CN109796473A - It is a kind of using pyridine diindyl as the compound of core and its application - Google Patents
It is a kind of using pyridine diindyl as the compound of core and its application Download PDFInfo
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Abstract
The present invention relates to a kind of organic compound such as general formula (1) and its applications.The compounds of this invention glass transition temperature with higher and molecule thermal stability, suitable HOMO and lumo energy, higher Eg are optimized by device architecture, can effectively promote the photoelectric properties of OLED device and the service life of OLED device.General formula (1).
Description
Technical field
The present invention relates to technical field of semiconductors more particularly to it is a kind of using pyridine diindyl as the compound of core and its
Application on organic electroluminescence device.
Background technique
Organic electroluminescent (OLED:OrganicLightEmissionDiodes) device technology can both be used to manufacture new
Type shows product, can be used for production novel illumination product, is expected to substitute existing liquid crystal display and fluorescent lighting, applies
Prospect is very extensive.
OLED luminescent device including electrode material film layer and is clipped between Different electrodes film layer like the structure of sandwich
Organic functional material, various different function materials are overlapped mutually depending on the application collectively constitutes OLED luminescent device together.
OLED luminescent device is as current device, when applying voltage to its two end electrodes, and passes through electric field action organic layer functional material
When positive and negative charge in film layer, positive and negative charge is further compound in luminescent layer, i.e. generation OLED electroluminescent.
Currently, OLED display technology in smart phone, applied by the fields such as tablet computer, further will also be to electricity
Depending on etc. large scales application field extension, still with actual products application require compare, the luminous efficiency and use of OLED device
The performances such as service life also need further to be promoted.
Proposing high performance research to OLED luminescent device at present includes: the driving voltage for reducing device, the hair for improving device
Light efficiency, the service life for improving device etc..In order to realize OLED device performance continuous promotion, not only need from OLED device
The innovation of part structure and manufacture craft is constantly studied and is innovated with greater need for oled light sulfate ferroelectric functional material, formulates out higher performance
OLED functional material.
Oled light sulfate ferroelectric functional material applied to OLED device can be divided into two major classes from purposes, and respectively charge injects
Transmission material and luminescent material.Further, it can also inject charge into transmission material and be divided into electron injection transmission material, electronic blocking
Luminescent material, can also be divided into main body luminescent material and doping material by material, hole injection transmission material and hole barrier materials
Material.
In order to make high performance OLED luminescent device, it is desirable that various organic functional materials have good photoelectric properties,
For example, as charge transport materials, it is desirable that have good carrier mobility, high-vitrification conversion temperature etc., as luminous
The material of main part of layer has good bipolarity, HOMO/LUMO energy rank appropriate etc..
The oled light sulfate ferroelectric functional material film layer for constituting OLED device includes at least two layers or more structure, applies in industry
OLED device structure then includes hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron-transport
A variety of film layers such as layer, electron injecting layer, that is to say, that the photoelectric functional material applied to OLED device is injected including at least hole
Material, hole mobile material, luminescent material, electron transport material etc., material type and collocation form have rich and various
The characteristics of property.In addition, used photoelectric functional material has stronger choosing for the collocation of the OLED device of different structure
Selecting property, performance of the identical material in different structure device may also be completely totally different.
Therefore, for the industry application requirement of current OLED device and the different function film layer of OLED device, device
Photoelectric characteristic demand, it is necessary to which selection is more suitable for, the higher OLED functional material of performance or combination of materials, is just able to achieve the height of device
Efficiency, the overall characteristic of long-life and low-voltage.For current OLED shows the actual demand of Lighting Industry, OLED at present
The development of material is also far from enough, lags behind the requirement of panel manufacturing enterprise, as the organic of material enterprise development higher performance
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 pyridine diindyl as the chemical combination of core
Object and its application on organic electroluminescence device.The compounds of this invention contains pyrido indole structure, glass with higher
Glass temperature and molecule thermal stability, suitable HOMO and lumo energy, higher Eg are optimized by device architecture, can effectively be mentioned
Rise the photoelectric properties of OLED device and the service life of OLED device.
