CN109912565A - It is a kind of using cyano pyridine as the compound of core and its application in organic electroluminescence device - Google Patents
It is a kind of using cyano pyridine as the compound of core and its application in organic electroluminescence device Download PDFInfo
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Abstract
The invention discloses a kind of using cyano pyridine as the compound of core and its application in organic electroluminescence device, and the compound is using cyano pyridine as core, using carbazole and ring and two fragrant imine groups as branch.The compound have the characteristics that it is intermolecular be not easy to crystallize, be not easy to assemble, film forming it is good.It is applied to the compounds of this invention as emitting layer material on organic electroluminescence device, is showed using the organic electroluminescence device of the compounds of this invention with good photoelectric properties, can preferably adapt to and meet the application requirement of panel manufacturing enterprise.
Description
Technical field
The present invention relates to technical field of semiconductors, more particularly, to it is a kind of using cyano pyridine as the compound of core and its
Application in organic electroluminescence device.
Background technique
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology can both be used to make
New display product is made, production novel illumination product is can be used for, is expected to substitute existing liquid crystal display and fluorescent lighting,
Application prospect is very extensive.Structure of the OLED luminescent device like sandwich, including electrode material film layer, and it is clipped in different electricity
Organic functional material between the film layer of pole, various different function materials are overlapped mutually depending on the application collectively constitutes OLED hair together
Optical device.As current device, when the two end electrodes application voltage to OLED luminescent device, and pass through electric field action organic layer function
Positive and negative charge in energy film layer, positive and negative charge is further compound in luminescent layer, i.e. generation OLED electroluminescent.
Application of the Organic Light Emitting Diode (OLEDs) in terms of large-area flat-plate is shown and is illuminated causes industry and
The extensive concern of art circle.However, traditional organic fluorescence materials can only be shone using 25% singlet exciton to be formed is electrically excited, device
The internal quantum efficiency of part is lower (up to 25%).External quantum efficiency is generally lower than 5%, and there are also very big with the efficiency of phosphorescent devices
Gap.Although phosphor material can efficiently use electricity since the strong SO coupling in heavy atom center enhances intersystem crossing
The singlet exciton formed and Triplet exciton are excited, makes the internal quantum efficiency of device up to 100%.But phosphor material exists
Expensive, stability of material is poor, and device efficiency tumbles the problems such as serious and limits it in the application of OLEDs.Hot activation is prolonged
Slow fluorescence (TADF) material is the third generation luminous organic material developed after organic fluorescence materials and organic phosphorescent material.It should
Class material generally has poor (the △ E of small singlet-tripletST), triplet excitons can be changed by anti-intersystem crossing
It shines at singlet exciton.This can make full use of the singlet exciton and triplet excitons that are electrically excited lower formation, device it is interior
Quantum efficiency can achieve 100%.Meanwhile material structure is controllable, and property is stablized, and it is cheap to be not necessarily to precious metal, in OLEDs
Field has a extensive future.
Although theoretically 100% exciton utilization rate may be implemented in TADF material, following problem there are in fact: (1)
T1 the and S1 state for designing molecule has strong CT feature, very small S1-T1 state energy gap, although can realize by TADF process
High T1→S1State exciton conversion ratio, but low S1 state radiation transistion rate is also resulted in, consequently it is difficult to have both (or realizing simultaneously)
High exciton utilization rate and high fluorescent radiation efficiency；(2) even if having used doping device to mitigate T exciton concentration quenching effect, greatly
Efficiency roll-off is serious at higher current densities for the device of most TADF materials.Current OLED is shown to the actual demand of Lighting Industry
For, the development of OLED material is also far from enough at present, lags behind the requirement of panel manufacturing enterprise, more as material enterprise development
High performance organic functional material is particularly important.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, the applicant provides a kind of using cyano pyridine as the chemical combination of core
Object and its application in organic electroluminescence device.The compounds of this invention is based on TADF mechanism using cyano-containing pyridine as core
The heart is applied to Organic Light Emitting Diode as emitting layer material, and the device that the present invention makes has good photoelectric properties, can
Meet the requirement of panel manufacturing enterprise.
Technical scheme is as follows: a kind of using cyano pyridine as the compound of core, the structure of the compound
As shown in general formula (1):
In general formula (1), X1、X2、X3、X4、X5Independently be expressed as nitrogen-atoms or carbon atom；And X1、X2、X3、X4、X5
In up to 3 nitrogen-atoms；
In general formula (1), work as X1、X2、X3、X4Or X5When for carbon atom, R1、R2、R3、R4、R5Independently be expressed as hydrogen original
Son, cyano, substituted or unsubstituted C6-60Aryl contains one or more heteroatomic substituted or unsubstituted 5-60 member heteroaryls
Base, and wherein a minimum of 1 be cyano；The hetero atom is nitrogen, oxygen or sulphur；Work as X1、X2、X3、X4Or X5When for nitrogen-atoms, R1、
R2、R3、R4、R5It is not expressed as substituent group；
In general formula (1), Ar is expressed as singly-bound, substituted or unsubstituted C6-60Arlydene contains one or more hetero atoms
Substituted or unsubstituted 5~60 yuan of heteroarylidenes；The hetero atom is nitrogen, oxygen or sulphur；
In general formula (1), R6It is expressed as structure shown in general formula (2) or general formula (3)；
In general formula (1), R7It is expressed as structure shown in general formula (4), general formula (5) or general formula (6)；
In general formula (3), general formula (6), R8、R9、R10、R11Independently be expressed as substituted or unsubstituted C6-60Aryl,
Contain one or more heteroatomic substituted or unsubstituted 5~60 unit's heteroaryls；The hetero atom is nitrogen, oxygen or sulphur；
In general formula (5), X6It is expressed as oxygen atom, sulphur atom, C1-10Alkylidene, the aryl of linear or branched alkyl group substitution take
One of the imido grpup that the alkylidene in generation, alkyl-substituted imido grpup or aryl replace；
General formula (4), general formula (5) pass through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key is connected with general formula (1) and ring.
