CN106467548B - A kind of compound containing benzimidazole and its application - Google Patents
A kind of compound containing benzimidazole and its application Download PDFInfo
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Abstract
A kind of application the invention discloses benzimidazoles compound and its on organic electroluminescence device, the compound is using benzimidazole and ring is core, has the characteristics that intermolecular be not easy to crystallize, be not easy to assemble, with good filming.The compounds of this invention as OLED luminescent device luminescent layer material of main part in use, device current efficiency, power efficiency and external quantum efficiency are greatly improved；Meanwhile device lifetime is promoted clearly.
Description
Technical field
The present invention relates to technical field of semiconductors, more particularly, to a kind of containing the compound of benzimidazole and its work
For application of the luminescent layer material of main part on Organic Light Emitting Diode.
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 be clipped in Different electrodes film layer it
Between organic functional material, various different function materials are overlapped mutually depending on the application collectively constitutes OLED luminescent device together.
As current device, when the two end electrodes application voltage to OLED luminescent device, and pass through electric field action organic layer functional material
Positive and negative charge in film layer, positive and negative charge is further compound in luminescent layer, i.e. generation OLED electroluminescent.
The organic electroluminescence device of excellent combination property in order to obtain needs to design suitable Subjective and Objective material and optimization
Device architecture, luminescent layer material of main part generally comprise hole and/or electron-transport unit, have suitable carrier transport
Can, and its triplet energy level is required to be higher than illuminator, it just can guarantee that triplet exciton is confined to luminescent layer in this way.In addition, being
Realization carrier is efficiently injected to drop low start voltage, and material of main part should also have relative to the suitable of neighbouring organic layer
Energy level.
In recent years, bipolar host material is led because having the hole of balance and electronic carrier stream in electroluminescent device
Domain is attract attention, and the production that gradually moves towards the industrialization.
For current OLED shows the actual demand of Lighting Industry, the development of OLED material is also far from enough at present, falls
Afterwards in the requirement of panel manufacturing enterprise, the organic functional material as material enterprise development higher performance is particularly important.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, the applicant provide a kind of compound containing benzimidazole and its
Application on organic electroluminescence device.The compounds of this invention is using benzimidazole and ring is core, as luminous layer main body material
Material is applied to Organic Light Emitting Diode, and the device that the present invention makes has good photoelectric properties, can satisfy panel manufacture enterprise
The requirement of industry.
Technical scheme is as follows:
The applicant provides a kind of using benzimidazole and ring is the compound of core, the compound structure such as general formula (1)
It is shown:
In general formula (1), X indicate oxygen atom, sulphur atom or
Ar1、Ar2、Ar3Expression independentlyOr-R；
Wherein, Ar indicates phenyl, C1-10Phenyl, dibiphenylyl, terphenyl or the naphthalene that linear or branched alkyl group replaces
Base；
N takes 1 or 2；
R chooses structure shown in general formula (2) or general formula (3):
Wherein, Ar4Indicate phenyl, C1-10Linear or branched alkyl group replace phenyl, dibiphenylyl, terphenyl, naphthalene,
Anthryl, phenanthryl or benzo phenanthryl；
X1It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Alkylidene, the aryl of linear or branched alkyl group substitution replace
One of the tertiary amine groups that alkylidene, alkyl or aryl replace；
R1、R2、R3Selection hydrogen independently, alkyl, phenyl, the C that carbon atom is 1-101-10Linear or branched alkyl group takes
Structure shown in the phenyl in generation, dibiphenylyl, terphenyl, naphthalene, general formula (4), general formula (5), general formula (6) or general formula (7)；
Wherein, Ar5、Ar6、Ar7Expression phenyl, C independently1-10Phenyl, the biphenyl of linear or branched alkyl group substitution
Base, terphenyl, naphthalene, C1-10Benzofuranyl, the C of linear or branched alkyl group substitution1-10The benzene that linear or branched alkyl group replaces
Bithiophene base, C1-10Fluorenyl, the C of linear or branched alkyl group substitution1-10One of the carbazyl that linear or branched alkyl group replaces；
R4、R5、R6The aromatic radical that the alkyl or carbon atom that selection hydrogen, carbon atom independently is 1-10 are 4-20；
X2It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Alkylidene, the aryl of linear or branched alkyl group substitution replace
One of the tertiary amine groups that alkylidene, alkyl or aryl replace.