The technical scheme to solve the above technical problems is that
It is a kind of using pyridine diindyl as the compound of core, shown in the compound structure such as general formula (1):
General formula (1)
Ar is expressed as the C for being substituted or being unsubstituted in general formula (1)6To C30Aryl, the C for being substituted or being unsubstituted5Extremely
C30One of heteroaryl；
In general formula (1), X1, X2, X3, X4Independently be expressed as C-H or N, and at least one is expressed as N atom；
In general formula (1), R is expressed as structure shown in general formula (2)；
General formula (2)
In general formula (2), L is represented by singly-bound, substituted or unsubstituted C6-60 arlydene, substituted or unsubstituted 5~60
First heteroarylidene, the hetero atom in the heteroarylidene are nitrogen, oxygen or sulphur；
In general formula (2), X5Alkylidene, aryl that oxygen, sulphur, selenium, C1-10 linear or branched alkyl group replace is expressed as to replace
One of the imido grpup that alkylidene, alkyl-substituted imido grpup or aryl replace；
In general formula (2), R1、R2Independently be expressed as hydrogen atom, general formula (3), general formula (4), general formula (5) or general formula (6)
Middle structure；
In general formula (3) and general formula (4), X6、X7、X8Independently be expressed as oxygen, sulphur, C1-10Linear or branched alkyl group takes
One of the imido grpup that alkylidene, alkyl-substituted imido grpup or the aryl that alkylidene, the aryl in generation replace replace；
General formula (3), general formula (4), general formula (5) pass through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL4-CL5Key, CL’1-CL’2
Key, CL'2-CL’3Key CL’3-CL’4Key or CL’4-CL’5It is connected with general formula (2) and ring；
In general formula (6), R3、R4Independently be expressed as phenyl, naphthalene, dibiphenylyl, terphenyl, carbazyl, furans
In base, pyridyl group, phenanthryl, anthryl, dibenzofuran group, dibenzothiophene, 9,9- dimethyl fluorenyl or N- phenyl carbazole base
One kind, R3 and R4 are same or different.
Further, shown in the compound structure such as formula (I)~(IV):
The i.e. described X1, X2, X3And X4In only one be expressed as N.
Further, general formula (2) structure such as (1)~(12) are shown:
Further, described Ar, R3And R4Expression independently are as follows: Any one of.
Further, the L is indicated are as follows: singly-bound, Any one of.
The present invention also provides a kind of preparation methods of compound as described above, prepare the reaction equation of the compound
Are as follows:
(1) when L is singly-bound, the raw material N containing pyrido indolyl radical is connected with the R group of raw material M with C-N key,
Prepare the reaction equation of the compound are as follows:
The preparation method comprises the following steps: raw material N and raw material M are dissolved in dry toluene, sodium tert-butoxide and Pd are added after deoxygenation
(dppf)Cl2, 95~110 DEG C of 10~24 hours of reaction under an inert atmosphere monitor reaction process with TLC in reaction process,
After raw material fully reacting, filtrate is rotated and removes solvent by cooling, filtering, and crude product crosses silicagel column, target compound；
Wherein, the molar ratio of the raw material N and raw material M is 1:(1.1~2.5), Pd (dppf) Cl2With mole of raw material N
Than for (0.006~0.02): 1, the molar ratio of sodium tert-butoxide and raw material N are (1.5~2): 1；
(2) when L is not singly-bound, pyridine diindyl is connected with R with C-C key,
Specifically the preparation method comprises the following steps: using raw material N and intermediate B as raw material, Pd (PPh is added in toluene dissolution after deoxygenation3)4And carbon
Sour sodium by above-mentioned mixed solution in 95~110 DEG C, reacts 10~24 hours, cooled to room temperature under nitrogen protection, and
Filtering reacting solution, filtrate carry out vacuum rotary steam, cross neutral silica gel column, obtain target compound；
Wherein, toluene dosage is that every gram of raw material N uses 30-50ml toluene, and the molar ratio of raw material N and intermediate B is 1:
(1.0~1.5)；Pd(PPh3)4Molar ratio with raw material N is (0.005~0.01): 1, the molar ratio of the sodium carbonate and raw material N
For (1.5~3.0): 1.
The present invention also provides a kind of compounds as described above to be used to prepare organic electroluminescence device.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device includes at least one layer of function
Layer contains the compound of above-mentioned pyridine diindyl.
Based on the above technical solution, the present invention can also be improved as follows.
Further, the organic electroluminescence device includes hole transmission layer/electronic barrier layer, and the hole transmission layer/
Electronic barrier layer contains the compound of above-mentioned pyridine diindyl.
Further, the organic electroluminescence device includes luminescent layer, and the luminescent layer contains above-mentioned pyridine diindyl
Compound.
The present invention also provides a kind of illumination or display elements, including organic electroluminescence device as described above.
The present invention is beneficial to be had the technical effect that
For the compounds of this invention using pyridine diindyl as parent nucleus, connected symmetrical dendrimer or asymmetrical rigid radical destroy molecule
Crystallinity avoids intermolecular aggtegation, has high glass transition temperature, material is in OLED device in application, can keep high
Membranous layer stability, improve OLED device service life.
The compounds of this invention structure balances electrons and holes more in the distribution of luminescent layer, in appropriate HOMO energy level
Under, improve hole injection/transmission performance；Under suitable lumo energy, and play the role of electronic blocking, promotes exciton
Combined efficiency in luminescent layer；When light emitting functional layer materials'use as OLED luminescent device, the collocation of pyridine diindyl this
Branch in invention scope can effectively improve exciton utilization rate and high fluorescent radiation efficiency, reduce the efficiency rolling under high current density
Drop reduces device voltage, improves current efficiency and the service life of device.
Compound of the present invention has good application effect in OLED luminescent device, before having good industrialization
Scape.
