JP2021109841A - 可溶性置換基を有するビスアントラセン誘導体およびそれらを用いた有機電界発光素子 - Google Patents
可溶性置換基を有するビスアントラセン誘導体およびそれらを用いた有機電界発光素子 Download PDFInfo
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- JP2021109841A JP2021109841A JP2020002062A JP2020002062A JP2021109841A JP 2021109841 A JP2021109841 A JP 2021109841A JP 2020002062 A JP2020002062 A JP 2020002062A JP 2020002062 A JP2020002062 A JP 2020002062A JP 2021109841 A JP2021109841 A JP 2021109841A
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- 230000003381 solubilizing effect Effects 0.000 title 1
- 239000000463 material Substances 0.000 claims abstract description 88
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000001302 tertiary amino group Chemical group 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- -1 anthracene derivative compound Chemical class 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000005577 anthracene group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
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- GWNJZSGBZMLRBW-UHFFFAOYSA-N 9,10-dinaphthalen-1-ylanthracene Chemical compound C12=CC=CC=C2C(C=2C3=CC=CC=C3C=CC=2)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 GWNJZSGBZMLRBW-UHFFFAOYSA-N 0.000 description 3
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 3
- ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 9-bromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=CC2=C1 ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 0 C=*1C=*C=C1 Chemical compound C=*1C=*C=C1 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 3
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- 125000006165 cyclic alkyl group Chemical group 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 2
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- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
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- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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Abstract
Description
Xは、第三級アミン構造を含むアリール基であり、Yは1つのオルト位にアルキル又はアリール置換基を有するフェニル基である。
Yは、o−ビフェニル基(あるいは2−ビフェニル基)であることが特に好ましい。
本発明の有機ELデバイスにおいて、上記一般式(1)で表される化合物を含有する有機層が発光層であることが好ましい。
したがって、本発明の化合物は、有機ELデバイスのためのエミッターとして有用である。
本発明の有機電界発光素子、すなわち有機ELデバイスは、上記一般式(1)で表される化合物を含有する有機層を含む。有機層は発光層であり、一般式(1)で表される化合物を発光層中の発光材料として用いることが好ましい。
それらの中でも特に好ましい化合物として、9,10-ジフェニルアントラセン、9,10-ジ(1-ナフチル)アントラセン、9,10-ジ(2-ナフチル)アントラセン、9,10-ジフェニルアントラセン、9-(ナフタレン-1-イル)-10-(ナフタレン-2-イル)アントラセン(α,β-ADN)、2-メチル-9,10-ジ(2-ナフチル)アントラセン、2-メチル-9,10-ジ(1-ナフチル)アントラセン、2-メチル-9-(ナフタレン-1-イル)-10-(ナフタレン-2-イル)アントラセンを挙げることが出来る。
以下の比較例において用いた化合物PAPAP−0は以下の化学式で表される化合物である。
上記合成実施例で得た PAPAP−1及びPAPAP−0に対して、シクロヘキサノンを溶媒として用いて溶解性試験をした。 PAPAP−1及びPAPAP−0をそれぞれ10mg計りとり、シクロヘキサノンを1mL加え、温度約100℃にて熱攪拌を行なった。
試験サンプルの光学特性評価に用いた機器及び測定条件は以下の通りである。
(1) 紫外・可視 (UV-vis) 分光光度計
(株)島津製作所 UV-2600
測定条件 ; スキャンスピード 中速、測定範囲 200~800 nm サンプリングピッチ
0.5 nm, スリット幅 0.5 nm
(2) 蛍光分光光度計
(株)堀場製作所 FluoroMax 2
光源 : キセノンランプ Integration Time : 5.0 sec
Exicit Mono Slits : 0.300 mm, Emiss Mono Slits : 0.300 mm
(3) 発光量子収率測定
(株)浜松ホトニクス 積分球、起光照射装置 L10092 + A10079
