CN109096268A - A kind of organic electroluminescent compounds and its organic electroluminescence device - Google Patents
A kind of organic electroluminescent compounds and its organic electroluminescence device Download PDFInfo
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
The present invention provides a kind of organic electroluminescent compounds and its organic electroluminescence device, is related to technical field of organic electroluminescence.Organic electroluminescent compounds provided by the invention can be used as light and take out layer material, improve the transmitance of half transmitting electrode, light direction and light extraction efficiency adjusted, so as to effectively improve the light emission luminance of device；Organic electroluminescent compounds of the invention can also be applied in OLED device as light removing layer and hole transmission layer simultaneously, the luminescent properties of device not only can be improved, moreover it is possible to effectively save cost.
Description
Technical field
The present invention relates to technical field of organic electroluminescence, and in particular to a kind of organic electroluminescent compounds and its organic
Electroluminescent device.
Background technique
Organic electroluminescent LED (Organic Light-Emitting Diode, OLED) refers to luminous organic material
The diode to shine under the action of electric current or electric field, electric energy can be converted into luminous energy by it.Kodak Company in 1987
Tang etc. has invented sandwich type organic bilayer film luminescent device, this breakthrough, allows it is seen that OLED technology
Great potential that is practical, moving towards commercial market is moved towards, the research boom of Organic Light Emitting Diode has been started.Over 30 years, OLED
Technology achieves development with rapid changepl. never-ending changes and improvements, moves towards the industrialization production from laboratory research.All solid state, the active of OLED technology
Shine, high contrast, it is ultra-thin, can Flexible Displays, low-power consumption, wide viewing angle, fast response time, operating temperature range is wide, it is real to be easy to
Many advantages, such as existing 3D display, " fantasy display " is known as by insider, will become following most potential new
Type display technology.
But for the actual demand of current organic electroluminescent industry, the development of electroluminescent organic material lags behind face
The requirement of plate manufacturing enterprise, therefore as material type enterprise, developing, there is the organic functional material of higher performance to seem especially heavy
It wants.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, the present invention provides a kind of organic electroluminescent compounds and its Organic Electricity
Electroluminescence device.
The present invention provides a kind of organic electroluminescent compounds, there is structure shown in logical formula (I) as follows:
Ar1For structure shown in formula (I-1), Ar2For structure shown in formula (I-2):
Wherein, each R1、R2、R3、R4Independently selected from hydrogen atom, D-atom, halogen atom, C1~C10 alkyl,
The alkoxy of C1~C10, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 heteroaryl in
It is a kind of；Or the R1、R2、R3、R4The condensed cyclization of both middle arbitrary neighborhoods；A is selected from 0 to 3 integer, and b, c, d are independent to be selected from 0
To 4 integer；
Each R5、R6Independently selected from hydrogen atom, D-atom, halogen atom, the alkyl of C1~C10, C1~C10 alkane
One of oxygroup, the aryl of substituted or unsubstituted C6~C30, heteroaryl of substituted or unsubstituted C3~C30；Or it is described
R5、R6The condensed cyclization of both middle arbitrary neighborhoods；E is selected from 0 to 4 integer, and f is selected from 0 to 3 integer；
Ar3、Ar4Aryl or the Ar independently selected from substituted or unsubstituted C6~C303、Ar4With the N being connect
Condensed cyclization.
Preferably, the Ar1Any one in such as flowering structure:
Preferably, the Ar2Any one in such as flowering structure:
Preferably, the Ar1In structure as follows any one:
Preferably, the Ar2Any one in such as flowering structure:
Preferably, the Ar3、Ar4Independently selected from phenyl, xenyl, terphenyl, naphthalene or Ar3、Ar4With connect
The N connect is fused into structure as follows:
Preferably, any one of the organic electroluminescent compounds in structure as follows:
The present invention also provides a kind of organic electroluminescence devices comprising the organic electroluminescent compounds.
Preferably, the organic electroluminescence device includes light removing layer, cathode, organic matter layer, anode and substrate, described
At least one layer in light removing layer and the organic matter layer contains the organic electroluminescent compounds.
Preferably, contain hole transmission layer in the organic matter layer, in the smooth removing layer and the hole transmission layer
At least one layer contains the organic electroluminescent compounds.
Beneficial effects of the present invention:
Organic electroluminescent compounds provided by the invention are derivative containing the arylamine of two fluorenes of spiral shell and dibenzofurans simultaneously
Object increases the molecular weight of compound, improves glass transition temperature by introducing two fluorenes of spiral shell and dibenzofurans group simultaneously
Degree, keeps film forming and stability more preferable；Have rigidity flat by being further introduced into phenyl, xenyl, naphthalene or nitrogen-containing heterocycle etc.
