CN108727390A - Pyrene derivatives and its application in luminous organic material - Google Patents
Pyrene derivatives and its application in luminous organic material Download PDFInfo
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Abstract
Application the invention discloses pyrene derivatives and its in luminous organic material, the present invention also provides a kind of organic electroluminescence device, which includes the organic electroluminescent compounds.The compound of the present invention realizes carrier efficiently balanced transmission performance by introducing pyrene structure.
Description
Technical field
The present invention relates to a kind of novel pyrene derivatives organic compounds, more particularly to one kind being used for organic electroluminescence device
Compound and the application in organic electroluminescence device.
Background technology
Display of organic electroluminescence (hereinafter referred to as OLED) has from main light emission, low-voltage direct-current driving, all solidstate, regards
Angular width, light-weight, composition and a series of advantage such as simple for process, compared with liquid crystal display, display of organic electroluminescence
Backlight is not needed, visual angle is big, and power is low, and up to 1000 times of liquid crystal display, manufacturing cost is but less than response speed
The liquid crystal display of same resolution ratio, therefore, organic electroluminescence device has broad application prospects.
As OLED technology is in the continuous propulsion for illuminating and showing two big fields, people are for influencing OLED device performance
The research of efficient organic material focuses more on, the organic electroluminescence device of an excellent in efficiency long lifespan be typically device architecture with
The result of the optimization collocation of various organic materials.In most common OLED device structure, the organic of following type is generally included
Material：Hole-injecting material, hole mobile material, electron transport material, and assorted luminescent material (dyestuff or doping visitor
Body material) and corresponding material of main part etc..The phosphorescent light body material applied at present is all often to transmit energy with single carrier
Power, such as hole class transmit main body and electrical type transmits main body.Single carrier transport ability can cause electric in luminescent layer
The mismatch of son and hole, to cause serious efficiency roll-off and the lost of life.The excellent TADF of luminescent properties is in recent years
By common concern.The main body T1 of device can return to its S1 by RISC processes when TADF does main body, then pass through long-range
Energy transmission is transmitted to object and shines, this is different with convention body by short distance Dexter energy transmissions.TADF does main body
Exciton transfer is more effective in device, this is excellent one of the reason of device performance.More effective exciton transfer makes mixing for device
Miscellaneous concentration can reduce, and green device realizes high efficiency, the longevity that poor efficiency is roll-offed and grown simultaneously under low doping concentration
Life.After conventional fluorescent dyestuff acceptance subject material energy transmits, shone to the relaxation of ground state by singlet, but due to list
Line state exciton only occupies 25% ratio, and luminous efficiency is relatively low.And TADF materials are due to the energy between triplet state and singlet
Difference is minimum, can realize and pass through between reversed gap, improve the utilization rate of exciton.It is always that this field is exerted to find suitable TADF materials
Force direction.
Invention content
The shortcomings that in order to overcome the above material of convention body in the prior art, the offer present invention of the invention provide a kind of new
Type is used for the compound of organic electroluminescence device.The compound is by introducing novel pyrene derivative structure, it is easy to accomplish heat shock
Delayed fluorescence is sent out, carrier efficiently balanced transmission performance is realized, can be used in emitting red light device.The compound of the present invention
It is indicated by following general formula (I).
Wherein：
* connection site is indicated,
L is selected from key ,-O- ,-S- ,-NRa-、C1-C5Alkylidene, (C1-C3Alkylidene)-O- (C1-C3Alkylidene), C6-
C12Aryl, C3-C12Heteroaryl；
R1Selected from hydrogen, Ar, substituted or unsubstituted C1~C12Alkyl, halogen, cyano, nitro, hydroxyl, silylation, C6~
C30Substituted or unsubstituted aryl (preferably substituted or unsubstituted C6-C12Aryl), C3~C30Substitution or not
Substituted heteroaryl (preferably substituted or unsubstituted C3-C12Heteroaryl)；Work as R1For Ar when, two Ar are identical or not
Together；R3、R4、R5、R6、R7、R8It is independent to be selected from hydrogen, substituted or unsubstituted C1~C12Alkyl, halogen, cyano, nitro, hydroxyl,
Silylation, C6~C30Substituted or unsubstituted aryl (preferably substituted or unsubstituted C6-C12Aryl), C10~
C30Substituted or unsubstituted heteroaryl (preferably substituted or unsubstituted C4-C12Heteroaryl)；Or adjacent R4、R6、R7
Or R8Two carbon atoms being attached thereto form 5 yuan, 6 membered rings；
X is C (Rb)2、NRc,O,S；N is equal to 0,1；
M, r, p, q, s and t are independently 0,1 or 2；When r is 2, two R3It is identical or differ；When m is 2, two
A R4It is identical or differ；When p is 2, two R5It is identical or differ；When q is 2, two R6Identical or not phase
Together；When s is 2, two R7It is identical or differ；When t is 2, two R8It is identical or differ,
Ra、RbAnd RcIt is independent to be selected from hydrogen, C1-C5Alkylidene, halogen, cyano, nitro, hydroxyl；Two RbIt is identical or
It is different.
