WO2016127754A1 - Composé phosphorescent, son procédé de préparation et dispositif à diode électroluminescente organique l'utilisant - Google Patents

Composé phosphorescent, son procédé de préparation et dispositif à diode électroluminescente organique l'utilisant Download PDF

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Publication number
WO2016127754A1
WO2016127754A1 PCT/CN2016/070790 CN2016070790W WO2016127754A1 WO 2016127754 A1 WO2016127754 A1 WO 2016127754A1 CN 2016070790 W CN2016070790 W CN 2016070790W WO 2016127754 A1 WO2016127754 A1 WO 2016127754A1
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Prior art keywords
light emitting
phosphorescent compound
ring
emitting diode
organic light
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PCT/CN2016/070790
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English (en)
Chinese (zh)
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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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Priority to KR1020177025012A priority Critical patent/KR20170118113A/ko
Publication of WO2016127754A1 publication Critical patent/WO2016127754A1/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • H10K85/649—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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass

Definitions

  • the invention belongs to the field of organic electroluminescent materials, relates to a phosphorescent compound and an organic light emitting diode (OLED) device, and more particularly to a phosphorescent light having improved luminous efficiency due to high triplet energy and wide band gap.
  • OLED organic light emitting diode
  • light-emitting elements are self-luminous 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.
  • Light-emitting elements are also highly 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 with 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 word 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.
  • the organic electrophosphorescent material is a recently-appearing type of material, and is an organic electroluminescent material having high luminous efficiency and luminescent brightness.
  • a heavy metal atom By introducing a heavy metal atom, the triplet state of the originally forbidden at room temperature is utilized. Transition, so that 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.
  • Another object of the present invention is to provide an OLED having improved luminous efficiency.
  • the phosphorescent compound of the present invention has the following structural formula:
  • A, B, and C are a hetero atom N, and the others are C atoms;
  • Ar is a substituted or unsubstituted aryl, heteroaryl or fused ring aryl group of C6-30.
  • the Ar is the following structural formula:
  • Ar is phenyl, naphthyl, phenyl substituted phenyl or naphthyl, heteroaryl or fused ring aryl.
  • the Ioxazoline ring and the II oxazole ring are attached to the 6 or 7 position,
  • Ar is a phenyl group.
  • a or B is an N atom.
  • the Ioxazoline ring and the II oxazole ring are respectively prepared into a bromine, a boric acid or a boric acid ester, and are bonded together by a SUZUKI coupling reaction.
  • the Ioxazoline cyclobromide is obtained by reacting an Ioxazoline with a bromopyridine to form an N atom substituted oxazoline, which is then brominated by NBS.
  • 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 the phosphorescent compound.
  • the luminescent layer material includes a host and a dopant, and the phosphorescent compound serves as a host material.
  • the phosphorescent compound acts as a blue phosphorescent host material.
  • the three positions A, B and C are the positions of the nitrogen atom, and the structures respectively constituted are 2-pyridine, 3-pyridine and 4-pyridine.
  • the 1, 2, 3, and 4 positions of the Icarbazole ring are nitrogen atoms, which constitute the four isomers of the oxazoline:
  • the 5, 6, 7 and 8 positions of the II carbazole ring are the positions at which the two rings are coupled.
  • the phosphorescent compound of the present invention has a triplet energy level of 2.80 or more, and is used as a phosphorescent host.
  • the triplet energy level is greater than the triplet energy level of the doping material of 2.7 ev, and no energy is reversed to obtain a high-efficiency phosphorescent device.
  • the blue phosphorescent compound having high triplet energy of the present invention and using the blue phosphorescent compound as a main body of the light emitting layer of the organic light emitting diode, thereby promoting energy transfer in the light emitting layer, and improving the organic light emitting diode Blue emission efficiency and longevity.
  • Embodiment 1 is a nuclear magnetic diagram of the D structure of Embodiment 1.
  • Figure 2 is a partial enlarged view of Figure 1
  • FIG. 3 is a nuclear magnetic diagram of Compound 1 in Example 1,
  • Figure 4 is a structural magnetic nucleus of the structure A in the third embodiment
  • Figure 5 is a structural magnetic nucleus of Embodiment A in Embodiment 4
  • the present invention provides a novel phosphorescent material.
  • the examples herein are merely illustrative of the invention and are not intended to limit the scope of the invention.
  • the compounds A, B, and E referred to below were synthesized according to literature reports (Chem. Commun., 2013, 49, 5948-5950), and the structure was confirmed by nuclear magnetic resonance.
  • 0.1mol D 0.1mol E2 was added to a 1L four-necked bottle, add 400ML of toluene, 200ML of ethanol, 200ML of water, stir, add 0.2mol of potassium carbonate in batches, add nitrogen for 30 minutes, add palladium acetate 0.5G, tri-tert-butylphosphine 1ML , reflux overnight. Cooled, filtered to give a pale yellow solid, pristine detection 486.5 (MODI-TOF)
  • the compound 4 According to the synthesis process of the compound 1, 2, the compound 4 can be easily obtained.
  • the nuclear magnetic map of A4 is shown in Figure 5.
  • the ultraviolet absorption spectrum and the photoluminescence spectrum of the materials of the first to fourth 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 ITO substrate was patterned to have a light-emitting area of 3 mm ⁇ 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 first 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.
  • the organic light emitting diode was fabricated using the same manufacturing process as described above, except that the second body was used as the light emitting body.
  • 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.
  • the blue phosphorescent compound having high triplet energy of the present invention and using the blue phosphorescent compound as a main body of the light emitting layer of the organic light emitting diode, thereby promoting energy transfer in the light emitting layer, and improving The blue emission efficiency and lifetime of the organic light emitting diode.

