CN108365127A - A kind of organic semiconductive material and its organic luminescent device - Google Patents
A kind of organic semiconductive material and its organic luminescent device Download PDFInfo
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- CN108365127A CN108365127A CN201810148747.XA CN201810148747A CN108365127A CN 108365127 A CN108365127 A CN 108365127A CN 201810148747 A CN201810148747 A CN 201810148747A CN 108365127 A CN108365127 A CN 108365127A
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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Abstract
A kind of organic semiconductive material of present invention offer and its organic luminescent device, are related to organic optoelectronic materials technology.The present invention obtains a kind of organic semiconductive material by adulterating axis vinyl compound in arylamine class host material, it has stronger electric conductivity and cavity transmission ability, thermal stability good, it synthesizes simple to operation, it can be applied to be used as hole transmission layer in organic luminescent device, it can effectively solve the problems, such as that carrier transport is uneven in organic luminescent device, device stability is poor and short life, its organic luminescent device has the advantages of luminous efficiency is high, long lifespan.
Description
Technical field
The present invention relates to organic photoelectrical material technical field more particularly to a kind of organic semiconductive materials and its organic hair
Optical device.
Background technology
In recent years, Organic Light Emitting Diode (OLED:Organic Light Emitting Diode) as a kind of novel
The visual field of people is progressed into promising display technology.It is compared with traditional display technology, in voltage characteristic, luminance
Degree, luminous efficiency, device weight, response speed and appreciative perspective etc. have significant advantage, and because of its low cost potential,
As panel display technologies most potential at present, possess broad mass market foreground.
In general, it is to generally comprise cathode, sun that OLED, which uses stratiform or laminar structure, its structure of typical organic luminescent device,
Pole and the organic matter layer between electrode.Organic photoelectrical material used in organic matter layer applied to OLED device is from purposes
Two class materials can be roughly divided into：Charge injects and transport layer, luminescent material.Wherein, charge injection transmission material is divided into hole note
Enter material, hole mobile material, electron injection material, electron transport material, effect is mainly equilbrium carrier injection so that
Electronics is effectively combined to form exciton with hole in luminescent layer, and then is shone, and luminous efficiency is improved.
Currently, the research of electroluminescent organic material is carried out in academia and industrial quarters extensively, a large amount of function admirables
Electroluminescent organic material be developed successively, all in all, the direction of the following OLED be development high efficiency, high brightness,
Long-life, inexpensive white light parts and full color display device, but the technological industrialization process still faces many keys and asks
How topic improves carrier mobility rate, equilbrium carrier injection, and then improves luminous efficiency；Reduce carrier transport process
In non-radiative energy dissipate, improve device stability, extending device service life etc. becomes urgent problem to be solved.
Invention content
The object of the present invention is to provide a kind of organic semiconductive material and its organic luminescent device, provided by the invention one
Kind organic semiconductive material has good hole transport performance, and synthetic method is simple to operation, uses the organic semiconductive
Property material preparation organic luminescent device there is good luminous efficiency and service life to show.
The present invention provides a kind of organic semiconductive material, the organic semiconductive material contains host material and mixes
Miscellaneous material, wherein dopant material are Radialene compounds, and molecular structural formula is as shown in chemical formula I：
Wherein, R1、R2、R3Independently selected from cyano, the heterocycle of the aryl of substituted C6~C60, substituted C3~C60
In one kind, wherein any one of substituent group in cyano, halogen, trifluoromethyl；
Wherein, the host material of the organic semiconductive material has structure shown in chemical formula II：
Wherein, Ar1、Ar2、Ar3、Ar4Independent aryl selected from substituted or unsubstituted C6~C60, substitution or unsubstituted
C3~C60 heterocycle in one kind；L be selected from the aryl of substituted or unsubstituted C6~C60, substituted or unsubstituted C3~
One kind in the heterocycle of C60.
Preferably, wherein R1、R2、R3Independently selected from cyano, the aryl of substituted C6~C30, substituted C3~C30
Any one of one kind in heterocycle, wherein substituent group in cyano, halogen, trifluoromethyl.
Further preferably, wherein R1, R2, R3 independently selected from cyano, substituted phenyl, substituted naphthalene, substituted pyridyl group,
Substituted pyrimidine radicals, substituted triazine radical, substituted pyrrole radicals, substituted thiazolyl, substituted imidazole radicals, substituted furans
One kind in base, substituted thienyl, substituted quinolyl, substituted indyl, wherein substituent group be selected from cyano, halogen or
One kind in trifluoromethyl.