Detailed description of the invention
Fig. 1 is the structural schematic diagram that material cited by the present invention is applied to OLED device；
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 hinder for electronics
Barrier, 6 be luminescent layer, and 7 be hole blocking layer/electron transfer layer, and 8 be electron injecting layer, and 9 be cathode reflection electrode layer.
Fig. 2 is the efficiency curve diagram that device measures at different temperatures.
Specific embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
The meaning of the symbols such as L, R used below is identical with claim.
When L is not expressed as singly-bound,
Intermediate B, boronic acid compoundsSynthesis:
Under nitrogen atmosphere, weigh intermediate A (structural formula R-Cl) and be dissolved in tetrahydrofuran (THF), then will be bis- (frequency which
Alcohol foundation) two boron, (1,1 '-bis- (diphenylphosphine) ferrocene) dichloro palladium (II) and potassium acetate addition, mixture is stirred, it will be upper
The mixed solution for stating reactant is heated to reflux 5-10 hours at 70-90 DEG C of reaction temperature；After reaction, add water cooling and incite somebody to action
Mixture filtering is simultaneously dry in vacuum drying oven.Residue obtained is crossed into silica gel column separating purification, obtains intermediate B
By taking the synthesis of intermediate B 1 as an example:
(1) in the there-necked flask of 250ml, lead under nitrogen protection, 0.02mol raw material M1,0.024mol para chlorobromobenzene be added,
0.04mol sodium tert-butoxide, 1 × 10-4molPd2(dba)3, 1 × 10-4It is small to be heated to reflux 24 for mol tri-tert phosphorus, 150ml toluene
When, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain intermediate A 1, HPLC purity
97.4%, yield 75.5%；HRMS (EI): calculated value 409.1223, measured value 409.1254.
(2) in 250mL there-necked flask, it is passed through nitrogen, 0.02mol intermediate A 1 is added and is dissolved in 150ml tetrahydrofuran,
Again by 0.024mol bis- (pinacol foundation) two boron, 0.0002mol (1,1 '-bis- (diphenylphosphine) ferrocene) dichloro palladium (II) with
And 0.05mol potassium acetate is added, stirring mixture heats back by the mixed solution of above-mentioned reactant at 80 DEG C of reaction temperature
Stream 5 hours；After reaction, it cools down and is added 100ml water and mixture is filtered and is dried in vacuum drying oven.It will be obtained
The residue obtained crosses silica gel column separating purification, obtains intermediate B 1；HPLC purity 96.5%, yield 92.1%.HRMS (EI): meter
Calculation value is 501.2475, measured value 501.2499.
Intermediate B is prepared with the synthetic method of raw material M, specific structure is as shown in table 1.
Embodiment 1: the synthesis of compound 3:
In the there-necked flask of 250ml, lead under nitrogen protection, 0.02mol raw material N1,0.024mol raw material M1 be added,
0.04mol sodium tert-butoxide, 1 × 10-4molPd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 150ml toluene is heated to reflux 24
Hour, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain compound 3, HPLC purity
98.4%, yield 80.5%；HRMS (EI): calculated value 541.2154, measured value 541.2133.
Embodiment 2: the synthesis of compound 12:
The preparation method is the same as that of Example 1 for compound 12, the difference is that replacing raw material N1 with raw material N2, is replaced with raw material M2
For M1.HPLC purity 97.4%, yield 79.5%；HRMS (EI): calculated value 541.2154, measured value 541.2115.
Embodiment 3: the synthesis of compound 66:
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol raw material N2,0.012mol intermediate B 1 be added,
150ml toluene is stirred, then addition 0.02mol sodium carbonate, and 1 × 10-4molPd(PPh3)4, 105 DEG C are heated to, reflux is anti-
It answers 24 hours, samples contact plate, display is without bromo-derivative residue, fully reacting；Cooled to room temperature, filtering, filtrate are depressurized
It rotates (- 0.09MPa, 85 DEG C), crosses neutral silica gel column, obtain target product, HPLC purity 99.1%, yield 75%.HRMS
(EI): calculated value 617.2467, measured value 617.2455.
Embodiment 4: the synthesis of compound 83:
The preparation method of compound 83 is with embodiment 3, the difference is that raw material N2 is replaced with raw material N1, with intermediate B 2
Substitute B1.HPLC purity 96.4%, yield 74.5%；HRMS (EI): calculated value 617.2467, measured value 617.2417.
Embodiment 5: the synthesis of compound 99:
The preparation method of compound 99 is with embodiment 3, the difference is that raw material N2 is replaced with raw material N3, with intermediate B 3
Substitute B1.HPLC purity 99.4%, yield 68.0%；HRMS (EI): calculated value 617.2467, measured value 617.2456.
Embodiment 6: the synthesis of compound 105:
The preparation method of compound 105, the difference is that replacing raw material N2 with raw material N4, uses intermediate with embodiment 3
B4 substitutes B1.HPLC purity 98.4%, yield 78.0%；HRMS (EI): calculated value 617.2420, measured value 617.2437.
