CN112552225A - Triarylamine organic compound with carbazole as core and application thereof - Google Patents

Triarylamine organic compound with carbazole as core and application thereof Download PDF

Info

Publication number
CN112552225A
CN112552225A CN201910915847.5A CN201910915847A CN112552225A CN 112552225 A CN112552225 A CN 112552225A CN 201910915847 A CN201910915847 A CN 201910915847A CN 112552225 A CN112552225 A CN 112552225A
Authority
CN
China
Prior art keywords
group
substituted
unsubstituted
organic compound
organic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201910915847.5A
Other languages
Chinese (zh)
Other versions
CN112552225B (en
Inventor
王芳
陆颖
李崇
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiangsu Sunera Technology Co Ltd
Original Assignee
Jiangsu Sunera Technology Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jiangsu Sunera Technology Co Ltd filed Critical Jiangsu Sunera Technology Co Ltd
Priority to CN201910915847.5A priority Critical patent/CN112552225B/en
Publication of CN112552225A publication Critical patent/CN112552225A/en
Application granted granted Critical
Publication of CN112552225B publication Critical patent/CN112552225B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The invention relates to a triarylamine organic compound taking carbazole as a core 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 DDA0002216077200000011
the invention also discloses application of the compound. The compound provided by the invention has a strong electron blocking effect, and the recombination efficiency of excitons in the light-emitting layer is improved; when the material is used as a light-emitting functional layer material of an OLED light-emitting device, the invention is matched withThe branched chains within the range can effectively improve the exciton utilization rate and the radiation efficiency.

