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CN107311979A - Hot activation delayed fluorescence material and its organic electroluminescence device based on phenyl indazole derivative - Google Patents

Hot activation delayed fluorescence material and its organic electroluminescence device based on phenyl indazole derivative Download PDF

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CN107311979A
CN107311979A CN201710666338.4A CN201710666338A CN107311979A CN 107311979 A CN107311979 A CN 107311979A CN 201710666338 A CN201710666338 A CN 201710666338A CN 107311979 A CN107311979 A CN 107311979A
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delayed fluorescence
hot activation
activation delayed
phenyl
fluorescence material
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蔡辉
杜明珠
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Changchun Haipurunsi Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of hot activation delayed fluorescence material and its organic electroluminescence device based on phenyl indazole derivative, belongs to technical field of organic electroluminescence.Solve hot activation delayed fluorescence material category in the prior art single, it is impossible to meet the technical problem of OLED demand.The present invention is using phenyl indazole group as electron acceptor, using phenyl ring as connecting bridge, using arylamine or the hexa-atomic thick and heteroaromatic for containing nitrogen-atoms as electron donor, obtains a kind of hot activation delayed fluorescence material.Organic electroluminescence device prepared by the hot activation delayed fluorescence material provided using the present invention, external quantum efficiency is high, and maximum current efficiency is up to 18.63cd/A, maximum power efficiency is up to 20.31lm/W, with higher luminous efficiency, and driving voltage is low, is a kind of excellent OLED material.

Description

Hot activation delayed fluorescence material and its organic electroluminescence hair based on phenyl indazole derivative Optical device
Technical field
The present invention relates to technical field of organic electroluminescence, and in particular to a kind of hot activation based on phenyl indazole derivative Delayed fluorescence material and its organic electroluminescence device.
Background technology
Organic electroluminescent LED (Organic Light-Emitting Diode, OLED) refers to luminous organic material The diode lighted in the presence of electric current or electric field, electric energy can be converted into luminous energy by it.Kodak Company in 1987 Tang etc. has invented sandwich type organic bilayer film luminescent device, this breakthrough, allows it is seen that OLED technology Move towards practical, move towards the great potential of commercial market, started the research boom of Organic Light Emitting Diode.Over 30 years, OLED Technology achieves development with rapid changepl. never-ending changes and improvements, is moved towards the industrialization production from laboratory research.All solid state, the active of OLED technology Luminous, high-contrast, it is ultra-thin, can Flexible Displays, low-power consumption, wide viewing angle, fast response time, operating temperature range is wide, be easy to real Many advantages, such as existing 3D is shown, is referred to as " fantasy display " by professional, will turn into following most potential new Type Display Technique.
Certainly, the behind that OLED technology is advanced by leaps and bounds, luminous organic material plays an important role.Luminous organic material root It can be substantially divided into three classes according to luminescence mechanism：Conventional fluorescent material, phosphor material and hot activation delayed fluorescence (Thermally Activated Delayed Fluorescence, TADF) material.Wherein, conventional fluorescent material and phosphor material are in work Industry metaplasia production in be applied, but they still have it is clearly disadvantageous.Traditional fluorescent material, in the condition of electroexcitation Under, limited by spin quantum statistical theorem, singlet excitons and the triplet exciton ratio of number of formation are 1：3,75% Triplet exciton can only be dissipated in the form of heat and can not be luminous by radiation transistion, only 25% singlet excitons can It is luminous by radiation transistion, i.e., traditional fluorescent material highest internal quantum efficiency (Internal Quantum Efficiency, IQE it is only) 25%, if being 20% in view of optical coupling delivery efficiency, then the highest external quantum efficiency of its OLED (External Quantum Efficiency, EQE) is only 5%.Although fluorescent material OLED has higher reliability And stability, but relatively low external quantum efficiency still limits its application.And phosphor material generally comprises rare precious metals, cause Expensive, and device stability energy is poor, device efficiency declines serious the problems such as, all largely further limit Its extensive commercial popularization.In recent years, hot activation delayed fluorescence material has been increasingly becoming the new focus of this area research.The material 100% internal quantum efficiency can be realized under conditions of non precious metal, the use of the heavy metal of costliness can be not only avoided, from And cost is reduced to a certain extent, and it can be desirable to device lifetime and spectrum stability are greatly improved, while having luminous effect The advantage such as rate is high, environment-friendly, is referred to as third generation electroluminescent material.
But, the correlative study on hot activation delayed fluorescence material is also fewer at present, and material category is still single, nothing Method meets the exploitation demand of OLED, and novel high-performance hot activation delayed fluorescence material is urgently developed.
