CN109251194A - A kind of triaizine compounds and its organic luminescent device of the class formation containing fluorenes - Google Patents
A kind of triaizine compounds and its organic luminescent device of the class formation containing fluorenes Download PDFInfo
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Abstract
The invention discloses the triaizine compounds and its organic luminescent device of a kind of class formation containing fluorenes, are related to organic optoelectronic materials technology.On the one hand, triazine group has high electron mobility and lower energy level using it as the compound of center structure, reconnects pyridine groups, the electron mobility of compound is obviously improved as typical strong electron-withdrawing group group.On the one hand, fluorenes class group is the space structure of 3 D stereo, can effectively prevent intermolecular aggregation, it is made to be not easy to crystallize；Easily modification, strong rigid advantage stablize compound structure in fluorenes class group.On the other hand, compound structure possesses extensible three-dimensional structure, and continuous pi-conjugated system brings preferable electron mobility, to have high electron mobility；Also, the combination of three balances carrier transport.It is applied to organic luminescent device, is used as electron transfer layer or hole blocking layer, device shows the advantage that driving voltage is low, luminous efficiency is high.
Description
Technical field
The present invention relates to the triaizine compounds of organic photoelectrical material technical field more particularly to a kind of class formation containing fluorenes and its
Organic luminescent device.
Background technique
Organic electroluminescent LED (Organic Light Emitting Diode, OLED) is to utilize electrons and holes
The recombination luminescence in organic film and the luminescent device prepared, have the advantage that (1) from main light emission, does not need backlight；
(2) brightness is high, there is high contrast, pure in colour, the problem of almost without visible angle；(3) ultra-thin, by very thin organic
Material coating and basis material are constituted, small in size to be suitable for portable product；(4) power consumption is very small, environmental protection and energy saving；(5) it rings
It answers speed fast, is the one thousandth of LCD；(6) use temperature range is wide, remains to normally show at -40 DEG C.
Organic charge transport material is a kind of when there is carrier (electronics or hole) to inject, can be under electric field action
The controllable oriented and ordered migration of carrier is realized to realize the organic semiconducting materials of charge transmission.Relative to inorganic material,
Organic charge transport material have at low cost, small toxicity, it is easily processed into type and be chemically modified to meet different needs, can
The advantages that make Grazing condition device, is widely used to xerography, sensor, electroluminescent, field-effect tube and too at present
The numerous areas such as positive energy battery, become one of the hot spot studied both at home and abroad.Organic charge transport material can divide organic hole to transmit
(p-type) material and organic electronic transmit (N-shaped) material.Compared with organic p-type material, the development of n-type material is slower, such as 8-
Hydroxyquinoline aluminum (Aq3) and oxadiazole derivatives PBD be the relatively early n-type material studied.
The hole mobility of hole mobile material is typically much deeper than the electron mobility of electron transport material in device, this meeting
Cause being remarkably decreased for device performance.It is adjusted so how to design the better electron transport material of new performance, is always
Those skilled in the art's urgent problem to be solved.
Summary of the invention
The object of the present invention is to provide the triaizine compounds and its organic luminescent device of a kind of class formation containing fluorenes.The present invention mentions
The triaizine compounds thermal stability of the class formation containing fluorenes supplied is high, glass transition temperature is high, is not easy to crystallize, which is used for electricity
Manufactured organic luminescent device in sub- transport layer, shows the advantage that driving voltage is low, luminous efficiency is high, is function admirable
Luminous organic material.
The present invention provides a kind of triaizine compounds of class formation containing fluorenes, and general formula of molecular structure is as shown in I:
Wherein, Ar1、Ar2、Ar3It is independent to be selected from substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3
~C30One of heteroaryl, and at least one is selected from following group:
Wherein, R1、R2It is independent to be selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30's
Aryl, substituted or unsubstituted C6~C30One of heteroaryl；R3Selected from hydrogen atom, substituted or unsubstituted C1~C10's
Alkyl, substituted or unsubstituted C6~C30One of aryl.