In a preferred embodiment of the present invention, the substituent group in pyrene structure being connected with Ar is axially symmetric structure.
In another preferred embodiment of the present invention, the R7With the R of symmetric position8For identical substituent group.
In a preferred embodiment of the present invention, the L is key, substitution or unsubstituted phenyl.
Preferably, above-mentioned aromatic hydrocarbon group is independent takes selected from phenyl, by furyl, thienyl, pyrrole radicals and/or pyridyl group
Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, indenyl, fluorenyl and its derivative in generation, fluoranthene base, triphenylene,
Pyrenyl, base,At least one of base and aphthacene base.It is highly preferred that the xenyl includes 2- xenyls, 3- xenyls
With 4- xenyls, the terphenyl includes p- terphenyl -4- bases, p- terphenyl -3- bases, p- terphenyl -2-
Base, m- terphenyl -4- bases, m- terphenyl -3- bases and m- terphenyl -2- bases；The naphthalene be 1- naphthalenes and/or
2- naphthalenes；The anthryl includes at least one of 1- anthryls, 2- anthryls and 9- anthryls；The fluorenyl includes 1- fluorenyls, 2- fluorenes
At least one of base, 3- fluorenyls, 4- fluorenyls and 9- fluorenyls；The fluorenyl derivative includes 9,9 '-dialkyl fluorenes, 9,9 '-spiral shells
At least one of two fluorenes and indenofluorene；The pyrenyl includes at least one of 1- pyrenyls, 2- pyrenyls and 4- pyrenyls；It is described
Aphthacene base includes at least one of 1- aphthacenes base, 2- aphthacenes base and 9- aphthacene bases.
According to the present invention, above-mentioned heteroaryl refers to having at least one hetero atom and having certain amount ring skeleton atom
Monocycle or polycyclic aromatic group, the hetero atom include one or more hetero atoms selected from B, N, O, S, P (=O), Si and P,
The preferably described hetero atom includes one or more hetero atoms for being selected from O, S and N；Wherein, the Ar being mentioned above is independently
Ground is C3-C90Substituted or unsubstituted heteroaryl, which refers to the heteroaryl, can have 3-90 backbone carbon atoms, it is preferable that Ar
It is separately C5-C30Substituted or unsubstituted heteroaryl, which refers to heteroaryl, has 5-30 backbone carbon atoms.
Preferably, above-mentioned heteroaryl is independent selected from furyl, benzofurane base, thienyl, tolylthiophene base, pyrroles
Base, phenylpyrrole base, pyridyl group, phenylpyridyl, pyrazinyl, fluorenyl, indeno fluorenyl, quinoline, triazine radical, benzofuranyl,
Benzothienyl, phentriazine, benzopyrazines, isobenzofuran-base, indyl, benzoquinoline, dibenzofuran group, dibenzo
Diazole, coffee quinoline base, coffee quinoline benzothiazolyl and the benzo that thienyl, dibenzopyrrole base, carbazyl and its derivative, phenyl replace
At least one of dioxolyl, wherein the carbazole radical derivative can include but is not limited to 9- phenyl carbazoles,
At least one of 9- naphthyl carbazoles benzo carbazole, dibenzo-carbazole and indolocarbazole.
Specifically, R in above-mentioned logical formula (I)1、R3、R4、R5、R6、R7、R8、Ra、Rb、RcIt is independently selected from H, C1~C6Alkyl,
Cl, Br, CN or Si (CH3)3。
Further, in logical formula (I) of the invention, work as R1、R3、R4、R5、R6、R7、R8、Ra、Rb、RcIt is respectively and independently selected from alkane
When base, preferred alkyl includes：Methyl, ethyl, isopropyl, tertiary butyl, cyclopenta, cyclohexyl.
In the present invention, Ca-CbExpression way represent the carbon atom number that the group has as a~b, unless specifically indicated, one
As for the carbon atom number do not include the carbon atom number of substituent group.
In the present invention, include the concept of the identical isotope of chemical property for the statement of chemical element, such as " hydrogen "
Statement also includes chemical property identical " deuterium ", the concept of " tritium ".
Hetero atom in the present invention is often referred to selected from B, N, O, S, P, P (=O), Si and the atom in Se or atomic group.
In the present invention, when defined group is the group of substitution, it is preferred that taking on the substituted group
Include but not limited to halogen, nitro, cyano, C for base1-C6Alkyl or C1-C6Alkoxy, C5-C12Aromatic hydrocarbon group or
Person's heteroaryl etc., preferably C1~C5Alkyl, alkoxy, phenyl, naphthalene, pyridyl group, pyrrole radicals, more preferably methyl, isopropyl
The quantity of base, phenyl, naphthalene, pyridyl group, substituent group can be 1,2,3,4,5,6 and 6 or more.
In a preferred embodiment of the present invention, for filming performance and processing performance aspect the considerations of, described
The molecular weight of compound is between 400-1200, between preferably 450-1100.
Further, in logical formula (I) of the invention, following concrete structure compounds can preferably be gone out：A1-A17, these changes
It is only representative to close object.
