JP2019522676A - 有機電子素子用化合物、それを用いた有機電子素子及びその電子装置 - Google Patents
有機電子素子用化合物、それを用いた有機電子素子及びその電子装置 Download PDFInfo
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- JP2019522676A JP2019522676A JP2019513727A JP2019513727A JP2019522676A JP 2019522676 A JP2019522676 A JP 2019522676A JP 2019513727 A JP2019513727 A JP 2019513727A JP 2019513727 A JP2019513727 A JP 2019513727A JP 2019522676 A JP2019522676 A JP 2019522676A
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- SOSIJULCFHJNTI-UHFFFAOYSA-N triphenyleno[2,1-b]thiophene Chemical compound C1=CC=CC2=C3C(C=CS4)=C4C=CC3=C(C=CC=C3)C3=C21 SOSIJULCFHJNTI-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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Abstract
Description
R1、R2及びR3は、互いに独立して、水素;重水素;C6〜C60のアリール基;フルオレニル基;O、N、S、Si及びPの少なくとも一つのヘテロ原子を含むC2〜C60のヘテロ環基;C3〜C60の脂肪族環とC6〜C60の芳香族環との縮合環基;C1〜C50のアルキル基;C2〜C20のアルケニル基;C2〜C20のアルキニル基;C2〜C20のアルコキシル基;C6〜C30のアリールオキシ基及び−Lb−NAr3Ar4;からなる群から選ばれ、但し、R1、R2、R3中の一つは、−Lb−NAr3Ar4であり、
R4、R5、R6及びR7は、互いに独立して、水素;重水素;C6〜C60のアリール基;フルオレニル基;O、N、S、Si及びPの少なくとも一つのヘテロ原子を含むC2〜C60のヘテロ環基;C3〜C60の脂肪族環とC6〜C60の芳香族環との縮合環基;C1〜C50のアルキル基;C2〜C20のアルケニル基;C2〜C20のアルキニル基;C2〜C20のアルコキシル基及びC6〜C30のアリールオキシ基;からなる群から選ばれ、
隣接するR1とR2、隣接するR2とR3、隣接するR3とR4、隣接するR5とR6、隣接するR6とR7は、互いに独立して、互いに結合して芳香環又はヘテロ芳香環を形成していてもよく、
Ar1、Ar2、Ar3及びAr4は、互いに独立して、C6〜C60のアリール基;フルオレニル基;O、N、S、Si及びPの少なくとも一つのヘテロ原子を含むC2〜C60のヘテロ環基;C3〜C60の脂肪族環とC6〜C60の芳香族環との縮合環基;C1〜C50のアルキル基;C2〜C20のアルケニル基;C2〜C20のアルキニル基;C2〜C20のアルコキシル基;及びC6〜C30のアリールオキシ基;からなる群から選ばれ、但し、Ar1、Ar2、Ar3及びAr4の少なくとも一つは、下記一般式(1−1)
R8及びR9は、互いに独立して、水素;重水素;C6〜C60のアリール基;フルオレニル基;O、N、S、Si及びPの少なくとも一つのヘテロ原子を含むC2〜C60のヘテロ環基;C3〜C60の脂肪族環とC6〜C60の芳香族環との縮合環基;C1〜C50のアルキル基;C2〜C20のアルケニル基;C2〜C20のアルキニル基;C2〜C20のアルコキシル基;及びC6〜C30のアリールオキシ基;からなる群から選ばれ、又は、前記n、mが2以上の場合、それぞれ複数であって同じであるか、異なり、複数のR8同士あるいは複数のR9同士が互いに結合して、芳香環又はヘテロ芳香環を形成していてもよく、
nは、0〜3の整数、mは、0〜4の整数である}
で示される置換基となり、
La及びLbは、互いに独立して、単結合;C6−C60のアリーレン基;フルオレニレン基;C3〜C60の脂肪族環とC6〜C60の芳香族環との縮合環基;及びC2−C60のヘテロ環基;からなる群から選ばれ、