The group of face structure and big pi-conjugated system, makes it have good thermal stability and higher carrier mobility, has height
Hole mobility, be conducive to the injection and transmission in hole；Organic electroluminescent compounds of the invention refraction with higher
Rate, refractive index can reach 1.84~1.91, can be used as light and take out layer material, improve the transmitance of half transmitting electrode, adjust out
Light direction and light extraction efficiency, so as to effectively improve the light emission luminance of device；Organic electroluminescent compounds of the invention are also
It can be applied in OLED device as light removing layer and hole transmission layer simultaneously, the luminescent properties of device not only can be improved,
It can also effectively save cost.
Specific embodiment
It is clearly and completely described below in conjunction with the technical solution of the specific embodiment of the invention, it is clear that described
Embodiment is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field
Technical staff's every other embodiment obtained without making creative work, belongs to protection model of the invention
It encloses.
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 one or several hydrogen atoms in alkane molecule, can be straight
Alkyl group, branched alkyl, naphthenic base, example may include methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl,
Tert-butyl, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Alkoxy of the present invention refer to alkyl and oxygen atom connection after group, example may include methoxyl group, ethyoxyl,
2- propoxyl group, 2- cyclohexyloxy 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.
Condensed cyclization of the present invention refers to that two groups are connected to each other by chemical bond.It is as follows:
In the present invention, the ring being fused into can be five-membered ring or hexatomic ring, such as phenyl, naphthalene, hexamethylene and phenyl, click
Oxazolyl, quinolyl, dibenzothiophene, phenanthryl or pyrenyl, but not limited to this.
Present invention firstly provides a kind of organic electroluminescent compounds, there is structure shown in logical formula (I) as follows:
Ar1For structure shown in formula (I-1), Ar2For structure shown in formula (I-2):
Wherein, each R1、R2、R3、R4Independently selected from hydrogen atom, D-atom, halogen atom, C1~C10 alkyl,
The alkoxy of C1~C10, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 heteroaryl in
It is a kind of；Or the R1、R2、R3、R4The condensed cyclization of both middle arbitrary neighborhoods；A is selected from 0 to 3 integer, and b, c, d are independent to be selected from 0
To 4 integer；
Each R5、R6Independently selected from hydrogen atom, D-atom, halogen atom, the alkyl of C1~C10, C1~C10 alkane
One of oxygroup, the aryl of substituted or unsubstituted C6~C30, heteroaryl of substituted or unsubstituted C3~C30；Or it is described
R5、R6The condensed cyclization of both middle arbitrary neighborhoods；E is selected from 0 to 4 integer, and f is selected from 0 to 3 integer；
Ar3、Ar4Aryl or the Ar independently selected from substituted or unsubstituted C6~C303、Ar4With the N being connect
Condensed cyclization.
Heretofore described " substituted or unsubstituted ", the substituent group is independent to be selected from D-atom, cyano, nitro, halogen
Plain atom, the alkyl of C1-C10, the alkoxy of C1-C10, the alkylthio group of C1-C10, the aryl of C6-C30, C6-C30 fragrant oxygen
Base, the arylthio of C6-C30, C3-C30 heteroaryl, C1~C30Silylation, C2~C10Alkylamino radical, C6~C30Aryl amine
Deng, for example, D-atom, cyano, nitro, halogen, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxyl group, methyl mercapto, phenyl,
Xenyl, terphenyl, naphthalene, anthryl, phenanthryl, benzo phenanthryl, base, pyrenyl, fluorenyl, 9,9- dimethyl fluorenyl, benzyl,
Phenoxy group, thiophenyl, hexichol amido, dimethylamino, carbazyl, 9- phenyl carbazole base, furyl, thienyl, triphenyl silicon substrate,
Trimethyl silicon substrate, trifluoromethyl, phenothiazinyl, phenoxazine base, acridinyl, piperidyl, pyridyl group, pyrazinyl, triazine radical, pyrimidine
Base etc., but not limited to this.