The present invention has precursor structure derived from the pyrene of conjugated polycyclic characteristic, and interatomic bond energy is high, has good heat
Stability；Intermolecular solid-state accumulation, improves the service life of material in being conducive to；
As representative examples, the good separating effect of HOMO and LUMO of pyrene derivative compound.In addition, compound derived from pyrene
Structure combination triplet state and the energy difference Δ Est values of singlet are small, it is easy to accomplish thermal excitation delayed fluorescence (TADF), as representative
Example, part of compounds Δ Est results are as follows：
The present invention also provides purposes of the above-mentioned organic electroluminescent compounds in preparing organic electroluminescence device.This
The organic electroluminescence device structure of invention has no difference with well known device, generally comprises first electrode, second electrode and inserts
Enter one layer between the first electrode and second electrode or mostly at organic layer, which is characterized in that the organic layer includes above-mentioned
Organic electroluminescent compounds.As the organic layer between first electrode and second electrode, usually there are electron injecting layer, electronics to pass
The organic layers such as defeated layer, luminescent layer, hole transmission layer, hole injection layer.The compound of the present invention may be used as but be not limited to shine
Layer material.
The present invention also provides purposes of the above-mentioned organic electroluminescent compounds in preparing organic electroluminescence device.
Wherein, the organic electroluminescent compounds may be used as but be not limited to emitting layer material.
The present invention also provides a kind of organic electroluminescence device, which includes first electrode, second electrode and insertion
One layer between the first electrode and second electrode or mostly at organic layer, the organic layer includes above-mentioned organic electroluminescent
Close object.
In a preferred embodiment of the present invention, the organic electroluminescence device is emitting red light device.
When the compound of the present invention is used as light emitting host, the mechanism of object is sensitized using main body, it can be by the triplet state of main body
Exciton passes to rapidly light-emitting guest by TADF processes, more effectively utilizes triplet excitons, avoids efficiency roll-off serious
Problem improves the luminous efficiency of organic electroluminescence device, is suitable for emitting red light device；The compound of the present invention is used as shining
When object, it is capable of the energy of acceptance subject transmission, realizes that triplet state is passed through between the reversed gap of singlet, improve exciton and utilize
Rate, suitable for green device.The HOMO and lumo energy for adjusting the compounds of this invention are modified by specific substituent group, it will
The each group of precursor structure effectively connects, and is adjusted to the band gap of material, overcomes when as material of main part, low
The technical issues of luminescent device poor efficiency is roll-offed under doping concentration realizes the long service life, is more suitable for the material of red device
Option.In addition, preparation is simple for the compounds of this invention, raw material is easy to get, and is suitable for volume production amplification.
Specifically, the compound in the logical formula (I) can be, but not limited to be used as shining in organic electroluminescence device
Layer material.
Below by by taking multiple synthetic examples as an example come be described in detail the present invention above-mentioned noval chemical compound specific preparation method, but
The preparation method of the present invention is not limited to this multiple synthetic example, and those skilled in the art can not depart from its basis
Any modification, equivalent substitution, improvement and etc. are carried out under the premise of principle of the present invention, and the right that this method is expanded to the present invention is wanted
Within the scope of the technical solution for asking book claimed.
Specific implementation mode
In order to make those skilled in the art more fully understand the present invention, With reference to embodiment to the present invention make into
One step is described in detail.
The compound for the synthetic method that do not mentioned in the present invention is all the raw produce obtained by commercial sources.Implement
Various chemicals such as petroleum ether, ethyl acetate, n-hexane, toluene, tetrahydrofuran, dichloromethane, four chlorinations used in example
Bis- (bromomethyl) benzene of carbon, acetone, 1,2-, CuI, o-phthaloyl chloride, phenylhydrazine hydrochloride, trifluoroacetic acid, acetic acid, trans--diamino
Hexamethylene, iodobenzene, cesium carbonate, potassium phosphate, ethylenediamine, benzophenone, cyclopentanone, 9-Fluorenone, sodium tert-butoxide, Loprazolam, 1-
Bromo- 2- methyl naphthalenes, o-dibromobenzene, butyl lithium, Bromofume, o-dibromobenzene, benzoyl peroxide, 1- (2- bromophenyls) -2- first
Base naphthalene, N- bromo-succinimides, methoxyl methyl San Jia Ji phosphonium chlorides, tris(dibenzylideneacetone) dipalladium, four (triphenylphosphines)
Palladium, 1,3- pairs of 2-phenyl-phosphine oxide nickel chloride, carbazole, 3,6- Dimethylcarbazoles, 3- (2- naphthalenes) -6- phenyl carbazoles, N- phenyl
The basic chemical industries raw materials such as carbazole -3- boric acid, 9- (2- naphthalenes) carbazole -3- boric acid chemical products can be commercially available at home.
The analysis detection of intermediate and compound in the present invention uses AB SCIEX mass spectrographs (4000QTRAP) and cloth Shandong
Gram Nuclear Magnetic Resonance (400M).
