JP2020033356A - 電子素子用材料 - Google Patents
電子素子用材料 Download PDFInfo
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- JP2020033356A JP2020033356A JP2019183811A JP2019183811A JP2020033356A JP 2020033356 A JP2020033356 A JP 2020033356A JP 2019183811 A JP2019183811 A JP 2019183811A JP 2019183811 A JP2019183811 A JP 2019183811A JP 2020033356 A JP2020033356 A JP 2020033356A
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- aromatic ring
- organic
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- 239000000463 material Substances 0.000 title claims description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 193
- 125000003118 aryl group Chemical group 0.000 claims description 106
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- -1 NR 2 Inorganic materials 0.000 claims description 45
- 239000011159 matrix material Substances 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- 239000002019 doping agent Substances 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- 125000001931 aliphatic group Chemical group 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 229910052740 iodine Inorganic materials 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
- 125000003367 polycyclic group Polymers 0.000 claims description 15
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 230000000903 blocking effect Effects 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 10
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 125000004001 thioalkyl group Chemical group 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
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- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 2
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- 230000005669 field effect Effects 0.000 claims description 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 2
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- 238000010791 quenching Methods 0.000 claims description 2
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- 230000000171 quenching effect Effects 0.000 claims 1
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- 238000007740 vapor deposition Methods 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 230000004907 flux Effects 0.000 description 8
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 8
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- 150000001340 alkali metals Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
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- 238000003786 synthesis reaction Methods 0.000 description 7
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 6
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 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 4
