WO2017067422A1 - Dérivé de carbazoline phényle pyrimidine et dispositif de diode électroluminescente organique associé - Google Patents

Dérivé de carbazoline phényle pyrimidine et dispositif de diode électroluminescente organique associé Download PDF

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WO2017067422A1
WO2017067422A1 PCT/CN2016/102244 CN2016102244W WO2017067422A1 WO 2017067422 A1 WO2017067422 A1 WO 2017067422A1 CN 2016102244 W CN2016102244 W CN 2016102244W WO 2017067422 A1 WO2017067422 A1 WO 2017067422A1
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substituted
unsubstituted
group
oxazoline
hydrogen
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PCT/CN2016/102244
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赵洪玉
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北京拓彩光电科技有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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

Definitions

  • the present invention relates to an aromatic heterocyclic derivative and an organic light emitting diode (OLED) device, and more particularly to an aromatic heterocyclic derivative having high luminous efficiency due to high triplet energy and electron transporting performance. And an OLED device using the aromatic heterocyclic derivative.
  • OLED organic light emitting diode
  • light-emitting elements are self-illuminating elements, they have advantages in terms of high pixel visibility and elimination of backlighting requirements with respect to liquid crystal displays, and thus are considered to be suitable for flat panel display elements, for example.
  • Light-emitting elements are also advantageous because they are thin and lightweight. Very high speed response is one of the features of this component.
  • a light-emitting element can be formed in the form of a film, planar light emission can be provided. Therefore, an element having a large area can be easily formed. This is a feature that is difficult to obtain using a point light source typified by an incandescent lamp and an LED or a linear light source typified by a fluorescent lamp. Therefore, the light-emitting element also has a large potential as a planar light source or the like applicable to illumination.
  • the excited state formed by the organic compound may be singlet or triplet.
  • the emission from the singlet excited state (S * ) is fluorescence, and the emission from the triplet excited state (T * ) is called phosphorescence.
  • the internal quantum efficiency of a light-emitting element using a fluorescent compound has a theoretical limit of 25% based on a ratio of S * to T * of 1:3.
  • organic electrophosphorescent materials are recently attracting a class of materials, organic electroluminescent materials with high luminous efficiency and luminescent brightness, which utilize the method of introducing heavy metal atoms to utilize the originally forbidden triplet transition at room temperature.
  • the internal quantum efficiency theory can reach 100%, which is four times that of a single fluorescent material (1, Cao Y., Parker ID, Heeger J., Nature, 1999, 397: 414-417.2, Wohlgenann M., et al. Nature, 2001, 409: 494-497.).
  • Most of the heavy metal atoms commonly used in organic electrophosphorescent materials are transition metals. Among them, ruthenium is the most widely used and most studied.
  • metal ruthenium complexes have high efficiency, strong phosphorescence at room temperature, and can pass through ligands.
  • the adjustment of the structure adjusts the wavelength of the illumination such that the color of the electroluminescent device covers the entire visible region. Therefore, designing and synthesizing new and highly efficient metal ruthenium complexes is of great significance for the development of phosphorescent materials.
  • the efficiency of the dopant is drastically reduced due to the quenching phenomenon, and thus exists for the light-emitting layer of the dopant having no host. limit. Therefore, it is desirable to form a layer of luminescent material by a dopant and a host having higher thermal stability and triplet energy.
  • holes from the anode and electrons from the cathode are combined at the body of the layer of luminescent material.
  • the single-state exciton of the host undergoes an energy level transition to the singlet or triplet level of the dopant, and an energy level transition from the triplet exciton of the host to the triplet level of the dopant occurs.
  • the excitons that transition to the singlet state of the dopant again transition to the triplet level of the dopant.
  • the exciton of the triplet level of the dopant transitions to the ground state, causing the luminescent layer to emit light.
  • the triplet energy of the bulk should be greater than the triplet energy of the dopant.
  • the triplet energy level of the body is smaller than the triplet energy of the dopant, a reverse transition from the dopant to the bulk energy occurs, thereby reducing the luminous efficiency.
  • CBP which is widely used in the main body, has a triplet level of 2.6 eV, a maximum energy level of about -6.3 eV, and a lowest energy level of about -2.8 eV. Therefore, using the triplet level 2.8eV, the highest level -5.8eV and the lowest level -3.0eV blue dopant FCNIr, the energy level reverse transition from dopant to host occurs, resulting in reduced luminous efficiency. In particular, the occurrence of a decrease in luminous efficiency is more remarkable under low temperature conditions.
