JP2014024844A - ヘテロ環化合物、有機発光素子及び有機発光表示装置 - Google Patents
ヘテロ環化合物、有機発光素子及び有機発光表示装置 Download PDFInfo
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- JP2014024844A JP2014024844A JP2013150575A JP2013150575A JP2014024844A JP 2014024844 A JP2014024844 A JP 2014024844A JP 2013150575 A JP2013150575 A JP 2013150575A JP 2013150575 A JP2013150575 A JP 2013150575A JP 2014024844 A JP2014024844 A JP 2014024844A
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Abstract
Description
X1及びX2を含む5員環は、共鳴構造を有しており、前記5員環は、少なくとも1つのヘテロ原子を含んでいる。従って、X1及びX2いずれも炭素原子である場合は、存在しない。すなわち、X1及びX2は、互いに独立して、C(R12)−、−N−、−N(R13)−、−O−及び−S−のうち1種である。ただし、X1及びX2のうち少なくとも一つは、−N−、−N(R13)−、−O−または−S−である。
ヨードベンゼン22.0g(107.84mmol)、ビス(トリフェニルホスフィン)パラジウム(II)ジクロリド(PdCl2(PPh3)2)3.0g(4.31mmol)及びCuI 1.6g(8.63mmol)を、無水トルエンとジイソプロピルアミンとの混合物(無水トルエン:ジイソプロピルアミンとの体積比は5:1である)200mLに入れて常温で5分間撹拌した。その後、エチニルトリメチルシラン9.1ml(92.99mmol)を徐々に入れ、80℃で18時間撹拌した。反応が完了すると、蒸溜水150mLを入れ、塩化メチレン80mLずつで3回抽出して得た有機層を、硫酸マグネシウムを利用して乾燥させた後、溶媒を蒸発させて得た残留物をシリカゲル・カラムクロマトグラフィで分離精製し、中間体1(1)17.86g(102.46mmol、収率95.0%)を得た。生成された化合物をLC−MS(chromatography−mass spectroscopy)で確認した。
C11H14Si:M+175.09
中間体1(1)5.0g(28.7mmol)をテトラヒドロフラン(THF)50mLと混合し、THF中のフッ化テトラブチルアンモニウム(tetrabutylammonium fluoride)(1.0M)40mLを滴加した後で30分間撹拌した。前記反応液に水500mLを添加し、エチルエーテル30mLで3回抽出した。それによって得た有機層を、硫酸マグネシウムを利用して乾燥させ、溶媒を蒸発させて得た残留物を、シリカゲル・カラムクロマトグラフィで分離精製し、中間体1(2)2.8g(収率93%)を得た。生成された化合物をLC−MSで確認した。
C8H6:M+103.05
3−ブロモ−2−ヨード−フラン5.0g(18.39mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0)((Pd(PPh3)4)1.1g(0.92mmol)、CuI 130mg(0.92mmol)を入れて真空環境にした後、N2雰囲気を作り、THF 50mLを入れて撹拌する。トリエチルアミン7.69mL(55.18mmol)と、中間体1(2)2.25g(22.07mmol)とを徐々に滴加した後、N2、室温条件で2時間撹拌した。溶媒を、回転蒸発器を利用して除去し、反応液に水50mLを加えてエチルエーテル50mLで3回抽出した。集められた有機層を、硫酸マグネシウムを利用して乾燥させ、溶媒を蒸発して得られた残留物を、シリカゲル・カラムクロマトグラフィで分離精製し、中間体1(3)2.8g(収率61%)を得た。生成された化合物をLC−MSで確認した。
C12H7BrO:M+246.95
中間体1(3)3.0g(12.14mmol)、ジベンゾフランボロン酸3.86g(18.21mmol)、Pd(PPh3)4 700mg(0.61mmol)、K2CO3 5.03g(36.42mmol)を、THF 30.0mLと蒸溜水10.0mLとに溶解させた。120℃に温度を高めて還流しながら24hr撹拌した。反応液を室温に冷やした後、水50mLとジエチルエーテル50mLとで3回抽出した。集められた有機層を硫酸マグネシウムを利用して乾燥させ、溶媒を蒸発させて得られた残留物を、シリカゲル・カラムクロマトグラフィで分離精製し、中間体1(4)2.1g(収率49%)を得た。生成された化合物をLC−MSで確認した。
C24H14O2:M+335.10
