CN108440396A - A kind of luminous organic material and its preparation method and application - Google Patents

A kind of luminous organic material and its preparation method and application Download PDF

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CN108440396A
CN108440396A CN201810249626.4A CN201810249626A CN108440396A CN 108440396 A CN108440396 A CN 108440396A CN 201810249626 A CN201810249626 A CN 201810249626A CN 108440396 A CN108440396 A CN 108440396A
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formula
nitrogen
organic material
luminous organic
present
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马晓宇
王辉
李文军
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Jilin Optical and Electronic Materials Co Ltd
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The present invention provides a kind of luminous organic materials and preparation method thereof, luminous organic material provided by the invention with formula (I) structure is by the way that the asymmetric anthracene of specific structure to be connected with the derivative of tri-arylamine group of specific structure, the experimental results showed that the electroluminescent device that the luminous organic material that the present invention obtains is obtained as electron transport layer materials or delayed fluorescence class material preparation has higher brightness, preferable heat resistance, long-life and high luminous efficiency.

Description

A kind of luminous organic material and its preparation method and application
Technical field
The present invention relates to field of organic electroluminescent materials more particularly to a kind of luminous organic material and preparation method thereof and Using.
Background technology
Organic electroluminescent (EL) is generally by two opposed electrodes and at least one layer being inserted between two electrodes Organic luminescent compounds form.Charge is injected into the organic layer formed between the anode and cathode, to form electronics and sky Cave pair makes the organic compound with fluorescence or phosphorescent characteristics produce light emitting.
Research for electroluminescent organic material is from nineteen fifty Bernose to the macromolecule membrane containing organic pigment Apply what high current voltage observed.Nineteen sixty-five, Pope et al. are found that the Electroluminescence Properties of anthracene single crystal for the first time, this is organic The first electro optical phenomenon of compound.For the high organic luminescent device of producing efficiency, researcher is gradually organic in device The structure of nitride layer becomes multilayered structure from single layer.It is the movement speed due to hole and electronics that El element, which is designed as multilayered structure, Difference, it is appropriate to design hole injection layer, hole transmission layer, electron transfer layer and electron injecting layer, improve hole and electricity The efficiency of transmission of son makes hole and electronics in device reach balanced, to improve luminous efficiency, in the structure for changing luminescent device While, researchers are also actively working to provide the luminescent material of better performances.
Invention content
In view of this, technical problem to be solved by the present invention lies in a kind of luminous organic material and preparation method thereof and answering With material provided by the invention can be improved as organic electroluminescence device volume electron transport material or delayed fluorescence class material The luminous efficiency of device.
The present invention provides a kind of luminous organic materials, have formula (I) structure,
Wherein, X1-a、X1-b、X1-c、X1-d、X1-eIt is independent to be selected from carbon or nitrogen；
X2-a、X2-b、X2-c、X2-d、X2-eIt is independent to be selected from carbon or nitrogen；
R is selected from the heteroaryl of C8~C35, wherein the hetero atom in heteroaryl is one or more of oxygen, sulphur and nitrogen.
Preferably, the X1-a、X1-b、X1-c、X1-dAnd X1-eIn at least one be nitrogen.
Preferably, X2-a、X2-b、X2-c、X2-dAnd X2-eIn at least one be nitrogen.
Preferably, the R is the heteroaryl of C11~C25.
Preferably, the R is formula (R-1), formula (R-2), formula (R-3), formula (R-4), formula (R-5), formula (R-6), formula (R- 7), formula (R-8), formula (R-9), formula (R-10), formula (R-11), formula (R-12), formula (R-13), formula (R-14), formula (R-15), formula (R-16),
Preferably, the luminous organic material has formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-5), formula (I-6), formula (I-7), formula (I-8), formula (I-9), formula (I-10), formula (I-11), formula (I-12), formula (I-13), formula (I-14), formula (I-15), formula (I-16), formula (I-17), formula (I-18), formula (I-19), formula (I-20), formula (I-21), formula (I-22), formula (I- 23), formula (I-24), formula (I-25), formula (I-26), formula (I-27), formula (I-28), formula (I-29), formula (I-30), formula (I-31), Formula (I-32), formula (I-33), formula (I-34),
Wherein, R is selected from the heteroaryl of C8~C35, wherein hetero atom in heteroaryl be one kind in oxygen, sulphur and nitrogen or It is several.
