JP5789251B2 - モノマー、ポリマー、およびその製造方法 - Google Patents
モノマー、ポリマー、およびその製造方法 Download PDFInfo
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- JP5789251B2 JP5789251B2 JP2012505233A JP2012505233A JP5789251B2 JP 5789251 B2 JP5789251 B2 JP 5789251B2 JP 2012505233 A JP2012505233 A JP 2012505233A JP 2012505233 A JP2012505233 A JP 2012505233A JP 5789251 B2 JP5789251 B2 JP 5789251B2
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- 125000001424 substituent group Chemical group 0.000 claims description 25
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- 125000000732 arylene group Chemical group 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- IPUHTFAUVSQQQI-UHFFFAOYSA-N 15,15-bis(2-ethylhexyl)tetracyclo[10.2.1.05,14.08,13]pentadeca-1,3,5(14),6,8(13),9,11-heptaene Chemical compound C1=CC=C2C(CC(CC)CCCC)(CC(CC)CCCC)C3=CC=CC4=CC=C1C2=C34 IPUHTFAUVSQQQI-UHFFFAOYSA-N 0.000 description 1
- UHUVVQKTFIBVPL-UHFFFAOYSA-N 15,15-bis(2-ethylhexyl)tetracyclo[10.2.1.05,14.08,13]pentadeca-1,3,5(14),8(13),9,11-hexaene Chemical compound C1CC2=CC=CC3=C2C2=C1C=CC=C2C3(CC(CC)CCCC)CC(CC)CCCC UHUVVQKTFIBVPL-UHFFFAOYSA-N 0.000 description 1
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- ZGDJMMPBPMJJBR-UHFFFAOYSA-N bis(1H-indol-2-yl)diazene Chemical compound c1c(N=Nc2cc3ccccc3[nH]2)[nH]c2ccccc12 ZGDJMMPBPMJJBR-UHFFFAOYSA-N 0.000 description 1
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- ICMGJLRWDJYLGU-UHFFFAOYSA-N carbamic acid;2-hydroxybenzoic acid Chemical compound NC(O)=O.OC(=O)C1=CC=CC=C1O ICMGJLRWDJYLGU-UHFFFAOYSA-N 0.000 description 1
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- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/32—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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Description
R1は任意の置換基であり、
R2は任意の置換基であり、
R1およびR2は、連結して飽和または不飽和環を形成してもよく、
Lは、反応性脱離基を表し、
XおよびYは、それぞれ独立に、CR2、O、BR、NR、SiR2、S、S=O、SO2、PRまたはP=O(R)を表し、ここで、各出現時におけるRは、Hまたは置換基から独立に選択され、
Zは、単結合または二価の原子もしくは基を表し、かつ
X−Z−Yは非共役環または鎖を形成し、但し、Zが単結合の場合、R1およびR2の少なくとも一方はアリールまたはヘテロアリール基である]
を有する。
本発明によるモノマーは、下記のスキームに従って合成することができる。
本発明のポリマーは、上記した繰り返し単位の少なくとも1つを含み、好ましくは、1つまたは複数のさらなる繰り返し単位を含む。これらのさらなる繰り返し単位は、その所望の使用、特に、正孔輸送、電子輸送および/またはエレクトロルミネッセンスポリマーのいずれかとしてのその使用に従って、本発明のポリマーの特性を調節するように選択することができる。
