CN107698568A - The hot activation delayed fluorescence material and its organic electroluminescence device of a kind of pyrimidine derivatives - Google Patents

The hot activation delayed fluorescence material and its organic electroluminescence device of a kind of pyrimidine derivatives Download PDF

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CN107698568A
CN107698568A CN201710877704.0A CN201710877704A CN107698568A CN 107698568 A CN107698568 A CN 107698568A CN 201710877704 A CN201710877704 A CN 201710877704A CN 107698568 A CN107698568 A CN 107698568A
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delayed fluorescence
pyrimidine derivatives
organic electroluminescence
activation delayed
hot activation
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蔡辉
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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 the hot activation delayed fluorescence material and its organic electroluminescence device of pyrimidine derivatives, belongs to technical field of organic electroluminescence.The present invention is to join pyrimidine group as electron acceptor, electron donor is used as using arylamine or the hexa-atomic thick heteroaryl for containing nitrogen-atoms, make to have electrophilic and electron donating group in molecule concurrently, realize HOMO and LUMO electron cloud separation, effectively induction produces Intramolecular electron transfer, be advantageous to carrier to transmit in the devices, and then improve the characteristics of luminescence of organic electroluminescence device.The organic electroluminescence device prepared using the hot activation delayed fluorescence material of pyrimidine derivatives provided by the invention, external quantum efficiency is high, and luminous efficiency is high, and driving voltage is low, is a kind of excellent OLED material.