On the basis of above scheme, the present invention can also do following improvement.
Preferably, a kind of using cyano pyridine as the compound of core, the structure of the compound such as general formula (7), general formula
(8), shown in general formula (9), general formula (10) or general formula (11):
Preferably, a kind of using cyano pyridine as the compound of core, work as X1、X2、X3、X4Or X5When for carbon atom, R1、
R2、R3、R4、R5Independently be expressed as hydrogen atom, cyano, phenyl, xenyl, naphthalene or pyridyl group, and wherein a minimum of 1
A is cyano；Ar is expressed as one kind of singly-bound, phenylene, biphenylene, naphthylene or anthrylene, R8、R9Expression independently
For one of phenyl, naphthalene, dibiphenylyl, terphenyl, dibenzofuran group, 9,9- dimethyl fluorene or N- phenyl carbazole.
Preferably, a kind of using cyano benzene as the compound of core, in general formula (1)It indicates are as follows: In any one.
Preferably, a kind of using cyano pyridine as the compound of core, it is describedIt indicates are as follows:
In any one.
Preferably, a kind of using cyano pyridine as the compound of core, the concrete structure formula of the compound are as follows:
In any one.
The present invention also provides a kind of using cyano pyridine as the method for the compound of core, the reaction occurred in preparation process
Equation is:
When Ar indicates singly-bound:
Specific preparation step are as follows:
Raw material E and intermediate M1 are dissolved in dry toluene, Pd is added after deoxygenation2(dba)3, tri-tert phosphorus and tertiary fourth
Sodium alkoxide, under an inert atmosphere 95~110 DEG C of 10~24 hours of reaction constantly monitor reaction process with TLC in reaction process, to
After raw material fully reacting, filtrate is rotated and removes dry toluene by cooling, filtering, and crude product crosses silicagel column, obtains target chemical combination
Object；The dosage of the dry toluene is that every gram of intermediate M1 uses 30~50mL toluene, and raw material E and the molar ratio of intermediate M1 are
1:1.0~1.5, Pd2(dba)3Molar ratio with raw material E is 0.006~0.02:1, and the molar ratio of tri-tert-butylphosphine and raw material E is
The molar ratio of 0.006~0.02:1, sodium tert-butoxide and bromo-derivative E are 2.0~3.0:1；
When Ar does not indicate singly-bound:
Intermediate M2 and raw material E are dissolved in the mixed solution of toluene and ethyl alcohol, Pd (PPh is added after deoxygenation3)4With
K2CO3, 95~110 DEG C of 10~24 hours of reaction under an inert atmosphere constantly monitor reaction process with TLC in reaction process, to
After raw material fully reacting, filtrate is rotated and removes solvent by cooling, filtering, and crude product crosses silicagel column, obtains target compound；
Wherein, the dosage of the toluene and ethyl alcohol is that every gram of intermediate M2 uses 30~50mL toluene and 5~10mL second
The molar ratio of alcohol, raw material E and intermediate M2 are (1~1.5): 1, Pd (PPh3)4With the molar ratio of intermediate M2 be (0.006~
0.02): 1, K2CO3Molar ratio with intermediate M2 is (1.5~2): 1.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device includes at least one layer of function
Layer is containing described using cyano pyridine as the compound of core.
Preferably, a kind of organic electroluminescence device, including luminescent layer, the luminescent layer contain described with cyano azepine
Benzene is the compound of core.
The present invention also provides a kind of illumination or display elements, including the organic electroluminescence device.
The present invention is beneficial to be had the technical effect that
For the compounds of this invention using cyano pyridine as parent nucleus, cyano azepine phenyl group is in approximately the same plane, has stronger
Rigidity, therefore have better film forming；Cyano azepine phenyl group is strong electron-withdrawing group group, with carbazole and ring and two fragrant imines
Class group can form stronger electric charge transfer effect, and the energy level difference with lesser S1 state and T1 state, thus in thermostimulation item
Reversed intersystem crossing is realized under part, and under conditions of energy level meets while there is bipolarity and TADF effect；Simultaneously because cyano
Chemical stability and thermal stability, cyano pyridine have preferable prospects for commercial application, be suitable as shine layer main body material
Material uses.Further, the difference designed according to material molecule, such compound can also be used as the doping material of emitting layer material
Material uses.
The compounds of this invention as OLED luminescent device emitting layer material in use, device current efficiency, power effect
Rate and external quantum efficiency are greatly improved；Meanwhile device lifetime is promoted clearly.Compound material of the present invention
Material has good application effect in OLED luminescent device, has good industrialization prospect.