Synthetic example：
The synthesis of 1. compound A1 of synthetic example
Select pyrene as starting material, by 20.2g pyrenes (0.1mol) be dissolved in 400mL CH2Cl2,400mL CH3CN with
And mixed solution is added in the mixed solution of 1000mL water, 175g (0.8mol) sodium metaperiodates and 2.5g (12mmol) RuCl3.Mixing
Liquid is maintained at 30-40 DEG C of heating reaction 12h and stays overnight.Reaction finishes, and 3.5L water is added in mixed liquor, and be vigorously stirred.Then it passes through
Liquid separation, water phase are extracted 5 times with 2L CH2Cl2.Organic phase is merged together, dry with saturated common salt water washing.Organic phase is through dense
Contracting, obtains 4.4g dark yellow solid intermediate M1, yield 17%.
Under nitrogen protection, intermediate M1 (0.1mol, 1eq.), toluene 200ml are added into 1L there-necked flasks, opens stirring,
O-phenylenediamine (5eq) is added, is heated to flowing back, reaction 4h. reactions finish, and MnO2 is added into reaction solution, continues to heat, flows back
The filtering of 2h. reaction solutions is reacted, filtrate washing detaches organic phase, dry, and concentration with ethyl alcohol recrystallization, obtains intermediate M2
(4.8g, 92.3%)
Acetic acid 100ml is added into 250ml reaction bulbs for nitrogen protection, and intermediate 2 (0.05mol, 1eq) unlatching is added and stirs
It mixes, bromine (1.1eq) is added dropwise, 3h is reacted in stirring.Reaction solution is poured into water, and filtering, with water, ethyl alcohol washes much filtrate.Toluene is tied again
It is brilliant to obtain intermediate M3 (4.2g, 87.5%).
Under nitrogen protection, 3,6- diisopropyls carbazole (0.05mol, 1.0eq), intermediate M3 are added into 1L there-necked flasks
(1.05eq), sodium tert-butoxide (1.5eq), toluene 500mL add Pd2 (dba) 3 (, 0.5%eq), inject 10% with syringe
Tri-tert-butylphosphine (1%eq) opens stirring, is heated to 100 degrees Celsius, reaction overnight, is cooled to 50 degrees centigrades, adds 2L first
Benzene dilutes, and water 3000ml is added to wash, liquid separation, organic phase drying, rushes quick column (silica gel dosage), and elutriant is in black, is concentrated, filtering
Obtain yellow solid powder 14.2g, yield 61%.
The magnetic resonance spectroscopy data of compound A1：
1H NMR (400MHz, Chloroform) δ 9.39 (s, 3H), 8.96 (s, 1H), 8.19 (s, 1H), 8.01 (d, J=
10.0Hz, 3H), 7.80 (s, 4H), 7.67 (s, 4H), 7.52 (s, 1H), 7.39 (d, J=6.6Hz, 2H), 7.15 (s, 1H),
2.87 (s, 2H), the synthesis of 1.20 (s, 12H) synthetic examples, 2. compound A2
With compound A1, difference is to replace with 3,6- diisopropyl carbazoles into 1, the 8- diformazans of equivalent synthesis step
Base -3,6- diphenyl carbazole, after reaction, isolated yellow solid 17.1g, yield 72.3%.
The magnetic resonance spectroscopy data of compound A2：
1H NMR (400MHz, Chloroform) δ 9.43 (s, 2H), 8.67 (s, 1H), 7.97 (dd, J=10.4,
9.6Hz, 6H), 7.80 (s, 4H), 7.75 (s, 4H), 7.67 (s, 4H), 7.64 (d, J=7.8Hz, 1H), 7.45 (d, J=
12.0Hz,10H),2.50(s,6H).
The synthesis of 3. compound A-13 of synthetic example
Under nitrogen protection, be added into 1L there-necked flasks 3,6- bis- (2- naphthalenes) -9- (4- boric acid phenyl) carbazole (0.05mol,
1.0eq), intermediate M3 (1.05eq), sodium carbonate (1.5eq), toluene 500mL, ethyl alcohol 200ml, water 200ml add Pd2
(PPh3) 4 (0.5%eq) opens stirring, is heated to 100 degrees Celsius, and reaction overnight, is cooled to 50 degrees centigrades, adds washing,
Quick column (silica gel dosage) is rushed in liquid separation, organic phase drying, and elutriant is in black, and yellow solid powder is obtained by filtration in concentration
15.6g, yield 65%.
The magnetic resonance spectroscopy data of compound A-13：
1H NMR (400MHz, Chloroform) δ 8.29 (s, 5H), 8.19-7.98 (m, 20H), 7.90 (t, J=
10.0Hz,16H),7.80(s,9H),7.74–7.53(m,36H),7.50(s,2H),7.38(s,5H).
The synthesis of 4. compound A4 of synthetic example
The same compound A-13 of synthesis step, difference are to replace with 3,6- bis- (2- naphthalenes) -9- (4- boric acid phenyl) carbazole
3,6- bis- (4- aminomethyl phenyls) -9- (2,6- dimethyl -4- boric acid phenyl) carbazole of equivalent, it is after reaction, isolated
White solid 12.7g, yield 58.3%.
