CN111848617A - Organic electroluminescent material and application thereof - Google Patents

Organic electroluminescent material and application thereof Download PDF

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CN111848617A
CN111848617A CN201910339403.1A CN201910339403A CN111848617A CN 111848617 A CN111848617 A CN 111848617A CN 201910339403 A CN201910339403 A CN 201910339403A CN 111848617 A CN111848617 A CN 111848617A
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organic electroluminescent
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CN111848617B (en
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王湘成
陈文勇
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Shanghai Yaoyi Electronic Technology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract

The organic electroluminescent material has higher electron transport capacity, can be applied to an organic electroluminescent device as an electron transport layer, can reduce the driving voltage of the device, improve the luminous efficiency of the device, prolong the service life of the device and further expand the application range of the device.

Description

Organic electroluminescent material and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescence, and relates to an organic electroluminescent material and application thereof.
Background
Compared with the conventional liquid crystal technology, the organic electroluminescence (OLED) technology does not need backlight irradiation and a color filter, a pixel can emit light to be displayed on a color display panel, and a series of advantages of self-luminescence, wide viewing angle, almost infinite contrast, low power consumption, extremely high reaction speed, rich colors and the like are brought into great interest.
The improvement of the performance of OLED devices has become a hot spot of current research, mainly including: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only the structure and the manufacturing process of the OLED device need to be innovated, but also the photoelectric functional material of the OLED device needs to be continuously researched and innovated.
The photoelectric functional materials of the OLED can be divided into two categories from the application, namely charge injection transport materials and luminescent materials, and further, the charge injection transport materials can be divided into electron injection transport materials and hole injection transport materials, and the luminescent materials can be divided into main luminescent materials and doping materials.
At present, the driving voltage of the electron injection transmission material is higher, the electron transmission performance is lower, and the development of an OLED device is limited, so that the development of the high-efficiency electron transmission material is limited, the driving voltage of the OLED device is reduced, the luminous efficiency of the OLED device is improved, the service life of the OLED device is prolonged, and the organic light-emitting diode has important practical application value.
Disclosure of Invention
In view of the above-mentioned shortcomings of the prior art, the present invention is directed to a novel organic electroluminescent material, so as to reduce the driving voltage of the device, improve the light-emitting efficiency of the device, prolong the lifetime of the device, and thus expand the application range of the device.
In order to achieve the above object, the present invention provides an organic electroluminescent material, wherein the organic electroluminescent material has a structural formula as follows:
Figure BDA0002040236240000011
wherein L comprises a single bond, a substituted or unsubstituted aryl group with a ring forming carbon number of 6-30, a substituted or unsubstituted heteroaryl group with a ring forming carbon number of 5-30, a substituted or unsubstituted alkyl group with a carbon number of 1-30, a substituted or unsubstituted fluoroalkyl group with a carbon number of 1-30, a substituted or unsubstituted cycloalkyl group with a ring forming carbon number of 3-30, and a substituted or unsubstituted aralkyl group with a carbon number of 7-30; r 1、R2Comprises the same or different, and respectively comprises a single bond, a substituted or unsubstituted aryl group with the carbon number of 6-30 formed by a ring, a substituted or unsubstituted heteroaryl group with the carbon number of 5-30 formed by a ring, a substituted or unsubstituted alkyl group with the carbon number of 1-30, and a substituted or unsubstituted fluoroalkane with the carbon number of 1-30The group, the substituted or unsubstituted ring forms a cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a substituted germanium group, a cyano group, a nitro group or a carboxyl group.
Optionally, the organic electroluminescent material is selected from any one of the following compounds:
Figure BDA0002040236240000021
Figure BDA0002040236240000031
Figure BDA0002040236240000041
