CN109378397A - A kind of organic electroluminescence device - Google Patents
A kind of organic electroluminescence device Download PDFInfo
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- CN109378397A CN109378397A CN201811531439.1A CN201811531439A CN109378397A CN 109378397 A CN109378397 A CN 109378397A CN 201811531439 A CN201811531439 A CN 201811531439A CN 109378397 A CN109378397 A CN 109378397A
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- H10K50/14—Carrier transporting layers
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- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
Abstract
The present invention provides a kind of organic electroluminescence device, belongs to organic photoelectric technical field.There is the device formula chemical formula I, II compound represented effectively to realize carrier injection balance under the collective effect of hole transmission layer and hole blocking layer, improve the generation and utilization rate of exciton.Organic luminescent device provided by the invention has many advantages, such as that starting voltage is low, luminous efficiency is high, long service life.
Description
Technical field
The present invention relates to organic photoelectric technical fields, and in particular to a kind of organic electroluminescence device.
Background technique
With the progress of information industry, traditional display has been unable to meet the requirement of people, such as: cathode-ray tube
(cathode ray tube, CRT) display volume is big, driving voltage is high；Liquid crystal display (liquid crystal
Display, LCD) brightness is low, narrow viewing angle, operating temperature range are small；Plasma display (plasma display panel,
PDP it) involves great expense, resolution ratio is not high, power consumption is big.
Organic electroluminescent LED (organic light-emitting diodes, OLEDs) is with organic matter for hair
The novel electroluminescent device of luminescent material, as a kind of completely new display technology possess in various performances existing display technology without
With the advantage of rival, it is simple by feat of its preparation process, have it is all solid state, wide from main light emission, brightness height, high-resolution, visual angle
(170 degree or more), fast response time, thin, small in size, light-weight, the usable flexible base board of thickness, low-voltage direct-current drive (3-
10V), low in energy consumption, operating temperature range is wide etc. so that its application market is very extensive, such as lighting system, communication system, vehicle
Load display, portable electronic device, fine definition show even military field.
In general, OLED uses stratiform or laminar structure, its structure of typical organic luminescent device is to generally comprise cathode, sun
Pole and the organic matter layer between electrode.The composition of device includes transparent ITO anode, hole injection layer (HIL), hole transport
The function such as layer (HTL), luminescent layer (EL), hole blocking layer (HBL), electron transfer layer (ETL), electron injecting layer (EIL), LiF/Al
Ergosphere.Organic electroluminescence device is by applying voltage at cathode, anode both ends, and Injection Current, electrons and holes are by respectively having
It after machine functional layer, is combined in luminescent layer and forms exciton, exciton returns to stable ground state to generate radioluminescence.
Summary of the invention
The object of the present invention is to provide a kind of organic electroluminescence device, the first electron transport layer materials provided by the invention
Good with the second electron transport layer materials compound stability, electron mobility is high, and glass transition temperature is high, good film-forming property, synthesis side
Method is simple to operation, and there is the organic electroluminescence device of preparation good luminous efficiency and service life to show.
Present invention firstly provides a kind of organic luminescent device, including cathode, anode, be located at the cathode and the anode it
Between organic matter layer, wherein organic matter layer include the first electron transfer layer and the second electron transfer layer, which is characterized in that it is described
First electron transfer layer contains chemical formula (I) compound represented, and second electron transfer layer contains chemical formula (II) institute
The compound shown:
Wherein R, R3、R4The aryl of alkyl, substituted or unsubstituted C6-C30 selected from substituted or unsubstituted C1-C30,
One of the heteroaryl of substituted or unsubstituted C3-C30；
Wherein R1、R2Selected from hydrogen, the alkyl of substituted or unsubstituted C1-C30, substituted or unsubstituted C6-C30 aryl,
One of the heteroaryl of substituted or unsubstituted C3-C30；
What wherein X was same or different is selected from CR5Or N, wherein R5Selected from hydrogen, substituted or unsubstituted C1-C30 alkyl,
One of the aryl of substituted or unsubstituted C6-C30, heteroaryl of substituted or unsubstituted C3-C30, and at least one
For N；
Wherein n1, n2, n3, n4 are independently same or differently selected from the integer more than or equal to 1；
Wherein L be selected from singly-bound, the divalent aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C3-C30 two
One of valence heteroaryl.
