CN111662190A - Organic compound containing pyrene or aza-pyrene and application thereof - Google Patents

Organic compound containing pyrene or aza-pyrene and application thereof Download PDF

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CN111662190A
CN111662190A CN201910178213.6A CN201910178213A CN111662190A CN 111662190 A CN111662190 A CN 111662190A CN 201910178213 A CN201910178213 A CN 201910178213A CN 111662190 A CN111662190 A CN 111662190A
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pyrene
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赵四杰
唐丹丹
谢丹丹
吴秀芹
王芳
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Jiangsu Sunera Technology Co Ltd
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Jiangsu Sunera Technology Co Ltd
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Abstract

The invention relates to an organic compound containing pyrene or aza-pyrene and application thereof, belonging to the technical field of semiconductors, and the structure of the compound provided by the invention is shown as a general formula (I):
Figure DDA0001989984340000011
the invention also discloses application of the compound. The organic compound provided by the invention has stronger hole transmission capability, and under the appropriate 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; when the organic light emitting diode is used as a light emitting functional layer material of an OLED light emitting device, the exciton utilization rate and the radiation efficiency can be effectively improved by matching the branched chain in the range of the invention.

Description

Organic compound containing pyrene or aza-pyrene and application thereof
Technical Field
The invention relates to the technical field of semiconductors, in particular to an organic compound containing pyrene or aza-pyrene and application thereof.
Background
At present, the OLED display technology has been applied in the fields of smart phones, tablet computers, and the like, and will further expand to large-size application fields such as televisions, but compared with actual product application requirements, the light emitting efficiency, the service life, and other performances of the OLED device need to be further improved. The research on the improvement of the performance of the OLED light emitting device 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 OLED photoelectric functional material are needed 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 broad categories from the application, i.e., charge injection transport materials and light emitting materials, and further, the charge injection transport materials can be further divided into electron injection transport materials, electron blocking materials, hole injection transport materials and hole blocking materials, and the light emitting materials can be further divided into main light emitting materials and doping materials.
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, and as a host material of a light-emitting layer, a material having good bipolar property, appropriate HOMO/LUMO energy level, etc. is required.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, and the OLED device structure applied in industry comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport 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 transport material, a light emitting material, an electron transport 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 materials have stronger selectivity, and the performance of the same materials in the devices with different structures can also be completely different.
Therefore, aiming at the industrial application requirements of the current OLED device, different functional film layers of the OLED device and the photoelectric characteristic requirements of the device, a more suitable OLED functional material or material combination with high 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 illumination industry, the development of the current OLED material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and the development of organic functional materials with higher performance is very important as a material enterprise.
Disclosure of Invention
In view of the above problems in the prior art, the present applicant provides an organic compound containing pyrene or aza-pyrene and its application. The compound takes triarylamine containing pyrene or aza-pyrene as a core, 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.
The technical scheme of the invention is as follows: an organic compound containing pyrene or azapyrene, the structure of the compound is shown as the general formula (I):
Figure BDA0001989984320000021
in the general formula (I), n represents 0 or 1;
said L1、L2、L3Each independently represents a single bond, phenylene, biphenylene, naphthylene, pyridylene or naphthyridinylene;
ar is1Represents a hydrogen atom, a phenyl group, a naphthyl group, a pyrimidinyl group or a naphthyridinyl group;
ar is2Is represented by substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 5 to 30 membered heteroaryl containing one or more heteroatoms;
x represents an oxygen atom, a sulfur atom, -C (R)1)(R2) -or-N (R)3) -; wherein R is1～R3Each independently is represented by C1-10Alkyl, substituted or unsubstituted C6-30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms; r1And R2May be bonded to each other to form a ring;
each occurrence of Z, which is the same or different, is represented by a nitrogen atom or C-R; wherein, with the group L3The bonded Z represents a carbon atom;
r represents hydrogen atom, deuterium atom, tritium atom, cyano, halogen, C1-10Alkyl of (C)2-10Alkenyl of (a), substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 5-to 30-membered heteroaryl containing one or more heteroatoms, between adjacent RCan be bonded to each other to form a ring;
the substituent of the substitutable group is selected from cyano, halogen atom, C1-10Alkyl of (C)6-30One or more of aryl, 5-to 30-membered heteroaryl containing one or more heteroatoms;
the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
As a further improvement of the present invention, the general formula (I) may be represented by structures represented by general formula (I-1) and general formula (I-2):
