JP2018518471A - 二重スピロ型有機化合物およびこれを含む有機電子素子 - Google Patents
二重スピロ型有機化合物およびこれを含む有機電子素子 Download PDFInfo
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- JP2018518471A JP2018518471A JP2017559402A JP2017559402A JP2018518471A JP 2018518471 A JP2018518471 A JP 2018518471A JP 2017559402 A JP2017559402 A JP 2017559402A JP 2017559402 A JP2017559402 A JP 2017559402A JP 2018518471 A JP2018518471 A JP 2018518471A
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000005564 oxazolylene group Chemical group 0.000 description 1
- UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- NQFOGDIWKQWFMN-UHFFFAOYSA-N phenalene Chemical compound C1=CC([CH]C=C2)=C3C2=CC=CC3=C1 NQFOGDIWKQWFMN-UHFFFAOYSA-N 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005560 phenanthrenylene group Chemical group 0.000 description 1
- 150000005053 phenanthridines Chemical class 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition 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
- 125000005504 styryl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- DBVXXBTUAZSUAY-UHFFFAOYSA-N tert-butyl(dimethyl)germanium Chemical group C[Ge](C)C(C)(C)C DBVXXBTUAZSUAY-UHFFFAOYSA-N 0.000 description 1
- 125000005557 thiazolylene group Chemical group 0.000 description 1
- AMIGYDGSJCJWSD-UHFFFAOYSA-N thiocane Chemical compound C1CCCSCCC1 AMIGYDGSJCJWSD-UHFFFAOYSA-N 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 125000005033 thiopyranyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229940110851 tolazine Drugs 0.000 description 1
- JIVZKJJQOZQXQB-UHFFFAOYSA-N tolazoline Chemical compound C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- YMSWJBZPRYKQHJ-UHFFFAOYSA-N triethylgermanium Chemical group CC[Ge](CC)CC YMSWJBZPRYKQHJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Abstract
Description
Claims (29)
- 下記化学式1で表され、
[化学式1]
R1〜R16のうちの少なくとも1つは、隣接した基と互いに結合して化学式1−1の環構造を形成し、
R1〜R16中の環を形成しない基は、それぞれ独立に、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミノ基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアラルキル基;置換もしくは非置換のアラルケニル基;置換もしくは非置換のアルキルアリール基;置換もしくは非置換のアルキルアミン基;置換もしくは非置換のアラルキルアミン基;置換もしくは非置換のヘテロアリールアミン基;置換もしくは非置換のアリールアミン基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基からなる群より選択され、
[化学式1−1]
mは、0〜5の整数であり、