Preferably, the Ar2、Ar3It is identical, it is selected from following group:
Wherein, R1、R2It is independent to be selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, take
Generation or unsubstituted anthryl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyrazine
One of base；R3Selected from hydrogen atom, methyl, ethyl, isopropyl, tert-butyl or pyridyl group.
Further preferably, the Ar1It does not take selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or
The anthryl in generation, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted acridinyl, substitution
Or it is unsubstituted phenoxazine base, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazine thiophene base, substituted or unsubstituted
Fluorenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted ferrosin base, replace or
Unsubstituted base, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, takes substituted or unsubstituted acenaphthenyl
Generation or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine radical, substituted or unsubstituted pyrrole
Cough up base, substituted or unsubstituted benzopyrrole base, substituted or unsubstituted triazolyl, substituted or unsubstituted thienyl, substitution
Or it unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl, substitution or does not take
One of the dibenzothiophene in generation, substituted or unsubstituted dibenzofuran group.
Most preferably, a kind of triaizine compounds of class formation containing fluorenes are any in chemical structure as follows
It is a kind of:
The present invention also provides a kind of organic luminescent device, including first electrode, second electrode and it is placed in two electrode
Between one or more organic compound layers, the organic compound layer contains a kind of described in any item class formations containing fluorenes
Triaizine compounds.
Preferably, organic compound layer includes electron transfer layer, contains one kind knot of class containing fluorenes in electron transfer layer
The triaizine compounds of structure.
Preferably, organic compound layer includes hole blocking layer, contains one kind knot of class containing fluorenes in hole blocking layer
The triaizine compounds of structure.
Beneficial effects of the present invention:
The present invention provides a kind of triaizine compounds of class formation containing fluorenes, on the one hand, triazine group especially 1,3,5- tri-
Piperazine unit structure is more stable, acid and alkali-resistance and high temperature resistant, has high glass transition temperature；Triazine group is as typical strong electrophilic
Group has high electron mobility and lower energy level using it as the compound of center structure, reconnects pyridine groups,
The electron mobility of compound is obviously improved.On the one hand, fluorenes class group is the space structure of 3 D stereo, can be effective
Intermolecular aggregation is prevented, it is made to be not easy to crystallize；Easily modification, strong rigid advantage stablize compound structure in fluorenes class group.
On the other hand, triazine group, pyridine groups, fluorenes class group combine a kind of triaizine compounds of the class formation containing fluorenes formed, three
It being connected by a phenyl ring, possesses extensible three-dimensional structure, continuous pi-conjugated system brings preferable electron mobility, thus
With high electron mobility；Also, the combination of three balances carrier transport.
Meanwhile the substituent group of fluorenes class group is alkyl substituent, especially methyl, ethyl, isopropyl or tertiary fourth in structure
Base, the dissolubility of the triaizine compounds for being added to increase the class formation containing fluorenes of alkyl；Moreover, asymmetric compound more can
Form indefinite form film.
It is applied to organic luminescent device, is used as electron transfer layer or hole blocking layer, device shows to drive
The advantage that voltage is low, luminous efficiency is high is better than existing common OLED device, when it is both electron transport material and hole barrier
When material, making devices process is convenient, saves material to save cost.What is shown in OLED luminescent device good answers
With effect, this point shows it with good industrialization prospect.
Specific embodiment:
It is clearly and completely described below in conjunction with the technical solution of the embodiment of the present invention, it is clear that described implementation
Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, art technology
Personnel's every other embodiment obtained without making creative work, belongs to protection scope of the present invention.
Alkyl of the present invention refers to alkyl made of minusing a hydrogen atom in alkane molecule, can be straight chain alkane
Base, branched alkyl, naphthenic base, example may include methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth
Base, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Aryl of the present invention refers to remove a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule after, be left the total of univalent perssad
Claiming, can be monocyclic aryl or fused ring aryl, example may include phenyl, xenyl, naphthalene, anthryl, phenanthryl or pyrenyl etc., but
It is without being limited thereto.