Figure BDA0001989984320000031
as a further improvement of the invention, R is1～R3Each independently represents one of methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, pentyl, hexyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl and substituted or unsubstituted pyridyl;
r represents a hydrogen atom, a deuterium atom, a tritium atom, a cyano group, a fluorine atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyclohexyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted naphthyridinyl group;
ar is2Represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted azaspirofluorenyl group, a substituted or unsubstituted benzodimethylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted carbazolinyl group;
the substituent of the substitutable group is selected from one or more of cyano, fluorine atom, methyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, dimethyl fluorenyl, diphenyl fluorenyl, spirofluorenyl, dibenzofuranyl, carbazolyl, dibenzothienyl, pyridyl, naphthyridinyl or carbazolinyl.
As a further improvement of the invention, the compound has a specific structure as follows:
Figure BDA0001989984320000032
Figure BDA0001989984320000041
Figure BDA0001989984320000051
Figure BDA0001989984320000061
Figure BDA0001989984320000071
Figure BDA0001989984320000081
Figure BDA0001989984320000091
Figure BDA0001989984320000101
Figure BDA0001989984320000111
Figure BDA0001989984320000121
Figure BDA0001989984320000131
Figure BDA0001989984320000141
Figure BDA0001989984320000151
Figure BDA0001989984320000161
Figure BDA0001989984320000171
Figure BDA0001989984320000181
Figure BDA0001989984320000191
Figure BDA0001989984320000201
Figure BDA0001989984320000211
Figure BDA0001989984320000221
Figure BDA0001989984320000231
Figure BDA0001989984320000241
Figure BDA0001989984320000251
Figure BDA0001989984320000261
at least one functional layer of the organic electroluminescent device contains the organic compound containing pyrene or aza-pyrene.
As a further improvement of the invention, the organic electroluminescent device comprises a hole transport layer or an electron blocking layer, and the hole transport layer or the electron blocking layer contains the organic compound containing pyrene or aza-pyrene.
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 of the invention takes triarylamine containing pyrene or aza-pyrene as a core, is connected with an electron-donating group, has higher hole mobility, and can improve the recombination efficiency of excitons in a light-emitting layer and the energy utilization rate as the material of a hole transport layer of an OLED light-emitting device, thereby improving the light-emitting efficiency of the device.
(2) 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; can effectively improve the exciton utilization rate, reduce the voltage of the device, improve the current efficiency of the device and prolong the service life 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;
wherein, 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 luminescent layer, 7 is an electron transport or hole blocking layer, 8 is an electron injection layer, 9 is a cathode reflection electrode layer, and 10 is a light extraction layer.
FIG. 2 shows the current efficiencies of the OLED devices of the embodiment of the present invention and the OLED device of the comparative example 1 at the temperature range of-10 to 80 ℃.
FIG. 3 is a UV absorption spectrum of inventive compound 321;
FIG. 4 is a UV absorption spectrum of compound 379 of the present invention;
FIG. 5 is a UV absorption spectrum of inventive compound 913;
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.
L used below1、L2、L3、Ar1、Ar2The symbols X, Z and n have the same meaning as in the summary of the invention.
When not simultaneously satisfying L1Is a single bond, L2And (3) synthesizing an intermediate N when N is a single bond and 0:
Figure BDA0001989984320000271
(1) 0.01mol of the starting material A was dissolved in 150ml of Tetrahydrofuran (THF) under a nitrogen atmosphere, and 0.03mol of bis (pinacolato) diboron and 1 × 10 were added-4Adding mol (1, 1' -bis (diphenylphosphino) ferrocene) dichloropalladium (II) and 0.03mol of potassium acetate, stirring the mixture, and heating and refluxing the mixed solution of the reactants at the reaction temperature of 80 ℃ for 10 hours; after the reaction is finished, adding water for cooling, filtering the mixture, putting a filter cake in a vacuum drying oven for drying, and separating and purifying the obtained residue through a silica gel column to obtain an intermediate M;
(2) adding 0.01mol of intermediate M, 0.015mol of raw material B and 1 × 10 in a 250ml three-neck bottle under the protection of nitrogen-4molPd(PPh3)4100mL of toluene and 50mL of ethanol were mixed with stirring, and 0.03mol of carbon was addedDissolving sodium carbonate in 50mL of water, adding a sodium carbonate aqueous solution into a reaction system, heating to 110 ℃, carrying out reflux reaction for 24 hours, and sampling a sample point plate to show that no intermediate M remains and the reaction is complete; naturally cooling to room temperature, filtering, layering filtrate, taking an organic phase, performing reduced pressure rotary evaporation (-0.09MPa, 85 ℃), and purifying by a neutral silica gel column to obtain an intermediate N;
the intermediate N is prepared by the synthesis method, and the specific structure is shown in Table 1.
TABLE 1
Figure BDA0001989984320000281
Figure BDA0001989984320000291
Figure BDA0001989984320000301
Synthesis of target compound:
Figure BDA0001989984320000302
adding 0.01mol of intermediate N or raw material A, 0.012mol of raw material C and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, then adding 0.03mol of sodium tert-butoxide, 1 × 10-4molPd2(dba)3，1×10-4Heating the mol tri-tert-butylphosphine to 110 ℃, carrying out reflux reaction for 24 hours, sampling a point plate, and indicating that no intermediate N or raw material A remains, wherein the reaction is complete; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate (0.09 MPa, 85 ℃), and purifying by a neutral silica gel column to obtain a target product;