- 0 CC1(*)C=CC(C2=C(C34C(C=C*(**)C=C5)=C5C5=C3C=C*(*)C=C5)C=CC(C)(*)C=C2)=C4C=C1 Chemical compound CC1(*)C=CC(C2=C(C34C(C=C*(**)C=C5)=C5C5=C3C=C*(*)C=C5)C=CC(C)(*)C=C2)=C4C=C1 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 150000002988 phenazines Chemical class 0.000 description 4
- 238000001126 phototherapy Methods 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
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- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
- UFWYLYLAKMJSCC-UHFFFAOYSA-N 2-[3-(7'-bromo-9,9'-spirobi[fluorene]-2'-yl)phenyl]-1-phenylbenzimidazole Chemical compound BrC1=CC=C2C=3C=CC(=CC=3C3(C4=CC=CC=C4C=4C=CC=CC3=4)C2=C1)C=1C=C(C=CC=1)C1=NC2=C(N1C1=CC=CC=C1)C=CC=C2 UFWYLYLAKMJSCC-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
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- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 3
- JCWIWBWXCVGEAN-UHFFFAOYSA-L cyclopentyl(diphenyl)phosphane;dichloropalladium;iron Chemical compound [Fe].Cl[Pd]Cl.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 JCWIWBWXCVGEAN-UHFFFAOYSA-L 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
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Abstract
Description
且つ、式(GK−1)で表される骨格並びに式(G−2)および(G−3)で表される基が互いに共有結合しているか、または代わりに式(GK−2)で表される骨格並びに式(G−2)および(G−3)で表される基が互いに共有結合しており、
且つ、使用される記号および添え字には以下の定義が適用されることを特徴とする化合物に関する:
ここで、上記の定義が、使用された記号および添え字に適用され、それらの好ましい態様はまた、式(23)で表される化合物の好ましい態様を表わす。
ここで、Abは、好ましくはCl、Br、Iおよびトリフラートから選択される脱離基を表し、非常に好ましくはBrである。また、ここではピナコールボロン酸エステルに加えて、その他のエステルもしくはボロン酸自体も使用することができる。これらは、当業者に非常に良く知られている。
LUMO(eV)=((LEh*27.212)−2.0041)/1.385
エレクトロルミネッセンス素子であり、さらに、ここでは特に、OLEDである。
実施例1
2−[3−[7′−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)−9,9′−スピロビ[フルオレン]−2′−イル]フェニル]−1−フェニルベンゾイミダゾール6aの合成
保護ガス下で2リットルの四つ口フラスコに、400ミリリットルのトルエン、400ミリリットルの1,4−ジオキサンおよび200ミリリットルの脱イオン水中の、50.0g(105ミリモル、1.00当量)の2,7−ジブロモ−9,9′−スピロビフルオレン1a、41.7g(105ミリモル、1.00当量)の1−フェニル−2− [3−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)フェニル]−1H−ベンゾイミダゾール2aおよび36.4g(263ミリモル、2.50当量)の炭酸カリウムを初期導入し、さらに脱気する。引き続いて、1.22g(1.05ミリモル、0.01当量)のテトラキス(トリフェニルホスフィン)パラジウム(0)を添加し、さらに混合物を還流下で一晩加熱する。反応が終了したら、バッチを冷却し、セライトで濾過し、さらに1リットルのトルエンで希釈する。溶液を各回300ミリリットルの半飽和塩化ナトリウム溶液で3回洗浄し、硫酸ナトリウムで乾燥後、ロータリーエバポレーターで約200ミリリットルに濃縮する。沈殿した固体を濾過し、さらに真空下で乾燥させる。二置換の副生成物を昇華により分離し、22.0g(33.1ミリモル、32%)の所望の生成物3aを得る。
手順は、変形体Aのそれと同様に行なうが、ここでは、テトラキス(トリフェニルホスフィン)パラジウム(0)の代わりに0.01当量の酢酸パラジウム(II)および0.01当量のジシクロヘキシル(2′,6′−ジメトキシビフェニル−2−イル)−ホスフィン(SPhos)を使用する。
1リットルの四つ口フラスコに、500ミリリットルの乾燥した1,4−ジオキサン中の、22.0g(33.1ミリモル、1.00当量)の2−[3−(7′−ブロモ−9,9′−スピロビ[フルオレン]−2′−イル)フェニル]−1−フェニルベンゾイミダゾール3a、8.84g(30.1ミリモル、0.91当量)のビス(ピナコラト)ジボロンおよび26.0g(265ミリモル、8.00当量)の酢酸カリウムを初期導入し、さらに30分間脱気する。引き続いて、812mg(0.995ミリモル、0.0300当量)の1,1−ビス(ジフェニルホスフィノ)フェロセンジクロロパラジウム(II)のDCMとの錯体を添加し、さらに混合物を80℃の内部温度に加熱する。一晩撹拌した後、バッチを冷却し、さらに沈殿した固体を吸引濾過する。濾液をロータリーエバポレーターで約50ミリリットルに濃縮し、さらに沈殿した固体を同様に吸引濾過する。固体を合わせ、さらに乾燥させ、21.0g(29.5ミリモル、89%)のボロン酸エステル4aを得る。