According to the present invention, preferably each R1、R2、R3、R4Independently selected from hydrogen atom, D-atom, halogen atom, substitution
Or one in unsubstituted C1-C4 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl
Kind；Or the R1、R2、R3、R4The condensed cyclization of both middle arbitrary neighborhoods；It is furthermore preferred that each R1、R2、R3、R4Independently selected from
Hydrogen atom, D-atom, fluorine atom, chlorine atom, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthalene, xenyl,
One of terphenyl, carbazyl；Or the R1、R2、R3、R4Both middle arbitrary neighborhoods are fused into phenyl ring.
Preferably, the Ar1Any one in such as flowering structure:
According to the present invention, preferably each R5、R6It does not take independently selected from hydrogen atom, D-atom, halogen atom, substitution or
One of the C1-C4 alkyl in generation, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl；Or
The R5、R6The condensed cyclization of both middle arbitrary neighborhoods；It is furthermore preferred that each R5、R6Independently selected from hydrogen atom, D-atom, fluorine
Atom, chlorine atom, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthalene, xenyl, terphenyl, in carbazyl
One kind；Or the R5、R6Both middle arbitrary neighborhoods are fused into phenyl ring.
Preferably, the Ar2Any one in such as flowering structure:
Preferably, the Ar1Any one in structure as follows:
Preferably, the Ar2Any one in such as flowering structure:
According to the present invention, preferably Ar3、Ar4Independently selected from phenyl, xenyl, terphenyl, naphthalene or Ar3、Ar4With institute
The N of connection is fused into structure as follows:
It is furthermore preferred that the Ar3、Ar4Structure as follows is fused into the N being connect:
As an example, it is not particularly limited, the organic electroluminescent compounds are any in structure as follows
It is a kind of:
Some specific constructive forms of organic electroluminescent compounds of the present invention are enumerated above, but the present invention is not
It is confined to these listed chemical structures, all based on structure shown in formula (I), Ar1、Ar2、Ar3And Ar4It is as defined above
Group should all be included.
The preparation method of organic electroluminescent compounds of the present invention can be prepared by conventional coupling reaction,
Such as it can be prepared by following synthetic route, however, the present invention is not limited thereto:
The aromatic amine compound A and compound B replaced simultaneously by bromine and iodine obtains intermediate C by coupling reaction；Intermediate
C obtains target compound (I) again with aromatic amine compound D by coupling reaction.
Wherein, Ar1、Ar2、Ar3And Ar4Restriction as described above, details are not described herein.
The present invention does not have special limitation to the above-mentioned reaction condition respectively reacted, and use is well-known to those skilled in the art
Reaction condition.The present invention is not particularly limited the source of raw material employed in above-mentioned each reaction, can be commercially available
Product is prepared using preparation method well-known to those skilled in the art.Organic electroluminescent compounds of the present invention
Synthesis step is few, processing is simple, easy to industrialized production.
The present invention also provides a kind of organic electroluminescence devices comprising the organic electroluminescent compounds.Institute of the present invention
Stating organic electroluminescence device is preferably top emitting device.
As organic electroluminescence device of the invention, structure can successively include light removing layer, cathode, organic matter
Layer, anode and substrate, at least one layer in the smooth removing layer and the organic matter layer contain the organic electroluminescent
Close object.It may include hole injection layer, hole transmission layer, luminous auxiliary layer, luminescent layer, hole barrier in the organic matter layer
Layer, electron transfer layer, at least one layer in electron injecting layer；It is preferred that the organic matter layer at least contains hole transmission layer, it is described
At least one layer in light removing layer and the hole transmission layer contains the organic electroluminescent compounds.
However, the structure of organic electroluminescence device of the present invention is not limited to this, organic electroluminescence of the present invention
Luminescent device can be selected and be combined according to the characteristic of device parameter requirements and material, and it is organic can also to add or omit part
Layer.As an example, the device architecture used in an embodiment of the present invention can be with are as follows: ITO/Ag/ITO transparent glass conduct
Anode；NPB or organic electroluminescent compounds of the present invention (in compound 1-132 any one) are used as hole transport
Layer；CBP and (piq)2Ir (acac) is used as luminescent layer；TPBI is as electron transfer layer；Magnesium ag alloy layer is as cathode；The present invention
The organic electroluminescent compounds (in compound 1-132 any one) are vaporized on above-mentioned cathode as light removing layer.
Organic electroluminescence device of the present invention can be used for flat-panel monitor, lighting source, direction board, signal lamp etc. and answer
Use field.
