TWI356092B - - Google Patents

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TWI356092B
TWI356092B TW094120826A TW94120826A TWI356092B TW I356092 B TWI356092 B TW I356092B TW 094120826 A TW094120826 A TW 094120826A TW 94120826 A TW94120826 A TW 94120826A TW I356092 B TWI356092 B TW I356092B
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Masakazu Funahashi
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Idemitsu Kosan Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/92—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/59—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/93—Spiro compounds
    • C07C2603/95—Spiro compounds containing "not free" spiro atoms
    • C07C2603/96—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members
    • C07C2603/97—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members containing five-membered rings
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

1356092 »« 民國103年1月24曰更正 * 第 094120826 號 (―般式（2)中’ Ri，R2，A,〜A4及a〜d係各與前 述相同’ a〜d之各爲2以上之情形，Al〜A4各自可爲相 同或相異，可互相鍵結形成飽和或不飽和之環。又，、與 Μ，A3與A4可各自鍵結形成飽和或不飽和之環。 但是，一般式（2)中，心及R2無均爲氫原子之情形 ’ Ai〜A4中至少之一爲取代或者無取代之碳數3τ<10之2 級或3級烷基。）
(3) Ο (―般式（3)中，Ri，R2，Ai〜A4及a〜d各與前述 相同，a〜d之各爲2以上之情形，At〜A4可各自爲相同 或相異，可互輝鍵結形成飽和或不飽和之環。又，A,與 A2，A3與A4各自可鍵結形成飽和或不飽和之環。 但是，一般式（3)中，1^及R2無均爲氫原子之情形 ’ a〜d中至少之一爲2以上之整數。） -8- 1356092 ‘ 第094120826號 民國103年1月24日更正
(—般式（4)中’ Ri’ R2，Αι〜A4及a〜d各與前述 相同’ a〜d之各爲2以上之情形，a!〜A4各自可爲相同 或相異，可互相鍵結形成飽和或不飽和之環。又，Al與 A2，A3與A4可各自鍵結形成飽和或不飽和之環。 但是’一般式（4)中，Ri及/或R2爲取代或者無取 代之碳數3〜10之2級或3級烷基，無人1〜八4全部爲氫 原子之情形。） 又，本發明係提供在陰極與陽極間夾持至少含發光層 之一層或多層所成有機薄膜層之有機EL元件中，該有機 薄膜層之至少1層，含有以該芳香族胺衍生物爲單獨或混 合物之成分之有機EL元件，以及， 在陰極與陽極間夾持至少含發光層之一層或多層所成 有機薄膜層之有機EL元件中，在該陽極與該發光層之間 含有以該芳香族胺衍生物爲主成分之有機層之有機EL元 件。 1356092 民國103年1月24 日更正 ’ 第 094120826 號
