CN111004253B - OLED material and application thereof - Google Patents

OLED material and application thereof Download PDF

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CN111004253B
CN111004253B CN201911194860.2A CN201911194860A CN111004253B CN 111004253 B CN111004253 B CN 111004253B CN 201911194860 A CN201911194860 A CN 201911194860A CN 111004253 B CN111004253 B CN 111004253B
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CN111004253A (en
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段陆萌
范洪涛
黄春雪
杭德余
梁现丽
李仲庆
曹占广
刘阳
班全志
李继响
罗忠林
呼建军
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Beijing Yanhua Jilian Optoelectronic Technology Co ltd
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Abstract

The invention relates to an OLED material which has any one structure shown in general formulas I to III. The OLED material provided by the invention takes forced-ton and ton as a parent nucleus, and the compound has a wider band gap, a high T1 energy level and a proper Highest Occupied Molecular Orbital (HOMO) energy level. The compound has high thermal stability, is not easy to decompose in the sublimation process, has higher glass transition temperature, and can maintain the phase stability of a formed film. The invention further ensures that the luminescent material is not easy to crystallize and quench and has good film-forming property by introducing the group with larger steric hindrance. The OLED material provided by the invention is preferably used as an electron transport material of an electron transport layer in an organic electroluminescent device.

Description

OLED material and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescence display, in particular to an OLED material and application thereof.
Background
The application of the organic electroluminescent (OLED) material in the fields of information display materials, organic optoelectronic materials and the like has great research value and good application prospect. With the development of multimedia information technology, the requirements for the performance of flat panel display devices are higher and higher. The main display technologies at present are plasma display devices, field emission display devices, and organic electroluminescent display devices (OLEDs). The OLED has a series of advantages of self luminescence, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like, and compared with a liquid crystal display device, the OLED does not need a backlight source, has a wider viewing angle and low power consumption, has the response speed 1000 times that of the liquid crystal display device, and has a wider application prospect.
At present, the commonly used electron transport materials such as AlQ3 have low electron mobility, so that the working voltage of the device is higher, and the power consumption is serious; some electron transport materials such as LG201 are not high in triplet level, and when a phosphorescent light emitting material is used as a light emitting layer, an exciton blocking layer needs to be added, otherwise efficiency is reduced, and some materials such as Bephen are easily crystallized, resulting in a reduction in lifetime. Therefore, the stable and efficient electron transport material is developed, so that the driving voltage is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the method has important practical application value.
Disclosure of Invention
The invention aims to provide an OLED electron transport material which can reduce the driving voltage, improve the luminous efficiency of a device and prolong the service life of the device, and an OLED element which uses the material and has high efficiency.
Specifically, the invention provides an OLED material, which has any one of the structures shown in general formulas I-III:
Figure BDA0002294440940000011
in the general formulas I to III, R1By substitution of H atoms at any one or two positions on the phenyl ring in which it is located, R2By substitution of H atoms in any one, two or three positions of the phenyl ring in which they are located, R3By substitution of H atoms in any one, two or three positions of the phenyl ring in which they are located, R4Substituted with H atoms at any one, two or three positions on the phenyl ring on which it is located.
The R is1、R2、R3、R4Each independently represents-H, -F, -Cl, -Br, -I, -n (Ar), -C (═ O) Ar, -P (═ O) Ar, -S (═ O)2Ar、-OAr、-SAr、-CN、-NO2An alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms or a sulfoalkoxy group having 1 to 40 carbon atoms.
The alkyl group having 1 to 40 carbon atoms may be a straight-chain alkyl group having 1 to 40 carbon atoms, a branched-chain alkyl group having 3 to 40 carbon atoms, or a cyclic alkyl group having 3 to 40 carbon atoms.
The alkoxy group having 1 to 40 carbon atoms may be a linear alkoxy group having 1 to 40 carbon atoms, a branched alkoxy group having 3 to 40 carbon atoms, or a cyclic alkoxy group having 3 to 40 carbon atoms.