これらのポリマーの調製のための好ましい方法は、例えばWO00/53656において記載されているスズキ重合、および例えばT.Yamamoto、「Electrically Conducting And Thermally Stable π−Conjugated Poly(arylene)s Prepared by Organometallic Processes」、Progress in Polymer Science 1993、17、1153〜1205において記載されているヤマモト重合である。これらの重合技術はいずれも、アリール基とモノマーの脱離基との間に金属錯体触媒の金属原子が挿入される「金属挿入」を介して操作するものである。山本重合の場合はニッケル錯体触媒が使用され、スズキ重合の場合はパラジウム錯体触媒が使用される。
単一ポリマーまたは複数のポリマーを溶液から堆積させて、エレクトロルミネッセンス層を形成することができる。適切な溶媒は、トルエンおよびキシレン等のモノ−またはポリ−アルキルベンゼンを含む。特に好ましい溶液堆積技術は、スピンコーティングおよびインクジェットプリンティングである。
ML1 qL2 rL3 S
(V)
[式中、Mは金属であり;L1、L2およびL3のそれぞれは配位基であり;qは整数であり;rおよびsは、それぞれ独立に、0または整数であり;かつ、(a.q)+(b.r)+(c.s)の和は、M上で利用可能な配位部位の数と等しく、ここで、aはL1上の配位部位の数であり、bはL2上の配位部位の数であり、かつ、cはL3上の配位部位の数である]を含む。
− セリウム、サマリウム、ユーロピウム、テルビウム、ジスプロシウム、ツリウム、エルビウムおよびネオジムのランタノイド金属、ならびに
− d−ブロック金属、特に、2行目および3行目のもの、すなわち、元素39から48および72から80、特に、ルテニウム、ロジウム、パラジウム、レニウム、オスミウム、イリジウム、白金および金
を含む。
図1を参照すると、本発明によるエレクトロルミネッセンスデバイスの構成は、透明ガラスまたはプラスチック基板1と、アノード2と、カソード4とを含む。エレクトロルミネッセンス層3は、アノード2とカソード4との間に設けられている。本発明によるエレクトロルミネッセンスデバイスは、エレクトロルミネッセンス層3中または電荷輸送層(図示せず)中に、上記の本発明のポリマーを含む。
電荷輸送層、電荷注入層または電荷ブロック層等のさらなる層を、アノード2とカソード4との間に設置してもよい。
エレクトロルミネッセンス層3は、エレクトロルミネッセンス材料単独で構成されていてもよく、またはエレクトロルミネッセンス材料を1種もしくは複数のさらなる材料と組み合わせて含んでいてもよい。特に、エレクトロルミネッセンス材料は、例えばWO99/48160において開示されているように、正孔および/もしくは電子輸送材料と混和されていてもよく、または半導体ホストマトリクス中にルミネッセンスドーパントを含んでいてもよい。あるいは、エレクトロルミネッセンス材料は、電荷輸送材料および/またはホスト材料と共有結合していてもよい。
カソード4は、エレクトロルミネッセンス層への電子の注入を可能にする仕事関数を有する材料から選択される。カソードとエレクトロルミネッセンス材料との間の有害な相互作用の可能性等の他の要因は、カソードの選択に影響を与える。カソードは、アルミニウムの層等の単一材料から構成されていてもよい。あるいは、カソードは、複数の金属、例えば、WO98/10621において開示されているカルシウムおよびアルミニウム等、低仕事関数材料および高仕事関数材料の二重層;WO98/57381、Appl.Phys.Lett.2002、81(4)、634およびWO02/84759において開示されている元素バリウム;または、金属化合物、特に、電子注入を補助するためのアルカリもしくはアルカリ土類金属の酸化物もしくはフッ化物、例えばWO00/48258において開示されているフッ化リチウムの薄層;Appl.Phys.Lett.2001、79(5)、2001において開示されているフッ化バリウム;ならびに酸化バリウムを含んでいてもよい。デバイスに電子を効率的に注入するために、カソードは、好ましくは3.5eV未満、より好ましくは3.2eV未満、最も好ましくは3eV未満の仕事関数を有する。金属の仕事関数は、例えば、Michaelson、J.Appl.Phys.48(11)、4729、1977において見ることができる。
光学デバイスは、水分および酸素に対して感受性が高い傾向がある。したがって、基板は、好ましくは、デバイスへの水分および酸素の侵入を防止するために良好な障壁特性を有する。基板は一般にガラスであるが、特にデバイスの柔軟性が望ましい場合、別の基板を使用してもよい。例えば、基板は、代替のプラスチックおよび障壁層の基板または薄ガラスのラミネートを開示するUS6268695にあるようなプラスチック、ならびにEP0949850において開示されているプラスチックを含んでいてもよい。
Claims (14)
- 一般式:
[式中、
R1は任意の置換基であり、R2は任意の置換基であり、R1およびR2は、連結して飽和または不飽和環を形成してもよく、