Preferably, the organic luminescent device, wherein R, R3、R4Alkyl, substitution selected from substituted or unsubstituted C1-C10
Or one of the aryl of unsubstituted C6-C18, heteroaryl of substituted or unsubstituted C3-C18；
Wherein R1、R2Selected from hydrogen, the alkyl of substituted or unsubstituted C1-C10, substituted or unsubstituted C6-C18 aryl,
One of the heteroaryl of substituted or unsubstituted C3-C18；
What wherein X was same or different is selected from CR5Or N, wherein R5Selected from hydrogen, substituted or unsubstituted C1-C10 alkyl,
One of the aryl of substituted or unsubstituted C6-C18, heteroaryl of substituted or unsubstituted C3-C18, and at least one
For N；
Wherein n1, n2, n3, n4 are independently same or differently selected from the integer for being less than or equal to 3 more than or equal to 1；
Wherein L be selected from singly-bound, the divalent aryl of substituted or unsubstituted C6-C18, substituted or unsubstituted C3-C18 two
One of valence heteroaryl.
Preferably, the organic luminescent device, wherein R, R3, R4 in substituted or unsubstituted following group one
Kind: phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, triazine radical, dibenzothiophene, pyridyl group,
Acridinyl, dibenzofuran group, quinolyl or isoquinolyl.
Preferably, the organic luminescent device, wherein the L is any one in singly-bound or structure as follows
Kind:
Preferably, the organic luminescent device, wherein the hole transport layer material is in structure as follows
Any one:
。
Preferably, any one of the hole barrier layer material in structure as follows:
Hole transmission layer of the present invention is between the luminescent layer and the anode.
Hole blocking layer of the present invention is between the luminescent layer and the cathode.
Beneficial effects of the present invention:
The present invention provides a kind of organic luminescent device, by designing device architecture, using hole transmission layer and hole barrier
The mode that layer combines prepares the organic luminescent device.
Hole transport layer material in the present invention introduces the structure of the acceptant electronics of diphenyl amine, increases the biography of carrier
Defeated property；In specific position, carbazole structure is introduced, compound molecular weight on the one hand can be increased, the material made has high glass
Glass transition temperature and the effect that can prevent crystallization, on the other hand make this kind of compound have one on stereoeffect
Fixed distortion improves its film forming.
The compound of fluorene class in hole barrier layer material in the present invention has the ability in acceptant hole, introduces bridging
On the one hand structure can increase compound molecular weight, the material made has high glass-transition temperature and can prevent
On the other hand the effect of crystallization makes this kind of compound have certain distortion on stereoeffect, improve its film forming.Separately
One end introduces the structure of pyridine, pyrimidine and the acceptant electronics of triazines in specific position, increases the transporting of carrier.This
Outside, this compound makes both parts about localization, and controls the flowing of conjugated system, so that compound has bipolarity, L is again
Two parts interaction is interrupted, so that the minimum that exciton is spread to other adjacent organic matter layers.
Specific embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described below with reference to embodiment, still
It should be appreciated that these descriptions are only further explanation the features and advantages of the present invention, rather than to the claims in the present invention
Limitation.
It should be noted that unless otherwise prescribed, the meaning of scientific and technical terminology used in the present invention and those skilled in the art
The meaning that member is generally understood is identical.
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 or 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 total of the group that one or more aromatic core carbon are substituted by hetero atom in aryl
Claim, the hetero atom includes but is not limited to oxygen, sulphur, nitrogen or silicon atom, and the heteroaryl can be monocycle or condensed ring, and example can wrap
Include pyridyl group, phenothiazinyl, phenoxazine base, pyrimidine radicals, benzo pyrimidine radicals, carbazyl, triazine radical, benzothiazolyl, benzo miaow
Oxazolyl, acridinyl etc., but not limited to this.
