1-C20Alkyl, methoxyl group, one of phenyl,
R1、R4It independently is C1-C20Alkyl, phenyl, 4- aminomethyl phenyl, 4- methoxyphenyl, one of furans -2- base；
After boronic acid compounds shown in 2,4,6- tri- chloro-1,3,5-triazines, Formula V, toluene are mixed, under atmosphere of inert gases
It is reacted to obtain the second crude product, triaizine compounds shown in Formula IV will be obtained after the second crude product separating-purifying；
R is one of phenyl, naphthalene, furans, thiophene, benzofuran, benzo thiophene phenol or a variety of, R in Formula IV in Formula V2、
R3It independently is one of phenyl, naphthalene, furans, thiophene, benzofuran, benzo thiophene phenol；
Benzazolyl compounds shown in the formula IV are dissolved in n,N-Dimethylformamide, NaH is added and stirs to get yellow
Solution is added triaizine compounds shown in the Formula IV in Xiang Suoshu yellow solution and is reacted to obtain third crude product, will be described
OLED material of main part is obtained after third crude product separating-purifying.
The preparation method of the OLED material of main part, wherein alcohols solvent is dehydrated alcohol.
The preparation method of the OLED material of main part, wherein it is described carry out heating reaction obtain the first crude product before,
It further include that p-methyl benzenesulfonic acid is added.
The preparation method of the OLED material of main part, wherein described to be reacted to obtain under atmosphere of inert gases
It further include that solution of potassium carbonate, 4-propyl bromide, palladium reagent is added before two crude products.
The preparation method of the OLED material of main part, wherein described to be obtained after the first crude product separating-purifying
Benzazolyl compounds shown in formula IV specifically include:
Resulting first crude product ester soluble solvent and water extraction are reacted into heating, retains organic phase, is chromatographed by column
Separation, then uses methylene chloride to be recrystallized to give benzazolyl compounds shown in formula IV as poor solvent as good solvent petroleum ether.
The preparation method of the OLED material of main part, wherein described to be obtained after the second crude product separating-purifying
Triaizine compounds shown in Formula IV specifically include:
Second crude product is put into purifying furnace, sublimation purification obtains triaizine compounds shown in Formula IV.
The preparation method of the OLED material of main part, wherein described to be obtained after the third crude product separating-purifying
OLED material of main part specifically includes:
By the third crude product with water quench, then filter, by the sediment obtained after filtering use respectively water, ethyl alcohol,
Then methanol washing, drying obtain OLED material of main part with re crystallization from toluene.
The preparation method of the OLED material of main part, wherein described 2,4,6- tri- chloro-1,3,5-triazines and the Formula V
The ratio between amount of substance of shown boronic acid compounds is 1:2.5.
A kind of OLED device, wherein the OLED device includes OLED material of main part as described above.
The utility model has the advantages that OLED material of main part of the present invention be it is a kind of have with small organic molecule luminescent material it is more preferably compatible
Property material of main part, thus the unstable problem of device caused by avoiding doped system from mutually separating, and alleviate efficiency roll-off with
Improve its device lifetime.
Detailed description of the invention
Fig. 1 is the reacting flow chart that the embodiment of the present invention 1 synthesizes OLED material of main part.
Fig. 2 is the hydrogen spectrogram for the OLED material of main part that the embodiment of the present invention 1 is prepared.
Specific embodiment
The present invention provides a kind of OLED material of main part and preparation method thereof and OLED device, to make the purpose of the present invention, skill
Art scheme and effect are clearer, clear, and the present invention is described in more detail below.It should be appreciated that tool described herein
Body embodiment is only used to explain the present invention, is not intended to limit the present invention.