Preferably, R in the general formula (1) are as follows:
Any one of.
Preferably, the concrete structure formula of the compound are as follows:
Any one of.
The applicant additionally provides a kind of luminescent device comprising the compound, master of the compound as luminescent layer
Body material, for making OLED device.
The applicant additionally provides a kind of method for preparing the compound, the reaction equation occurred in preparation process
It is:
N in reaction equation, m independently be expressed as 0 or 1；
Wherein, the preparation process of reaction equation 1 is:
Weigh bromo-derivative, the Ar of benzimidazole and ring1H、Ar2H is dissolved with toluene；Add Pd2(dba)3, tri-tert
Phosphine, sodium tert-butoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in 95~110 DEG C of reaction temperature, reaction 10~24
Hour, cooling and filtering reacting solution, filtrate revolving crosses silicagel column, obtains target product；The bromo of the benzimidazole and ring
Object and Ar1H、Ar2The molar ratio of H is 1:0.8~2.0:0.8~2.0, Pd2(dba)3With the molar ratio of bromo-derivative be 0.006~
The molar ratio of 0.02:1, tri-tert-butylphosphine and bromo-derivative is 0.006~0.02:1, and the molar ratio of sodium tert-butoxide and bromo-derivative is
1.0~3.0:1；
The preparation process of reaction equation 2 is:
Weigh benzimidazole benzimidazole and Ar3Br is dissolved with toluene；Add Pd2(dba)3, tri-tert-butylphosphine, tertiary fourth
Sodium alkoxide；Under an inert atmosphere, it by the mixed solution of above-mentioned reactant in 95~110 DEG C of reaction temperature, reacts 10~24 hours, it is cold
But and filtering reacting solution, filtrate revolving cross silicagel column, obtain target product；The benzimidazole benzimidazole and Ar3Br's
Molar ratio is 0.8~2.0:1, Pd2(dba)3With Ar3The molar ratio of Br is 0.006~0.02:1, tri-tert-butylphosphine and Ar3Br's
Molar ratio is 0.006~0.02:1, sodium tert-butoxide and Ar3The molar ratio of Br is 1.0~3.0:1；
The preparation process of reaction equation 3 is:
Weigh bromo-derivative, the Ar of benzimidazole and ring1B(OH)2、Ar2B(OH)2, mixed with the toluene ethyl alcohol that volume ratio is 2:1
Bonding solvent dissolution；Under an inert atmosphere, Na is added2CO3Aqueous solution, Pd (PPh3)4；By the mixed solution of above-mentioned reactant in
It 95~110 DEG C of reaction temperature, reacts 10~24 hours, cooling and filtering reacting solution, filtrate revolving crosses silicagel column, obtains mesh
Mark product；The bromo compound and Ar1B(OH)2、Ar2B(OH)2Molar ratio be 1:1.0~2.0:1.0~2.0；Na2CO3
Molar ratio with bromo-derivative is 1.0~3.0:1；Pd(PPh3)4Molar ratio with bromo-derivative is 0.006~0.02:1.
The present invention is beneficial to be had the technical effect that
The compounds of this invention is using benzimidazole and ring is parent nucleus, reconnects aromatic heterocycle group, destroys molecular symmetry,
To destroy the crystallinity of molecule, intermolecular aggtegation is avoided, the compound structure intramolecular includes electron donor
The mobility of electrons and holes, drop low start voltage can be improved in the combination of (donor, D) and electron acceptor (acceptor, A),
Parent nucleus benzimidazole and ring triplet energy level with higher, are confined to compound triplet exciton in luminescent layer, improve hair
Light efficiency, the compounds of this invention are suitable as the use of luminescent layer material of main part.