Divalent aryl of the present invention refers to respectively remove a hydrogen atom on two aromatic core carbon of aromatic hydrocarbon molecule after, be left
Bivalent group general name, can be valentbivalent monocyclic aryl or divalent fused ring aryl, such as can be selected from phenylene, sub- biphenyl
Base, sub- terphenyl, naphthylene, anthrylene, phenanthrylene, sub- pyrenyl, fluorenylidene or sub- benzo phenanthryl etc., but not limited to this.
Divalent heteroaryl radical of the present invention refers to that one or more aromatic core carbon in divalent aryl are replaced to obtain by hetero atom
Group general name, the hetero atom includes but is not limited to oxygen, sulphur or nitrogen-atoms, and the divalent heteroaryl radical can be valentbivalent monocyclic
Heteroaryl or divalent fused ring heteroaryl, such as can be selected from sub-pyridyl group, sub- quinolyl, sub- carbazyl, sub- thienyl, sub- benzo
Thienyl, furylidene, sub- benzofuranyl, sub- pyrimidine radicals, sub- benzo pyrimidine radicals, sub- imidazole radicals or sub- benzimidazolyl etc.,
But not limited to this.
In substituted alkyl of the present invention, substituted aryl, substituted heteroaryl etc., the substituent group can be independent
Selected from D-atom, cyano, nitro, halogen atom, the alkyl of C1-C10, the alkoxy of C1-C10, the alkylthio group of C1-C10, C1-
The aryl of C30, the aryloxy group of C1-C30, the arylthio of C1-C30, C3-C30 heteroaryl, the silylation of C1~C30, C2~
Alkylamino radical, aryl amine of C6~C30 of C10 etc., such as D-atom, cyano, nitro, halogen, methyl, ethyl, propyl, isopropyl
Base, tert-butyl, methoxyl group, methyl mercapto, phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, benzo phenanthryl, base, pyrene
Base, fluorenyl, 9,9- dimethyl fluorenyl, benzyl, phenoxy group, thiophenyl, hexichol amido, dimethylamino, carbazyl, 9- phenyl click
Oxazolyl, furyl, thienyl, triphenyl silicon substrate, trimethyl silicon substrate, trifluoromethyl, phenothiazinyl, phenoxazine base, acridinyl, piperazine
Piperidinyl, pyridyl group, pyrazinyl, triazine radical, pyrimidine radicals etc., but not limited to this.
Present invention firstly provides a kind of organic luminescent device, including cathode, anode, be located at the cathode and the anode it
Between organic matter layer, wherein organic matter layer includes hole transmission layer and electronic barrier layer, which is characterized in that the hole transport
Layer contains chemical formula (II) compound represented containing chemical formula (I) compound represented, the hole blocking layer:
Wherein R, R3、R4The aryl of alkyl, substituted or unsubstituted C6-C30 selected from substituted or unsubstituted C1-C30,
One of the heteroaryl of substituted or unsubstituted C3-C30；
Wherein R1、R2Selected from hydrogen, the alkyl of substituted or unsubstituted C1-C30, substituted or unsubstituted C6-C30 aryl,
One of the heteroaryl of substituted or unsubstituted C3-C30；
What wherein X was same or different is selected from CR5Or N, wherein R5Selected from hydrogen, substituted or unsubstituted C1-C30 alkyl,
One of the aryl of substituted or unsubstituted C6-C30, heteroaryl of substituted or unsubstituted C3-C30, and at least one
For N；
Wherein n1, n2, n3, n4 are independently same or differently selected from the integer more than or equal to 1；
Wherein L be selected from singly-bound, the divalent aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C3-C30 two
One of valence heteroaryl.
Preferably, in the organic luminescent device, R, R3、R4Alkyl selected from substituted or unsubstituted C1-C10, replace or
One of the aryl of unsubstituted C6-C18, heteroaryl of substituted or unsubstituted C3-C18；
Wherein R1、R2Selected from hydrogen, the alkyl of substituted or unsubstituted C1-C10, substituted or unsubstituted C6-C18 aryl,
One of the heteroaryl of substituted or unsubstituted C3-C18；
What wherein X was same or different is selected from CR5Or N, wherein R5Selected from hydrogen, substituted or unsubstituted C1-C10 alkyl,
One of the aryl of substituted or unsubstituted C6-C18, heteroaryl of substituted or unsubstituted C3-C18, and at least one
For N；
Wherein n1, n2, n3, n4 are independently same or differently selected from the integer for being less than or equal to 3 more than or equal to 1；
Wherein L be selected from singly-bound, the divalent aryl of substituted or unsubstituted C6-C18, substituted or unsubstituted C3-C18 two
One of valence heteroaryl.