Embodiment 7: the synthesis of compound 113:
The preparation method is the same as that of Example 1 for compound 113, the difference is that raw material N1 is replaced with raw material N5, with raw material M2
Substitute M1.HPLC purity 99.4%, yield 68.0%；HRMS (EI): calculated value 631.2260, measured value 631.2278.
Embodiment 8: the synthesis of compound 119:
The preparation method of compound 119, the difference is that replacing raw material N1 with raw material N6, uses intermediate with embodiment 3
B5 substitutes B1.HPLC purity 99.4%, yield 68.0%；HRMS (EI): calculated value 667.2624, measured value 667.2614.
Embodiment 9: the synthesis of compound 131:
The preparation method is the same as that of Example 1 for compound 131, the difference is that raw material N1 is replaced with raw material N7, with raw material M2
Substitute M1.HPLC purity 99.4%, yield 68.0%；HRMS (EI): calculated value 617.2467, measured value 617.2457.
Embodiment 10: the synthesis of compound 158:
The preparation method is the same as that of Example 1 for compound 158, the difference is that raw material N1 is replaced with raw material N2, with raw material M4
Substitute M1.HPLC purity 99.4%, yield 68.0%；HRMS (EI): calculated value 567.2674, measured value 567.2671.
Embodiment 11: the synthesis of compound 168:
The preparation method is the same as that of Example 1 for compound 158, the difference is that substituting M1 with raw material M5.HPLC purity
98.4%, yield 77.0%；HRMS (EI): calculated value 567.2674, measured value 567.2694.
Embodiment 12: the synthesis of compound 188:
The preparation method of compound 188 is with embodiment 3, the difference is that substituting B1 with intermediate B 6.HPLC purity
96.4%, yield 79.6%；HRMS (EI): calculated value 643.2687, measured value 643.2614.
Embodiment 13: the synthesis of compound 203:
The preparation method is the same as that of Example 1 for compound 203, the difference is that substituting M1 with raw material M6.HPLC purity
98.4%, yield 77.0%；HRMS (EI): calculated value 616.2627, measured value 616.2694.
Embodiment 14: the synthesis of compound 213:
The preparation method is the same as that of Example 1 for compound 158, the difference is that substituting M1 with raw material M7.HPLC purity
99.4%, yield 68.0%；HRMS (EI): calculated value 616.2627, measured value 616.2666.
Embodiment 15: the synthesis of compound 218:
The preparation method is the same as that of Example 1 for compound 218, the difference is that substituting M1 with raw material M6.HPLC purity
98.4%, yield 77.0%；HRMS (EI): calculated value 691.2987, measured value 691.2994.
Embodiment 16: the synthesis of compound 233:
The preparation method is the same as that of Example 1 for compound 233, the difference is that raw material N1 is replaced with raw material N5, with raw material M9
Substitute M1.HPLC purity 99.4%, yield 68.0%；HRMS (EI): calculated value 590.2107, measured value 590.2174.
Embodiment 17: the synthesis of compound 272:
The preparation method is the same as that of Example 1 for compound 158, the difference is that substituting M1 with raw material M10.HPLC purity
97.4%, yield 68.0%；HRMS (EI): calculated value 785.3518, measured value 785.3571.
Embodiment 18: the synthesis of compound 273:
The preparation method is the same as that of Example 1 for compound 273, the difference is that replacing raw material N1 with raw material N2, raw material M11 is replaced
Change raw material M1, HPLC purity 98.7%, yield 58.0%；HRMS (EI): calculated value 631.2260, measured value 631.2271.
Embodiment 19: the synthesis of compound 281:
The preparation method is the same as that of Example 1 for compound 281, the difference is that replacing raw material N1 with raw material N2, raw material M12 is replaced
Change raw material M1, HPLC purity 98.7%, yield 58.0%；HRMS (EI): calculated value 708.2289, measured value 708.2271.
This organic compound uses in luminescent device, Tg (glass transition temperature) with higher and triplet
(T1), suitable HOMO, lumo energy act not only as hole transmission layer/electronic barrier layer materials'use, are alternatively arranged as sending out
Photosphere materials'use.Carry out hot property, T1 energy level and the test of HOMO energy level, knot respectively to the compounds of this invention and current material
Fruit is as shown in table 2.
Table 2
Note: triplet T1 is tested by the F4600 Fluorescence Spectrometer of Hitachi, and the test condition of material is 2*10-5's
Toluene solution；Glass transition temperature Tg is by differential scanning calorimetry (DSC, German Nai Chi company DSC204F1 differential scanning calorimeter)
Measurement, 10 DEG C/min of heating rate；Highest occupied molecular orbital HOMO energy level and minimum occupied molecular orbital lumo energy be by
Ionization energy test macro (IPS-3) test, is tested as atmospheric environment.
By upper table data it is found that NPB, CBP and TAPC material that comparison is applied at present, organic compound of the invention have
High glass transition temperature can be improved material membrane phase stability, further increase device service life；Material of the present invention and
While application material has similar HOMO energy level at present, also there is high triplet (T1), luminescent layer can be stopped
Energy loss, to promote device light emitting efficiency.Therefore, the organic material that the present invention contains spiral shell dimethylanthracene fluorenes is being applied to
After the different function layer of OLED device, the luminous efficiency and service life of device can be effectively improved.