The content of the invention
In view of this, it is single in order to solve hot activation delayed fluorescence material category in the prior art, it is impossible to meet OLED devices The technical problem of part demand, the present invention provides a kind of hot activation delayed fluorescence material based on phenyl indazole derivative and its organic Electroluminescent device.
Present invention firstly provides a kind of hot activation delayed fluorescence material based on phenyl indazole derivative, with such as formula (I) structural formula shown in：
Wherein, in arylamine of the Ar selected from substituted or unsubstituted C6-C60, substituted or unsubstituted C4-C60 heteroaromatic Any one.
It is preferred that, the Ar is selected from substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C4-C30 virtue Any one in heterocycle.
It is preferred that, any one of the Ar in following structure：
Wherein, R1、R2One kind in alkyl, substituted or unsubstituted C6-C30 aryl independently selected from C1-C10； R3、R4One kind in alkyl, substituted or unsubstituted C6-C30 aryl independently selected from H, C1-C10, or R3Or R4With The group formation condensed ring at place.
It is preferred that, the hot activation delayed fluorescence material based on phenyl indazole derivative, in following compound 1-10 Any one shown in：
The present invention also provides a kind of organic electroluminescence device, including anode, negative electrode and positioned at the anode and negative electrode Between several organic function layers, the organic function layer includes the hot activation based on phenyl indazole derivative and prolongs Slow fluorescent material any one or at least two combination.
It is preferred that, the organic function layer includes luminescent layer, and the luminescent layer includes described indazole-derived based on phenyl The hot activation delayed fluorescence material of thing any one or at least two combination.
It is preferred that, the hot activation delayed fluorescence material based on phenyl indazole derivative is used as the material that adulterates in luminescent layer Material, co-doped material or material of main part.
Beneficial effects of the present invention：
It is single in order to solve hot activation delayed fluorescence material category in the prior art, it is impossible to meet the skill of OLED demand Art problem, the present invention provides a kind of hot activation delayed fluorescence material and its organic electroluminescence based on phenyl indazole derivative Part.The present invention is hexa-atomic thick with arylamine or containing nitrogen-atoms using phenyl ring as connecting bridge using phenyl indazole group as electron acceptor With heteroaromatic as electron donor, make to have electrophilic and electron donating group in molecule concurrently, realize HOMO and LUMO electron cloud point From effectively induction produces Intramolecular electron transfer, is conducive to carrier to transmit in the devices, and then improves organic electroluminescent The characteristics of luminescence of device.
Test result indicates that, the hot activation delayed fluorescence material system based on phenyl indazole derivative provided using the present invention Standby organic electroluminescence device, external quantum efficiency is high, and maximum current efficiency is up to 18.63cd/A, and maximum power efficiency is reachable 20.31lm/W, with higher luminous efficiency, and driving voltage is low, is a kind of excellent OLED material.
Embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described with reference to embodiment, still It should be appreciated that these descriptions are simply to further illustrate the features and advantages of the present invention, rather than to the claims in the present invention Limitation.
It should be noted that unless otherwise prescribed, the implication of scientific and technical terminology used in the present invention and people in the art The implication that member is generally understood is identical.
Alkyl of the present invention refers to the alkyl that a hydrogen atom is minused in alkane molecule, and it can be straight chain alkane Base, branched alkyl or cycloalkyl, example may include methyl, ethyl, propyl group, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth Base, amyl group, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Arylamine of the present invention can be monocyclic diaryl-amine, polycyclic diaryl-amine or monocyclic and polycyclic diaryl-amine.
Aryl of the present invention refers on the aromatic core carbon of aromatic hydrocarbon molecule remove after a hydrogen atom, is left the total of univalent perssad Claim, it can be monocyclic aryl or fused ring aryl, example may include phenyl, xenyl, naphthyl, anthryl, phenanthryl or pyrenyl etc., but Not limited to this.
Heteroaromatic of the present invention refers to the total of the group that one or more aromatic core carbon are obtained by hetero atom replacement in aromatic ring Claim, the hetero atom includes but is not limited to oxygen, sulphur, nitrogen or silicon atom, the heteroaromatic can be monocyclic or condensed ring, and example can be wrapped Include pyridine radicals, phenothiazinyl, phenoxazine base, pyrimidine radicals, benzo pyrimidine radicals, carbazyl, triazine radical, benzothiazolyl, benzo miaow Oxazolyl, acridinyl etc., but not limited to this.