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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)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Cette invention concerne un composé phosphorescent, qui répond à la formule structurale ci-dessous. Le composé phosphorescent selon l'invention a un niveau d'énergie d'état triplet qui n'est pas inférieur à 2,80 et peut être utilisé à titre de corps phosphorescent principal. Le niveau d'énergie d'état triplet est supérieur au niveau d'énergie d'état triplet de 2,7ev des matériaux dopés ; il n'y a pas réversion d'énergie ; et un dispositif phosphorescent efficace est obtenu. Le composé phosphorescent bleu à énergie d'état triplet élevée selon l'invention est utilisé à titre de corps principal d'une couche électroluminescente de diode électroluminescente organique, de façon que le transfert d'énergie dans la couche électroluminescente soit favorisé, et que le rendement lumineux bleu et la durée de vie de la diode électroluminescente organique soient améliorés.
PCT/CN2016/070790 2015-02-11 2016-01-13 Composé phosphorescent, son procédé de préparation et dispositif à diode électroluminescente organique l'utilisant WO2016127754A1 (fr)

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CN201510070488X 2015-02-11

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10547014B2 (en) 2017-06-23 2020-01-28 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US10644249B2 (en) 2017-12-22 2020-05-05 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US10892425B1 (en) 2017-03-03 2021-01-12 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11069860B2 (en) 2017-08-21 2021-07-20 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11104669B2 (en) 2018-02-02 2021-08-31 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11283027B1 (en) 2017-03-03 2022-03-22 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11444250B2 (en) 2017-12-05 2022-09-13 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11498914B2 (en) 2018-03-30 2022-11-15 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11542260B2 (en) 2018-01-31 2023-01-03 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11575088B2 (en) 2017-12-22 2023-02-07 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11608333B2 (en) 2018-03-20 2023-03-21 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11778904B2 (en) 2018-05-09 2023-10-03 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes

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CN104725373B (zh) * 2015-02-11 2016-10-05 北京拓彩光电科技有限公司 磷光化合物、制备方法以及有机发光二极管器件

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KR20140087806A (ko) * 2012-12-31 2014-07-09 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치

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US20140367649A1 (en) * 2013-06-14 2014-12-18 Samsung Display Co., Ltd. Organic light-emitting devices
CN104725373A (zh) * 2015-02-11 2015-06-24 北京拓彩光电科技有限公司 磷光化合物、制备方法以及有机发光二极管器件

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10892425B1 (en) 2017-03-03 2021-01-12 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11283027B1 (en) 2017-03-03 2022-03-22 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US10547014B2 (en) 2017-06-23 2020-01-28 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11069860B2 (en) 2017-08-21 2021-07-20 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11444250B2 (en) 2017-12-05 2022-09-13 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US10644249B2 (en) 2017-12-22 2020-05-05 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11575088B2 (en) 2017-12-22 2023-02-07 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11542260B2 (en) 2018-01-31 2023-01-03 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11104669B2 (en) 2018-02-02 2021-08-31 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11608333B2 (en) 2018-03-20 2023-03-21 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11498914B2 (en) 2018-03-30 2022-11-15 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11778904B2 (en) 2018-05-09 2023-10-03 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes

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KR20170118113A (ko) 2017-10-24
CN104725373B (zh) 2016-10-05

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