励起光 : 300 ~ 400 nm
PAPAP−1のトルエン溶液 (10-5M) を調製し、吸収 (UV-vis) ・発光 (PL) スペクトルを測定した。結果を図2に示す。UV-vis 吸収スペクトルの結果から、PAPAP−1の吸収端がPAPAP−0よりも長波長化していることが観測された(図2左)。またPLスペクトル(図2右)からも発光波長が長波長化していることが観測された。
PAPAP−1のトルエン溶液 (10−5M) を調製し、発光量子収率を測定した。測定結果を以下の表1に示す。
比較例1として、PAPAP−1に代えてPAPAP−0を用いて、実施例2、3に記載した工程と同じ工程を行うことによって、吸収 (UV-vis) ・発光 (PL) スペクトル、発光量子収率を測定した。
実施例2、3及び比較例1のそれぞれの評価結果を表1に示す。
最初に、予めパターン形成されたITO(indium tin oxide)が100nmの厚さで薄膜蒸着されたガラス基板を、洗剤を溶かした蒸留水に入れて超音波で洗浄した。この時、洗剤としてはフィッシャー社(Fisher Co.)の製品を使用し、蒸留水はミリポア社(Millipore Co.)製品のフィルタで2次ろ過した蒸留水を使用した。上記ITOを30分間洗浄した後、蒸留水で2回繰り返して超音波洗浄を10分間行った。蒸留水洗浄が終わった後、アセトン、蒸留水、イソプロピルアルコール溶剤で順次超音波洗浄をしてから乾燥後、UV-オゾン(O3)を用いた表面処理を行った。その後、有機層を形成させるために、正孔注入層、正孔輸送層(HTL)、及び発光層をスピンコートにより順次成膜した。スピンコートによる成膜後、前述の各層が堆積した基板を蒸着装置に入れ、約10-4〜約10-5 Paの真空度において、発光層の上にホールブロック層、電子輸送層、電子注入層、陰極を一層ずつ順次堆積させた。
上述した方法に準拠して作製した有機ELデバイスの発光特性を、浜松ホトニクス株式会社の PHOTONICMULTI-CHANNEL ANALYZER PMA-11 を使用して測定した。測定結果を下の表に示す
溶媒としてシクロヘキサノンを用いて、PAPAP−12及びPAPAP−1の溶解性試験をした。PAPAP−12及びPAPAP−1をそれぞれ10mg計りとり、それぞれにシクロヘキサノンを1ml加え、温度約100℃にて熱攪拌を行なった。
以下の光学特性評価に用いた機器及び測定条件は以下の通りである。
(1) 紫外・可視 (UV-vis) 分光光度計
(株) 島津製作所 UV-2600
測定条件 ; スキャンスピード 中速、測定範囲 200~800 nm サンプリングピッチ
0.5 nm, スリット幅 0.5 nm
(2) 蛍光分光光度計
(株)堀場製作所 FluoroMax 2
光源 : キセノンランプ Integration Time : 5.0 sec
Exicit Mono Slits : 0.300 mm, Emiss Mono Slits : 0.300 mm
(3) 発光量子収率測定
(株)浜松ホトニクス 積分球、起光照射装置 L10092 + A10079
励起光 : 300 ~ 400 nm
PAPAP−12のトルエン溶液 (10−5M) を調製し、吸収 (UV-vis) ・発光 (PL) スペクトルを測定した。結果を図3に示す。UV-vis吸収スペクトルの結果から、PAPAP−12の吸収端がPAPAP−1よりも短波長化していることが観測された。またPLスペクトルからも発光波長が短波長化していることが観測された。
PAPAP−12のトルエン溶液 (10−5M) を調製し、発光量子収率を測定した。測定結果を以下の表4に示す。
実施例6、7の評価結果を、表4に示す。
最初に、予めパターン形成をし、洗浄をしたITO-ガラス基板に対して、UV-オゾン(O3)を用いた表面処理を行った。ITO-ガラス基板のITO層(第一の電極)の厚さは約100nmだった。表面処理の後、有機層を形成させるために、正孔注入層、正孔輸送層(HTL)、発光層をスピンコートにより順次成膜した。スピンコートによる成膜後、前述の各層が堆積した基板を蒸着装置に入れ、約10−4〜約10−5Paの真空度において、発光層の上にホールブロック層、電子輸送層、電子注入層、陰極を1つずつ順次堆積させた。
上述した方法に準拠して作製した有機ELデバイスの発光特性を、浜松ホトニクス株式会社のPHOTONICMULTI-CHANNEL ANALYZER PMA-11 を使用して測定した。測定結果を下の表に示す
2 ・・・アノード
3 ・・・正孔注入層
4 ・・・正孔輸送層
5 ・・・有機発光層
6 ・・・電子輸送層
7 ・・・カソード
Claims (8)
- 一般式(1)において、Xが下記一般式(2)で示される、請求項1に記載の化合物。
- Yがo−ビフェニル基である、請求項1又は2に記載の化合物。
- 請求項1〜3のいずれか一項に記載の化合物からなる、有機電界発光素子用発光材料。
- 請求項1〜3のいずれか一項に記載の一般式(1)で示される化合物を含むことを特徴とする有機電界発光素子。
- 請求項1〜3のいずれか一項に記載の一般式(1)で示される化合物を含む発光層を有することを特徴とする有機電界発光素子。
- 一般式(1)で示される化合物を発光層中にエミッターとして含むことを特徴とする請求項6に記載の有機電界発光素子。
- さらに、アミノ基を有しない芳香族炭化水素であるアントラセン誘導体化合物を発光層中にホスト材料として含むことを特徴とする、請求項7に記載の有機電界発光素子。
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KR1020227018331A KR20220095213A (ko) | 2020-01-09 | 2021-01-08 | 가용성 치환기를 갖는 비스안트라센 유도체 및 그들을 이용한 유기 전계 발광 소자 |
PCT/KR2021/000229 WO2021141428A1 (ko) | 2020-01-09 | 2021-01-08 | 가용성 치환기를 갖는 비스안트라센 유도체 및 그들을 이용한 유기 전계 발광 소자 |
US17/790,846 US20230089555A1 (en) | 2020-01-09 | 2021-01-08 | Bisanthracene Derivatives Having Solubilizing Substituent, and Organic Electroluminescence Device Using Same |
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KR101373587B1 (ko) * | 2011-11-29 | 2014-03-14 | 한국교통대학교산학협력단 | 용액공정용 나프틸페닐 유도체 및 이를 채용한 유기 전계 발광 소자 |
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