JP2014530943A - 多分岐ポリマー、その製造方法と電子素子でのその使用 - Google Patents
多分岐ポリマー、その製造方法と電子素子でのその使用 Download PDFInfo
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- JP2014530943A JP2014530943A JP2014537510A JP2014537510A JP2014530943A JP 2014530943 A JP2014530943 A JP 2014530943A JP 2014537510 A JP2014537510 A JP 2014537510A JP 2014537510 A JP2014537510 A JP 2014537510A JP 2014530943 A JP2014530943 A JP 2014530943A
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- 229920000587 hyperbranched polymer Polymers 0.000 title claims description 18
- 238000000034 method Methods 0.000 title abstract description 16
- 238000004519 manufacturing process Methods 0.000 title abstract description 12
- 229920000642 polymer Polymers 0.000 claims abstract description 84
- -1 phenoxatin Chemical compound 0.000 claims description 60
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 239000000463 material Substances 0.000 claims description 29
- 238000002347 injection Methods 0.000 claims description 28
- 239000007924 injection Substances 0.000 claims description 28
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 25
- 230000001737 promoting effect Effects 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 238000004090 dissolution Methods 0.000 claims description 16
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 16
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 15
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 14
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000006413 ring segment Chemical group 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000005259 triarylamine group Chemical group 0.000 claims description 9
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
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- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 7
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 7
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 7
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 7
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- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 5
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000468 ketone group Chemical group 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 230000005669 field effect Effects 0.000 claims description 4
- 125000005067 haloformyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 238000013086 organic photovoltaic Methods 0.000 claims description 4
- 229920002959 polymer blend Polymers 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 4
- NONOKGVFTBWRLD-UHFFFAOYSA-N thioisocyanate group Chemical group S(N=C=O)N=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 claims description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 3
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 3
- 229950000688 phenothiazine Drugs 0.000 claims description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000005580 triphenylene group Chemical group 0.000 claims description 3