Present invention firstly provides the hot activation delayed fluorescence material based on phenyl indazole derivative, with such as formula (I) Suo Shi Structural formula：
Wherein, in arylamine of the Ar selected from substituted or unsubstituted C6-C60, substituted or unsubstituted C4-C60 heteroaromatic Any one.
According to the present invention, preferably Ar is selected from substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C4-C30 Heteroaromatic in any one.Hetero atom in the heteroaromatic is preferably one or both of N, O, S and Si；Further , the heteroaromatic is preferably hexa-atomic thick and heteroaromatic.
According to the present invention, any one of further preferably described Ar in following structure：
Wherein, R1、R2One kind in alkyl, substituted or unsubstituted C6-C30 aryl independently selected from C1-C10； R3、R4One kind in alkyl, substituted or unsubstituted C6-C30 aryl independently selected from H, C1-C10, or R3Or R4With The group formation condensed ring at place.It is preferred that, R1、R2Independently selected from methyl, ethyl, propyl group, butyl, phenyl, xenyl or three Phenyl, more preferably methyl, ethyl or phenyl；It is preferred that, R3、R4Independently selected from H, methyl, ethyl, propyl group, butyl, phenyl Or xenyl, or R3Or R4With the group at place formation condensed ring, more preferably H, methyl, ethyl or phenyl, or for phenyl with The group formation naphthalene nucleus at place.
As an example, it is not particularly limited, the hot activation delayed fluorescence material of the present invention based on phenyl indazole derivative Material is as follows：
Some for being enumerated above the hot activation delayed fluorescence material of the present invention based on phenyl indazole derivative are specific Structure type, but the invention is not limited in these listed chemical constitution, every based on structure shown in formula (I), Ar It should be all included for group as defined above.
The present invention is using phenyl indazole group as electron acceptor, using phenyl ring as connecting bridge, with arylamine or contains nitrogen-atoms Hexa-atomic thick and heteroaromatic makes to have electrophilic and electron donating group in molecule concurrently, realizes HOMO and LUMO electricity as electron donor Sub- cloud separation, effectively induction produces Intramolecular electron transfer, is conducive to carrier to transmit in the devices, and then improves Organic Electricity The characteristics of luminescence of electroluminescence device.
The preparation method of the hot activation delayed fluorescence material based on phenyl indazole derivative of the invention, can be by by formula (II) Shown compound obtains the hot activation based on phenyl indazole derivative shown in formula (I) with the compound reaction shown in formula (III) Delayed fluorescence material.
The present invention does not have particular/special requirement to the reaction condition of above-mentioned reaction, with such reaction well known to those skilled in the art Normal condition.The present invention has no particular limits to the source of the raw material employed in above-mentioned all kinds of reactions, Ke Yiwei Commercially available prod is prepared using preparation method well-known to those skilled in the art.Wherein, the selection of the Ar ibid institute State, will not be repeated here.
The present invention also provides a kind of organic electroluminescence device, and the organic electroluminescence device is those skilled in the art Known organic electroluminescence device, organic electroluminescence device of the present invention includes anode, negative electrode and is located at Several organic function layers between the anode and negative electrode, the organic function layer includes described based on phenyl indazole spreading out Biological hot activation delayed fluorescence material any one or at least two combination.The organic function layer can include hole In implanted layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer at least One layer, preferably described organic function layer includes luminescent layer, and the luminescent layer includes the heat based on phenyl indazole derivative Activate delayed fluorescence material any one or at least two combination.The more preferably described heat shock based on phenyl indazole derivative Delayed fluorescence material living is used as dopant material, co-doped material or material of main part in luminescent layer.
The substrate in traditional organic electroluminescence device, example can be used in substrate in organic electroluminescence device of the present invention Such as glass or plastics, it is preferred that use glass substrate in the present invention.
The electrode material with big work function can be used in anode material, can be such as indium oxide, zinc oxide, tin indium oxide (ITO), metal oxide of indium zinc oxide (IZO) or its mixture etc..Preferably, tin indium oxide is used in the present invention (ITO) as anode material.
Hole transmission layer can use various tri-arylamine group materials.Preferably, NPB is used in the present invention.
Cathode material can be used with low work function electrode material, can use metal or its mixture structure, such as Mg, Ag, Ca or electron injecting layer/metal-layer structure, such as LiF/Al, Li2The common cathode structure such as O/Al.Preferably, originally The electron injection material used in invention is LiF, and negative electrode is Al.
The present invention has no particular limits to the source of the raw material employed in following examples, can for commercially available prod or Prepared using preparation method well-known to those skilled in the art.