ここで、前記アリール基、フルオレニル基、アリーレン基、ヘテロ環基、縮合環基、アルキル基、アルケニル基、アルコキシ基及びアリールオキシ基は、それぞれ、重水素;ハロゲン;C1〜C20のアルキル基又はC6〜C20のアリール基で置換又は非置換されたシラン基;シロキサン基;C1〜C20のアルキルチオ基;C1〜C20のアルコキシル基;C1〜C20のアルキル基;C2〜C20のアルケニル基;C2〜C20のアルキニル基;C6〜C20のアリール基;重水素で置換されたC6〜C20のアリール基;フルオレニル基;C2〜C20のヘテロ環基;C3〜C20のシクロアルキル基;C7〜C20のアリールアルキル基及びC8〜C20のアリールアルケニル基からなる群から選ばれた一つ以上の置換基でさらに置換されていてもよく、また、これらの置換基は、互いに結合して、環を形成していてもよく、ここで「環」とは、C3〜C60の脂肪族環又はC6〜C60の芳香族環又はC2〜C60のヘテロ環又はこれらの組み合わせからなる縮合環を意味し、飽和又は不飽和環を含む。]
本発明に係る一般式(1)で示される化合物(final products1)は、下記の反応スキーム1のように、Sub1またはSub2が反応して合成されているが、これに限定されるものではない。
前記反応スキーム1のSub1は、下記反応スキーム2の反応経路によって合成されるが、これに限定されるものではない。
(2−ブロモ−6−ヨードフェニル)(エチル)スルファン(33g、96.20mmol)に(2−クロロフェニル)ボロン酸(15.04g、96.20mmol)、Pd(PPh3)4(3.34g、2.89mmol)、NaOH(7.70g、192.41mmol)、THF(300mL)、H2O(150mL)を添加し、90℃で12時間還流した。反応が終了すれば、反応物の温度を室温に冷却し、、MC(塩化メチレン)で抽出し、水で洗浄した。有機層をMgSO4で乾燥し、濃縮した後、生成された有機物をシリカゲルカラムを利用して分離して、生成物28.05g(89%)を得た。
Sub1−7−a(14g、42.73mmol)に酢酸(140mL)を添加し、35%過酸化水素(H2O2)(4.36g)を添加し、室温で撹拌した。反応が終了すれば、NaOH水溶液で中和させた後、EA(酢酸エチル)で抽出し、水で洗浄した。有機層をMgSO4で乾燥し、濃縮した後、生成された有機物をシリカゲルカラムを利用して分離して、生成物14.10g(96%)を得た。
Sub1−7−b(8.8g、25.61mmol)に硫酸(H2SO4)(50mL)を添加し、室温で撹拌した。反応が終了すれば、NaOH水溶液で中和させた後、MCで抽出し、水で洗浄した。有機層をMgSO4で乾燥し、濃縮した後、生成された有機物をシリカゲルカラムを利用して分離して、生成物5.64g(74%)を得た。
Sub1−7−c(9.10g、30.58mmol)にSub2−43(10.75g、30.58mmol)、Pd2(dba)3(0.84g、0.92mmol)、NaOt−Bu(5.88g、61.16mmol)、P(t−bu)3(0.62g、3.06mmol)、トルエン(100mL)を添加し、80℃で4時間還流した。反応が終了すれば、反応物の温度を室温に冷却し、MCで抽出し、水で洗浄した。有機層をMgSO4で乾燥し、濃縮した後、生成された有機物をシリカゲルカラムを利用して分離して、生成物15.98g(92%)を得た。
2−ブロモ−6−ヨードフェノール(19.5g、65.24mmol)に(2−クロロフェニル)ボロン酸(10.20g、65.24mmol)、Pd(PPh3)4(2.26g、1.96mmol)、NaOH(5.22g、130.47mmol)、THF(200mL)、H2O(100mL)を前記Sub1−7−aの合成法を用いて、生成物13.32g(72%)を得た。
Sub1−18−d(12.2g、43.03mmol)にPd(OAc)2(0.48g、2.15mmol)、3−ニトロピリジン(0.27g、2.15mmol)、BzOOtBu(tert−ブチルパーオキシベンゾエート)(16.71g、86.05mmol)、C6F6(ヘキサフルオロベンゼン)(100mL)、DMI(N,N’−ジメチルイミダゾリジノン)(70mL)を添加し、90℃で3時間還流した。反応が終了すれば、反応物の温度を室温に冷却し、EAで抽出し、水で拭く。有機層をMgSO4で乾燥し、濃縮した後、生成された有機物をシリカゲルカラムを利用して分離して、生成物6.66g(55%)を得た。
Sub1−18−e(6.10g、21.67mmol)、Sub2−57(8.48g、21.67mmol)、Pd2(dba)3(0.60g、0.65mmol)、NaOt−Bu(4.16g、43.33mmol)、P(t−bu)3(0.44g、2.17mmol)、トルエン(80mL)を前記Sub1−7の合成法を用いて、生成物11.42g(89%)を得た。