Detailed description of the invention
Fig. 1 is the device architecture schematic diagram of the compounds of this invention application；Wherein, 1 is transparent substrate layer, and 2 be ito anode
Layer, 3 be hole injection layer, and 4 be hole transmission layer, and 5 be luminescent layer, and 6 be electron transfer layer, and 7 be electron injecting layer, and 8 be cathode
Reflection electrode layer.Fig. 2 is current efficiency variation with temperature curve.
Specific embodiment
Embodiment 1:
It provides in general formula (1) firstSynthetic route are as follows:
It weighs raw material I to be dissolved in acetic acid, is cooled to 0 DEG C with ice salt bath；Bromine is weighed to be dissolved in glacial acetic acid, be slowly added dropwise to
In acetic acid solution containing nitro compound raw material I, reaction is stirred at room temperature 6~12 hours, samples contact plate, display is surplus without raw material I
Remaining, fully reacting is added dropwise sodium hydrate aqueous solution to the aobvious neutrality of solution, is extracted with dichloromethane, takes organic phase after reaction
Filtering, filtrate decompression rotate to no fraction, cross silicagel column, obtain intermediate S1；In above-mentioned reaction, the molar ratio of raw material I and bromine
Example is 1:1~3；Every gram of raw material I uses 30~50mL acetic acid；
Weigh raw material II and intermediate S1, dissolved with toluene, under an inert atmosphere, be added potassium carbonate, tetra-triphenylphosphine palladium,
The mixed solution of second alcohol and water, stirring are warming up to 110~120 DEG C, react 10~24 hours, sample contact plate, show intermediate S1
Residue, fully reacting are cooled to room temperature after reaction, and filtering, filtrate layered takes organic phase vacuum rotary steam to no fraction, mistake
Silicagel column obtains intermediate S2；In above-mentioned reaction, the molar ratio of intermediate S1 and raw material II is 1:1~2；Intermediate S1 and carbon
The molar ratio of sour potassium is 1:1~3；The molar ratio of intermediate S1 and tetra-triphenylphosphine palladium is 1:0.01~0.05；Every gram of intermediate
S1 uses 30~50mL toluene；The mixed liquor that every gram of intermediate S1 is 1:1 using 15~25mL water and ethyl alcohol volume ratio；
Under an inert atmosphere, intermediate S2 is dissolved in o-dichlorohenzene, adds triphenylphosphine, stirred at 170~190 DEG C
It mixes reaction 12~16 hours, samples contact plate, display intermediate S2 is remaining, and fully reacting is cooled to room temperature after reaction, mistake
Filter, filtrate decompression rotate to no fraction, cross silicagel column, obtain intermediate M1；In above-mentioned reaction, intermediate S2 rubs with triphenylphosphine
You are than being 1:1~2；Every gram of intermediate S2 uses 30~50mL o-dichlorohenzene；
Under nitrogen protection, intermediate M1, raw material II I, sodium tert-butoxide, Pd are successively weighed2(dba)3, tri-tert-butylphosphine, use
Toluene is stirred, and is heated to 110~120 DEG C, back flow reaction 12~24 hours, is sampled contact plate, and display is remaining without intermediate M1,
Fully reacting；Cooled to room temperature, filtering, filtrate carry out vacuum rotary steam to no fraction, cross neutral silica gel column, obtain intermediate
S3.In above-mentioned reaction, intermediate M1 and III molar ratio of raw material are 1:1~2；The molar ratio of intermediate M1 and sodium tert-butoxide is 1:1
~3；Intermediate M1 and Pd2(dba)3Molar ratio be 1:0.01~0.05；The molar ratio of intermediate M1 and tri-tert-butylphosphine is 1:
0.01~0.05；Every gram of intermediate M1 uses 30~50mL toluene；
In a nitrogen atmosphere, intermediate S3, bis- (pinacol combined) two boron, Pd (dppf) Cl are weighed2First is dissolved in potassium acetate
It in benzene, is reacted 12~24 hours at 100~120 DEG C, samples contact plate, display is remaining without intermediate S3, and fully reacting is naturally cold
But, it filters, filtrate revolving obtains crude product, crosses neutral silica gel column, obtain intermediate M2；Wherein, intermediate S3 and it is bis- (frequency where
Alcohol closes) molar ratios of two boron is 2:1~1.5, intermediate S3 and Pd (dppf) Cl2Molar ratio be 1:0.01~0.05, it is intermediate
The molar ratio of body S3 and potassium acetate is 1:2~2.5, and every gram of intermediate M1 uses 30~50mL toluene.
By taking intermediate M2-2 as an example:
In the there-necked flask of 250ml, raw material I-1,100ml acetic acid of 0.04mol is added, stirring and dissolving is dropped with ice salt bath
Temperature is to 0 DEG C；Weigh 0.05mol Br2It is dissolved in 50ml acetic acid, the acetic acid solution of bromine is slowly added dropwise into above-mentioned reaction system, is dripped
It after adding, is warmed to room temperature, is stirred to react 12 hours；Contact plate is sampled, display is remaining without raw material I-1, fully reacting；Add NaOH water
Solution neutralization reaction liquid is extracted with dichloromethane to neutrality, is layered, takes organic phase to filter, filtrate decompression is rotated to no fraction, mistake
Neutral silica gel column obtains intermediate S1-2；Elemental analysis structure C10H6BrNO2: theoretical value C, 47.65；H,2.40；Br,
31.70；N,5.56；Test value: C, 47.65；H,2.40；Br,31.70；N,5.55；ESI-MS (m/z) (M+): theoretical value is
250.96 measured value 251.66.
