JP7023957B2 - 非対称性の繰り返し単位を有するポリマー - Google Patents
非対称性の繰り返し単位を有するポリマー Download PDFInfo
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- JP7023957B2 JP7023957B2 JP2019528912A JP2019528912A JP7023957B2 JP 7023957 B2 JP7023957 B2 JP 7023957B2 JP 2019528912 A JP2019528912 A JP 2019528912A JP 2019528912 A JP2019528912 A JP 2019528912A JP 7023957 B2 JP7023957 B2 JP 7023957B2
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- 125000003118 aryl group Chemical group 0.000 claims description 94
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- 238000006116 polymerization reaction Methods 0.000 claims description 21
- 229910052786 argon Inorganic materials 0.000 claims description 20
- 125000004122 cyclic group Chemical group 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 19
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- 238000005401 electroluminescence Methods 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
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- 239000000412 dendrimer Substances 0.000 claims description 10
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
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- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
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- 239000003999 initiator Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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- 235000011152 sodium sulphate Nutrition 0.000 description 7
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- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
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- 229920001577 copolymer Polymers 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
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- 238000000926 separation method Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- 0 CCCCCCCC*C1(CCCCCCCC)c(cc(B2OC(C)(C)C(C)(C)O2)cc2)c2-c2ccccc12 Chemical compound CCCCCCCC*C1(CCCCCCCC)c(cc(B2OC(C)(C)C(C)(C)O2)cc2)c2-c2ccccc12 0.000 description 3
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
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Description
Aは、10~60、好ましくは12~50、より好ましくは12~30の芳香族またはヘテロ芳香族環原子を有し、1以上のRラジカルによって置換されていてもよい、多環式の、芳香族またはヘテロ芳香族環系であり、
Bは、5~10の芳香族またはヘテロ芳香族環原子を有し、1以上のRラジカルによって置換されていてもよい、単環式もしくは多環式の、芳香族またはヘテロ芳香族環系であり、
ここで、A中の芳香族またはヘテロ芳香族環原子の数が、B中の芳香族またはヘテロ芳香族環原子の数を超えるものであり、
Ar1、Ar2、Ar3およびAr4は、出現毎に同一であるかまたは異なり、5~60の芳香族環原子を有し、1以上のRラジカルによって置換されていてもよい、単環式もしくは多環式の、芳香族またはヘテロ芳香族環系であり、
n、m、oおよびpは、同一であるかまたは異なり、それぞれ0または1であり、
