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WO2017105041A1 - Composé organique et dispositif électroluminescent organique comprenant un tel composé - Google Patents

Composé organique et dispositif électroluminescent organique comprenant un tel composé Download PDF

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Publication number
WO2017105041A1
WO2017105041A1 PCT/KR2016/014477 KR2016014477W WO2017105041A1 WO 2017105041 A1 WO2017105041 A1 WO 2017105041A1 KR 2016014477 W KR2016014477 W KR 2016014477W WO 2017105041 A1 WO2017105041 A1 WO 2017105041A1
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Prior art keywords
group
aryl
alkyl
groups
compound
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Ceased
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PCT/KR2016/014477
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English (en)
Korean (ko)
Inventor
심재의
김태형
박호철
엄민식
백영미
손호준
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Doosan Corp
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Doosan Corp
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Publication date
Priority claimed from KR1020160074656A external-priority patent/KR101921377B1/ko
Application filed by Doosan Corp filed Critical Doosan Corp
Publication of WO2017105041A1 publication Critical patent/WO2017105041A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers

Definitions

  • Z 1 to Z 5 are each independently N or C (R 5 ), but at least one of Z 1 to Z 5 is N;
  • R 11 is deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, A C 6 to C 60 mono or diarylphosphinyl group and a C 6 to C 60 arylsilyl group, or an adjacent group (eg, any one of R 7 to R 10 or another R 11, etc.) May be joined to form a condensed
  • R 5 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy groups, C 1 to C 40 alkyloxy groups, C 3 to C 40 cycloalkyl groups, 3 to 40 heterocycloalkyl groups , C 6 ⁇ C 60 arylamine group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phospha Nyl group, C 6 ⁇ C 60 mono or diaryl phosphinyl group and C 6 ⁇ C 60 An arylsilyl group selected from the group consisting of, or adjacent groups (e.g., L 2 , other adjacent R 5 or R
  • R 6 and R 11 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ⁇ C 60, C 1 ⁇ C 40 alkyloxy group of, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group, or
  • L 1 to L 4 may be each independently selected from the group consisting of a single bond, phenylene group, biphenylene group, naphthalenyl group, fluorenyl group and carbazolyl group, preferably Preferably it may be selected from the group consisting of a single bond, a phenylene group, a biphenylene group and a naphthalenyl group, and more preferably may be selected from the group consisting of a single bond, a phenylene group, a biphenylene group and a naphthalenyl group. Both L 1 and L 2 may not be a single bond.
  • L 1 and L 2 may be each independently a single bond or a linker represented by any one of the following formulas C-1 to C-12, preferably L 1 and L 2 may be each independently a linker represented by one of Formulas C-1 to C-12:
  • the linkers represented by the formulas C-2, C-3, C-7, C-8, C-9, C-10, and C-11 have a steric hindrance effect, and thus include the above linker.
  • an additional efficiency synergistic effect is expected by preventing excitons from flowing over the emission layer due to the TTF (triplet-triplet fusion) effect caused by the increase of the T1 (triplet energy) value of the material.
  • L 1 and L 2 may be independently a linker represented by any one of Formulas C-2, C-7, C-8, and C-9.
  • R 5 to R 11 are each independently hydrogen, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and nuclear atoms 5 to 60 It may be selected from the group consisting of three heteroaryl groups, wherein the alkyl group, aryl group and heteroaryl group of R 5 to R 11 are each independently one or more selected from the group consisting of halogen, cyano group and C 6 ⁇ C 60 aryl group When substituted or unsubstituted with a substituent and substituted with a plurality of substituents, they may be the same or different from each other.
  • Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
  • organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
  • the structure of the organic EL device according to the present invention described above is not particularly limited, but referring to FIG. 1 as an example, for example, the anode 10 and the cathode 20 facing each other, and the anode 10 and the cathode ( 20) and an organic layer 30 positioned between them.
  • the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34.
  • a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light emitting layer 32
  • an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light emitting layer 32. can do.
  • the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, the electron transport layer 34 and the cathode
  • the electron injection layer 36 may be further included between the holes 20.
  • the hole injection layer 37 stacked between the hole transport layer 31 and the anode 10 may not only improve the interface property between the ITO used as the anode and the organic material used as the hole transport layer 31.
  • the surface is applied to the upper surface of the uneven ITO to soften the surface of the ITO, a layer that can be used without particular limitation as long as it is commonly used in the art, for example, may be used an amine compound It is not limited to this.
