CN109928886B - Compound containing triarylamine and fluorene and application thereof - Google Patents
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Abstract
The invention discloses a triarylamine and fluorene-containing compound and application thereof, and the structure of the organic compound provided by the invention is shown as a general formula (1).
The compound provided by the invention has higher glass transition temperature, higher molecular thermal stability and proper HOMO energy level, and can effectively improve the photoelectric property of an OLED device and the service life of the OLED device through device structure optimization.
Description
Technical Field
The invention relates to the technical field of semiconductor materials, in particular to a triarylamine and fluorene-containing compound and application thereof in an organic electroluminescent device.
Background
The Organic Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect. The OLED light-emitting device is like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and various different functional materials are mutually overlapped together according to purposes to form the OLED light-emitting device. When voltage is applied to electrodes at two ends of the OLED light-emitting device and positive and negative charges in the organic layer functional material film layer are acted through an electric field, the positive and negative charges are further compounded in the light-emitting layer, and OLED electroluminescence is generated.
Currently, the OLED display technology is already applied in the fields of smart phones, tablet computers, and the like, and is further expanded to the large-size application field of televisions, and the like, but compared with the actual product application requirements, the performance of the OLED device, such as light emitting efficiency, service life, and the like, needs to be further improved. Current research into improving the performance of OLED light emitting devices includes: 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 innovation of the structure and the manufacturing process of the OLED device but also the continuous research and innovation of the photoelectric functional material of the OLED are required to create the functional material of the OLED with higher performance.
The photoelectric functional materials of the OLED applied to the OLED device can be divided into two categories from the aspect of application, namely charge injection transmission materials and luminescent materials. Further, the charge injection transport material may be classified into an electron injection transport material, an electron blocking material, a hole injection transport material, and a hole blocking material, and the light emitting material may be classified into a host light emitting material and a doping material.
In order to fabricate a high-performance OLED light-emitting device, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, good carrier mobility, high glass transition temperature, etc. are required, as a host material of a light-emitting layer, good bipolar, appropriate HOMO/LUMO energy level, etc. are required.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, the OLED device structure applied in industry comprises a hole injection layer, a hole transmission layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transmission layer, an electron injection layer and other various film layers, namely the photoelectric functional material applied to the OLED device at least comprises a hole injection material, a hole transmission material, a light emitting material, an electron transmission material and the like, and the material type and the matching form have the characteristics of richness and diversity. In addition, for the collocation of OLED devices with different structures, the used photoelectric functional material has stronger selectivity, and the performance of the same material in the devices with different structures can be completely different.
Therefore, aiming at the industrial application requirements of the current OLED device and the requirements of different functional film layers and photoelectric characteristics of the OLED device, a more suitable OLED functional material or material combination with higher performance needs to be selected to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device. In terms of the actual demand of the current OLED display lighting industry, the development of the current OLED material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and it is very important to develop a higher-performance organic functional material as a material enterprise.
Disclosure of Invention
In view of the above problems in the prior art, the present applicant provides a triarylamine and fluorene-containing compound and its application. The compound contains triarylamine and fluorene, has higher glass transition temperature and molecular thermal stability and proper HOMO energy level, and can effectively improve the photoelectric property of an OLED device and the service life of the OLED device through device structure optimization.
The technical scheme of the invention is as follows: a compound containing triarylamine and fluorene, wherein the structure of the compound is shown as a general formula (1):
in the general formula (1), Ar1、Ar2、Ar3、Ar4、Ar5、R1And R2Each independently represents substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C2-C30A heteroaryl group; and R is1And R2Independently exist or are bonded with each other to form a ring; l is1、L2、L3、L4The indicated position is indicated as the attachment site to N;
when R is1、R2Represented by phenyl, the site of attachment to N being L2At the indicated position, Ar1Is not represented as phenyl;
by "substituted" is meant that at least one hydrogen atom is replaced by a substituent selected from the group consisting of: halogen atom, cyano group, C1-C20Alkyl of (C)3-C20Cycloalkyl of, C1-C20Alkoxy group of (C)6-C30Aryl radical, C2-C30A heteroaryl group;
the heteroatom in the heteroaryl group is selected from N, O or S.