In the there-necked flask of 250ml, lead under nitrogen protection, addition 0.05mol intermediate S1-2,0.06mol raw material II -2,
100ml toluene, is stirred, and adds 0.0025mol Pd (PPh3)4, 0.075mol potassium carbonate, 50ml water and ethyl alcohol 1:1
Mixed liquor, stirring are warming up to 120 DEG C, back flow reaction 24 hours, sample contact plate, display is remaining without intermediate S1-2, fully reacting；
Cooled to room temperature, filtering, filtrate layered take organic phase vacuum rotary steam to no fraction, cross neutral silica gel column, obtain intermediate
S2-2；Elemental analysis structure C22H15NO2: theoretical value C, 81.21；H,4.65；N,4.30；Test value: C, 81.21；H,4.65；N,
4.31；ESI-MS (m/z) (M+): theoretical value 325.11, measured value 325.44.
In the there-necked flask of 250ml, lead under nitrogen protection, addition 0.04mol intermediate S2-2,0.05mol triphenylphosphine,
100ml o-dichlorohenzene, is stirred, and is heated to 180 DEG C, reacts 12 hours, samples contact plate, and display is remaining without intermediate S2-2,
Fully reacting；Cooled to room temperature, filtering, filtrate decompression rotate to no fraction, cross neutral silica gel column, obtain intermediate M1-
2；Elemental analysis structure C22H15N: theoretical value C, 90.07；H,5.15；N,4.77；Test value: C, 90.08；H,5.15；N,
4.76；ESI-MS (m/z) (M+): theoretical value 293.12, measured value 293.22.
In the there-necked flask of 250ml, lead under nitrogen protection, 0.03mol intermediate M1-2,0.036mol Isosorbide-5-Nitrae-two is added
Bromobenzene, 150ml toluene, are stirred, and add 0.09mol sodium tert-butoxide, 0.002molPd2(dba)3, the tertiary fourth of 0.002mol tri-
Base phosphine is heated with stirring to 115 DEG C, back flow reaction 24 hours, samples contact plate, display is remaining without intermediate M1-2, fully reacting；From
It is so cooled to room temperature, filters, filtrate decompression is rotated to no fraction, is crossed neutral silica gel column, is obtained intermediate S3-2；Elemental analysis knot
Structure C28H18BrN: theoretical value C, 75.01；H,4.05；Br,17.82；N,3.12；Test value: C, 75.02；H,4.05；Br,
17.82；N,3.11；ESI-MS (m/z) (M+): theoretical value 447.06, measured value 447.51.
In the there-necked flask of 250ml, lead under nitrogen protection, 0.03mol intermediate S3-2,0.036mol Isosorbide-5-Nitrae-two is added
Bromobenzene, 150ml toluene, are stirred, and add 0.09mol sodium tert-butoxide, 0.002molPd2(dba)3, the tertiary fourth of 0.002mol tri-
Base phosphine is heated with stirring to 115 DEG C, back flow reaction 24 hours, samples contact plate, display is remaining without intermediate S3-2, fully reacting；From
It is so cooled to room temperature, filters, filtrate decompression is rotated to no fraction, is crossed neutral silica gel column, is obtained intermediate M2-2；Elemental analysis knot
Structure C28H20BNO2: theoretical value C, 81.37；H,4.88；B,2.62；N,3.39；Test value: C, 81.37；H,4.88；B,2.62；N,
3.38；ESI-MS (m/z) (M+): theoretical value 413.16, measured value 413.42.
Intermediate M1 and M2 are prepared by the synthetic schemes of intermediate M2-2；Specific structure employed in preparation process is such as
Shown in table 1:
Table 1
Embodiment 2: the synthesis of compound 7:
0.01mol raw material E-1 and 0.012mol intermediate M1-1 are dissolved in 150mL dry toluene, are added after deoxygenation
0.0005mol Pd2(dba)3, 0.015mol tri-tert phosphorus and 0.02mol sodium tert-butoxide, 110 DEG C of reactions under an inert atmosphere
24 hours constantly monitor reaction process with TLC in reaction process, and after raw material fully reacting, filtrate is revolved in cooling, filtering
Solvent is evaporated off, crude product crosses silicagel column, obtains target product；Elemental analysis structure (molecular formula C46H30N4): theoretical value C,
86.49；H,4.73；N,8.77；Test value: C, 86.49；H,4.73；N,8.78；ESI-MS (m/z) (M+): theoretical value is
638.25 measured value 638.66.