Compound of the present invention can be used as emitting layer material and make applied to OLED luminescent device, as luminous layer main body
Material can obtain good device performance, and the current efficiency of device, power efficiency and external quantum efficiency are greatly improved；
Meanwhile device lifetime is promoted clearly.
Compound-material of the present invention has good application effect in OLED luminescent device, has good industry
Change prospect.
Detailed description of the invention
Fig. 1 is the device architecture schematic diagram using the compounds of this invention；
Wherein, 1 is transparent substrate layer, and 2 be ito anode layer, and 3 be hole injection layer, and 4 be hole transmission layer, and 5 be luminous
Layer, 6 be electron transfer layer, and 7 be electron injecting layer, and 8 be cathode reflection electrode layer.
Specific embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
Embodiment 1: the synthesis of compound 3
The specific synthetic route of the compound is now provided:
0.01mol2,9- bis- bromo- benzo [d] benzo [4,5] is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 500ml
Imidazoles [2,1-b] oxazole, 0.015mol 10- (4- phenyl boric acid) -10H- phenoxazine, with mixed solvent dissolution (180ml toluene,
90ml ethyl alcohol), 0.03molNa is then added2CO30.0001mol Pd (PPh is then added in aqueous solution (2M)3)4, it is heated to reflux
10-24 hours, sample contact plate, fully reacting.Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, HPLC
Purity 95.9%, yield 59.00%.
HPLC-MS: material molecule amount 722.23 surveys molecular weight 722.59.
Embodiment 2: the synthesis of compound 10
The specific synthetic route of the compound is now provided:
0.01mol3, bis- bromo- 5 (2,4 diphenyl -6- of 9- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
[1,1'；3', 1 "] triphenyl)-benzimidazole [1,2-a] benzimidazole, 0.015mol phenoxazine, 0.03mol sodium tert-butoxide, 1
×10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene are heated to reflux 24 hours, sample contact plate, reaction
Completely, natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 95.81%, yield 75.20%.
HPLC-MS: material molecule amount 797.28 surveys molecular weight 797.38.
Embodiment 3: the synthesis of compound 20
The specific synthetic route of the compound is now provided:
0.01mol10- [the bromo- 5- of 3- (9- methyl -9H- a word used for translation is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Pyridine -10- base)-phenyl] -9,9- dimethyl -9,10- dihydro-acridine, 0.015mol 5H- benzimidazole [1,2-a] benzo miaow
Azoles, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene, is heated to reflux
24 hours, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity
99.24 yield 64.00%.
HPLC-MS: material molecule amount 679.32 surveys molecular weight 679.46.
Embodiment 4: the synthesis of compound 24
The specific synthetic route of the compound is now provided:
The preparation method of compound 24 is with embodiment 3, the difference is that raw material 5- (the bromo- biphenyl -3- base of 3'-) -10- benzene
Base -5,10- dihydro-azophenlyene replaces 10- [the bromo- 5- of 3- (9- methyl -9H- acridine -10- base)-phenyl] -9,9- dimethyl -9,10-
Dihydro-acridine.
HPLC-MS: material molecule amount 615.24 surveys molecular weight 615.29.
Embodiment 5: the synthesis of compound 34
The specific synthetic route of the compound is now provided:
0.01mol 9- bromine 5- Phenyl-benzoimidazol [1,2- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
A] benzimidazole, 0.015mol 3- methyl -7- naphthalene -1- base -10H- azophenlyene, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2
(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene are heated to reflux 24 hours, sample contact plate, and fully reacting is naturally cold
But, it filters, filtrate revolving crosses silicagel column, obtains target product, purity 99.69, yield 59.60%.
HPLC-MS: material molecule amount 604.23 surveys molecular weight 604.36.