As a further improvement of the invention, Ar is1、Ar2、Ar3、Ar4、Ar5Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted naphthyl groupA substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted naphthyridinyl group substituted or unsubstituted by a substituted or unsubstituted quinazolinyl group, a structure represented by general formula (2) or general formula (3);
in the general formula (2) and the general formula (3), Z is represented by C, N or C-R3；R3Represented by hydrogen atom, protium atom, deuterium atom, tritium atom, halogen, cyano group, C1-C10Alkyl of (C)1-C10Alkoxy group of (C)6-C30Aryl radical, C2-C30A heteroaryl group;
in the general formula (2), X is1Represented by-O-, -S-, -C (R)4)(R5) -or-N (R)6)-；R4、R5Are each independently represented by C1-C20Alkyl of (C)1-C20Alkoxy group of (C)6-C30Aryl radical, C2-C30A heteroaryl group; r6Represented by substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl;
in the general formula (3), L represents a single bond, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted azaphenyl group;
by "substituted" is meant that at least one hydrogen atom is replaced by a substituent selected from the group consisting of: halogen atom, cyano group, C1-C20Alkyl of (C)3-C20Cycloalkyl of, C1-C20Alkoxy group of (C)6-C30Aryl radical, C2-C30A heteroaryl group;
the heteroatom in the heteroaryl group is selected from N, O or S.
As the inventionIn a further improvement, said R1And R2Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted hetero phenyl, substituted or unsubstituted biphenyl and substituted or unsubstituted naphthyl; and R is1And R2Do not form a ring or bond to each other to form a ring;
the R is3Represented by a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a fluorine atom, a cyano group, a methyl group, a methoxy group, an ethoxy group, an isopropyl group, a tert-butyl group, a phenyl group, a biphenyl group, a naphthyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spirofluorenyl group, a dibenzofuranyl group, a carbazolyl group, a dibenzothiophenyl group, a pyridyl group, a naphthyridinyl group or a carbazolinyl group;
the R is4And R5Each independently represents methyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, carbazolyl, dibenzothienyl, pyridyl, naphthyridinyl or carbazolinyl; r4And R5May be bonded to each other to form a ring;
ar is1、Ar2、Ar3、Ar4、Ar5Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted naphthyridinyl;
the substituent is selected from one or more of fluorine atom, cyano, methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, amyl, hexyl, cyclohexyl, adamantyl, methoxy, ethoxy, phenyl, biphenyl, naphthyl, furyl, carbazolyl, thienyl or pyridyl.
The heteroatom in the heteroaryl group is selected from N, O or S.
As a further improvement of the invention, the compound of the general formula (1) has a specific structure:
the application of the compound containing triarylamine and fluorene in the preparation of organic electroluminescent devices.
An organic electroluminescent device, wherein a plurality of organic thin film layers are arranged between an anode and a cathode of the organic electroluminescent device, and at least one organic thin film layer contains the compound containing triarylamine and fluorene.
As a further improvement of the invention, the electron blocking material or the hole transport material of the organic electroluminescent device contains the triarylamine and fluorene-containing compound.
A lighting or display element comprising the organic electroluminescent device.
Compared with the prior art, the invention has the beneficial technical effects that:
(1) the compound contains an aromatic amino electron-donating group, has high triplet state energy level (T1), can effectively block exciton energy of a light-emitting layer from being transferred to a hole transport layer when being used as an electron blocking layer material of an OLED light-emitting device, improves the recombination efficiency of excitons in the light-emitting layer, improves the energy utilization rate and further improves the light-emitting efficiency of the device.
(2) The pi conjugated effect in the compound of the invention ensures that the compound has strong hole transmission capability, and when the compound is used as a hole transmission layer material of an OLED light-emitting device, the high hole transmission rate can reduce the initial voltage of the device and improve the efficiency of the organic electroluminescent device.
(3) The branched chains of the compound are radial, so that the distance between molecules is increased, and the compound has higher Tg temperature and smaller intermolecular force. The compound has lower evaporation temperature due to smaller intermolecular force, thereby not only ensuring that the evaporation material is not decomposed for a long time in mass production, but also reducing the deformation influence of heat radiation of the evaporation temperature on the Mask.