Embodiment 3: the synthesis of compound 17:
0.01mol intermediate M2-2 and 0.012mol raw material E-1 is dissolved in the 150mL (V of toluene and ethyl alcoholToluene: VEthyl alcohol=
5:1) in mixed solution, 0.0002mol Pd (PPh is added after deoxygenation3)4With 0.02mol K2CO3, 110 DEG C under an inert atmosphere
It reacts 24 hours, constantly monitors reaction process with TLC in reaction process, after raw material fully reacting, cooling, filtering will be filtered
Liquid revolving removes solvent, and crude product crosses silicagel column, obtains intermediate target product；Elemental analysis structure (molecular formula C46H29N3):
Theoretical value C, 88.58；H,4.69；N,6.74；Test value: C, 88.56；H,4.69；N,6.75；ESI-MS (m/z) (M+): theoretical
Value is 623.24, measured value 623.42.
Embodiment 4: the synthesis of compound 33:
The preparation method of compound 33 is with embodiment 3, the difference is that replacing intermediate M2-2 using intermediate M2-3.
Elemental analysis structure (molecular formula C46H29N3): theoretical value C, 88.58；H,4.69；N,6.74；Test value: C, 88.57；H,4.69；
N,6.74；ESI-MS (m/z) (M+): theoretical value 623.24, measured value 623.45.
Embodiment 5: the synthesis of compound 39:
The preparation method of compound 39 is with embodiment 3, the difference is that replacing intermediate M2-2 using intermediate M2-1.
Elemental analysis structure (molecular formula C52H34N4): theoretical value C, 87.37；H,4.79；N,7.84；Test value: C, 87.36；H,4.79；
N,7.85。ESI-MS(m/z)(M+): theoretical value 714.28, measured value 714.68.
Embodiment 6: the synthesis of compound 51:
The preparation method of compound 51 is with embodiment 2, the difference is that replacing intermediate M1-1 using intermediate M1-3.
Elemental analysis structure (molecular formula C54H35N5): theoretical value C, 86.03；H,4.68；N,9.29；Test value: C, 86.04；H,4.68；
N,9.28。ESI-MS(m/z)(M+): theoretical value 753.29, measured value 753.61.
Embodiment 7: the synthesis of compound 62:
The preparation method of compound 62 is with embodiment 2, the difference is that intermediate M1-1 is replaced using intermediate M1-4,
Raw material E-1 is replaced using raw material E-2.Elemental analysis structure (molecular formula C50H35N5): theoretical value C, 85.08；H,5.00；N,
9.92；Test value: C, 85.07；H,5.00；N,9.93.ESI-MS(m/z)(M+): theoretical value 705.29, measured value are
705.64。
Embodiment 8: the synthesis of compound 72:
The preparation method of compound 72 is with embodiment 3, the difference is that replacing intermediate M2-2 using intermediate M2-4.
Elemental analysis structure (molecular formula C54H34N4O): theoretical value C, 85.92；H,4.54；N,7.42；Test value: C, 85.92；H,
4.54；N,7.41.ESI-MS(m/z)(M+): theoretical value 754.27, measured value 754.56.
Embodiment 9: the synthesis of compound 85:
The preparation method of compound 85 is with embodiment 3, the difference is that replacing intermediate M2-2 using intermediate M2-5.
Elemental analysis structure (molecular formula C57H40N4): theoretical value C, 87.66；H,5.16；N,7.17；Test value: C, 87.67；H,5.16；
N,7.16。ESI-MS(m/z)(M+): theoretical value 780.33, measured value 780.66.
Embodiment 10: the synthesis of compound 96:
The preparation method of compound 96 is with embodiment 3, the difference is that replacing intermediate M2-2 using intermediate M2-6.
Elemental analysis structure (molecular formula C58H38N4): theoretical value C, 88.07；H,4.84；N,7.08；Test value: C, 88.07；H,4.84；
N,7.09。ESI-MS(m/z)(M+): theoretical value 790.31, measured value 790.88.
Embodiment 11: the synthesis of compound 106:
The preparation method of compound 106 is with embodiment 2, the difference is that replacing intermediate M1- using intermediate M1-8
1.Elemental analysis structure (molecular formula C55H38N4): theoretical value C, 87.50；H,5.07；N,7.42；Test value: C, 87.50；H,
5.07；N,7.43.ESI-MS(m/z)(M+): theoretical value 754.31, measured value 754.61.
Embodiment 12: the synthesis of compound 123:
The preparation method of compound 123 is with embodiment 3, the difference is that replacing raw material E-1 using raw material E-3.Element
Analyze structure (molecular formula C46H29N3): theoretical value C, 88.58；H,4.69；N,6.74；Test value: C, 88.58；H,4.69；N,
6.73。ESI-MS(m/z)(M+): theoretical value 623.24, measured value 623.24.
Embodiment 13: the synthesis of compound 138:
The preparation method of compound 138 is with embodiment 3, the difference is that replacing intermediate M2- using intermediate M2-1
2, raw material E-3 replace raw material E-1.Elemental analysis structure (molecular formula C52H34N4): theoretical value C, 87.37；H,4.79；N,7.84；
Test value: C, 87.36；H,4.79；N,7.85.ESI-MS(m/z)(M+): theoretical value 714.28, measured value 714.93.
Embodiment 14: the synthesis of compound 147:
The preparation method of compound 147 is with embodiment 2, the difference is that replacing raw material E-1 using raw material E-4.Element
Analyze structure (molecular formula C47H29N5): theoretical value C, 85.05；H,4.40；N,10.55；Test value: C, 85.06；H,4.40；N,
10.54。ESI-MS(m/z)(M+): theoretical value 663.24, measured value 663.77.