Preferably, a kind of organic semiconductive material of the present invention, wherein the host material chemical formula such as chemistry
Shown in formula III：
Wherein, Ar1、Ar2、Ar3Independent aryl, substituted or unsubstituted C3 selected from substituted or unsubstituted C6~C60
One kind in the heterocycle of~C60；L is selected from aryl, the substituted or unsubstituted C3~C60 of substituted or unsubstituted C6~C60
Heterocycle in one kind；X is selected from CR5R6、O、NR7、S、P(O)R8、SO2、SiR9R10In one kind；R4、R5、R6、R7、R8、R9、
R10Independently selected from hydrogen, the alkyl of substituted or unsubstituted C1~C30, substituted or unsubstituted C6~C30 aryl, substitution or
One kind in the heterocycle of unsubstituted C3~C30 or R4SubstitutionTwo neighboring carbon atom cyclization on group.
Preferably, Ar1、Ar2、Ar3It is independent aryl selected from substituted or unsubstituted C6~C30, substituted or unsubstituted
One kind in the heterocycle of C3~C30；L be selected from the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~
One kind in the heterocycle of C30；X is selected from CR5R6、O、NR7、S、SiR9R10In one kind；R4、R5、R6、R7、R9、R10Independently select
From hydrogen, the alkyl of substituted or unsubstituted C1~C30, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3
One kind in the heterocycle of~C30.
Further preferably, the Ar1、Ar2、Ar3Independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene,
Substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene
It is base, substituted or unsubstitutedIt is base, substituted or unsubstituted base, substituted or unsubstituted fluoranthene base, substituted or unsubstituted
Indenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl group, substitution do not take
The pyrimidine radicals in generation, substituted or unsubstituted dibenzo Silole base, substituted or unsubstituted dibenzofuran group, substitution
Or unsubstituted dibenzothiophene, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substitution or unsubstituted
Quinolyl, substituted or unsubstituted indyl, substituted or unsubstituted phenoxazine base, substituted or unsubstituted phenothiazinyl,
One kind in substituted or unsubstituted phenoxazine thiophene base；
L be selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substitution or
Unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, takes substituted or unsubstituted base
In generation, is unsubstitutedBase, substituted or unsubstituted fluoranthene base, substituted or unsubstituted indenyl, substituted or unsubstituted carbazole
One kind in base, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzo Silole base；
R4、R5、R6、R7、R8、R9、R10It is independent selected from methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, substitution or
Unsubstituted phenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted triazine radical,
One kind in substituted or unsubstituted furyl, substituted or unsubstituted thienyl.
Most preferably, a kind of dopant material of organic semiconductive material of the present invention is arbitrary in such as lower structure
It is a kind of：
Most preferably, a kind of host material of organic semiconductive material of the present invention is arbitrary in such as lower structure
It is a kind of：
The present invention also provides a kind of organic luminescent device, the organic luminescent device includes cathode, anode successively and sets
In organic matter layer between the two；At least one layer of organic semiconductive for containing doping of the present invention in the organic matter layer
Material.
Preferably, organic matter layer of the present invention includes hole transmission layer, and institute of the present invention is contained in the hole transmission layer
The organic semiconductive material for any doping stated.
Beneficial effects of the present invention：
A kind of organic semiconductive material of present invention offer and its organic luminescent device.The present invention with hole by passing
Axis vinyl compound is adulterated in the arylamine class formation of defeated performance, axis vinyl compound of the present invention has cyano, halogen, three
The electron accepting groups such as the aryl and heterocycle of methyl fluoride substitution, itself has stronger electron affinity, these electron acceptors
Molecule generates so-called hole by the electron transmission in arylamine class host material, realizes the generation and transmission in hole, improves
Quantity and transmission rate of the hole in host material, to a kind of organic semiconductive material after doping of the present invention
Material has good electric conductivity and hole transport performance.
Since doped organic semiconductive material of the present invention has good hole transport performance, using this
Organic luminescent device prepared by invention semiconductive material, hole mobility are high, carrier luminescent layer compound quantity and
Recombination probability improves, to have higher luminous efficiency.
Since doped organic semiconductive materials of the present invention have good electric conductivity, can effectively avoid it has
The reduction and loss of carrier and unnecessary energy dissipation in machine luminescent device, to improve stability and the use of device
Service life.
