WO2018186551A1 - Composé organique et élément électroluminescent organique le comprenant - Google Patents

Composé organique et élément électroluminescent organique le comprenant Download PDF

Info

Publication number
WO2018186551A1
WO2018186551A1 PCT/KR2017/013250 KR2017013250W WO2018186551A1 WO 2018186551 A1 WO2018186551 A1 WO 2018186551A1 KR 2017013250 W KR2017013250 W KR 2017013250W WO 2018186551 A1 WO2018186551 A1 WO 2018186551A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
aryl
alkyl
formula
heteroaryl
Prior art date
Application number
PCT/KR2017/013250
Other languages
English (en)
Korean (ko)
Inventor
심재의
엄민식
박우재
Original Assignee
주식회사 두산
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 주식회사 두산 filed Critical 주식회사 두산
Publication of WO2018186551A1 publication Critical patent/WO2018186551A1/fr

Links

Images

Classifications

    • 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
    • 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
    • C07D209/96—Spiro-condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • H10K50/15—Hole transporting layers
    • 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
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • the dotted line is the part where condensation takes place
  • the compound of the present invention has excellent thermal stability, carrier transporting ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic EL device.
  • the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel since the aspects such as light emission performance, driving voltage, lifespan, and efficiency are greatly improved.
  • organic layer 31 hole transport layer
  • the present invention provides a compound represented by the following formula (1):
  • l, m, n and p are each independently an integer from 0 to 4.
  • a 1 to A 4 and R 3 to R 6 which do not form a condensed ring with the ring represented by Formula 2 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 To 60 heteroaryl groups, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group and C 6 to C 60 arylamine Selected from the group consist
  • the electron transport auxiliary layer may be used as a material of any one of an electron transport auxiliary layer further laminated on the green phosphorescent light emitting layer, the electron transport layer, and the electron transport layer.
  • the electron transport auxiliary layer since the electron transport auxiliary layer has a high triplet energy, it may exhibit excellent efficiency due to the triplet-triplet fusion effect.
  • the amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40
  • R 8 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 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha Or a C 6 to C 60 mono or diarylphosphinyl group and a C 6 to C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and when R 8 is a plurality, Same or different from each other
  • R 10 and R 11 are each independently 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 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ for C 60 aryl phosphazene group, it said shed some light selected from the group consisting of an arylamine C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of;
  • R 9 is selected from the group consisting of an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms;
  • R 9 may be selected from the group consisting of phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group,
  • the phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, and naphthalenyl group of R 9 are each independently C 1 -C 40 alkyl group, C 6 -C 60 aryl group and nuclear atom 5 to When unsubstituted or substituted with one or more substituents selected from the group consisting of 60 heteroaryl groups, they are the same or different from each other.
  • R 8 is selected from the group consisting of an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms;
  • R 8 may be selected from the group consisting of phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group,
  • organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1).
  • the compound may be used alone or mixed two or more.
  • the exciton generated in the light emitting layer may be prevented from being diffused into the electron transport layer or the hole transport layer adjacent to the light emitting layer.
  • the number of excitons contributing to light emission in the light emitting layer may be improved, and thus the luminous efficiency of the device may be improved, and the durability and stability of the device may be improved, and thus the life of the device may be efficiently increased.
  • 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
  • a green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound 1 as a light-emitting host material.
  • a red organic electroluminescent device was manufactured in the same manner as in Example 18, except that CBP was used instead of Compound 1 used as a light emitting host material in forming the emission layer in Example 18.
  • the structure of CBP used was as described in Comparative Example 1.
  • Example 18 Compound 1 3.6 518 21.4 Example 19 Compound 6 3.5 519 20.8 Example 20 Compound 13 4.0 518 19.5 Example 21 Compound 15 3.4 520 22.4 Example 22 Compound 35 3.7 518 21.8 Example 23 Compound 42 3.8 520 20.4 Example 24 Compound 55 3.5 518 19.8 Example 25 Compound 60 3.4 519 21.0 Example 26 Compound 72 3.7 520 22.2 Example 27 Compound 79 3.9 519 19.7 Example 28 Compound 83 4.1 518 21.4 Example 29 Compound 98 3.6 518 22.6 Example 30 Compound 112 3.8 518 20.4 Example 31 Compound 119 3.8 518 21.2 Comparative Example 2 CBP 5.4 521 15.8