mが2以上の場合に、Lは、互いに同一または異なり、
Lは、直接結合であるか;置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
Ar1は、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミノ基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアラルキル基;置換もしくは非置換のアラルケニル基;置換もしくは非置換のアルキルアリール基;置換もしくは非置換のアルキルアミン基;置換もしくは非置換のアラルキルアミン基;置換もしくは非置換のヘテロアリールアミン基;置換もしくは非置換のアリールアミン基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
前記(L)m−Ar1が非置換のフェニル基の場合には、前記R1〜R16中の化学式1−1の環を形成しない基は、水素であり、
R1a〜R4aは、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミノ基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアラルキル基;置換もしくは非置換のアラルケニル基;置換もしくは非置換のアルキルアリール基;置換もしくは非置換のアルキルアミン基;置換もしくは非置換のアラルキルアミン基;置換もしくは非置換のヘテロアリールアミン基;置換もしくは非置換のアリールアミン基;置換もしくは非置換のアリールヘテロアリールアミン基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であるか、隣接する基と互いに結合して置換もしくは非置換の環を形成してもよい、
二重スピロ型有機化合物。 - 前記化学式1は、下記化学式2〜化学式7のうちのいずれか1つで表されるものであり、
[化学式2]
R1〜R16は、それぞれ独立に、前記化学式1における定義と同じであり、
pおよびqは、それぞれ独立に、0〜5の整数であり、
pが2以上の場合、L1は、互いに同一または異なり、
qが2以上の場合、L2は、互いに同一または異なり、
L1およびL2は、それぞれ独立に、前記化学式1−1におけるLの定義と同じであり、
Ar1およびAr2は、それぞれ独立に、前記化学式1−1におけるAr1の定義と同じであり、
R1a〜R4aおよびR1b〜R4bは、それぞれ独立に、前記化学式1−1におけるR1a〜R4aの定義と同じである、請求項1に記載の二重スピロ型有機化合物。 - 前記化学式1は、下記化学式8〜化学式17のうちのいずれか1つで表されるものであり、
[化学式8]
R1〜R16は、それぞれ独立に、前記化学式1における定義と同じであり、
pは、0〜5の整数であり、
pが2以上の場合、L1は、互いに同一または異なり、
L1は、前記化学式1−1におけるLの定義と同じであり、
Ar1は、前記化学式1−1における定義と同じであり、
R1a〜R6aは、互いに同一または異なり、それぞれ独立に、前記化学式1−1における定義と同じである、請求項1または2に記載の二重スピロ型有機化合物。 - 前記R1〜R16中の環を形成しない基は、それぞれ独立に、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアラルキル基;置換もしくは非置換のアラルケニル基;置換もしくは非置換のアルキルアリール基;置換もしくは非置換のアルキルアミン基;置換もしくは非置換のアラルキルアミン基;置換もしくは非置換のヘテロアリールアミン基;置換もしくは非置換のアリールアミン基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアリール基;または環員15〜60の置換もしくは非置換のヘテロ環基からなる群より選択されるものである、請求項1から3のいずれか1項に記載の二重スピロ型有機化合物。
- Lがフェニレン基であるか、Ar1がフェニル基である場合、前記R1〜R16中の前記化学式1−1の環を形成しない基は、水素である、請求項4に記載の二重スピロ型有機化合物。
- 前記R1〜R16中の前記化学式1−1の環を形成しない基は、水素である、請求項4または5に記載の二重スピロ型有機化合物。
- 前記化学式1は、下記の構造から選択されたいずれか1である、
- 前記化学式1は、下記の構造から選択されたいずれか1である、
- 前記化学式1は、下記の構造から選択されたいずれか1つである、
- 前記化学式1は、下記の構造から選択されたいずれか1つである、
- 前記化学式1は、下記の構造から選択されたいずれか1つである、
- 前記化学式1は、下記の構造から選択されたいずれか1つである、
- 前記化学式1は、下記の構造から選択されたいずれか1つである、
- 第1電極と、第2電極と、前記第1電極と前記第2電極との間に配置された1層以上の有機物層とを含む有機電子素子であって、前記有機物層のうちの1層以上は、請求項1〜13のいずれか1項の二重スピロ型有機化合物を含むものである有機電子素子。