(4) The compound of the invention ensures that the distribution of electrons and holes in the luminescent layer is more balanced, and under the proper HOMO energy level, the hole injection and transmission performance is improved; under a proper LUMO energy level, the organic electroluminescent material plays a role in blocking electrons, and improves the recombination efficiency of excitons in the luminescent layer; the exciton utilization rate and the high fluorescence radiation efficiency can be effectively improved, the voltage of the device is reduced, the current efficiency of the device is improved, and the service life of the device is prolonged; thereby making it easier to obtain high efficiency of the device. The compound has good application effect in OLED luminescent devices and good industrialization prospect.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
in the figure: 1 is a transparent substrate layer, 2 is an ITO anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is an electron transport or hole blocking layer, 8 is an electron injection layer, 9 is a cathode reflective electrode layer, and 10 is a light extraction layer.
Fig. 2 is a graph of the current efficiency of the device of the present invention as a function of temperature.
Detailed Description
The present invention will be described in detail with reference to the accompanying drawings and examples.
All the raw materials in the following examples were purchased from cigarette Taiwangrun Fine chemical Co., Ltd.
The synthesis of intermediate E is as follows, and for the sake of clarity, the same species appears in different reactions with different reference numerals; taking the synthesis example of intermediate E1:
(1) a250 ml three-necked flask was charged with 0.12mol of A1 as a starting material, 0.1mol of B1 as a starting material, 0.3mol of potassium tert-butoxide, and 1X 10 under a nitrogen atmosphere-3mol Pd2(dba)3，1×10-3mol P(t-Bu)3Heating 150ml of toluene to 100 ℃, refluxing for 24 hours, sampling a sample, and completely reacting; naturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain an intermediate C1; elemental analysis Structure (molecular formula C)18H13Br2N): theoretical value: c, 53.63; h, 3.25; br, 39.64; n, 3.47; test values are: c, 53.64; h, 3.25; br, 39.64; and N, 3.46. ESI-MS (M/z) (M +): theoretical value 403.117, found value 403.092;
(2) a250 ml three-necked flask was charged with 0.12mol of intermediate C1, 0.1mol of raw material D1, 0.3mol of potassium tert-butoxide, and 1X 10 under a nitrogen atmosphere-3mol Pd2(dba)3，1×10-3mol P(t-Bu)3Heating 150ml of toluene to 105 ℃ for refluxing for 24 hours, sampling a sample, and completely reacting; naturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain an intermediate E1; elemental analysis Structure (molecular formula C)30H23BrN2): theoretical value: c, 73.32; h, 4.72; br, 16.26; n, 5.70; test values are: c, 73.30; h, 4.73; br, 16.27; and N, 5.70. ESI-MS (M/z) (M +): theoretical value 491.432, found value 491.45;
the synthesis of intermediate E is similar to the synthesis of intermediate E-1, and the used raw materials A, B and D are shown in the following table 1:
TABLE 1
The synthesis of intermediate H is as follows:
taking the synthesis example of intermediate H1:
250ml of threeA flask was charged with 0.1mol of F1 as a starting material, 0.12mol of G1 as a starting material, 0.3mol of potassium tert-butoxide, and 1X 10 in a nitrogen atmosphere-3mol Pd2(dba)3，1×10-3mol P(t-Bu)3Heating 150ml of toluene to 105 ℃ for refluxing for 24 hours, sampling a sample, and completely reacting; naturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain an intermediate H1; elemental analysis Structure (molecular formula C)31H21N): theoretical value: c, 91.37; h, 5.19; n, 3.44; test values are: c, 91.38; h, 5.17; and N, 3.45. ESI-MS (M/z) (M +): theoretical value 407.516, found value 407.53;
the synthesis of intermediate H was similar to the synthesis of intermediate H-1, using starting material F and starting material G as shown in Table 2 below:
TABLE 2
Example 1 synthesis of compound 7:
to a 500ml three-necked flask, 0.01mol of intermediate E1, 0.015mol of intermediate H1, 0.03mol of potassium tert-butoxide, 5X 10 in a nitrogen atmosphere-5mol Pd2(dba)3And 5X 10-5mol P(t-Bu)3Then, 150ml of toluene was added to dissolve it, heated to 100 ℃ and refluxed for 24 hours, and the reaction was observed by TLC until the reaction was completed. Naturally cooling to room temperature, filtering, and rotatably evaporating the filtrate until no fraction is obtained. The resulting material was purified over silica gel column (petroleum ether as eluent) to give compound 7 with 99.85% purity and 82.8% yield; elemental analysis Structure (molecular formula C)61H43N3): theoretical value: c, 89.56; h, 5.30; n, 5.14; test values are: c,8957; h, 5.30; and N, 5.13. ESI-MS (M/z) (M +): theoretical value is 818.036, found 818.028.