the invention also provides the application of the organic electroluminescent material in an organic electroluminescent device; the organic electroluminescent material is used as an electron transport layer in the organic electroluminescent device.
The invention also provides an organic electroluminescent device which comprises an anode, a cathode and an organic layer positioned between the anode and the cathode, wherein the organic layer comprises an electron transport layer, and the electron transport layer comprises any one of the organic electroluminescent materials.
Optionally, the electron transport layer further comprises a metal material, wherein the metal comprises one or a combination of alkali metal, alkaline earth metal and rare earth metal; the metal comprises one or a combination of ytterbium metal, samarium metal, europium metal and dysprosium metal.
Optionally, the electron transport layer further comprises a metal compound, wherein the metal compound comprises one or a combination of an alkali metal compound, an alkaline earth metal compound and a rare earth metal compound; the metal compound comprises one or a combination of 8-hydroxyquinoline lithium and lithium fluoride.
Optionally, in the electron transport layer, the range of the mass percentage of the organic electroluminescent material includes 80% to 99%.
Optionally, the organic electroluminescent device comprises one or a combination of a top-emitting device and a bottom-emitting device, wherein the top-emitting device further comprises an optical coupling layer.
The invention also provides a display device which comprises the organic electroluminescent device.
The invention also provides electronic equipment which comprises the organic electroluminescent device.
As described above, the organic electroluminescent material provided by the invention has higher electron transport capacity, can be applied to an organic electroluminescent device as an electron transport layer, reduces the driving voltage of the device, improves the luminous efficiency of the device, prolongs the service life of the device, and thus enlarges the application range of the device.
Drawings
Fig. 1 is a schematic structural view of a bottom emission device in the present invention.
Fig. 2 is a schematic structural view of another bottom emission device in the present invention.
Description of the element reference numerals
101. 201 anode
112. 212 hole injection layer
122. 222 hole transport layer
132. 232 blue hole transport layer
142. 242 blue light emitting layer
152. 252 hole blocking layer
162. 262 electron transport layer
103. 203 cathode
Detailed Description
The embodiments of the present invention are described below with reference to specific embodiments, and other advantages and effects of the present invention will be easily understood by those skilled in the art from the disclosure of the present specification. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
Please refer to fig. 1-2. It should be noted that the drawings provided in the present embodiment are only for illustrating the basic idea of the present invention, and the components related to the present invention are only shown in the drawings rather than drawn according to the number, shape and size of the components in actual implementation, and the type, quantity and proportion of the components in actual implementation may be changed freely, and the layout of the components may be more complicated.
The invention provides an organic electroluminescent material, which has the following structural general formula:
Figure BDA0002040236240000051
wherein L comprises a single bond, a substituted or unsubstituted aryl group with a ring forming carbon number of 6-30, a substituted or unsubstituted heteroaryl group with a ring forming carbon number of 5-30, a substituted or unsubstituted alkyl group with a carbon number of 1-30, a substituted or unsubstituted fluoroalkyl group with a carbon number of 1-30, a substituted or unsubstituted cycloalkyl group with a ring forming carbon number of 3-30, and a substituted or unsubstituted aralkyl group with a carbon number of 7-30; r1、R2The organic silicon-organic composite material comprises the same or different single bonds, and each single bond, substituted or unsubstituted aryl with 6-30 carbon atoms in a ring form, substituted or unsubstituted heteroaryl with 5-30 carbon atoms in a ring form, substituted or unsubstituted alkyl with 1-30 carbon atoms, substituted or unsubstituted fluoroalkyl with 1-30 carbon atoms, substituted or unsubstituted cycloalkyl with 3-30 carbon atoms in a ring form, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted phosphoryl, substituted silyl, substituted germanium groups, cyano groups, nitro groups or carboxyl groups.
Specifically, the organic electroluminescent material has higher electron transmission capability, can be applied to the field of organic electroluminescence, and can be used as an electron transmission material, so that the driving voltage of an OLED device can be reduced, the luminous efficiency of the OLED device can be improved, the service life of the OLED device can be prolonged, the performance of the OLED device can be improved, and the application range of the OLED device can be enlarged.
