WO2018033086A1 - Composé substitué par un noyau dibenzo à six chaînons comprenant du xanthone comme noyau et ses applications - Google Patents

Composé substitué par un noyau dibenzo à six chaînons comprenant du xanthone comme noyau et ses applications Download PDF

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WO2018033086A1
WO2018033086A1 PCT/CN2017/097614 CN2017097614W WO2018033086A1 WO 2018033086 A1 WO2018033086 A1 WO 2018033086A1 CN 2017097614 W CN2017097614 W CN 2017097614W WO 2018033086 A1 WO2018033086 A1 WO 2018033086A1
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group
compound
xanthone
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substituted
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徐凯
陈棪
李崇
张兆超
叶中华
张小庆
王立春
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江苏三月光电科技有限公司
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Definitions

  • the present invention relates to the field of semiconductor technology, and in particular to a xanthone-based compound and its use as an luminescent layer material on an organic light emitting diode.
  • OLED Organic Light Emitting Diodes
  • OLED displays have self-luminous, wide viewing angle (above 175°), short reaction time, high luminous efficiency, and wide color. Domain, low operating voltage (3 ⁇ 10V), thin panel (less than 1mm) and can be curled.
  • OLED is hailed as a star flat display product in the 21st century. As the technology matures, it is likely to develop rapidly in the future, and the future is boundless.
  • OLED luminescence is that after applying an applied voltage, holes and electrons overcome the interface energy barrier, and are injected by the anode and the cathode, respectively entering the HOMO energy level of the hole transport layer and the LUMO energy level of the electron transport layer; and the post charge is added.
  • the electric field is driven to the interface between the hole transport layer and the electron transport layer, and the energy level difference of the interface causes the interface to accumulate charges; the electrons and holes recombine in the organic substance having the luminescent property to form an exciton.
  • This exciter is unstable in the general environment and will then release energy in the form of light or heat back to a stable ground state.
  • the excited state generated by recombination of electrons and holes is theoretically only 25% is a singlet excited state, and the remaining 75% is a triplet excited state, which will return to the ground state in the form of phosphorescence or heat.
  • OLEDs organic light-emitting diodes
  • conventional organic fluorescent materials can only emit light with 25% singlet excitons formed by electrical excitation, and the internal quantum efficiency of the device is low (up to 25%). External quantum efficiency is generally less than 5%, which is far from the efficiency of phosphorescent devices.
  • the phosphorescent material enhances the intersystem crossing due to the strong spin-orbit coupling of the center of the heavy atom, it can effectively utilize the singlet excitons and triplet exciton luminescence formed by electrical excitation, so that the internal quantum efficiency of the device is 100%.
  • Thermally activated delayed fluorescence (TADF) materials are the third generation of organic luminescent materials developed after organic fluorescent materials and organic phosphorescent materials. Such materials generally have a small singlet-triplet energy level difference ( ⁇ E ST ), and triplet excitons can be converted into singlet exciton luminescence by inter-system enthalpy. This can make full use of the singlet excitons and triplet excitons formed under electrical excitation, and the internal quantum efficiency of the device can reach 100%.
  • the material structure is controllable, the property is stable, the price is cheap, no precious metal is needed, and the application prospect in the field of OLEDs is broad.
  • T1 and S1 states of the design molecule have strong CT characteristics, and very small S1-T1 state energy gaps, although High T 1 ⁇ S 1 state exciton conversion is achieved by the TADF process, but at the same time results in a low S1 state radiation transition rate, and therefore, it is difficult to achieve (or simultaneously achieve) high exciton utilization and high fluorescence radiation efficiency; Even though doped devices have been used to mitigate the T exciton concentration quenching effect, most TADF material devices have a significant efficiency roll-off at high current densities.
  • the present applicant provides a dibenzo six-membered ring-substituted compound having xanthone as a core and its use.
  • the oxaxanthone compound based on the TADF mechanism of the invention is applied as an luminescent layer material to an organic light emitting diode, and the OLED device using the compound of the invention has good photoelectric performance and can meet the requirements of the panel manufacturing enterprise.
  • the Applicant provides a compound having a xanthone as a core, the structure of which is as shown in the general formula (1):
  • R is represented by the general formula (2), the general formula (3), the general formula (4) or the general formula (5):
  • X 1 , Y are an oxygen atom, a sulfur atom, a selenium atom, a C 1-10 linear or branched alkyl substituted alkylene group, an aryl substituted alkylene group, an alkyl group or an aryl substituted tertiary amine group.
  • R 1 is selected from the structure represented by the general formula (6)
  • R 2 is selected from the structure represented by the general formula (7):
  • a is X 2 and X 3 are each represented by an oxygen atom, a sulfur atom, a selenium atom, a C 1-10 linear or branched alkyl substituted alkylene group, an aryl substituted alkylene group, an alkyl group or an aryl group substituted tertiary group.
