WO2017069258A1 - Nouveau composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique - Google Patents

Nouveau composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique Download PDF

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Publication number
WO2017069258A1
WO2017069258A1 PCT/JP2016/081318 JP2016081318W WO2017069258A1 WO 2017069258 A1 WO2017069258 A1 WO 2017069258A1 JP 2016081318 W JP2016081318 W JP 2016081318W WO 2017069258 A1 WO2017069258 A1 WO 2017069258A1
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group
ring
carbon atoms
substituted
unsubstituted
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PCT/JP2016/081318
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English (en)
Japanese (ja)
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ウォレブ，ハインツ
ウォレブ，アナマリー
拓史 塩見
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出光興産株式会社
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Publication of WO2017069258A1 publication Critical patent/WO2017069258A1/fr

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    • 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
    • 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

  • L 1 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.
  • n is 0 or 1. Any one of R 1 ⁇ R 12 form a single bond in combination with *, R 1 ⁇ R 12, which does not bind with * are each independently a hydrogen atom, a halogen atom, or a substituent R a is there.
  • an electronic apparatus equipped with the organic electroluminescence element is provided.
  • the aryloxy group is represented as —OY 20 and examples of Y 20 include the same as those mentioned as the aryl group.
  • the number of ring-forming atoms of the heteroaryl group is 5 to 50, preferably 5 to 30, more preferably 5 to 24, and still more preferably 5 to 18.
  • the ring-forming atom other than the carbon atom of the heteroaryl group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
  • halogen atom examples include fluorine, chlorine, bromine, iodine and the like, preferably a fluorine atom.
  • a mono-substituted silyl group having a substituent selected from an alkyl group, an alkoxy group, and an aryl group is represented by —SiH 2 (Y 10 ), SiH 2 (OY 10 ), or —SiH 2 (Y 20 ).
  • a disubstituted silyl group having a substituent selected from an alkyl group, an alkoxy group, and an aryl group is -SiH (Y 10 ) 2 , -SiH (OY 10 ) 2 , -SiH (Y 20 ) 2 , -SiH (Y 10 ) (OY 10 ), —SiH (Y 10 ) (Y 20 ), —SiH (OY 10 ) (Y 20 ).
  • a tri-substituted silyl group having a substituent selected from an alkyl group, an alkoxy group, and an aryl group is -Si (Y 10 ) 3 , -Si (OY 10 ) 3 , -Si (Y 20 ) 3 , -Si (Y 10 ) 2 (OY 10 ), —Si (Y 10 ) (OY 10 ) 2 , —Si (Y 10 ) 2 (Y 20 ), —Si (Y 10 ) (Y 20 ) 2 , —Si (OY 10 ) 2 It is represented by (Y 20 ), —Si (OY 10 ) (Y 20 ) 2 or —Si (Y 10 ) (OY 10 ) (Y 20 ).
  • Y 10 and Y 20 are as described above, and when there are a plurality of Y 10 or Y 20 s , they may be the same as or different from each other.
  • R 21 to R 28 are aryl groups having 6 to 30 ring carbon atoms, and the remainder are hydrogen atoms.
  • a 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted phenanthrenyl. Selected from the group consisting of groups.
  • n is 1 and L 1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.
  • n is 0.
  • n is 0 means that L 1 does not exist and the pyrimidine ring and the triphenylene ring are bonded to each other by a single bond.
  • the compound represented by the formula (1) is a compound represented by the following formula (1-1).
  • a 1 , L 1 , n, R 2 to R 12 and R 21 to R 28 are as defined in the formula (1).
  • a 1 , L 1 , n, R 6 and R 21 to R 28 are as defined in the formula (1).
  • a 1 , L 1 , n, R 2 to R 12 , R 21 to R 24 and R 26 are as defined in the formula (1).
  • R 23 and R 26 are an aryl group having 6 to 30 ring carbon atoms or a heteroaryl group having 5 to 30 ring atoms.
  • a ring in which two adjacent R 21 to R 24 are bonded to each other and fused to a carbazole ring is a substituted or unsubstituted benzene ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted ring.
  • a 1 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.
  • a 1 is a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group
  • L 1 is a phenylene group, a biphenylene group or a naphthalenylene group
  • n is 0 or 1
  • R 2 to R 12 are all hydrogen atoms, or one or more of R 2 to R 12 are phenyl groups, the rest are hydrogen atoms, or adjacent 2 of R 2 to R 12
  • One is an unsubstituted benzene ring bonded to each other and fused to a triphenylene ring, and the rest are each independently a hydrogen atom or an unsubstituted phenyl group
  • All of R 21 to R 24 are hydrogen atoms, any of R 21 to R 24 is a phenyl group, the rest are hydrogen atoms, or two adjacent ones of R 21 to R 24 are Form a benzene ring, an indole
  • n is 0 in formulas (1), (1-1), (1-2) and (1-3).
  • L 1 does not exist, and the triphenylene ring and the pyrimidine ring are bonded to each other by a single bond.
  • a 1 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms
  • R 6 is a hydrogen atom or an aryl group having 6 to 30 ring carbon atoms
  • R 21 to R 24 are each independently a hydrogen atom or a substituted or unsubstituted phenyl group, or adjacent two of R 21 to R 24 are bonded to each other and fused to a carbazole ring.
  • an unsubstituted benzene ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring or a substituted or unsubstituted benzofuran ring, and the rest each independently represents a hydrogen atom or a substituted or unsubstituted phenyl Group
  • R 26 is a hydrogen atom or an aryl group having 6 to 30 ring carbon atoms.
  • the compound represented by the formula (1) is a compound represented by the following formula (1-5).
  • a 1 is as defined in the above formula (1).
  • the organic electroluminescent element of one embodiment of the present invention is an organic electroluminescent element having an anode, a cathode, and an organic thin film layer including at least a light emitting layer therebetween, Between the said light emitting layer and the said cathode, it has an organic thin film layer containing the compound represented by following formula (2), It is characterized by the above-mentioned.
  • the compound of the above formula (2) includes the compound of the above formula (1).
  • An organic EL element which is one embodiment of the present invention includes an organic thin film layer containing a compound represented by the above formula (2) (hereinafter sometimes referred to as a compound of the formula (2)) between a light emitting layer and a cathode.
  • a compound of the formula (2) a compound represented by the above formula (2)
  • a 1 , L 1 , n, R 1 to R 12 and R 31 to R 38 are as defined in the above formula (2).
  • R c is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
  • one or more of R 31 to R 38 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom having 5 to 30 ring atoms.
  • An indole ring, a substituted or unsubstituted indene ring or a substituted or unsubstituted benzofuran ring, and the rest are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
  • Any of the compounds of formula (2) can be synthesized by following the methods described in the synthesis examples or the reactions in the synthesis examples and using known alternative reactions and raw materials according to the target product.
  • the organic EL element of one embodiment of the present invention may include layers and materials other than these.
  • the hole injection layer is a layer containing a substance having a high hole injection property.
  • Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, aromatic amine compound, or high molecular compound (oligomer, dendrimer, polymer, etc.) can also be used.
  • the light-emitting layer is a layer including a substance having high light-emitting properties, and various materials can be used.
  • a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used as the substance having high light-emitting property.
  • a fluorescent compound is a compound that can emit light from a singlet excited state
  • a phosphorescent compound is a compound that can emit light from a triplet excited state.
  • the organic EL device of one embodiment of the present invention includes the compound represented by the formula (2) in the electron transport zone, but may further include the following compound.
  • the electron transport layer is a layer containing a substance having a high electron transport property.
  • metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes
  • heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives
  • 3) polymer compounds can be used.
  • a compound of formula (1) can be easily obtained by a person skilled in the art by selecting a starting compound corresponding to the target compound and reacting the starting compound according to the synthesis examples described below.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un élément électroluminescent organique comprenant une électrode positive, une électrode négative, et une couche en film mince organique qui contient au moins une couche électroluminescente et est disposée entre l'électrode positive et l'électrode négative. Cet élément électroluminescent organique comprend, entre la couche électroluminescente et l'électrode négative, une couche en film mince organique qui contient un composé représenté par la formule (2).
PCT/JP2016/081318 2015-10-21 2016-10-21 Nouveau composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique WO2017069258A1 (fr)