Embodiment 15: the synthesis of compound 162:
The preparation method of compound 162 is with embodiment 3, the difference is that replacing intermediate using using intermediate M2-3
M2-2, raw material E-4 replace raw material E-1.Elemental analysis structure (molecular formula C47H28N4): theoretical value C, 87.01；H,4.35；N,
8.64；Test value: C, 87.02；H,4.35；N,8.63.ESI-MS(m/z)(M+): theoretical value 648.23, measured value are
648.81。
Embodiment 16: the synthesis of compound 174:
The preparation method of compound 174 is with embodiment 2, the difference is that replacing intermediate M1- using intermediate M1-9
1, raw material E-5 replace raw material E-1.Elemental analysis structure (molecular formula C44H25N7): theoretical value C, 81.09；H,3.87；N,15.04；
Test value: C, 81.08；H,3.87；N,15.05.ESI-MS(m/z)(M+): theoretical value 651.22, measured value 651.77.
Embodiment 17: the synthesis of compound 185:
The preparation method of compound 185 is with embodiment 3, the difference is that replacing intermediate M2- using intermediate M2-7
2, raw material E-6 replace raw material E-1.Elemental analysis structure (molecular formula C46H31N5): theoretical value C, 84.51；H,4.78；N,10.71；
Test value: C, 84.52；H,4.78；N,10.70.ESI-MS(m/z)(M+): theoretical value 653.26, measured value 653.79.
Embodiment 18: the synthesis of compound 191:
The preparation method of compound 191 is with embodiment 2, the difference is that intermediate M1-8 replaces intermediate M1-1, it is former
Expect that E-5 replaces raw material E-1.Elemental analysis structure (molecular formula C45H28N6): theoretical value C, 82.80；H,4.32；N,12.87；Test
Value: C, 82.81；H,4.32；N,12.87.ESI-MS(m/z)(M+): theoretical value 652.24, measured value 652.88.
Embodiment 19: the synthesis of compound 202:
The preparation method of compound 202 is with embodiment 2, the difference is that intermediate M1-11 replaces intermediate M1-1.Member
Element analysis structure (molecular formula C54H37N5): theoretical value C, 85.80；H,4.93；N,9.26；Test value: C, 85.80；H,4.93；N,
9.27。ESI-MS(m/z)(M+): theoretical value 755.30, measured value 755.79.
The compounds of this invention can be used as emitting layer material use, to the compounds of this invention 7, compound 85, compound
162, current material CBP carries out the test of hot property, luminescent spectrum and cyclic voltammetric stability, and test result is as shown in table 2.
Table 2
| Compound | Td(℃) | λPL(nm) | Cyclic voltammetric stability |
| Compound 7 | 421 | 465 | It is excellent |
| Compound 85 | 440 | 456 | It is excellent |
| Compound 162 | 425 | 470 | It is excellent |
| Material C BP | 353 | 369 | Difference |
Note: thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in the TGA-50H heat of Japanese Shimadzu Corporation
It is measured on weight analysis instrument, nitrogen flow 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, opens up Pu Kang using Japan
The measurement of SR-3 spectroradiometer；Cyclic voltammetric stability be by cyclic voltammetry observe material redox characteristic come into
Row identification；Test condition: test sample is dissolved in the methylene chloride and acetonitrile mixed solvent that volume ratio is 2:1, concentration 1mg/mL, electricity
Solving liquid is the tetrabutyl ammonium tetrafluoroborate of 0.1M or the organic solution of hexafluorophosphate.Reference electrode is Ag/Ag+ electricity
Pole is titanium plate to electrode, and working electrode is ITO electrode, and cycle-index is 20 times, meets 0.9≤Ipa/Ipc≤1.1, then recycles
Volt-ampere stability is excellent, is otherwise difference, and wherein Ipa is oxidation peak current, and Ipc is reduction peak current.
By upper table data it is found that the compounds of this invention has preferable oxidation-reduction stability, higher thermal stability is closed
Suitable luminescent spectrum, so that getting a promotion using the compounds of this invention as the OLED device efficiency of emitting layer material and service life.
By the following examples 1~18 and Comparative Examples 1 and 2,3 the present invention will be described in detail synthesis compounds be used as luminescent layer in the devices
The application effect of material of main part.The structure composition of each embodiment obtained device is as shown in table 3.The test result of obtained device is shown in Table
Shown in 4.