Below by way of device embodiments 1~19 and device comparative example 1 OLED material that the present invention will be described in detail synthesizes in device
Application effect in part.Device embodiments 2~19 of the present invention, the device compared with device embodiments 1 of device comparative example 1
Manufacture craft it is identical, and use identical baseplate material and electrode material, the film thickness of electrode material is also kept
Unanimously, except that device embodiments 1-19 converts the functional layer material in device, each embodiment obtained device
The performance test results are as shown in table 3.
Device embodiments 1:
As shown in Figure 1, a kind of electroluminescent device, preparation step include:
A) the ito anode layer 2 on transparent substrate layer 1 is cleaned, cleans each 15 with deionized water, acetone, EtOH Sonicate respectively
Minute, then handled 2 minutes in plasma cleaner；
B) on ito anode layer 2, hole injection layer material HAT-CN is deposited by vacuum evaporation mode, with a thickness of 10nm,
This layer is as hole injection layer 3；
C) on hole injection layer 3, hole mobile material NPB is deposited by vacuum evaporation mode, with a thickness of 60nm, the layer
For hole transmission layer 4；
D) electronic barrier layer 5 is deposited by vacuum evaporation mode on hole transmission layer 4, electronic blocking layer material is this hair
The compound 3 of bright embodiment preparation, with a thickness of 20nm；
E) luminescent layer 6, material of main part CBP are deposited on electronic barrier layer 5, dopant material is Ir (ppy)3, CBP and
Ir(ppy)3Mass ratio is 90:10, with a thickness of 40nm；
F) on luminescent layer 6, electron transport material TPBI is deposited by vacuum evaporation mode, with a thickness of 35nm, this layer
Organic material is used as hole barrier/electron transfer layer 7；
G) on hole barrier/electron transfer layer 7, vacuum evaporation electron injecting layer LiF, with a thickness of 1nm, which is electricity
Sub- implanted layer 8；
H) on electron injecting layer 8, vacuum evaporation cathode Al (100nm), the layer is cathode reflection electrode layer 9；
After the production for completing electroluminescent device according to above-mentioned steps, the driving voltage of measurement device, current efficiency, knot
Fruit is shown in Table 3.The molecular structural formula of associated materials is as follows:
Device embodiments 2:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB) (thickness: 20nm, material: embodiment of the present invention system of/electronic barrier layer 5
Standby compound 12) (the thickness: 40nm, material: CBP and Ir (ppy) of/luminescent layer 63Constituted by weight 88:12 blending)/hole
Blocking/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/Al (thickness:
100nm)。
Device embodiments 3:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB) (thickness: 20nm, material: embodiment of the present invention system of/electronic barrier layer 5
Standby compound 66) (the thickness: 40nm, material: CBP and Ir (ppy) of/luminescent layer 63Constituted by weight 92:8 blending)/hole
Blocking/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/Al (thickness:
100nm)。
Device embodiments 4:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB) (thickness: 20nm, material: embodiment of the present invention system of/electronic barrier layer 5
Standby compound 83) (the thickness: 40nm, material: CBP, GH and Ir (ppy) of/luminescent layer 63By weight 70:30:10 blending structure
At)/hole barrier/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/
Al (thickness: 100nm).
Device embodiments 5:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB)/electronic barrier layer 5 (thickness: 20nm, material: TAPC)/luminescent layer 6
(thickness: 40nm, material: compound 99, GH and the Ir (ppy) of preparation of the embodiment of the present invention3By weight 60:40:10 blending structure
At)/hole barrier/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/
Al (thickness: 100nm).
Device embodiments 6:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB)/electronic barrier layer 5 (thickness: 20nm, material: TAPC)/luminescent layer 6
(thickness: 40nm, material: compound 105, GH and the Ir (ppy) of preparation of the embodiment of the present invention3By weight 40:60:10 blending
Constitute)/hole barrier/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material:
LiF)/Al (thickness: 100nm).
Device embodiments 7:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB) (thickness: 20nm, material: embodiment of the present invention system of/electronic barrier layer 5
Standby compound 113) (the thickness: 40nm, material: CBP and Ir (ppy) of/luminescent layer 63Constituted by weight 90:10 blending)/empty
Cave blocking/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/Al is (thick
Degree: 100nm).
Device embodiments 8:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB) (thickness: 20nm, material: embodiment of the present invention system of/electronic barrier layer 5
Standby compound 119) (the thickness: 40nm, material: CBP and Ir (ppy) of/luminescent layer 63Constituted by weight 92:8 blending)/hole
Blocking/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/Al (thickness:
100nm)。
Device embodiments 9:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB) (thickness: 20nm, material: embodiment of the present invention system of/electronic barrier layer 5
Standby compound 131) (the thickness: 40nm, material: CBP and Ir (ppy) of/luminescent layer 63Constituted by weight 88:12 blending)/empty
Cave blocking/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/Al is (thick
Degree: 100nm).
