JP2019073489A - 有機エレクトロルミネッセンス素子及び材料 - Google Patents
有機エレクトロルミネッセンス素子及び材料 Download PDFInfo
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- Electroluminescent Light Sources (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
(製法1)下記式(S−1)で表される化合物の製造
式(S−1−1)で表される化合物を式(S−1−2)で表される化合物と反応させることにより式(S−1−3)で表される化合物を得る。反応条件としては、金属触媒及び塩基存在下、クロスカップリングさせる方法が挙げられる。金属触媒としては例えば、ビス(ジベンジリデンアセトン)パラジウム(0)、[1,1’−ビス(ジフェニルホスフィノ)フェロセン]パラジウム(II)ジクロリド、ビス(トリフェニルホスフィン)パラジウム(II)ジクロリド、テトラキス(トリフェニルホスフィン)パラジウム(0)等のパラジウム触媒が挙げられる。塩基としては例えばトリエチルアミン、炭酸カリウム、炭酸セシウム等が挙げられる。反応条件の具体例としては、Metal−Catalyzed Cross−Coupling Reactions(Armin de Meijere、Francois Diedrich共著、Wiley−VCH)、Palladium Reagents and Catalysts:New Perspectives for the 21st Century(Jiro Tsuji著、Wiley & Sons,Ltd.)、Cross−Coupling Reactions:A Practical Guide(Topics in Current Chemistry)(S.L.Buchwald、K.Fugami、T.Hiyama、M.Kosugi、M.Miura、N.Miyaura、A.R.Muci、M.Nomura、E.Shirakawa、K.Tamao著、Springer)等の文献に記載の条件が挙げられる。
(実施例1)式(I−1)で表される化合物の製造
1H NMR(CDCl3)δ 0.67(m,4H),0.81(t,6H),1.05−1.20(m,20H),2.00(dd,4H),7.16(m,4H),7.31(m,4H),7.49−7.76(m,13H),7.90(s,1H)ppm
LCMS:737[M+1]
(実施例2)式(I−2)で表される化合物の製造
1H NMR(CDCl3)δ 0.62(m,4H),0.78(m,6H),1.02−1.22(m,20H),1.98(dd,4H),7.35(m,3H),7.56(m,2H),7.65−7.81(m,10H),8.08(dd,4H)ppm
LCMS:708[M+1]
(実施例3)式(I−3)で表される化合物の製造
LCMS:615[M+1]
(実施例4)式(I−4)で表される化合物の製造
LCMS:617[M+1]
(実施例5)式(I−5)で表される化合物の製造
LCMS:595[M+1]
(実施例6)式(I−6)で表される化合物の製造
LCMS:835[M+1]
(実施例7)式(I−7)で表される化合物の製造
LCMS:640[M+1]
(実施例8)式(I−8)で表される化合物の製造
LCMS:994[M+1]
(実施例9)式(I−9)で表される化合物の製造
LCMS:774[M+1]
(実施例10)式(I−10)で表される化合物の製造
LCMS:879[M+1]
(実施例11から実施例20及び比較例1から4)
実施例1から実施例10に記載の式(I−1)から式(I−10)で表される化合物及び非特許文献1記載の化合物(R−1)、非特許文献2記載の化合物(R−2)、非特許文献3記載の化合物(R−3)及び非特許文献4記載の化合物(R−4)を評価対象の化合物とした。
(実施例21から実施例30)
膜厚150nmのITO(インジウムスズオキシド)からなる陽極を有するガラス基板上に、PEDOT:PSSの70%水溶液をスピンコート法を用いて塗布し、200℃で1時間乾燥させることにより膜厚20nmの塗膜を得た。次に、真空度5.0×10−4Paで、α−NPD(100nm)を蒸着した。評価対象の化合物とADNを、評価対象の化合物の濃度が5.0%となるよう、異なる蒸着源から25nmの厚さで共蒸着した。次に、TPBI(25nm)、Liq(0.5nm)及びアルミニウム(80nm)を順に蒸着し、評価対象の有機エレクトロルミネッセンス素子を得た。
2,陽極
3,ホール注入層
4,ホール輸送層
5,発光層
6,電子輸送層
7,陰極
Claims (19)
- 下記の一般式(I)
- 励起一重項エネルギ−(ES1)と励起三重項エネルギ−(ET1)のエネルギー差(ΔEST)が0.01eVから0.40eVである、請求項1に記載の化合物。
- X1が下記の式(X−1)から式(X−5)
- 一般式(I)で表される化合物が下記の一般式(I−i)、一般式(I−ii)又は一般式(I−iii)
- AA1、AA2、AA3、AD1、AD2及びAD3に含まれるπ電子数が各々独立して8以上である、請求項4に記載の化合物。
- ZA1、ZA2、ZA3、ZD1、ZD2及びZD3が単結合を表す、請求項4又は請求項5のいずれか一項に記載の化合物。