The thioalkoxy group having 1 to 40 carbon atoms may be a linear thioalkoxy group having 1 to 40 carbon atoms, a branched thioalkoxy group having 3 to 40 carbon atoms, or a cyclic thioalkoxy group having 3 to 40 carbon atoms.
The R is1、R2、R3、R4The groups represented by each may be different, any two of them may be the same and different from the remaining two, any three of them may be the same and different from the remaining one, or four of them may be the same.
As a specific embodiment of the present invention, R is1、R2、R3、R4All represent H atoms.
The invention has the general formula I &III to Ar1、Ar2The respective substitution positions are preferably selected to enhance the overall performance of the compound.
Specifically, the method comprises the following steps:
in the general formula II, Ar1、Ar2The respective specific substitution positions are preferably as shown in the general formulae II-1 to II-3.
Figure BDA0002294440940000021
In the general formula III, Ar1、Ar2The respective specific substitution positions are preferably as shown in the general formulae III-1 to III-6.
Figure BDA0002294440940000022
Figure BDA0002294440940000031
As a specific embodiment of the invention, the OLED material has a structure shown as a general formula II-1.
As a specific embodiment of the present invention, the OLED material has a structure shown in the general formula II-1'.
Figure BDA0002294440940000032
Ar of the invention1、Ar2Each independently represents an aromatic group having an electron-withdrawing property having a benzene ring and/or an aromatic heterocyclic ring or represents an H atom, and Ar1、Ar2Not H atoms at the same time.
Preferably, Ar is1、Ar2Each independently selected from the group consisting of:
Figure BDA0002294440940000033
Figure BDA0002294440940000041
more preferably, Ar is1、Ar2Each independently selected from the group consisting of:
Figure BDA0002294440940000042
ar is1、Ar2The substituents represented by each may be the same or different.
In each of the above-mentioned substituent groups,
Figure BDA0002294440940000051
or "- - -" represents a substituted position.
As a particular embodiment of the invention, the OLED material is selected from the following specific compounds:
Figure BDA0002294440940000052
Figure BDA0002294440940000061
Figure BDA0002294440940000071
Figure BDA0002294440940000081
Figure BDA0002294440940000091
the invention also provides a preparation method of the OLED material.
When in formula I Ar1、Ar2The radicals being identical, i.e. Ar1、Ar2When all Ar is contained, the method for synthesizing the compound shown in the general formula I comprises the following steps: taking a compound P-I as a raw material, and carrying out a coupling reaction with Ar to obtain a compound I;
the reaction process is as follows:
Figure BDA0002294440940000101
when in formula I Ar1、Ar2When the groups are different, the method for synthesizing the compound shown in the general formula I comprises the following steps: taking a compound P-I' as a raw material, and sequentially reacting with Ar1、Ar2Carrying out coupling reaction to obtain a compound I;
the reaction process is as follows:
Figure BDA0002294440940000102
when in formula II Ar1、Ar2The radicals being identical, i.e. Ar1、Ar2When both are Ar, the method for synthesizing the compound shown in the general formula II comprises the following steps: taking a compound P-II as a raw material, and carrying out a coupling reaction with Ar to obtain a compound II;
the reaction process is as follows:
Figure BDA0002294440940000103
when in formula II Ar1、Ar2When the groups are different, the method for synthesizing the compound shown in the general formula II comprises the following steps: taking a compound P-II 'as a raw material, and reacting the compound P-II' with Ar in sequence1、Ar2Carrying out coupling reaction to obtain a compound II;
the reaction process is as follows:
Figure BDA0002294440940000111
when in formula III Ar1、Ar2The radicals being identical, i.e. Ar1、Ar2When both are Ar, the method for synthesizing the compound shown in the general formula III comprises the following steps: taking a compound P-III as a raw material, and carrying out a coupling reaction with Ar to obtain a compound III;
the reaction process is as follows:
Figure BDA0002294440940000112
when in formula III Ar1、Ar2When the groups are different, the method for synthesizing the compound shown in the general formula III comprises the following steps: taking a compound P-III 'as a raw material, and reacting the compound P-III' with Ar in sequence1、Ar2Carrying out coupling reaction to obtain a compound III;
the reaction process is as follows:
Figure BDA0002294440940000113
the above steps can be carried out by a person skilled in the art by known and conventional means, such as selecting a suitable catalyst, solvent, determining a suitable reaction temperature, time, etc.