There is good shine using a kind of organic luminescent device of organic semiconductive material preparation of the present invention
Efficiency and service life performance.
Specific implementation mode：
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
The every other embodiment that personnel are 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 refer to aromatic hydrocarbon molecule aromatic core carbon on remove a hydrogen atom after, be left univalent perssad it is total
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.
Heterocycle of the present invention is the alicyclic heterocyclic being made of carbon and hetero atom or removes a hydrogen on the core carbon of heteroaromatic
Atom is left the general name of univalent perssad, and the hetero atom includes but not limited to oxygen, sulphur, nitrogen-atoms, and the heterocycle can be single
Ring heterocycle or fused ring heterocycle base, example may include thienyl, furanylpyridinyl, pyrrole radicals, pyridyl group, thienyl, furans
Base, indyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, dibenzofuran group, dibenzothiophene, click
Oxazolyl etc., but not limited to this.
The present invention provides a kind of organic semiconductive materials, which contains host material and dopant material, wherein mixing
Miscellaneous material is Radialene compounds, and molecular structural formula is as shown in chemical formula I：
Wherein, R1、R2、R3Independently selected from cyano, the heterocycle of the aryl of substituted C6~C60, substituted C3~C60
In one kind, wherein any one of substituent group in cyano, halogen, trifluoromethyl；
Wherein, the host material of the organic semiconductive material has structure shown in chemical formula II：
Wherein, Ar1、Ar2、Ar3、Ar4Independent aryl selected from substituted or unsubstituted C6~C60, substitution or unsubstituted
C3~C60 heterocycle in one kind；L be selected from the aryl of substituted or unsubstituted C6~C60, substituted or unsubstituted C3~
One kind in the heterocycle of C60.
Preferably, R1、R2、R3Independently selected from cyano, the heterocycle of the aryl of substituted C6~C30, substituted C3~C30
Any one of one kind in base, wherein substituent group in cyano, halogen, trifluoromethyl.
Preferably, wherein R1, R2, R3 independently selected from cyano, substituted phenyl, substituted naphthalene, substituted pyridyl group,
Substituted pyrimidine radicals, substituted triazine radical, substituted pyrrole radicals, substituted thiazolyl, substituted imidazole radicals, substituted furans
One kind in base, substituted thienyl, substituted quinolyl, substituted indyl, wherein substituent group be selected from cyano, halogen or
One kind in trifluoromethyl.
Preferably, a kind of organic semiconductive material of the present invention, wherein the host material chemical formula such as chemistry
Shown in formula III：
Wherein, Ar1、Ar2、Ar3Independent aryl, substituted or unsubstituted C3 selected from substituted or unsubstituted C6~C60
One kind in the heterocycle of~C60；L is selected from aryl, the substituted or unsubstituted C3~C60 of substituted or unsubstituted C6~C60
Heterocycle in one kind；X is selected from CR5R6、O、NR7、S、P(O)R8、SO2、SiR9R10In one kind；R4、R5、R6、R7、R8、R9、
R10Independently selected from hydrogen, the alkyl of substituted or unsubstituted C1~C30, substituted or unsubstituted C6~C30 aryl, substitution or
One kind in the heterocycle of unsubstituted C3~C30.
Wherein, R4Can directly it replaceHydrogen on group carbon atom, can also be withOn group
Two neighboring carbon atom cyclization.
Preferably, Ar1、Ar2、Ar3It is independent aryl selected from substituted or unsubstituted C6~C30, substituted or unsubstituted
One kind in the heterocycle of C3~C30；L is selected from aryl, the substituted or unsubstituted C3-C30 of substituted or unsubstituted C6-C30
Heterocycle in one kind；X is selected from CR5R6、O、NR7、S、SiR9R10In one kind；R4、R5、R6、R7、R9、R10Independently selected from
Hydrogen, the alkyl of substituted or unsubstituted C1~C30, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~
One kind in the heterocycle of C30.