Embodiment 6: the synthesis of compound 46
The specific synthetic route of the compound is now provided:
The bromo- benzo of 0.01mol9- [d] benzo [4,5] imidazoles is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 500ml
[2,1-b] oxazole, 0.015mol 3- (3- (hexichol amido) -10H- phenoxazine -10- base) phenyl boric acid, is dissolved with mixed solvent
(180ml toluene, 90ml ethyl alcohol), is then added 0.03molNa2CO30.0001mol Pd is then added in aqueous solution (2M)
(PPh3)4, it is heated to reflux 10-24 hours, samples contact plate, fully reacting.Natural cooling, filtering, filtrate revolving are crossed silicagel column, are obtained
To target product, HPLC purity 99.4%, yield 53.00%.
HPLC-MS: material molecule amount 632.22 surveys molecular weight 632.35.
Embodiment 7: the synthesis of compound 54
The specific synthetic route of the compound is now provided:
The bromo- benzo of 0.01mol 2- [d] benzo [4,5] miaow is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Azoles [2,1-b] thiazole, (the dibenzofurans) -4- of 0.015mol bis- base-(10H- phenoxazine -3- base)-amine, the 0.03mol tert-butyl alcohol
Sodium, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert-butylphosphine, 150ml toluene is heated to reflux 24 hours, sample point
Plate, fully reacting, natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 98.32, yield
56.00%.
HPLC-MS: material molecule amount 768.22 surveys molecular weight 768.22.
Embodiment 8: the synthesis of compound 61
The specific synthetic route of the compound is now provided:
0.01mo, 2,9- bis- bromo- benzo [d] benzos [4,5] are added under the atmosphere for being passed through nitrogen in the four-hole bottle of 500ml
Imidazoles [2,1-b] oxazole, 0.010mol 9,9- dimethyl -7- (naphthalene -2- base (phenyl) amido) -10- phenyl -9,10- dihydro a word used for translation
Pyridine -2- ylboronic acid, 0.01mol phenyl boric acid dissolve (180ml toluene, 90ml ethyl alcohol) with mixed solvent, are then added
0.03molNa2CO30.0001mol Pd (PPh is then added in aqueous solution (2M)3)4, 10-24 hours are heated to reflux, sample point
Plate, fully reacting.Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, HPLC purity 95.56%, yield
35.00%.
HPLC-MS: material molecule amount 784.32 surveys molecular weight 784.39.
Embodiment 9: the synthesis of compound 72
The specific synthetic route of the compound is now provided:
The preparation method of compound 72 with embodiment 7, the difference is that raw material 2- carbazole -9- base -10- phenyl -8- [1,
1'；3', 1 "] triphenyl -5'- base -5,10- dihydro-azophenlyene replacement two (dibenzofurans) -4- bases-(10H- phenoxazine -3-
Base)-amine, the bromo- benzo of raw material 3- [d] benzo [4,5] imidazoles [2,1-b] the thiazole replacement bromo- benzo of 2- [d] benzo [4,5] imidazoles
[2,1-b] thiazole.
HPLC-MS: material molecule amount 873.29 surveys molecular weight 874.56.
Embodiment 10: the synthesis of compound 86
The specific synthetic route of the compound is now provided:
0.01mol 2- dibenzo [d] benzo [4,5] imidazoles is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 500ml
[2,1-b] oxazole, 0.015mol 10- phenyl -7- (9- phenyl -9H- carbazole -3- base) -10H- phenoxazine -3- ylboronic acid, use
Mixed solvent dissolves (180ml toluene, 90ml ethyl alcohol), and 0.03molNa is then added2CO3Aqueous solution (2M), is then added
0.0001mol Pd(PPh3)4, it is heated to reflux 10-24 hours, samples contact plate, fully reacting.Natural cooling, filtering, filtrate rotation
It steams, crosses silicagel column, obtain target product, HPLC purity 97.60%, yield 38.00%.
HPLC-MS: material molecule amount 706.24 surveys molecular weight 706.35.
Embodiment 11: the synthesis of compound 95
The specific synthetic route of the compound is now provided:
0.01mo 9- bromine 5- Phenyl-benzoimidazol [1,2- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 500ml
A] benzimidazole, 0.015mol 10- phenyl -10H-3,10'- join phenoxazine -7- ylboronic acid, dissolve (180ml with mixed solvent
Toluene, 90ml ethyl alcohol), 0.03mol Na is then added2CO30.0001mol Pd (PPh is then added in aqueous solution (2M)3)4, add
Heat reflux 10-24 hours, samples contact plate, fully reacting.Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target production
Object, HPLC purity 99.90%, yield 28.00%.