In the above process for preparing a compound represented by any one of the general formulae I to III, when Ar is Ar1、Ar2The radicals being identical, i.e. Ar1、Ar2When both are Ar, as a preferred embodiment of the present invention, the method comprises: and (2) taking xylene as a reaction solvent, cuprous chloride as a catalyst, potassium hydroxide as an alkali, controlling the temperature to be 75-85 ℃ under the protection of nitrogen, and performing a coupling reaction on the raw materials and Ar to obtain the target compound.
In the above process for preparing a compound represented by any one of the general formulae I to III, when Ar is Ar1、Ar2When the groups are different, as a preferred embodiment of the present invention, the method comprises: first xylene is used as reaction solvent toCuprous chloride is used as a catalyst, potassium hydroxide is used as alkali, nitrogen is used for protection, the temperature is controlled to be 75-85 ℃, and the raw material and Ar are mixed1Coupling reaction is carried out to obtain an intermediate product; and then taking toluene as a solvent, palladium acetate and tri-tert-butylphosphine as catalysts, potassium tert-butoxide as an alkali, protecting with nitrogen, controlling the temperature to be 90-120 ℃, and reacting the intermediate product and Ar2Coupling reaction is carried out to obtain the target compound.
The starting materials for the solvents, catalysts, bases, etc., used in the present invention can be synthesized by published commercial routes or methods known in the art.
The invention also protects the application of the OLED material in an organic electroluminescent device. Preferably, the OLED material is used as an electron transport material in an electron transport layer.
The invention also provides an organic electroluminescent device, and an electronic transmission layer of the organic electroluminescent device contains the OLED material. Specifically, the organic electroluminescent device protected by the invention sequentially comprises a transparent substrate, an anode layer, a hole transport layer, an electroluminescent layer, an electron transport layer, an electron injection layer and a cathode layer which are formed by the OLED material.
The OLED material provided by the invention takes forced-ton and ton as a parent nucleus, and the compound has a wider band gap, a high T1 energy level and a proper Highest Occupied Molecular Orbital (HOMO) energy level. The compound has high thermal stability and is not easy to decompose in the sublimation process. And has higher glass transition temperature, and can maintain the phase stability of the formed film. By introducing a group with larger steric hindrance, the luminescent material is further difficult to crystallize and quench and has good film-forming property.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
According to some embodiments of the present invention, the preferred solvent for preparing the organic electroluminescent device according to the present invention is selected from toluene, DMF or a mixture of these solvents. The reagents are analytically pure reagents, and the intermediate is purchased from an online shopping mall or is custom-synthesized from outsourcing companies.
Example 1
Figure BDA0002294440940000121
Synthesis of (Compound II-1-4)
The synthetic route is as follows:
Figure BDA0002294440940000131
synthesis of Compound II-1-4
A1L three-necked flask was stirred with magnetic stirring and then replaced with nitrogen, and 40.07g (0.378mol) of sodium carbonate, 58.59g (purity 99%, 0.21mol) of phenanthro [9,10-d ] thiazol-2-ylboronic acid and 100ml of toluene were sequentially added. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. Dropwise addition was started in a solution consisting of 53.6g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene, the temperature being controlled at 75-90 ℃. Cooling to room temperature, adding 100ml deionized water for hydrolysis, stirring for 10 min, filtering, and boiling the filter cake with DMF for several times to obtain 67.52g of light yellow solid with purity of 99% and yield of 80%.