The reaction involved in the following preparation examples is of the same type as in preparation example 1, and the molar ratio of intermediate E to intermediate H can be adjusted slightly by one skilled in the art using conventional technical means;
example 2 synthesis of compound 18:
compound 18 was prepared as in example 1, except intermediate H2 was used instead of intermediate H1; elemental analysis Structure (molecular formula C)65H47N3): theoretical value: c, 89.73; h, 5.44; n, 4.83; test values are: c, 89.71; h, 5.45; n, 4.84. ESI-MS (M/z) (M +): theoretical value is 870.112, found 870.20.
Example 3 synthesis of compound 33:
compound 33 was prepared as in example 1, except intermediate H3 was used instead of intermediate H1; elemental analysis Structure (molecular formula C)67H47N3): theoretical value: c, 90.00; h, 5.30; n, 4.70; test values are: c, 90.01; h, 5.30; and N, 4.69. ESI-MS (M/z) (M +): theoretical value is 894.134, found 894.07.
Example 4 synthesis of compound 49:
compound 49 was prepared as in example 1, except intermediate E2 was used instead of intermediate E1 and intermediate H4 was used instead of intermediate H1; elemental analysis Structure (molecular formula C)76H57N3): theoretical value: c, 90.17; h, 5.68; n, 4.15; test value: c, 90.18; h, 5.67; and N, 4.15. ESI-MS (M/z) (M +): theoretical value is 1012.313, found 1012.26.
Example 5 synthesis of compound 66:
compound 66 was prepared as in example 1, except intermediate E3 was used instead of intermediate E1 and intermediate H5 was used instead of intermediate H1; elemental analysis Structure (molecular formula C)67H45N3O): theoretical value C, 88.62; h, 4.99; n, 4.63; o, 1.76; test values are: c, 88.62; h, 5.00; n, 4.63; o, 1.75. ESI-MS (M/z) (M +): theoretical value is 908.117, found 908.09.
Example 6 synthesis of compound 80:
Example 7 synthesis of compound 94:
compound 94 was prepared as in example 1, except intermediate E5 was used instead of intermediate E1 and intermediate H6 was used instead of intermediate H1; elemental analysis Structure (molecular formula C)73H51N3): theoretical value C, 90.37; h, 5.30; n, 4.33; test values are: c, 90.36; h, 5.30; n, 4.34. ESI-MS (M/z) (M +): theoretical value is 970.232, found 970.28.
Example 8 synthesis of compound 104:
compound 104 was prepared as in example 1, except intermediate E6 was used instead of intermediate E1; elemental analysis Structure (molecular formula C)66H44N4): theoretical value: c, 88.76; h, 4.97; n, 6.27; test values are: c, 88.77; h, 4.97; and N, 6.26. ESI-MS (M/z) (M +): theoretical value is 893.106, found 893.07.
Example 9 synthesis of compound 115:
compound 115 was prepared as in example 1, except intermediate E7 was used instead of intermediate E1 and intermediate H6 was used instead of intermediate H1; elemental analysis Structure (molecular formula C)71H51N3): theoretical value: c, 90.13; h, 5.43; n, 4.44; test values are: c, 90.12; h, 5.45; n, 4.43. ESI-MS (M/z) (M +): theoretical value is 946.210, found 946.09.
Example 10 synthesis of compound 128:
compound 128 was prepared as in example 1, except intermediate H7 was substituted for intermediate H1; elemental analysis Structure (molecular formula C)66H46N4): theoretical value C, 88.56; h, 5.18; n, 6.26; test values are: c, 88.55; h, 5.18; and N, 6.27. ESI-MS (M/z) (M +): theoretical value is 895.122, found 895.21.