Description

Triarylamine organic compound with carbazole as core and application thereof
Technical Field
The invention relates to the technical field of semiconductors, in particular to a triarylamine organic compound taking carbazole as a core 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 a triarylamine organic compound with carbazole as the core and its application. The compound 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 provided by the invention is as follows: a triarylamine organic compound taking carbazole as a core is disclosed, and the structure of the organic compound is shown in a general formula (1):
Figure BDA0002216077180000021
in the general formula (I), L1、L2Each independently represents a single bond, substituted or unsubstituted C6-30Arylene, substituted or unsubstituted C2-30Heteroarylene radical, L1、L2May be the same or different;
the R is1Is represented by substituted or unsubstituted C6-30An aryl group;
the R is2、R3Each independently represents substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C2-C30A heteroaryl group;
by "substituted" is meant that at least one hydrogen atom is replaced by a substituent selected from the group consisting of: deuterium atom, tritium atom, cyano group, halogen atom, C1-C10Alkyl radical, C6-C30Aryl radical, C2-C30One or more heteroaryl groups.
As a further improvement of the invention, R is1Represented as substituted or unsubstitutedNaphthyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzophenanthrenyl.
As a further improvement of the present invention, the general formula (I) may be represented by a structure represented by general formula (I-1) to general formula (I-3):
Figure BDA0002216077180000022
as a further improvement of the invention, L is1、L2Each independently represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted naphthyridine group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranylene group;
the R is2、R3Independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dimethylxanthene group, a substituted or unsubstituted dimethylthioxanthene group;
the substituent of the substitutable group is selected from one or more of deuterium atom, tritium atom, fluorine atom, methoxyl group, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, amyl group, phenyl group, naphthyl group, biphenyl group, phenanthryl group, benzophenanthryl group, pyrenyl group, dimethyl fluorenyl group, diphenyl fluorenyl group, spirofluorenyl group, dibenzofuranyl group, dibenzothienyl group and carbazolyl group.
As a further improvement of the invention, the specific structure of the organic compound is as follows:
Figure BDA0002216077180000031
Figure BDA0002216077180000041
Figure BDA0002216077180000051
Figure BDA0002216077180000061
Figure BDA0002216077180000071
Figure BDA0002216077180000081
Figure BDA0002216077180000091
Figure BDA0002216077180000101
Figure BDA0002216077180000111
Figure BDA0002216077180000121
Figure BDA0002216077180000131
Figure BDA0002216077180000141
the second aspect of the present invention is to provide the use of the above triarylamine-based organic compound with carbazole as the core in the preparation of organic electroluminescent devices.
In a third aspect of the present invention, there is provided an organic electroluminescent device comprising a cathode, an anode and an organic functional layer interposed between the cathode and the anode, wherein the organic functional layer contains the triarylamine-based organic compound having carbazole as a core.
In a fourth aspect of the present invention, there is provided an organic electroluminescent device comprising an electron blocking layer containing the triarylamine-based organic compound having carbazole as a core.
A fifth aspect of the present invention provides a full-color display device including, in order from bottom to top, a substrate, a first electrode, an organic functional material layer, and a second electrode, the organic functional material layer including: a hole transport region over the first electrode; a light emitting layer on the hole transport region, the light emitting layer having a red light emitting layer, a green light emitting layer and a blue light emitting layer patterned in a red pixel region, a green pixel region and a blue pixel region, respectively; an electron transport region over the light emitting layer; the hole transport region sequentially comprises a hole injection layer, a hole transport layer and a hole transport auxiliary layer from bottom to top, the hole injection layer comprises a P-type doping material, the red pixel unit, the green pixel unit and the blue pixel unit share the hole injection layer and the hole transport layer and respectively comprise the hole transport auxiliary layer, and the hole transport region comprises the triarylamine organic compound which takes carbazole as a core and is shown in a general formula (I).
A sixth aspect of the present invention is to provide a lighting or display element having such features, including the organic electroluminescent device described above.
Compared with the prior art, the invention has the beneficial technical effects that:
(1) the compound takes carbazole as a core, the LUMO energy level can be properly adjusted, the function of electron blocking is achieved, and the recombination efficiency of excitons in a light-emitting layer is improved; meanwhile, the singlet energy level (T1) of the compound can be improved, the TTA effect (singlet annihilation, so that one molecule is in an excited singlet state) is increased, the exciton utilization rate 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. The compound has good application effect in OLED luminescent devices and good industrialization prospect.
(2) 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.
(3) The structure of the compound contains a carbazole structure, so that the compound has a wider band gap, and the compound is ensured to be free of absorption in the field of visible light; in addition, the distance between molecules is increased, the interaction force between molecules is weakened, so that the evaporation temperature is low, and the industrial processing window of the material is widened.
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 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 layer, and 10 is a CPL layer.
Detailed Description
Example 1: synthesis of intermediate B1:
Figure BDA0002216077180000151
adding 0.01mol of raw material 1-1, 0.012mol of raw material 2-1, 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 5X 10-5molPd2(dba)3，5×10-5mol P(t-Bu)3Heating 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 24 hours, and sampling a sample point plate to complete the reaction; naturally cooling to room temperature, filtering, carrying out rotary evaporation on the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain a target product intermediate B1; HPLC purity 99.37%, yield 73.4%; elemental analysis Structure (molecular formula C)34H23NO): theoretical value C, 88.48; h, 5.02; n, 3.03; test values are: c, 88.45; h, 5.01; and N, 3.01. ESI-MS (M/z) (M +): theoretical value is 461.18, found 461.21.