HPLC-MS: material molecule amount 721.25 surveys molecular weight 721.55.
The compounds of this invention can be used as the use of luminescent layer material of main part, to the compounds of this invention 10, compound 86 and show
There is material C BP to carry out the measurement of electron mobility, hole mobility, T1 energy level and electrochemical stability, testing result respectively
As shown in table 1.
Table 1
| Compound | Electron mobility (cm2V-1s-1) | Hole mobility (cm2V-1s-1) | Electrochemical stability | T1 energy level (eV) |
| Compound 10 | 5×10-4 | 6×10-3 | It is excellent | 3.3 |
| Compound 86 | 8×10-4 | 3×10-3 | It is excellent | 2.9 |
| Material C BP | 3×10-4 | 2×10-3 | Difference | 2.7 |
Note: electron mobility and hole mobility are measured by space charge limited current method；It is electrochemically stable
Property be that the redox characteristic for observing material by cyclic voltammetry is identified；Test condition: test sample is dissolved in volume
Than the methylene chloride and acetonitrile mixed solvent for 2:1, concentration 1mg/mL, electrolyte is the tetrabutyl ammonium tetrafluoroborate or six of 0.1M
The organic solution of fluorophosphoric acid tetrabutylammonium.Reference electrode is Ag/Ag+ electrode, is titanium plate to electrode, and working electrode is ITO electrode,
Cycle-index is 20 times.T1 is the phosphorescence emission spectra for first testing compound, and is calculated by phosphorescent emissions peak that (test is set
It is standby: to utilize the FLS980 Fluorescence Spectrometer of Edinburgh Instruments, the Optistat of Oxford Instruments
DN-V2 cryogenic assembly).
By upper table data it is found that the compounds of this invention have preferable oxidation-reduction stability, higher thermal stability, compared with
High T1 energy level, is suitable as the material of main part of luminescent layer；Meanwhile the compounds of this invention contain electron donor (donor, D) with
Electron acceptor (acceptor, A) makes so that the OLED device electrons and holes using the compounds of this invention reach equilibrium state
It obtains device efficiency and the service life gets a promotion.
12-22 and comparative example 1~3 the compound conduct in the devices that the present invention will be described in detail synthesizes by the following examples
The application effect of luminescent layer material of main part.Embodiment 13-22 is compared with embodiment 12, the complete phase of the manufacture craft of the device
Together, and identical baseplate material and electrode material are used, the film thickness of electrode material is also consistent, except that device
Emitting layer material is changed in part.Embodiment 12-22 is compared with comparative example 1~3, the luminescent layer of device described in comparative example 1
Material is using existing common raw material, and the device emitting layer material of embodiment 12-22 is using the compounds of this invention.Respectively
The structure composition of embodiment obtained device is as shown in table 2.The performance test results of each device are as shown in table 3.
Embodiment 12
2/ hole injection layer of transparent substrate layer 1/ITO anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4
(the weight ratio blending of compound 3 and GD-19 according to 100:5, thickness the 30nm)/electronics of (TAPC, thickness 80nm)/luminescent layer 5 passes
Defeated 6 (TPBI, thickness 40nm)/electron injecting layer of layer, 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).Associated materials
Molecular structural formula is as follows:
Specific preparation process is as follows:
Transparent substrate layer 1 uses transparent material.Ito anode layer 2 (film thickness 150nm) is washed, i.e., is successively carried out
Ultraviolet-ozone washing is carried out after neutralizing treatment, pure water, drying again to remove the organic residue on the transparent surface ITO.
On having carried out the ito anode layer 2 after above-mentioned washing, using vacuum deposition apparatus, it is 10nm's that film thickness, which is deposited,
Molybdenum trioxide MoO3It is used as hole injection layer 3.And then the TAPC of 80nm thickness is deposited as hole transmission layer 4.