Heteroaryl of the present invention refers to the group that one or more aromatic core carbon in aryl are substituted by hetero atom
General name, the hetero atom include but is not limited to oxygen, sulphur or nitrogen-atoms, and the heteroaryl can be bicyclic heteroaryl or condensed ring heteroaryl
Base, example may include pyridyl group, pyrrole radicals, pyridyl group, thienyl, furyl, indyl, quinolyl, isoquinolyl, benzo thiophene
Pheno base, benzofuranyl, dibenzofuran group, dibenzothiophene, carbazyl etc., but not limited to this.
The present invention provides a kind of triaizine compounds of class formation containing fluorenes, and general formula of molecular structure is as shown in I:
Wherein, Ar1、Ar2、Ar3It is independent to be selected from substituted or unsubstituted C6~C65Aryl, substituted or unsubstituted C3
~C65One of heteroaryl, and at least one is selected from following group:
Wherein, R1、R2It is independent to be selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30's
Aryl, substituted or unsubstituted C6~C30One of heteroaryl；R3Selected from hydrogen atom, substituted or unsubstituted C1~C10's
Alkyl, substituted or unsubstituted C6~C30One of aryl.
According to the present invention, the substituted alkyl, substituted aryl, substituted heterocycle, the independent choosing of substituent group
From methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthalene, anthryl, phenanthryl, benzo phenanthryl, base, pyrenyl, benzyl, methoxy
Base, methyl mercapto, phenoxy group, thiophenyl, fluorenyl, 9,9- dimethyl fluorenyl, hexichol amido, dimethylamino, carbazyl, 9- phenyl click
Oxazolyl, furyl, thienyl, cyano, fluorine-based, deuterium base, triphenyl silicon substrate, trimethyl silicon substrate, phenothiazinyl, phenoxazine base, a word used for translation
Piperidinyl, piperidyl, pyridyl group, pyrimidine radicals, xenyl, terphenyl, nitro etc., but not limited to this.
Preferably, the Ar2、Ar3It is identical, it is selected from following group:
Wherein, R1、R2It is independent to be selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, take
Generation or unsubstituted anthryl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyrazine
One of base；R3Selected from hydrogen atom, methyl, ethyl, isopropyl, tert-butyl or pyridyl group.
Preferably, the Ar1It does not take selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or
The anthryl in generation, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted acridinyl, substitution
Or it is unsubstituted phenoxazine base, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazine thiophene base, substituted or unsubstituted
Fluorenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted ferrosin base, replace or
Unsubstituted base, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, takes substituted or unsubstituted acenaphthenyl
Generation or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine radical, substituted or unsubstituted pyrrole
Cough up base, substituted or unsubstituted benzopyrrole base, substituted or unsubstituted triazolyl, substituted or unsubstituted thienyl, substitution
Or it unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl, substitution or does not take
One of the dibenzothiophene in generation, substituted or unsubstituted dibenzofuran group.
Further preferably, the triaizine compounds of a kind of class formation containing fluorenes, it is any in chemical structure as follows
It is a kind of:
A kind of triaizine compounds of class formation containing fluorenes of the invention, specific synthetic route are as follows:
Wherein, Ar1、Ar2、Ar3It is independent to be selected from substituted or unsubstituted C6~C65Aryl, substituted or unsubstituted C3
~C65One of heteroaryl, and at least one is selected from following group:
Wherein, R1、R2It is independent to be selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30's
Aryl, substituted or unsubstituted C6~C30One of heteroaryl；R3Selected from hydrogen atom, substituted or unsubstituted C1~C10's
Alkyl, substituted or unsubstituted C6~C30One of aryl.
Above-mentioned synthesis is to be coupled to obtain target via a series of C-C for starting material with 2,4,6- tri- chloro-1,3,5-triazines
Product I, it is recommended to use Suzuki coupling reaction, under nitrogen protection, using tetra-triphenylphosphine palladium as catalyst, potassium carbonate is alkali, four
Hydrogen furans is solvent, and reflux is reacted.If intermediate has and sells, can be directly used for reacting.