- ZIZMDHZLHJBNSQ-UHFFFAOYSA-N 1,2-dihydrophenazine Chemical compound C1=CC=C2N=C(C=CCC3)C3=NC2=C1 ZIZMDHZLHJBNSQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000005401 electroluminescence Methods 0.000 claims description 2
- 150000002240 furans Chemical class 0.000 claims description 2
- NFBOHOGPQUYFRF-UHFFFAOYSA-N oxanthrene Chemical compound C1=CC=C2OC3=CC=CC=C3OC2=C1 NFBOHOGPQUYFRF-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 claims description 2
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 claims 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- 150000001875 compounds Chemical class 0.000 description 45
- 239000010410 layer Substances 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 229910052741 iridium Inorganic materials 0.000 description 33
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 31
- 239000000178 monomer Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 229910052799 carbon Inorganic materials 0.000 description 19
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 15
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- 239000002184 metal Substances 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- WDECIBYCCFPHNR-UHFFFAOYSA-N Chrysene Natural products C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 7
- 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 7
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- 125000003342 alkenyl group Chemical group 0.000 description 6
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- 125000001424 substituent group Chemical group 0.000 description 6
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 150000008648 triflates Chemical group 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Abstract
Description
(2)電極、多くは、金属もしくは無機であるが、有機もしくはポリマー伝導性材料からも作られる、
(3)電荷注入層もしくは中間層、たとえば、電極の不均性の補償用であり(「平坦化層」)、多くは、伝導性のドープされたポリマーから作られる、
(4)有機半導体、
(5)随意に、さらなる電荷輸送層もしくは電荷注入層もしくは電荷ブロック層、
(6)対電極、(2)で言及された材料
(7)外被。
A1は、機能性構造要素であり、
mは、3以上、好ましくは、10以上、特に、好ましくは、20以上の整数であり、
線はポリマーのさらなる単位への結合である。)
および少なくとも一つの一般式(II)の単位を含む、多分岐ポリマーに関する。
A2は、機能性構造要素、好ましくは、A1とは異なる機能性構造要素であり、
lは、1以上、好ましくは、10以上、特に、好ましくは、20以上の整数であり、
線はポリマーの別の単位への結合であって、少なくとも一つの一般式(I)の単位または少くとも一つの一般式(II)の単位は、一般式(III)の溶解性促進単位から選ばれ;
Ar1、Ar2、Ar3は、夫々、互いに独立して、一以上の任意の所望の基R1により置換されてよいアリールもしくはヘテロアリール基であり、
Xは、各場合に、互いに独立して、NまたはCR2、好ましくは、CHであり、
R1、R2は、夫々、互いに独立して、水素、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、または3〜40個のC原子を有する分岐あるいは環式のアルキル、アルコキシもしくはチオアルコキシ基、またはシリル基もしくは1〜40個のC原子を有する置換ケト基、または2〜40個のC原子を有するアルコキシカルボニル基、または7〜40個のC原子を有するアリールオキシカルボニル基、シアノ基(-CN)、カルバモイル基(-C(=O)NH2)、ハロホルミル基(-C(=O)-X、Xはハロゲン原子である)、ホルミル基(-C(=O)-H)、イソシアノ基、イソシアネート基、チオシアネート基もしくはチオイソシアネート基、ヒドロキシル基、ニトロ基、CF3基、Cl、Br、F、架橋可能基、5〜60個の環原子を有する置換あるいは非置換芳香族もしくは複素環式芳香族環構造、5〜60個の環原子を有する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これら構造の組み合わせであり、ここで、一以上の基R1および/またはR2は、互いに、および/または基R1が結合する環とともに、モノ-あるいはポリ環式の脂肪族もしくは芳香族環構造を形成してよく、
n、o、pは、互いに独立して、同一か、異なり、0または1であり、
ここで、一般式(III)の溶解性促進単位は、ポリマーが一般式(I)の単位であるならば、ポリマーのその他の単位への三つの結合を有し、かつ、一般式(III)の溶解性促進単位は、ポリマーが一般式(II)の単位であるならば、ポリマーの別の単位への一つの結合を有する。
群1:正孔注入および/または正孔輸送特性を有する単位。