After above-mentioned hole mobile material vapor deposition, the luminescent layer 5 of OLED luminescent device is made, structure includes OLED hair
The used material compound 3 of photosphere 5 is used as material of main part, and for GD-19 as dopant material, dopant material doping ratio is 5% weight
Ratio is measured, luminescent layer film thickness is 30nm.
After above-mentioned luminescent layer 5, continuation vacuum evaporation electron transport layer materials are TPBI.The vacuum evaporation coating of the material
Thickness is 40nm, this layer is electron transfer layer 6.
On electron transfer layer 6, by vacuum deposition apparatus, lithium fluoride (LiF) layer that film thickness is 1nm is made, this layer is
Electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, aluminium (Al) layer that film thickness is 80nm is made, this layer is cathode
Reflection electrode layer 8 uses.
After completing OLED luminescent device as described above, anode and cathode is connected with well known driving circuit, is surveyed
The I-E characteristic of the luminous efficiency of metering device, luminescent spectrum and device.
Embodiment 13
2/ hole injection layer of transparent substrate layer 1/ITO anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4
(the weight ratio blending of compound 10 and GD-19 according to 100:5, thickness the 30nm)/electronics of (TAPC, thickness 80nm)/luminescent layer 5 passes
Defeated 6 (TPBI, thickness 40nm)/electron injecting layer of layer, 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 14
2/ hole injection layer of transparent substrate layer 1/ITO anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4
(the weight ratio blending of compound 20 and GD-19 according to 100:5, thickness the 30nm)/electronics of (TAPC, thickness 80nm)/luminescent layer 5 passes
Defeated 6 (TPBI, thickness 40nm)/electron injecting layer of layer, 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 15
2/ hole injection layer of transparent substrate layer 1/ITO anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4
(the weight ratio blending of compound 24 and GD-19 according to 100:5, thickness the 30nm)/electronics of (TAPC, thickness 80nm)/luminescent layer 5 passes
Defeated 6 (TPBI, thickness 40nm)/electron injecting layer of layer, 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 16
2/ hole injection layer of transparent substrate layer 1/ITO anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4
(the weight ratio blending of compound 34 and GD-19 according to 100:5, thickness the 30nm)/electronics of (TAPC, thickness 80nm)/luminescent layer 5 passes
Defeated 6 (TPBI, thickness 40nm)/electron injecting layer of layer, 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 17
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 46 and Ir (PPy) 3 according to 100:10, thickness 30nm)/electricity
Sub- 6 (TPBI, thickness 40nm)/electron injecting layer of transport layer, 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 18
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 54 and Ir (PPy) 3 according to 100:10, thickness 30nm)/electricity
Sub- 6 (TPBI, thickness 40nm)/electron injecting layer of transport layer, 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 19
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 61 and GD-PACTZ according to 100:5, thickness 30nm)/electricity
Sub- 6 (TPBI, thickness 40nm)/electron injecting layer of transport layer, 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 20
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 72 and GD-PACTZ according to 100:5, thickness 30nm)/electricity
Sub- 6 (TPBI, thickness 40nm)/electron injecting layer of transport layer, 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 21
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 86, GH-204 and Ir (PPy) 3 according to 70:30:10, thickness
Spend 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8
(Al)。
Embodiment 22
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 95, GH-204 and GD-PACTZ according to 70:30:5, thickness
30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8
(Al)。
Comparative example 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 CBP and GD-19 according to 100:5, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Comparative example 2
2/ hole injection layer of transparent substrate layer 1/ITO anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4
(the weight ratio blending of CBP and Ir (PPy) 3 according to 100:10, thickness the 30nm)/electronics of (TAPC, thickness 80nm)/luminescent layer 5 passes