The present invention does not have special limitation to coupling reaction, is using popular response well-known to those skilled in the art
Can, the preparation method is easy to operate, is readily produced.
The present invention also provides a kind of organic luminescent device, including first electrode, second electrode and it is placed in two electrode
Between one or more organic compound layers, organic compound layer include hole injection layer, hole transmission layer, electronic blocking
At least one layer of layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer；At least one in the organic compound layer
Layer includes a kind of triaizine compounds of the class formation containing fluorenes of the present invention.
Preferably, a kind of triaizine compounds of class formation containing fluorenes can be used as the electron-transport in organic luminescent device
Material.The device architecture of use is preferred specifically: NPB-DPA is used as hole injection layer substance, and NPB is used as hole transmission layer object
Matter, AND are used as main substance, and DPAVBi is used as dopant, and the triaizine compounds and Liq of a kind of class formation containing fluorenes are total
With electron-transporting material is used as, to manufacture the organic luminescent device of construction same as below: ITO/NPB-DPA/NPB/AND:
A kind of triaizine compounds of class formation containing fluorenes of DPAVBi (doping concentration 2wt%)/described: Liq/LiF/Al.It is described organic
Electroluminescent device can be used for the application fields such as flat-panel monitor, lighting source, direction board, signal lamp.
The synthesis of [embodiment 1] compound A1
The synthesis of intermediate a1-1
It takes 2- (3,5- dichloro-benzenes) pyridine (9.5g, 42.4mmol) to be added in there-necked flask, THF 100mL, nitrogen is added
Protection, -78 DEG C are stirred 30 minutes, and n-BuLi (2.5M) 21mL is then added, reacts 1 hour, adds triisopropyl borate ester
14g low-temp reaction 1 hour, is gradually recovered room temperature.Last handling process, 2M hydrochloric acid is added in system makes solution pH value 4-5, quiet
Liquid separation is set, aqueous layer with ethyl acetate extraction merges organic layer, is spin-dried for, obtains intermediate a1-1 (8.2g, yield 80%).
Mass spectrum m/z:242.86 (calculated value: 242.83).Theoretical elemental content (%) C11H11B2NO4: C, 54.41；H,
4.57；B,8.90；N,5.77；O, 26.35 actual measurement constituent content (%): C, 54.41；H,4.58；B,8.92；N,5.76；O,
26.33.The above results confirm that obtaining product is target product.
The synthesis of intermediate a1-2
Tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to intermediate a1-1
Bromo- 9, the 9- dimethyl fluorene (50.3g, 185mmol) of (44.3g, 183mmol) and 2- is molten in degassing tetrahydrofuran (500mL)
Liquid, and the mixture is heated 4 hours under reflux.It filters while hot, obtains a large amount of solids, with solvent dissolved solid, later
Concentration, obtains intermediate a1-2 (50.1g, theoretical value 70%) via silica gel column chromatography.
Mass spectrum m/z:391.25 (calculated value: 391.27).Theoretical elemental content (%) C26H22BNO2: C, 79.81；H,
5.67；B,2.76；N,3.58；O, 8.18 actual measurement constituent content (%): C, 79.82；H,5.65；B,2.76；N,3.58；O,
8.19.The above results confirm that obtaining product is target product.
The synthesis of compound A1
Tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to intermediate a1-2
(150g, 384mmol) and 2, the bromo- 6- phenyl of 4- bis- -1,3,5-triazines (41.3g, 183mmol) is in degassing tetrahydrofuran
Solution in (500mL), and the mixture is heated 4 hours under reflux.It filters while hot, obtains a large amount of solids, use solvent
Dissolved solid is concentrated later, obtains compound A1 (92.9g, theoretical value 60%) via silica gel column chromatography.