  • One of the amine groups; a through the C L1 -C L2 bond, the C L2 -C L3 bond, the C L3 -C L4 bond, the C L4 -C L5 bond, the C L'1 -C L'2 bond, C L a '2 -C L'3 bond, a C L'3 -C L'4 bond or a C L'4 -C L'5 bond is attached to the formula (2) or the formula (4);
  • Ar 2 and Ar 3 are each independently represented by a phenyl group, a C 1-10 linear or branched alkyl substituted phenyl group, a diphenyl group, a terphenyl group, or a naphthyl group;
  • R 3 and R 4 are each independently represented by an alkyl group having 1 to 10 carbon atoms, an substituted or unsubstituted aryl group having 1 to 50 carbon atoms, an aryl group or an alkyl group having 1 to 50 carbon atoms.
  • the substituted, unsubstituted or unsubstituted carbon atom is a heteroaryl group of 1 to 50.
  • the R 3 and R 4 are each independently selected from the group consisting of an alkyl group having a carbon atom of 1-10, a phenyl group, a C 1-10 linear or branched alkyl group substituted phenyl group, a diphenyl group, a terphenyl group. a structure represented by a group, a naphthyl group, a formula (8), a formula (9), a formula (10) or a formula (11);
  • Ar 4 , Ar 5 and Ar 6 each independently represent a phenyl group, a C 1-10 linear or branched alkyl substituted phenyl group, a diphenyl group, a terphenyl group, a naphthyl group, and a C 1-10 straight
  • R 5 and R 6 are each independently selected from hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aromatic group having 4 to 20 carbon atoms;
  • X 4 represents an oxygen atom, a sulfur atom, a selenium atom, a C 1-10 linear or branched alkyl substituted alkylene group, an aryl substituted alkylene group, an alkyl group or an aryl substituted tertiary amine group.
  • the Ar is expressed as The structural formula of the compound is expressed as:
  • R is:
  • the specific structure of the xanthone-based compound is:
  • the Applicant also provides a light-emitting device comprising the compound as a light-emitting layer material for producing an organic electroluminescent device.
  • the compound is used as a host material of the light-emitting layer for producing an organic electroluminescent device.
  • the Applicant also provides a method of preparing the compound, the reaction equation occurring during the preparation is:
  • the reaction process of Formula 1 is as follows: weigh the brominated compound with the xanthone as the core and RH, and dissolve it with toluene; then add Pd 2 (dba) 3 , tri-tert-butylphosphine, sodium t-butoxide; under an inert atmosphere, The mixed solution of the above reactants is reacted at a reaction temperature of 95 to 110 ° C for 10 to 24 hours, and the reaction solution is cooled and filtered, and the filtrate is subjected to rotary distillation to pass through a silica gel column to obtain a target product;
  • the molar ratio of the bromide to the RH of the xanthone is 1:1.0-4.0; the molar ratio of the bromide of the Pd 2 (dba) 3 to the xanthone is 0.006-0.02:1, three The molar ratio of tert-butylphosphine to xanthone as the core bromide is 0.006 to 0.02:1, and the molar ratio of sodium t-butoxide to xanthone as the core bromide is 1.0 to 4.0:1;
  • the reaction process of Formula 2 is as follows: weigh the brominated compound with the xanthone as the core and Ar-B(OH) 2 , and dissolve it with toluene; then add Pd(PPh 3 ) 4 and sodium carbonate; under the inert atmosphere, the above The mixed solution of the reactants is reacted at a reaction temperature of 95 to 110 ° C for 10 to 24 hours, and the reaction solution is cooled and filtered, and the filtrate is rotary-screwed and passed through a silica gel column to obtain a target product;
  • the molar ratio of the bromide to the Ar-B(OH) 2 of the xanthone is 1:1.0-4.0; the molar ratio of the bromide of the Pd(PPh 3 ) 4 to the xanthone is 0.006. ⁇ 0.02:1, the molar ratio of sodium carbonate to xanthone as the core bromide is 1.0 to 4.0:1.
  • the compound of the invention uses xanthone as a mother core, destroys the crystallinity of the molecule, avoids the aggregation between molecules, and has good thermal stability; the structural molecule of the compound contains an electron donor (donor, D) and electrons.
  • the combination of receptors (A) can increase the orbital overlap, improve the luminous efficiency, and simultaneously connect the aromatic heterocyclic groups to obtain HOMO, LUMO spatially separated charge transfer state materials, and achieve the energy level difference between the small S1 state and the T1 state. Therefore, the reverse intersystem crossing is realized under the condition of thermal stimulation, and is suitable for use as a main material of the luminescent layer material.
  • the compound of the invention can be used as a host material of the light-emitting layer for the fabrication of the OLED light-emitting device, and obtains good device performance, and the current efficiency, power efficiency and external quantum efficiency of the device are greatly improved; at the same time, the life of the device is obviously improved. .
  • the compound material of the invention has good application effect in the OLED light-emitting device and has good industrialization prospect.
  • Figure 1 is a schematic view showing the structure of a device applied to the compound of the present invention
  • 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 a light-emitting layer
  • 6 is an electron transport layer
  • 7 is an electron injection layer
  • 8 is a cathode electrode layer.
  • HPLC-MS The material had a molecular weight of 634.19 and a molecular weight of 634.26.
  • HPLC-MS The molecular weight of the material was 762.32, and the measured molecular weight was 762.43.