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
Under argon atmospher, by 7.00g (30mmol) intermediate A -1,10.77g (30mmol) B-1,5.77g (60mmol) tertiary fourth
Sodium alkoxide is dissolved in 300ml dehydrated toluene, is added with stirring 0.14g (0.6mmol) palladium acetate, 0.12g (0.6mmol) triphenyl
Phosphine reacts 8 hours at 80 DEG C.It after cooling, is filtered by diatomite/silica gel funnel, filtrate is organic by vacuum distillation removal
Solvent, it is residue obtained to be recrystallized in toluene, it is dry, 11.84g (25.5mmol) intermediate C-1 can be obtained, yield is
85%.
Under argon atmospher, by 9.29g (20mmol) intermediate C-1,9.95g (20mmol) D-1,3.85g (40mmol) tertiary fourth
Sodium alkoxide is dissolved in 300ml dehydrated toluene, is added with stirring 0.09g (0.4mmol) palladium acetate, 0.09g (0.4mmol) triphenyl
Phosphine reacts 8 hours at 80 DEG C.It after cooling, is filtered by diatomite/silica gel funnel, filtrate is organic by vacuum distillation removal
Solvent, it is residue obtained to be recrystallized in toluene, it is dry, 14.26g (16.2mmol) compound 1, yield 81% can be obtained.
Mass spectrum m/z:880.38 (calculated value: 880.35).Theoretical elemental content (%) C66H44N2O:C, 89.97；H,5.03；N,3.18；
O,1.82.Survey constituent content (%): C, 89.92；H,5.04；N,3.17；O,1.80.The above results confirm that obtaining product is mesh
Mark product.
Embodiment 2: the preparation of compound 4
Intermediate D-1 in embodiment 1 is replaced with to the intermediate D-4 of equimolar amounts, other steps with embodiment 1
It is identical, obtain compound 4.Mass spectrum m/z:992.38 (calculated value: 992.47).Theoretical elemental content (%) C74H60N2O:C,
89.48；H,6.09；N,2.82；O,1.61.Survey constituent content (%): C, 89.50；H,6.07；N,2.87；O,1.60.It is above-mentioned
As a result confirm that obtaining product is target product.
Embodiment 3: the preparation of compound 5
Intermediate B -1 in embodiment 1 is replaced with to the intermediate B -5 of equimolar amounts, intermediate C-1 is replaced with
The intermediate C-5 of mole, other steps are same as Example 1, obtain compound 5.Mass spectrum m/z:880.39 (calculated value:
880.35).Theoretical elemental content (%) C66H44N2O:C, 89.97；H,5.03；N,3.18；O,1.82.Survey constituent content
(%): C, 89.92；H,5.04；N,3.17；O,1.81.The above results confirm that obtaining product is target product.
Embodiment 4: the preparation of compound 6
Intermediate B -1 in embodiment 1 is replaced with to the intermediate B -5 of equimolar amounts, intermediate C-1 is replaced with
The intermediate C-5 of mole, intermediate D-1 are replaced with the intermediate D-6 of equimolar amounts, other steps with 1 phase of embodiment
Together, compound 6 is obtained.Mass spectrum m/z:908.29 (calculated value: 908.38).Theoretical elemental content (%) C68H48N2O:C, 89.84；
H,5.32；N,3.08；O,1.76.Survey constituent content (%): C, 89.79；H,5.34；N,3.07；O,1.77.The above results card
The real product that obtains is target product.
Embodiment 5: the preparation of compound 9
Intermediate B -1 in embodiment 1 is replaced with to the intermediate B -9 of equimolar amounts, intermediate C-1 is replaced with
The intermediate C-9 of mole, other steps are same as Example 1, obtain compound 9.Mass spectrum m/z:880.40 (calculated value:
880.35).Theoretical elemental content (%) C66H44N2O:C, 89.97；H,5.03；N,3.18；O,1.82.Survey constituent content
(%): C, 89.90；H,5.04；N,3.17；O,1.80.The above results confirm that obtaining product is target product.
Embodiment 6: the preparation of compound 13
Intermediate B -1 in embodiment 1 is replaced with to the intermediate B -13 of equimolar amounts, intermediate C-1 is replaced with
The intermediate C-13 of equimolar amounts, other steps are same as Example 1, obtain compound 13.Mass spectrum m/z:880.41 (is calculated
Value: 880.35).Theoretical elemental content (%) C66H44N2O:C, 89.97；H,5.03；N,3.18；O,1.82.Survey constituent content
(%): C, 89.96；H,5.04；N,3.19；O,1.81.The above results confirm that obtaining product is target product.