変形体A
1リットルの三つ口フラスコに、200ミリリットルのトルエン、200ミリリットルの1,4−ジオキサンおよび100ミリリットルの脱イオン水中の、21.0g(29.5ミリモル、1.00当量)の1−フェニル−2−[3−[7′−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)−9,9′−スピロビ[フルオレン]−2′−イル]フェニル]ベンゾイミダゾール4aおよび7.90g(29.5ミリモル、1.00当量)の2−クロロ−4,6−ジフェニル−1,3,5−トリアジン5a並びに3.75g(35.4ミリモル、1.20当量)の炭酸ナトリウムを初期導入し、さらに20分間脱気する。1.02g(0.885ミリモル、0.0300当量)のテトラキス(トリフェニルホスフィン)パラジウム(0)を添加した後、バッチを還流下で2日間加熱し、さらに反応が終了したら冷却する。沈殿した固体を吸引濾過し、水と少量のトルエンで洗浄し、さらに引き続いてHPLC純度>99.9%が達成されるまでトルエン/ヘプタンから多数回再結晶させる。昇華により、11.5g(14.0ミリモル、43%)の無色の固体6aを得る。
手順は、変形体Aのそれと同様に行なうが、ここでは、テトラキス(トリフェニルホスフィン)パラジウム(0)の代わりに0.01当量の酢酸パラジウム(II)および0.04当量のトリ(o−トリル)ホスフィンを使用する。
手順は、変形体Aのそれと同様に行なうが、ここでは、テトラキス(トリフェニルホスフィン)パラジウム(0)の代わりに0.01当量の酢酸パラジウム(II)および0.01当量のジシクロヘキシル(2′,6′−ジメトキシ−ビフェニル−2−イル)−ホスフィン(SPhos)を使用する。
変形体A
保護ガス下で2リットルの四つ口フラスコに、300ミリリットルのトルエン、300ミリリットルの1,4−ジオキサンおよび300ミリリットルの脱イオン水中の、24.5g(67.9ミリモル、1.00当量)の9,9′−スピロビフルオレン−2′−イルボロン酸7a、15.4g(68.3ミリモル、1.01当量)の2,4−ジクロロ−6−フェニル−1,3,5−トリアジン8aおよび9.04g(85.3ミリモル、1.26当量)の炭酸ナトリウムを初期導入し、さらに脱気する。引き続いて、0.850g(0.736ミリモル、0.01当量)のテトラキス(トリフェニルホスフィン)パラジウム(0)を添加し、さらに、混合物を還流下で24時間加熱する。反応の終了後、バッチを冷却し、さらに100ミリリットルの酢酸エチルで希釈する。相を分液漏斗で分離し、水相を酢酸エチルで3回抽出し、さらに、合わせた有機相を水でもう一度洗浄する。次いで、混合物を硫酸ナトリウムで乾燥させ、さらに、溶液を黄褐色の固体が沈殿するまで濃縮する。固体を濾過し、熱エタノールで撹拌することにより洗浄し、さらに再濾過の後、真空下で乾燥させる。溶離液としてヘプタン/ジクロロメタン5:1を用いたカラムクロマトグラフィーにより生成物を精製し、9.90g(19.6ミリモル、29%)の無色の固体を得る。
手順は、変形体Aのそれと同様に行なうが、ここでは、テトラキス(トリフェニルホスフィン)パラジウム(0)の代わりに0.01当量の酢酸パラジウム(II)および0.04当量のトリ(o−トリル)ホスフィンを使用する。
手順は、変形体Aのそれと同様に行なうが、ここでは、テトラキス(トリフェニルホスフィン)パラジウム(0)の代わりに0.01当量の酢酸パラジウム(II)および0.01当量のジシクロヘキシル(2′,6′−ジメトキシビフェニル−2−イル)−ホスフィン(SPhos)を使用する。
手順は、変形体Aのそれと同様に行なうが、ここでは、テトラキス(トリフェニルホスフィン)パラジウム(0)の代わりに0.02当量の1,1−ビス(ジフェニルホスフィノ)フェロセンジクロロパラジウム(II)のDCMとの錯体を使用し、さらに溶媒として乾燥したトルエンを使用する。
変形体A
250ミリリットルの三つ口フラスコに、35ミリリットルのトルエン、35ミリリットルの1,4−ジオキサンおよび35ミリリットルの脱イオン水中の、9.90g(19.6ミリモル、1 0.00当量)の2−クロロ−4−フェニル−6−(9,9′−スピロビ[9H−フルオレン]−2−イル)−1,3,5−トリアジン9a、8.53g(21. 5ミリモル、1.10当量)の1−フェニル−2−[3−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)−フェニル]−1H−ベンゾイミダゾール10aおよび4.57g(43.1ミリモル、2.20当量)の炭酸ナトリウムを初期導入し、さらに脱気する。引き続いて、1.13g(0.980ミリモル、0.05当量)のテトラキス(トリフェニルホスフィン)パラジウム(0)を添加し、さらに混合物を還流下で48時間加熱する。反応が終了したらバッチを冷却し、さらに沈殿した固体を吸引濾過する。得られた粗生成物を、抽出、ヘプタン/トルエンからの3回の再結晶および昇華により精製し、4.83g(6.54ミリモル、33%)の、HPLC純度>99.9%を有する固体を得る。
手順は、変形体Aのそれと同様に行なうが、ここでは、テトラキス(トリフェニルホスフィン)パラジウム(0)の代わりに0.02当量の1,1−ビス(ジフェニルホスフィノ)フェロセンジクロロパラジウム(II)のDCMとの錯体を使用し、さらに溶媒として乾燥したトルエンを使用する。
150ミリリットルのTHF中の、10.2g(22.2ミリモル、1.00当量)の2−ビフェニル−3−イル−4−クロロ−6−(9,9−ジメチル−9H−フルオレン−2−イル)−1,3,5−トルイジン9kおよび4.31g(22.2ミリモル、1.00当量)の2−フェニル−1H−ベンゾイミダゾール10kの溶液に、4.15ミリリットル(24.4ミリモル、1.10当量)のジイソプロピルエチルアミン(ヒューニッヒ塩基)を室温で添加する。反応混合物を、一晩撹拌し、さらに、反応が終了したら、溶媒を真空下で除去する。200ミリリットルのジクロロメタンを加えた後、溶液を水で3回抽出し、硫酸ナトリウムで乾燥し、さらに溶媒をロータリーエバポレーターで除去する。変形体Aと同様に精製を行ない、5.57g(9.02ミリモル、41%)の、所望の生成物11kを得る。