Rは、出現毎に同一であるかまたは異なり、H、D、F、Cl、Br、I、N(R1)2、CN、NO2、Si(R1)3、B(OR1)2、C(=O)R1、P(=O)(R1)2、S(=O)R1、S(=O)2R1、OSO2R1、1~40の炭素原子を有する、直鎖の、アルキル、アルコキシもしくはチオアルコキシ基または3~40の炭素原子を有する、分岐もしくは環状の、アルキル、アルコキシもしくはチオアルコキシ基(これらのそれぞれは、1以上のR1ラジカルによって置換されていてもよく、ここで1以上の隣接しないCH2基はR1C=CR1、C≡C、Si(R1)2、C=O、C=S、C=NR1、P(=O)(R1)、SO、SO2、NR1、O、SまたはCONR1によって置き換えられていてもよく、ここで1以上の水素原子はD、F、Cl、Br、IまたはCNによって置き換えられていてもよい)、または5~60の芳香族環原子を有し、それぞれのケースにおいて1以上のR1ラジカルによって置換されていてもよい、単環式もしくは多環式の、芳香族またはヘテロ芳香族環系、5~60の芳香族環原子を有し、1以上のR1ラジカルによって置換されていてもよい、アリールオキシもしくはヘテロアリールオキシ基、または5~60の芳香族環原子を有し、1以上のR1ラジカルによって置換されていてもよい、アラルキルまたはヘテロアラルキル基、または10~40の芳香族環原子を有し、1以上のR1ラジカルによって置換されていてもよい、ジアリールアミノ基、ジヘテロアリールアミノ基またはアリールヘテロアリールアミノ基、または架橋性Q基であり;ここで、2以上のRラジカルがともに、単環式もしくは多環式の、脂肪族、芳香族および/またはベンゾ縮合環系を形成していてもよく;
R1は、出現毎に同一であるかまたは異なり、H、D、Fまたは1~20の炭素原子を有する、脂肪族ヒドロカルビルラジカル、5~20の炭素原子を有する、芳香族および/またはヘテロ芳香族ヒドロカルビルラジカル(ここで、1以上の水素原子がFによって置き換えられていてもよい)であり;ここで、2以上のR1置換基がともに、単環式もしくは多環式の、脂肪族、芳香族またはヘテロ芳香族環系を形成していてもよく;かつ
点線は、ポリマー中の隣接する構造単位への結合を示す。
Xは、CR2、NR、SiR2、O、S、C=OまたはP=O、好ましくはCR2、NR、OまたはSであり、
oは、0、1、2または3であり、
pは、0、1または2であり、
qは、0、1、2、3または4である。
rは、0、1、2、3、4または5である。
グループ1:ポリマーの正孔注入および/または正孔輸送特性に影響を与える単位、
グループ2:ポリマーの電子注入および/または電子輸送特性に影響を与える単位、
グループ3:グループ1およびグループ2のそれぞれの単位の組み合わせを有する単位、
グループ4:電子蛍光よりも電子燐光が得られるような発光特性を変える単位、
グループ5:一重項から三重項状態への遷移を改良する単位、
グループ6:得られるポリマーの発光カラーに影響を与える単位、
グループ7:ポリマー骨格として典型的に使用される単位、
グループ8:ポリマー中のπ電子の局在を阻害し、ポリマー中の共役長さを短くする単位。
a)末端もしくは環状のアルケニル、または末端ジエニルおよびアルキニル基:
適切な単位は、末端もしくは環状の二重結合、末端ジエニル、または末端三重結合、特に、2~40の炭素原子を有する、好ましくは2~10の炭素原子を有する、末端もしくは環状のアルケニル、末端ジエニルおよびアルキニル基、を含むものであり、ここでそれぞれのCH2基および/またはそれぞれの水素原子は、上述のR基によって置き換えられていてもよい。さらに、適切なものは、前駆体として見なされる基、および二重または三重結合の本来の構造をもつことができる基である。
b)アルケニルオキシ、ジエニルオキシまたはアルキニルオキシ基:
さらに、適切なのは、アルケニルオキシ、ジエニルオキシまたはアルキニルオキシ基、好ましくはアルケニルオキシ基である。
c)アクリル酸基:
さらに、適切なのは、最も広い意味でのアクリル酸単位、好ましくはアクリル酸エステル、アクリル酸アミド、メタクリル酸エステル、およびメタクリル酸アミドである。特に好ましくは、C1-10のアクリル酸アルキルおよびC1-10のメタクリル酸アルキルである。
さらに適切な架橋性基Qの分類は、開環を介してカチオンによる架橋をする、オキセタンおよびオキシランである。
架橋性基の分類として、さらに適切なのは、シラン基SiR3であり、ここで少なくとも2つのR基、好ましくは全てのR基が、Clまたは1~20の炭素原子を有するアルコキシ基である。
この基は、水の存在下で反応し、オリゴ-またはポリシロキサンとなる。
上記のa)~f)の架橋性基Qは、当業者に一般に知られており、それらの基の反応に使用される適切な反応条件で使用される。
式Q14中のAr10は、式(I)中のAr1に記載の意味を有する。
oは、0、1、2または3であり、
pは、0、1または2であり、
qは、0、1、2、3または4である。
oは、0、1、2または3であり、
pは、0、1または2であり、
qは、0、1、2、3または4であり、
xは、1、2、3または4であり、ここでx+o≦4である。
oは、0、1、2または3であり、
pは、0、1または2であり、
qは、0、1、2、3または4であり、
rは、0、1、2、3、4または5であり、
xは、1、2、3または4であり、ここで、x+o≦4であり、
yは、1、2、3、4または5であり、ここで、y+q≦5である。
(B)ヤマモト重合、
(C)スティル(STILLE)重合、
(D)ヘック(HECK)重合、
(E)ネギシ重合、
(F)シノガシラ重合、
(G)ヒヤマ重合、および
(H)ハートウィグ-ブッフバルト(HARTWIG-BUCHWALD)重合。