Example 11 synthesis of compound 145:
compound 145 can be prepared as in example 1, except intermediate E8 is substituted for intermediate E1 and intermediate H8 is substituted for intermediate H1; elemental analysis Structure (molecular formula C)69H52N4): theoretical value: c, 88.43; h, 5.59; n, 5.98; test values are: c, 88.44; h, 5.60; and N, 5.96. ESI-MS (M/z) (M +): theoretical value is 937.203, found 937.15.
Example 12 synthesis of compound 159:
compound 159 was prepared as in example 1, except intermediate E9 was substituted for intermediate E1 and intermediate H9 was substituted for intermediate H1; elemental analysis Structure (molecular formula C)75H61N3O): theoretical value: c, 88.29; h, 6.03; n, 4.12; o, 1.57; test values are: c, 88.30; h, 6.03; n, 4.12; o, 1.56. ESI-MS (M/z) (M +): theoretical value is 1020.333, found 1020.25.
Example 13 synthesis of compound 173:
compound 173 was prepared as in example 1, except intermediate H10 was used instead of intermediate H1; elemental analysis Structure (molecular formula C)71H55N3O): theoretical value: c, 88.26; h, 5.74; n, 4.35; o, 1.66; test values are: c, 88.24; h, 5.75; n, 4.35; o, 1.67. ESI-MS (M/z) (M +): theoretical value is 966.241, found 966.25.
Example 14 synthesis of compound 189:
compound 189 is prepared as in example 1, except thatIntermediate E10 replacing intermediate E1, intermediate H4 replacing intermediate H1; elemental analysis Structure (molecular formula C)67H47N3S): theoretical value: c, 86.89; h, 5.12; n, 4.54; s, 3.46; test values are: c, 86.90; h, 5.13; n, 4.53; and S, 3.45. ESI-MS (M/z) (M +): theoretical value is 926.194, found 926.03.
Example 15 synthesis of compound 204:
compound 204 was prepared as in example 1, except intermediate E11 was used instead of intermediate E1; elemental analysis Structure (molecular formula C)67H47N3): theoretical value: c, 90.00; h, 5.30; n, 4.70; test values are: c, 90.01; h, 5.30; and N, 4.69. ESI-MS (M/z) (M +): theoretical value is 894.134, found 894.04.
The organic compound of the present invention is used in a light-emitting device, and can be used as a hole transport/electron blocking layer material. Compounds 7, 18, 33, 49, 66, 80, 94, 104, 115, 128, 145, 159, 167, 173, 184, 189, 200 and 204 of the present invention were tested for T1 energy level, thermal property, HOMO energy level and hole mobility, respectively, and the results of the tests are shown in table 3.
TABLE 3
Note: the triplet energy level T1 was measured by Hitachi F4600 fluorescence spectrometer under the conditions of 2X 10- 5A toluene solution of mol/L; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the thermogravimetric temperature Td is a temperature at which 1% of the weight loss is observed in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate is 20 mL/min; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy testing System (IPS3)Is in an atmospheric environment; hole mobility: the material was fabricated into single charge devices and tested by the SCLC method.
The data in the table show that the organic compound has high glass transition temperature, can improve the phase stability of the material film, and further improves the service life of the device; the high T1 energy level can block the energy loss of the light-emitting layer, thereby improving the light-emitting efficiency of the device; the injection problem of current carriers can be solved by good hole mobility and proper HOMO energy level, and the voltage of the device can be reduced. Therefore, after the organic compound is used for a hole transport layer or an electron blocking layer of an OLED device, the luminous efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.
The following device examples 1 to 23 and device comparative example 1 illustrate in detail the effects of the synthesized compounds of the present invention as materials for a hole transport layer and an electron blocking layer in a device. Compared with the device example 1, the device examples 2 to 23 and the device comparative example 1 have the same manufacturing process, adopt the same substrate material and electrode material, and keep the film thickness of the electrode material consistent, except that the hole transport layer material or the electron blocking layer material in the device is replaced. The device stack structure is shown in table 4, and the performance test results of each device are shown in table 5.