Mass spectrum m/z:848.05 (calculated value: 848.04).Theoretical elemental content (%) C61H45N5: C, 86.39；H,5.35；
N, 8.26 actual measurement constituent content (%): C, 86.37；H,5.37；N,8.26.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 2] compound A13
Change bromo- 9, the 9- dimethyl fluorene of 2- in embodiment 1 into equimolar 2- bromo- 9,9- spiral shell, two fluorenes, other steps are equal
It is identical as the synthesis of embodiment 1, obtain target product compound A13.Mass spectrum m/z:1092.26 (calculated value: 1092.29).Reason
Argument cellulose content (%) C81H49N5: C, 89.07；H,4.52；N, 6.41 actual measurement constituent content (%): C, 89.08；H,4.51；N,
6.41.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 3] compound A27
Change bromo- 9, the 9- dimethyl fluorene of 2- in embodiment 1 into bromo- 9, the 9- diphenylfluorene of equimolar 2-, 2- (3,5- bis-
Chlorobenzene) pyridine changes equimolar 3- (3,5- dichloro-benzenes) pyridine into, and other steps are identical as the synthesis of embodiment 1, obtain mesh
Mark product Compound A27.Mass spectrum m/z:1096.26 (calculated value: 1096.32).Theoretical elemental content (%) C81H53N5: C,
88.74；H,4.87；N, 6.39 actual measurement constituent content (%): C, 88.76；H,4.86；N,6.38.The above results confirmation is produced
Object is target product.
The synthesis of [embodiment 4] compound A-45 1
Change the bromo- 6- phenyl -1,3,5-triazines of 2,4- bis- in embodiment 1 into equimolar compound b, other steps are equal
It is identical as the synthesis of embodiment 1, obtain target product compound A-45 1.Mass spectrum m/z:964.26 (calculated value: 964.20).It is theoretical
Constituent content (%) C70H53N5: C, 87.20；H,5.54；N, 7.26 actual measurement constituent content (%): C, 87.21；H,5.56；N,
7.23.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 5] compound A-45 5
Change the bromo- 6- phenyl -1,3,5-triazines of 2,4- bis- in embodiment 1 into equimolar compound d, other steps are equal
It is identical as the synthesis of embodiment 1, obtain target product compound A-45 5.Mass spectrum m/z:938.06 (calculated value: 938.12).It is theoretical
Constituent content (%) C67H47N5O:C, 85.78；H,5.05；N,7.47；O, 1.71 actual measurement constituent content (%): C, 85.76；H,
5.04；N,7.47；O,1.73.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 6] compound A-28 3
Change the bromo- 6- phenyl -1,3,5-triazines of 2,4- bis- in embodiment 1 into equimolar compound e, 2- bromo- 9,9-
Dimethyl fluorene changes bromo- 9,9- spiral shell, two fluorenes of equimolar 2- into, and 2- (3,5- dichloro-benzenes) pyridine changes equimolar 3- (3,5- dichloros into
Benzene) pyridine, other steps are identical as the synthesis of embodiment 1, obtain target product compound A-28 3.Mass spectrum m/z:938.06 (meter
Calculation value: 938.12).Theoretical elemental content (%) C67H47N5O:C, 85.78；H,5.05；N,7.47；O, 1.71 actual measurement constituent contents
(%): C, 85.76；H,5.04；N,7.47；O,1.73.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 7] compound A-28 5
Tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to intermediate a1-2
(71.5g, 183mmol) and the chloro- 4- of 2- (biphenyl -4- base) -6- phenyl -1,3,5-triazines (63.6g, 185mmol) is in degassing four
Solution in hydrogen furans (500mL), and the mixture is heated 4 hours under reflux.It filters while hot, obtains a large amount of solids,
It with solvent dissolved solid, is concentrated later, obtains compound A-28 5 (71.8g, theoretical value 60%) via silica gel column chromatography.
Mass spectrum m/z:654.85 (calculated value: 654.80).Theoretical elemental content (%) C47H34N4: C, 86.21；H,5.23；
N, 8.56 actual measurement constituent content (%): C, 86.21；H,5.24；N,8.55.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 8] compound A93
The synthesis of intermediate a2-2
Tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to intermediate a1-1
Solution of bromo- 9,9- spiral shell, two fluorenes (73.1g, 185mmol) of (44.3g, 183mmol) and 2- in degassing tetrahydrofuran (500mL),
And the mixture is heated 4 hours under reflux.It filters while hot, obtains a large amount of solids, with solvent dissolved solid, Zhi Hounong
Contracting, obtains intermediate a2-2 (65.7g, theoretical value 70%) via silica gel column chromatography.