  • the compound represented by Chemical Formula 1 since the compound represented by Chemical Formula 1 has a high triplet energy, it may exhibit an excellent efficiency increase due to a triplet-triplet fusion (TTF) effect, and more preferably as a material for the electron transport auxiliary layer. Can be used.
  • the compound represented by Chemical Formula 1 may prevent the excitons generated in the light emitting layer from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. As a result, the number of excitons that contribute to light emission in the light emitting layer may be increased, and thus the light emitting efficiency of the device may be improved, and the durability and stability of the device may also be improved, thereby effectively increasing the life of the device. Most of the materials developed show physical characteristics that can be driven at low voltages, thereby improving their lifetime.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the positive electrode material may be made of a high work function conductor, for example, to facilitate hole injection, and may include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
  • metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • the cathode material may be made of a low work function conductor, for example, to facilitate electron injection, and may include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. The same metal or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • reaction mixture was cooled to room temperature and 500 mL of an ammonium chloride aqueous solution was added to the reaction solution to terminate the reaction, extracted with EA 1.0 L, and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain 20.3 g (yield 73%) of the title compound.
  • a target compound 28.0 was prepared by the same procedure as in [Preparation Example 1], except that 2,7-dibromo-9H-fluorene-9-one was used instead of 2-bromo-9H-fluorene-9-one. g (yield 77%) was obtained.
  • a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • Example 1 Compound 1 4.2 456 8.2 Example 2 Compound 4 3.7 452 8.5 Example 3 Compound 5 3.5 450 7.2 Example 4 Compound 8 3.5 452 8.8 Example 5 Compound 14 3.7 455 9.1 Example 6 Compound 20 3.8 452 8.5 Example 7 Compound 37 4.5 455 8.5 Example 8 Compound 52 4.5 455 7.8 Example 9 Compound 53 3.9 452 7.9 Example 10 Compound 59 3.6 455 8.2 Example 11 Compound 91 3.3 455 8.1 Example 12 Compound 97 3.4 458 8.5 Example 13 Compound 102 3.7 455 8.6 Example 14 Compound 114 4.2 456 8.0 Example 15 Compound 134 4.1 455 8.9 Example 16 Compound 136 3.9 458 8.5 Example 17 Compound 141 3.8 455 7.2 Example 18 Compound 147 4.0 456 7.5 Comparative Example 1 Alq 3 4.7 458 5.6 Comparative Example 2 - 4.8
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol
  • UV OZONE cleaner Power sonic 405, Hwashin Tech
  • DS-205 hole transporting layer
  • NPB hole transporting auxiliary layer
  • ADN + 5% DS-405 light emitting layer
  • Doosan Corporation 30 nm) /
  • Example 19 Compound 5 4.2 456 8.2 Example 20 Compound 6 3.9 450 7.5 Example 21 Compound 18 3.6 452 7.8 Example 22 Compound 22 3.8 455 7.9 Example 23 Compound 31 3.6 458 8.4 Example 24 Compound 37 3.9 458 8.0 Example 25 Compound 44 4.0 450 7.8 Example 26 Compound 56 4.2 452 7.9 Example 27 Compound 70 4.5 455 8.5 Example 28 Compound 82 3.9 456 8.2 Example 29 Compound 118 3.3 458 9.1 Example 30 Compound 128 4.2 455 7.5 Example 31 Compound 145 4.3 456 7.8 Example 32 Compound 149 3.9 458 8.5 Example 33 Compound 104 3.8 459 8.1 Example 34 Compound 106 3.9 459 8.2 Example 35 Compound 108 3.9 459 8.0 Example 36 Compound 110 3.8 455 8.3 Example 37 Compound 111 4.0 460 8.1 Example 38 Compound 114 4.1 4
  • the blue organic electroluminescent devices (Examples 19 to 79) using the compound of the present invention in the electron transport auxiliary layer were compared to the blue organic electroluminescent devices (Comparative Example 3) without the electron transport auxiliary layer. It was found to exhibit excellent performance in terms of current efficiency, light emission peak, and driving voltage.
  • the current efficiency is higher than the compound 97 without the linker (Example 79), the driving voltage shows a lower performance I could see that.
  • the band gap is widened due to the increase in the LUMO level of the material, which increases the current efficiency and further lowers the driving voltage, which is more preferable.
  • organic layer 31 hole transport layer
  • the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant. Le composé, selon la présente invention, est destiné à une couche de matériau organique d'un dispositif électroluminescent organique, de préférence une couche électroluminescente, une couche de transport d'électrons ou une couche de transport d'électrons auxiliaire, et permet ainsi d'améliorer l'efficacité lumineuse, la tension de commande, la durée de vie, etc. du dispositif électroluminescent organique.
PCT/KR2016/014477 2015-12-15 2016-12-09 Composé organique et dispositif électroluminescent organique comprenant un tel composé Ceased WO2017105041A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
KR10-2015-0179244 2015-12-15
KR20150179244 2015-12-15
KR10-2016-0074656 2016-06-15
KR1020160074656A KR101921377B1 (ko) 2015-12-15 2016-06-15 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR10-2016-0074660 2016-06-15
KR1020160074660A KR101742436B1 (ko) 2015-12-15 2016-06-15 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