1H NMR(400MHz,Chloroform)δ8.92(s,4H),8.19–7.96(m,10H),7.89–7.75(m,
14H), 7.69 (d, J=16.0Hz, 9H), 7.62-7.09 (m, 20H), 7.16 (s, 8H), 7.16 (s, 8H), 2.50 (s, 12H),
The synthesis of 2.34 (s, 12H) synthetic examples, 5. compound A-45
The same compound A-13 of synthesis step, difference are to replace with 3,6- bis- (2- naphthalenes) -9- (3- boric acid phenyl) carbazole
3,6- dibiphenylyls -9- (2,6- dimethyl -4- boric acid phenyl) carbazole of equivalent, after reaction, isolated yellow are solid
Body 11.9g, yield 60.5%.
1H NMR(400MHz,Chloroform)δ8.50(s,2H),8.21(s,1H),8.04(s,1H),7.99(s,
2H),7.87(s,1H),7.80(s,4H),7.78–7.63(m,10H),7.62–7.23(m,21H),7.41(s,1H),7.33
(d, J=64.0Hz, 10H), 7.25 (s, 8H)
The synthesis of 6. compound A6 of synthetic example
Acetic acid 100ml is added into 250ml reaction bulbs for nitrogen protection, and intermediate M2 (0.05mol, 1eq) unlatchings are added and stir
It mixes, bromine (2.2eq) is added dropwise, 3h is reacted in stirring.Reaction solution is poured into water, and filtering, with water, ethyl alcohol washes much filtrate.Toluene is tied again
It is brilliant to obtain intermediate M3B (4.2g, 87.5%).
Intermediate M3B is mixed with equivalent CuCN, is placed in DMF, is heated to 120 DEG C, overnight, reaction finishes, water for reaction
It washes, ethyl acetate extraction, concentration obtains intermediate M4.
The same compound A-13 of synthesis step, difference are intermediate M3 replacing with M4, by 3,6- bis- (2- naphthalenes) -9- (3-
Boric acid phenyl) carbazole replaces with 5- phenyl -11- (4- phenyl boric acids)-indolocarbazole of equivalent and detaches after reaction
To yellow solid 11.5g, yield 74.3%.
1H NMR(400MHz,Chloroform)δ9.18(s,1H),8.74(s,2H),8.55(s,1H),8.19(s,
1H), 7.91 (d, J=4.0Hz, 4H), 7.80 (s, 4H), 7.70 (dd, J=7.7,0.6Hz, 1H), 7.67 (s, 2H), 7.68-
7.47 (m, 10H), 7.40 (s, 1H), 7.16 (dd, J=22.0,14.0Hz, 1H)
The synthesis of 7. compound A7 of synthetic example
With compound A1, difference is to replace with 3,6- bis- (2- naphthalenes) -9- (3- boric acid phenyl) carbazole synthesis step
5- phenyl -7- (4- phenyl boric acids)-indolocarbazole of equivalent, after reaction, isolated yellow solid 9.9g, yield is
65.6%.1H NMR (400MHz, Chloroform) δ 8.75 (s, 1H), 8.55 (d, J=3.5Hz, 1H), 8.19 (s, 4H),
8.01 (d, J=10.0Hz, 1H), 7.91 (d, J=4.0Hz, 2H), 7.80 (s, 2H), 7.70 (dd, J=7.7,0.6Hz, 1H),
7.67 (s, 1H), 7.68-7.47 (m, 4H), 7.40 (s, 4H), 7.16 (dd, J=22.0,14.0Hz, 2H)
The synthesis of 8. compound A-28 of synthetic example
With compound A6, difference is to replace with 5- phenyl -11- (4- phenyl boric acids)-indolocarbazole synthesis step
3, the 6- diphenyl carbazoles of equivalent, after reaction, isolated yellow solid 9.6g, yield 46.7%.
1H NMR(400MHz,Chloroform)δ9.58(s,2H),8.09(s,1H),8.09–7.83(m,5H),8.09–
7.78(m,32H),8.09–7.23(m,9H),7.41(s,3H),7.41(s,4H).
The synthesis of 9. compound A9 of synthetic example
The same compound A-13 of synthesis step, difference are intermediate M3 replacing with M4, by 3,6- bis- (2- naphthalenes) -9- (3-
Boric acid phenyl) carbazole replaces with 3- (2- triphenylenes) -9- (4- phenyl boric acids)-indolocarbazole of equivalent, after reaction,
Isolated yellow solid 12.8g, yield 67.2%.