Description

The hot activation delayed fluorescence material and its organic electroluminescent of a kind of pyrimidine derivatives Device
Technical field
The present invention relates to technical field of organic electroluminescence, and in particular to a kind of hot activation delay of pyrimidine derivatives is glimmering Luminescent material and its organic electroluminescence device.
Background technology
Organic electroluminescent LED (Organic Light-Emitting Diode, OLED) refers to luminous organic material The diode to be 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.
Certainly, the behind that OLED technology is advanced by leaps and bounds, luminous organic material play 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.Although fluorescent material OLED can with higher By property and stability, but relatively low external quantum efficiency still limits its application.And phosphor material generally comprises rare precious metals, Cause it is expensive, and device stability can poor, device efficiency decline the problems such as serious and all largely further limit Its extensive commercial popularization is made.In recent years, hot activation delayed fluorescence material has been increasingly becoming the new focus of this area research.Should Material can realize 100% internal quantum efficiency under conditions of non precious metal, can not only avoid making for expensive heavy metal With so as to reduce cost to a certain extent, and it can be desirable to greatly improve device lifetime and spectrum stability, while there is hair Light efficiency is high, the advantage such as environment-friendly, is referred to as third generation electroluminescent material.
But the correlative study at present on hot activation delayed fluorescence material is also fewer, 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, hot activation delayed fluorescence material category is single in order to solve in the prior art, can not meet OLED devices The technical problem of part demand, the present invention provide the hot activation delayed fluorescence material and its organic electroluminescence hair of a kind of pyrimidine derivatives Optical device.
Present invention firstly provides a kind of hot activation delayed fluorescence material of pyrimidine derivatives, has as shown in formula (I) Structural formula：
Wherein, Ar is selected from substituted or unsubstituted C12-C60 arylamine, substituted or unsubstituted C12-C60 heteroaryl In any one.
Preferably, the Ar is selected from substituted or unsubstituted C12-C30 arylamine, substituted or unsubstituted C12-C30 Any one in heteroaryl.
Preferably, any one of the Ar in following structure：
Wherein, R1-R7Alkyl independently selected from C1-C10, one kind in substituted or unsubstituted C6-C30 aryl.
Preferably, the hot activation delayed fluorescence material of described a kind of pyrimidine derivatives, it is any one in following structure Shown in kind：
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 delayed fluorescence of described connection pyrimidine derivatives Material any one or at least two combination.
Preferably, the organic function layer includes luminescent layer, and the luminescent layer includes the heat of described connection pyrimidine derivatives Activate delayed fluorescence material any one or at least two combination.
Preferably, the hot activation delayed fluorescence material of the pyrimidine derivatives is used as material of main part in luminescent layer.
Beneficial effects of the present invention：
Hot activation delayed fluorescence material category is single in order to solve in the prior art, can not meet the skill of OLED demand Art problem, the present invention provide a kind of the hot activation delayed fluorescence material and its organic electroluminescence device of pyrimidine derivatives.This Invention, using arylamine or the hexa-atomic thick heteroaryl for containing nitrogen-atoms as electron donor, makes to join pyrimidine group as electron acceptor Have electrophilic and electron donating group in molecule concurrently, realize HOMO and LUMO electron cloud separation, effectively induction produces intramolecular Electric charge transfer, be advantageous to carrier and transmit in the devices, and then improve the characteristics of luminescence of organic electroluminescence device.Use this hair Organic electroluminescence device prepared by the hot activation delayed fluorescence material of the connection pyrimidine derivatives of bright offer, external quantum efficiency is high, 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 further explanation 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 minus the alkyl that a hydrogen atom forms 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 to after removing a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule, is left the total of univalent perssad Claiming, it can be monocyclic aryl or fused ring aryl, and example may include phenyl, xenyl, naphthyl, anthryl, phenanthryl or pyrenyl etc., but Not limited to this.
Hetero-aromatic ring of the present invention refers to the total of the group that one or more aromatic core carbon substitute to obtain by hetero atom in aromatic ring Claim, the hetero atom includes but is not limited to oxygen, sulphur, nitrogen or silicon atom, and the heteroaromatic can be monocyclic or condensed ring, and example can wrap 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 a kind of hot activation delayed fluorescence material of pyrimidine derivatives, has as shown in formula (I) Structural formula：
Wherein, Ar is selected from substituted or unsubstituted C12-C60 arylamine, substituted or unsubstituted C12-C60 heteroaryl In any one.
