+

WO2018155904A1 - Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant - Google Patents

Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant Download PDF

Info

Publication number
WO2018155904A1
WO2018155904A1 PCT/KR2018/002134 KR2018002134W WO2018155904A1 WO 2018155904 A1 WO2018155904 A1 WO 2018155904A1 KR 2018002134 W KR2018002134 W KR 2018002134W WO 2018155904 A1 WO2018155904 A1 WO 2018155904A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
compound
light emitting
layer
substituted
Prior art date
Application number
PCT/KR2018/002134
Other languages
English (en)
Korean (ko)
Inventor
정민우
이동훈
조성미
허동욱
한미연
이정하
Original Assignee
주식회사 엘지화학
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
Priority claimed from KR1020180020039A external-priority patent/KR101959514B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880005450.6A priority Critical patent/CN110114345B/zh
Priority to US16/474,008 priority patent/US11312691B2/en
Priority to JP2019530157A priority patent/JP6966041B2/ja
Priority to EP18758393.5A priority patent/EP3546453B1/fr
Publication of WO2018155904A1 publication Critical patent/WO2018155904A1/fr

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • 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
    • 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]
    • H10K50/17—Carrier injection layers

Definitions

  • substituted or unsubstituted is deuterium halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxy group; Silyl group boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group aralkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroaryl amine group Aryl amine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups including one or more of N, 0, and
  • the alkyl group may be linear or branched, carbon number is not particularly limited, but 1 to . 40 people . It is preferable. Work According to the exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. In accordance with one embodiment of i, the number of carbon atoms of the alkyl group is from 1 to 10 eu is, according to still one embodiment, the number of carbon atoms of the alkyl group is 1 to 6.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, ter t-butyl, sec ⁇ butyl, 1-methyl-butyl ⁇ 1-ethyl-butyl, pentyl, n—pentyl, isopentyl, neopentyl, tert-pentyl, nuclear chamber.
  • n-nuclear 1-methylpentyl ⁇ 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2—ethylbutyl, heptyl, n-haptyl, 1-methylnuclear, cyclopentylmethyl, cyclo Hectylmethyl ⁇ octyl, n-octyl, ter t-octyl, 1-methylheptyl, 2-ethylnuclear 2-propylpentyl. n-nonyl.
  • Specific examples include vinyl, 1—propenyl and isopropenyl. 1-butenyl. 2-butenyl. 3-butenyl, 1-pentenyl, 2—pentenyl, 3-pentenyl, 3-methyl— 1-butenyl. 1, 3-butadienyl, allyl.
  • an aralkyl group. . Aralkenyl group The aryl group in an alkylaryl group and an arylamine group is the same as the example of the aryl group mentioned above.
  • the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above.
  • the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above.
  • FIG. 2 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • the compound represented by Formula 1 may be included in at least one of the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer ⁇ the organic light emitting device according to the present invention.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode.
  • the anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (IT0), indium zinc oxide (IZ0); ⁇ 0: A1 or SN0 2 : A combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene KPED0T), polypyri and polyaniline, and the like, but are not limited thereto. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group includes pyrene, anthracene, chrysene, periplanthene having an arylamino group, and a styrylamine compound is substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the above-mentioned arylamine, and one or two or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl and arylamino groups are substituted or unsubstituted.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium. Calcium, ytterbium and samarium, each followed by an aluminum or silver layer.
  • the electron injection layer is a layer for injecting electrons from the electrode. Has the ability to transport electrons, the effect of electron injection from the cathode.
  • Compound is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane. Anthrone and the like, derivatives thereof, metal complex compounds and nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • a glass substrate coated with a thin film having an indium tin oxkle (IT0) of 1,300 A was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • the detergent was used the Fisher Company (Fischer. Co.) products
  • distilled water was Millipore (MiUipore Co.) was used as the second filtered distilled water to drive a filter (Filter) of the product.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner.
  • a hole injection layer was formed by thermally vacuum depositing the following HI-1 compound to a thickness of 50 A on the IT0 transparent electrode prepared as described above.
  • a hole transport layer was formed by thermal vacuum deposition of the following HT-1 compound at a thickness of 250 A on the hole injection layer, and an electron blocking layer was formed by vacuum deposition of the following HT-2 compound at a thickness of 50 A on the HT-1 deposition film.
  • the following HI-1 compound was vacuum-deposited to a thickness of 500 A on the prepared IT0 transparent electrode to form a hole injection layer.
  • the following HT-1 compound was vacuum deposited to a thickness of 400 A on the hole injection layer to form a hole transport layer, and the host HI and the dopant D1 compound were vacuum deposited to a thickness of 300 A at a weight ratio of 97.5: 2.5 as the light emitting layer.
  • the following compound ET-A was vacuum deposited to a thickness of 50 A on the emission layer to form an electron transport layer.
  • Compound 1 and LiQ (Li thium Quinolate) prepared in Example 1 were vacuum deposited on the electron transport layer at a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 350A.
  • Lithium fluoride (LiF) and aluminum at a thickness of 2,000 A were sequentially deposited on the electron injection and transport layer to form a cathode.
  • An organic light emitting device was manufactured according to the same method as Experimental Example 2-1, except for using the compound shown in Table 2 below instead of compound 1 of Example 1 in Experimental Example 2-1.
  • the compounds of CE4, CE2 and CE3 in Table 2 are as follows.
  • Light emitting layer 4 cathode
  • Hole injection layer 6 Hole transport layer