The present invention provides a kind of OLED material of main part, wherein the structural formula of the OLED material of main part is shown in formula I:
In Formulas I, R1、R4It independently is C1-C20Alkyl, phenyl, 4- aminomethyl phenyl, 4- methoxyphenyl, furans -2- base
One of, R2、R3It independently is one of phenyl, naphthalene, furans, thiophene, benzofuran, benzo thiophene phenol, R5、R6、R7、R8
It independently is C1-C20Alkyl, methoxyl group, one of phenyl.
OLED material of main part of the present invention is a kind of novel OLED material of main part based on triazine, is particularly suitable for OLED
The material of main part of red light material.Driving electricity can be effectively reduced due to having very big conjugation mechanism in the OLED material of main part
Efficiency roll-off is pressed and alleviates, to improve the service life of feux rouges OLED device.The OLED material of main part and small organic molecule are sent out
The compatibility of luminescent material is good, and doped system is avoided mutually to separate the unstable of caused device.
Preferably, OLED material of main part of the present invention is 2- phenyl -9- (1,3,5-triazines -2- base) -9H- pyrido
[2,3-b] indoles, wherein groups such as benzene, furans etc. are connected on the 4 of triazine, 6 No. 4 positions with pyrido [2,3-b] indoles
Other functional groups.It is highly preferred that the OLED material of main part is 9- (4,6- diphenyl -1,3,5-triazines -2- base) -2,4- hexichol
Base -9H- pyrido [2,3-b] indoles, structural formula is as shown in Formula VII.Above-mentioned preferred OLED material of main part can be further
Driving voltage is reduced, the service life of feux rouges OLED device is greatly improved.
The present invention also provides a kind of preparation methods of OLED material of main part as described above, wherein comprising steps of
A, benzazolyl compounds shown in preparation formula IV
Propylene ketone compound shown in the compound of neighbour's aminopheny-lacetonitrile shown in Formula II, formula III is mixed with alcohols solvent, is carried out
Heating reaction obtains the first crude product, will obtain benzazolyl compounds shown in formula IV after the first crude product separating-purifying；
Formula II, formula III, in formula IV, R5、R6、R7、R8It independently is C1-C20Alkyl, methoxyl group, one of phenyl,
R1、R4It independently is C1-C20Alkyl, phenyl, 4- aminomethyl phenyl, 4- methoxyphenyl, one of furans -2- base；
Neighbour's aminopheny-lacetonitrile compound shown in the Formula II is reacted with propylene ketone compound shown in the formula III described in generation
The chemical equation of benzazolyl compounds shown in formula IV:
Preferably, the alcohols solvent is dehydrated alcohol (EtOH).Neighbour's aminopheny-lacetonitrile compound and institute shown in the II
State propylene ketone compound shown in formula III has good dissolubility in alcohols solvent, and dehydrated alcohol more holds in alcohols solvent
It easily obtains, cost is relatively low.
Preferably, it is described carry out heating reaction obtain the first crude product before, further include be added p-methyl benzenesulfonic acid.The present invention
The p-methyl benzenesulfonic acid is used as the catalyst of benzazolyl compounds shown in preparation formula IV.P-methyl benzenesulfonic acid is one and does not have oxidisability
Organic acid, acidity are 1,000,000 times of benzoic acid, suitable for neighbour's aminopheny-lacetonitrile compound shown in the Formula II with it is described
Propylene ketone compound shown in formula III reacts the catalyst of benzazolyl compounds shown in production IV.
Specifically, by dehydrated alcohol, propenone shown in neighbour's aminopheny-lacetonitrile compound shown in the Formula II and the formula III
Compound mixing, adds catalyst p-methyl benzenesulfonic acid, is heated to 80 DEG C and flows back 4 hours, TLC tracks raw material, until raw material point
It disappears, fully reacting is cooled to room temperature to obtain the first crude product, will obtain shown in formula IV after the first crude product separating-purifying
Benzazolyl compounds.