Defeated 6 (TPBI, thickness 40nm)/electron injecting layer of layer, 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Comparative example 3
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 CBP and GD-PACTZ according to 100:5, thickness 30nm)/electron-transport
Layer 6 (TPBI, thickness 40nm)/electron injecting layer, 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Table 2
Table 3
| Device code name | Current efficiency | Color | The LT95 service life |
| Embodiment 12 | 10.68 | Green light | 6.00 |
| Embodiment 13 | 13.26 | Green light | 12.50 |
| Embodiment 14 | 11.05 | Green light | 8.50 |
| Embodiment 15 | 11.68 | Green light | 13.0 |
| Embodiment 16 | 8.94 | Green light | 5.5 |
| Embodiment 17 | 25.69 | Green light | 10.50 |
| Embodiment 18 | 26.82 | Green light | 6.50 |
| Embodiment 19 | 29.38 | Green light | 9.50 |
| Embodiment 20 | 26.43 | Green light | 12.00 |
| Embodiment 21 | 32.76 | Green light | 16.00 |
| Embodiment 22 | 31.26 | Green light | 14.50 |
| Comparative example 1 | 6.50 | Green light | 3.80 |
| Comparative example 2 | 24.60 | Green light | 4.30 |
| Comparative example 3 | 25.10 | Green light | 7.80 |
Illustrate: the current efficiency of comparative example 1 is 6.5cd/A (@10mA/cm2)；Starting voltage is 4.3V (@1cd/m2),
LT95 life time decay is 3.8Hr under 5000nit brightness.The current efficiency of comparative example 2 is 24.6cd/A (@10mA/cm2)；5000
LT95 life time decay is 4.3Hr under brightness.The current efficiency of comparative example 3 is 25.1cd/A (@10mA/cm2)；Starting voltage is
LT95 life time decay is 7.8Hr under 3.5V (@1cd/m2) 5000nit brightness.Life-span test system be owner of the present invention and
The OLED device life-span tester that Shanghai University is studied jointly.
The starting voltage of embodiment 13 is 3.7V (@1cd/m2), the starting voltage of embodiment 21 is 2.9V (@1cd/m2)。
From the results shown in Table 3, compound of the present invention can be applied to OLED hair as luminescent layer material of main part
Optical device production；And compared with comparative example 1, either efficiency, starting voltage or service life are obtained than known OLED material
The driving service life of larger change, especially device obtains biggish promotion.
From the point of view of above data application, the compounds of this invention has in OLED luminescent device good as emitting layer material
Application effect, have good industrialization prospect.
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 (6)
1. a kind of using benzimidazole and ring is the compound of core, it is characterised in that shown in the compound structure such as general formula (1):
In general formula (1), X indicate oxygen atom, sulphur atom or
Ar1、Ar2、Ar3Expression independentlyOr-R；
Wherein, Ar indicates phenyl, C1-10Phenyl, dibiphenylyl, terphenyl or the naphthalene that linear or branched alkyl group replaces；
N takes 1 or 2；
R chooses structure shown in general formula (2) or general formula (3):
Wherein, Ar4Indicate phenyl, C1-10Linear or branched alkyl group replace phenyl, dibiphenylyl, terphenyl, naphthalene, anthryl,
Phenanthryl or benzo phenanthryl；
X1It is expressed as oxygen atom；Sulphur atom；Selenium atom；The methylene that dimethyl or diphenyl replace；What methyl or tert-butyl replaced
Tertiary amine groups；Or one of the tertiary amine groups that phenyl replaces；Or X1Connect as spiral shell carbon atom with fluorenyl；
R1、R2、R3Selection hydrogen independently, alkyl, phenyl, the C that carbon atom is 1-101-10The benzene that linear or branched alkyl group replaces
Structure shown in base, dibiphenylyl, terphenyl, naphthalene, general formula (4), general formula (5), general formula (6) or general formula (7)；
Wherein, Ar5、Ar6、Ar7Expression phenyl, C independently1-10Phenyl, the dibiphenylyl, three of linear or branched alkyl group substitution
Xenyl, naphthalene, C1-10Benzofuranyl, the C of linear or branched alkyl group substitution1-10The benzo thiophene that linear or branched alkyl group replaces
Pheno base, C1-10Fluorenyl, the C of linear or branched alkyl group substitution1-10One of the carbazyl that linear or branched alkyl group replaces；
R4、R5、R6The aromatic radical that the alkyl or carbon atom that selection hydrogen, carbon atom independently is 1-10 are 4-20；
X2It is expressed as oxygen atom；Sulphur atom；Selenium atom；Methyl substituted methylene；Or one of the tertiary amine groups that phenyl replaces.