The intermediates B required in the examples are synthesized as shown in table 1:
TABLE 1
Figure BDA0002216077180000152
Figure BDA0002216077180000161
Figure BDA0002216077180000171
Example 2: synthesis of intermediate C1:
Figure BDA0002216077180000172
in a nitrogen atmosphere, 0.01mol of 3-1 of the raw material, 0.025mol of 4-1 of the raw material, 0.03mol of sodium tert-butoxide, 5X 10-5mol Pd2(dba)3And 5X 10-5mol of tri-tert-butylphosphine, dissolving in 150ml of toluene, heating to 100 deg.C, refluxing for 24 hours, and observing the reaction by TLC until the reaction is completeAnd (4) completing. Naturally cooling to room temperature, filtering, and rotatably evaporating the filtrate until no fraction is obtained. The resulting material was purified by column on silica gel (petroleum ether as eluent) to give intermediate C-1. HPLC purity 98.18%, yield 82.6%; elemental analysis Structure (C)34H20BrN) theoretical value: c, 78.17; h, 3.86; br, 15.29; n, 2.68; test values are: c, 78.17; h, 3.86; br, 15.29; and N, 2.68. ESI-MS (M/z) (M +): the molecular weight of the material is 521.08, and the measured molecular weight is 521.27.
The intermediates C required in the examples are synthesized as shown in table 2:
TABLE 2
Figure BDA0002216077180000181
Example 3: synthesis of compound 14:
Figure BDA0002216077180000191
adding 0.01mol of intermediate B1, 0.012mol of intermediate C1 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 5X 10-5molPd2(dba)3，5×10-5mol P(t-Bu)3Heating 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 24 hours, and sampling a sample point plate to complete the reaction; naturally cooling to room temperature, filtering, rotatably evaporating the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain the target product with the HPLC purity of 99.63 percent and the yield of 79.4 percent. Elemental analysis Structure (molecular formula C)68H42N2O): theoretical value C, 90.44; h, 4.69; n, 3.10; test value C, 90.47; h, 4.65; and N, 3.12. ESI-MS (M/z) (M +): calculated 902.33, found 902.39.1H NMR(500MHz,Chloroform-d)δ8.22(dt,1H),8.17–8.10(m,2H),8.06–7.94(m,8H),7.87–7.76(m,3H),7.76(dt,1H),7.69(d,1H),7.67–7.53(m,9H),7.53–7.37(m,7H),7.37–7.31(m,1H),7.31–7.23(m,4H),7.23–7.11(m,5H).
The preparation of examples 4-22 was similar to that of example 3, and the specific structures of intermediate B, intermediate C and the product used in this example, as well as the structural characterization of the final product, are shown in tables 3a and 3B.
TABLE 3a
Figure BDA0002216077180000192
Figure BDA0002216077180000201
Figure BDA0002216077180000211
Figure BDA0002216077180000221
TABLE 3b
Figure BDA0002216077180000222
Figure BDA0002216077180000231
The compound of the invention is used in a light-emitting device and can 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, HOMO energy level and hole mobility, respectively, and the test results are shown in table 4:
TABLE 4
Figure BDA0002216077180000241
Note: the triplet energy level T1 was measured by Fluorolog-3 series fluorescence spectrometer from Horiba under the conditions of 2 x 10-5A toluene solution of mol/L; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC,DSC204F1 differential scanning calorimeter of German Nachi company), and 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 is tested by an ionization energy testing system (IPS-3), and the test is a nitrogen environment; eg is tested by a double-beam ultraviolet-visible spectrophotometer (model: TU-1901); and (3) testing hole mobility, namely preparing the material into a single-charge device and measuring by using an SCLC (liquid crystal display cell) method.
The data in the table show that the organic compound has a proper HOMO energy level and can be applied to an electron blocking layer, and the organic compound has high hole mobility and high thermal stability, so that the efficiency and the service life of the 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 1-20 and device comparative example 1. Compared with the device comparative example 1, the device examples 1 to 20 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 material of the electron blocking layer in the device is replaced.
Device comparative example 1
The preparation process comprises the following steps:
as shown in fig. 1, the anode layer 2(ITO (15nm)/Ag (150nm)/ITO (15nm)) is washed, that is, 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 anode layer 1. HT-1 and P-1 having a film thickness of 10nm were deposited on the anode layer 2 after the above washing as the hole injection layer 3 by a vacuum deposition apparatus, and the mass ratio of HT-1 to P-1 was 97: 3. Next, HT-1 was evaporated to a thickness of 130nm as a hole transport layer 4. EB-1 was then evaporated to a thickness of 10nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, the light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the OLED light emitting device comprises that BH-1 used by the OLED light emitting layer 6 is used as a main material, BD-1 is used as a doping material, the doping proportion of the doping material is 3% by weight, and the thickness of the light emitting layer is 20 nm. After the light-emitting layer 6, ET-1 and Liq are continuously evaporated, wherein the mass ratio of ET-1 to Liq is 1: 1. The vacuum-deposited film thickness of this material was 35nm, and this layer was a hole-blocking/electron-transporting layer 7. On the hole-blocking/electron-transporting layer 7, a Yb layer having a film thickness of 1nm, which is an electron-injecting layer 8, was formed by a vacuum evaporation apparatus. On the electron injection layer 8, a vacuum deposition apparatus was used to produce a 15 nm-thick Mg: the Ag electrode layer has a Mg/Ag mass ratio of 1:9, and is used as 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 BDA0002216077180000251
Figure BDA0002216077180000261
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. Specific structures of device examples 1 to 20 and device comparative example 2 prepared in the same manner are shown in table 5; the results of the current efficiency, voltage and lifetime tests of the resulting devices are shown in table 6.
TABLE 5
Figure BDA0002216077180000262
Figure BDA0002216077180000271
TABLE 6
Figure BDA0002216077180000272
Figure BDA0002216077180000281
Note: voltage, current efficiency and color coordinates were measured using an IVL (Current-Voltage-Brightness) test System (Fushda scientific instruments, Suzhou) at a current density of 10mA/cm2(ii) a The life test system is an EAS-62C type OLED device life tester of Japan System research company; LT95 refers to the time it takes for the device luminance to decay to 95% at a particular luminance (blue: 1000 nits).
It can be seen from the device data results that the organic light emitting device of the present invention achieves a greater improvement in both efficiency and lifetime compared to the device comparative example over the OLED device of known materials.