Preferably, the luminous organic material has formula (001), formula (002), formula (003), formula (004), formula (005), formula (006), formula (007), formula (008), formula (009), formula (010), formula (011), formula (012), formula (013), formula (014), formula (015), formula (016), formula (017), formula (018), formula (019), formula (020), formula (021), formula (022), formula (023), formula (024), formula (025), formula (026), formula (027), formula (028), formula (029), formula (030), formula (031), formula (032), formula (033), formula (034), formula (035), formula (036), formula (037), formula (038), formula (039), formula (040), formula (041), formula (042), formula (043), formula (044), formula (045), formula (046), formula (047), formula (048), formula (049), formula (050), formula (051), formula (052), formula (053), formula (054), formula (055), formula (056), formula (057), formula (058), formula (059), formula (060),
The present invention also provides a kind of preparation methods of luminous organic material, including：By amine chemical combination shown in formula (II) Object is reacted with halides shown in formula (III), obtains luminous organic material shown in formula (1)；
Wherein, X is halogen；
X1-a、X1-b、X1-c、X1-d、X1-eIt is independent to be selected from carbon or nitrogen；
X2-a、X2-b、X2-c、X2-d、X2-eIt is independent to be selected from carbon or nitrogen；
R is selected from the heteroaryl of C8~C35, wherein the hetero atom in heteroaryl is one or more of oxygen, sulphur and nitrogen.
The present invention also provides luminous organic materials of the present invention as electron transport layer materials is preparing Organic Electricity Cause the application given out light in device.
The present invention also provides a kind of luminous organic materials of the present invention to have as delayed fluorescence class material in preparation Electromechanics causes the application given out light in device.
Compared with prior art, the luminous organic material provided by the invention with formula (I) structure is by by specific structure Asymmetric anthracene be connected with the derivative of tri-arylamine group of specific structure, the experimental results showed that, the organic light emission that the present invention obtains The electroluminescent device that material is obtained as electron transport layer materials or delayed fluorescence class material preparation have higher brightness, compared with Good heat resistance, long-life and high luminous efficiency.
Specific implementation mode
The present invention provides a kind of luminous organic materials, have formula (I) structure,
Wherein, X1-a、X1-b、X1-c、X1-d、X1-eIt is independent to be selected from carbon or nitrogen；
X2-a、X2-b、X2-c、X2-d、X2-eIt is independent to be selected from carbon or nitrogen；
R is selected from the heteroaryl of C8~C35, wherein the hetero atom in heteroaryl is one or more of oxygen, sulphur and nitrogen.
According to the present invention, the X1-a、X1-b、X1-c、X1-dAnd X1-eIn preferably have zero be nitrogen, one be nitrogen, two be Nitrogen, three be nitrogen or four are nitrogen；More preferably there are two be nitrogen, three be nitrogen or four are nitrogen.
According to the present invention, the X2-a、X2-b、X2-c、X2-dAnd X2-eIn preferably have zero be nitrogen, one be nitrogen, two be Nitrogen, three be nitrogen or four are nitrogen；More preferably there are two be nitrogen, three be nitrogen or four are nitrogen.According to the present invention, the R The preferably heteroaryl of C11~C25, more preferably formula (R-1), formula (R-2), formula (R-3), formula (R-4), formula (R-5), formula (R- 6), formula (R-7), formula (R-8), formula (R-9), formula (R-10), formula (R-11), formula (R-12), formula (R-13), formula (R-14), formula (R- 15), formula (R-16), whereinFor connecting key.