Product MS (m/e): 844; elemental analysis (C)50H24N2O4S4): theoretical value C: 71.07 percent; h: 2.86 percent; n: 3.32 percent; o: 7.57 percent; s: 15.18 percent; found value C: 71.06 percent; h: 2.87 percent; n: 3.32 percent; o: 7.57 percent; s: 15.18 percent.
Example 2
Figure BDA0002294440940000132
Synthesis of (Compound II-1-7)
The synthetic route is as follows:
Figure BDA0002294440940000133
synthesis of Compound II-1-7
A1 liter three-necked flask was equipped with magnetic stirring, and after nitrogen substitution, 40.07g (0.378mol) of sodium carbonate, 65.94g (purity 99%, 0.21mol) of 4- (1-phenyl-1H-benzo [ d ] imidazol-2-yl) phenyl) boronic acid and 100ml of toluene were added in this order. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. Dropwise addition was started in a solution consisting of 53.6g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene, the temperature being controlled at 75-90 ℃. Cooling to room temperature, adding 100ml deionized water for hydrolysis, stirring for 10 min, filtering, and boiling the filter cake with DMF for several times to obtain 75.86g of light yellow solid with purity of 99% and yield of 83%.
Product MS (m/e): 914; elemental analysis (C)58H34N4O4S2): theoretical value C: 76.13 percent; h: 3.75 percent; n: 6.12 percent; o: 6.99 percent; s: 7.01; found value C: 76.12 percent; h: 3.76 percent; n: 6.12 percent; o: 6.99 percent; s: 7.01.
example 3
Figure BDA0002294440940000141
Synthesis of (Compound II-1-12)
The synthetic route is as follows:
Figure BDA0002294440940000142
synthesis of Compound II-1-12
A1 liter three-necked flask was stirred with magnetic stirring and then purged with nitrogen, followed by addition of 20.14g (0.19mol) of sodium carbonate, 17.93g (purity: 99%, 0.11mol) of benzo [ d ] oxazol-2-ylboronic acid and 100ml of toluene in this order. After nitrogen replacement again, 0.25g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. Dropwise addition was started in a solution consisting of 53.6g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene, the temperature being controlled at 75-90 ℃. Cooling to room temperature, adding 100ml deionized water for hydrolysis, stirring for 10 min, filtering, and repeatedly boiling the filter cake with DMF for several times to obtain 39.10g of light yellow solid with purity of 99% and yield of 79%.
Product MS (m/e): 495; elemental analysis (C)27H13NO5S2): theoretical value C: 65.44 percent; h: 2.64 percent; n: 2.83 percent; o: 16.14 percent; s: 12.94; found value C: 65.43 percent; h: 2.65 percent; n: 2.83 percent; o: 16.14 percent; s: 12.94.
example 4
Figure BDA0002294440940000151
Synthesis of (Compound II-1-18)
The synthetic route is as follows:
Figure BDA0002294440940000152
synthesis of Compound II-1-18
A1 liter three-necked flask was equipped with magnetic stirring, and after nitrogen substitution, 40.07g (0.378mol) of sodium carbonate, 60.27g (purity 99%, 0.21mol) of 6-phenylpyridin-3-yl) boronic acid and 100ml of toluene were added in this order. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. Dropwise addition was started in a solution consisting of 53.6g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene, the temperature being controlled at 75-90 ℃. Cooling to room temperature, adding 100ml deionized water for hydrolysis, stirring for 10 min, filtering, and boiling the filter cake with DMF for several times to obtain 56.09g of light yellow solid with purity of 99% and yield of 82%.