Landscapes

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

Abstract

La présente invention concerne un nouveau composé, et un élément électroluminescent organique le comprenant. Le composé selon la présente invention est utilisé dans une couche organique d'un élément électroluminescent organique, de préférence, dans une couche électroluminescente, et permet ainsi d'améliorer l'efficacité lumineuse, la tension de commande, la durée de vie, et d'autres propriétés similaires de l'élément électroluminescent organique.
PCT/KR2017/013250 2017-04-07 2017-11-21 Composé organique et élément électroluminescent organique le comprenant WO2018186551A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020170045313A KR102390972B1 (ko) 2017-04-07 2017-04-07 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR10-2017-0045313 2017-04-07

Publications (1)

Publication Number Publication Date
WO2018186551A1 true WO2018186551A1 (fr) 2018-10-11

Family

ID=63713470

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2017/013250 WO2018186551A1 (fr) 2017-04-07 2017-11-21 Composé organique et élément électroluminescent organique le comprenant

Country Status (2)

Country Link
KR (1) KR102390972B1 (fr)
WO (1) WO2018186551A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102174390B1 (ko) * 2017-10-23 2020-11-04 주식회사 엘지화학 신규한 고리 화합물 및 이를 이용한 유기발광 소자
KR102633651B1 (ko) * 2018-12-19 2024-02-06 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
CN112321587B (zh) * 2020-10-30 2022-02-18 武汉天马微电子有限公司 一种有机化合物、电致发光材料及其应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010136109A1 (fr) * 2009-05-29 2010-12-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
KR20110002156A (ko) * 2009-07-01 2011-01-07 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 전자 소자
KR20140054132A (ko) * 2011-07-29 2014-05-08 메르크 파텐트 게엠베하 전자 소자용 화합물

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010136109A1 (fr) * 2009-05-29 2010-12-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
KR20110002156A (ko) * 2009-07-01 2011-01-07 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 전자 소자
KR20140054132A (ko) * 2011-07-29 2014-05-08 메르크 파텐트 게엠베하 전자 소자용 화합물

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
KLIMENKO. L. S. ET AL.: "Photocyclization of 2-azido-1-(4-tert-butylphenoxy)-9, 10-anthraquinone in the Presence of Substituted Phenols", RUSSIAN CHEMICAL BULLETIN , INTERNATIONAL EDITION, vol. 56, no. 6, 2007, pages 1130 - 1134, XP055558179 *
LAI, W.-Y. ET AL.: "Kinked Star-Shaped Fluorene/Triazatruxene Co-oligomer Hybrids with Enhanced Functional Properties for High-Performance, Solution-Processed , Blue Organic Light-Emitting Diodes", ADVANCED FUNCTIONAL MATERIALS, vol. 18, no. 2, 2008, pages 265 - 276, XP001510290 *

Also Published As

Publication number Publication date
KR102390972B1 (ko) 2022-04-27
KR20180113784A (ko) 2018-10-17

Similar Documents

Publication Publication Date Title
WO2017188597A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2015190718A1 (fr) Dispositif électroluminescent organique
WO2016105161A2 (fr) Composé organique et élément électroluminescent organique comprenant ce composé
WO2018080068A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2020159019A1 (fr) Composé électroluminescent organique, et dispositif électroluminescent organique l'utilisant
WO2020209679A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2018230782A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2018038400A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2018216921A2 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2017111439A1 (fr) Composé organique et dispositif électroluminescent organique comprenant ledit composé
WO2017003009A1 (fr) Composé émettant de la lumière organique et dispositif électroluminescent organique l'utilisant
WO2017209488A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2017111544A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2017111543A1 (fr) Composé organique et dispositif électroluminescent organique comprenant ce composé
WO2015133804A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2017188596A1 (fr) Composé organique électroluminescent et dispositif organique électroluminescent l'utilisant
WO2013168927A2 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2015111943A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2016105123A2 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2020116881A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2017111389A1 (fr) Composé organique et diode électroluminescente organique comprenant ledit composé
WO2015060635A1 (fr) Composé organique et élément organique électroluminescent le comprenant
WO2018043913A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2020218680A1 (fr) Composé organique et diode électroluminescente organique l'utilisant
WO2017105041A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 17904537

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC (EPO FORM 1205A DATED 3101.2020)

122 Ep: pct application non-entry in european phase

Ref document number: 17904537

Country of ref document: EP

Kind code of ref document: A1