1H NMR(400MHz,Chloroform)δ8.79(s,1H),8.55(s,1H),8.46(s,1H),8.39–8.28
(m, 4H), 7.91 (d, J=4.0Hz, 4H), 7.80 (s, 4H), 7.72-7.37 (m, 12H), 7.35 (s, 2H), 7.25 (s, 2H),
7.13 (d, J=20.0Hz, 2H)
The synthesis of 10. compound A10 of synthetic example
Under nitrogen protection, intermediate M1 (0.1mol, 1eq.), toluene 200ml are added into 1L there-necked flasks, opens stirring,
4,5- dicyanos-o-phenylenediamine (5eq) is added, is heated to flowing back, reaction 4h. reactions finish, and MnO2 is added into reaction solution, after
Continuous heating, the filtering of back flow reaction 2h. reaction solutions, filtrate washing detach organic phase, dry, and concentration with ethyl alcohol recrystallization, obtains
Intermediate M2B (4.8g, 92.3%)
Acetic acid 100ml is added into 250ml reaction bulbs for nitrogen protection, and intermediate M2 (0.05mol, 1eq) unlatchings are added and stir
It mixes, bromine (2.2eq) is added dropwise, 3h is reacted in stirring.Reaction solution is poured into water, and filtering, with water, ethyl alcohol washes much filtrate.Toluene is tied again
It is brilliant to obtain intermediate M3C (4.2g, 87.5%).
The same compound A-13 of synthesis step, difference are intermediate M3 replacing with M3C, by 3,6- bis- (2- naphthalenes) -9- (4-
Boric acid phenyl) carbazole replaces with 3,6- bis- (1- dibenzofuran groups) -9- (4- boric acid phenyl) carbazole of equivalent, and reaction terminates
Afterwards, isolated yellow solid 9.6g, yield 46.7%.
1H NMR(400MHz,Chloroform)δ9.62(s,4H),9.43(s,4H),8.71(s,4H),8.27–7.98
(m, 16H), 7.98-7.60 (m, 20H), 7.60-7.44 (m, 9H), 7.40 (d, J=8.0Hz, 6H), 7.31 (s, 2H)
The synthesis of 11. compound A11 of synthetic example
With compound A10, difference is 3,6- bis- (1- dibenzofuran groups) -9- (4- boric acid phenyl) click synthesis step
Azoles replaces with 3- (2- spiro fluorenes) -9- (4- boric acid phenyl) carbazole of equivalent, after reaction, isolated yellow solid
9.9g, yield 65.6%.
1H NMR(400MHz,Chloroform)δ9.30(s,2H),9.11(s,2H),8.87(s,1H),8.79(s,
2H), 8.55 (s, 1H), 8.12 (d, J=24.9Hz, 2H), 8.27-8.01 (m, 3H), 8.27-7.97 (m, 5H), 8.27-7.83
(m, 12H), 8.37-7.58 (m, 14H), 8.12-7.58 (m, 13H), 7.69 (d, J=76.0Hz, 2H), 7.51 (d, J=
8.0Hz, 2H), 7.33 (d, J=6.7Hz, 3H), 7.24 (d, J=4.0Hz, 4H), 7.13 (d, J=20.0Hz, 2H)
The synthesis of 12. compound A12 of synthetic example
The same compound A-13 of synthesis step, difference are to replace with 3,6- bis- (2- naphthalenes) -9- (4- boric acid phenyl) carbazole
3- (9,9- dimethyl fluorene) -9- (4- boric acid phenyl) carbazole of equivalent, after reaction, isolated yellow solid 13.5g,
Yield is 72.8%.
1H NMR(400MHz,Chloroform)δ9.96(s,1H),8.94(s,2H),8.55(s,1H),8.38–8.12
(m, 3H), 8.08 (d, J=8.4Hz, 1H), 8.04 (s, 1H), 7.99 (s, 2H), 7.91 (d, J=4.0Hz, 4H), 7.80 (s,
4H), 7.67 (s, 3H), 7.53 (d, J=5.1Hz, 2H), 7.34 (s, 1H), 7.13 (d, J=20.0Hz, 2H), 1.69 (s,
6H).
The synthesis of 13. compound A13 of synthetic example
The same compound A-13 of synthesis step, difference are intermediate M3 replacing with intermediate M4, by 3,6- bis- (2- naphthalenes)-
9- (4- boric acid phenyl) carbazole replaces with 3,6- diphenyl -9- (2,6- dimethyl -4- bromophenyls) carbazole of equivalent, reaction knot
Shu Hou, isolated yellow solid 15.4g, yield 76.1%.
1H NMR(400MHz,Chloroform)δ8.91(s,2H),8.07(s,2H),8.07(s,2H),8.07(s,
2H),8.15–7.25(m,28H),7.41(s,1H),7.41(s,3H),2.50(s,6H).
The synthesis of 14. compound A14 of synthetic example
With compound A13, difference is 3,6- diphenyl -9- (2,6- dimethyl -4- bromophenyls) carbazole synthesis step
3,6- diphenyl -9- (3- phenyl boric acids) carbazole of equivalent is replaced with, after reaction, isolated yellow solid 10.6g is received
Rate is 69.8%.1H NMR(400MHz,Chloroform)δ8.90(s,2H),8.47(s,2H),8.21(s,1H),7.87(s,
2H), 7.80 (s, 3H), 7.77-7.62 (m, 9H), 7.62-7.30 (m, 12H), 7.41 (s, 2H), 7.41 (s, 1H) synthesis are real
Apply the synthesis of 15. compound A15 of example
With compound A1, difference is to replace with 3,6- diisopropyl carbazoles into 9, the 9- dimethyl of equivalent synthesis step
Acridine, after reaction, isolated yellow solid 10.4g, yield 67.8%.