(4−ブロモ−2−ヨードフェニル)(エチル)スルファン(15.70g、45.77mmol)、(2−クロロフェニル)ボロン酸(7.16g、45.77mmol)、Pd(PPh3)4(1.59g、1.37mmol)、NaOH(3.66g、91.54mmol)、THF(200mL)、H2O(100mL)を前記Sub1−7−aの合成法を用いて、生成物12.60g(84%)を得た。
Sub1−23−a(11.60g、35.40mmol)、酢酸(150mL)、35%過酸化水素(H2O)(3.61g)を前記Sub1−7−bの合成法を用いて、生成物11.68g(96%)を得た。
Sub1−23−b(8.70g、25.31mmol)、硫酸(H2SO4)(50mL)を前記Sub1−7−cの合成法を用いて、生成物6.78g(90%)を得た。
Sub1−23−c(6.00g、20.16mmol)、Sub2−46(7.09g、20.16mmol)、Pd2(dba)3(0.55g、0.60mmol)、NaOt−Bu(3.88g、40.32mmol)、P(t−bu)3(0.41g、2.02mmol)、トルエン(80mL)を前記Sub1−7の合成法を用いて、生成物9.97g(87%)を得た。
(5−ブロモ−2−ヨードフェニル)(エチル)スルファン(22.00g、64.14mmol)、(2−クロロフェニル)ボロン酸(10.03g、64.14mmol)、Pd(PPh3)4(2.22g、1.92mmol)、NaOH(5.13g、128.27mmol)、THF(300mL)、H2O(150mL)を前記Sub1−7−aの合成法を用いて、生成物17.44g(83%)を得た。
Sub1−52−a(15.30g、46.69mmol)、酢酸(150mL)、35%過酸化水素(H2O)(4.76g)を前記Sub1−7−bの合成法を用いて、生成物15.57g(97%)を得た。
Sub1−52−b(10.8g、31.43mmol)、硫酸(H2SO4)(50mL)を前記Sub1−7−cの合成法を用いて、生成物8.88g(95%)を得た。
Sub1−52−c(7.20g、24.19mmol)、Sub2−60(5.31g、24.19mmol)、Pd2(dba)3(0.66g、0.73mmol)、NaOt−Bu(4.65g、48.39mmol)、P(t−bu)3(0.49g、2.42mmol)、トルエン(90mL)を前記Sub1−7の合成法を用いて、生成物9.28g(88%)を得た。
5−ブロモ−2−ヨードフェノール(13.0g、43.49mmol)に(4’−クロロ−[1,1'−ビフェニル]−2−イル)ボロン酸(10.11g、43.49mmol)、Pd(PPh3)4(1.51g、1.30mmol)、NaOH(3.48g、86.98mmol)、THF(150mL)、H2O(80mL)を前記Sub1−7−aの合成法を用いて、生成物10.79g(69%)を得た。
Sub1−58−d(8.60g、23.91mmol)にPd(OAc)2(0.27g、1.20mmol)、3−ニトロピリジン(0.15g、1.20mmol)、BzOOtBu(tert−ブチルパーオキシベンゾエート)(9.29g、47.82mmol)、C6F6(ヘキサフルオロベンゼン)(100mL)、DMI(N,N’−ジメチルイミダゾリジノン)(70mL)を前記Sub1−18−eの合成法を用いて、生成物4.19g(72%)を得た。
Sub1−58−e(3.90g、10.91mmol)、Sub2−13(2.94g、10.91mmol)、Pd2(dba)3(0.30g、0.33mmol)、NaOt−Bu(2.10g、21.81mmol)、P(t−bu)3(0.22g、1.09mmol)、トルエン(50mL)を前記Sub1−7の合成法を用いて、生成物4.18g(86%)を得た。
(2−ブロモ−6−ヨードフェニル)(エチル)スルファン(19.00g、55.39mmol)、(3−クロロナフタレン−2−イル)ボロン酸(11.43g、55.39mmol)、Pd(PPh3)4(1.92g、1.66mmol)、NaOH(4.43g、110.78mmol)、THF(200mL)、H2O(100mL)を前記Sub1−7−aの合成法を用いて、生成物17.37g(83%)を得た。
Sub1−73−a(16.50g、43.68mmol)、酢酸(150mL)、35%過酸化水素(H2O)(4.46g)を前記Sub1−7−bの合成法を用いて、生成物16.17g(94%)を得た。
Sub1−73−b(14.60g、37.08mmol)、硫酸(H2SO4)(100mL)を前記Sub1−7−cの合成法を用いて、生成物11.09g(86%)を得た。