Mass spectrum m/z:513.25 (calculated value: 513.39).Theoretical elemental content (%) C36H24BNO2: C, 84.22；H,
4.71；B,2.11；N,2.73；O, 6.23 actual measurement constituent content (%): C, 84.22；H,4.71；B,2.11；N,2.74；O,
6.22.The above results confirm that obtaining product is target product.
The synthesis of compound A93
Tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to intermediate a2-2
(150g, 384mmol) and 2, the bromo- 6- phenyl of 4- bis- -1,3,5-triazines (41.3g, 183mmol) is in degassing tetrahydrofuran
Solution in (500mL), and the mixture is heated 4 hours under reflux.It filters while hot, obtains a large amount of solids, use solvent
Dissolved solid is concentrated later, obtains compound A93 (85.2g, theoretical value 60%) via silica gel column chromatography.
Mass spectrum m/z:776.95 (calculated value: 776.92).Theoretical elemental content (%) C57H36N4: C, 88.12；H,4.67；
N, 7.21 actual measurement constituent content (%): C, 88.12；H,4.66；N,7.22.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 9] compound A101
Change the bromo- 6- phenyl -1,3,5-triazines of 2,4- bis- in embodiment 1 into equimolar compound f, 2- (3,5- bis-
Chlorobenzene) pyridine changes equimolar 3- (3,5- dichloro-benzenes) pyridine into, and other steps are identical as the synthesis of embodiment 1, obtain mesh
Mark product Compound A101.Mass spectrum m/z:743.86 (calculated value: 743.89).Theoretical elemental content (%) C53H37N5: C,
85.57；H,5.01；N, 9.41 actual measurement constituent content (%): C, 85.59；H,5.00；N,9.41.The above results confirmation is produced
Object is target product.
[comparison Application Example]
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and exposure 30 minutes under ultraviolet light,
Then handled 10 minutes with plasma.Then by treated, ito substrate is put into evaporated device.It is deposited one layer of 60nm's first
The NPB of 20nm is deposited as hole transmission layer, vapor deposition as hole injection layer, evaporation rate 0.1nm/s in NPB-DPA later
Speed is 0.1nm/s, followed by ADN/DPAVBi, doping concentration 2wt%, host material is deposited in the vapor deposition of luminescent layer, mixing
Evaporation rate be 0.1nm/s, dopant material evaporation rate is 0.002nm/s, evaporation thickness 35nm, and 30nm is then deposited
Alq3As electron transfer layer, evaporation rate 0.1nm/s, successively vacuum evaporation LiF and Al is used as yin on the electron transport layer
Pole, with a thickness of 200nm.
[Application Example 1]
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and exposure 30 minutes under ultraviolet light,
Then handled 10 minutes with plasma.Then by treated, ito substrate is put into evaporated device.It is deposited one layer of 60nm's first
The NPB of 20nm is deposited as hole transmission layer, vapor deposition as hole injection layer, evaporation rate 0.1nm/s in NPB-DPA later
Speed is 0.1nm/s, followed by ADN/DPAVBi, doping concentration 2wt%, host material is deposited in the vapor deposition of luminescent layer, mixing
Evaporation rate be 0.1nm/s, dopant material evaporation rate is 0.002nm/s, evaporation thickness 35nm, and 30nm is then deposited
Compound A1 is as electron transfer layer, and evaporation rate 0.05nm/s, successively vacuum evaporation LiF and Al makees on the electron transport layer
For cathode, with a thickness of 200nm.