Specifically, the luminous organic material has formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-5), formula (I-6), formula (I-7), formula (I-8), formula (I-9), formula (I-10), formula (I-11), formula (I-12), formula (I-13), formula (I-14), formula (I-15), formula (I-16), formula (I-17), formula (I-18), formula (I-19), formula (I-20), formula (I-21), formula (I-22), formula (I- 23), formula (I-24), formula (I-25), formula (I-26), formula (I-27), formula (I-28), formula (I-29), formula (I-30), formula (I-31), Formula (I-32), formula (I-33), formula (I-34),
Wherein, R is selected from the heteroaryl of C8~C35, wherein hetero atom in heteroaryl be one kind in oxygen, sulphur and nitrogen or It is several.
More specifically, the luminous organic material have formula (001), formula (002), formula (003), formula (004), formula (005), Formula (006), formula (007), formula (008), formula (009), formula (010), formula (011), formula (012), formula (013), formula (014), formula (015), formula (016), formula (017), formula (018), formula (019), formula (020), formula (021), formula (022), formula (023), formula (024), formula (025), formula (026), formula (027), formula (028), formula (029), formula (030), formula (031), formula (032), formula (033), formula (034), formula (035), formula (036), formula (037), formula (038), formula (039), formula (040), formula (041), formula (042), formula (043), formula (044), formula (045), formula (046), formula (047), formula (048), formula (049), formula (050), formula (051), formula (052), formula (053), formula (054), formula (055), formula (056), formula (057), formula (058), formula (059), formula (060),
The present invention also provides a kind of preparation methods of luminous organic material, including：By amine chemical combination shown in formula (II) Object is reacted with halides shown in formula (III), obtains luminous organic material shown in formula (1)；
Wherein, X is halogen, preferably chlorine, bromine or iodine.
X1-a、X1-b、X1-c、X1-d、X1-eIt is independent to be selected from carbon or nitrogen；
X2-a、X2-b、X2-c、X2-d、X2-eIt is independent to be selected from carbon or nitrogen；
R is selected from the heteroaryl of C8~C35, wherein the hetero atom in heteroaryl is one or more of oxygen, sulphur and nitrogen.
According to the present invention, the present invention carries out halides shown in aminated compounds shown in formula (II) and formula (III) anti- It answers, obtains luminous organic material shown in formula (1)；Wherein, the present invention does not have particular/special requirement, art technology to the condition of reaction Personnel can select suitable method according to actual needs, it is preferred that the catalyst of reaction of the present invention is three (two sub- benzyl groups Acetone) two palladiums and tri-tert-butylphosphine；The alkali of the reaction is preferably potassium tert-butoxide.
The present invention provides a kind of luminous organic material of the present invention as electron transport layer materials prepare it is organic Application in electroluminescent device of giving out light.
The present invention also provides a kind of luminous organic materials of the present invention to have as delayed fluorescence class material in preparation Electromechanics causes the application given out light in device.
Luminous organic material provided by the invention with formula (I) structure by by the asymmetric anthracene of specific structure with it is specific The derivative of tri-arylamine group of structure is connected so that the electroluminescent device that the luminous organic material that the present invention obtains is prepared With higher brightness, preferable heat resistance, long-life and high luminous efficiency.And the luminous organic material is passed as electronics Defeated material or the organic electroluminescence device of delayed fluorescence class material preparation are applicable to organic photovoltaic cell, Electronic Paper, organic Photoreceptor or organic transistor.
It is clearly and completely described below in conjunction with the technical solution of the embodiment of the present invention, it is clear that described implementation Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field is common The every other embodiment that technical staff is obtained without making creative work belongs to the model that the present invention protects It encloses.