Sub1−73−c(3.60g、10.36mmol)、Sub2−13(1.84g、10.87mmol)、Pd2(dba)3(0.28g、0.31mmol)、NaOt−Bu(1.99g、20.71mmol)、P(t−bu)3(0.21g、1.04mmol)、トルエン(40mL)を前記Sub1−7の合成法を用いて、生成物3.61g(80%)を得た。
前記反応スキーム1のSub2は、下記反応スキーム3の反応経路によって合成(本出願人の韓国登録特許第10−1251451号(2013.4.5日付登録公告)に開示)されてもよいが、これに限定されるものではない。
本発明の化合物を発光補助層物質として用いて、通常の方法に従って有機電子発光素子を作製した。まず、ガラス基板に形成されたITO層(正極)上に、4,4’,4’’−トリス[2−ナフチル(フェニル)アミノ]トリフェニルアミン(以下、‘2−TNATA’という)を60nm厚さで真空蒸着して正孔注入層を形成した後、前記正孔注入層上にNPBを60nm厚さで真空蒸着して正孔輸送層を形成した。前記正孔輸送層上に、本発明の化合物P−1を20nmの厚さで真空蒸着して、発光補助層を形成した後、前記発光補助層上に、4,4’−N,N’−ジカルバゾール−ビフェニル(以下、‘CBP’という)をホスト物質として、ビス−(1−フェニルイソキノリル)イリジウム(III)アセチルアセトン(以下、‘(piq)2Ir(acac)’という)をドーパント物質として用いて、95:5重量比でドープして、30nm厚さで真空蒸着して発光層を形成した。次いで、前記発光層上に、BAlqを5nm厚さで真空蒸着して正孔阻止層を形成し、前記正孔阻止層上にビス(10−ヒドロキシベンゾ[h]キノリナト)ベリリウム(以下、‘BeBq2’という)を40nm厚さで真空蒸着して電子輸送層を形成した。以後、ハロゲン化アルカリ金属であるLiFを0.2nm厚さで蒸着して、電子注入層を形成し、Alを150nmの厚さで蒸着して、負極を形成することによって、有機電子発光素子を製造した。
発光補助層物質として本発明の化合物P−1の代わりに、表4に記載の本発明の化合物P−2〜P−90を用いた点を除いては、実施例1と同様の方法で有機電子発光素子を作製した。
発光補助層を形成しない点を除いては、前記実施例1と同様の方法で有機電子発光素子を作製した。
発光補助層物質として本発明の化合物P−1の代わりに、表4に記載の下記の比較化合物1〜比較化合物5を、それぞれ用いた点を除いては、前記実施例1と同様の方法で有機電子発光素子を作製した。
110:基板
120:第1電極(正極)
130:正孔注入層
140:正孔輸送層
141:バッファ層
150:発光層
151:発光補助層
160:電子輸送層
170:電子注入層
180:第2電極(負極)
Claims (11)
- 下記式(1)で示される化合物:
R1、R2及びR3は、互いに独立して、水素;重水素;C6〜C60のアリール基;フルオレニル基;O、N、S、Si及びPの少なくとも一つのヘテロ原子を含むC2〜C60のヘテロ環基;C3〜C60の脂肪族環とC6〜C60の芳香族環との縮合環基;C1〜C50のアルキル基;C2〜C20のアルケニル基;C2〜C20のアルキニル基;C2〜C20のアルコキシル基;C6〜C30のアリールオキシ基及び−Lb−NAr3Ar4;からなる群から選ばれ、但し、R1、R2、R3中の一つは、−Lb−NAr3Ar4であり、
R4、R5、R6及びR7は、互いに独立して、水素;重水素;C6〜C60のアリール基;フルオレニル基;O、N、S、Si及びPの少なくとも一つのヘテロ原子を含むC2〜C60のヘテロ環基;C3〜C60の脂肪族環とC6〜C60の芳香族環との縮合環基;C1〜C50のアルキル基;C2〜C20のアルケニル基;C2〜C20のアルキニル基;C2〜C20のアルコキシル基及びC6〜C30のアリールオキシ基;からなる群から選ばれ、
隣接するR1とR2、隣接するR2とR3、隣接するR3とR4、隣接するR5とR6、隣接するR6とR7は、互いに独立して、互いに結合して芳香環又はヘテロ芳香環を形成していてもよく、
Ar1、Ar2、Ar3及びAr4は、互いに独立して、C6〜C60のアリール基;フルオレニル基;O、N、S、Si及びPの少なくとも一つのヘテロ原子を含むC2〜C60のヘテロ環基;C3〜C60の脂肪族環とC6〜C60の芳香族環との縮合環基;C1〜C50のアルキル基;C2〜C20のアルケニル基;C2〜C20のアルキニル基;C2〜C20のアルコキシル基;及びC6〜C30のアリールオキシ基;からなる群から選ばれ、但し、Ar1、Ar2、Ar3及びAr4の少なくとも一つは、下記一般式(1−1)