Embodiment 7: the preparation of compound 17
Intermediate D-1 in embodiment 1 is replaced with to the intermediate D-17 of equimolar amounts, other steps are and embodiment
1 is identical, obtains compound 17.Mass spectrum m/z:880.45 (calculated value: 880.35).Theoretical elemental content (%) C66H44N2O:C,
89.97；H,5.03；N,3.18；O,1.82.Survey constituent content (%): C, 90.00；H,5.04；N,3.19；O,1.83.It is above-mentioned
As a result confirm that obtaining product is target product.
Embodiment 8: the preparation of compound 45
Intermediate A -1 in embodiment 1 is replaced with to the intermediate A -45 of equimolar amounts, intermediate C-1 is replaced with
The intermediate C-45 of equimolar amounts, other steps are same as Example 1, obtain compound 45.Mass spectrum m/z:856.42 (is calculated
Value: 856.35).Theoretical elemental content (%) C64H44N2O:C, 89.69；H,5.17；N,3.27；O,1.87.Survey constituent content
(%): C, 89.73；H,5.14；N,3.27；O,1.85.The above results confirm that obtaining product is target product.
Embodiment 9: the preparation of compound 48
Intermediate A -1 in embodiment 1 is replaced with to the intermediate A -45 of equimolar amounts, intermediate C-1 is replaced with
The intermediate C-45 of equimolar amounts, intermediate D-1 are replaced with the intermediate D-4 of equimolar amounts, other steps with embodiment 1
It is identical, obtain compound 48.Mass spectrum m/z:968.55 (calculated value: 968.47).Theoretical elemental content (%) C72H60N2O:C,
89.22；H,6.24；N,2.89；O,1.65.Survey constituent content (%): C, 89.30；H,6.26；N,2.89；O,1.65.It is above-mentioned
As a result confirm that obtaining product is target product.
Embodiment 10: the preparation of compound 89
Intermediate A -1 in embodiment 1 is replaced with to the intermediate A -89 of equimolar amounts, intermediate C-1 is replaced with
The intermediate C-89 of equimolar amounts, other steps are same as Example 1, obtain compound 89.Mass spectrum m/z:814.41 (is calculated
Value: 814.30).Theoretical elemental content (%) C61H38N2O:C, 89.90；H,4.70；N,3.44；O,1.96.Survey constituent content
(%): C, 89.96；H,4.72；N,3.43；O,1.95.The above results confirm that obtaining product is target product.
Embodiment 11: the preparation of compound 92
Intermediate A -1 in embodiment 1 is replaced with to the intermediate A -89 of equimolar amounts, intermediate C-1 is replaced with
The intermediate C-89 of equimolar amounts, intermediate D-1 are replaced with the intermediate D-4 of equimolar amounts, other steps with embodiment 1
It is identical, obtain compound 92.Mass spectrum m/z:926.50 (calculated value: 926.42).Theoretical elemental content (%) C69H54N2O:C,
89.38；H,5.87；N,3.02；O,1.73.Survey constituent content (%): C, 89.43；H,5.86；N,3.04；O,1.75.It is above-mentioned
As a result confirm that obtaining product is target product.
Embodiment 12: the measurement of refractive index
Compound in 1-11 of the embodiment of the present invention is deposited to the film for forming 60nm thickness on organosilicon plate respectively, use is ellipse
Inclined instrument measures it in the refractive index of 620nm, and measurement result is as shown in table 1 below.
Table 1
| Compound | Refractive index (620nm) |
| Compound 1 | 1.91 |
| Compound 4 | 1.89 |
| Compound 5 | 1.90 |
| Compound 6 | 1.84 |
| Compound 9 | 1.88 |
| Compound 13 | 1.85 |
| Compound 17 | 1.84 |
| Compound 45 | 1.92 |
| Compound 48 | 1.88 |
| Compound 89 | 1.85 |
| Compound 92 | 1.84 |
Application Example 13-23: the preparation of luminescent device 1-11
Firstly, with the thickness of 60nm on the ITO (10nm) for being formed in organic substrate/Ag (100nm)/ITO (10nm) layer
Vacuum evaporation NPB forms hole transmission layer；It is on the hole transport layer the CBP and (piq) of 95:5 with weight ratio2Ir(acac)
Vacuum deposition is as luminescent layer, with a thickness of 30nm；Electron transfer layer is formed with the thickness vacuum deposition TPBI of 40nm；With 20nm
Thickness deposition Mg/Ag form cathode；Using the thickness vacuum deposition organic electroluminescent compounds of the present invention of 60nm as light
Removing layer.