Embodiment 1
The synthesis of compound 001
Under the conditions of nitrogen protection, 0.10mol compounds [1-1], sodium tert-butoxide 0.30mol, first are added into reaction bulb Benzene 400mL is stirred 30 minutes, nitrogen protection, and 0.12mol compounds [1-2], three (dibenzylideneacetone) two palladium is then added 1.5g is eventually adding tri-tert-butylphosphine 4g, is warming up to 100 DEG C and reacts 24 hours, after reaction, it is whole that water is added in system cooling It only reacts, filters, filtrate liquid separation is spin-dried for toluene, a small amount of dichloromethane dissolved solid, petroleum ether is added：Dichloromethane=3: 1 (volume ratio) crosses post separation, obtains solid 001 (0.05mol, y=50%), MS/FAB (M+)：805.34.
Embodiment 2
The compound of the 002-060 is prepared using raw material shown in following formula according to the preparation method of above compound 001. To obtained compound carry out Mass Spectrometer Method, the results are shown in Table 1, table 1 is the mass spectrometric data of the compound of 002-060, as a result table It is bright, it is consistent with the theoretical value of compound, it is target compound.
Formula (III)Shown in aminated compounds be selected from,
Formula (II)Shown in anthracene derivative be selected from,
1 compound mass spectrometry value of table
Serial number Actual measured value Serial number Actual measured value Serial number Actual measured value
021 729.32 041 653.29
002 650.25 022 728.35 042 767.35
003 650.24 023 729.31 043 771.32
004 728.27 024 652.29 044 787.32
005 727.32 025 652.30 045 767.35
006 727.25 026 653.30 046 652.29
007 726.34 027 767.35 047 652.31
008 726.32 028 771.33 048 653.30
009 650.30 029 787.31 049 732.25
010 650.29 030 767.33 050 731.26
011 650.28 031 651.24 051 732.25
012 765.35 032 651.23 052 729.33
013 768.33 033 651.22 053 730.35
014 784.32 034 729.31 054 655.29
015 766.35 035 728.33 055 654.29
016 651.33 036 729.34 056 655.28
017 651.29 037 728.35 057 771.33
018 651.30 038 729.27 058 773.32
019 729.34 039 652.30 059 789.32
020 728.32 040 652.29 060 769.33
Embodiment 3
Organic electroluminescence device prepares and performance evaluation
1) prepared by organic electroluminescence device
It is by Fisher Co., Ltd's coating layer thicknessIto glass substrate be placed in distilled water and clean 2 times, ultrasonic wave Washing 30 minutes, is then cleaned 2 times, ultrasonic washing 10 minutes repeatedly with distilled water, after distilled water cleans, using isopropyl Alcohol, acetone, methanol ultrasonic washing in order, then dry, are transferred in plasma washing machine, and aforesaid substrate is washed 5 Minute, it is sent in evaporator.Organic electroluminescence device include anode, hole injection layer, hole transmission layer, organic luminous layer, Electron transfer layer, layer of auxiliary material and cathode.Wherein, anode is indium tin oxide；Hole injection layer is thickness 60nm's (HAT-CN)；Hole transmission layer is [two-[4- (N, N- xylyl-amino)-phenyl] hexamethylenes (TAPC) of thickness 30nm； Organic luminous layer is thickness 10nm comprising the 4 of 90%, 4 '-bis- (carbazole -9- bases)-biphenyl, CBP) it is used as light emitting host material Material, and the luminous material doped with 10% 2 (1- phenyl-isoquinolin) (acetylacetone,2,4-pentanedione) conjunction iridium (III) (Ir (ppy) 2 (acac)) Material；Electron transfer layer is the compound of one or formula (D-1) in the compound 001~060 of thickness 50nm；Layer of auxiliary material is The LiF of thickness 1nm；And cathode is aluminium.Above process organic matter vaporization plating speed is keptThe evaporation rate of LiF isThe evaporation rate of Al is
The electron luminescence characteristic of organic electroluminescence device obtained by the above method is shown in Table 2, and table 2 is the embodiment of the present invention 3 The characteristics of luminescence test result of the organic electroluminescence device of preparation.
The characteristics of luminescence test result of organic electroluminescence device prepared by 2 embodiment of the present invention 3 of table
As shown in Table 2, using the compound of the present invention 001~060 as the organic electroluminescence device of electron transfer layer With preferable luminous efficiency.