Preferably, in the organic luminescent device, R, R3、R4Selected from one of substituted or unsubstituted following group: benzene
Base, naphthalene, anthryl, phenanthryl, pyrenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, triazine radical, dibenzothiophene, pyridyl group, acridine
Base, dibenzofuran group, quinolyl or isoquinolyl.
Preferably, in the organic luminescent device, R1、R2Selected from one of hydrogen, substituted or unsubstituted following group:
Phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, triazine radical, dibenzothiophene, pyridyl group, acridine
Base, dibenzofuran group, quinolyl or isoquinolyl.
Preferably, in the organic luminescent device, any one of L in singly-bound or structure as follows:
Preferably, any one of the defeated layer material in the hole in structure as follows:
。
Preferably, any one of the hole barrier layer material in structure as follows:
。
Some specific structure types of compound of the present invention are enumerated above, but the invention is not limited to listed
These chemical structures, it is all based on structure shown in formula (I) and formula (II), various substituent groups be group as defined above
It should all be included.
Hole transport layer material of the present invention, preparation method are as follows:
Compound 1-a and compound 1-b are coupled to obtain compound 1-c, compound 1-c and compound 1-d coupling
Close object 1-e.
Hole barrier layer material of the present invention, preparation method are as follows:
Compound 2-a and compound 2-b are coupled to obtain compound 2-c, compound 2-c and compound 2-d coupling
Close object 2-e.
Organic luminescent device of the present invention can be used for the application neck such as flat-panel monitor, lighting source, direction board, signal lamp
Domain.
By following embodiment, the present invention, but so as not to the limitation present invention are more fully explained.In the base of the description
On plinth, those of ordinary skill in the art will without creative efforts, in disclosed entire scope
Implement the present invention and prepares other compounds and device according to the present invention.
The present invention is not particularly limited the source of raw material employed in following embodiment, can for commercial product or
It is prepared using preparation method well-known to those skilled in the art.
Embodiment 1:
The preparation of compound 1-1
The preparation of intermediate 1-1-3
By tri-tert-butylphosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium acetate (0.4g,
1.83mmol) and sodium tert-butoxide (52.7g, 549mmol) be added to 1-1 (33.42g, 100mmol) and 1-2 (30.99g,
100mmol) the solution in degassed toluene (500mL), and the mixture is heated 2 hours under reflux.The reaction is mixed
It closes object to be cooled to room temperature, be filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and is extracted with toluene, and
And merge organic phase, it is evaporated under vacuum.The residue is filtered via silica gel (heptane/methylene chloride),
And it is crystallized from isopropanol.Obtain intermediate 1-1-3 45.13g, yield 80%.
The preparation of compound 1-1
By tri-tert-butylphosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium acetate (0.4g,
1.83mmol) and sodium tert-butoxide (52.7g, 549mmol) be added to 1-1-3 (56.41g, 100mmol) and 1-1-4 (16.91g,
100mmol) the solution in degassed toluene (500mL), and the mixture is heated 2 hours under reflux.The reaction is mixed
It closes object to be cooled to room temperature, be filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and is extracted with toluene, and
And merge organic phase, it is evaporated under vacuum.The residue is filtered via silica gel (heptane/methylene chloride),
And it is crystallized from isopropanol.Obtain 1 48.99g of compound, yield 75%.