Application Example 24-28: the preparation of luminescent device 12-16
Firstly, with the thickness of 60nm on the ITO (10nm) for being formed in organic substrate/Ag (100nm)/ITO (10nm) layer
Vacuum evaporation organic electroluminescent compounds of the present invention form hole transmission layer；It is on the hole transport layer 95:5 with weight ratio
CBP and (piq)2Ir (acac) vacuum deposition is as luminescent layer, with a thickness of 30nm；Come with the thickness vacuum deposition TPBI of 40nm
Form electron transfer layer；Mg/Ag is deposited with the thickness of 20nm to form cathode；It is organic with the thickness vacuum deposition present invention of 60nm
Electroluminescent compounds are as light removing layer.
Comparative example 1: the preparation of luminescent device 17
Difference with Application Example 13-28 is, does not contain light removing layer.
Compound involved in Application Example and comparative example of the present invention is as follows:
The luminescent properties for the organic electroluminescence device that the embodiment of the present invention is prepared are as shown in table 2.
Table 2
The above result shows that organic electroluminescent compounds of the invention are answered as light removing layer and/or hole transmission layer
It is the organic of a kind of function admirable for the luminous efficiency and service life of device in organic electroluminescence device, to can be improved
Luminescent material.
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, these improvement and modification are also fallen within the scope of the present invention.
Claims (10)
1. a kind of organic electroluminescent compounds, which is characterized in that have structure shown in logical formula (I) as follows:
Ar1For structure shown in formula (I-1), Ar2For structure shown in formula (I-2):
Wherein, each R1、R2、R3、R4Independently selected from hydrogen atom, D-atom, halogen atom, the alkyl of C1~C10, C1~
The alkoxy of C10, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 heteroaryl in one
Kind；Or the R1、R2、R3、R4The condensed cyclization of both middle arbitrary neighborhoods；A is selected from 0 to 3 integer, and b, c, d are independent to be selected from 0 to 4
Integer；
Each R5、R6Independently selected from hydrogen atom, D-atom, halogen atom, the alkyl of C1~C10, C1~C10 alkoxy,
One of the aryl of substituted or unsubstituted C6~C30, heteroaryl of substituted or unsubstituted C3~C30；Or the R5、R6
The condensed cyclization of both middle arbitrary neighborhoods；E is selected from 0 to 4 integer, and f is selected from 0 to 3 integer；
Ar3、Ar4Aryl or the Ar independently selected from substituted or unsubstituted C6~C303、Ar4It is fused into the N being connect
Ring.
2. a kind of organic electroluminescent compounds according to claim 1, which is characterized in that the Ar1Selected from following knot
Any one of structure:
3. a kind of organic electroluminescent compounds according to claim 1, which is characterized in that the Ar2Selected from following knot
Any one of structure:
4. a kind of organic electroluminescent compounds according to claim 1, which is characterized in that the Ar1Selected from following institute
Show any one of structure:
5. a kind of organic electroluminescent compounds according to claim 1, which is characterized in that the Ar2Selected from following knot
Any one of structure:
6. a kind of organic electroluminescent compounds according to claim 1, which is characterized in that the Ar3、Ar4Independently
Selected from phenyl, xenyl, terphenyl, naphthalene or Ar3、Ar4Structure as follows is fused into the N being connect:
7. a kind of organic electroluminescent compounds according to claim 1, which is characterized in that in structure as follows
Any one:
8. a kind of organic electroluminescence device comprising organic electroluminescent compounds of any of claims 1-7.
9. organic electroluminescence device according to claim 8, which is characterized in that the organic electroluminescence device includes
Light removing layer, cathode, organic matter layer, anode and substrate, at least one layer in the smooth removing layer and the organic matter layer contain
The described in any item organic electroluminescent compounds of claim 1-7.
10. organic electroluminescence device according to claim 9, which is characterized in that contain hole in the organic matter layer
Transport layer, at least one layer in the smooth removing layer and the hole transmission layer contain that claim 1-7 is described in any item to be had
Organic electro luminescent compounds.
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| CN111718367A (en) * | 2020-07-28 | 2020-09-29 | 吉林奥来德光电材料股份有限公司 | Organic luminescent material and preparation method and application thereof |
| CN114122288A (en) * | 2021-11-12 | 2022-03-01 | 长春海谱润斯科技股份有限公司 | Organic electroluminescent device comprising light extraction layer |
| CN114728947A (en) * | 2020-02-13 | 2022-07-08 | 株式会社Lg化学 | Novel compound and organic light emitting device using the same |
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