2) life characteristic of embodiment 001~060 and formula (D-1) is evaluated
Utilize testing example on the basis of the LTS-1004AC endurance testing devices 3000nit of ENC technology companies 001~060 and formula (D-1) reached for 97% time as a result, being specifically shown according to organic electroluminescence device prepared by preceding method Table 3.
Table 3
It can be seen from Table 3 that compound of the present invention has better life characteristic compared with comparative example.
3) preparation of organic electroluminescence device
The ito glass substrate that Fisher Co., Ltd's coating layer thickness is is placed in distilled water and is cleaned 2 times, ultrasonic washing 30 divides Clock is cleaned 2 times repeatedly with distilled water, ultrasonic washing 10 minutes, and after distilled water cleans, isopropanol, acetone, methanol etc. are molten Ultrasonic washing is later dry in order for agent, is transferred in plasma washing machine, aforesaid substrate is washed 5 minutes, steaming is sent to In plating machine.
The above-mentioned glass substrate for being coated with ito transparent electrode is placed in vacuum chamber, is evacuated to 10-5-10-3Pa, vapor deposition Hole transmission layer NPB, evaporation rate 0.1nm/s, thickness 20nm.Hot activation in the vapor deposition present invention on the hole transport layer For the compound of one in delayed fluorescence material 001~060 or formula (D-1) as luminescent layer, evaporation rate 0.1nm/s is thick Degree is 30nm.One layer of AlQ of vacuum evaporation on the light-emitting layer3As electron transfer layer, evaporation rate 0.1nm/s, thickness is 20nm.Electron injecting layers and cathode of the vapor deposition LiF and Al as device, thickness distinguish 1nm and 100nm on the electron transport layer. The luminescent properties of measurement device, the results are shown in Table 4.
The characteristics of luminescence of luminescent device prepared by 4 embodiment of the present invention of table
As can be seen that the organic electroluminescence device prepared using luminous organic material provided by the invention, outer quantum effect Rate is high, and low with higher luminous efficiency, driving voltage, is a kind of excellent OLED material.
Luminous organic material using the present invention prepared by the present invention is as electron transport material or delayed fluorescence class material Organic electroluminescence device can obtain luminous efficiency and the service life is good as a result, so luminous organic material provided by the invention Occupy very important effect in the high OLED industries of practicability.The organic electroluminescence device of the present invention is that flat panel is aobvious Show, planar illuminant, illumination face illuminating OLED illuminator, flexible illuminator, duplicator, printer, LCD backlight lamp or metering The suitable use such as light source, display board, the mark of machine class.
The explanation of above example is only intended to facilitate the understanding of the method and its core concept of the invention.It should be pointed out that pair For those skilled in the art, without departing from the principle of the present invention, the present invention can also be carried out Some improvements and modifications, these improvement and modification are also fallen within the protection scope of the claims of the present invention.

Claims (10)

1. a kind of luminous organic material has formula (I) structure,
Wherein, X1-a、X1-b、X1-c、X1-d、X1-eIt is independent to be selected from carbon or nitrogen；
X2-a、X2-b、X2-c、X2-d、X2-eIt is independent to be selected from carbon or nitrogen；
R is selected from the heteroaryl of C8~C35, wherein the hetero atom in heteroaryl is one or more of oxygen, sulphur and nitrogen.
2. luminous organic material according to claim 1, which is characterized in that the X1-a、X1-b、X1-c、X1-dAnd X1-eIn have Zero be nitrogen, one be nitrogen, two be nitrogen, three be nitrogen or four are nitrogen.
3. luminous organic material according to claim 1, which is characterized in that the X2-a、X2-b、X2-c、X2-dAnd X2-eIn be Have zero be nitrogen, one be nitrogen, two be nitrogen, three be nitrogen or four are nitrogen.
4. luminous organic material according to claim 1, which is characterized in that the R is the heteroaryl of C11~C25.