1H NMR (400MHz, Chloroform) δ 8.96 (s, 2H), 8.08 (d, J=8.5Hz, 1H), 8.01 (d, J=
10.0Hz,3H),7.80(s,3H),7.67(s,3H),7.22–7.14(m,5H),6.94(s,1H),1.69(s,6H).
The synthesis of 16. compound A16 of synthetic example
Synthesis step is with compound A1, and difference is to replace with intermediate M3 into the intermediate M3B of equivalent, by 3,6- bis-
Isopropylcarbazole replaces with 3, the 6- diphenyl carbazoles of equal doubling doses, and after reaction, isolated yellow solid 11.4g is received
Rate is 68.4%.1H NMR(400MHz,Chloroform)δ8.32(s,9H),8.09(s,9H),8.09(s,8H),7.98(d,
J=86.5Hz, 14H), 8.09-7.78 (m, 23H), 8.09-7.22 (m, 91H), 7.41 (s, 15H), 7.41 (s, 5H) synthesis
The synthesis of 17. compound A17 of embodiment
With compound A16, difference is to replace with 3,6- diphenyl carbazoles into the phenoxazine of equivalent synthesis step, reaction
After, isolated yellow solid 9.6g, yield 12.5%.
1H NMR (400MHz, Chloroform) δ 7.80 (s, 1H), 7.67 (d, J=3.9Hz, 2H), 7.14 (s, 1H),
7.00 (d, J=12.0Hz, 2H), 6.93 (s, 1H)
The analysis detecting data row of specific preferably synthetic structural compounds disclosed in the embodiment of the present invention are in table 1 below：
Device embodiments：
The typical structure of the OLED organic electroluminescence devices prepared in device embodiments is：
Substrate/anode/hole injection layer (HIL)/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer
(ETL)/electron injecting layer (EIL)/cathode
Above-mentioned "/" indicates to be laminated in order between different function layer.
Device embodiments 1 (comparative example 1)
Emitting layer material uses red phosphorus photoinitiator dye D1, collocation main body H1.Each functional layer material molecular structure is as follows：
A) ITO (tin indium oxide) glass is cleaned：Respectively each 15 points of ito glass is cleaned with deionized water, acetone, EtOH Sonicate
Then clock is handled 2 minutes in plasma cleaner；
B) vacuum evaporation or solution film forming hole transmission layer NPB, thickness 50nm on anode ito glass；
C) on hole transmission layer NPB, vacuum evaporation luminescent layer H1+D1 (5%), thickness 30nm；
D) on luminescent layer, vacuum evaporation hole blocking layer PBD, thickness 10nm；
E) on hole blocking layer PBD, vacuum evaporation electron transfer layer Alq3
F) on electron transfer layer Alq3, vacuum evaporation electron injecting layer LiF, thickness 0.5nm；
G) on electron injecting layer LiF, vacuum evaporation cathode Al, thickness 100nm.The structure of device is ITO/NPB
(50nm)/H1：D1 (5%) (30nm)/PBD (10nm)/Alq3 (20nm)/LiF (0.5nm)/Al (100nm).
2. the compounds of this invention of device embodiments is as material of main part
Organic electroluminescence device is prepared using method same as Example 1, difference is, H1 compounds are replaced
It is changed to compound A1.
3. the compounds of this invention of device embodiments is as material of main part
Organic electroluminescence device is prepared using method same as Example 1, difference is, H5 compounds are replaced
It is changed to compound A1.
4. the compounds of this invention of device embodiments is as material of main part
Organic electroluminescence device is prepared using method same as Example 1, difference is, H6 compounds are replaced
It is changed to compound A1.
5. the compounds of this invention of device embodiments is as material of main part
Organic electroluminescence device is prepared using method same as Example 1, difference is, H7 compounds are replaced
It is changed to compound A1.
6. the compounds of this invention of device embodiments is as material of main part
Organic electroluminescence device is prepared using method same as Example 1, difference is, H8 compounds are replaced
It is changed to compound A1.
7. the compounds of this invention of device embodiments is as material of main part
Organic electroluminescence device is prepared using method same as Example 1, difference is, by H11 compounds
Replace with compound A1.
8. the compounds of this invention of device embodiments is as material of main part
Organic electroluminescence device is prepared using method same as Example 1, difference is, by H13 compounds
Replace with compound A1.
Concrete preferred structure compound disclosed in device embodiments of the present invention is applied in organic electroluminescence device
Device performance detection data refers to the following table 2：
Table 2
By in table 2, device embodiments 2-8 and device embodiments 1 (comparative example 1), in organic electroluminescence device structure
In the case of other materials is identical, series compound of the present invention replaces H1 in comparative device embodiment 1 to be used as the layer main body material that shines
Material, from 4.3 to 3.8, current efficiency is promoted from 23cd/A to 35cd/A the operating voltage of device, is had and is very significantly carried
Ascending effect, at the same device lifetime also obtained significantly extending.Series compound of the present invention has thermal excitation delayed fluorescence
Matter, the light emitting host material being used as is with long-rangeEnergy transmission is transmitted to object and shines, and passes through short distance with convention body
The better matching that Dexter energy transmissions are more effective compared to exciton transfer and this series material is mutual, avoids efficiency
It roll-offs serious problem, significantly increases the luminous efficiency of device, the dyestuff doping concentration of device reduces, while realizing high
Luminous efficiency reduces cost.