(a)1以上の架橋性Q基を有する構造単位を含むポリマーを提供すること、および
(b)遊離ラジカルまたはイオン性の架橋(好ましくは遊離ラジカル架橋)、であり、これは熱的または放射(好ましくは熱的)に引き起こされうる。
パートA:モノマーの合成
全ての合成は、特に断りのない限り、乾燥溶媒中で、アルゴン雰囲気下で行われる。
モノマーMon-1の合成
モノマーMon-2~Mon-5およびMon-16の合成
モノマーMon-6の合成
モノマーMon-7およびMon-8の合成
モノマーMon-9の合成
モノマーMon-10~Mon-12の合成
モノマーMon-13の合成
モノマーMon-14およびMon-15の合成
モノマーMon-1-BEの合成
モノマーMon-6-BE、Mon-9-BEおよびMon-13-BEの合成
例21~41
比較ポリマーV1、V2、V3およびV4および本発明のポリマーPo1~Po17の調製
例21~41
架橋後のポリマーの架橋性のバリアントが完全に不溶な層を生じさせるか否かは、WO2010/097155と同様に試験される。
表8は、WO2010/097155に開示される洗浄操作後の、当初100nmの残留層の厚さを示す。層厚が減少していない場合に、ポリマーは、不溶であり、それゆえ架橋が十分である。
構造Aは以下である:
-基板
-ITO(50nm)
-PEDOT:PSS(20nm)
-正孔輸送層(HTL)(20nm)
-発光層(EML)(60nm)
-正孔ブロック層(HBL)(10nm)
-電子輸送層(ETL)(40nm)
-カソード。
-基板
-ITO(50nm)
-PEDOT:PSS(20nm)
-正孔輸送層(HTL)(40nm)
-発光層(EML)(30nm)
-電子輸送層(ETL)(20nm)
-カソード。
構造Bにおいて、発光層は、空チャンバー内で熱蒸着されることにより形成される。この層は、1超の材料からなっていてよく、材料は、特定の体積比において共蒸着により互いに添加される。H3:ドーパント(95%:5%)の形で与えられる場合、ここでは、H3とトーパント材料とが層中に95%:5%の体積比率で存在することを意味する。
Claims (14)
- 以下の式(Ia)の構造単位を少なくとも1つ有するポリマー。
Aは、10~60、好ましくは12~50、より好ましくは12~30の芳香族またはヘテロ芳香族環原子を有し、1以上のRラジカルによって置換されていてもよい、多環式の縮合された、芳香族またはヘテロ芳香族環系であり、
Bは、5~10の芳香族またはヘテロ芳香族環原子を有し、1以上のRラジカルによって置換されていてもよい、単環式もしくは多環式の、芳香族またはヘテロ芳香族環系であり、
ここで、A中の芳香族またはヘテロ芳香族環原子の数が、B中の芳香族またはヘテロ芳香族環原子の数を超えるものであり、
Ar1、Ar2、Ar3およびAr4は、出現毎に同一であるかまたは異なり、5~60の芳香族環原子を有し、1以上のRラジカルによって置換されていてもよい、単環式もしくは多環式の、芳香族またはヘテロ芳香族環系であり、
oおよびpは、同一であるかまたは異なり、それぞれ0または1であり、
Rは、出現毎に同一であるかまたは異なり、H、D、F、Cl、Br、I、N(R1)2、CN、NO2、Si(R1)3、B(OR1)2、C(=O)R1、P(=O)(R1)2、S(=O)R1、S(=O)2R1、OSO2R1、1~40の炭素原子を有する、直鎖の、アルキル、アルコキシもしくはチオアルコキシ基または3~40の炭素原子を有する、分岐もしくは環状の、アルキル、アルコキシもしくはチオアルコキシ基(これらのそれぞれは、1以上のR1ラジカルによって置換されていてもよく、ここで1以上の隣接しないCH2基はR1C=CR1、C≡C、Si(R1)2、C=O、C=S、C=NR1、P(=O)(R1)、SO、SO2、NR1、O、SまたはCONR1によって置き換えられていてもよく、ここで1以上の水素原子はD、F、Cl、Br、IまたはCNによって置き換えられていてもよい)、または5~60の芳香族環原子を有し、それぞれのケースにおいて1以上のR1ラジカルによって置換されていてもよい、単環式もしくは多環式の、芳香族またはヘテロ芳香族環系、5~60の芳香族環原子を有し、1以上のR1ラジカルによって置換されていてもよい、アリールオキシもしくはヘテロアリールオキシ基、または5~60の芳香族環原子を有し、1以上のR1ラジカルによって置換されていてもよい、アラルキルまたはヘテロアラルキル基、または10~40の芳香族環原子を有し、1以上のR1ラジカルによって置換されていてもよい、ジアリールアミノ基、ジヘテロアリールアミノ基またはアリールヘテロアリールアミノ基、または架橋性Q基であり;ここで、2以上のRラジカルがともに、単環式もしくは多環式の、脂肪族、芳香族および/またはベンゾ縮合環系を形成していてもよく;
R1は、出現毎に同一であるかまたは異なり、H、D、Fまたは1~20の炭素原子を有する、脂肪族ヒドロカルビルラジカル、5~20の炭素原子を有する、芳香族および/またはヘテロ芳香族ヒドロカルビルラジカル(ここで、1以上の水素原子がFによって置き換えられていてもよい)であり;ここで、2以上のR1置換基がともに、単環式もしくは多環式の、脂肪族、芳香族またはヘテロ芳香族環系を形成していてもよく;かつ
点線は、ポリマー中の隣接する構造単位への結合を示す) - ポリマー中の式(Ia)の構造単位の比率が、ポリマー中に構造単位として存在する全ての共重合性モノマー100mol%を基準として、50~95mol%の範囲であることを特徴とする、請求項1~5のいずれか一項に記載のポリマー。
- ポリマーが、式(Ia)の構造単位だけでなく、式(Ia)の構造単位とは異なるさらなる構造単位を有することを特徴とする、請求項1~6のいずれか一項に記載のポリマー。