5. luminous organic material according to claim 1, which is characterized in that the R is formula (R-1), formula (R-2), formula (R- 3), formula (R-4), formula (R-5), formula (R-6), formula (R-7), formula (R-8), formula (R-9), formula (R-10), formula (R-11), formula (R- 12), formula (R-13), formula (R-14), formula (R-15),
6. organic material according to claim 1, which is characterized in that the luminous organic material has formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-5), formula (I-6), formula (I-7), formula (I-8), formula (I-9), formula (I-10), formula (I- 11), formula (I-12), formula (I-13), formula (I-14), formula (I-15), formula (I-16), formula (I-17), formula (I-18), formula (I-19), Formula (I-20), formula (I-21), formula (I-22), formula (I-23), formula (I-24), formula (I-25), formula (I-26), formula (I-27), formula (I- 28), formula (I-29), formula (I-30), formula (I-31), formula (I-32), formula (I-33), formula (I-34),
Wherein, R is selected from the heteroaryl of C8~C35, wherein the hetero atom in heteroaryl is one or more of oxygen, sulphur and nitrogen.
7. organic material according to claim 1, which is characterized in that the luminous organic material has formula (001), formula (002), formula (003), formula (004), formula (005), formula (006), formula (007), formula (008), formula (009), formula (010), formula (011), formula (012), formula (013), formula (014), formula (015), formula (016), formula (017), formula (018), formula (019), formula (020), formula (021), formula (022), formula (023), formula (024), formula (025), formula (026), formula (027), formula (028), formula (029), formula (030), formula (031), formula (032), formula (033), formula (034), formula (035), formula (036), formula (037), formula (038), formula (039), formula (040), formula (041), formula (042), formula (043), formula (044), formula (045), formula (046), formula (047), formula (048), formula (049), formula (050), formula (051), formula (052), formula (053), formula (054), formula (055), formula (056), formula (057), formula (058), formula (059), formula (060),
8. a kind of preparation method of luminous organic material, including：Shown in aminated compounds shown in formula (II) and formula (III) Halides are reacted, and luminous organic material shown in formula (1) is obtained；
Wherein, X is halogen；
X1-a、X1-b、X1-c、X1-d、X1-eIt is independent to be selected from carbon or nitrogen；
X2-a、X2-b、X2-c、X2-d、X2-eIt is independent to be selected from carbon or nitrogen；
R is selected from the heteroaryl of C8~C35, wherein the hetero atom in heteroaryl is one or more of oxygen, sulphur and nitrogen.
9. a kind of luminous organic material described in claim 1~7 any one as electron transport layer materials prepare it is organic Application in electroluminescent device of giving out light.
10. a kind of luminous organic material described in claim 1~7 any one as delayed fluorescence class material prepare it is organic Application in electroluminescent device of giving out light.
CN201810249626.4A 2018-03-23 2018-03-23 A kind of luminous organic material and its preparation method and application Pending CN108440396A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111004213A (en) * 2019-12-26 2020-04-14 北京欣奕华科技有限公司 Organic electroluminescent compound and application thereof
CN112266353A (en) * 2020-10-20 2021-01-26 吉林奥来德光电材料股份有限公司 Aromatic anthracene organic light-emitting compound and preparation method and application thereof
WO2022255460A1 (en) * 2021-06-02 2022-12-08 日本農薬株式会社 Benzimidazole compound or salt thereof, canine filariasis control agent containing same, and method of use thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111004213A (en) * 2019-12-26 2020-04-14 北京欣奕华科技有限公司 Organic electroluminescent compound and application thereof
CN111004213B (en) * 2019-12-26 2021-07-20 北京欣奕华科技有限公司 Organic electroluminescent compound and application thereof
CN112266353A (en) * 2020-10-20 2021-01-26 吉林奥来德光电材料股份有限公司 Aromatic anthracene organic light-emitting compound and preparation method and application thereof
WO2022255460A1 (en) * 2021-06-02 2022-12-08 日本農薬株式会社 Benzimidazole compound or salt thereof, canine filariasis control agent containing same, and method of use thereof

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