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 hétérocyclique et un élément électroluminescent organique l'utilisant.
PCT/KR2018/002134 2017-02-21 2018-02-21 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant WO2018155904A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN201880005450.6A CN110114345B (zh) 2017-02-21 2018-02-21 新杂环化合物和使用其的有机发光器件
US16/474,008 US11312691B2 (en) 2017-02-21 2018-02-21 Heterocyclic compounds and organic light emitting device using the same
JP2019530157A JP6966041B2 (ja) 2017-02-21 2018-02-21 新規なヘテロ環式化合物およびこれを利用した有機発光素子
EP18758393.5A EP3546453B1 (fr) 2017-02-21 2018-02-21 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2017-0022903 2017-02-21
KR20170022903 2017-02-21
KR10-2018-0020039 2018-02-20
KR1020180020039A KR101959514B1 (ko) 2017-02-21 2018-02-20 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자

Publications (1)

Publication Number Publication Date
WO2018155904A1 true WO2018155904A1 (fr) 2018-08-30

Family

ID=63253800

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2018/002134 WO2018155904A1 (fr) 2017-02-21 2018-02-21 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant

Country Status (1)

Country Link
WO (1) WO2018155904A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003012890A2 (fr) 2001-07-20 2003-02-13 Novaled Gmbh Composant electroluminescent a couches organiques
KR20110047803A (ko) * 2009-10-30 2011-05-09 제일모직주식회사 유기 광전 소자용 화합물 및 이를 포함하는 유기 광전 소자
KR20130073537A (ko) 2011-12-23 2013-07-03 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
WO2014010823A1 (fr) * 2012-07-13 2014-01-16 주식회사 엘지화학 Composé hétérocyclique et élément électronique organique comprenant ce composé
CN103579528A (zh) * 2012-07-31 2014-02-12 昆山维信诺显示技术有限公司 电子传输层、含该电子传输层的有机电致发光器件及制备
KR20160111780A (ko) * 2015-03-17 2016-09-27 주식회사 엘지화학 유기 발광 소자
WO2017074053A1 (fr) * 2015-10-27 2017-05-04 주식회사 엘지화학 Composé et dispositif électroluminescent organique le comprenant

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003012890A2 (fr) 2001-07-20 2003-02-13 Novaled Gmbh Composant electroluminescent a couches organiques
KR20110047803A (ko) * 2009-10-30 2011-05-09 제일모직주식회사 유기 광전 소자용 화합물 및 이를 포함하는 유기 광전 소자
KR20130073537A (ko) 2011-12-23 2013-07-03 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
WO2014010823A1 (fr) * 2012-07-13 2014-01-16 주식회사 엘지화학 Composé hétérocyclique et élément électronique organique comprenant ce composé
CN103579528A (zh) * 2012-07-31 2014-02-12 昆山维信诺显示技术有限公司 电子传输层、含该电子传输层的有机电致发光器件及制备
KR20160111780A (ko) * 2015-03-17 2016-09-27 주식회사 엘지화학 유기 발광 소자
WO2017074053A1 (fr) * 2015-10-27 2017-05-04 주식회사 엘지화학 Composé et dispositif électroluminescent organique le comprenant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
LIN, S. ET AL.: "Synthesis of 9.9'-biphenanthryl-10,10'-bis(oxazoline)s and Their Preliminary Evaluations in the Friedel-Crafts Alkylations of Indoles with Nitroalkenes", TETRAHEDRON, vol. 65, no. 5, 2009, pages 1010 - 1016, XP025816082 *

Similar Documents

Publication Publication Date Title
KR101953767B1 (ko) 신규한 유기금속 화합물 및 이를 이용한 유기발광 소자
KR101978453B1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
KR102123015B1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
KR20200063076A (ko) 신규한 화합물 및 이를 포함하는 유기발광 소자
KR102231197B1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
WO2018016898A1 (fr) Nouveau composé hétérocylique et dispositif électroluminescent organique utilisant celui-ci
KR101929448B1 (ko) 신규한 화합물 및 이를 포함하는 유기발광 소자
KR101959514B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자
JP7124260B2 (ja) 有機金属化合物およびこれを含む有機発光素子
KR102160653B1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
KR102147480B1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
WO2018084423A2 (fr) Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant
US20200039971A1 (en) Novel heterocyclic compound and organic light emitting device comprising the same
KR102235480B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
KR102235479B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
WO2018093080A1 (fr) Nouveau composé hétérocyclique et dispositif électroluminescent organique le comprenant
KR102206482B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
KR102064415B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자
KR101967381B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
WO2018190522A1 (fr) Nouveau composé et dispositif électroluminescent organique le contenant
KR20200052236A (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2019004612A1 (fr) Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant
KR102236281B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
KR101917858B1 (ko) 신규한 화합물 및 이를 포함하는 유기발광 소자
KR102034196B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자

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: 18758393

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2019530157

Country of ref document: JP

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 2018758393

Country of ref document: EP

Effective date: 20190627

NENP Non-entry into the national phase

Ref country code: DE

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载