中間体1(4)2.0g(5.98mmol)を塩化メチレン20.0mLに溶かし、トリフルオロ酢酸16.5mL(215.33mmol)を徐々に滴加して1時間室温で撹拌した。反応が終わると、水15.0mLとジエチルエーテル20.0mLとを反応液に添加して3回抽出した。集められた有機層を、硫酸マグネシウムを利用して乾燥させ、溶媒を蒸発させて得られた残留物を、シリカゲル・カラムクロマトグラフィで分離精製し、化合物11.9g(収率95%)を得た。生成された化合物をLC−MS及びNMRで確認した。
前記代表合成例の反応式3、反応式4、反応式5と同一の当量及び方法により、上記の化合物17種を合成した。
アノードとして、コーニング(Corning)社の15Ω/cm2(1,200Å)ITOガラス基板を50mm×50mm×0.7mmサイズに切り、イソプロピルアルコールと純水とを利用して、各5分間超音波洗浄した後、30分間紫外線を照射してオゾンに露出させて洗浄した後、それを真空蒸着装置に装着した。
正孔輸送層の形成時、NPBの代わりに、前記化合物2を使用し、発光層の形成時、青色蛍光ホストとして、DNAを使用し、青色蛍光ドーパントとして、4,4’‐ビス(2,2‐ジフェニルエテニル)‐1,1’‐ビフェニル(DPVBi)を使用したことを除き、実施例1と同一に行い、有機発光素子を製作した。
正孔輸送層の形成時、NPBの代わりに、前記化合物3を使用し、発光層の形成時、青色蛍光ホストとして、DNAを使用し、青色蛍光ドーパントとして、DPVBiを使用したことを除き、実施例1と同一に行い、有機発光素子を製作した。
正孔輸送層の形成時、NPBの代わりに、前記化合物4を使用し、発光層の形成時、青色蛍光ホストとして、DNAを使用し、青色蛍光ドーパントとして、DPVBiを使用したことを除き、実施例1と同一に行い、有機発光素子を製作した。
発光層の形成時、青色蛍光ホストとして、DNA、及び青色蛍光ドーパントとして、前記化合物5を、98:2の質量比で同時蒸着することにより、300Å厚の発光層を形成したことを除き、前記実施例1と同一の方法を利用して有機発光素子を製造した。
発光層の形成時、緑色リン光ホストとして、前記化合物12、及び緑色リン光ドーパントとして、Irppyを、91:9の質量比で同時蒸着することにより、300Å厚の発光層を形成し、前記発光層の上部に、2,9−ジメチル−4,7−ジフェニル−1,10−フェナントロリン(BCP)を蒸着し、50Å厚の正孔阻止層を形成したことを除き、前記実施例1と同一の方法を利用して有機発光素子を製造した。
発光層の形成時、緑色リン光ホストとして、前記化合物13を使用したことを除き、実施例6と同一に行い、有機発光素子を製作した。
発光層の形成時、緑色リン光ホストとして、前記化合物19を使用したことを除き、実施例6と同一に行い、有機発光素子を製作した。
発光層の形成時、緑色リン光ホストとして、前記化合物20を使用したことを除き、実施例6と同一に行い、有機発光素子を製作した。
発光層の形成時、緑色リン光ホストとして、前記化合物21を使用したことを除き、実施例6と同一に行い、有機発光素子を製作した。
発光層の形成時、緑色リン光ホストとして、化合物25を使用したことを除き、実施例6と同一に行い、有機発光素子を製作した。
発光層の形成時、緑色リン光ホストとして、化合物26を使用したことを除き、実施例6と同一に行い、有機発光素子を製作した。
発光層の形成時、緑色リン光ホストとして、化合物27を使用したことを除き、実施例6と同一に行い、有機発光素子を製作した。
発光層の形成時、緑色リン光ホストとして、化合物28を使用したことを除き、実施例6と同一に行い、有機発光素子を製作した。
発光層の形成時、緑色リン光ホストとして、化合物29を使用したことを除き、実施例6と同一に行い、有機発光素子を製作した。
発光層の形成時、緑色リン光ホストとして、化合物36を使用したことを除き、実施例6と同一に行い、有機発光素子を製作した。
発光層の形成時、緑色リン光ホストとして、化合物39を使用したことを除き、実施例6と同一に行い、有機発光素子を製作した。
発光層の形成時、緑色リン光ホストとして、化合物45を使用したことを除き、実施例6と同一に行い、有機発光素子を製作した。
発光層の形成時、緑色リン光ホストとして、化合物51を使用したことを除き、実施例6と同一に行い、有機発光素子を製作した。
発光層の形成時、緑色リン光ホストとして、化合物54を使用したことを除き、実施例6と同一に行い、有機発光素子を製作した。
発光層の形成時、青色蛍光ホストとして、DNA、及び青色蛍光ドーパントとして、DPVBiを、98:2の質量比で同時蒸着することにより、300Å厚の発光層を形成したことを除き、実施例5と同一の方法を利用して有機発光素子を製造した。
発光層の形成時、緑色リン光ホストとして、CBP、及び緑色リン光ドーパントとして、Irppyを、91:9の質量比で同時蒸着することにより、300Å厚の発光層を形成したことを除き、前記実施例6と同一の方法を利用して有機発光素子を製造した。