Embodiment 1：The synthesis of compound 1
First, by 1- phenyl -3- (tri-tert stannane base) -1- indazoles (0.021mol, 10g), 10- (4- bromobenzenes) -9, 9- dimethyl acridiniums (0.021mol, 7.50g) are placed in round-bottomed flask, add 1g lithium chlorides, add 20mL toluene, 0.5g triphens Base palladium bichloride, under nitrogen protection, after flowing back 48 hours, stops reaction, suction filtration obtains yellow solid.Product is dried by extraction Afterwards, purified with column chromatography, obtain 5.01g products.Yield：49.9%.
Mass spectrum m/z：477.25 (calculated values：477.22).Theoretical elemental content (%) C34H27N3：C, 85.50；H, 5.70； N, 8.80；Survey constituent content (%)：C, 85.58；H, 5.75；N, 8.86.
Embodiment 2：The synthesis of compound 3
The step of synthesis step be the same as Example 1, simply by a kind of raw material 10- (4- bromobenzenes) -9,9- dimethyl a word used for translations therein 10- (4- bromobenzenes) -10H- phenthazine is changed into pyridine.
Mass spectrum m/z：467.21 (calculated values：467.15).Theoretical elemental content (%) C31H21N3S：C, 79.63；H, 4.53； N, 8.99；S, 6.86 actual measurement constituent contents (%)：C, 79.67；H, 4.52；N, 8.98；S, 6.90.
Embodiment 3：The synthesis of compound 4
The step of synthesis step be the same as Example 1, simply by a kind of raw material 10- (4- bromobenzenes) -9,9- dimethyl a word used for translations therein 10- (4- bromobenzenes) -10H- phenoxazines are changed into pyridine.
Mass spectrum m/z：451.22 (calculated values：451.17).Theoretical elemental content (%) C31H21N3O：C, 82.46；H, 4.69； N, 9.31；O, 3.54 actual measurement constituent contents (%)：C, 82.50；H, 4.69；N, 9.33；O, 3.57.
Embodiment 4：The synthesis of compound 5
The step of synthesis step be the same as Example 1, simply by a kind of raw material 10- (4- bromobenzenes) -9,9- dimethyl a word used for translations therein N- (4- bromobenzenes)-N- phenyl napthyl -1- amine is changed into pyridine.
Mass spectrum m/z：487.32 (calculated values：487.20).Theoretical elemental content (%) C35H25N3：C, 86.21；H, 5.17； N, 8.62；Survey constituent content (%)：C, 86.29；H, 5.15；N, 8.68.
Embodiment 5：The synthesis of compound 6
The step of synthesis step be the same as Example 1, simply by a kind of raw material 10- (4- bromobenzenes) -9,9- dimethyl a word used for translations therein The bromo- N of 4-, N- diphenyl aniline are changed into pyridine.
Mass spectrum m/z：437.28 (calculated values：437.19).Theoretical elemental content (%) C31H23N3：C, 85.10；H, 5.30； N, 9.60；Survey constituent content (%)：C, 85.19；H, 5.33；N, 9.65.
Embodiment 6：The preparation of organic electroluminescence device
The glass substrate of ito transparent electrode will be coated with ultrasonically treated in commercial detergent, rinsed in deionized water, In acetone：Ultrasonic oil removing in alcohol mixed solvent, is baked in clean environment and removes moisture completely, clear with ultraviolet light and ozone Wash.
The above-mentioned glass substrate for being coated with ito transparent electrode is placed in vacuum chamber, 10 are evacuated to-5–10-3Pa, evaporation Hole transmission layer NPB, evaporation rate is 0.1nm/s, and thickness is 20nm.On hole transmission layer be deposited the present invention in based on benzene The hot activation delayed fluorescence material of base indazole derivative is as luminescent layer, and evaporation rate is 0.1nm/s, and thickness is 30nm.In hair One layer of AlQ of vacuum evaporation on photosphere3As electron transfer layer, evaporation rate is 0.1nm/s, and thickness is 20nm.In electric transmission LiF and Al is deposited on layer as the electron injecting layer and negative electrode of device, thickness difference 1nm and 100nm.The photism of measurement device Can, it the results are shown in Table 1.
The characteristics of luminescence of luminescent device prepared by the embodiment of the present invention of table 1
As can be seen that prepared by the hot activation delayed fluorescence material based on phenyl indazole derivative provided using the present invention Organic electroluminescence device, external quantum efficiency is high, and maximum current efficiency is up to 18.63cd/A, and maximum power efficiency is reachable 20.31lm/W, with higher luminous efficiency, and driving voltage is low, is a kind of excellent OLED material.