Further preferably, the Ar1、Ar2、Ar3Independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene,
Substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene
It is base, substituted or unsubstitutedIt is base, substituted or unsubstituted base, substituted or unsubstituted fluoranthene base, substituted or unsubstituted
Indenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl group, substitution do not take
The pyrimidine radicals in generation, substituted or unsubstituted dibenzo Silole base, substituted or unsubstituted dibenzofuran group, substitution
Or unsubstituted dibenzothiophene, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substitution or unsubstituted
Quinolyl, substituted or unsubstituted indyl, substituted or unsubstituted phenoxazine base, substituted or unsubstituted phenothiazinyl,
One kind in substituted or unsubstituted phenoxazine thiophene base；
L be selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substitution or
Unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, takes substituted or unsubstituted base
In generation, is unsubstitutedBase, substituted or unsubstituted fluoranthene base, substituted or unsubstituted indenyl, substituted or unsubstituted carbazole
One kind in base, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzo Silole base；
R4、R5、R6、R7、R8、R9、R10It is independent selected from methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, substitution or
Unsubstituted phenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted triazine radical,
One kind in substituted or unsubstituted furyl, substituted or unsubstituted thienyl.
Most preferably, as an example, it is not particularly limited, a kind of doping material of organic semiconductive material of the present invention
Any one of material in such as lower structure：
Most preferably, as an example, it is not particularly limited, a kind of matrix material of organic semiconductive material of the present invention
Any one of material in such as lower structure：
A kind of dopant material of organic semiconductive material of the present invention, synthetic route are as follows：
Wherein, R1、R2、R3Independently selected from cyano, the heterocycle of the aryl of substituted C6~C60, substituted C3~C60
In one kind, wherein any one of substituent group in cyano, halogen, trifluoromethyl.
A kind of host material of organic semiconductive material of the present invention, synthetic route are as follows：
Wherein, Ar1、Ar2、Ar3、Ar4Independent aryl selected from substituted or unsubstituted C6~C60, substitution or unsubstituted
C3~C60 heterocycle in one kind；L be selected from the aryl of substituted or unsubstituted C6~C60, substituted or unsubstituted C3~
One kind in the heterocycle of C60.
The present invention limitation not special to above-mentioned reaction be using popular response well-known to those skilled in the art
Can, the preparation method is simple, easily operated.
The present invention also provides a kind of organic luminescent device, the organic luminescent device includes cathode, anode successively and sets
In organic matter layer between the two；At least one layer of organic semiconductive for containing doping of the present invention in the organic matter layer
Material.
Preferably, organic matter layer of the present invention includes hole transmission layer, and institute of the present invention is contained in the hole transmission layer
The organic semiconductive material for any doping stated.
OLED structure of the present invention is：ITO is as transparent anode；It is of the present invention organic partly to lead
Electric material compound is as hole transmission layer；BND/Firpic is used as luminescent layer substance；Alq3As electron transfer layer；Al is used
Make cathode.
Organic semiconductive material of the present invention is used as hole mobile material, to manufacture construction same as below
Organic luminescent device：ITO/ organic semiconductive material (70nm)/BND of the present invention：Firpic(30nm)/Alq3
(50nm)/Al(200nm)。
Organic luminescent device of the present invention can be widely applied to Display panel, lighting source, flexibility OLED, Electronic Paper,
The fields such as Organophotoreceptor or Organic Thin Film Transistors, direction board, signal lamp.
The synthesis of [embodiment 1] compound 1-1
Step1：Phenyl-hexafluoride (1.86g, 10mmol), ethyl cyanoacetate (1.11g, 10mmol), carbonic acid are added in reactor
The DMF of potassium (1.67g, 12.1mmol), 30mL, is stirred to react 48h at room temperature, rear that distilled water and acetic acid termination reaction is added, and uses
Dichloromethane extracts and is concentrated to give intermediate 1-1-1 (2.76g, 99%).
Step2：Intermediate 1-1-1 (2.79g, 10mmol), 50% acetic acid (4.10mL) and sulfuric acid are added in reactor
(0.2mL), flow back 16h after stir, be cooled to room temperature in mixture, be added dropwise 10mL cold distilled waters terminate reaction, stir 0.5h afterwards,
Reaction mixture distilled water and chloroform are extracted, intermediate 1-1-2 (1.99g, 96%) is then concentrated to give.
Step3：2,5- dichloros benzoquinone (0.88g, 5mmol), intermediate 1- is added in the reactor under the conditions of 0 DEG C
1-2 (2.07g, 10mmol), 30mL tetrahydrofurans, potassium tert-butoxide (1.82g, 16.2mmol) react 6h, and temperature is warmed to room temperature,
It is handled with distilled water and dichloromethane, carries out column chromatography with dichloromethane and hexane afterwards, obtain intermediate 1-1-3
(2.49g, 48%).