As a further example of this embodiment, the organic electroluminescent material may be selected from any one of the following compounds:
Figure BDA0002040236240000061
Figure BDA0002040236240000071
Figure BDA0002040236240000081
specifically, the following provides specific synthetic examples of the present invention:
Figure BDA0002040236240000082
(Synthesis of Compound 1):
the synthetic route is as follows:
Figure BDA0002040236240000083
adding compound 1-1(3.16g, 10.0mmol), compound 1-2(2.02g, 10.0mmol), potassium carbonate (2.07g, 15.0mmol), bis-triphenylphosphine nickel chloride (0.13g, 0.2mmol) and 50ml of N, N-dimethylformamide into a clean three-neck flask, replacing with nitrogen three times, heating at 50 ℃ under the protection of nitrogen, stirring for 12h, after reaction, suction filtering, extracting filtrate with dichloromethane water, combining organic phases, drying, spin drying, and purifying by column to obtain compound 1(3.61g, yield 875.0%). See MS (70eV, EI +): m/z: 482.14.1HNMR(CDCl3，400Hz):8.6-8.8(t，2H)，8.4-8.5(m，2H)，8.1-8.2(m，2H)，7.8-7.9(m，2H)，7.6-7.7(m，4H)，7.4-7.5(m，8H)。
According to the technical scheme, the following compounds can be synthesized only by simply replacing corresponding raw materials:
Figure BDA0002040236240000091
Figure BDA0002040236240000101
as a further example of this embodiment, the organic electroluminescent material may be applied in an organic electroluminescent device, wherein the organic electroluminescent material is preferably used as an electron transport layer in the organic electroluminescent device.
Specifically, the organic electroluminescent material has high electron transport capacity, and can be used as an electron transport layer to reduce the driving voltage of an OLED device, improve the luminous efficiency of the OLED device and prolong the service life of the OLED device.
The invention also provides an organic electroluminescent (OLED) device comprising an anode, a cathode and an organic layer between the anode and the cathode, wherein the organic layer comprises an electron transport layer comprising the organic electroluminescent material.
Specifically, the organic electroluminescent device may include one or a combination of a single color device and a multi-color device, and the present invention is illustrated as a blue color device, but is not limited thereto. The organic electroluminescent material has higher electron transmission capability, and can be used as an electron transmission layer to reduce the driving voltage of an OLED device, improve the luminous efficiency of the OLED device and prolong the service life of the OLED device, so that the performance of the OLED device can be improved, and the application range of the OLED device can be enlarged. The anode may include at least one of indium tin oxide, zinc tin oxide, gold, silver, or copper, and the cathode may include at least one of lithium, magnesium, silver, calcium, strontium, aluminum, indium, copper, gold, and silver. The organic layer comprises a hole transport composite layer, a light emitting layer and an electron transport composite layer, wherein the electron transport composite layer at least comprises the electron transport layer containing the organic electroluminescent material, and the electron transport composite layer can also comprise one or a combination of an electron injection layer and a hole blocking layer; the hole transport composite layer at least comprises a hole transport layer, and can also comprise one or a combination of a hole injection layer and an electron blocking layer.
As a further embodiment of this embodiment, the electron transport layer further comprises a metal material, the metal comprising one or a combination of alkali metals, alkaline earth metals, and rare earth metals; the metal comprises one or a combination of ytterbium metal, samarium metal, europium metal and dysprosium metal.
Specifically, the electron transport layer is prepared by mixing the organic electroluminescent material and a metal material, and the mass percentage of the organic electroluminescent material is 80-99%, preferably 90-99%. Wherein the metal comprises one or a combination of alkali metal, alkaline earth metal and rare earth metal; the metal comprises one or a combination of ytterbium (Yb) metal, samarium (Sm) metal, europium (Eu) metal and dysprosium (Dy) metal.
As a further embodiment of this embodiment, the electron transport layer further comprises a metal compound including one or a combination of an alkali metal compound, an alkaline earth metal compound, and a rare earth metal compound; the metal compound comprises one or a combination of 8-hydroxyquinoline lithium and lithium fluoride, wherein the mass percentage of the organic electroluminescent material is 80-99%, and preferably 90-99%.