  • Pyrimidine structure As an electron-withdrawing group, bipolar host materials and electronic materials can be designed with high triplet state and electron transport capability. Idemitsu Trading Co., Ltd. has been engaged in the development of main materials and electronic materials for pyrimidine series, and has developed some materials. A (refer to patent US 20040086745) B (reference patent US20140151647)
  • B level (HOMO-6.13, LUMO-2.62, singlet 3.51eV, triplet 2.65eV) two structures slightly different There is a big difference between the triplet and the HOMO.
  • the electron transport energy can reach 10 -6 , indicating the presence of pyrimidine groups and enhancing the electron transport ability.
  • the triplet level is high, HOMO is less than -6.0eV, which does not effectively block holes.
  • B can effectively block holes, the triplet level is a bit low and can only be used as the main material of red and green light.
  • the present invention relates to an aromatic heterocyclic derivative and an OLED device using a phosphorescent compound which substantially solve one or more problems due to limitations and disadvantages of the prior art.
  • An object of the present invention is to provide a phosphorescent compound which has high triplet energy and electron transporting properties and can be used as a host of a phosphorescent device and an electron transporting material.
  • Another object of the present invention is to provide an OLED device having higher luminous efficiency.
  • the structure of oxazoline is similar to that of carbazole, because the structure has a pyridine structure, the triplet state is higher than that of carbazole, the triplet state of the same structural material is also high, and the electron mobility is also greatly enhanced (Chil Won Lee and Jun Yeob Lee, Adv. Mater. 2013, 25, 5450–5454). In order to meet the requirements of blue phosphorescent materials in terms of triplet state, electron mobility, etc., it is a good choice to introduce oxazoline groups into the structure.
  • R1 to R5 each independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, a C1-C4 substituted or unsubstituted phenyl group or biphenyl,
  • Ar3, Ar4 are each independently a C1-C4 substituted or unsubstituted oxazoline, carbazole or hydrogen; and at least one is an oxazoline, an oxazole or an oxazoline is linked through a 9-position nitrogen atom,
  • One of the four positions 1, 2, 3, and 4 of the oxazoline ring is a nitrogen atom, which constitutes the four isomers of the oxazoline:
  • Ar5 represents hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aromatic group of C6-C40, a substituted or unsubstituted heterocyclic aromatic group,
  • A3 and a4 each independently represent a C1-C4 substituted or unsubstituted phenylene group, and j, k each independently represent 0 or 1, and the hetero atom of the heteroaryl group is N, O, S.
  • R1 is hydrogen or benzene
  • biphenyl R2 to R5 represent hydrogen
  • j k represents 0,
  • Ar5 represents a substituted or unsubstituted phenyl or biphenyl group.
  • the organic compound is represented by the following formula (II):
  • R6 to R8 each independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aryl group of C6-C40, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted fused ring aryl group; , substituted or unsubstituted fused ring heteroaryl.
  • Ar6, Ar7 represents hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or not Substituted aryl, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted naphthothiophene, oxazoline, pyridine, phenanthroline substituted or unsubstituted heterocyclic ring An aryl group; an oxazoline is linked by a 9-position nitrogen atom,
  • One of the four positions 1, 2, 3, and 4 of the oxazoline ring is a nitrogen atom, which constitutes the four isomers of the oxazoline:
  • A6 and a7 each independently represent a substituted or unsubstituted phenylene group, and m, n each independently represent 0 or 1.
  • R1 is hydrogen or benzene
  • R2 to R5 R6, R8 represent hydrogen
  • j, k m, n represents 0,
  • Ar6, Ar7 represents hydrogen
  • R7 is unsubstituted or substituted with 1-4 carbon atoms, phenyl Phenyl, naphthyl, anthracenyl, fluorenyl, aryl, heterocyclic aryl.
  • Ar3 and Ar4 are each independently an oxazoline, a hydrogen atom, or a carbazole, and at least one of them is an oxazoline.
  • the organic compound is represented by the following formula:
  • R9 and R10 each independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, a C1-C4 substituted or unsubstituted phenyl group or biphenyl.
  • R1 is hydrogen or benzene
  • R2 to R5, R6, R8 to R10 represent hydrogen
  • j n represents 1
  • Ar3 is oxazoline
  • Ar7 represents hydrogen
  • R7 is unsubstituted or substituted with 1-4 carbon atoms.
  • An organic light emitting diode device comprising: a first electrode; a second electrode opposite to the first electrode; a light emitting layer between the first electrode and the second electrode, wherein the light emitting layer comprises any one of the above organic compounds .
  • the material of the light-emitting layer includes a host and a dopant, and the above-described organic compound serves as a host material.
  • the host material is a blue phosphorescent host material.
  • the device is a display device and a lighting device.