正孔注入材料として使用することのできるさらなる構造要素は、EP 0891121 A1およびEP 1029909 A1に記載され、注入層は、一般的に、US 2004/0174116 A1に記載されている。
1,3,4-オキサジアゾール、たとえば、
CCyは、出現毎に同一であるか異なり、それを介して環式の基が金属に結合する炭素原子を含む環式の基であり、順に一以上の置換基R10を有してよく、
Aは、出現毎に同一であるか異なり、モノアニオン性二座キレートリガンド、好ましくは、ジケトネートリガンドであり、
R10は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CHO、C(=O)Ar3、P(=O)(Ar3)2、S(=O)Ar3、S(=O)2Ar3、CR11=CR11Ar3、CN、NO2、Si(R11)3、B(OR11)2、B(R11)2、B(N(R11)2)2、OSO2R11、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、2〜40個のC原子を有する直鎖アルケニルもしくはアルキニル基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基(夫々は、1以上の基R11により置換されてよく、1以上の隣接しないCH2基は、R11C=CR11、C≡C、Si(R11)2、Ge(R11)2、Sn(R11)2、C=O、C=S、C=Se、C=NR11、P(=O)(R11)、SO、SO2、NR11、O、SもしくはCONR11で置き代えられてよく、また、1以上のH原子は、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)、または、各場合に、1以上の基R11により置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、または、1以上の基R11により置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基、またはこれらの構造の組み合わせであり;ここで、2以上の隣接する置換基R10は、互いに、モノ-あるいはポリ環式の脂肪族もしくは芳香族環構造を形成してもよく;
Ar3は、出現毎に同一であるか異なり、1以上の基R11により置換されてよい5〜40個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
R11は、出現毎に同一であるか異なり、H、D、CNもしくは1〜20個のC原子を有する脂肪族、芳香族および/または複素環式芳香族炭化水素基であり、加えて、H原子は、Fで置き代えられてよく;ここで、2以上の隣接する置換基R11は、互いにモノ-あるいはポリ環式の、脂肪族もしくは芳香族環構造を形成してもよく、
ここで、少なくとも一つの前記基DCy、CCyおよび/またはAは、少なくとも一つの式(L-I)および/または(L-II)の基を含む。
特に、好ましい群4からの構造単位は、アントラセン、ベンゾアントラセンおよび/またはピレンを含むオリゴアリーレンもしくはこれら化合物のアトロプ異性体の種から選ばれる。本発明の意味でのオリゴアリーレンは、少なくとも三個のアリールもしくはアリーレン基が互いに結合する化合物を意味するものと解される。
フェンならびにジベンゾチオフェン誘導体を含む。
−電子注入および/または電子輸送特性を有する単位、および
−発光特性を有する単位で、一般式(II)の単位が、一般式(III)の溶解促進構造単位から選ばれる。
第2の好ましい態様では、一般式(I)の単位は、一般式(III)の溶解促進構造単位から選ばれ、かつ、一般式(II)の単位は、以下から選択される。
−電子注入および/または電子輸送特性を有する単位、
−発光特性を有する単位。
Ar1、Ar2は、夫々、互いに独立して、一以上の任意の所望の型の基R1により置換されてよいアリールもしくはヘテロアリール基であり、
Xは、各場合に、互いに独立して、NまたはCR2、好ましくは、CHであり、
R1、R2は、夫々、互いに独立して、水素、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、または3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基、またはシリル基もしくは1〜40個のC原子を有する置換ケト基、または2〜40個のC原子を有するアルコキシカルボニル基、または7〜40個のC原子を有するアリールオキシカルボニル基、シアノ基(-CN)、カルバモイル基(-C(=O)NH2)、ハロホルミル基(-C(=O)-X、ここで、Xはハロゲン原子である)、ホルミル基(-C(=O)-H)、イソシアノ基、イソシアネート基、チオシアネート基あるいはチオイソシアネート基、ヒドロキシル基、ニトロ基、CF3基、Cl、Br、F、架橋可能基、または5〜60個の環原子を有する置換あるいは非置換芳香族もしくは複素環式芳香族環構造、5〜60個の環原子を有する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これら構造の組み合わせであり、ここで、一以上の基R1および/またはR2は、互いにおよび/または基R1が結合する環とともに、モノ-あるいはポリ環式の、脂肪族もしくは芳香族環構造を形成してもよく、
n、o、pは、夫々、互いに独立して、0または1であり、
ここで、一般式(III)の溶解性促進単位は、ポリマーが一般式(I)の単位であるならば、ポリマーの他の単位への三つの結合を有し、一般式(III)の溶解性促進単位は、ポリマーが一般式(II)の単位であるならば、ポリマーの別の単位への一つの結合を有する。
sは、0、1、2、3または4であり、
tは、0、1、2または3であり、
u、vは、夫々、互いに独立して、0、1、2、3、4または5であり、
ここで、破線の結合は、多分岐ポリマーのさらなる単位への結合を示す。
A1は、機能性構造要素であり、
Xは、脱離基Yと反応する脱離基であり、
Yは、同一か異なり、好ましくは、同一であり、脱離基Xと反応する脱離基である。
19.5g(82.7ミリモル)の1,3-ブロモベンゼン(1)と24.0g(94.5ミリモル)のビス(ピナコラート)ジボロンが、150mlのシクロヘキサン中に懸濁される。1.50g(5.59ミリモル)のdtbpyと500mg(754マイクロモル)の[Ir(OMe)COD]2が、この懸濁液に添加され、混合物は、80℃で、16時間加熱される。冷却後、暗茶色の混合物が、300mlの氷水に添加され、300mlのジクロロメタンで3度その度毎に抽出される。有機相が分離され、水と塩水で洗浄され、Na2SO4で乾燥され、引き続き蒸発幹固される。粗生成物は、シリカゲル(CH2Cl2)上のカラムクロマトグラフにより精製され、収率は85%(24.8g、68.5ミリモル)で無色固形物として2を得る。
13C NMR(126MHz,CDCl3)δ=136.2,135.6,122.5,84.2,24.5.