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WO2017105041A1 true WO2017105041A1 (fr) 2017-06-22

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113045577A (zh) * 2021-03-15 2021-06-29 吉林奥来德光电材料股份有限公司 电子传输材料及制备方法、有机电致发光器件和显示装置
CN114249713A (zh) * 2020-09-22 2022-03-29 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
WO2022269257A1 (fr) 2021-06-24 2022-12-29 University Court Of The University Of St Andrews Spiro-(fluorène-9,9'-(thio)xanthènes)
US11542258B2 (en) 2017-06-29 2023-01-03 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
WO2025001432A1 (fr) * 2023-06-27 2025-01-02 广东阿格蕾雅光电材料有限公司 Composé et dispositif électroluminescent

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140045153A (ko) * 2012-10-08 2014-04-16 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20140045266A (ko) * 2012-10-08 2014-04-16 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20150083917A (ko) * 2012-11-12 2015-07-20 메르크 파텐트 게엠베하 전자 소자용 재료
KR101560102B1 (ko) * 2014-11-20 2015-10-13 주식회사 엘지화학 유기 발광 소자
KR101593368B1 (ko) * 2015-04-22 2016-02-11 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140045153A (ko) * 2012-10-08 2014-04-16 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20140045266A (ko) * 2012-10-08 2014-04-16 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20150083917A (ko) * 2012-11-12 2015-07-20 메르크 파텐트 게엠베하 전자 소자용 재료
KR101560102B1 (ko) * 2014-11-20 2015-10-13 주식회사 엘지화학 유기 발광 소자
KR101593368B1 (ko) * 2015-04-22 2016-02-11 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11542258B2 (en) 2017-06-29 2023-01-03 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
CN114249713A (zh) * 2020-09-22 2022-03-29 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
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
CN113045577A (zh) * 2021-03-15 2021-06-29 吉林奥来德光电材料股份有限公司 电子传输材料及制备方法、有机电致发光器件和显示装置
WO2022269257A1 (fr) 2021-06-24 2022-12-29 University Court Of The University Of St Andrews Spiro-(fluorène-9,9'-(thio)xanthènes)
WO2025001432A1 (fr) * 2023-06-27 2025-01-02 广东阿格蕾雅光电材料有限公司 Composé et dispositif électroluminescent

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