the target compounds were prepared by the above synthesis methods, and the specific structures are shown in table 2.
TABLE 2
Figure BDA0001989984320000303
Figure BDA0001989984320000311
Figure BDA0001989984320000321
Figure BDA0001989984320000331
Figure BDA0001989984320000341
Figure BDA0001989984320000351
The compound of the invention is used in a luminescent device, can be used as a hole transport layer material, and can also be used as an electron blocking layer material. The compounds prepared in the above examples of the present invention were tested for thermal performance, T1 energy level, Eg, HOMO energy level and hole mobility, respectively, and the test results are shown in table 3:
TABLE 3
Figure BDA0001989984320000352
Figure BDA0001989984320000361
Note: the triplet energy level T1 was measured by Hitachi F4600 fluorescence spectrometer under the conditions of 2X 10- 5A toluene solution of mol/mL; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the highest occupied molecular orbital HOMO energy level is tested by an ionization energy testing system (IPS-3), and the test is in an atmospheric environment; the thermal weight loss temperature Td is a temperature at which 1% weight loss is achieved in a nitrogen atmosphere, and is TGA-50 of Shimadzu corporation, JapanMeasuring on an H thermogravimetric analyzer, wherein the nitrogen flow is 20 mL/min; testing hole mobility, namely preparing the material into a single-charge device, and measuring by using an SCLC method; using Gaussian16, 6-31G (d) basis set, B3lyp functional and TD-FDT algorithm to optimize the geometrical structure, and calculating the energy levels of HOMO and LUMO, wherein Eg is | HOMO-LUMO |; eg was measured by uv spectroscopy.
The data in the table show that the organic compound has a proper HOMO energy level and can be applied to a hole transport layer or an electron blocking layer, and the organic compound taking triarylamine containing pyrene or azapyrene as a core has high hole mobility and high thermal stability, so that the efficiency and the service life of the manufactured OLED device containing the organic compound are improved.
The application effect of the synthesized OLED material of the present invention in the device is detailed by device examples 1-30 and device comparative example 1. Compared with the device embodiment 1, the device embodiments 2 to 30 and the device comparative example 1 of the present invention have the same manufacturing process, and adopt the same substrate material and electrode material, and the film thickness of the electrode material is also kept consistent, except that the hole transport layer material or the electron blocking layer material in the device is replaced.
Device example 1
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 6 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 light emitting layer 6 comprises GH-1 and GH-2 used by the OLED light emitting layer 6 as main materials, GD-1 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 40 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 40nm, 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, this layer being the cathode layer 9. On the cathode layer 9, 70nm of CP-1 was vacuum-deposited as a CPL layer 10. The molecular structural formula of the related material is shown as follows:
Figure BDA0001989984320000371
after the OLED light emitting device was completed as described above, the anode and cathode were connected by a known driving circuit, and the current efficiency, the light emission spectrum, and the lifetime of the device were measured. Device examples and comparative examples prepared in the same manner are shown in table 4; current efficiency, color and 10mA/cm of the resulting device2The results of the LT97 lifetime test at current are shown in table 5. Efficiency attenuation coefficient of the resulting device
Figure BDA0001989984320000373
The test results of (2) are shown in Table 6. The current efficiency test results of the obtained device at the temperature range of-10 to 80 ℃ are shown in Table 7.
TABLE 4
Figure BDA0001989984320000372
Figure BDA0001989984320000381
Figure BDA0001989984320000391
TABLE 5
Figure BDA0001989984320000392
Figure BDA0001989984320000401
Note: LT97 refers to a current density of 10mA/cm2In the case, the time taken for the luminance of the device to decay to 97%;
the life test system is a Korean pulse science M600 type OLED device life tester.
As can be seen from the device data results in table 5, compared with comparative device 1, the organic light emitting device of the present invention has a greater improvement in both efficiency and lifetime compared to the OLED device of the known material.
In order to compare the efficiency attenuation conditions of different devices under high current density, the efficiency attenuation coefficient is defined
Figure BDA0001989984320000403
It is shown that the drive current is 100mA/cm2The ratio between the difference between the maximum efficiency μ 100 of the device and the maximum efficiency μm of the device and the maximum efficiency,
Figure BDA0001989984320000404
the larger the value, the more serious the efficiency roll-off of the device is, and conversely, the problem that the device rapidly decays under high current density is controlled. The efficiency attenuation coefficients were respectively applied to the device examples 1 to 30 and the device comparative example 1
Figure BDA0001989984320000405
The measurement results are shown in table 6:
TABLE 6
Figure BDA0001989984320000402
Figure BDA0001989984320000411
From the data in table 6, it can be seen from the comparison of the efficiency roll-off coefficients of the examples and the comparative examples that the organic light emitting device of the present invention can effectively reduce the efficiency roll-off.
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 6, 22 and 26 and the device comparative example 1 at the temperature of-10-80 ℃, and the obtained results are shown in the table 7 and the figure 2.
TABLE 7
Figure BDA0001989984320000412
As can be seen from the data in table 7 and fig. 2, device examples 6, 22 and 26 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.