According to the present invention, preferably Ar is selected from substituted or unsubstituted C12-C30 arylamine, substituted or unsubstituted C12- Any one in C30 heteroaryl.Hetero atom in the hetero-aromatic ring is preferably one or both of N, O, S and Si；Enter One step, the hetero-aromatic ring is preferably hexa-atomic thick heteroaryl.
According to the present invention, any one of further preferably described Ar in following structure：
Wherein, R1-R7Alkyl independently selected from C1-C10, one kind in substituted or unsubstituted C6-C30 aryl.
As an example, it is not particularly limited, a kind of hot activation delayed fluorescence material of pyrimidine derivatives of the present invention It is as follows：
It is enumerated above some specific structures of the hot activation delayed fluorescence material of pyrimidine derivatives of the present invention Form, but the invention is not limited in these listed chemical constitution, every based on structure shown in formula (I), Ar is as above The group limited should be all included.
The present invention is used as electricity to join pyrimidine group as electron acceptor using arylamine or the hexa-atomic thick heteroaryl for containing nitrogen-atoms Sub- donor, make to have electrophilic and electron donating group in molecule concurrently, realize HOMO and LUMO electron cloud separation, effectively induction production Raw Intramolecular electron transfer, is advantageous to carrier and transmits in the devices, and then improves the characteristics of luminescence of organic electroluminescence device.
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 include anode, negative electrode and are located at Several organic function layers between the anode and negative electrode, the organic function layer include described connection pyrimidine derivatives Hot activation delayed fluorescence material any one or at least two combination.The organic function layer can include hole and inject At least one in layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer Layer, preferably described organic function layer include luminescent layer, and the luminescent layer includes the hot activation delay of described connection pyrimidine derivatives Fluorescent material any one or at least two combination.The hot activation delayed fluorescence material of more preferably described pyrimidine derivatives It is used as 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) it is used 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, metal or its mixture structure can be used, 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 be commercially available prod or It is prepared using preparation method well-known to those skilled in the art.
Embodiment 1：The synthesis of compound 1
By 5,5- dibromos connection pyrimidine (16mmol, 5g), carbazole (16mmol, 2.67g) is placed in round-bottomed flask, then successively Add 50mL toluene, iodate Asia ketone (1.6mmol, 0.3g), potassium phosphate (48mmol, 10.2), trans 1,2- cyclohexanediamine (1.6mmol, 0.18g), is passed through nitrogen protection, and reaction overnight, stops reaction afterwards.Product is by extraction, after drying, with post layer Analysis method is purified, and obtains 5.02g products.Yield：55.3%.
Mass spectrum m/z：488.51 (calculated values：488.54).Theoretical elemental content (%) C32H20N6：C, 78.67；H, 4.13； N, 17.20；Survey constituent content (%)：C, 78.65；H, 4.13；N, 17.22.
Embodiment 2：The synthesis of compound 2
The step of synthesis step is with embodiment 1, a kind of raw material carbazole therein is simply changed to equimolar phenoxazine.Matter Compose m/z：520.57 (calculated values：520.54).Theoretical elemental content (%) C32H20N6O2：C, 73.84；H, 3.87；N, 16.14； O, 6.15 actual measurement constituent contents (%)：C, 73.84；H, 3.87；N, 16.14；O, 6.15.
Embodiment 3：The synthesis of compound 3
The step of synthesis step is with embodiment 1, a kind of raw material carbazole therein is simply changed to equimolar phenthazine.Matter Compose m/z：552.69 (calculated values：552.67).Theoretical elemental content (%) C32H20N6S2：C, 69.54；H, 3.65；N, 15.21； S, 11.60 actual measurement constituent contents (%)：C, 69.54；H, 3.63；N, 15.21；S, 11.62
Embodiment 4：The synthesis of compound 4
The step of synthesis step is with embodiment 1, a kind of raw material carbazole therein is simply changed to equimolar 9,10- bis- Hydrogen -9,9-dimethylacridan.Mass spectrum m/z：572.62 (calculated values：572.70).Theoretical elemental content (%) C38H32N6：C, 79.69；H, 5.63；N, 14.67；Survey constituent content (%)：C, 79.69；H, 5.63；N, 14.67.
Embodiment 5：The synthesis of compound 6
The step of synthesis step is with embodiment 1, a kind of raw material carbazole therein is simply changed to equimolar 10,10- bis- Methyl -5,10- dihydrobenzo silane.Mass spectrum m/z：604.88 (calculated values：604.85).Theoretical elemental content (%) C36H32N6Si2：C, 71.49；H, 5.33；N, 13.89；Si, 9.29；Survey constituent content (%)：C, 71.47；H, 5.36；N, 13.88；Si, 9.29.
Embodiment 6：The synthesis of compound 9
By tri-butyl phosphine (4.4mL 1.0M toluene solution, 1.48g, 0.05mmol), palladium (0.4g, 1.83mmol) and sodium tert-butoxide (22.8g, 238mmol) is added to aniline (17.0g, 183mmol) and the bromo- 9- phenyl -9H- of 3- Solution of the carbazole (58.9g, 183mmol) in degassed toluene (500mL), and the mixture is heated 2 hours under reflux. The reactant mixture is cooled to room temperature, filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and uses first Benzene is extracted, and merges organic phase, and it is evaporated under vacuo.The residue is filtered via silica gel, knot of laying equal stress on It is brilliant.Obtain 48.8g intermediate As.Yield：80%.
By 5,5- dibromos connection pyrimidine (16mmol, 5g), intermediate A (16mmol, 5.3g) is placed in round-bottomed flask, Ran Houyi Secondary addition 50mL toluene, iodate Asia ketone (1.6mmol, 0.3g), potassium phosphate (48mmol, 10.2), trans 1,2- cyclohexanediamine (1.6mmol, 0.18g), is passed through nitrogen protection, and reaction overnight, stops reaction afterwards.Product is by extraction, after drying, with post layer Analysis method is purified, and obtains 5.02g products.Yield：50.3%.Mass spectrum m/z：822.99 (calculated values：822.95).Theoretical elemental Content (%) C56H38N8：C, 81.73；H, 4.65；N, 13.62；Survey constituent content (%)：C, 81.72；H, 4.66；N, 13.62。