- 前記有機電子素子は、有機発光素子、有機太陽電池、および有機トランジスタからなる群より選択されるものである、請求項14に記載の有機電子素子。
- 前記有機電子素子は、第1電極と、第2電極と、前記第1電極と第2電極との間に配置された1層以上の有機物層とを含む有機発光素子であって、前記有機物層のうちの1層以上は、前記二重スピロ型有機化合物を含むものである、請求項14または15に記載の有機電子素子。
- 前記有機物層は、正孔注入層または正孔輸送層を含み、前記正孔注入層または正孔輸送層が前記二重スピロ型有機化合物を含むものである、請求項16に記載の有機電子素子。
- 前記有機物層は、発光層を含み、前記発光層が前記二重スピロ型有機化合物を発光層のホストとして含むものである、請求項16または17に記載の有機電子素子。
- 前記有機物層は、電子抑制層を含み、前記電子抑制層が前記化学式1の化合物を含む、請求項16から18のいずれか1項に記載の有機電子素子。
- 前記有機物層は、電子輸送層を含み、前記電子輸送層が前記二重スピロ型有機化合物を含むものである、請求項16から19のいずれか1項に記載の有機電子素子。
- 前記二重スピロ型有機化合物を含む有機物層は、前記二重スピロ型有機化合物をホストとして含み、他の有機化合物、金属または金属化合物をドーパントとして含むものである、請求項16から20のいずれか1項に記載の有機電子素子。
- 前記有機電子素子は、第1電極と、第2電極と、前記第1電極と第2電極との間に配置された光活性層を含む1層以上の有機物層とを含む有機太陽電池であって、前記有機物層のうちの1層以上は、前記二重スピロ型有機化合物を含むものである、請求項14から21のいずれか1項に記載の有機電子素子。
- 前記有機電子素子は、ソースと、ドレインと、ゲートと、1層以上の有機物層とを含む有機トランジスタであって、前記有機物層のうちの1層以上は、前記二重スピロ型有機化合物を含むものである、請求項14から22のいずれか1項に記載の有機電子素子。
- 前記有機物層は、下記化学式18の化合物を含む発光層を含むものであり、
[化学式18]
Ar3は、ベンゾフルオレン骨格、フルオランテン骨格、ピレン骨格、またはクリセン骨格であり、
L3は、単一結合、C6〜C30のアリーレン基、またはC5〜C30の2価のヘテロ環基であり、
X1およびX2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のC6〜C30のアリール基、置換もしくは非置換のC5〜C30のヘテロ環基、置換もしくは非置換のC1〜C30のアルキル基、および置換もしくは非置換のC7〜C30のアラルキル基からなる群より選択され、X1およびX2は、互いに結合して飽和または不飽和環を形成してもよく、
rは、1以上の整数であり、
前記rが2以上の場合、X1は、互いに同一または異なり、X2は、互いに同一または異なる、請求項14から23のいずれか1項に記載の有機電子素子。 - 前記Ar3は、ピレン骨格であり、L3は、単一結合であり、X1およびX2は、互いに同一または異なり、それぞれ独立に、ゲルマニウム基で置換もしくは非置換のアリール基であり、rが2である、請求項24に記載の有機電子素子。
- 前記有機物層は、下記化学式19の化合物を含む発光層を含むものであり、
[化学式19]
X5は、置換もしくは非置換の1−ナフチル基、置換もしくは非置換の2−ナフチル基、置換もしくは非置換の1−アントリル基、置換もしくは非置換の2−アントリル基、置換もしくは非置換の1−フェナントリル基、置換もしくは非置換の2−フェナントリル基、置換もしくは非置換の3−フェナントリル基、置換もしくは非置換の4−フェナントリル基、置換もしくは非置換の9−フェナントリル基、置換もしくは非置換の1−ナフタセニル基、置換もしくは非置換の2−ナフタセニル基、置換もしくは非置換の9−ナフタセニル基、置換もしくは非置換の1−ピレニル基、置換もしくは非置換の2−ピレニル基、置換もしくは非置換の4−ピレニル基、置換もしくは非置換の3−メチル−2−ナフチル基、置換もしくは非置換の4−メチル−1−ナフチル基、または下記構造式
X6は、フェニル基、1−ナフチル基、2−ナフチル基、1−アントリル基、2−アントリル基、9−アントリル基、1−フェナントリル基、2−フェナントリル基、3−フェナントリル基、4−フェナントリル基、9−フェナントリル基、1−ナフタセニル基、2−ナフタセニル基、9−ナフタセニル基、1−ピレニル基、2−ピレニル基、4−ピレニル基、2−ビフェニリル基、3−ビフェニリル基、4−ビフェニリル基、p−ターフェニル−4−イル基、p−ターフェニル−3−イル基、p−ターフェニル−2−イル基、m−ターフェニル−4−イル基、m−ターフェニル−3−イル基、m−ターフェニル−2−イル基、o−トリル基、m−トリル基、p−トリル基、p−t−ブチルフェニル基、p−(2−フェニルプロピル)フェニル基、3−メチル−2−ナフチル基、4−メチル−1−ナフチル基、4−メチル−1−アントリル基、4'−メチルビフェニリル基、4"−t−ブチル−p−ターフェニル−4−イル基、および3−フルオランテニル基からなる群より選択される基であり、