Embodiment 2:
The preparation of compound 1-32
The preparation of compound 1-32
1-1-1 in embodiment 1 is replaced with into 1-32-1 as shown above, 1-1-4 replaces with 1-32-4 as shown above, obtains
Compound 1-32.Mass spectrum m/z:845.38 (calculated value: 845.40).Theoretical elemental content (%) C63H47N3: C, 89.43；H,
5.60；N, 4.97 actual measurement constituent content (%): C, 89.44；H, 5.61；N, 4.98.It is target product that above-mentioned confirmation, which obtains product,
1-32。
Embodiment 3:
The preparation of compound 1-63
The preparation of compound 1-63
1-1-1 in embodiment 1 is replaced with into 1-63-1 as shown above, 1-1-4 replaces with 1-63-4 as shown above, obtains
Compound 1-63.Mass spectrum m/z:957.41 (calculated value: 957.43).Theoretical elemental content (%) C72H51N3: C, 90.25；H,
5.36；N, 4.39 actual measurement constituent content (%): C, 90.26；H, 5.35；N, 4.38.It is target product that above-mentioned confirmation, which obtains product,
1-63。
Embodiment 4:
The preparation of compound 1-87
The preparation of compound 1-87
1-1-1 in embodiment 1 is replaced with into 1-87-1 as shown above, 1-1-4 replaces with 1-87-4 as shown above, obtains
Compound 1-87.Mass spectrum m/z:945.37 (calculated value: 945.38).Theoretical elemental content (%) C70H47N3O:C, 88.86；H,
5.01；N, 4.44；O, 1.69 actual measurement constituent content (%): C, 88.88；H, 5.02；N, 4.454；O, 1.68.Above-mentioned confirmation obtains
Product is target product 1-87.
Embodiment 5:
The preparation of compound 1-95
The preparation of compound 1-95
1-1-1 in embodiment 1 is replaced with into 1-95-1 as shown above, 1-1-4 replaces with 1-95-4 as shown above, obtains
Compound 1-87.Mass spectrum m/z:957.41 (calculated value: 957.42).Theoretical elemental content (%) C72H51N3: C, 90.25；H,
5.36；N, 4.39 actual measurement constituent content (%): C, 90.26；H, 5.35；N, 4.38.It is target product that above-mentioned confirmation, which obtains product,
1-95。
Embodiment 6:
The preparation of compound 1-111
The preparation of compound 1-111
1-1-1 in embodiment 1 is replaced with into 1-111-1 as shown above, 1-1-2 replaces with 1-111-2 as shown above, 1-
1-4 replaces with 1-111-4 as shown above, obtains compound 1-111.Mass spectrum m/z:779.33 (calculated value: 779.34).Theoretical member
Cellulose content (%) C58H41N3: C, 89.31；H, 5.30；N, 5.39 actual measurement constituent content (%): C, 89.32；H, 5.31；N, 5.38.
It is target product 1-111 that above-mentioned confirmation, which obtains product,.
Embodiment 7:
The preparation of compound 1-125
The preparation of compound 1-125
1-1-1 in embodiment 1 is replaced with into 1-25-1 as shown above, 1-1-2 replaces with 1-125-2 as shown above, 1-
1-4 replaces with 1-125-4 as shown above, obtains compound 1-125.Mass spectrum m/z:885.36 (calculated value: 885.38).Theoretical member
Cellulose content (%) C63H44N4: C, 88.29；H, 5.17；N, 6.54 actual measurement constituent content (%): C, 88.28；H, 5.18；N, 6.53.
It is target product 1-111 that above-mentioned confirmation, which obtains product,.
Embodiment 8:
The preparation of compound 2-1
The preparation of intermediate 2-1-3
Under the protection of nitrogen, 2-1-1 (35.92g, 100.08mmol) is added into 2L reaction kettle, 2-1-2 (28.19g,
100.08mmol), potassium carbonate (1.24g, 9.00mmol), toluene 200mL stirring.Reactor temperature is raised to 70 DEG C, and Pd is added
(PPh3)4(1.04g, 0.90mmol), distilled water 100mL stirring, is stirred at reflux 11h, sufficiently reacts.It is whole that 70mL distilled water is added
It after only reacting, is filtered under diminished pressure, is washed with distilled water solid, then use acetone, toluene, THF is recrystallized, risen again after obtaining solid
China, re crystallization from toluene obtain intermediate 1-3 31.13g, yield 80.44%.