APLI-HRMSm/e(C12H15BBr2O2):計算質量:359.9526[M]+、見出された質量:359.9537[M]+。
トルエン/THF/水混合物(8mlのトルエン、32mlのTHFと20mlのH2O)中の5.53ミリモルのモノマー(2)と塩基としての12.2ミリモルのK3PO4が、30分間脱気される。5.00mg(22マイクロモル)のPd(OAc)2と42.0mg(134マイクロモル)のP(o-tol)3が添加され、混合物は浴温度100℃で加熱される。ほんの数分後、黄色固形物が温度計上に沈殿する。TKF中の反復溶解とメタノール中での沈殿により、Mn=10300、Mw=16400で多分散度PD=1.6を有するHBP1を得る。ICP−MS測定により、臭素含量51%であり、フェニル単位毎に一個の臭素末端基に対応する。
13C NMR(126MHz,CDCl3)δ=141.4,128.8,126.1,83.3,24.6,21.9.
APLI-HRMSm/e(C14H21BO2):計算質量:232.1629[M]+、見出された質量:232.1627[M]+
第2工程(6)
13C NMR(126MHz,CDCl3)δ=144.4,138.6,135.4,132.1,130.6,127.5,127.2,122.7, 0.4.
EI-MS m/e(C14H12Br2):計算質量:337.931[M]+、見出された質量: 337.930 [M]+。
13C NMR(126MHz,CDCl3) δ=144.3,141.5,134.7,133.5,132.1,130.3,122.7,83.5,24.5, 20.2.
ESI-HRMS m/e(C20H23BBr2O2):計算質量:465.0231[M+H]+、見出された質量:465.0229[M+H]+。
25.2g(53.1ミリモル)の(9,10-ジ-2-ナフチル)-2--アントラセンボロン酸が、水分離機をもつフラスコ中の700mlのトルエン中の12.5g(106ミリモル)の無水ピナコールとともに、4時間還流下加熱される。冷却後、溶媒は減圧下除去され、粗生成物は、n-ヘプタン/THFから再結晶化され、収率が94%(27.9g、50.1ミリモル)で黄色固形物としてモノマー(9)を得る。
13C NMR(126MHz,CDCl3)δ=138.3,136.9,136.7,136.5,135.6,133.5, 133.5, 132.9, 132.8, 131.1,130.8,130.5,130.3,129.9,129.7,129.4,129.3,128.4,128.2,128.0,128.0,128.0,127.4,127.0,126.4,126.3,126.2,126.1,126.0,125.5,125.0,83.8,24.8.
ESI-HRMS m/e(C40H33BO2):計算質量:556.2573[M] +、見出された質量:557.2633[M+H] +
B)ポリマーの調製
13C NMR(126MHz,CDCl3)δ=149.62,146.17,136.13,132.48,126.15,122.50,116.18, 83.75, 24.89.
APCI-HRMS m/e (C24H24BBr2NO2):計算質量:528.0340 [M+H] +、見出された質量:528.0327 M+H] +.