Claims (8)

1. A triarylamine organic compound with carbazole as a core is characterized in that the structure of the organic compound is shown as a general formula (1):
Figure FDA0002216077170000011
in the general formula (I), L1、L2Each independently represents a single bond, substituted or unsubstituted C6-30Arylene, substituted or unsubstituted C2-30Heteroarylene radical, L1、L2May be the same or different;
the R is1Is represented by substituted or unsubstituted C6-30An aryl group;
the R is2、R3Each independently represents substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C2-C30A heteroaryl group;
by "substituted" is meant that at least one hydrogen atom is replaced by a substituent selected from the group consisting of: deuterium atom, tritium atom, cyano group, halogen atom, C1-C10Alkyl radical, C6-C30Aryl radical, C2-C30One or more heteroaryl groups.
2. The organic compound of claim 1, wherein R is1Represented by a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted benzophenanthrenyl group.
3. The organic compound according to claim 1, wherein the general formula (I) can be represented by a structure represented by general formula (I-1) to general formula (I-3):
Figure FDA0002216077170000012
4. the organic compound of claim 1 or 2, wherein L is1、L2Each independently represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted naphthyridine group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranylene group;
the R is2、R3Independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dimethylxanthene group, a substituted or unsubstituted dimethylthioxanthene group;
the substituent of the substitutable group is selected from one or more of deuterium atom, tritium atom, fluorine atom, methoxyl group, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, amyl group, phenyl group, naphthyl group, biphenyl group, phenanthryl group, benzophenanthryl group, pyrenyl group, dimethyl fluorenyl group, diphenyl fluorenyl group, spirofluorenyl group, dibenzofuranyl group, dibenzothienyl group and carbazolyl group.
5. The organic compound of claim 1, wherein the organic compound has the specific structure:
Figure FDA0002216077170000021
Figure FDA0002216077170000031
Figure FDA0002216077170000041
Figure FDA0002216077170000051
Figure FDA0002216077170000061
Figure FDA0002216077170000071
Figure FDA0002216077170000081
Figure FDA0002216077170000091
Figure FDA0002216077170000101
Figure FDA0002216077170000111
Figure FDA0002216077170000121
Figure FDA0002216077170000131
6. an organic electroluminescent device comprises a cathode, an anode and an organic functional layer, wherein the organic functional layer is positioned between the cathode and the anode, and is characterized in that at least one organic functional layer of the organic electroluminescent device contains the triarylamine organic compound which takes carbazole as a core in any one of claims 1 to 5.
7. The organic electroluminescent device according to claim 6, wherein the organic functional layer comprises an electron blocking layer, and the electron blocking layer comprises the triarylamine-based organic compound having carbazole as a core according to any one of claims 1 to 5.
8. A lighting or display element comprising the organic electroluminescent device according to any one of claims 6 or 7.
CN201910915847.5A 2019-09-26 2019-09-26 Triarylamine organic compound with carbazole as core and application thereof Active CN112552225B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201910915847.5A CN112552225B (en) 2019-09-26 2019-09-26 Triarylamine organic compound with carbazole as core and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201910915847.5A CN112552225B (en) 2019-09-26 2019-09-26 Triarylamine organic compound with carbazole as core and application thereof

Publications (2)

Publication Number Publication Date
CN112552225A true CN112552225A (en) 2021-03-26
CN112552225B CN112552225B (en) 2023-09-05

Family

ID=75029840

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910915847.5A Active CN112552225B (en) 2019-09-26 2019-09-26 Triarylamine organic compound with carbazole as core and application thereof

Country Status (1)