Device example 1
The preparation process comprises the following steps:
as shown in fig. 1, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness of 150nm) is washed, i.e., washed with alkali, washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, HAT-CN having a film thickness of 10nm was deposited by a vacuum deposition apparatus to be used as the hole injection layer 3. Then, compound 7 was evaporated to a thickness of 60nm as the hole transport layer 4. Subsequently, compound EB-1 was evaporated to a thickness of 20nm as an electron blocking layer 5. After the evaporation of the hole transport material is finished, a light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the OLED light emitting device comprises that GH-1 and GH-2 used by the OLED light emitting layer 6 are used as main body materials, GD-1 is used as a doping material, the doping proportion of the doping material is 10% by weight, and the thickness of the light emitting layer is 30 nm. After the light-emitting layer 6, the electron transport layer materials ET-1 and Liq are continuously vacuum-evaporated. The vacuum evaporation film thickness of the material was 30nm, and this layer was a hole-blocking/electron-transporting layer 7. On the hole-blocking/electron-transporting layer 7, a lithium fluoride (LiF) layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this layer was an electron-injecting layer 8. On the electron injection layer 8, a vacuum deposition apparatus was used to produce a 15 nm-thick Mg: an Ag electrode layer, which is used as the cathode layer 9. On the cathode layer 9, 70nm of CP-1 was vacuum-deposited as a CPL layer 10. After the OLED light emitting device was completed as described above, the anode and the cathode were connected by a known driving circuit, and the current efficiency of the device and the lifetime of the device were measured, and the results are shown in table 5.
TABLE 4
The efficiency and lifetime data for each device example and device comparative example 1 are shown in table 5.
TABLE 5
LT97 refers to a current density of 10m/cm2In the case, the time taken for the luminance of the device to decay to 97%; the life test System is an OLED device life tester developed by LTD and having model number of EAS-62C.
As can be seen from the device data results of table 5, the organic light emitting device of the present invention achieves a greater improvement in both efficiency and lifetime over OLED devices of known materials.
Further, the efficiency of the OLED device prepared by the material is stable when the OLED device works at low temperature, the efficiency test is carried out on the device examples 2, 12 and 21 and the device comparative example 1 at the temperature of-10-80 ℃, and the obtained results are shown in the table 6 and the figure 2.
TABLE 6
As can be seen from the data in table 6 and fig. 2, device examples 2, 12, and 21 are device structures in which the material of the present invention and the known material are combined, and compared with device comparative example 1, the efficiency is high at low temperature, and the efficiency is smoothly increased during the temperature increase process.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (5)
1. A compound containing triarylamine and fluorene is characterized in that the specific structure of the compound is as follows:
2. use of a triarylamine and fluorene containing compound as claimed in claim 1 for the preparation of organic electroluminescent devices.
3. An organic electroluminescent element comprising a plurality of organic thin film layers between an anode and a cathode, wherein at least one of the organic thin film layers contains the triarylamine-and fluorene-containing compound according to claim 1.
4. An organic electroluminescent element, characterized in that an electron blocking material or a hole transporting material of the organic electroluminescent element contains the triarylamine-and fluorene-containing compound according to claim 1.
5. A lighting or display element comprising the organic electroluminescent device according to any one of claims 3 or 4.
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| CN114075115A (en) * | 2020-08-20 | 2022-02-22 | 江苏三月科技股份有限公司 | Amine compound and organic electroluminescent device containing same |
| CN114075114A (en) * | 2020-08-20 | 2022-02-22 | 江苏三月科技股份有限公司 | Homogeneous benzene arylamine compound and organic electroluminescent device comprising same |
| CN112300011B (en) * | 2020-10-26 | 2021-11-09 | 长春海谱润斯科技股份有限公司 | Aryl amine derivative containing bifluorene and organic electroluminescent device thereof |
| CN115028539A (en) * | 2021-03-03 | 2022-09-09 | 江苏三月科技股份有限公司 | Arylamine derivative and organic electroluminescent device using same |
| CN116891449A (en) * | 2023-07-28 | 2023-10-17 | 长春海谱润斯科技股份有限公司 | Triamine compound and organic electroluminescent device thereof |
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