2. compound according to claim 1, it is characterised in that R in the general formula (1) are as follows:
Any one of.
3. compound according to claim 1, it is characterised in that the concrete structure formula of the compound are as follows:
Any one of.
4. a kind of using benzimidazole and ring is the compound of core, it is characterised in that the concrete structure formula of the compound are as follows:
Any one of.
5. a kind of luminescent device comprising any one of Claims 1 to 4 compound, it is characterised in that the compound conduct
The material of main part of luminescent layer, for making OLED device.
6. a kind of method for preparing any one of Claims 1 to 4 compound, it is characterised in that is occurred in preparation process is anti-
Answering equation is:
N in reaction equation, m independently be expressed as 0 or 1；
Wherein, the preparation process of reaction equation 1 is:
Weigh bromo-derivative, the Ar of benzimidazole and ring1H、Ar2H is dissolved with toluene；Add Pd2(dba)3, tri-tert-butylphosphine, uncle
Sodium butoxide；Under an inert atmosphere, it by the mixed solution of above-mentioned reactant in 95~110 DEG C of reaction temperature, reacts 10~24 hours,
Cooling and filtering reacting solution, filtrate revolving, crosses silicagel column, obtains target product；The bromo-derivative of the benzimidazole and ring with
Ar1H、Ar2The molar ratio of H is 1:0.8~2.0:0.8~2.0, Pd2(dba)3Molar ratio with bromo-derivative is 0.006~0.02:
1, the molar ratio of tri-tert-butylphosphine and bromo-derivative is 0.006~0.02:1, the molar ratio of sodium tert-butoxide and bromo-derivative is 1.0~
3.0:1；
The preparation process of reaction equation 2 is:
Weigh benzimidazole benzimidazole and Ar3Br is dissolved with toluene；Add Pd2(dba)3, tri-tert-butylphosphine, the tert-butyl alcohol
Sodium；Under an inert atmosphere, it by the mixed solution of above-mentioned reactant in 95~110 DEG C of reaction temperature, reacts 10~24 hours, it is cooling
And filtering reacting solution, filtrate revolving cross silicagel column, obtain target product；The benzimidazole benzimidazole and Ar3Br's rubs
You are than being 0.8~2.0:1, Pd2(dba)3With Ar3The molar ratio of Br is 0.006~0.02:1, tri-tert-butylphosphine and Ar3Br's rubs
You are than being 0.006~0.02:1, sodium tert-butoxide and Ar3The molar ratio of Br is 1.0~3.0:1；
The preparation process of reaction equation 3 is:
Weigh bromo-derivative, the Ar of benzimidazole and ring1B(OH)2、Ar2B(OH)2, mixed with the toluene ethyl alcohol that volume ratio is 2:1 molten
Agent dissolution；Under an inert atmosphere, Na is added2CO3Aqueous solution, Pd (PPh3)4；By the mixed solution of above-mentioned reactant in reaction
It 95~110 DEG C of temperature, reacts 10~24 hours, cooling and filtering reacting solution, filtrate revolving crosses silicagel column, obtains target production
Object；The bromo compound and Ar1B(OH)2、Ar2B(OH)2Molar ratio be 1:1.0~2.0:1.0~2.0；Na2CO3With bromine
Molar ratio for object is 1.0~3.0:1；Pd(PPh3)4Molar ratio with bromo-derivative is 0.006~0.02:1.
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Non-Patent Citations (1)
| Title |
|---|
| Benzimidazobenzothiazole-Based Bipolar Hosts to Harvest Nearly All of the Excitons from Blue Delayed Fluorescence and Phosphorescent Organic Light-Emitting Diodes;Lin-Song Cui等;《Angew. Chem.》;20160421;第128卷;第6978-6982页 |
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