[Application Example 2]
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and exposure 30 minutes under ultraviolet light,
Then handled 10 minutes with plasma.Then by treated, ito substrate is put into evaporated device.It is deposited one layer of 60nm's first
The NPB of 20nm is deposited as hole transmission layer, vapor deposition as hole injection layer, evaporation rate 0.1nm/s in NPB-DPA later
Speed is 0.1nm/s, followed by ADN/DPAVBi, doping concentration 2wt%, host material is deposited in the vapor deposition of luminescent layer, mixing
Evaporation rate be 0.1nm/s, dopant material evaporation rate is 0.002nm/s, evaporation thickness 35nm, and 30nm is then deposited
Compound A1 and Liq coevaporation (50:50wt%) is used as electron transfer layer, evaporation rate 0.05nm/s, in electron transfer layer
On successively vacuum evaporation LiF and Al is as cathode, with a thickness of 200nm.
[Application Example 3]
It changes the electron transfer layer in Application Example 2 into compound B-11 and Liq is co-evaporated.
[Application Example 4]
The electron transfer layer in Application Example 2 is changed into compound B23 and Liq to co-evaporate.
[Application Example 5]
The electron transfer layer in Application Example 2 is changed into compound B27 and Liq to co-evaporate.
[Application Example 6]
The electron transfer layer in Application Example 2 is changed into compound D1 and Liq to co-evaporate.
[Application Example 7]
The electron transfer layer in Application Example 2 is changed into compound D7 and Liq to co-evaporate.
[Application Example 8]
The electron transfer layer in Application Example 2 is changed into compound D20 and Liq to co-evaporate.
[Application Example 9]
The electron transfer layer in Application Example 2 is changed into compound D23 and Liq to co-evaporate.
[Application Example 10]
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and exposure 30 minutes under ultraviolet light,
Then handled 10 minutes with plasma.Then by treated, ito substrate is put into evaporated device.It is deposited one layer of 60nm's first
The NPB of 20nm is deposited as hole transmission layer, vapor deposition as hole injection layer, evaporation rate 0.1nm/s in NPB-DPA later
Speed is 0.1nm/s, followed by ADN/DPAVBi, doping concentration 2wt%, host material is deposited in the vapor deposition of luminescent layer, mixing
Evaporation rate be 0.1nm/s, dopant material evaporation rate is 0.002nm/s, evaporation thickness 35nm, and 30nm is then deposited
Alq is as electron transfer layer, evaporation rate 0.05nm/s, then the compound A1 of 10nm is deposited as hole blocking layer, in sky
Successively vacuum evaporation LiF and Al is as cathode on the barrier layer of cave, with a thickness of 200nm.
[Application Example 11]
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and exposure 30 minutes under ultraviolet light,
Then handled 10 minutes with plasma.Then by treated, ito substrate is put into evaporated device.It is deposited one layer of 60nm's first
The NPB of 20nm is deposited as hole transmission layer, vapor deposition as hole injection layer, evaporation rate 0.1nm/s in NPB-DPA later
Speed is 0.1nm/s, followed by ADN/DPAVBi, doping concentration 2wt%, host material is deposited in the vapor deposition of luminescent layer, mixing
Evaporation rate be 0.1nm/s, dopant material evaporation rate is 0.002nm/s, evaporation thickness 35nm, and 30nm is then deposited
Compound A1 is as electron transfer layer and hole blocking layer, evaporation rate 0.05nm/s, in electron transfer layer and hole barrier
Successively vacuum evaporation LiF and Al is as cathode on layer, with a thickness of 200nm.
[Application Example 12]
By in Application Example 11 electron transfer layer and hole blocking layer change compound B-11 into.
[Application Example 13]
Change the electron transfer layer in Application Example 11 into compound B23.
[Application Example 14]
Change the electron transfer layer in Application Example 11 into compound B27.
[Application Example 15]
Change the electron transfer layer in Application Example 11 into compound D1.
[Application Example 16]
Change the electron transfer layer in Application Example 11 into compound D7.
[Application Example 17]
Change the electron transfer layer in Application Example 11 into compound D20.
[Application Example 18]
Change the electron transfer layer in Application Example 11 into compound D23.