Applications Claiming Priority (2)

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JP2015207014A JP2019023163A (ja) 2015-10-21 2015-10-21 新規化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器
JP2015-207014 2015-10-21

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WO2017069258A1 true WO2017069258A1 (fr) 2017-04-27

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019240470A1 (fr) * 2018-06-14 2019-12-19 주식회사 엘지화학 Composé et diode électroluminescente organique le comprenant
WO2019240473A1 (fr) * 2018-06-14 2019-12-19 주식회사 엘지화학 Composé et diode électroluminescente organique le comprenant
US11926603B2 (en) 2018-01-24 2024-03-12 Samsung Sdi Co., Ltd. Compound, composition, organic optoelectronic diode, and display device
US12010913B2 (en) 2019-10-02 2024-06-11 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, organic optoelectronic device and display device

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102456677B1 (ko) 2019-03-14 2022-10-19 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자

Citations (5)

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Publication number Priority date Publication date Assignee Title
WO2011139129A2 (fr) * 2010-05-06 2011-11-10 주식회사 두산 Compose à base de triphénylène comprenant une amine aromatique et élément électroluminescent le comprenant
JP2013536196A (ja) * 2010-08-20 2013-09-19 ユニバーサル ディスプレイ コーポレイション Ｏｌｅｄのためのビカルバゾール化合物
WO2013165192A1 (fr) * 2012-05-02 2013-11-07 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les contenant
JP2014096586A (ja) * 2012-11-12 2014-05-22 Universal Display Corp 遅延蛍光を示す有機電界発光デバイス
US20140264292A1 (en) * 2013-03-14 2014-09-18 Universal Display Corporation Host compounds for phosphorescent oleds and devices thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011139129A2 (fr) * 2010-05-06 2011-11-10 주식회사 두산 Compose à base de triphénylène comprenant une amine aromatique et élément électroluminescent le comprenant
JP2013536196A (ja) * 2010-08-20 2013-09-19 ユニバーサル ディスプレイ コーポレイション Ｏｌｅｄのためのビカルバゾール化合物
WO2013165192A1 (fr) * 2012-05-02 2013-11-07 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les contenant
JP2014096586A (ja) * 2012-11-12 2014-05-22 Universal Display Corp 遅延蛍光を示す有機電界発光デバイス
US20140264292A1 (en) * 2013-03-14 2014-09-18 Universal Display Corporation Host compounds for phosphorescent oleds and devices thereof

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11926603B2 (en) 2018-01-24 2024-03-12 Samsung Sdi Co., Ltd. Compound, composition, organic optoelectronic diode, and display device
WO2019240470A1 (fr) * 2018-06-14 2019-12-19 주식회사 엘지화학 Composé et diode électroluminescente organique le comprenant
WO2019240473A1 (fr) * 2018-06-14 2019-12-19 주식회사 엘지화학 Composé et diode électroluminescente organique le comprenant
CN111770920A (zh) * 2018-06-14 2020-10-13 株式会社Lg化学 化合物及包含其的有机发光器件
CN111770920B (zh) * 2018-06-14 2023-08-08 株式会社Lg化学 化合物及包含其的有机发光器件
US12010913B2 (en) 2019-10-02 2024-06-11 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, organic optoelectronic device and display device

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