- AA1、AA2及びAA3が下記の式(AA−1)から式(AA−14)
- AD1、AD2及びAD3が下記の式(AD−1)から式(AD−14)
- 一般式(I)で表される化合物が下記の一般式(I−i−1)、一般式(I−ii−1)又は一般式(I−iii−1)
- 請求項1から請求項10のいずれか一項に記載の化合物を含有する組成物。
- 請求項1から請求項10のいずれか一項に記載の化合物を含有する発光材料用組成物。
- 請求項1から請求項10のいずれか一項に記載の化合物を部分構造として有する重合体。
- 請求項13に記載の重合体を含有する発光材料用組成物。
- 陽極及び陰極により挟持された発光層を有する有機エレクトロルミネッセンス素子であって、
前記発光層が請求項1から請求項10のいずれか一項に記載の化合物、又は、請求項11から請求項14のいずれか一項に記載の組成物又は重合体を含むことを特徴とする有機エレクトロルミネッセンス素子。 - 発光層がさらにホスト材料を含有する、請求項15に記載の有機エレクトロルミネッセンス素子。
- 請求項1から請求項10のいずれか一項に記載の化合物を使用した樹脂、樹脂添加剤、オイル、フィルター、接着剤、粘着剤、油脂、インキ、医薬品、化粧品、洗剤、建築材料、包装材、液晶材料、有機EL材料、有機半導体材料、電子材料、表示素子、照明素子、電子デバイス、通信機器、自動車部品、航空機部品、機械部品、電子部品、試薬、農薬及び食品。
- 請求項15又は請求項16のいずれか一項に記載の有機エレクトロルミネッセンス素子を備えたことを特徴とする表示装置。
- 請求項15又は請求項16のいずれか一項に記載の有機エレクトロルミネッセンス素子を備えたことを特徴とする照明装置。
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Cited By (1)
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---|---|---|---|---|
CN111875636A (zh) * | 2020-08-05 | 2020-11-03 | 西北工业大学 | 基于氧化苯并噻吩的柔性有机摩擦发光材料及制备和使用方法 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07138560A (ja) * | 1993-11-15 | 1995-05-30 | Toshiba Corp | 光機能有機薄膜素子 |
WO2016017514A1 (ja) * | 2014-07-31 | 2016-02-04 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、発光性薄膜、表示装置及び照明装置 |
KR20160064956A (ko) * | 2014-11-28 | 2016-06-08 | 엘지디스플레이 주식회사 | 지연 형광 화합물, 이를 포함하는 유기발광다이오드소자 및 표시장치 |
WO2017011531A2 (en) * | 2015-07-13 | 2017-01-19 | President And Fellows Of Harvard College | Organic light-emitting diode materials |
WO2017115753A1 (ja) * | 2015-12-28 | 2017-07-06 | コニカミノルタ株式会社 | 架橋化合物、有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
WO2017115608A1 (ja) * | 2015-12-28 | 2017-07-06 | コニカミノルタ株式会社 | π共役系化合物、有機エレクトロルミネッセンス素子材料、発光材料、電荷輸送材料、発光性薄膜、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
CN107011269A (zh) * | 2017-04-24 | 2017-08-04 | 华南理工大学 | 可采用环境友好溶剂加工的以螺芴单元为核的双极性小分子发光材料及其制备方法与应用 |
-
2017
- 2017-10-19 JP JP2017202615A patent/JP2019073489A/ja active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07138560A (ja) * | 1993-11-15 | 1995-05-30 | Toshiba Corp | 光機能有機薄膜素子 |
WO2016017514A1 (ja) * | 2014-07-31 | 2016-02-04 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、発光性薄膜、表示装置及び照明装置 |
KR20160064956A (ko) * | 2014-11-28 | 2016-06-08 | 엘지디스플레이 주식회사 | 지연 형광 화합물, 이를 포함하는 유기발광다이오드소자 및 표시장치 |
WO2017011531A2 (en) * | 2015-07-13 | 2017-01-19 | President And Fellows Of Harvard College | Organic light-emitting diode materials |