Device embodiments 10:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB) (thickness: 20nm, material: embodiment of the present invention system of/electronic barrier layer 5
Standby compound 158) (the thickness: 40nm, material: CBP and Ir (ppy) of/luminescent layer 63Constituted by weight 88:12 blending)/empty
Cave blocking/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/Al is (thick
Degree: 100nm).
Device embodiments 11:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB) (thickness: 20nm, material: embodiment of the present invention system of/electronic barrier layer 5
Standby compound 168) (the thickness: 40nm, material: CBP and Ir (ppy) of/luminescent layer 63Constituted by weight 90:10 blending)/empty
Cave blocking/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/Al is (thick
Degree: 100nm).
Device embodiments 12:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB)/electronic barrier layer 5 (thickness: 20nm, material: TAPC)/luminescent layer 6
(thickness: 40nm, material: compound 188, GH and the Ir (ppy) of preparation of the embodiment of the present invention3By weight 50:50:10 blending
Constitute)/hole barrier/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material:
LiF)/Al (thickness: 100nm).
Device embodiments 13:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB) (thickness: 20nm, material: embodiment of the present invention system of/electronic barrier layer 5
Standby compound 203) (the thickness: 40nm, material: CBP and Ir (ppy) of/luminescent layer 63Constituted by weight 90:10 blending)/empty
Cave blocking/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/Al is (thick
Degree: 100nm).
Device embodiments 14:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB) (thickness: 20nm, material: embodiment of the present invention system of/electronic barrier layer 5
Standby compound 213) (the thickness: 40nm, material: CBP and Ir (ppy) of/luminescent layer 63Constituted by weight 90:10 blending)/empty
Cave blocking/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/Al is (thick
Degree: 100nm).
Device embodiments 15:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB)/electronic barrier layer 5 (thickness: 20nm, material: TAPC)/luminescent layer 6
(thickness: 40nm, material: the compound 218 and Ir (ppy) of preparation of the embodiment of the present invention3Constituted by weight 90:10 blending)/
Hole barrier/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/Al
(thickness: 100nm).
Device embodiments 16:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB) (thickness: 20nm, material: embodiment of the present invention system of/electronic barrier layer 5
Standby compound 233) (the thickness: 40nm, material: CBP and Ir (ppy) of/luminescent layer 63Constituted by weight 90:10 blending)/empty
Cave blocking/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/Al is (thick
Degree: 100nm).
Device embodiments 17:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB) (thickness: 20nm, material: embodiment of the present invention system of/electronic barrier layer 5
Standby compound 272) (the thickness: 40nm, material: CBP and Ir (ppy) of/luminescent layer 63Constituted by weight 90:10 blending)/empty
Cave blocking/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/Al is (thick
Degree: 100nm).
Device embodiments 18:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB)/electronic barrier layer 5 (thickness: 20nm, material: TAPC)/luminescent layer 6
(thickness: 40nm, material: the compounds of this invention 273 and Ir (ppy)3Constituted by weight 90:10 blending)/hole barrier/electronics
Transport layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 19:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB) (thickness: 20nm, material: embodiment of the present invention system of/electronic barrier layer 5
Standby compound 281) (the thickness: 40nm, material: CBP and Ir (ppy) of/luminescent layer 63Constituted by weight 90:10 blending)/empty
Cave blocking/electron transfer layer 7 (thickness: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/Al is (thick
Degree: 100nm).
Device comparative example 1:ITO anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HAT-
CN)/hole transmission layer 4 (thickness: 60nm, material: NPB)/electronic barrier layer 5 (thickness: 20nm, material: TAPC)/luminescent layer 6
(thickness: 40nm, material: CBP and Ir (ppy)3Constituted by weight 90:10 blending)/hole barrier/electron transfer layer 7 (thickness
Degree: 35nm, material: TPBI)/electron injecting layer 8 (thickness: 1nm, material: LiF)/Al (thickness: 100nm).
The detection data of gained electroluminescent device is shown in Table 3.