Product MS (m/e): 684; elemental analysis (C)42H24N2O4S2): theoretical value C: 73.67 percent; h: 3.53 percent; n: 4.09%; o: 9.35 percent; s: 9.37; found value C: 73.66 percent; h: 3.54 percent; n: 4.09%; o: 9.35 percent; s: 9.37.
example 5
Figure BDA0002294440940000153
Synthesis of (Compound II-1-26)
The synthetic route is as follows:
Figure BDA0002294440940000161
synthesis of Compound II-1-26
A1 liter three-necked flask was equipped with magnetic stirring, and after nitrogen substitution, 20.14g (0.378mol) of sodium carbonate, 30.36g (purity 99%, 0.11mol) of 3, 5-bis (pyridin-3-yl) phenyl) boronic acid and 100ml of toluene were added in this order. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. Dropwise addition was started in a solution consisting of 53.6g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene, the temperature being controlled at 75-90 ℃. Cooling to room temperature, adding 100ml deionized water for hydrolysis, stirring for 10 min, filtering, and boiling the filter cake with DMF for several times to obtain 47.42g of light yellow solid with purity of 99% and yield of 78%.
Product MS (m/e): 608; elemental analysis (C)36H20N2O4S2): theoretical value C: 71.04 percent; h: 3.31 percent; n: 4.60 percent; o: 10.51 percent; s: 10.54; found value C: 71.03 percent; h: 3.32 percent; n: 4.60 percent; o: 10.51 percent; s: 10.54.
example 6
Figure BDA0002294440940000162
Synthesis of (Compound II-1-34)
The synthetic route is as follows:
Figure BDA0002294440940000163
synthesis of Compound II-1-34-1
A1 liter three-necked flask was equipped with magnetic stirring, and after nitrogen substitution, 20.14g (0.19mol) of sodium carbonate, 19.69g (purity 99%, 0.11mol) of benzo [ d ] thiazol-2-ylboronic acid and 100ml of toluene were sequentially added. After nitrogen replacement again, 0.25g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. Dropwise addition was started in a solution consisting of 53.6g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene, the temperature being controlled at 75-90 ℃. Cooling to room temperature, adding 100ml deionized water for hydrolysis, stirring for 10 min, filtering, and boiling the filter cake with DMF for several times to obtain 29.5g of light yellow solid with purity of 99% and yield of 50%.
Synthesis of Compound II-1-34
A1 liter three-necked flask was equipped with magnetic stirring, and after nitrogen substitution, 20.14g (0.19mol) of sodium carbonate, 26.18g (purity 99%, 0.11mol) of (1-phenyl-1H-benzo [ d ] imidazol-2-yl) boronic acid and 100ml of toluene were added in this order. After nitrogen replacement again, 0.25g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. A solution consisting of 59g of Compound II-1-34-1 (purity 99%, 0.1mol) and 100ml of toluene was initially added dropwise, the temperature being controlled at 75-90 ℃. Cooling to room temperature, adding 100ml deionized water for hydrolysis, stirring for 10 min, filtering, and boiling the filter cake with DMF for several times to obtain 54.83g of light yellow solid with purity of 99% and yield of 78%.
Product MS (m/e): 703; elemental analysis (C)40H21N3O4S3): theoretical value C: 68.26 percent; h: 3.01 percent; n: 5.97 percent; o: 9.09%; s: 13.67 percent; found value C: 68.25 percent; h: 3.02 percent; n: 5.97 percent; o: 9.09%; s: 13.67 percent.
According to the technical schemes of the examples 1 to 6, the compounds shown in II-1-1 to II-1-62 can be synthesized only by simply replacing the corresponding raw materials without changing any substantial operation.