Preferably, described to be obtained after the first crude product separating-purifying during benzazolyl compounds shown in preparation formula IV
It is specifically included to benzazolyl compounds shown in formula IV:
Resulting first crude product ester soluble solvent and water extraction are reacted into heating, retains organic phase, is chromatographed by column
Separation, then uses methylene chloride to be recrystallized to give benzazolyl compounds shown in formula IV as poor solvent as good solvent petroleum ether.
Benzazolyl compounds shown in formula IV of the present invention are a kind of ester soluble substances, can remove being dissolved in product by the method for extraction
The impurity of water obtains indoles chemical combination shown in the formula IV of high-purity then through column chromatography for separation and the method for recrystallization
Object.Preferably, the fat-soluble solvent is carbon tetrachloride.
B, triaizine compounds shown in preparation formula VI
By 2,4,6- tri- chloro-1,3,5-triazines, after boronic acid compounds shown in Formula V, toluene mix, under atmosphere of inert gases
It is reacted to obtain the second crude product, triaizine compounds shown in Formula IV will be obtained after the second crude product separating-purifying；
R is one of phenyl, naphthalene, furans, thiophene, benzofuran, benzo thiophene phenol or a variety of, R in Formula IV in Formula V2、
R3It independently is one of phenyl, naphthalene, furans, thiophene, benzofuran, benzo thiophene phenol.
The chemical equation of triaizine compounds shown in preparation formula VI of the present invention:
In the present invention, the R in boronic acid compounds shown in Formula V replaces two chlorine originals on 2,4,6- tri- chloro-1,3,5-triazines
Son, thus triaizine compounds shown in preparation formula VI.
Preferably, it is described reacted to obtain the second crude product under atmosphere of inert gases before, further include be added carbonic acid
Potassium solution, 4-propyl bromide, palladium reagent.Wherein palladium reagent can be 0 valence palladium reagent, be used as catalysis during the reaction.It is logical
Often, 4-propyl bromide is that the good release phase of sun switchs to catalyst, petrochemical industry, catalyst preparation.The inert gas is
Nitrogen.Specifically, it is described be added solution of potassium carbonate, 4-propyl bromide, palladium reagent process be logical inert gas 15min after plus
Enter solution of potassium carbonate and 4-propyl bromide, then logical inert gas, is subsequently added into 0 valence palladium reagent of catalyst.
Preferably, described to obtain triaizine compounds shown in Formula IV after the second crude product separating-purifying and specifically include:
Second crude product is put into purifying furnace, sublimation purification obtains triaizine compounds shown in Formula IV.Triazine shown in Formula IV
Compound has typical triazine structure, can be purified by the method for distillation.
C, OLED material of main part is prepared
The general structure of the OLED material of main part is shown in formula I.
Benzazolyl compounds shown in the formula IV are dissolved in n,N-Dimethylformamide (DMF), NaH is added and stirs to get
Yellow solution is added triaizine compounds shown in the Formula IV in Xiang Suoshu yellow solution and is reacted to obtain third crude product, will
OLED material of main part is obtained after the third crude product separating-purifying.
The specific reaction equation of OLED material of main part:
The preparation method of the OLED material of main part is also based on the preparation method of substitution reaction.
Preferably, triaizine compounds shown in the Formula IV are added in the yellow solution to be reacted to obtain third crude product
Reaction temperature be room temperature (rt), such as 20-38 DEG C.
Preferably, it is specifically to be vigorously stirred lower addition NaH in room temperature that the addition NaH, which stirs to get yellow solution, is obtained
Yellow solution, once and H2 stops evolution during this, just solution is stirred one hour.
Preferably, described to obtain OLED material of main part after the third crude product separating-purifying and specifically include:
Third crude product with water is quenched, is then filtered, the sediment obtained after filtering is used into water, ethyl alcohol, methanol respectively
Washing, drying, then obtains OLED material of main part with re crystallization from toluene.
Wherein, described that the quenching of third crude product with water is removed into excessive NaH, then successively water, ethyl alcohol, methanol wash into
Row removal of impurities, first progress water washing carries out ethyl alcohol again, methanol washing removes remaining water in solid, is conducive to drying.