Obviously, the explanation of above example is only intended to the method and its core concept for helping to understand the present invention.It should refer to Go out, under the premise without departing from the principles of the invention, can also be to this hair for the those of ordinary skill of the technical field Bright to carry out some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.

Claims (7)

1. the hot activation delayed fluorescence material based on phenyl indazole derivative, with the structural formula as shown in formula (I)：
Wherein, appointing in arylamine of the Ar selected from substituted or unsubstituted C6-C60, substituted or unsubstituted C4-C60 heteroaromatic Meaning is a kind of.
2. the hot activation delayed fluorescence material according to claim 1 based on phenyl indazole derivative, it is characterised in that Ar Arylamine selected from substituted or unsubstituted C6-C30, any one in substituted or unsubstituted C4-C30 heteroaromatic.
3. the hot activation delayed fluorescence material according to claim 1 based on phenyl indazole derivative, it is characterised in that Ar Any one in following structure：
Wherein, R1、R2One kind in alkyl, substituted or unsubstituted C6-C30 aryl independently selected from C1-C10；R3、R4Solely The on the spot alkyl selected from H, C1-C10, one kind in substituted or unsubstituted C6-C30 aryl, or R3Or R4With the base at place Group forms condensed ring.
4. the hot activation delayed fluorescence material according to claim 1 based on phenyl indazole derivative, it is characterised in that such as Shown in any one in lower compound 1-10：
5. a kind of organic electroluminescence device, including anode, negative electrode and several between the anode and negative electrode have Machine functional layer, it is characterised in that the organic function layer include described in any one of Claims 1 to 4 based on phenyl indazole The hot activation delayed fluorescence material of derivative any one or at least two combination.
6. a kind of organic electroluminescence device according to claim 5, it is characterised in that the organic function layer includes hair Photosphere, the luminescent layer includes the hot activation delayed fluorescence based on phenyl indazole derivative described in any one of Claims 1 to 4 Material any one or at least two combination.
7. a kind of organic electroluminescence device according to claim 6, it is characterised in that described indazole-derived based on phenyl The hot activation delayed fluorescence material of thing is used as dopant material, co-doped material or material of main part in luminescent layer.
CN201710666338.4A 2017-08-07 2017-08-07 Hot activation delayed fluorescence material and its organic electroluminescence device based on phenyl indazole derivative Withdrawn CN107311979A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108516975A (en) * 2018-04-02 2018-09-11 长春海谱润斯科技有限公司 A kind of hot activation delayed fluorescence material and its organic electroluminescence device
CN110452237A (en) * 2018-05-07 2019-11-15 武汉尚赛光电科技有限公司 A kind of thermotropic delayed fluorescence material and its preparation method and application
US11312710B2 (en) 2018-07-27 2022-04-26 Shanghai Tianma AM-OLED Co., Ltd. Compound and organic light-emitting display device

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030207927A1 (en) * 2001-12-13 2003-11-06 Wyeth Phenyl benzisoxazoles as estrogenic agents
US20100237769A1 (en) * 2007-12-21 2010-09-23 Park Kyung-Ho Charge transport materials for luminescent applications
CN105294670A (en) * 2015-11-20 2016-02-03 上海天马有机发光显示技术有限公司 Organic electroluminescent compound and organic photoelectric apparatus thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030207927A1 (en) * 2001-12-13 2003-11-06 Wyeth Phenyl benzisoxazoles as estrogenic agents
US20100237769A1 (en) * 2007-12-21 2010-09-23 Park Kyung-Ho Charge transport materials for luminescent applications
CN105294670A (en) * 2015-11-20 2016-02-03 上海天马有机发光显示技术有限公司 Organic electroluminescent compound and organic photoelectric apparatus thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108516975A (en) * 2018-04-02 2018-09-11 长春海谱润斯科技有限公司 A kind of hot activation delayed fluorescence material and its organic electroluminescence device
CN110452237A (en) * 2018-05-07 2019-11-15 武汉尚赛光电科技有限公司 A kind of thermotropic delayed fluorescence material and its preparation method and application
CN110452237B (en) * 2018-05-07 2021-02-09 武汉尚赛光电科技有限公司 Thermally induced delayed fluorescent material and preparation method and application thereof
US11312710B2 (en) 2018-07-27 2022-04-26 Shanghai Tianma AM-OLED Co., Ltd. Compound and organic light-emitting display device

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Application publication date: 20171103