Claims (7)

1. An organic compound containing pyrene or azapyrene, characterized in that the structure of the compound is shown in general formula (I):
Figure FDA0001989984310000011
in the general formula (I), n represents 0 or 1;
said L1、L2、L3Each independently represents a single bond, phenylene, biphenylene, naphthylene, pyridylene or naphthyridinylene;
ar is1Represents a hydrogen atom, a phenyl group, a naphthyl group, a pyrimidinyl group or a naphthyridinyl group;
ar is2Is represented by substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 5 to 30 membered heteroaryl containing one or more heteroatoms;
x represents an oxygen atom, a sulfur atom, -C (R)1)(R2) -or-N (R)3) -; wherein R is1～R3Each independently is represented by C1-10Alkyl, substituted or unsubstituted C6-30Aryl, substituted or unsubstituted, containing one or moreOne of 5-30 membered heteroaryl of a heteroatom; r1And R2May be bonded to each other to form a ring;
each occurrence of Z, which is the same or different, is represented by a nitrogen atom or C-R; wherein, with the group L3The bonded Z represents a carbon atom;
r represents hydrogen atom, deuterium atom, tritium atom, cyano, halogen, C1-10Alkyl of (C)2-10Alkenyl of (a), substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 5-to 30-membered heteroaryl containing one or more heteroatoms, adjacent R's may be bonded to each other to form a ring;
the substituent of the substitutable group is selected from cyano, halogen atom, C1-10Alkyl of (C)6-30One or more of aryl, 5-to 30-membered heteroaryl containing one or more heteroatoms;
the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
2. The organic compound according to claim 1, wherein the general formula (I) can be represented by structures represented by general formulae (I-1) and (I-2):
Figure FDA0001989984310000021
3. the organic compound of claim 1, wherein R is1～R3Each independently represents one of methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, pentyl, hexyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl and substituted or unsubstituted pyridyl;
r represents a hydrogen atom, a deuterium atom, a tritium atom, a cyano group, a fluorine atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyclohexyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted naphthyridinyl group;
ar is2Represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted azaspirofluorenyl group, a substituted or unsubstituted benzodimethylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted carbazolinyl group;
the substituent of the substitutable group is selected from one or more of cyano, fluorine atom, methyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, dimethyl fluorenyl, diphenyl fluorenyl, spirofluorenyl, dibenzofuranyl, carbazolyl, dibenzothienyl, pyridyl, naphthyridinyl or carbazolinyl.
4. The organic compound of any one of claims 1-3, wherein the compound has the specific structure:
Figure FDA0001989984310000022
Figure FDA0001989984310000031
Figure FDA0001989984310000041
Figure FDA0001989984310000051
Figure FDA0001989984310000061
Figure FDA0001989984310000071
Figure FDA0001989984310000081
Figure FDA0001989984310000091
Figure FDA0001989984310000101
Figure FDA0001989984310000111
Figure FDA0001989984310000121
Figure FDA0001989984310000131
Figure FDA0001989984310000141
Figure FDA0001989984310000151
Figure FDA0001989984310000161
Figure FDA0001989984310000171
Figure FDA0001989984310000181
Figure FDA0001989984310000191
Figure FDA0001989984310000201
Figure FDA0001989984310000211
Figure FDA0001989984310000221
Figure FDA0001989984310000231
Figure FDA0001989984310000241
Figure FDA0001989984310000251
5. an organic electroluminescent element, characterized in that at least one functional layer of the organic electroluminescent element contains the pyrene-or azapyrene-containing organic compound according to any one of claims 1 to 4.
6. The organic electroluminescent device according to claim 5, comprising a hole transport layer or an electron blocking layer, wherein the hole transport layer or the electron blocking layer contains the pyrene-or azapyrene-containing organic compound according to any one of claims 1 to 4.
7. A lighting or display element comprising the organic electroluminescent device according to any one of claims 5 or 6.
CN201910178213.6A 2019-03-08 2019-03-08 Organic compound containing pyrene or aza-pyrene and application thereof Pending CN111662190A (en)

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