Step4：Intermediate 1-1-3 (5.18g, 10mmol), the third dicyan (2.14g, 32.4mmol), two are added in reactor
TiCl is slowly added dropwise at -78 DEG C in chloromethanes 400mL4(6.15g, 32.4mmol), pyridine (64.8mmol).Then in room temperature
Distilled water is added dropwise under condition of ice bath and terminates reaction, is then handled with distilled water and dichloromethane, is then used by lower stirring 12h
Dichloromethane and hexane carry out column chromatography, obtain compound 1-1 (2.76g, 45%).
The synthesis of [embodiment 2] compound 1-2
Compound 1-2 (3.36g, 47%) is obtained according to the synthetic method of compound 1-1.
The synthesis of [embodiment 3] compound 1-5
Compound 1-5 (3.02g, 48%) is obtained according to the synthetic method of compound 1-1.
The synthesis of [embodiment 4] compound 1-27
Compound 1-27 (3.31g, 40%) is obtained according to the synthetic method of compound 1-1.
The synthesis of [embodiment 5] compound 2-7
Step1：In reactor be added aniline (0.75g, 8mmol), the bromo- dibenzofurans of 2- (1.65g, 6.67mmol),
Pd2(dba)3(0.17g, 0.2mmol), P (t-Bu)3(0.14,0.67mmol), NaOt-Bu (2.24g, 20mmol), toluene are molten
Liquid 100mL reacts 8h under the conditions of 100 DEG C, ether and water is used to extract organic phase, organic layer MgSO after reaction4It is dry, it is dense
Contracting organic matter crosses column chromatography, is recrystallized to give intermediate 2-7-1 (1.56g, 90%).
Step2：In reactor be added 4- aminobphenyls (1.35g, 8mmol), 4- bromobiphenyls (1.55g, 6.67mmol),
Pd2(dba)3(0.17g, 0.2mmol), P (t-Bu)3(0.14,0.67mmol), NaOt-Bu (2.24g, 20mmol), toluene are molten
Liquid 100mL reacts 5h under the conditions of 80 DEG C, ether and water is used to extract organic phase, organic layer MgSO after reaction4It is dry, it is dense
Contracting organic matter crosses column chromatography, is recrystallized to give intermediate 2-7-2 (2.08g, 97%).
Step3：Be added 4,4 '-two bromo- 1 in reactor, 1 '-biphenyl (2.5g, 8mmol), intermediate 2-7-1 (1.73g,
6.67mmol)、Pd2(dba)3(0.17g, 0.2mmol), P (t-Bu)3(0.14,0.67mmol), NaOt-Bu (2.24g,
20mmol), toluene solution 100mL reacts 8h under the conditions of 100 DEG C, and ether and water is used to extract organic phase, organic layer after reaction
Use MgSO4Dry, condensed organic crosses column chromatography, is recrystallized to give intermediate 2-7-3 (2.36g, 72%).
Step4：Intermediate 2-7-2 (2.57g, 8mmol), 2-7-3 (3.27g, 6.67mmol), Pd are added in reactor2
(dba)3(0.17g, 0.2mmol), P (t-Bu)3(0.14,0.67mmol), NaOt-Bu (2.24g, 20mmol), toluene solution
100mL reacts 8h under the conditions of 100 DEG C, and ether and water is used to extract organic phase, organic layer MgSO after reaction4It is dry, concentration
Organic matter crosses column chromatography, is recrystallized to give compound 2-7 (3.17g, 65%).
The synthesis of [embodiment 6] compound 2-41
Compound 2-41 (3.56g, 64%) is obtained according to the synthetic method of compound 2-7.
The synthesis of [embodiment 7] compound 2-49
Compound 2-49 (3.38g, 58%) is obtained according to the synthetic method of compound 2-7.
The synthesis of [embodiment 8] compound 2-61
Compound 2-61 (3.6g, 67%) is obtained according to the synthetic method of compound 2-7.