As a further embodiment of this embodiment, the organic electroluminescent device comprises one or a combination of a top-emitting device and a bottom-emitting device, wherein the top-emitting device may further comprise an optical coupling layer.
As a further example of this embodiment, the organic electroluminescent device may be applied to the preparation of a display device or an electronic apparatus.
Specifically, the organic electroluminescent material may be applied to the organic electroluminescent device as the electron transport layer to prepare the display device including the OLED display panel, and the electronic device may include a mobile phone, a computer, a television, a smart garment, a smart home device, and the like, which is not limited herein.
As shown in fig. 1, the present invention provides a bottom emission device, which sequentially comprises, from bottom to top: the anode 101, ITO (15 nm)/hole injection layer 112, HI (10nm) material is a mixed material of HT (structural formula shown below) and PD-1 (structural formula shown below), wherein the mass percent of HT: PD-1 is 95%: 5%/hole transport layer 122, HT (90 nm)/blue light hole transport layer 132, B-HTL (20 nm)/blue light emitting layer 142, B-EML BH: BD (30nm, mass percent 97%: 3%)/hole blocking layer 152, HB (10 nm)/electron transport layer 162, ETL (X): LIQ (30nm, mass percent 50%: 50%)/cathode 103, and Mg: Ag (50nm, mass percent 10%: 90%). In table 1, the preparation methods and test conditions of the respective layers of the OLED devices of the examples and comparative examples are the same.
Table 1:
Figure BDA0002040236240000121
specifically, the structural formulas of the compound 1, the compound 2, the compound 3, PD-1, HT, B-HTL, BH, BD, HB, LIQ, REF1 and REF2 are as follows:
compound 1:
Figure BDA0002040236240000122
compound 2:
Figure BDA0002040236240000123
compound 3:
Figure BDA0002040236240000124
PD-1：
Figure BDA0002040236240000125
HT：
Figure BDA0002040236240000126
B-HTL
Figure BDA0002040236240000127
BH：
Figure BDA0002040236240000131
BD：
Figure BDA0002040236240000132
HB：
Figure BDA0002040236240000133
LIQ：
Figure BDA0002040236240000134
REF1：
Figure BDA0002040236240000135
REF2：
Figure BDA0002040236240000136
as can be seen from table 1, when the organic electroluminescent material provided by the present invention is mixed with 8-hydroxyquinoline Lithium (LIQ) as a metal compound material to prepare the electron transport layer of the OLED device, the bottom-emitting OLED device has a lower voltage and higher light efficiency, so that the performance of the OLED device can be improved, and the application range of the OLED device can be expanded.
As shown in fig. 2, the present invention also provides a bottom emission device, which sequentially includes, from bottom to top: the anode 201, ITO (15 nm)/hole injection layer 212, HI (10nm) are mixed materials of HT (structural formula shown below) and PD-1 (structural formula shown below), wherein the mass percent of HT: PD-1 is 95%: 5%/hole transport layer 222, HT (90 nm)/blue light hole transport layer 232, B-HTL (20 nm)/blue light emitting layer 242, B-EML BH: BD (30nm, mass percent 97%: 3%)/hole barrier layer 252, HB (10 nm)/electron transport layer 262, ETL (X): Yb (30nm, mass percent 95%: 5%)/cathode 203, and Ag (50 nm). It should be noted that, in table 2, the preparation methods and test conditions of the respective layers of the example and comparative OLED devices were the same.
Table 2:
Figure BDA0002040236240000137
specifically, the structural formulas of the compounds 1, 2, 3, PD-1, HT, B-HTL, BH, BD, HB, REF1 and REF2 are the same as above.
As can be seen from table 2, the organic electroluminescent material provided by the present invention is applied to the electron transport layer, and the electron transport layer is prepared by mixing the organic electroluminescent material and the metal material Yb, so that the formed light emitting OLED device has a lower voltage and a higher light efficiency, thereby improving the performance of the OLED device and expanding the application range of the OLED device.
In summary, the organic electroluminescent material provided by the invention has higher electron transport capacity, can be applied to an organic electroluminescent device as an electron transport layer, can reduce the driving voltage of the device, improves the luminous efficiency of the device, prolongs the service life of the device, and thus expands the application range of the device. Therefore, the invention effectively overcomes various defects in the prior art and has high industrial utilization value.
The foregoing embodiments are merely illustrative of the principles and utilities of the present invention and are not intended to limit the invention. Any person skilled in the art can modify or change the above-mentioned embodiments without departing from the spirit and scope of the present invention. Accordingly, it is intended that all equivalent modifications or changes which can be made by those skilled in the art without departing from the spirit and technical spirit of the present invention be covered by the claims of the present invention.