OLEDの製造および特性評価
以下の実施例V1〜E16に種々のOLEDについてのデータを示す(表1および2参照)。
OLED中の電子注入および電子輸送層での使用において、本発明の材料は、成分の寿命および/または効率に関して従来技術に優る著しい改善をもたらす。本発明に従う化合物EG1の使用は、従来技術と比較して寿命を20%〜40%増大させることを可能にする(実施例V1およびV2とE1との比較並びにV3とE2との比較)。本発明に係る化合物の更なる技術的利点は、従来技術と比較して効率を約10%の増加させることである(実験V1とE1との比較)。
Claims (19)
- 下記の一般式(24)を有する化合物。
R5は、出現毎に同一であるかまたは異なり、F、Cl、Br、I、CHO、N(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CR2=CR2Ar1、CN、NO2、Si(R2)3、B(OR2)2、B(R2)2、B(N(R2)2)2、OSO2R2、1〜40個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キル基、または2〜40個の炭素原子を有する、直鎖の、アルケニルもしくはアルキニル基、または3〜40個の炭素原子を有する、分岐状もしくは環状の、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(これらのそれぞれは、1つ以上のラジカルR2により置換されていてもよく、ここで1つ以上のCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2で置き替えられていてもよく、またここで、1つ以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き替えられていてもよい)、または5〜60個の芳香族環原子を有する、芳香族もしくはヘテロ芳香族環系(これらは、それぞれの場合において1つ以上のラジカルR2で置換されていてもよい)、または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(これらは、1つ以上のラジカルR2で置換されていてもよい)、またはこれらの系の組合せであり;ここで、2つ以上の隣接する置換基R5は互いに、単−もしくは多−環状の、脂肪族もしくは芳香族環系を形成することができず;
R4およびR6は、出現毎に同一であるかまたは異なり、H、D、F、Cl、Br、I、CHO、N(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CR2=CR2Ar1、CN、NO2、Si(R2)3、B(OR2)2、B(R2)2、B(N(R2)2)2、OSO2R2、1〜40個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キル基、または2〜40個の炭素原子を有する、直鎖の、アルケニルもしくはアルキニル基、または3〜40個の炭素原子を有する、分岐状もしくは環状の、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(これらのそれぞれは、1つ以上のラジカルR2により置換されていてもよく、ここで1つ以上のCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2で置き替えられていてもよく、またここで、1つ以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き替えられていてもよい)、または5〜60個の芳香族環原子を有する、芳香族もしくはヘテロ芳香族環系(これらは、それぞれの場合において1つ以上のラジカルR2で置換されていてもよい)、または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(これらは、1つ以上のラジカルR2で置換されていてもよい)、またはこれらの系の組合せであり;ここで、2つ以上の隣接する置換基R4は互いに、単−もしくは多−環状の、脂肪族もしくは芳香族環系を形成することができず;
R2は、出現毎に同一であるかまたは異なり、H、D、F、Cl、Br、I、N(R3)2、CN、NO2、Si(R3)3、B(OR3)2、C(=O)R3、P(=O)(R3)2、S(=O)R3、S(=O)2R3、OSO2R3、1〜40個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キル基、または2〜40個の炭素原子を有する、直鎖の、アルケニルもしくはアルキニル基、または3〜40個の炭素原子を有する、分岐状もしくは環状の、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(これらのそれぞれは、1つ以上のラジカルR3により置換されていてもよく、ここで1つ以上の非隣接CH2基は、R3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、SもしくはCONR3で置き替えられていてもよく、またここで、1つ以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き替えられていてもよい)、または5〜60個の芳香族環原子を有する、芳香族もしくはヘテロ芳香族環系(これらは、それぞれの場合において1つ以上のラジカルR3で置換されていてもよい)、または5〜60個の芳香族環原子を有する、アリールオキシ、アリールアルコキシもしくはヘテロアリールオキシ基(これらは、1つ以上のラジカルR3で置換されていてもよい)、または10〜40個の芳香族環原子を有する、ジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基(これらは、1つ以上のラジカルR3で置換されていてもよい)、または2つ以上のこれらの系の組合せであり;ここで、2つ以上の隣接する置換基R2は互いに、単−もしくは多−環状の、脂肪族もしくは芳香族環系を形成していてもよく;