Table 3
| Number | Current efficiency (cd/A) | Color | LT95 service life (Hr)@5000nits |
| Device embodiments 1 | 53.8 | Green light | 35.5 |
| Device embodiments 2 | 48.1 | Green light | 23.7 |
| Device embodiments 3 | 46.2 | Green light | 32.3 |
| Device embodiments 4 | 45.8 | Green light | 26.2 |
| Device embodiments 5 | 58.9 | Green light | 45.6 |
| Device embodiments 6 | 64.4 | Green light | 49.5 |
| Device embodiments 7 | 47.2 | Green light | 26.1 |
| Device embodiments 8 | 43.1 | Green light | 26.5 |
| Device embodiments 9 | 44.1 | Green light | 23.7 |
| Device embodiments 10 | 43.1 | Green light | 26.3 |
| Device embodiments 11 | 53.1 | Green light | 43.5 |
| Device embodiments 12 | 56.9 | Green light | 46.1 |
| Device embodiments 13 | 40.9 | Green light | 21.3 |
| Device embodiments 14 | 39.5 | Green light | 29.8 |
| Device embodiments 15 | 60.1 | Green light | 29.3 |
| Device embodiments 16 | 45.1 | Green light | 29.8 |
| Device embodiments 17 | 42.6 | Green light | 28.5 |
| Device embodiments 18 | 57.9 | Green light | 40.5 |
| Device embodiments 19 | 42.1 | Green light | 28.7 |
| Device comparative example 1 | 32.5 | Green light | 14.3 |
Organic compound of the present invention can be applied to the production of OLED luminescent device it can be seen from the result of table 3, and with than
It is compared compared with example, either efficiency or service life obtain larger change, the especially service life of device than known OLED material
Obtain biggish promotion.Further, work limitation rate is also more stable at low temperature for the OLED device of material preparation of the present invention,
By device embodiments 1,6,14 and device comparative example 1 in -10~80 DEG C of progress efficiency tests, acquired results are as shown in table 4, Fig. 2.
Table 4
From the data of table 4 it is found that the device architecture and device ratio of 1,6,14 material of device embodiments and known materials collocation
It is compared compared with example 1, not only Efficiency at Low Temperature is high, but also in temperature elevation process, efficiency is steadily increased.
To sum up, the foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Within mind and principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (11)
1. a kind of using pyridine diindyl as the compound of core, which is characterized in that shown in the compound structure such as general formula (1):
In general formula (1), Ar is expressed as the C for being substituted or being unsubstituted6To C30Aryl, the C for being substituted or being unsubstituted5To C30It is miscellaneous
One of aryl；
In general formula (1), X1, X2, X3, X4Independently be expressed as C-H or N, and at least one is expressed as N atom；
In general formula (1), R is expressed as structure shown in general formula (2)；
In general formula (2), L be represented by singly-bound, substituted or unsubstituted C6-60 arlydene, substituted or unsubstituted 5~60 yuan it is miscellaneous
Arlydene, the hetero atom in the heteroarylidene are nitrogen, oxygen or sulphur；
In general formula (2), X5It is expressed as the alkylene that alkylidene, the aryl that oxygen, sulphur, selenium, C1-10 linear or branched alkyl group replace replace
One of the imido grpup that base, alkyl-substituted imido grpup or aryl replace；
In general formula (2), R1、R2Independently be expressed as hydrogen, general formula (3), general formula (4), structure in general formula (5) or general formula (6)；
In general formula (3) and general formula (4), X6、X7、X8Independently be expressed as oxygen, sulphur, C1-10The Asia that linear or branched alkyl group replaces
One of the imido grpup that alkylidene, alkyl-substituted imido grpup or the aryl that alkyl, aryl replace replace；
General formula (3), general formula (4), general formula (5) pass through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL4-CL5Key, CL’1-CL’2Key,
CL'2-CL’3Key CL’3-CL’4Key or CL’4-CL’5It is connected with general formula (2) and ring；
In general formula (6), R3、R4Independently be expressed as phenyl, naphthalene, dibiphenylyl, terphenyl, carbazyl, furyl,
One in pyridyl group, phenanthryl, anthryl, dibenzofuran group, dibenzothiophene, 9,9- dimethyl fluorenyl or N- phenyl carbazole base
Kind, R3 and R4 are same or different.
2. compound according to claim 1, which is characterized in that shown in the compound structure such as formula (I)~(IV):
3. organic compound according to claim 1, which is characterized in that general formula (2) structure such as (1)~(12) institute
Show:
4. organic compound according to claim 1, which is characterized in that described Ar, R3And R4Expression independently are as follows:
In
It is any.
5. organic compound according to claim 1, which is characterized in that the L is indicated are as follows: singly-bound, Any one of.
6. compound according to claim 1, it is characterised in that the specific structure of the compound are as follows:
Any one of.
7. a kind of preparation method of compound as described in any one of claims 1 to 6, which is characterized in that
(1) when L is singly-bound, the raw material N containing pyrido indolyl radical is connected with the R group of raw material M with C-N key, preparation
The reaction equation of the compound are as follows:
The preparation method comprises the following steps: raw material N and raw material M are dissolved in dry toluene, sodium tert-butoxide and Pd (dppf) Cl are added after deoxygenation2,
95~110 DEG C of 10~24 hours of reaction under an inert atmosphere monitor reaction process with TLC in reaction process, react to raw material
After completely, filtrate is rotated and removes solvent by cooling, filtering, and crude product crosses silicagel column, obtains target compound；
Wherein, the molar ratio of the raw material N and raw material M is 1:(1.1~2.5), Pd (dppf) Cl2Molar ratio with raw material N is
(0.006~0.02): 1, the molar ratio of sodium tert-butoxide and raw material N are (1.5~2): 1；
(2) when L is not singly-bound, pyridine diindyl is connected with R with C-C key,
Specifically the preparation method comprises the following steps: using raw material N and intermediate B as raw material, Pd (PPh is added in toluene dissolution after deoxygenation3)4And carbonic acid
Sodium by above-mentioned mixed solution in 95~110 DEG C, reacts 10~24 hours, cooled to room temperature, and mistake under nitrogen protection
Reaction solution is filtered, filtrate carries out vacuum rotary steam, crosses neutral silica gel column, obtains target compound；
Wherein, toluene dosage is that every gram of raw material N uses 30-50ml toluene, the molar ratio of raw material N and intermediate B be 1:(1.0~
1.5)；Pd(PPh3)4It is (0.005~0.01) with the molar ratio of raw material N: 1, the molar ratio of the sodium carbonate and raw material N are (1.5
~3.0): 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
Containing described in claim 1~6 using pyridine diindyl as the organic compound of core.