  • HPLC-MS The material had a molecular weight of 533.24 and a molecular weight of 533.26.
  • HPLC-MS The material had a molecular weight of 686.29 and a molecular weight of 686.33.
  • HPLC-MS The material had a molecular weight of 631.25 and a molecular weight of 631.42.
  • HPLC-MS molecular weight of 755.28, measured molecular weight 755.29
  • HPLC-MS molecular weight of 711.25, measured molecular weight 711.40
  • HPLC-MS The molecular weight of the material was 937.37, and the measured molecular weight was 937.46.
  • HPLC-MS molecular weight of 826.28, measured molecular weight 826.36
  • HPLC-MS The material had a molecular weight of 838.36 and a molecular weight of 838.44.
  • HPLC-MS The material had a molecular weight of 796.31 and a molecular weight of 796.56.
  • HPLC-MS The material had a molecular weight of 811.32 and a molecular weight of 811.39.
  • HPLC-MS The material had a molecular weight of 734.29 and a molecular weight of 734.35.
  • HPLC-MS The material had a molecular weight of 786.25 and a molecular weight of 786.36.
  • HPLC-MS The material had a molecular weight of 686.29 and a molecular weight of 686.34.
  • HPLC-MS The material had a molecular weight of 619.18 and a molecular weight of 619.23.
  • HPLC-MS The molecular weight of the material was 1020.44, and the measured molecular weight was 1020.49.
  • HPLC-MS The material had a molecular weight of 840.32 and a molecular weight of 840.38.
  • the compound of the present invention can be used as a light-emitting layer material, and the thermal properties and HOMO levels of the compound C29, the compound C108 and the conventional material CBP of the present invention are measured, and the test results are shown in Table 1.
  • the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter, Germany), the heating rate is 10 ° C / min; the weight loss temperature Td is the temperature loss of 1% in the nitrogen atmosphere, The measurement was carried out on a TGA-50H thermogravimetric analyzer of Shimadzu Corporation, Japan, with a nitrogen flow rate of 20 mL/min; the highest occupied molecular orbital HOMO level and the lowest occupied molecular orbital LUMO level were determined by a photoelectron emission spectrometer (AC-2 type). Calculated by PESA) and UV spectrophotometer (UV) test, the test is atmospheric.
  • DSC differential scanning calorimetry
  • UV UV spectrophotometer
  • the compound of the present invention has high thermal stability, a suitable HOMO level, and is suitable as a light-emitting layer material; meanwhile, the compound of the present invention contains an electron donor (donor, D) and an electron acceptor (acceptor, A), the electrons and holes of the OLED device to which the compound of the present invention is applied are brought to an equilibrium state, so that device efficiency and lifetime are improved.
  • Examples 19-27 and Comparative Examples 1-3 The application effects of the compound synthesized by the present invention as a host material of the light-emitting layer in the device will be described in detail below by Examples 19-27 and Comparative Examples 1-3.
  • Examples 19-27 Compared with Comparative Examples 1-3 the light-emitting layer materials of the devices of Comparative Examples 1-3 were conventional materials, and the device light-emitting layer body materials of Examples 19-27 were Inventive compound.
  • the structural composition of the device obtained in each example is shown in Table 2.
  • the performance test results of each device are shown in Table 3.
  • the molecular structure of each compound is as follows:
  • the transparent substrate layer 1 is made of a transparent material such as glass; the ITO anode layer 2 (having a film thickness of 150 nm) is washed, that is, sequentially washed with alkali, washed with pure water, dried, and then subjected to ultraviolet-ozone washing to remove the organic surface of the transparent ITO. the remains.
  • molybdenum trioxide MoO 3 having a thickness of 10 nm was deposited as a hole injecting layer 3 by a vacuum vapor deposition apparatus.
  • a TASC having a thickness of 80 nm was evaporated as the hole transport layer 4.
  • the light emitting layer 5 of the OLED light emitting device is formed, and the structure thereof comprises the material compound C22 used as the host material of the OLED light emitting layer 5, and GD-19 is used as a doping material, and the doping ratio of the doping material is
  • the film thickness of the light-emitting layer was 5% by weight.
  • the vacuum evaporation electron-transporting layer material was continued to be TPBI, and the vacuum-deposited film thickness of the material was 40 nm, and this layer was the electron-transport layer 6.
  • a lithium fluoride (LiF) layer having a film thickness of 1 nm was formed by a vacuum evaporation apparatus, and this layer was an electron injection layer 7.
  • an aluminum (Al) layer having a film thickness of 80 nm was formed by a vacuum deposition apparatus, and this layer was used as the cathode reflective electrode layer 8.
  • the anode and the cathode are connected by a known driving circuit, and the luminous efficiency, the luminescence spectrum, and the current-voltage characteristics of the device are measured.
  • the mixture was mixed in a weight ratio of 100:10, thickness 30 nm) / electron transport layer 6 (TPBI, thickness 40 nm) / electron injection layer 7 (LiF, thickness 1 nm) / cathode electrode layer 8 (Al).
  • the mixture was mixed in a weight ratio of 100:10, thickness 30 nm) / electron transport layer 6 (TPBI, thickness 40 nm) / electron injection layer 7 (LiF, thickness 1 nm) / cathode electrode layer 8 (Al).
  • the compound of the invention has good application effect as an luminescent layer material in an OLED light-emitting device, and has a good industrialization prospect.