A kind of OLED device, wherein the OLED device includes OLED material of main part as described above.Specifically, described
The luminescent layer of OLED device is collectively formed in OLED material of main part and luminous organic material.By by the OLED material of main part with have
The method of machine luminescent material doping, can be improved the stability of photoluminescence of OLED device, to improve the service life of OLED device.
Technical solution of the present invention is illustrated below by specific embodiment.
Embodiment 1
15ml alcohols solvent, -2 propylene -1- ketone of 1,3- diphenyl are separately added into the round bottom single-necked flask of 50ml
(1.05mmol, 0.22g), adjacent aminopheny-lacetonitrile (1mmol, 0.15g), catalyst p-methyl benzenesulfonic acid (0.1mmo, 0.17g) add
Heat flows back 4 hours to 80 DEG C, and TLC tracks raw material, and until raw material point disappears, fully reacting is cooled to room temperature.By gained mixture
It is extracted with carbon tetrachloride and water, retains organic phase, crude product is obtained by column chromatography for separation, then use methylene chloride as good molten
Agent petroleum ether is recrystallized to give 2,4- diphenyl -9H- pyrido [2,3-b] indoles white solid 0.135g as poor solvent.
It is added 2,4,6- tri- chloro-1,3,5-triazines (10mmol, 3g) in the single port bottle of 150ml, phenyl boric acid (25mmol,
2.5g), 10ml solution of potassium carbonate (2mol/L) and 4-propyl bromide (1g) is added after leading to inert gas 15min in 50ml toluene,
Lead to 15min nitrogen again, be subsequently added into 0 valence palladium reagent (mass percent 5%) of catalyst, flow back 10 hours, after cooling, is spin-dried for,
It is dry, it is then placed in purifying furnace, sublimation purification obtains chloro- 4, the 6- diphenyl -1,3,5-triazines of white needle-like crystals 2-
0.78g。
2,4- diphenyl -9H- pyrido [2,3-b] indoles (1.25mmol, 0.4g) is added in 50ml round-bottomed flask, so
It is dissolved afterwards with 17ml anhydrous DMF, is then vigorously stirred lower addition NaH (1.87mmol, 0.04g) in room temperature, obtains yellow solution,
Once H2 stop evolution, just by solution stir one hour, then use chloro- 4, the 6- diphenyl -1,3,5-triazines of 2- (1.87mmol,
It 0.5g) handles, and stays in and be stirred to react at room temperature 10 hours.Crude product with water is quenched, is then filtered, by white depositions
It is washed respectively with water, ethyl alcohol, methanol, dries, then obtain purer white solid 9- (4,6- hexichol twice with re crystallization from toluene
Base -1,3,5- triazine -2- base) -2,4- diphenyl -9H- pyrido [2,3-b] indoles (OLED material of main part) 0.26g.
Fig. 1 is that the present embodiment prepares 9- (4,6- diphenyl -1,3,5- triazine -2- base) -2,4- diphenyl -9H- pyrido
The synthetic schemes of [2,3-b] indoles.Fig. 2 is 9- (4,6- diphenyl -1,3,5- triazine -2- base) -2 prepared by the present embodiment,
The hydrogen spectrogram of 4- diphenyl -9H- pyrido [2,3-b] indoles.From Fig. 2, show that 9- (4,6- is successfully prepared in the present embodiment
Diphenyl -1,3,5- triazine -2- base) -2,4- diphenyl -9H- pyrido [2,3-b] indoles.
It should be understood that the application of the present invention is not limited to the above for those of ordinary skills can
With improvement or transformation based on the above description, all these modifications and variations all should belong to the guarantor of appended claims of the present invention
Protect range.