The preferred embodiment of the present invention has been described above in detail, still, during present invention is not limited to the embodiments described above
Detail can carry out a variety of simple variants to technical scheme of the present invention within the scope of the technical concept of the present invention, this
A little simple variants all belong to the scope of protection of the present invention.
It is further to note that specific technical features described in the above specific embodiments, in not lance
In the case of shield, can be combined by any suitable means, in order to avoid unnecessary repetition, the present invention to it is various can
The combination of energy no longer separately illustrates.
In addition, various embodiments of the present invention can be combined randomly, as long as it is without prejudice to originally
The thought of invention, it should also be regarded as the disclosure of the present invention.
Claims (9)
1. the structure of a kind of compound, compound is indicated by following general formula (I),
Wherein：
* connection site is indicated,
L is selected from key ,-O- ,-S- ,-NRa-、C1-C5Alkylidene, (C1-C3Alkylidene)-O- (C1-C3Alkylidene), C6-C12Virtue
Alkyl, C3-C12Heteroaryl；
R1Selected from hydrogen, Ar, substituted or unsubstituted C1~C12Alkyl, halogen, cyano, nitro, hydroxyl, silylation, C6~C30Take
Generation or unsubstituted aryl, C3~C30Substituted or unsubstituted heteroaryl；Work as R1For Ar when, two Ar are identical or not
Together；
R3、R4、R5、R6、R7、R8It is independent to be selected from hydrogen, substituted or unsubstituted C1~C12Alkyl, halogen, cyano, nitro, hydroxyl,
Silylation, C6~C30Substituted or unsubstituted aryl, C10~C30Substituted or unsubstituted heteroaryl；Or it is adjacent
R4、R6、R7Or R8Two carbon atoms being attached thereto form 5 yuan or 6 membered rings；
X is C (Rb)2、NRc,O,S；N is equal to 0,1；
M, r, p, q, s and t are independently 0,1 or 2；When r is 2, two R3It is identical or differ；When m is 2, two R4Phase
Together or differ；When p is 2, two R5It is identical or differ；When q is 2, two R6It is identical or differ；When s is
When 2, two R7It is identical or differ；When t is 2, two R8It is identical or differ,
Ra、RbAnd RcIt is independent to be selected from hydrogen, C1-C5Alkylidene, halogen, cyano, nitro, hydroxyl；Two RbIt is identical or different.
2. compound according to claim 1, the substituent group in pyrene structure being connected with Ar is axially symmetric structure.
3. compound according to claim 1, the R7With the R of symmetric position8For identical substituent group.
4. compound according to any one of claim 1-3, the aromatic hydrocarbon group is stood alone as selected from phenyl, by furans
Base, thienyl, pyrrole radicals and/or pyridyl group substitution phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, indenyl, fluorenes
Base and its derivative, fluoranthene base, triphenylene, pyrenyl, base,At least one of base and aphthacene base.
5. compound according to any one of claim 1-3, the heteroaryl be selected from furyl, benzofurane base,
Thienyl, tolylthiophene base, pyrrole radicals, phenylpyrrole base, pyridyl group, phenylpyridyl, pyrazinyl, fluorenyl, indeno fluorenyl, quinoline
Quinoline, triazine radical, benzofuranyl, benzothienyl, phentriazine, benzopyrazines, isobenzofuran-base, indyl, benzo quinoline
Diazole, the coffee that quinoline, dibenzofuran group, dibenzothiophene, dibenzopyrrole base, carbazyl and its derivative, phenyl replace
At least one of quinoline base, coffee quinoline benzothiazolyl and benzodioxole group.
6. compound according to claim 1, the one kind of the compound in following compound：
7. a kind of organic electroluminescence device, which includes first electrode, second electrode and is inserted into the first electrode and the
One layer between two electrodes or mostly at organic layer, which is characterized in that the organic layer includes any one of claim 1~6 institute
The compound stated.
8. organic electroluminescence device according to claim 7, the organic layer includes luminescent layer, and the luminescent layer includes
Compound according to any one of claims 1 to 6.
9. the organic electroluminescence device according to any one of claim 7~8, the organic electroluminescence device are
Emitting red light device.
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| CN111793009A (en) * | 2020-07-17 | 2020-10-20 | 河北工业大学 | Phthalonitrile monomer containing spiro structure and resin thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110759919A (en) * | 2018-12-06 | 2020-02-07 | 广州华睿光电材料有限公司 | Pyrene quinone organic compound and application thereof |
| CN110129038A (en) * | 2019-06-10 | 2019-08-16 | 武汉华星光电半导体显示技术有限公司 | Peony thermal activation delayed fluorescence material and its production method, electroluminescent device |
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