9. a kind of organic electroluminescence device, including hole transmission layer/electronic barrier layer, which is characterized in that the cave transport layer/
Electronic blocking layer material is that claim 1~6 is described in any item using pyridine diindyl as the compound of core.
10. a kind of organic electroluminescence device, including luminescent layer, which is characterized in that the luminescent layer includes claim 1~6
It is described in any item using pyridine diindyl as the compound of core.
11. a kind of illumination or display element, which is characterized in that including the organic electroluminescent as described in claim 8-10 is any
Device.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111718341A (en) * | 2020-07-10 | 2020-09-29 | 北京燕化集联光电技术有限公司 | Carbazole ring-containing compound and application thereof in organic electroluminescent device |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140076520A (en) * | 2012-12-12 | 2014-06-20 | 에스에프씨 주식회사 | An electroluminescent compound and an electroluminescent device comprising the same |
| CN106220619A (en) * | 2016-04-25 | 2016-12-14 | 中节能万润股份有限公司 | A kind of organic compound containing xanthene structure and application thereof |
| KR20170057796A (en) * | 2015-11-17 | 2017-05-25 | 에스케이케미칼주식회사 | Compound for organic electroluminescent device and organic electroluminescent device comprising the same |
| CN106800555A (en) * | 2017-01-19 | 2017-06-06 | 江西冠能光电材料有限公司 | A kind of organic semiconductor material of main part and its Organic Light Emitting Diode application |
| CN106883218A (en) * | 2017-03-29 | 2017-06-23 | 江苏三月光电科技有限公司 | A kind of organic compound with equal benzene as core and its application on organic electroluminescence device |
| WO2017115608A1 (en) * | 2015-12-28 | 2017-07-06 | コニカミノルタ株式会社 | π-CONJUGATED COMPOUND, ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, LIGHT EMITTING MATERIAL, CHARGE TRANSPORT MATERIAL, LUMINESCENT THIN FILM, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE |
| CN108976212A (en) * | 2017-06-02 | 2018-12-11 | 北京鼎材科技有限公司 | Fluorene derivative and its application in luminous organic material |
| CN109400603A (en) * | 2017-08-16 | 2019-03-01 | 北京鼎材科技有限公司 | Compound and its application in organic light emission field |
-
2017
- 2017-11-16 CN CN201711139461.7A patent/CN109796473A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140076520A (en) * | 2012-12-12 | 2014-06-20 | 에스에프씨 주식회사 | An electroluminescent compound and an electroluminescent device comprising the same |
| KR20170057796A (en) * | 2015-11-17 | 2017-05-25 | 에스케이케미칼주식회사 | Compound for organic electroluminescent device and organic electroluminescent device comprising the same |
| WO2017115608A1 (en) * | 2015-12-28 | 2017-07-06 | コニカミノルタ株式会社 | π-CONJUGATED COMPOUND, ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, LIGHT EMITTING MATERIAL, CHARGE TRANSPORT MATERIAL, LUMINESCENT THIN FILM, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE |
| CN106220619A (en) * | 2016-04-25 | 2016-12-14 | 中节能万润股份有限公司 | A kind of organic compound containing xanthene structure and application thereof |
| CN106800555A (en) * | 2017-01-19 | 2017-06-06 | 江西冠能光电材料有限公司 | A kind of organic semiconductor material of main part and its Organic Light Emitting Diode application |
| CN106883218A (en) * | 2017-03-29 | 2017-06-23 | 江苏三月光电科技有限公司 | A kind of organic compound with equal benzene as core and its application on organic electroluminescence device |
| CN108976212A (en) * | 2017-06-02 | 2018-12-11 | 北京鼎材科技有限公司 | Fluorene derivative and its application in luminous organic material |
| CN109400603A (en) * | 2017-08-16 | 2019-03-01 | 北京鼎材科技有限公司 | Compound and its application in organic light emission field |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111718341A (en) * | 2020-07-10 | 2020-09-29 | 北京燕化集联光电技术有限公司 | Carbazole ring-containing compound and application thereof in organic electroluminescent device |
| CN111718341B (en) * | 2020-07-10 | 2021-08-17 | 北京燕化集联光电技术有限公司 | Compound containing pyridoindole structure and application thereof in organic electroluminescent device |
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