X3およびX4は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の炭素数6〜50のアリール基、置換もしくは非置換の核原子数5〜50のヘテロアリール基、置換もしくは非置換の炭素数1〜50のアルキル基、置換もしくは非置換の炭素数1〜50のアルコキシ基、置換もしくは非置換の炭素数6〜50のアラルキル基、置換もしくは非置換の核原子数5〜50のアリールオキシ基、置換もしくは非置換の核原子数5〜50のアリールチオ基、置換もしくは非置換の炭素数1〜50のアルコキシカルボニル基、カルボキシル基、ハロゲン原子、シアノ基、ニトロ基、またはヒドロキシル基であり、
s1およびs2はそれぞれ、0〜4の整数である、請求項14から25のいずれか1項に記載の有機電子素子。 - 前記X5およびX6は、互いに同一または異なり、それぞれ独立に、1−ナフチル基または2−ナフチル基であり、s1およびs2は、0である、請求項26に記載の有機電子素子。
- 前記発光層は、下記化学式19の化合物をさらに含むものであり、
[化学式19]
X5は、置換もしくは非置換の1−ナフチル基、置換もしくは非置換の2−ナフチル基、置換もしくは非置換の1−アントリル基、置換もしくは非置換の2−アントリル基、置換もしくは非置換の1−フェナントリル基、置換もしくは非置換の2−フェナントリル基、置換もしくは非置換の3−フェナントリル基、置換もしくは非置換の4−フェナントリル基、置換もしくは非置換の9−フェナントリル基、置換もしくは非置換の1−ナフタセニル基、置換もしくは非置換の2−ナフタセニル基、置換もしくは非置換の9−ナフタセニル基、置換もしくは非置換の1−ピレニル基、置換もしくは非置換の2−ピレニル基、置換もしくは非置換の4−ピレニル基、置換もしくは非置換の3−メチル−2−ナフチル基、置換もしくは非置換の4−メチル−1−ナフチル基、または下記構造式
X6は、フェニル基、1−ナフチル基、2−ナフチル基、1−アントリル基、2−アントリル基、9−アントリル基、1−フェナントリル基、2−フェナントリル基、3−フェナントリル基、4−フェナントリル基、9−フェナントリル基、1−ナフタセニル基、2−ナフタセニル基、9−ナフタセニル基、1−ピレニル基、2−ピレニル基、4−ピレニル基、2−ビフェニリル基、3−ビフェニリル基、4−ビフェニリル基、p−ターフェニル−4−イル基、p−ターフェニル−3−イル基、p−ターフェニル−2−イル基、m−ターフェニル−4−イル基、m−ターフェニル−3−イル基、m−ターフェニル−2−イル基、o−トリル基、m−トリル基、p−トリル基、p−t−ブチルフェニル基、p−(2−フェニルプロピル)フェニル基、3−メチル−2−ナフチル基、4−メチル−1−ナフチル基、4−メチル−1−アントリル基、4'−メチルビフェニリル基、4"−t−ブチル−p−ターフェニル−4−イル基、および3−フルオランテニル基からなる群より選択される基であり、
X3およびX4は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の炭素数6〜50のアリール基、置換もしくは非置換の核原子数5〜50のヘテロアリール基、置換もしくは非置換の炭素数1〜50のアルキル基、置換もしくは非置換の炭素数1〜50のアルコキシ基、置換もしくは非置換の炭素数6〜50のアラルキル基、置換もしくは非置換の核原子数5〜50のアリールオキシ基、置換もしくは非置換の核原子数5〜50のアリールチオ基、置換もしくは非置換の炭素数1〜50のアルコキシカルボニル基、カルボキシル基、ハロゲン原子、シアノ基、ニトロ基、またはヒドロキシル基であり、
s1およびs2はそれぞれ、0〜4の整数である、請求項24から27のいずれか1項に記載の有機電子素子。 - 前記化学式18のAr3は、ピレン骨格であり、L3は、単一結合であり、X1およびX2は、互いに同一または異なり、それぞれ独立に、ゲルマニウム基で置換もしくは非置換のアリール基であり、rが2であり、
前記化学式19におけるX5およびX6は、互いに同一または異なり、それぞれ独立に、1−ナフチル基または2−ナフチル基であり、s1およびs2は、0である、請求項28に記載の有機電子素子。
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JP6547850B2 (ja) | 2019-07-24 |
EP3305764A2 (en) | 2018-04-11 |
WO2016195458A3 (ko) | 2017-03-09 |
CN107709297A (zh) | 2018-02-16 |
EP3305764A4 (en) | 2018-12-26 |
WO2016195458A2 (ko) | 2016-12-08 |
EP3305764B1 (en) | 2019-09-25 |
CN107709297B (zh) | 2021-06-22 |
KR101826427B1 (ko) | 2018-02-06 |
US20180148640A1 (en) | 2018-05-31 |
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