The FD-MS values of the organic semiconductive material of synthesis of the embodiment of the present invention are as shown in table 1：
【Table 1】
| Embodiment | FD-MS |
| Embodiment 1 | M/z=614.16 (C28H4F10N6=614.03) |
| Embodiment 2 | M/z=714.21 (C30H4F14N6=714.03) |
| Embodiment 3 | M/z=628.10 (C30H4F8N8=628.04) |
| Embodiment 4 | M/z=828.13 (C34H4F16N8=828.03) |
| Embodiment 5 | M/z=730.19 (C54H38N2O=730.30) |
| Embodiment 6 | M/z=832.35 (C63H48N2=832.38) |
| Embodiment 7 | M/z=873.22 (C66H52N2=873.16) |
| Embodiment 8 | M/z=805.29 (C60H43N3=805.35) |
[comparative example 1] device prepares embodiment：
Ito glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleans
Ultrasonic washing is later dry in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base
Plate washs 5 minutes, is sent in evaporator.
Successively hole transmission layer NPB/70nm, vapor deposition main body BND on the ito transparent electrode being already prepared to：Doping
Firpic10% mixing/30nm and then vapor deposition electron transfer layer Alq3/ 30nm, cathode Al/200nm.
[embodiment 9] device prepares embodiment：
Ito glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleans
Ultrasonic washing is later dry in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base
Plate washs 5 minutes, is sent in evaporator.
Following each organic matter layer is successively deposited on the ito transparent electrode being already prepared to：Hole transmission layer compound 1-
1:2-7 (10mol%：90mol%)/30nm, vapor deposition main body BND：Adulterate 10% mixing of Firpic/30nm, electron transfer layer
Alq3/ 30nm, cathode Al/200nm.
[embodiment 10] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 1-1:2-41 (10mol%：
90mol%).
[embodiment 11] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 1-1:2-49 (10mol%：
90mol%).
[embodiment 12] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 1-1:2-61 (10mol%：
90mol%).
[embodiment 13] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 1-2:2-7 (10mol%：
90mol%).
[embodiment 14] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 1-2:2-41 (10mol%：
90mol%).
[embodiment 15] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 1-2:2-49 (10mol%：
90mol%).
[embodiment 16] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 1-2:2-61 (10mol%：
90mol%).
[embodiment 17] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 1-5:2-7 (10mol%：
90mol%)
[embodiment 18] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 1-5:2-41 (10mol%：
90mol%).
[embodiment 19] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 1-5:2-49 (10mol%：
90mol%).
[embodiment 20] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 1-5:2-61 (10mol%：
90mol%).
[embodiment 21] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 1-27:2-7 (10mol%：
90mol%).
[embodiment 22] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 1-27:2-41 (10mol%：
90mol%).
[embodiment 23] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 1-27:2-49 (10mol%：
90mol%).
[embodiment 24] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 1-27:2-61 (10mol%：
90mol%).
[embodiment 25] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 2-7.
[embodiment 26] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 2-41.
[embodiment 27] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 2-49.
[embodiment 28] device prepares embodiment：
By the hole transmission layer 1-1 of embodiment 9:2-7 (10mol%：90mol%) it is changed to 2-61.
The characteristics of luminescence test result such as table 2 of luminescent device prepared by 9-24 of the embodiment of the present invention and comparative example 1
It is shown.
[table 2]
The above result shows that a kind of organic semiconductive material of the invention is applied in organic luminescent device, especially
As hole transmission layer, the luminous efficiency of organic electro-luminance device and service life are significantly increased, organic semiconductive of the invention
Material is luminous organic material of good performance, and the host material of the organic semiconductive material of the present invention is separately as sky
Hole transport materials can also improve the luminous efficiency and service life of device to a certain extent.
It should be pointed out that the present invention is particularly described with individual embodiments, but before not departing from the principle of the invention
It puts, ordinary skill people can carry out the present invention improvement on various forms or details, these improvement also fall into this hair
In bright protection domain.
Claims (10)
1. a kind of organic semiconductive material, which is characterized in that the material contains host material and dopant material, wherein adulterating material
Material is Radialene compounds, and molecular structural formula is as shown in chemical formula I：
Wherein, R1、R2、R3Independently selected from cyano, the aryl of substituted C6~C60, substituted C3~C60 heterocycle in
Any one of one kind, wherein substituent group in cyano, halogen, trifluoromethyl；
Wherein, the host material of the organic semiconductive material has structure shown in chemical formula II：
Wherein, Ar1、Ar2、Ar3、Ar4Independent aryl, substituted or unsubstituted C3 selected from substituted or unsubstituted C6~C60
One kind in the heterocycle of~C60；L is selected from aryl, the substituted or unsubstituted C3~C60 of substituted or unsubstituted C6~C60
Heterocycle in one kind.