R8及びR9は、互いに独立して、水素;重水素;C6〜C60のアリール基;フルオレニル基;O、N、S、Si及びPの少なくとも一つのヘテロ原子を含むC2〜C60のヘテロ環基;C3〜C60の脂肪族環とC6〜C60の芳香族環との縮合環基;C1〜C50のアルキル基;C2〜C20のアルケニル基;C2〜C20のアルキニル基;C2〜C20のアルコキシル基;及びC6〜C30のアリールオキシ基;からなる群から選ばれ、又は、前記n、mが2以上の場合、それぞれ複数であって同じであるか、異なり、複数のR8同士あるいは複数のR9同士が互いに結合して、芳香環又はヘテロ芳香環を形成していてもよく、
nは、0〜3の整数、mは、0〜4の整数である}
で示される置換基となり、
La及びLbは、互いに独立して、単結合;C6−C60のアリーレン基;フルオレニレン基;C3〜C60の脂肪族環とC6〜C60の芳香族環との縮合環基;及びC2−C60のヘテロ環基;からなる群から選ばれ、
ここで、前記アリール基、フルオレニル基、アリーレン基、ヘテロ環基、縮合環基、アルキル基、アルケニル基、アルコキシ基及びアリールオキシ基は、それぞれ、重水素;ハロゲン;C1〜C20のアルキル基又はC6〜C20のアリール基で置換又は非置換されたシラン基;シロキサン基;C1〜C20のアルキルチオ基;C1〜C20のアルコキシル基;C1〜C20のアルキル基;C2〜C20のアルケニル基;C2〜C20のアルキニル基;C6〜C20のアリール基;重水素で置換されたC6〜C20のアリール基;フルオレニル基;C2〜C20のヘテロ環基;C3〜C20のシクロアルキル基;C7〜C20のアリールアルキル基及びC8〜C20のアリールアルケニル基からなる群から選ばれた一つ以上の置換基でさらに置換されていてもよく、また、これらの置換基は、互いに結合して、環を形成していてもよく、ここで「環」とは、C3〜C60の脂肪族環又はC6〜C60の芳香族環又はC2〜C60のヘテロ環又はこれらの組み合わせからなる縮合環を意味し、飽和又は不飽和環を含む。] - 前記一般式(1)のAr1及びAr2の少なくとも一つは、前記一般式(1−1)であり、前記Ar3及びAr4の少なくとも一つは、前記一般式(1−1)であることを特徴とする請求項1に記載の化合物。
- 前記一般式(1)のLa及びLbの少なくとも一つは、単結合であることを特徴とする請求項1に記載の化合物。
- 第1電極;第2電極;及び前記第1電極と第2電極と間に位置する有機物層;を含む有機電子素子において、
前記有機物層は、請求項1〜5のいずれか1項に記載の化合物を含むことを特徴とする有機電子素子。 - 前記有機物層は、正孔注入層、正孔輸送層、発光補助層及び発光層からなる群から選ばれ、前記有機物層に、1種又は2種以上の前記化合物を含むことを特徴とする請求項6に記載の有機電子素子。
- 前記有機物層が、正孔輸送層又は発光補助層であることを特徴とする請求項7に記載の有機電子素子。
- 前記第1電極の一側面中の前記有機物層と反対される一側、又は前記第2電極の一側面中の前記有機物層と反対される一側の少なくとも一つに形成される光効率改善層をさらに含む請求項6に記載の有機電子素子。
- 請求項6に記載の有機電子素子を含むディスプレイ装置;及び前記ディスプレイ装置を駆動する制御部;を含む電子装置。
- 前記有機電子素子は、有機電子発光素子、有機太陽電池、有機感光体、有機トランジスター、及び単色又は白色照明用素子の少なくとも一つであることを特徴とする請求項10に記載の電子装置。
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US20190296248A1 (en) | 2019-09-26 |
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EP3466926A4 (en) | 2020-01-22 |
CN109195950A (zh) | 2019-01-11 |
CN109195950B (zh) | 2022-03-11 |
KR102018682B1 (ko) | 2019-09-04 |
US20190296244A1 (en) | 2019-09-26 |
WO2017204557A1 (ko) | 2017-11-30 |
US11882763B2 (en) | 2024-01-23 |
JP6777810B2 (ja) | 2020-10-28 |
KR20170134215A (ko) | 2017-12-06 |
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