Device embodiments 1
2/ hole injection layer of transparent substrate layer 1/ITO anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4
(TAPC, thickness 80nm)/luminescent layer 5 (the weight ratio blending of compound 7 and GD19 according to 100:5, thickness 40nm)/electron-transport
Layer 6 (TPBI, thickness 40nm)/electron injecting layer, 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).The material being related to
Structural formula is as follows:
Specific preparation process is as follows:
Transparent substrate layer 1 is transparent substrate, such as transparent PI film, glass.Ito anode layer 2 (film thickness 150nm) is carried out
Washing successively carries out neutralizing treatment, pure water, drying, then carry out ultraviolet-ozone washing to remove the transparent surface ITO
Organic residue.On having carried out the ito anode layer 2 after above-mentioned washing, using vacuum deposition apparatus, vapor deposition film thickness is 10nm
Molybdenum trioxide MoO3It is used as hole injection layer 3.And then the TAPC of 80nm thickness is deposited as hole transmission layer 4.On
After stating hole mobile material vapor deposition, the luminescent layer 5 of OLED luminescent device is made, structure includes that OLED luminescent layer 5 is made
Use material compound 7 as material of main part, for GD19 as dopant material, dopant material doping ratio is 5% weight ratio, luminescent layer
Film thickness is 40nm.After above-mentioned luminescent layer 5, continuation vacuum evaporation electron transport layer materials are TPBI.The vacuum of the material is steamed
Plating film thickness is 40nm, this layer is electron transfer layer 6.On electron transfer layer 6, by vacuum deposition apparatus, production film thickness is 1nm
Lithium fluoride (LiF) layer, this layer be electron injecting layer 7.On electron injecting layer 7, by vacuum deposition apparatus, making film thickness is
Aluminium (Al) layer of 80nm, this layer are the use of cathode reflection electrode layer 8.After completing OLED luminescent device as described above, with known
Driving circuit anode and cathode is connected, the current efficiency of measurement device and the service life of device.
Table 3
Table 4
| Device code name | Current efficiency | The LT95 service life | Device code name | Current efficiency | The LT95 service life |
| Embodiment 1 | 10.4 | 60 | Embodiment 11 | 35.4 | 67 |
| Embodiment 2 | 10.6 | 62 | Embodiment 12 | 34.9 | 80 |
| Embodiment 3 | 10.9 | 54 | Embodiment 13 | 35.7 | 65 |
| Embodiment 4 | 11.4 | 56 | Embodiment 14 | 56.6 | 89 |
| Embodiment 5 | 11.2 | 64 | Embodiment 15 | 57.0 | 90 |
| Embodiment 6 | 10.9 | 72 | Embodiment 16 | 57.4 | 87 |
| Embodiment 7 | 11.0 | 56 | Embodiment 17 | 56.8 | 96 |
| Embodiment 8 | 35.8 | 77 | Embodiment 18 | 55.8 | 90 |
| Embodiment 9 | 35.6 | 65 | Comparative example 1 | 6.5 | 3.8 |
| Embodiment 10 | 35.0 | 76 | Comparative example 2 | 24.6 | 4.3 |
| Comparative example 3 | 25.1 | 7.8 |
Illustrate: the current efficiency of comparative example 1 is 6.5cd/A (@10mA/cm2)；LT95 life time decay under 5000nit brightness
For 3.8Hr.The current efficiency of comparative example 2 is 24.6cd/A (@10mA/cm2)；LT95 life time decay is under 5000nit brightness
4.3Hr.The current efficiency of comparative example 3 is 25.1cd/A (@10mA/cm2)；LT95 life time decay is under 5000nit brightness
7.8Hr.Life-span test system is owner of the present invention and the OLED device life-span tester that Shanghai University is studied jointly.
By the result of table 4 can be seen that compound of the present invention can be applied to OLED luminescent device production, and with than
It is compared compared with example 1,2,3, the driving service life that either efficiency or service life obtain larger change, especially device obtains biggish
It is promoted.
From the point of view of the test data provided by the embodiment, the compounds of this invention is as emitting layer material in OLED luminescent device
In have good application effect, have good industrialization prospect.The OLED device of further material preparation of the present invention exists
Efficiency is also more stable when low operating temperatures, by device embodiments 1,9,17 and device comparative example 1, comparative example 2, comparative example 3-
10~80 DEG C of sections carry out efficiency test, and acquired results are as shown in table 5 and Fig. 2.
Table 5
From the data of table 5 and Fig. 2 it is found that device embodiments 1,9,17 are material of the present invention and the device that known materials are arranged in pairs or groups
Structure is compared with device comparative example 1, comparative example 2, comparative example 3, and not only Efficiency at Low Temperature is high, but also in temperature elevation process, effect
Rate steadily increases.
Although disclosing the present invention by embodiment and preferred embodiment, it should be appreciated that it is public that the present invention is not limited to institutes
The embodiment opened.On the contrary, it will be understood by those skilled in the art that it is intended to various modifications and similar arrangement.Therefore, institute
Attached the scope of the claims should be consistent with widest explanation to cover all such modifications and similar arrangement.