2. a kind of organic semiconductive material according to claim 1, which is characterized in that R1、R2、R3Independently selected from cyanogen
Base, the aryl of substituted C6~C30, substituted C3~C30 heterocycle in one kind, wherein substituent group be selected from cyano, halogen,
Any one in trifluoromethyl.
3. a kind of organic semiconductive material according to claim 1, which is characterized in that wherein R1、R2、R3Independently select
From cyano, substituted phenyl, substituted naphthalene, substituted pyridyl group, substituted pyrimidine radicals, substituted triazine radical, substituted pyrrole
Cough up base, substituted thiazolyl, substituted imidazole radicals, substituted furyl, substituted thienyl, substituted quinolyl, substitution
One kind in indyl, wherein the one kind of substituent group in cyano, halogen or trifluoromethyl.
4. a kind of organic semiconductive material according to claim 1, wherein the host material chemical formula such as chemical formula
Shown in III：
Wherein, Ar1、Ar2、Ar3Independent aryl selected from substituted or unsubstituted C6~C60, substituted or unsubstituted C3~
One kind in the heterocycle of C60；L is selected from the aryl of substituted or unsubstituted C6~C60, substituted or unsubstituted C3~C60
One kind in heterocycle；X is selected from CR5R6、O、NR7、S、P(O)R8、SO2、SiR9R10；R4、R5、R6、R7、R8、R9、R10Independently select
From hydrogen, the alkyl of substituted or unsubstituted C1~C30, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3
One kind in the heterocycle of~C30 or R4SubstitutionTwo neighboring carbon atom cyclization on group.
5. according to a kind of organic semiconductive material described in claim 4, Ar1、Ar2、Ar3It is independent selected from substitution or not
The aryl of substituted C6~C30, substituted or unsubstituted C3~C30 heterocycle in one kind；L is selected from substituted or unsubstituted
The aryl of C6~C30, substituted or unsubstituted C3~C30 heterocycle in one kind；X is selected from CR5R6、O、NR7、S、SiR9R10
In one kind；R4、R5、R6、R7、R9、R10It does not take independently selected from hydrogen, the alkyl of substituted or unsubstituted C1~C30, substitution or
The aryl of the C6~C30 in generation, substituted or unsubstituted C3~C30 heterocycle in one kind.
6. according to a kind of organic semiconductive material described in claim 4, the Ar1、Ar2、Ar3Independently selected from substitution
Or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substitution
Or it is unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstitutedBase, substituted or unsubstituted base,
Substituted or unsubstituted fluoranthene base, substituted or unsubstituted indenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted fluorenes
Base, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted dibenzo Silole
Base, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted furans
Base, substituted or unsubstituted thienyl, substituted or unsubstituted quinolyl, substituted or unsubstituted indyl, substitution do not take
One kind in the phenoxazine base in generation, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazine thiophene base；
L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substitution or does not take
The phenanthryl in generation, substituted or unsubstituted base, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substitution or
It is unsubstitutedBase, substituted or unsubstituted indenyl, substituted or unsubstituted carbazyl, takes substituted or unsubstituted fluoranthene base
One kind in generation or unsubstituted fluorenyl, substituted or unsubstituted dibenzo Silole base；
R4、R5、R6、R7、R8、R9、R10It is independent to be selected from methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, substitution or do not take
The phenyl in generation, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted triazine radical, substitution
Or one kind in unsubstituted furyl, substituted or unsubstituted thienyl.
7. a kind of organic semiconductive material according to claim 1, which is characterized in that the dopant material is selected from as follows
Any one in structure：
8. a kind of organic semiconductive material according to claim 1, which is characterized in that the host material is selected from as follows
Any one in structure：
9. a kind of organic luminescent device, which is characterized in that the organic luminescent device including cathode, anode and is placed in the two successively
Between organic matter layer；It is at least one layer of in the organic matter layer to contain claim 1~8 any one of them organic semiconductive
Property material.
10. a kind of organic luminescent device according to claim 9, which is characterized in that the organic matter layer includes that hole passes
Defeated layer contains claim 1~8 any one of them organic semiconductive material in the hole transmission layer.
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| CN109037483A (en) * | 2018-08-07 | 2018-12-18 | 长春海谱润斯科技有限公司 | A kind of organic electroluminescence device |
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| CN109037483A (en) * | 2018-08-07 | 2018-12-18 | 长春海谱润斯科技有限公司 | A kind of organic electroluminescence device |
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