Claims (10)
1. a kind of OLED material of main part, which is characterized in that the structural formula of the OLED material of main part is shown in formula I:
In Formulas I, R1、R4It independently is C1-C20Alkyl, phenyl, 4- aminomethyl phenyl, 4- methoxyphenyl, in furans -2- base
One kind, R2、R3It independently is one of phenyl, naphthalene, furans, thiophene, benzofuran, benzo thiophene phenol, R5、R6、R7、R8It is independent
Ground is C1-C20Alkyl, methoxyl group, one of phenyl.
2. a kind of preparation method of OLED material of main part as described in claim 1, which is characterized in that comprising steps of
Propylene ketone compound shown in the compound of neighbour's aminopheny-lacetonitrile shown in Formula II, formula III is mixed with alcohols solvent, is heated
Reaction obtains the first crude product, will obtain benzazolyl compounds shown in formula IV after the first crude product separating-purifying；
Formula II, formula III, in formula IV, R5、R6、R7、R8It independently is C1-C20Alkyl, methoxyl group, one of phenyl, R1、R4
It independently is C1-C20Alkyl, phenyl, 4- aminomethyl phenyl, 4- methoxyphenyl, one of furans -2- base；
After boronic acid compounds shown in 2,4,6- tri- chloro-1,3,5-triazines, Formula V, toluene are mixed, carried out under atmosphere of inert gases
Reaction obtains the second crude product, will obtain triaizine compounds shown in Formula IV after the second crude product separating-purifying；
R is one of phenyl, naphthalene, furans, thiophene, benzofuran, benzo thiophene phenol or a variety of, R in Formula IV in Formula V2、R3Solely
It is on the spot one of phenyl, naphthalene, furans, thiophene, benzofuran, benzo thiophene phenol；
Benzazolyl compounds shown in the formula IV are dissolved in n,N-Dimethylformamide, NaH is added and stirs to get yellow solution,
Triaizine compounds shown in the Formula IV are added into the yellow solution to be reacted to obtain third crude product, the third is thick
OLED material of main part is obtained after product separating-purifying.
3. the preparation method of OLED material of main part according to claim 2, which is characterized in that alcohols solvent is anhydrous second
Alcohol.
4. the preparation method of OLED material of main part according to claim 2, which is characterized in that it is described carry out heating react
It further include that p-methyl benzenesulfonic acid is added to before the first crude product.
5. the preparation method of OLED material of main part according to claim 2, which is characterized in that described in atmosphere of inert gases
Under reacted to obtain the second crude product before, further include be added solution of potassium carbonate, 4-propyl bromide, palladium reagent.
6. the preparation method of OLED material of main part according to claim 2, which is characterized in that described by the described first thick production
Benzazolyl compounds shown in formula IV are obtained after object separating-purifying to specifically include:
Resulting first crude product ester soluble solvent and water extraction are reacted into heating, retains organic phase, by column chromatography for separation,
Then methylene chloride is used to be recrystallized to give benzazolyl compounds shown in formula IV as poor solvent as good solvent petroleum ether.
7. the preparation method of OLED material of main part according to claim 2, which is characterized in that described by the described second thick production
Triaizine compounds shown in Formula IV are obtained after object separating-purifying to specifically include:
Second crude product is put into purifying furnace, sublimation purification obtains triaizine compounds shown in Formula IV.
8. the preparation method of OLED material of main part according to claim 2, which is characterized in that described slightly to produce the third
OLED material of main part is obtained after object separating-purifying to specifically include: the third crude product with water being quenched, then filters, will filter
The sediment obtained afterwards is washed with water, ethyl alcohol, methanol respectively, then drying obtains OLED material of main part with re crystallization from toluene.
9. the preparation method of OLED material of main part according to claim 2, which is characterized in that described 2,4,6- tri- chloro- 1,
The ratio between amount of substance of boronic acid compounds shown in 3,5- triazine and the Formula V is 1:2.5.
10. a kind of OLED device, which is characterized in that the OLED device includes OLED material of main part as described in claim 1.
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Application publication date: 20191122 |