JP5095612B2 - 燐光発光ダイオードにおけるトリフェニレンホスト - Google Patents
燐光発光ダイオードにおけるトリフェニレンホスト Download PDFInfo
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- JP5095612B2 JP5095612B2 JP2008514776A JP2008514776A JP5095612B2 JP 5095612 B2 JP5095612 B2 JP 5095612B2 JP 2008514776 A JP2008514776 A JP 2008514776A JP 2008514776 A JP2008514776 A JP 2008514776A JP 5095612 B2 JP5095612 B2 JP 5095612B2
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- 0 CC(C)(C)c1ccc([*+])cc1 Chemical compound CC(C)(C)c1ccc([*+])cc1 0.000 description 5
- DLMYHUARHITGIJ-UHFFFAOYSA-N CCc1ccccc1-c1ccccc1 Chemical compound CCc1ccccc1-c1ccccc1 DLMYHUARHITGIJ-UHFFFAOYSA-N 0.000 description 2
- GLHQUXLCQLQNPZ-UHFFFAOYSA-N Brc(cc(c(c(c(cc1Br)c2cc1Br)c1)cc(Br)c1Br)c2c1)c1Br Chemical compound Brc(cc(c(c(c(cc1Br)c2cc1Br)c1)cc(Br)c1Br)c2c1)c1Br GLHQUXLCQLQNPZ-UHFFFAOYSA-N 0.000 description 1
- KTQYWNARBMKMCX-UHFFFAOYSA-N c(cc1)cc-2c1-c(cccc1)c1-c(cccc1)c1-c1ccccc-21 Chemical compound c(cc1)cc-2c1-c(cccc1)c1-c(cccc1)c1-c1ccccc-21 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- JNXCGJQUBVERSU-UHFFFAOYSA-N c(cc1)cc2c1c(cc(c(-c1cc3c(cccc4)c4c(cccc4)c4c3cc1-c1c3)c4)-c5cc6c(cccc7)c7c(cccc7)c7c6cc5-c1cc1c3c3ccccc3c3ccccc13)c4c1c2cccc1 Chemical compound c(cc1)cc2c1c(cc(c(-c1cc3c(cccc4)c4c(cccc4)c4c3cc1-c1c3)c4)-c5cc6c(cccc7)c7c(cccc7)c7c6cc5-c1cc1c3c3ccccc3c3ccccc13)c4c1c2cccc1 JNXCGJQUBVERSU-UHFFFAOYSA-N 0.000 description 1
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Description
Arはアリールおよび置換アリールから選択され;
Xは、1〜3であり;
Yは、1〜3であり;かつ
nは、1〜3である。
Xは、1〜3であり;
Yは、1〜3であり;かつ
nは、1〜3である。
R1、R2、R3およびR'は、それぞれ独立に、アリール、置換アリール、ヘテロアリール、置換へテロアリール、アルキル、アリールキル、ヘテロアルキル、アルケニル、およびアルキニルからなる群から選択される。
本明細書では、略語は以下の材料を表す。
CBP: 4,4'-N,N-ジカルバゾール-ビフェニル
m-MTDATA: 4,4',4"-トリス(3-メチルフェニルフェニルアミノ)トリフェニルアミン
Alq3: 8-トリス-ヒドロキシキノリンアルミニウム
Bphen: 4,7-ジフェニル-1,10-フェナントロリン
n-BPhen: n型ドープBPhen(リチウムでドープ)
F4-TCNQ: テトラフルオロ-テトラシアノ-キノジメタン
p-MTDATA: p型ドープm-MTDATA(F4-TCNQでドープ)
Ir(ppy)3: トリス(2-フェニルピリジン)-イリジウム
Ir(ppz)3: トリス(1-フェニルピラゾロト,N,C(2')イリジウム(III)
BCP: 2,9-ジメチル-4,7-ジフェニル-1,10-フェナントロリン
TAZ: 3-フェニル-4-(1'-ナフチル)-5-フェニル-1,2,4-トリアゾール
CuPc: 銅フタロシアニン
ITO: インジウムスズ酸化物
NPD: N,N'-ジフェニル-N-N'-ジ(l-ナフチル)-ベンジジン
TPD: N,N'-ジフェニル-N-N'-ジ(3-トリル)-ベンジジン
BAlq: アルミニウム(III)ビス(2-メチル-8-ヒドロキシキノリナト)4-フェニルフェノラート
mCP: 1,3-N,N-ジカルバゾール-ベンゼン
DCM: 4-(ジシアノメチレン)-6-(4-ジメチルアミノスチリル)-2-メチル-4H-ピラン
DMQA: N,N'-ジメチルキナクリドン