Country Link
CN (1) CN112552225B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113861043A (en) * 2020-06-30 2021-12-31 北京鼎材科技有限公司 Compound and application thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150022461A (en) * 2013-08-23 2015-03-04 에스케이케미칼주식회사 Compound for organic electroluminescent device and organic electroluminescent device comprising the same
CN109942439A (en) * 2019-04-09 2019-06-28 江苏三月光电科技有限公司 A kind of tri-arylamine group organic compound and its application
CN110386894A (en) * 2018-04-20 2019-10-29 北京鼎材科技有限公司 A kind of hole mobile material and its application
CN110577510A (en) * 2018-06-07 2019-12-17 江苏三月光电科技有限公司 Compound based on bis-dimethyl fluorene substituted aniline and organic electroluminescent device prepared from compound
CN110577511A (en) * 2018-06-07 2019-12-17 江苏三月光电科技有限公司 Compound with triarylamine structure as core and preparation method thereof
CN111362810A (en) * 2018-12-26 2020-07-03 江苏三月光电科技有限公司 Compound containing dibenzosuberene and application thereof in organic electroluminescent device

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150022461A (en) * 2013-08-23 2015-03-04 에스케이케미칼주식회사 Compound for organic electroluminescent device and organic electroluminescent device comprising the same
CN110386894A (en) * 2018-04-20 2019-10-29 北京鼎材科技有限公司 A kind of hole mobile material and its application
CN110577510A (en) * 2018-06-07 2019-12-17 江苏三月光电科技有限公司 Compound based on bis-dimethyl fluorene substituted aniline and organic electroluminescent device prepared from compound
CN110577511A (en) * 2018-06-07 2019-12-17 江苏三月光电科技有限公司 Compound with triarylamine structure as core and preparation method thereof
CN111362810A (en) * 2018-12-26 2020-07-03 江苏三月光电科技有限公司 Compound containing dibenzosuberene and application thereof in organic electroluminescent device
CN109942439A (en) * 2019-04-09 2019-06-28 江苏三月光电科技有限公司 A kind of tri-arylamine group organic compound and its application

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113861043A (en) * 2020-06-30 2021-12-31 北京鼎材科技有限公司 Compound and application thereof

Also Published As

Publication number Publication date
CN112552225B (en) 2023-09-05

Similar Documents

Publication Publication Date Title
CN111662258A (en) Organic compound containing pyrene and application thereof in OLED
CN111662259A (en) Organic compound containing pyrene and application thereof in organic electroluminescent device
CN111662187A (en) Amino-containing organic compound and application thereof
CN113004259B (en) Compound with anthrone skeleton as core and application thereof
CN111662190A (en) Organic compound containing pyrene or aza-pyrene and application thereof
CN110577488A (en) Compound with carbazole as core and application thereof in organic electroluminescent device
CN111943857B (en) Triarylamine organic compound and application thereof
CN113135903A (en) Aromatic dibenzofuran derivative and application thereof
CN112479903A (en) Organic compound with mesitylene as core and application thereof
CN113135928A (en) Organic compound and organic electroluminescent device comprising same
CN110642732B (en) Organic compound containing spirofluorene anthrone structure and application thereof
CN110577523B (en) Compound containing triarylamine structure and organic electroluminescent device prepared from compound
CN112479978A (en) Organic compound with carbazole derivative as core and application thereof
CN111362947A (en) Benzimidazole-containing organic compound and application thereof
CN111362936A (en) Compound with olefinic bond-containing seven-membered ring as core and application thereof
CN110963904A (en) Compound with ketone and fluorene as cores, preparation method and application thereof
CN112479904B (en) Organic compound with indeno-anthracene derivative as core and application thereof
CN114685464A (en) Compound containing triazine structure and application thereof
CN114105868A (en) Organic compound with 4-cyanopyridine as core and organic electroluminescent device comprising same
CN112552225B (en) Triarylamine organic compound with carbazole as core and application thereof
CN111362955A (en) Organic compound and application thereof to OLED device
CN111362959A (en) Compound with olefinic bond-containing fluorene as core and application thereof
CN114057660B (en) Compound containing bis-triazine structure and application thereof
CN113004298B (en) Anthracene ketone five-membered ring organic compound and application thereof
CN112479905B (en) Organic compound containing benzoanthracene fluorene and diarylamine and application thereof in organic electroluminescent device

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
CB02 Change of applicant information

Address after: B312-194, No. 2 Fengwei Road, Huizhi Enterprise Center, Xishan Economic and Technological Development Zone, Xishan District, Wuxi City, Jiangsu Province, 214000

Applicant after: Jiangsu March Technology Co.,Ltd.

Address before: 214112 No.210 Xinzhou Road, New District, Wuxi City, Jiangsu Province

Applicant before: JIANGSU SUNERA TECHNOLOGY Co.,Ltd.

CB02 Change of applicant information
GR01 Patent grant
GR01 Patent grant