  • the compound we designed is mainly the structure of the pyrimidine skeleton, and the structure of the two compounds A and B indicated in the background art is improved.
  • the triplet level needs to be increased.
  • Oxazolines are similar structures to carbazole and have the properties of carbazole, but the triplet and electron transport properties are stronger than carbazole.
  • the obtained oxazoline derivative still has a pyrimidine skeleton and an oxazoline structure, and the oxazoline is bonded through the nitrogen atom at the 9-position, and the molecular weight does not largely change.
  • the oxazoline has good solubility in an alcohol solvent, and it is bonded to the aromatic ring to maintain this property.
  • there is a pyrimidine skeleton in the molecule which is also a group soluble in alcohol.
  • the carbazole group is a rigid group, and the obtained A and B structures have low solubility, which is not favorable for purification.
  • the structure designed by this patent has an oxazoline structure, is soluble in an alcohol solvent, and is convenient for purification. It is easily soluble in alcohol solvents and can be used as an inkjet printing OLED material.
  • Figure 1 shows the nuclear magnetic properties of compound 3
  • Figure 3 shows the nuclear magnetic field of the first body
  • Figure 4 shows the nuclear magnetic field of the second body
  • Figure 5 shows the nuclear magnetic field of the fourth body.
  • the ⁇ -oxazoline was used as a reactant to obtain a compound to obtain a third host material.
  • Compound 8 was synthesized according to the synthesis process of the second host except that the amount of the oxazoline substance was half, and the compound 8 was obtained as a pale yellow solid in a yield of 65%.
  • the amount of the carbazole was 1.3 times that of the compound 8, and the reaction was carried out for 24 hours, and the column was purified to obtain a white solid, which was determined to be the target product by FD-MS.
  • the ultraviolet absorption spectrum and the photoluminescence spectrum of the materials of the first to sixth host materials prepared by the above-described synthesis examples and the comparative examples represented by the following chemical formulas at a low temperature (for example, 77 K) according to the method of the present invention were measured, and the results thereof were measured.
  • a low temperature for example, 77 K
  • the main body to the main body six or three linear states are higher than 2.92 eV, which can meet the requirements of the main body of the blue phosphorescent material.
  • the introduction of oxazoline increased the triplet state, and the ratio of HOMO and LUMO decreased, indicating that the electron absorption of oxazoline was obvious.
  • the main body five introduces an electron-withdrawing substituent pyridine, HOMO, LUMO is also greatly reduced, and the triplet state is relatively small.
  • the introduction group is an acridine structure, which is an electron-donating group, and the LUMO and HOMO are significantly increased, and the electron transport performance is lowered.
  • a production example of an organic light emitting diode using a blue phosphorescent compound formed of the above first to sixth host materials and a material of a comparative example as a blue host will be described below.
  • the ITO substrate was patterned to have a light-emitting area of 3 mm X 3 mm, and then washed. After the ITO substrate was placed in a vacuum chamber, the bottom pressure was set to 1 ⁇ 10 -6 Torr. Then, on the ITO for forming the anode, HATCN having a thickness of about 50 angstroms was formed for the hole injection layer, and NPD having a thickness of about 550 angstroms was formed for the hole transport layer to form a TAPC having a thickness of about 100 angstroms. In the hole injection layer, a second host material having a thickness of about 300 angstroms and a FCNIr having a doping concentration of about 15% were formed for the light-emitting layer.
  • TmPyPb having a thickness of 400 angstroms was formed for the electron transport layer
  • LiF having a thickness of about 5 angstroms was formed for the electron injection layer
  • an Al layer cathode of 1,100 angstroms was formed.
  • a packaging process is performed using a UV curable encapsulant and a moisture absorbent to form a light emitting diode.
  • An organic light emitting diode was fabricated in the same manner as in Production Example 1, except that the comparative example main body was used as the light emitting body.
  • Example 4 introduction of acridine increased the transport of holes, thus the starting voltage ratio Lower, the system has a stronger ability to transport holes, the positive and negative charge transfer is not balanced, the life and efficiency are affected, and the performance of the main body is less than that of the introduction of oxazoline.
  • the system introduces oxazoline, the electron-deficient properties of oxazoline are manifested, electron transport and injection are improved, and efficiency and lifetime are also significantly improved.
  • the method of the present invention produces a blue phosphorescent compound having high triplet energy, and uses the blue phosphorescent compound as a main body of the light emitting layer of the organic light emitting diode, thereby promoting energy in the light emitting layer Transfer and improve the blue emission efficiency and lifetime of the organic light-emitting layer.