PEDOT:PSS ポリスチレンスルホン酸(PSS)によるポリ(3,4-エチレンジオキシチオフェン)の水性分散体
HPT: 2,3,6,7,10,11-ヘキサフェニルトリフェニレン
2,7-DCP: 2,7-N,N-ジカルバゾールフェナントレン
3,3'-DC-o-TerP: 3,3'-ジカルバゾール-o-ターフェニル
4,4'-DC-o-TerP: 4,4'-ジカルバゾール-o-ターフェニル
2,6'-DCN: 2,6-N,N-ジカルバゾールナフタレン
Ir(5-Phppy)3: トリス[5'-フェニル(2-フェニルピリジン)]イリジウム(III)
Ir(3-Meppy)3: トリス(3-メチル-2-フェニルピリジン)イリジウム(III)
Ir(1-piq)3: トリス(1-フェニルイソキノリン)イリジウム(III)
Ir(3-Mepq)2(acac): ビス[3-メチル-2-フェニルキノリン]イリジウム(III)アセチルアセトナート
Ir(5-Phppy)3: トリス[5-フェニル(2-フェニルピリジン)]イリジウム(III)
Ir(pq)2(acac): ビス[2-フェニルキノリン]イリジウム(III)アセチルアセトナート
2,2-BT: 2,2-ビストリフェニレン
HPT: 2,3,6,7,10,11-ヘキサフェニルトリフェニレン
H1NT: 2,3,6,7,10,11-ヘキサ(1-ナフチル)トリフェニレン
H2BT: 2,3,6,7,10,11-ヘキサ(2-ビフェニル)トリフェニレン
ステップ1. 2,3,6,7,10,11-ヘキサブロモトリフェニレンの調製
2,3,6,7,10,11-ヘキサブロモトリフェニレンを、文献の方法(Breslowら、Tetrahedron、1982、38、863)に従って調製した。トリフェニレン(3.0g、13.2mmol)を70mLのニトロベンゼンに溶かした。0.27gのFe粉末を加えた。この混合物に、20mLのニトロベンゼン中の臭素(18.6g、120mmol)を滴下漏斗により加えた。混合物を室温で12時間攪拌し、2時間還流させた。冷却後、固体を濾過し、エタノールにより洗い、乾燥した。8.9g(96%)の粗生成物を得た。沸騰1,2-ジクロロベンゼン(約180℃)からの再結晶により、オフホワイトの針状晶として生成物を得た(8.64g、94%)。この生成物は、質量分析によって確認した。
1,1-ビストリフェニレンは、Organometallics,2004,23,3079に従って合成できる。
ステップ1: 2-アミノトリフェニレンの合成
約100mLのエタノール中の3.1g(11.3mmol)の1および2-ニトロトリフェニレンの混合物(J.Chem.Soc., 1955, 4482に従って合成)、600mg(0.57mmol)のPd/C(活性炭上10%)、ならびに2.3g(45.2mmol)のヒドラジン一水和物を、250mLの丸底フラスコに投入した。この反応混合物を窒素下で2時間加熱還流した。次いで、反応混合物を濾過し、濾液を濃縮し、ヘキサン中25%の酢酸エチルを溶離液として用いてシリカゲルカラムに通した。1および2-アミノトリフェニレンを分離し、MSおよびNMRにより確認した。この反応の収率は100%であった。
〔ポリ(2-ビニルトリフェニレン)の調製〕
ポリ(2-ビニルトリフェニレン)は、当業者によって一般的に用いられる合成化学に基づく次のスキームによって合成できる。
ポリ[2-(4-ビニルフェニル)トリフェニレン]は、当業者によって一般的に用いられる合成化学に基づく次のスキームによって合成できる。
ポリ(2,7-トリフェニレン)は、当業者によって広く用いられる合成化学に基づく次のスキームによって合成できる。
ポリ(2,7-トリフェニレン-1,4-フェニレン)は、当業者によって広く用いられる合成化学に基づく次のスキームによって合成できる。
1,12-縮合テトラトリフェニレンは、次のスキームに従って合成できる。
すべてのデバイスは高真空(<10-7Torr)熱蒸着によって製造した。アノード電極は約1200Åのインジウムスズ酸化物(ITO)である。カソードは10ÅのLiFとそれに続く1,000ÅのAlとからなる。すべてのデバイスを、製造直後に、窒素グローブボックス(<1ppmのH2OおよびO2)内においてエポキシ樹脂で密封したガラス蓋(glass lid)で封じ、かつ吸湿剤をパッケージ内に組み込んだ。
有機積層体は、ITO表面から順次、ホール注入層(HIL)として100Åの厚さの銅フタロシアニン(CuPc)、ホール輸送層(HTL)として300Åの厚さの4,4'-ビス[N-(1-ナフチル)-N-フェニルアミノ]ビフェニル(α-NPD)、発光層(EML)として6ないし12wt%のドーパント発光体でドープされた300Åの厚さの、トリフェニレン化合物または比較化合物、で構成される。実施例デバイス1、4、7、10、13、16、および22、ならびに比較実施例デバイス1、2、3、および4は、ETL2として100〜150Åのアルミニウム(III)ビス(2-メチル-8-ヒドロキシキノリナト)4-フェニルフェノラート(BAlq)、およびETL1として400〜500Åのトリス(8-ヒドロキシキノリナト)アルミニウム(Alq3)で構成される。実施例デバイス2、5、8、11、14、19、20、21、および23、ならびに比較実施例デバイス5および6は、ETL2として50〜150ÅのHPT、およびETL1として400〜500ÅのAlq3で構成される。実施例デバイス3、6、9、12、15、および18は、ETL1なしで、ETL2として400〜500ÅのAlq3で構成される。正確なETL層の厚さを表2に示している。HPTおよび2,2-BTならびにホスト材料として適切であるトリフェニレン化合物の追加の例の構造を、図17に示している。