—败式C1)〜（4)中，Ri及R2係氫原子，取代或 .者無取代之碳數1〜50(較佳爲碳數1〜2〇)之烷基，取 代或者無取代之碳數5〜5〇(較佳爲碳數5〜2〇)之芳基 ，取代或者無取代之碳數1〜50 (較佳爲碳數9〜20)之 方烷基，取代或者無取代之碳數3〜5〇(較佳爲碳數5〜 12)之環烷基，取代或者無取代之碳數較佳爲碳 數1〜6)之烷氧基，取代或者無取代之碳數5〜5〇 (較佳 爲碳數5〜18)之方氧基，取代或者無取代之碳數$〜5〇 (較佳爲碳數5〜18)之芳胺基，取代或者無取代之碳數1 〜2〇 (較佳爲碳數！〜6)之烷胺基或_原子。 該Ri及心之院基方面，可例舉例如甲基，乙基，丙 基，異丙$，丁基，二級丁基，三級丁基，戊基，己基， -11 - 1356092 民國103年1月24日更正 ‘ 第 094120826 號 ，三級丁氧基，各種戊氧基，各種己氧基等。 該R!及R2之芳氧基方面，可例舉例如苯氧基’甲苯 氧基，萘氧基等。 該1^及R2之芳胺基方面，可例舉例如二苯基氨基’ 二甲苯氨基，異丙基二苯基氨基，三級丁基二苯基氨基’ 二異丙基二苯基氨基，二-三級丁基二苯基氨基，二萘基 氨基，萘基苯基氨基等。 @ 該Ri及之烷胺基方面，可例舉例如二甲基氨基， 一乙基氨基，二己基氨基等。 該I及R2之鹵原子方面，可例舉例如氟原子，氯原 子’溴原子等。 以上之中以，1^及方面，以甲基，乙基，丙基， 異丙基，丁基，二級丁基，三級丁基，環戊基，環己基， 本基，萘基，4·甲基苯基爲佳，以甲基’乙基，丙基，異 丙基，環己基，苯基，萘基進而爲佳。 〇 —般式（1)〜（4)中，Al〜A4係各自獨立，爲氫原 子取代或者無取代之碳冑^50(較佳爲碳冑卜2〇) 之院基，取代或者無取代之碳數5〜5〇(較佳爲碳數5〜 2〇)之芳基，取代或者無取代之碳數〗〜5。（較佳爲碳數 9〜2〇)之芳院基，取代或者無取代之碳數卜 碳數5〜⑴之環院基，取代或者無取代之碳冑 較佳爲碳數！〜6)之烷氧 數5〜5〇(較佳爲碳數5〜丨8)之 5。(較佳爲碳數5〜18)之芳無取代之碳數卜 敷18)之方氧基，取代或者無取代之碳 芳胺基，取代或者並 -13- 1356092 •.第 094120826 號 民國103年1 代之碳數1〜20 (較佳爲碳數1〜6)之烷胺基 無取代之砂院基，或鹵原子。 該等之中以氫原子取代或者無取代之碳數 基，取代或者無取代之碳數5〜2〇之芳基，取 代之碳數1〜20之芳烷基，取代或者無取代之 之環烷基，取代或者無取代之矽烷基爲佳以 或者無取代之碳數1〜4之烷基，取代或者無拓 〜18之芳基’取代或者無取代之碳數1〜“之 或者無取代之碳數3〜6之環烷基’取代或者 院基進而爲佳。 又’ Αι〜A*之至少之一爲取代或者無取代 佳。 該Αι〜A4之烷基、芳基、芳烷基、環烷 、芳氧基、芳胺基、烷胺基及鹵原子之具體例 與該及r2所舉者各自相同之物。 該Ai〜A4之矽烷基方面，可例舉例如三 ’三乙基矽烷基，三級丁基二甲基矽烷基，乙 院基’丙基二甲基矽烷基，甲基二苯基矽烷基 基砂院基，三苯基矽烷基等。 a〜d係各自〇〜5之整數，以〇〜3爲佳， 而爲佳。 a〜d各爲2以上之情形，複數之A!〜A4 相同或相異，可互相鍵結形成飽和或不飽和之 # Ay a3與人4可各自鍵結形成飽和或不飽和 ^ 24臼更正 ’取代或者 1〜之烷 代或者無取 碳數3〜1 〇 氫原子取代 ^代之碳數5 芳烷基取代 無取代之矽 之矽烷基爲 基、烷氧基 方面，可舉 甲基矽烷基 烯二甲基矽 ，二甲基苯 以0〜2進 可各自互爲 環。又，A1 之環。 -14- 1356092
β * » I ' 第094120826號 民國103年1月24日更正 但是，一般式（1)中，1及R2無均爲氫原子之情形 ’無A!〜A4全部爲氫原子之情形 又’ _般式（2)中，_1^及112無均爲氫原子之情形， Al〜A4中至少之一爲取代或者無取代之碳數3〜1〇之2級 或3級烷基。 又，一般式（3)中，1^及R2無均爲氫原子之情形， a〜d中至少之一爲2以上之整數。 @ 又，—般式（4)中，Ri及/或爲取代或者無取代 之碳數3〜10之2級或3級烷基，無Ai〜a4全部爲氯原 子之情形。 本發明之一般式（1)〜（4)所示之芳香族胺衍生物 之具體例如以下所示，但並非限定於該等例示化合物。Me 表示甲基。 〇 -15- 1356092 *1 民國103年1月·24日更正 • 第 094120826 號 (—般式（5)中，γ 1及X2係各自獨立，氫辟 代或者無取代之碳數1〜-之院基，取代或者無取代之: 碳數5〜5〇之方基，取代或者無取代之核碳數6〜5〇之芳 院基’取代或者無取代之核碳數3〜5〇之環院基取代或 者無取代之碳數1〜^ 之烷氧基，取代或者無取代之核碳 Θ 數5〜50之芳氧基，取代或者無取代之核碳數5〜μ之芳 胺基，取代或者無取代之碳數卜20之烷胺基，取代或者 無取代之核碳數5〜50之雜環基，或鹵原子，e，f係各自 獨立，爲0〜4之整數。…爲2以上之情形，Xl，又2各 自可爲相同或相異。 ΑΠ及AO係各自獨立’爲取代或者無取代之核碳數5 〜50之芳基’取代或者無取代之核碳數5〜5〇之雜環基， An及Ao之至少一個，係取代或者無取代之核碳數1〇〜 50之含縮合環之芳基。 m爲1〜3之整數。m爲2以上之情形，〔〕內之基 〇 ，可爲相同或相異。） 該Χι及X2以及Ar2之各基具體例或取代基可 舉與前述相同之例。 -22- 丄 που% 丄 που% 民國103年丨月糾日更正