- ポリマーが、1以上の式(Ia)の構造単位および所望によりさらなる構造単位だけでなく、少なくとも1つの、好ましくは1つの、少なくとも1つの架橋性Q基を有する構造単位を有することを特徴とする、請求項1~7のいずれか一項に記載のポリマー。
- スズキ重合、ヤマモト重合、スティル重合、またはハートウィグ-ブッフバルト重合によって調製されることを特徴とする、請求項1~9のいずれか一項に記載のポリマーの調製方法。
- 少なくとも1つの式(Ia)の構造単位を含む請求項1~9のいずれか一項に記載の1以上のポリマー、および1以上のさらなる、ポリマーの、オリゴマーの、デンドリマーの、および/または低分子量の、物質を含んでなる、ポリマーブレンド。
- 1以上の溶媒中の、請求項1~9のいずれか一項に記載の1以上のポリマー、または請求項11に記載のポリマーブレンドから構成される、溶液または配合物。
- 電子または光電子素子、好ましくは有機エレクトロルミネッセンス素子(OLED)、有機発光電子化学電池(OLEC)、有機電界効果トランジスタ(OFET)、有機集積回路(O-IC)、有機薄膜トランジスタ(TFT)、有機太陽電池(O-SC)、有機レーザーダイオード(O-laser)、有機光起電力(OPV)要素もしくは素子、または有機光受容器(OPC)、より好ましくは有機エレクトロルミネッセンス素子(OLED)、における、請求項1~9のいずれか一項に記載のポリマーの使用。
- 1以上の活性層を有し、これらの活性層の少なくとも1つが請求項1~9のいずれか一項に記載の1以上のポリマーを含んでなる、電子または光電子素子、好ましくは有機エレクトロルミネッセンス素子(OLED)、有機発光電子化学電池(OLEC)、有機電界効果トランジスタ(OFET)、有機集積回路(O-IC)、有機薄膜トランジスタ(TFT)、有機太陽電池(O-SC)、有機レーザーダイオード(O-laser)、有機光起電力(OPV)要素もしくは素子、または有機光受容器(OPC)、より好ましくは有機エレクトロルミネッセンス素子(OLED)。
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JP6737264B2 (ja) * | 2015-03-31 | 2020-08-05 | 出光興産株式会社 | 交差共役系重合体、電子素子用材料、有機エレクトロルミネッセンス素子用材料及び有機エレクトロルミネッセンス素子 |
CN110577513A (zh) * | 2019-08-28 | 2019-12-17 | 武汉华星光电半导体显示技术有限公司 | 电致发光材料、电致发光材料的制备方法及发光器件 |
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JP6737264B2 (ja) * | 2015-03-31 | 2020-08-05 | 出光興産株式会社 | 交差共役系重合体、電子素子用材料、有機エレクトロルミネッセンス素子用材料及び有機エレクトロルミネッセンス素子 |
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2017
- 2017-11-27 US US16/465,344 patent/US20190296242A1/en not_active Abandoned
- 2017-11-27 KR KR1020197018727A patent/KR102431891B1/ko active IP Right Grant
- 2017-11-27 CN CN201780072460.7A patent/CN109983054B/zh active Active
- 2017-11-27 EP EP17804190.1A patent/EP3548535B1/de active Active
- 2017-11-27 JP JP2019528912A patent/JP7023957B2/ja active Active
- 2017-11-27 WO PCT/EP2017/080486 patent/WO2018099847A1/de unknown
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WO2008010487A1 (fr) | 2006-07-19 | 2008-01-24 | Hitachi Chemical Co., Ltd. | Matériau électronique organique, dispositif électronique organique et dispositif électroluminescent organique |
Also Published As
Publication number | Publication date |
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US20190296242A1 (en) | 2019-09-26 |
KR102431891B1 (ko) | 2022-08-12 |
CN109983054B (zh) | 2022-10-04 |
KR20190086550A (ko) | 2019-07-22 |
WO2018099847A1 (de) | 2018-06-07 |
CN109983054A (zh) | 2019-07-05 |
JP2020500976A (ja) | 2020-01-16 |
EP3548535A1 (de) | 2019-10-09 |
EP3548535B1 (de) | 2022-11-16 |
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