B)モノマー(11)の重合
5.53ミリモルのモノマー(11)とトルエン/THF/水混合物(8mlのトルエン、32mlのTHFと20mlのH2O)中の12.2ミリモルの塩基としてのK3PO4が、30分間脱気される。5.00mg(22マイクロモル)のPd(OAc)2と42.0mg(134マイクロモル)のP(o-tol)3が添加され、混合物は100℃の浴温度で1.5時間加熱される。
OLED素子の製造
正孔輸送材料の素子データ
例7で調製された多分岐ポリマーHBP7とHBP8が、青色発光OLEDでの正孔輸送材料として使用される。
光電子特性決定のために、例11と12で製造されたOLEDは、基板サイズに対して特別に製造されたホルダーに把持され、ばね接点で供される。アイレスポンスフィルターを有するフォトダイオードは、外部光による影響を排除するために、測定ホルダー上に直接置くことができる。
Claims (12)
- 少なくとも一つの一般式(I)の単位を含み、
A1は、機能性構造要素であり、
mは、3以上の整数であり、
線はポリマーのさらなる単位への結合である。)
および少なくとも一つの一般式(II)の単位を含む、多分岐ポリマー。
A2は、機能性構造要素、好ましくは、A1とは異なる機能性構造要素であり、
lは、1以上の整数であり、
線は、ポリマーの別の単位への結合であって、少なくとも一つの一般式(I)の単位または少くとも一つの一般式(II)の単位は、一般式(III)の溶解性促進単位から選ばれる;
Ar1、Ar2、Ar3は、夫々、互いに独立して、一以上の任意の所望の基R1により置換されてよいアリールもしくはヘテロアリール基であり、
Xは、各場合に、互いに独立して、NまたはCR2、好ましくは、CHであり、
R1、R2は、夫々、互いに独立して、水素、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、または3〜40個のC原子を有する分岐あるいは環式のアルキル、アルコキシもしくはチオアルコキシ基、またはシリル基もしくは1〜40個のC原子を有する置換ケト基、または2〜40個のC原子を有するアルコキシカルボニル基、または7〜40個のC原子を有するアリールオキシカルボニル基、シアノ基(-CN)、カルバモイル基(-C(=O)NH2)、ハロホルミル基(-C(=O)-X、ここで、Xはハロゲン原子である)、ホルミル基(-C(=O)-H)、イソシアノ基、イソシアネート基、チオシアネート基もしくはチオイソシアネート基、ヒドロキシル基、ニトロ基、CF3基、Cl、Br、F、架橋可能基、5〜60個の環原子を有する置換あるいは非置換芳香族もしくは複素環式芳香族環構造、5〜60個の環原子を有する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これら構造の組み合わせであり、ここで、一以上の基R1および/またはR2は、互いに、および/または基R1が結合する環とともに、モノ-あるいはポリ環式の脂肪族もしくは芳香族環構造を形成してよく、
n、o、pは、互いに独立して、同一か、異なり、0または1であり、
ここで、一般式(III)の溶解性促進単位は、ポリマーが一般式(I)の単位であるならば、ポリマーの他の単位への三つの結合を有し、かつ、一般式(III)の溶解性促進単位は、ポリマーが一般式(II)の単位であるならば、ポリマーの別の単位への一つの結合を有する。) - 機能性構造要素A1またはA2は、正孔注入および/または正孔輸送特性を有し、トリアリールアミン、ベンジジン、テトラアリール-パラ-フェニレンジアミン、トリアリールホスフィン、フェノチアジン、フェノキサジン、ジヒドロフェナジン、チアントレン、ジベンゾ-パラ-ジオキシン、フェノキサチン、カルバゾール、アズレン、チオフェン、ピロールおよびフラン誘導体ならびに高HOMO(HOMO=最高占分子軌道)を有する更なるO-、S-もしくはN-含有へテロ環から選ばれることを特徴とする、請求項1記載のポリマー。
- 機能性構造要素A1またはA2は、電子注入および/または電子輸送特性を有し、ピリジン、ピリミジン、ピリダジン、ピラジン、オキサジアゾール、キノリン、キノキサリン、アントラセン、ベンズアントラセン、ピレン、ペリレン、ベンズイミダゾール、トリアジン、トリフェニレン、ケトン、ホスフインオキシドおよびフェナジン誘導体のみならずトリアリールボランならびに低LUMO(LUMO=最低空分子軌道)を有する更なるO-、S-もしくはN-含有へテロ環から選ばれることを特徴とする、請求項1記載のポリマー。
- 機能性構造要素A1またはA2は、発光する構造要素であり、蛍光および燐光エミッターから選ばれることを特徴とする、請求項1記載のポリマー。
- 機能性構造要素A1またはA2は、ホスト材料である構造要素であり、オリゴアリーレンから選ばれることを特徴とする、請求項1記載のポリマー。