実施例1〜20による有機発光素子と、比較例1,2による有機発光素子とについて、PR650(Spectroscan)Source Measurement Unit(PhotoResearch社製)を利用して駆動電圧、発光輝度、発光効率及び寿命を評価し、その結果を下記表1に示した。
11:基板
13:第1電極
15:有機層
16:発光層
19:第2電極
Claims (20)
- 下記化学式1で表示される、ヘテロ環化合物。
X1及びX2は、互いに独立して、C(R12)−、−N−、−N(R13)−、−O−及び−S−からなる群より選択される1種であり、X1及びX2のうち少なくとも一つは、−N−、−N(R13)−、−O−又は−S−であり、
X3は、N(R21)−、−O−又は−S−であり、
R1、R2、R3、R4、R11、R12、R13及びR21は、互いに独立して、水素、重水素、ハロゲン、ヒドロキシル基、シアノ基、アミノ基、ニトロ基、カルボン酸基、置換又は非置換のC1−C30アルキル基、置換又は非置換のC2−C30アルケニル基、置換又は非置換のC2−C30アルキニル基、置換又は非置換のC1−C30アルコキシ基、置換又は非置換のC3−C30シクロアルキル基、置換又は非置換のC3−C30シクロアルケニル基、置換又は非置換のC6−C30アリール基、置換又は非置換のC6−C30アリールオキシ基、置換又は非置換のC6−C30アリールチオ基、置換又は非置換のC2−C30ヘテロアリール基、及び−N(Q1)(Q2)で表示される基からなる群より選択される1種(ここで、Q1及びQ2は、互いに独立して、水素、重水素、ハロゲン、ヒドロキシル基、シアノ基、アミノ基、ニトロ基、カルボン酸基、置換又は非置換のC1−C30アルキル基、置換又は非置換のC2−C30アルケニル基、置換又は非置換のC2−C30アルキニル基、置換又は非置換のC1−C30アルコキシ基、置換又は非置換のC3−C30シクロアルキル基、置換又は非置換のC3−C30シクロアルケニル基、置換又は非置換のC6−C30アリール基、置換又は非置換のC6−C30アリールオキシ基、置換又は非置換のC6−C30アリールチオ基、及び置換又は非置換のC2−C30ヘテロアリール基のうち1種である。)であり、
Lは、置換もしくは非置換のC6−C30アリーレン基、又は、置換もしくは非置換のC2−C30ヘテロアリーレン基であり、
nは、0〜3の整数であり、
A環は、置換もしくは非置換のC6−C30芳香族環、又は、置換もしくは非置換のC2−C30ヘテロ芳香族環であり、
R11及びR12は、選択的に互いに結合し、置換又は非置換のC6−C30芳香族環、又は、置換又は非置換のC2−C30ヘテロ芳香族環を形成することができる。 - A環が、置換または非置換のベンゼン環、置換または非置換のナフタレン環、置換または非置換のアントラセン環、置換または非置換のフェナントレン環、及び置換または非置換のピリジン環からなる群より選択される1種であることを特徴とする、請求項1又は2に記載のヘテロ環化合物。
- R11及びR12が互いに結合し、置換または非置換のベンゼン環を形成することを特徴とする、請求項1〜5のいずれか1項に記載のヘテロ環化合物。
- R1、R2、R3、R4、R11、R12、R13及びR21が、互いに独立して、水素、重水素、ハロゲン、ヒドロキシル基、シアノ基、アミノ基、ニトロ基、カルボン酸基、置換または非置換のメチル基、置換または非置換のエチル基、置換または非置換のプロピル基、置換または非置換のブチル基、置換または非置換のフェニル基、置換または非置換のビフェニル基、置換または非置換のナフチル基、置換または非置換のアントリル基、置換または非置換のフェナントレニル基、置換または非置換のピレニル基、置換または非置換のクリセニル基、置換または非置換のナフタセニル基、置換または非置換のフルオレニル基、置換または非置換のピリジニル基、置換または非置換のビピリジニル基、置換または非置換のピラジニル基、置換または非置換のピリミジニル基、置換または非置換のピリダジニル基、置換または非置換のキノリニル基、置換または非置換のイソキノリニル基、置換または非置換のカルバゾリル基、置換または非置換のベンゾチオフェニル基、置換またはo非置換のジベンゾチオフェニル基、置換または非置換のベンゾフラニル基、置換または非置換のジベンゾフラニル基、及び−N(Q3)(Q4)で表示される基(ここで、Q3及びQ4は、互いに独立して、置換または非置換のフェニル基、置換または非置換のビフェニル基、及び置換または非置換のナフチル基からなる群より選択される1種である。)からなる群より選択される1種であることを特徴とする、請求項1〜7のいずれか1項に記載のヘテロ環化合物。
- R2が、下記化学式5a〜化学式5iのうち1種で表示されることを特徴とする、請求項1〜7のいずれか1項に記載のヘテロ環化合物。