110 基板
115 アノード
120 ホール注入層
125 ホール輸送層
130 電子阻止層
135 発光層
140 ホール阻止層
145 電子輸送層(ETL)
150 電子注入層
155 保護層
160 カソード
162 第1導電層
164 第2導電層
200 倒置型OLED
210 基板
215 カソード
220 発光層
225 ホール輸送層
230 アノード
Claims (12)
- R2、R3、R6、R7、R10、およびR11がすべて同じである、請求項1に記載の発光層。
- R2、R3、R6、R7、R10、およびR11が、フェニル、ナフチルおよびビフェニルから選択される、請求項1に記載の発光層。
- R2、R3、R6、R7、R10、およびR11が、フェニル、ナフチルおよびビフェニルから選択される、請求項2に記載の発光層。
- 前記トリフェニレン化合物が、前記燐光材料のHOMOとLUMOのエネルギー準位の間のエネルギーギャップよりも大きな、そのHOMOとLUMOのエネルギー準位の間のエネルギーギャップを有する、請求項1に記載の発光層。
- 前記トリフェニレン化合物が、少なくとも1.8eVの、そのHOMOエネルギー準位とそのLUMOエネルギー準位の間のエネルギーギャップを有する、請求項1に記載の発光層。
- 前記トリフェニレン化合物が、前記燐光材料の最高被占分子軌道よりも低い最高被占分子軌道を有する、請求項1に記載の発光層。
- 前記トリフェニレン化合物が、前記燐光材料の最低空分子軌道よりも高い最低空分子軌道を有する、請求項1に記載の発光層。
- アノード、
カソード、
前記アノードと前記カソードとの間に配置された請求項1記載の発光層
を備える、有機エレクトロルミネセンスデバイス。 - 前記燐光材料が青色発光燐光材料である、請求項1に記載の発光層。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US68609405P | 2005-05-31 | 2005-05-31 | |
US60/686,094 | 2005-05-31 | ||
PCT/US2006/020954 WO2006130598A2 (en) | 2005-05-31 | 2006-05-31 | Triphenylene hosts in phosphorescent light emitting diodes |
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KR20140082808A (ko) | 2014-07-02 |
EP1888708A2 (en) | 2008-02-20 |
KR20130098434A (ko) | 2013-09-04 |
CN103746080A (zh) | 2014-04-23 |
US9139494B2 (en) | 2015-09-22 |
US20130001538A1 (en) | 2013-01-03 |
EP2277978A3 (en) | 2011-05-04 |
US20120032156A1 (en) | 2012-02-09 |
EP2277978A2 (en) | 2011-01-26 |
CN101203583A (zh) | 2008-06-18 |
JP2012080130A (ja) | 2012-04-19 |
KR101357475B1 (ko) | 2014-02-03 |
EP3064563B1 (en) | 2018-12-26 |
WO2006130598A3 (en) | 2007-07-05 |
WO2006130598A2 (en) | 2006-12-07 |
US20060280965A1 (en) | 2006-12-14 |
JP2008543086A (ja) | 2008-11-27 |
JP6077579B2 (ja) | 2017-02-08 |
EP2277978B1 (en) | 2016-03-30 |
JP2015109481A (ja) | 2015-06-11 |
KR20080013934A (ko) | 2008-02-13 |
JP5778046B2 (ja) | 2015-09-16 |
CN103435436A (zh) | 2013-12-11 |
US8092924B2 (en) | 2012-01-10 |
EP3064563A1 (en) | 2016-09-07 |
EP1888708B1 (en) | 2012-11-21 |
CN103746080B (zh) | 2019-03-08 |
US8580404B2 (en) | 2013-11-12 |
KR101634423B1 (ko) | 2016-06-28 |
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