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

Abstract

La présente invention concerne un composé organique de formule (I), ledit composé étant un matériau organique émetteur de lumière phosphorescente. La carbazoline est liée à un cycle aromatique, le composé organique présente une bonne solubilité dans les solvants alcooliques, et le squelette de pyrimidine dans la molécule est également un groupe soluble dans l'alcool. La structure carbazoline du composé lui confère un état de triplet élevé et une bonne mobilité d'électrons, et le composé joue le rôle d'un hôte phosphorescent bleu et d'un matériau de transport d'électrons. Le composé est par ailleurs soluble dans des solvants alcooliques, il facilite la purification, etc., et peut également servir de matériau OLED pour l'impression à jet d'encre.
PCT/CN2016/102244 2015-10-22 2016-10-17 Dérivé de carbazoline phényle pyrimidine et dispositif de diode électroluminescente organique associé WO2017067422A1 (fr)

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CN2015106910753 2015-10-22

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CN105384759B (zh) * 2015-10-22 2017-12-15 北京拓彩光电科技有限公司 芳香杂环衍生物和使用该化合物的有机发光二极管器件
TWI582081B (zh) * 2016-03-25 2017-05-11 昱鐳光電科技股份有限公司 用於有機電激發光元件之化合物及使用該化合物之有機電激發光元件
WO2018164545A1 (fr) * 2017-03-10 2018-09-13 주식회사 엘지화학 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant
CN108929338A (zh) * 2018-03-19 2018-12-04 北京拓彩光电科技有限公司 芳香杂环延迟荧光化合物和及其有机发光二极管器件
KR102647025B1 (ko) * 2018-12-28 2024-03-12 엘지디스플레이 주식회사 발광 특성이 우수한 유기 화합물, 이를 포함하는 유기발광다이오드 및 유기발광장치

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CN105384759A (zh) * 2015-10-22 2016-03-09 北京拓彩光电科技有限公司 芳香杂环衍生物和使用该化合物的有机发光二极管器件

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KR101840313B1 (ko) * 2011-02-14 2018-03-21 에스에프씨 주식회사 피리딘 유도체 화합물 및 이를 포함하는 유기전계발광소자
KR101584753B1 (ko) * 2013-06-13 2016-01-12 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자

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