The electron luminescence characteristic of the organic luminescent device of above method manufacture indicates in the following table:
The above result shows that a kind of triaizine compounds of class formation containing fluorenes of the invention are applied in organic luminescent device,
It can be used as electron transport layer materials, hole barrier layer material or be both electron transfer layer and hole blocking layer, show
The advantage that driving voltage is low, luminous efficiency is high is luminous organic material of good performance.
Obviously, the above description of the embodiment is only used to help understand the method for the present invention and its core ideas.It should refer to
It out, without departing from the principle of the present invention, can also be to this hair for the those of ordinary skill of the technical field
Bright some improvement and modification can also be carried out, and these improvements and modifications also fall within the scope of protection of the claims of the present invention.
Claims (7)
1. a kind of triaizine compounds of class formation containing fluorenes, which is characterized in that its general formula of molecular structure is as shown in I:
Wherein, Ar1、Ar2、Ar3It is independent to be selected from substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30
One of heteroaryl, and at least one is selected from following group:
Wherein, R1、R2It is independent to be selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl,
Substituted or unsubstituted C6~C30One of heteroaryl；R3Selected from hydrogen atom, substituted or unsubstituted C1~C10Alkyl,
Substituted or unsubstituted C6~C30One of aryl.
2. a kind of triaizine compounds of class formation containing fluorenes according to claim 1, which is characterized in that Ar2、Ar3It is identical, choosing
From following group:
Wherein, R1、R2It is independent selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or
Unsubstituted anthryl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, in substituted or unsubstituted pyrazinyl
One kind；R3Selected from hydrogen atom, methyl, ethyl, isopropyl, tert-butyl or pyridyl group.
3. a kind of triaizine compounds of class formation containing fluorenes according to claim 1, which is characterized in that Ar1Selected from substitution or not
Substituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substitution or not
Substituted triphenylene, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazine base, substituted or unsubstituted pheno thiophene
Piperazine base, substituted or unsubstituted phenoxazine thiophene base, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazyl, substitution or not
Substituted pyrenyl, substituted or unsubstituted ferrosin base, substituted or unsubstituted base, substituted or unsubstituted acenaphthenyl, substitution
Or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazine
Base, substituted or unsubstituted triazine radical, substituted or unsubstituted pyrrole radicals, substituted or unsubstituted benzopyrrole base, replace or
Unsubstituted triazolyl, substituted or unsubstituted thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzo thiophene
Pheno base, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzo
One of furyl.
4. a kind of triaizine compounds of class formation containing fluorenes according to claim 1, which is characterized in that be selected from as followsization
Learn any one in structure:
5. a kind of organic luminescent device, which is characterized in that the organic luminescent device include cathode, anode and be placed in it is described two electricity
One or more organic compound layers between pole, it is described in any item that the organic compound layer contains Claims 1 to 4
A kind of triaizine compounds of the class formation containing fluorenes.
6. a kind of organic luminescent device according to claim 5, which is characterized in that the organic compound layer includes electricity
Sub- transport layer contains a kind of described in any item triaizine compounds of the class formation containing fluorenes of Claims 1 to 4 in electron transfer layer.
7. a kind of organic luminescent device according to claim 6, which is characterized in that the organic compound layer includes sky
A kind of described in any item triaizine compounds of the class formation containing fluorenes of Claims 1 to 4 are contained in hole blocking layer in cave barrier layer.
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| CN111233832A (en) * | 2020-01-08 | 2020-06-05 | 上海传勤新材料有限公司 | Organic electronic material containing fluorene and triazine and application thereof |
| CN111747951A (en) * | 2020-05-30 | 2020-10-09 | 浙江华显光电科技有限公司 | Triazine compound and organic light-emitting device thereof |
| CN113227078A (en) * | 2018-12-21 | 2021-08-06 | 斗山索如始株式会社 | Organic light-emitting compound and organic electroluminescent element using same |
| CN113402498A (en) * | 2021-08-19 | 2021-09-17 | 浙江华显光电科技有限公司 | Spirobifluorene compound, preparation, organic light-emitting device, and display or lighting device |
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