Z11〜Z14は、互いに独立して、水素、重水素、ハロゲン、シアノ基、置換または非置換のメチル基、置換または非置換のエチル基、置換または非置換のプロピル基、置換または非置換のブチル基、置換または非置換のメトキシ基、置換または非置換のエトキシ基、置換または非置換のプロポキシ基、置換または非置換のブトキシ基、置換または非置換のフェニル基、及び置換または非置換のビフェニル基からなる群より選択される1種であり、
r及びsは、互いに独立して、1〜5の整数であり、
*は、R2が、前記ヘテロ環化合物の残りの部分と結合される部位を示す。 - Lは、フェニレン基、ナフチレン基又はアントラセニレン基であり、nは、0又は1であることを特徴とする、請求項1〜9のいずれか1項に記載のヘテロ環化合物。
- 第1電極と、
前記第1電極に対向した第2電極と、
前記第1電極と前記第2電極との間に介在された有機層と、
を有し、
前記有機層が、請求項1〜11のいずれか1項に記載のヘテロ環化合物を含むことを特徴とする、有機発光素子。 - 前記有機層が、正孔注入層、正孔輸送層、正孔注入能及び正孔輸送能を同時に有する機能層、バッファ層、発光層、正孔阻止層、電子輸送層、電子注入層、並びに電子注入能及び電子輸送能を同時に有する機能層のうち少なくとも1層を含むことを特徴とする、請求項12に記載の有機発光素子。
- 前記有機層が、正孔注入層、正孔輸送層、並びに正孔注入能及び正孔輸送能を同時に有する機能層のうち少なくとも1層を含み、前記正孔注入層、正孔輸送層、並びに正孔注入能及び正孔輸送能を同時に有する機能層のうち少なくとも1層が、前記ヘテロ環化合物を含むことを特徴とする、請求項12に記載の有機発光素子。
- 前記有機層が、電子注入層、電子輸送層、並びに電子注入能及び電子輸送能を同時に有する機能層のうち少なくとも1層を含み、前記電子注入層、電子輸送層、並びに電子注入能及び電子輸送能を同時に有する機能層のうち少なくとも1層が、前記ヘテロ環化合物を含むことを特徴とする請求項12に記載の有機発光素子。
- 前記有機層が発光層を含み、前記発光層が、前記ヘテロ環化合物を含むことを特徴とする請求項12に記載の有機発光素子。
- 前記ヘテロ環化合物が、蛍光ホスト又はリン光ホストとして使用されることを特徴とする、請求項16に記載の有機発光素子。
- 前記ヘテロ環化合物が、蛍光ドーパントとして使用されることを特徴とする、請求項16に記載の有機発光素子。
- 前記有機層が、
発光層と、
電子注入層、電子輸送層、並びに電子注入能及び電子輸送能を同時に有する機能層のうち少なくとも1層と、を含み、
前記発光層と、前記電子注入層、電子輸送層、並びに電子注入能及び電子輸送能を同時に有する機能層のうち少なくとも1層と、のうち少なくとも1層が、前記ヘテロ環化合物を含み、前記発光層は、アリールアミン化合物を含むことを特徴とする、請求項12に記載の有機発光素子。 - ソース、ドレイン、ゲート及び活性層を含んだトランジスタ、並びに請求項12〜19のうちいずれか1項に記載の有機発光素子を備え、
前記有機発光素子の第1電極が、前記ソース及びドレインのうち一つと電気的に連結されたことを特徴とする、有機発光表示装置。
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JP2017031138A (ja) * | 2015-07-29 | 2017-02-09 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
JP2020511775A (ja) * | 2017-02-16 | 2020-04-16 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 有機エレクトロルミネセント化合物及びこれを含む有機エレクトロルミネセントデバイス |
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KR101740486B1 (ko) | 2017-05-29 |
KR20140013614A (ko) | 2014-02-05 |
DE102013214399A1 (de) | 2014-01-30 |
TW201410662A (zh) | 2014-03-16 |
TWI602813B (zh) | 2017-10-21 |
CN103570737A (zh) | 2014-02-12 |
US9893301B2 (en) | 2018-02-13 |
CN103570737B (zh) | 2017-09-05 |
JP6297274B2 (ja) | 2018-03-20 |
US20140027741A1 (en) | 2014-01-30 |
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