The preparation of compound 2-1
It is identical as the preparation method of intermediate 2-1-3, obtain compound 2-1 40.14g, yield 75%.Mass spectrum m/z:
535.20 (calculated values: 535.21).Theoretical elemental content (%) C39H25N3: C, 87.45；H, 4.70；N, 7.84 actual measurement elements contain
Measure (%): C, 87.46；H, 4.71；N, it is target product 2-1 that 7.85 above-mentioned confirmations, which obtain product,.
Embodiment 9:
The preparation of compound 2-11
The preparation of compound 2-11
2-1-2 in embodiment 1 is replaced with into 2-11-2 as shown above, 2-1-5 replaces with 2-11-5 as shown above, obtains
Compound 2-11.Mass spectrum m/z:699.29 (calculated value: 699.30).Theoretical elemental content (%) C54H37N:C, 92.67；H,
5.33；N, 2.00 actual measurement constituent content (%): C, 92.68；H, 5.32；N, 2.01.It is target product that above-mentioned confirmation, which obtains product,
2-11。
Embodiment 10:
The preparation of compound 2-20
The preparation of compound 2-20
2-1-1 in embodiment 1 is replaced with into 2-20-1 as shown above, 2-1-2 replaces with 2-20-2 as shown above, 2-1-
5 replace with 2-20-5 as shown above, obtain compound 2-20.Mass spectrum m/z:501.22 (calculated value: 501.23).Theoretical elemental contains
Measure (%) C36H27N3: C, 86.20；H, 5.43；N, 8.38 actual measurement constituent content (%): C, 86.22；H, 5.42；N, 8.37.It is above-mentioned
Confirm that obtaining product is target product 2-20.
Embodiment 11:
The preparation of compound 2-30
The preparation of compound 2-30
2-1-1 in embodiment 1 is replaced with into 2-30-1 as shown above, 2-1-2 replaces with 2-30-2 as shown above, 2-1-
5 replace with 2-30-5 as shown above, obtain compound 2-30.Mass spectrum m/z:625.25 (calculated value: 625.26).Theoretical elemental contains
Measure (%) C46H31N3: C, 88.29；H, 4.99；N, 6.72 actual measurement constituent content (%): C, 88.28；H, 4.98；N, 6.73.It is above-mentioned
Confirm that obtaining product is target product 2-30.
Embodiment 12:
The preparation of compound 2-47
The preparation of compound 2-47
2-1-1 in embodiment 1 is replaced with into 2-47-1 as shown above, 2-1-2 replaces with 2-47-2 as shown above, 2-1-
5 replace with 2-47-5 as shown above, obtain compound 2-47.Mass spectrum m/z:701.28 (calculated value: 701.29).Theoretical elemental contains
Measure (%) C52H35N3: C, 88.99；H, 5.03；N, 5.99 actual measurement constituent content (%): C, 88.98；H, 5.02；N, 5.98.It is above-mentioned
Confirm that obtaining product is target product 2-47.
[comparison Application Example]
Transparent anode electrode ito substrate is cleaned each 15 minutes with deionized water, acetone, EtOH Sonicate respectively, is then existed
It is cleaned 2 minutes in plasma cleaning device, dry and is evacuated to 5 × 10-5Pa.Then by treated, ito substrate steams
Plating.Successively vapor deposition hole injection layer HAT-CN/50nm, vapor deposition hole transmission layer NPB/30nm, vapor deposition main body CBP: doping Ir
(ppy)310% mixing/30nm, then vapor deposition the first electron transfer layer TPBi/30nm, electron injecting layer LiF/0.5nm, cathode
Al/200nm。
[Application Example 1-7]
Change the compound in the hole transmission layer compared in Application Example into shown compound 1- in embodiment 1-7
1、1-32、1-63、1-87、1-95、1-111、1-125。
[Application Example 8-12]
On the basis of Application Example 1, increase hole blocking layer, between luminescent layer and electron transfer layer, vapor deposition
Compound 2-1,2-11,2-20,2-30,2-47 in embodiment 8-12.
Table 1 is the compound of preparation of the embodiment of the present invention and the characteristics of luminescence test for comparing luminescent device prepared by substance
As a result.