Preparation of device examples
(1) Carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1: 1), baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
(2) placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3PP1, evaporating HATCN as a first hole injection layer on the anode layer film in vacuum, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 1 nm; then evaporating a second hole injection layer HT01 at the evaporation rate of 0.1nm/s and the thickness of 40 nm;
Figure BDA0002294440940000171
(3) evaporating and plating a layer of NPB (nitrogen-phosphorus) on the hole injection layer film to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 20 nm;
Figure BDA0002294440940000181
(4) EML is evaporated on the hole transport layer in vacuum and used as a light emitting layer of the device, the EML comprises a main material and a dye material, the evaporation rate of the main material PRH01 is adjusted to be 0.1nm/s by using a multi-source co-evaporation method, and the dye material Ir (piq)2The acac concentration is 5%, and the total film thickness of evaporation plating is 30 nm;
Figure BDA0002294440940000182
(5) continuously evaporating a layer of the compound II-1-4 provided in the embodiment 1 on the organic light-emitting layer to be used as an electron transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 30 nm;
(6) continuously evaporating a layer of LiF on the electron transport layer to be used as an electron injection layer of the device, wherein the thickness of the evaporated film is 0.5 nm;
(7) continuously evaporating a layer of Al on the electron injection layer to be used as a cathode of the device, wherein the thickness of the evaporated film is 150 nm; the OLED device provided by the invention is obtained and is marked as OLED-1.
According to the same steps as above, replacing the compound II-1-4 in the step (5) with the compound obtained in the example 2-6, and obtaining devices OLED-2-OLED-6.
According to the same procedure as above, compound II-1-4 in step (5) was replaced with a comparative compound (structure shown below), to give a comparative device OLED-7.
Figure BDA0002294440940000183
Comparative Compound 1
The results of the performance tests of the devices OLED-1 to OLED-7 are shown in Table 1.
Table 1: performance test results of OLED-1 to OLED-7
Figure BDA0002294440940000184
Figure BDA0002294440940000191
From the above results, the current efficiency of the devices OLED-1 to OLED-6 prepared by using the OLED material provided by the invention is higher, and the working voltage is obviously lower than that of the device OLED-7 taking the comparative compound 1 as the electron transport material under the condition of the same brightness.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (7)

1. An OLED material having a structure according to formula II-1':
Figure FDA0002995233730000011
Ar1、Ar2each independently selected from the group consisting of1、Ar2May be the same or different, and Ar1、Ar2Not H atoms at the same time;
Figure FDA0002995233730000012
Figure FDA0002995233730000021
2. the material of claim 1, wherein Ar is Ar1、Ar2Each independently selected from the group consisting of:
Figure FDA0002995233730000022
3. the material according to claim 1, characterized in that it is selected from compounds of the following specific structure:
Figure FDA0002995233730000023
Figure FDA0002995233730000031
Figure FDA0002995233730000041
Figure FDA0002995233730000051
Figure FDA0002995233730000061
Figure FDA0002995233730000071
4. use of the OLED material of any one of claims 1 to 3 in an organic electroluminescent device.
5. Use according to claim 4, characterized in that the material is used as an electron transport material in an electron transport layer.
6. An organic electroluminescent device, characterized in that an electron transport layer contains the OLED material according to any one of claims 1 to 3.
7. An organic electroluminescent device, characterized in that, in the organic functional layer of the organic electroluminescent device, the OLED material of any one of claims 1 to 3 is used as an electron transport material in an electron transport layer.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101490208A (en) * 2006-07-28 2009-07-22 默克专利有限公司 Novel materials for organic electroluminescent devices
US20120205630A1 (en) * 2011-02-10 2012-08-16 Xerox Corporation Semiconductor compound
CN103087065A (en) * 2011-11-03 2013-05-08 三星显示有限公司 Ovel Heterocyclic Compound, Organic Light-emitting Device Including The Same And Flat Panel Display Device
CN109503457A (en) * 2018-11-03 2019-03-22 浙江大学 Dinaphtho heterocycle small molecule hole transport material, synthetic method and its application

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101490208A (en) * 2006-07-28 2009-07-22 默克专利有限公司 Novel materials for organic electroluminescent devices
US20120205630A1 (en) * 2011-02-10 2012-08-16 Xerox Corporation Semiconductor compound
CN103087065A (en) * 2011-11-03 2013-05-08 三星显示有限公司 Ovel Heterocyclic Compound, Organic Light-emitting Device Including The Same And Flat Panel Display Device
CN109503457A (en) * 2018-11-03 2019-03-22 浙江大学 Dinaphtho heterocycle small molecule hole transport material, synthetic method and its application

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