Embodiment 7：The synthesis of compound 10
The step of synthesis step is with embodiment 6, simply a kind of bromo- 9- phenyl -9H- carbazoles of raw material 3- therein are changed to Mole the bromo- 9,9- dimethyl fluorenes of 3-.Mass spectrum m/z：724.88 (calculated values：724.89).Theoretical elemental content (%) C50H40N6： C, 82.84；H, 5.56；N, 11.59；Survey constituent content (%)：C, 82.84；H, 5.58；N, 11.58.
Embodiment 8：The synthesis of compound 10
The step of synthesis step is with embodiment 1, a kind of raw material carbazole therein is simply changed to equimolar diphenylamines.Matter Compose m/z：492.50 (calculated values：492.57).Theoretical elemental content (%) C32H24N6：C, 78.03；H, 4.91；N, 17.06；It is real Survey constituent content (%)：78.04；H, 4.92；N, 17.04.
Embodiment 9：The preparation of 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 is washed Wash 30 minutes, cleaned repeatedly with distilled water 2 times, ultrasonic washing 10 minutes, after distilled water cleaning terminates, isopropanol, acetone, first Alcohol equal solvent in order dry later by ultrasonic washing, is transferred in plasma washing machine, aforesaid substrate is washed 5 minutes, It is sent in evaporator.
The above-mentioned glass substrate for being coated with ito transparent electrode is placed in vacuum chamber, is evacuated to 10-5–10-3Pa, evaporation Hole transmission layer NPB, evaporation rate 0.1nm/s, thickness 20nm.The connection pyrimidine in the present invention is deposited on hole transmission layer The hot activation delayed fluorescence material of derivative is as luminescent layer, evaporation rate 0.1nm/s, thickness 30nm.On luminescent layer One layer of AlQ of vacuum evaporation3As electron transfer layer, evaporation rate 0.1nm/s, thickness 20nm.Steam on the electron transport layer Plate electron injecting layers and negative electrode of the LiF and Al as device, thickness difference 1nm and 100nm.The luminescent properties of measurement device, knot Fruit is 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 the Organic Electricity prepared using the hot activation delayed fluorescence material of pyrimidine derivatives provided by the invention Electroluminescence device, external quantum efficiency is high, and low with higher luminous efficiency, driving voltage, is a kind of excellent OLED materials Material.
Obviously, the explanation of above example is only intended to help the method and its core concept for understanding 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. a kind of hot activation delayed fluorescence material of pyrimidine derivatives, there is the structural formula as shown in formula (I)：
Wherein, in arylamine of the Ar selected from substituted or unsubstituted C12-C60, substituted or unsubstituted C12-C60 heteroaryl Any one.
2. the hot activation delayed fluorescence material of a kind of pyrimidine derivatives according to claim 1, it is characterised in that Ar is selected Arylamine from substituted or unsubstituted C12-C30, any one in substituted or unsubstituted C12-C30 heteroaryl.
3. the hot activation delayed fluorescence material of a kind of pyrimidine derivatives according to claim 1, it is characterised in that Ar is selected From any one in following structure：
Wherein, R1-R7Alkyl independently selected from C1-C10, one kind in substituted or unsubstituted C6-C30 aryl.
4. the hot activation delayed fluorescence material of a kind of pyrimidine derivatives according to claim 1, it is characterised in that described Any one of derivative in following structure：
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 includes the connection pyrimidine derivatives described in any one of Claims 1 to 4 Hot activation delayed fluorescence material 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 include the hot activation delayed fluorescence material of the connection pyrimidine derivatives described in any one of Claims 1 to 4 Any one or at least two combination.
A kind of 7. organic electroluminescence device according to claim 6, it is characterised in that the heat of the pyrimidine derivatives Activation delayed fluorescence material is used as material of main part in luminescent layer.
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CN108219781A (en) * 2018-04-02 2018-06-29 长春海谱润斯科技有限公司 The hot activation delayed fluorescence material and its organic electroluminescence device of a kind of tetrazine derivatives
WO2020015245A1 (en) * 2018-07-18 2020-01-23 武汉华星光电半导体显示技术有限公司 Thermally-activated delayed fluorescence material and synthesis method therefor

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CN103261172A (en) * 2010-12-21 2013-08-21 E.I.内穆尔杜邦公司 Electronic device including a pyrimidine compound
CN106916170A (en) * 2015-12-28 2017-07-04 上海大学 A kind of carboline disubstituted derivatives and its preparation method and application

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US20110309340A1 (en) * 2008-09-26 2011-12-22 Osram Opto Semiconductors Gmbh Organic Electronic Component and Method for the Production Thereof
CN103261172A (en) * 2010-12-21 2013-08-21 E.I.内穆尔杜邦公司 Electronic device including a pyrimidine compound
CN106916170A (en) * 2015-12-28 2017-07-04 上海大学 A kind of carboline disubstituted derivatives and its preparation method and application

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CN108219781A (en) * 2018-04-02 2018-06-29 长春海谱润斯科技有限公司 The hot activation delayed fluorescence material and its organic electroluminescence device of a kind of tetrazine derivatives
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