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

Abstract

La présente invention concerne un composé ayant du xanthone comme noyau et ses applications dans un composant électroluminescent organique. Le composé a du xanthone en tant que noyau parent et est relié à un groupe hétérocyclique aromatique, ce qui permet de rompre la symétrie moléculaire et la cristallinité moléculaire, d'empêcher l'effet d'une agrégation intermoléculaire et de fournir de grandes propriétés de formation de film. Le composé est appliqué en tant que matériau de couche électroluminescente sur une diode électroluminescente organique (OLED); un composant OLED appliqué avec le composé présente de grandes propriétés d'émission de lumière et peut satisfaire les demandes des fabricants de panneaux.
PCT/CN2017/097614 2016-08-18 2017-08-16 Composé substitué par un noyau dibenzo à six chaînons comprenant du xanthone comme noyau et ses applications WO2018033086A1 (fr)

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CN106467550B (zh) * 2016-08-18 2020-03-27 江苏三月光电科技有限公司 一种以氧杂蒽酮为核心的二苯并六元环取代化合物及其应用
CN108659010A (zh) * 2017-03-27 2018-10-16 北京绿人科技有限责任公司 一种有机化合物及其在有机电致发光器件中的应用
CN109867652B (zh) * 2017-12-04 2023-11-10 Cmdl有限公司 新型有机化合物及包含其的有机电致发光器件
CN110372691B (zh) * 2018-04-13 2021-10-22 江苏三月科技股份有限公司 一种以氧杂蒽酮为核心的化合物、其制备方法及其在oled上的应用
CN110526905B (zh) * 2018-05-25 2020-11-20 江苏三月科技股份有限公司 一种含酮的化合物及其在有机电致发光器件上的应用
CN110551132A (zh) * 2018-05-31 2019-12-10 江苏三月光电科技有限公司 一种含酮的化合物及其在有机电致发光器件上的应用
CN111484468B (zh) * 2019-01-25 2023-09-22 烟台显华光电材料研究院有限公司 一类用于制备有机光电器件的化合物
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CN111943941B (zh) * 2019-05-14 2023-08-15 江苏三月科技股份有限公司 一种以杂蒽酮为核心的化合物及其应用
CN113004259B (zh) * 2019-12-20 2023-12-26 江苏三月科技股份有限公司 一种以蒽酮骨架为核心的化合物及其应用
CN111116589B (zh) * 2019-12-26 2023-03-24 深圳大学 含氮杂环化合物、电子器件及其应用
CN114249713B (zh) * 2020-09-22 2024-05-03 江苏三月科技股份有限公司 一种含有氧杂蒽酮或硫杂蒽酮结构的有机化合物及其应用

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