Claims (10)

1. An organic electroluminescent material, characterized in that the structural general formula of the organic electroluminescent material is as follows:
Figure FDA0002040236230000011
wherein L comprises a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms in a ring, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms in a ring, or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms in a ringAralkyl having 7 to 30 carbon atoms; r1、R2The organic silicon-organic composite material comprises the same or different single bonds, and each single bond, substituted or unsubstituted aryl with 6-30 carbon atoms in a ring form, substituted or unsubstituted heteroaryl with 5-30 carbon atoms in a ring form, substituted or unsubstituted alkyl with 1-30 carbon atoms, substituted or unsubstituted fluoroalkyl with 1-30 carbon atoms, substituted or unsubstituted cycloalkyl with 3-30 carbon atoms in a ring form, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted phosphoryl, substituted silyl, substituted germanium groups, cyano groups, nitro groups or carboxyl groups.
2. The organic electroluminescent material according to claim 1, wherein: the organic electroluminescent material is selected from any one of the following compounds:
Figure FDA0002040236230000012
Figure FDA0002040236230000021
Figure FDA0002040236230000031
3. Use of an organic electroluminescent material according to any one of claims 1 to 2 in an organic electroluminescent device; the organic electroluminescent material is used as an electron transport layer in the organic electroluminescent device.
4. An organic electroluminescent device, characterized in that: the organic electroluminescent device comprises an anode, a cathode and an organic layer positioned between the anode and the cathode, wherein the organic layer comprises an electron transport layer, and the electron transport layer comprises the organic electroluminescent material as claimed in any one of claims 1 to 2.
5. The organic electroluminescent device according to claim 4, wherein: the electron transport layer further comprises a metal material, the metal comprising one or a combination of an alkali metal, an alkaline earth metal, and a rare earth metal; the metal comprises one or a combination of ytterbium metal, samarium metal, europium metal and dysprosium metal.
6. The organic electroluminescent device according to claim 4, wherein: the electron transport layer further comprises a metal compound, wherein the metal compound comprises one or a combination of an alkali metal compound, an alkaline earth metal compound and a rare earth metal compound; the metal compound comprises one or a combination of 8-hydroxyquinoline lithium and lithium fluoride.
7. The organic electroluminescent device according to claim 4, wherein: in the electron transport layer, the mass percentage of the organic electroluminescent material ranges from 80% to 99%.
8. The organic electroluminescent device according to claim 4, wherein: the organic light-emitting device comprises one or a combination of a top light-emitting device and a bottom light-emitting device, wherein the top light-emitting device further comprises an optical coupling layer.
9. A display device, characterized in that: the display device includes the organic electroluminescent element as claimed in any one of claims 4 to 8.
10. An electronic device, characterized in that: the electronic device comprises the organic electroluminescent device as claimed in any one of claims 4 to 8.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104247070A (en) * 2011-11-30 2014-12-24 诺瓦尔德股份有限公司 Display
EP2999019A1 (en) * 2014-09-19 2016-03-23 Novaled GmbH Organic light-emitting diode including an electron transport layer stack comprising different lithium compounds and elemental metal
CN108059643A (en) * 2018-01-18 2018-05-22 长春海谱润斯科技有限公司 A kind of electroluminescent organic material and its organic luminescent device
CN108463898A (en) * 2015-12-18 2018-08-28 诺瓦尔德股份有限公司 Electron injecting layer for Organic Light Emitting Diode (OLED)

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104247070A (en) * 2011-11-30 2014-12-24 诺瓦尔德股份有限公司 Display
EP2999019A1 (en) * 2014-09-19 2016-03-23 Novaled GmbH Organic light-emitting diode including an electron transport layer stack comprising different lithium compounds and elemental metal
CN108463898A (en) * 2015-12-18 2018-08-28 诺瓦尔德股份有限公司 Electron injecting layer for Organic Light Emitting Diode (OLED)
CN108059643A (en) * 2018-01-18 2018-05-22 长春海谱润斯科技有限公司 A kind of electroluminescent organic material and its organic luminescent device

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