Lは、反応性脱離基を表し、各Lは、ボロン酸もしくはそのエステル、塩素、臭素、ヨウ素、トシレート、メシレートおよびトリフレートからなる群から独立に選択され、
XおよびYは、いずれも−CH2−であり、
Zは、単結合または(CH2)p−であり、pは、1、2、3、4、5または6である]
を有する、置換されていてもよい化合物であって、
ここで、X−Z−Yは鎖を形成し、但し、Zが単結合の場合、R1およびR2の少なくとも一方はアリールまたはヘテロアリール基である、
ことを特徴とする化合物。 - R1およびR2は、各出現時において独立に、置換されていてもよい直鎖、分枝鎖もしくは環式アルキル[ここで、1つまたは複数の隣接しないC原子は、O、S、NR、C=Oおよび−COO−で置き換えられていてもよく、ここで、各出現時におけるRはHまたはアルキルである];または置換されていてもよいアリールもしくはヘテロアリールからなる群のいずれか1つである、請求項1に記載の化合物。
- R1およびR2の少なくとも一方は、1個もしくは複数のハロゲンによって置換されていてもよいアルキル基、または1個もしくは複数の任意の置換基を有するアリールもしくはヘテロアリール基であり、各任意の置換基は、任意に1個または複数のハロゲンによって置換されていてもよく、かつ1個または複数の隣接しないC原子がO、S、NR、C=Oおよび−COO−で置き換えられていてもよいアルキル基である、請求項2に記載の化合物。
- 半導体ポリマーである、請求項5に記載のポリマー。
- アリーレン共繰り返し単位を含む、請求項5または6に記載のポリマー。
- 発光ポリマーである、請求項5から7のいずれか一項に記載のポリマー。
- 請求項1から4のいずれか一項に記載の化合物を重合させることを含む、請求項5に記載のポリマーを製造する方法。
- 前記重合が金属触媒の存在下で生ずる、請求項9に記載の方法。
- 前記金属触媒がパラジウム触媒である、請求項10に記載の方法。
- 請求項5から8のいずれかに記載のポリマーを含む、電子デバイス。
- 発光ダイオード、電界効果トランジスタまたは光起電デバイスである、請求項12に記載の電子デバイス。
- 発光ダイオードである、請求項13に記載の電子デバイス。
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KR100704655B1 (ko) * | 2004-06-19 | 2007-04-10 | 부산대학교 산학협력단 | 발광 고분자 또는 그 유도체 및 이를 이용한 전기 발광 소자 |
KR101359630B1 (ko) * | 2006-10-23 | 2014-02-10 | 삼성디스플레이 주식회사 | 유기 전계 발광 화합물 및 이를 이용한 유기 전계 발광소자 |
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2009
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2010
- 2010-04-15 CN CN2010800165752A patent/CN102395549A/zh active Pending
- 2010-04-15 JP JP2012505233A patent/JP5789251B2/ja not_active Expired - Fee Related
- 2010-04-15 US US13/258,550 patent/US8598306B2/en active Active
- 2010-04-15 DE DE112010001646T patent/DE112010001646T5/de not_active Withdrawn
- 2010-04-15 KR KR1020117027195A patent/KR101573969B1/ko active IP Right Grant
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Publication number | Publication date |
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JP2012524054A (ja) | 2012-10-11 |
GB0906544D0 (en) | 2009-05-20 |
WO2010119274A1 (en) | 2010-10-21 |
US20120095184A1 (en) | 2012-04-19 |
KR20120013386A (ko) | 2012-02-14 |
DE112010001646T5 (de) | 2012-08-02 |
US8598306B2 (en) | 2013-12-03 |
KR101573969B1 (ko) | 2015-12-02 |
GB2469497A (en) | 2010-10-20 |
GB2469497B (en) | 2012-04-11 |
CN102395549A (zh) | 2012-03-28 |
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