Claims (10)
1. a kind of using cyano pyridine as the compound of core, which is characterized in that the structure of the compound such as general formula (1) institute
Show:
In general formula (1), X1、X2、X3、X4、X5Independently be expressed as nitrogen-atoms or carbon atom；And X1、X2、X3、X4、X5In at most
For 3 nitrogen-atoms；
In general formula (1), work as X1、X2、X3、X4Or X5When for carbon atom, R1、R2、R3、R4、R5Independently be expressed as hydrogen atom, cyanogen
Base, substituted or unsubstituted C6-60Aryl contains one or more heteroatomic substituted or unsubstituted 5-60 unit's heteroaryls, and
Wherein a minimum of 1 is cyano；The hetero atom is nitrogen, oxygen or sulphur；Work as X1、X2、X3、X4Or X5When for nitrogen-atoms, R1、R2、R3、
R4、R5It is not expressed as substituent group；
In general formula (1), Ar is expressed as singly-bound, substituted or unsubstituted C6-60Arlydene contains one or more heteroatomic substitutions
Or unsubstituted 5~60 yuan of heteroarylidenes；The hetero atom is nitrogen, oxygen or sulphur；
In general formula (1), R6It is expressed as structure shown in general formula (2) or general formula (3)；
In general formula (1), R7It is expressed as structure shown in general formula (4), general formula (5) or general formula (6)；
In general formula (3), general formula (6), R8、R9、R10、R11Independently be expressed as substituted or unsubstituted C6-60Aryl contains one
A or multiple heteroatomic substituted or unsubstituted 5~60 unit's heteroaryls；The hetero atom is nitrogen, oxygen or sulphur；
In general formula (5), X6It is expressed as oxygen atom, sulphur atom, C1-10Alkylidene, the aryl of linear or branched alkyl group substitution replace
One of the imido grpup that alkylidene, alkyl-substituted imido grpup or aryl replace；
General formula (4), general formula (5) pass through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key is connected with general formula (1) and ring.
2. according to claim 1 a kind of using cyano pyridine as the compound of core, which is characterized in that the compound
Structure such as general formula (7), general formula (8), general formula (9), shown in general formula (10) or general formula (11):
3. according to claim 1 a kind of using cyano pyridine as the compound of core, which is characterized in that work as X1、X2、X3、
X4Or X5When for carbon atom, R1、R2、R3、R4、R5Independently be expressed as hydrogen atom, cyano, phenyl, xenyl, naphthalene or pyrrole
Piperidinyl, and wherein a minimum of 1 be cyano；Ar is expressed as one kind of singly-bound, phenylene, biphenylene, naphthylene or anthrylene,
R8、R9Independently be expressed as phenyl, naphthalene, dibiphenylyl, terphenyl, dibenzofuran group, 9,9- dimethyl fluorene or N-
One of phenyl carbazole.
4. according to claim 1 a kind of using cyano benzene as the compound of core, which is characterized in that in general formula (1)It indicates are as follows:
In any one.
5. according to claim 1 a kind of using cyano pyridine as the compound of core, which is characterized in that describedIt indicates are as follows:
In any one.
6. according to claim 1 a kind of using cyano pyridine as the compound of core, which is characterized in that the compound
Concrete structure formula are as follows:
In any one.
7. a kind of any one of claim 1~6 for preparing is described a kind of using cyano pyridine as the method for the compound of core, special
Sign is that the reaction equation occurred in preparation process is:
When Ar indicates singly-bound:
Specific preparation step are as follows:
Raw material E and intermediate M1 are dissolved in dry toluene, Pd is added after deoxygenation2(dba)3, tri-tert phosphorus and the tert-butyl alcohol
Sodium, under an inert atmosphere 95~110 DEG C of 10~24 hours of reaction constantly monitor reaction process with TLC in reaction process, to original
After expecting fully reacting, filtrate is rotated and removes dry toluene by cooling, filtering, and crude product crosses silicagel column, obtains target compound；
The dosage of the dry toluene is that every gram of intermediate M1 uses 30~50mL toluene, and the molar ratio of raw material E and intermediate M1 is 1:
1.0~1.5, Pd2(dba)3Molar ratio with raw material E is 0.006~0.02:1, and the molar ratio of tri-tert-butylphosphine and raw material E is
The molar ratio of 0.006~0.02:1, sodium tert-butoxide and bromo-derivative E are 2.0~3.0:1；
When Ar does not indicate singly-bound:
Intermediate M2 and raw material E are dissolved in the mixed solution of toluene and ethyl alcohol, Pd (PPh is added after deoxygenation3)4And K2CO3,
95~110 DEG C of 10~24 hours of reaction under inert atmosphere constantly monitor reaction process with TLC in reaction process, anti-to raw material
After answering completely, filtrate is rotated removing solvent by cooling, filtering, and crude product crosses silicagel column, obtains target compound；
Wherein, the dosage of the toluene and ethyl alcohol is that every gram of intermediate M2 uses 30~50mL toluene and 5~10mL ethyl alcohol, former
The molar ratio for expecting E and intermediate M2 is (1~1.5): 1, Pd (PPh3)4Molar ratio with intermediate M2 is (0.006~0.02):
1, K2CO3Molar ratio with intermediate M2 is (1.5~2): 1.
8. a kind of organic electroluminescence device, which is characterized in that the organic electroluminescence device includes at least one layer of functional layer
It is described in any item using cyano pyridine as the compound of core containing claim 1~6.
9. a kind of organic electroluminescence device as claimed in claim 7, including luminescent layer, which is characterized in that the luminescent layer
It is described in any item using cyano pyridine as the compound of core containing claim 1~6.
10. a kind of illumination or display element, which is characterized in that including the organic electroluminescent as described in claim 8-9 is any
Device.
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|---|---|---|---|---|
| CN113224247A (en) * | 2021-02-19 | 2021-08-06 | 冠能光电材料(深圳)有限责任公司 | Pyridine-3, 5-dinitrile-based electroluminescent material and application thereof in organic light-emitting device |
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