第 094120826 號 · ， (―般式（6)中，父 v AT ^
Xl〜X3係各自獨立，爲氫原子， 取代或者無取代之碳數丨〜 之院基’取代或者 核碳數5〜50之芳基，趵你十土 4否…、取代之 一 之方基取代或者無取代之核碳數6〜5〇之 方院基’取代或者取代夕坊α 否…、取代之核碳數3〜5〇之環烷基取代 或者無取代之碳數1〜5〇之院氧基，取 氧悬取代或者無取代之核 〇碳數5〜5。之方氧基，取代或者無取代之核碳數5〜⑶之 方胺基取代或者無取代之碳數^20之院胺基取代或 者無取代之核碳數5〜5〇之雜環基，或鹵原子，e，f及居 係各自獨1L爲〇〜4之整數。e，f’ g爲2以上之情形，χ丨 ，X2 ’ Χ3可各自爲相同或相異。
Ah係取代或者無取代之核碳數1〇〜5〇之含縮合環芳 基’ An係取代或者無取代之核碳數$〜5〇之芳基。 η爲1〜3之整數。„爲2以上之情形，〔〕內之基可 爲相同或相異。） 該Χ|〜乂3以及八^及Ar3之各基之具體例或取代基可 -23-
TW094120826A 2004-06-28 2005-06-22 Aromatic amine derivative and organic electroluminescent element using the same TW200606235A (en)

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TWI356092B true TWI356092B (zh) 2012-01-11

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US (2) US7470472B2 (zh)
EP (1) EP1762562A4 (zh)
JP (1) JP4951341B2 (zh)
KR (1) KR101173714B1 (zh)
CN (1) CN1906153B (zh)
TW (1) TW200606235A (zh)
WO (1) WO2006001223A1 (zh)

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JP4951341B2 (ja) 2004-06-28 2012-06-13 出光興産株式会社 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子
JP2006306745A (ja) * 2005-04-26 2006-11-09 Idemitsu Kosan Co Ltd 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子
JP2009001788A (ja) * 2007-05-23 2009-01-08 Sumitomo Chemical Co Ltd 高分子化合物及びその製造方法、並びに、その高分子化合物を用いた発光材料、液状組成物、薄膜、高分子発光素子、面状光源、表示装置、有機トランジスタ及び太陽電池
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WO2006001223A1 (ja) 2006-01-05
US7470472B2 (en) 2008-12-30
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CN1906153B (zh) 2012-07-04
US20060177693A1 (en) 2006-08-10
CN1906153A (zh) 2007-01-31
US20090058284A1 (en) 2009-03-05
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JP4951341B2 (ja) 2012-06-13

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