WO2017115753A1 (ja) * | 2015-12-28 | 2017-07-06 | コニカミノルタ株式会社 | 架橋化合物、有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
WO2017115608A1 (ja) * | 2015-12-28 | 2017-07-06 | コニカミノルタ株式会社 | π共役系化合物、有機エレクトロルミネッセンス素子材料、発光材料、電荷輸送材料、発光性薄膜、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
CN107011269A (zh) * | 2017-04-24 | 2017-08-04 | 华南理工大学 | 可采用环境友好溶剂加工的以螺芴单元为核的双极性小分子发光材料及其制备方法与应用 |
Non-Patent Citations (6)
Title |
---|
CHAN,K.L. ET AL: "Understanding the nature of the states responsible for the green emission in oxidized poly(9,9-dialk", ADVANCED FUNCTIONAL MATERIALS, vol. 19, no. 13, JPN6021044647, 2009, pages 2147 - 2154, XP072360946, ISSN: 0004634340, DOI: 10.1002/adfm.200801792 * |
FANG, MEI; HUANG, JINJIN; ZHANG, YAN; GUO, XIN; ZHANG, XINWEN; LIU, CHENG-FANG; LAI, WEN-YONG; HUANG: "Pyrene-centered cyanophenyl end-capped starbursts: design, synthesis, stabilized blue electrolumines", MATERIALS CHEMISTRY FRONTIERS, vol. 1(4),, JPN6021026687, 2017, pages 668 - 676, ISSN: 0004634339 * |
FRANCO, IGNACIO; TRETIAK, SERGEI: "Electron-vibrational relaxation of photoexcited polyfluorenes in the presence of chemical defects: A", CHEMICAL PHYSICS LETTERS, vol. 372(3,4),, JPN6021026689, 2003, pages 403 - 408, ISSN: 0004634338 * |
JARAMILLO-ISAZA, FRANKLIN; TURNER, MICHAEL L.: "Synthesis and properties of conjugated oligomers containing fluorene, fluorenone, thiophene and cycl", JOURNAL OF MATERIALS CHEMISTRY, vol. 16(1),, JPN6021026691, 2006, pages 83 - 89, ISSN: 0004634337 * |
LIN, YING; CHEN, YU; YE, TENG-LING; CHEN, ZHI-KUAN; DAI, YAN-FENG; MA, DONG-GE: "Oligofluorene-based push-pull type functional materials for blue light-emitting diodes", JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY, A: CHEMISTRY, vol. 230(1),, JPN6021026692, 2012, pages 55 - 64, ISSN: 0004634336 * |
PARK, IN SEOB; SEO, HONGWOOK; TACHIBANA, HIROKI; KIM, JOUNG UK; ZHANG, JINBO; SON, SE MO; YASUDA, TA: "Cyclohexane-Coupled Bipolar Host Materials with High Triplet Energies for Organic Light-Emitting Dio", ACS APPLIED MATERIALS & INTERFACES (, vol. 9(3),, JPN6021026695, 2017, pages 2693 - 2700, ISSN: 0004634335 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111875636A (zh) * | 2020-08-05 | 2020-11-03 | 西北工业大学 | 基于氧化苯并噻吩的柔性有机摩擦发光材料及制备和使用方法 |
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