- 機能性構造要素A1またはA2は、一般式(III)の溶解促進単位であることを特徴とする、請求項1記載のポリマー:
Ar1、Ar2、Ar3は、夫々、互いに独立して、一以上の任意の所望の基R1により置換されてよいアリールもしくはヘテロアリール基であり、
Xは、各場合に、互いに独立して、NまたはCR2、好ましくは、CHであり、
R1、R2は、夫々、互いに独立して、水素、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、または3〜40個のC原子を有する分岐あるいは環式のアルキル、アルコキシもしくはチオアルコキシ基、またはシリル基もしくは1〜40個のC原子を有する置換ケト基、または2〜40個のC原子を有するアルコキシカルボニル基、または7〜40個のC原子を有するアリールオキシカルボニル基、シアノ基(-CN)、カルバモイル基(-C(=O)NH2)、ハロホルミル基(-C(=O)-X、ここで、Xはハロゲン原子である)、ホルミル基(-C(=O)-H)、イソシアノ基、イソシアネート基、チオシアネート基もしくはチオイソシアネート基、ヒドロキシル基、ニトロ基、CF3基、Cl、Br、F、架橋可能基、5〜60個の環原子を有する置換あるいは非置換芳香族もしくは複素環式芳香族環構造、5〜60個の環原子を有する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これら構造の組み合わせであり、ここで、一以上のR1および/またはR2は、互いに、および/または基R1が結合する環とともに、モノ-あるいはポリ環式の脂肪族もしくは芳香族環構造を形成してもよく、
n、o、pは、互いに独立して、同一か、異なり、0または1であり、
ここで、一般式(III)の溶解性促進単位は、ポリマーが一般式(I)の単位であるならば、ポリマーのその他の単位への三つの結合を有し、かつ、一般式(III)の溶解性促進単位は、ポリマーが一般式(II)の単位であるならば、ポリマーの別の単位への一つの結合を有する。) - 一般式(I)の単位が、以下から選択されることを特徴とする、請求項1〜6何れか一項記載のポリマー:
−正孔注入および/または正孔輸送特性を有する請求項2記載の単位、
−電子注入および/または電子輸送特性を有する請求項3記載の単位、
−発光特性を有する請求項4記載の単位であって、一般式(II)の単位が請求項6記載の一般式(III)の溶解促進構造単位から選ばれる。 - 一般式(I)の単位が、請求項6記載の一般式(III)の溶解促進構造単位から選ばれ、かつ、一般式(II)の単位が、以下から選択されることを特徴とする、請求項1〜7何れか一項記載のポリマー:
−正孔注入および/または正孔輸送特性を有する請求項2記載の単位、
−電子注入および/または電子輸送特性を有する請求項3記載の単位、
−発光特性を有する請求項4記載の単位。 - 一以上の請求項1〜8何れか一項記載の多分岐ポリマーと一以上のさらなるポリマー状、オリゴマー状、樹状または低分子量物質を含むポリマー混合物。
- 一以上の溶媒中に一以上の請求項1〜8何れか一項記載の多分岐ポリマーまたは請求項9記載のポリマー混合物とを含む調合物。
- 請求項1〜8何れか一項記載の多分岐ポリマー、請求項9記載のポリマー混合物および請求項10記載の調合物の電子または光電子素子での使用。
- 一以上の活性層を有し、少なくとも一つのこれらの活性層は、一以上の請求項1〜8何れか一項記載の多分岐ポリマーを含む電子または光電子素子、好ましくは、有機もしくはポリマー有機エレクトロルミネッセンス素子(OLED、PLED)、有機電界効果トランジスタ(O-FET)、有機集積回路(O-IC)、有機薄膜トランジスタ(O-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(OPV)要素もしくは素子または有機光受容器(OPC)、特に、有機もしくはポリマーエレクトロルミッセンス素子、特に、ポリマー有機エレクトロルミッセンス素子。
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US20140339476A1 (en) | 2014-11-20 |
DE102011117422A1 (de) | 2013-05-02 |
US9825228B2 (en) | 2017-11-21 |
EP2771386B1 (de) | 2017-03-01 |
WO2013060411A1 (de) | 2013-05-02 |
JP6293663B2 (ja) | 2018-03-14 |
EP2771386A1 (de) | 2014-09-03 |
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