The characteristics of luminescence of [table 1] luminescent device is tested
The above result shows that organic luminescent device provided by the invention, by combining chemical formula I, II of the present invention
Compound represented designs hole transmission layer and hole blocking layer, then carries out reasonable device structure design, in hole transport
Under the collective effect of layer and hole blocking layer, carrier injection balance is effectively realized, the generation and utilization rate of exciton are improved.
Organic luminescent device provided by the invention has the advantages that starting voltage is low, luminous efficiency is high, long service life, and its offer
It prepares the raw material that the compound of the organic luminescent device uses to be easy to get, synthetic method is simple, and easy to operate, high degree is met
The demand of industry and market.
Although the present invention has carried out special description with exemplary embodiment, but it is understood that without departing from claim
Defined by the case where spirit and scope of the invention, those of ordinary skill in the art can carry out various forms and details to it
On change.
Claims (7)
1. a kind of organic luminescent device, including cathode, anode, the organic matter layer between the cathode and the anode,
Middle organic matter layer includes hole transmission layer and hole blocking layer, which is characterized in that the hole transmission layer contains chemical formula (I)
Compound represented, the hole blocking layer contain chemical formula (II) compound represented:
Wherein R, R3、R4The aryl of alkyl, substituted or unsubstituted C6-C30 selected from substituted or unsubstituted C1-C30 replaces
Or one of heteroaryl of unsubstituted C3-C30；
Wherein R1、R2Selected from hydrogen, the alkyl of substituted or unsubstituted C1-C30, the aryl of substituted or unsubstituted C6-C30, substitution
Or one of heteroaryl of unsubstituted C3-C30；
What wherein X was same or different is selected from CR5Or N, wherein R5Selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, replace
Or one of the aryl of unsubstituted C6-C30, heteroaryl of substituted or unsubstituted C3-C30, and at least one is N；
Wherein n1, n2, n3, n4 are independently same or differently selected from the integer more than or equal to 1；
Wherein it is miscellaneous to be selected from singly-bound, the divalent aryl of substituted or unsubstituted C6-C30, the divalent of substituted or unsubstituted C3-C30 by L
One of aryl.
2. organic luminescent device according to claim 1, which is characterized in that described R, the R3、R4Selected from substituted or unsubstituted
One of the alkyl of C1-C10, the aryl of substituted or unsubstituted C6-C18, heteroaryl of substituted or unsubstituted C3-C18；
Wherein R1、R2Selected from hydrogen, the alkyl of substituted or unsubstituted C1-C10, the aryl of substituted or unsubstituted C6-C18, substitution
Or one of heteroaryl of unsubstituted C3-C18；
What wherein X was same or different is selected from CR5Or N, wherein R5Selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, replace
Or one of the aryl of unsubstituted C6-C18, heteroaryl of substituted or unsubstituted C3-C18, and at least one is N；
Wherein n1, n2, n3, n4 are independently same or differently selected from the integer for being less than or equal to 3 more than or equal to 1；
Wherein it is miscellaneous to be selected from singly-bound, the divalent aryl of substituted or unsubstituted C6-C18, the divalent of substituted or unsubstituted C3-C18 by L
One of aryl.
3. organic luminescent device according to claim 1, which is characterized in that described R, the R3、R4Selected from substituted or unsubstituted
One of following group: phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, triazine radical, dibenzo
Thienyl, pyridyl group, acridinyl, dibenzofuran group, quinolyl or isoquinolyl.
4. organic luminescent device according to claim 1, which is characterized in that the R1、R2Selected from hydrogen, substituted or unsubstituted
One of following group: phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, triazine radical, hexichol
Bithiophene base, pyridyl group, acridinyl, dibenzofuran group, quinolyl or isoquinolyl.
5. organic luminescent device according to claim 1, which is characterized in that the L is selected from singly-bound or knot as follows
Any one in structure:
6. organic luminescent device according to claim 1, which is characterized in that the hole transport layer material is selected from following institute
Show any one in structure:
7. organic luminescent device according to claim 1, which is characterized in that the hole barrier layer material is selected from following institute
Show any one in structure:
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