Qは、C=O、C=S、S、C(R2)2、NR2またはOであり; nは、0または1であり;
pは、0または1であり;
qは、0または1であり;
Xは、出現毎に同一であるかまたは異なり、NまたはCR1であり; R1は、出現毎に同一であるかまたは異なり、H、D、F、Cl、Br、I、CHO、N(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CR2=CR2Ar1、CN、NO2、Si(R2)3、B(OR2)2、B(R2)2、B(N(R2)2)2、OSO2R2、1〜40個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キル基、または2〜40個の炭素原子を有する、直鎖の、アルケニルもしくはアルキニル基、または3〜40個の炭素原子を有する、分岐状もしくは環状の、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(これらのそれぞれは、1つ以上のラジカルR2により置換されていてもよく、ここで1つ以上のCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2で置き替えられていてもよく、またここで、1つ以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き替えられていてもよい)、または5〜60個の芳香族環原子を有する、芳香族もしくはヘテロ芳香族環系(これらは、それぞれの場合において1つ以上のラジカルR2で置換されていてもよい)、または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(これらは、1つ以上のラジカルR2で置換されていてもよい)、またはこれらの系の組合せであり;ここで、2つ以上の隣接する置換基R1は互いに、単−もしくは多−環状の、脂肪族もしくは芳香族環系を形成していてもよく; Ar1は、出現毎に同一であるかまたは異なり、5〜30個の芳香族環原子を有する芳香族もしくはヘテロ芳香族環系(これらは、1つ以上のラジカルR2で置換されていてもよい)であり;ここで、2つのラジカルAr1はまた、単結合、またはB(R2)、C(R2)2、Si(R2)2、C=O、C=NR2、C=C(R2)2、O、S、S=O、SO2、N(R2)、P(R2)およびP(=O)R2から選択される橋架により互いに結合していてもよく;
Q′は、出現毎に同一であるかまたは異なり、C=O、C=S、S、C(R2)2、NR2またはOであり;
aは、0または1であり;
bは、0または1であり;
mは、0または1であり;
Vは、芳香環Aまたは芳香環Gと芳香環Dとを接続する二価の基であり;
Uは、芳香環Bまたは芳香環Fと環Cとを接続する二価の基であり、ここでUはいずれかの置換基R 5 の代わりに環Cに結合しており;
vは、0または1であり、ここで、v=0は、環Dが単一の共有結合を介して直接、当該化合物の残りと接続されていることを意味し;
uは、0または1であり、ここで、u=0は、環Cが単一の共有結合を介して直接、当該化合物の残りと接続されていることを意味する。 - 前記化合物が3000g/モル以下の分子量を有する小さな分子であることを特徴とする、請求項1〜5のいずれか1項に記載の化合物。
- nが0であり、ここでn=0は、2つの芳香環AおよびBが、Q基を介して互いに結合しているのではなく、単結合により結合していることを意味している、請求項1〜6のいずれか1項に記載の化合物。
- mが0であり、ここでm=0は、2つの芳香環が、Q′基を介して互いに結合しているのではなく、単結合により結合されていることを意味している、請求項1〜7のいずれか1項に記載の化合物。
- a+bが0、1または2である、請求項1〜8のいずれか1項に記載の化合物。
- 少なくとも1つのXがNに等しい、請求項1〜9のいずれか1項に記載の化合物。
- 少なくとも2つのXがNに等しい、請求項1〜10のいずれか1項に記載の化合物。
- 請求項1〜11のいずれか一項に記載の化合物の少なくとも1つと、蛍光エミッター、燐光エミッター、マトリックス材料、電子輸送材料、電子注入材料、正孔伝導性材料、正孔注入材料、電子遮断材料および正孔遮断材料、ワイドバンドギャップ材料およびnドーパントからなる群から選択される更なる化合物の少なくとも1つとを含んでなる組成物。
- 追加の化合物が、電子輸送材料またはマトリックス材料であることを特徴とする請求項12に記載の組成物。
- 請求項1〜11のいずれか一項に記載の化合物の少なくとも1つ、または請求項12もしくは13に記載の組成物の少なくとも1つと、少なくとも1つの溶媒とを含んでなる調合物。
- 請求項1〜11のいずれか一項に記載の化合物の少なくとも1つ、または請求項12もしくは13に記載の組成物の少なくとも1つの、電子素子における使用。
- 請求項1〜11のいずれか一項に記載の化合物の少なくとも1つ、または請求項12もしくは13に記載の組成物の少なくとも1つを含んでなる電子素子。
- 有機集積回路(OIC)、有機電界効果トランジスタ(OFET)、有機薄膜トランジスタ(OTFT)、有機エレクトロルミネッセンス素子、有機太陽電池(OSC)、有機光検出器、有機光受容器から選択されることを特徴とする、請求項16に記載の電子素子。
- 有機発光トランジスタ(OLET)、有機電界クエンチイング素子(OFQD)、有機発光電気化学電池(OLEC、LEC、LEEC)、有機レーザーダイオード(O−laser)および有機発光ダイオード(OLED)であることを特徴とする、請求項16または17に記載の電子素子。
- 少なくとも1つの有機層を、気相蒸着により、または溶液から塗布することを特徴とする、請求項16〜18のいずれか一項に記載の電子素子を製造する方法。
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JP2021155420A (ja) | 2021-10-07 |
TW202100521A (zh) | 2021-01-01 |
CN116655603A (zh) | 2023-08-29 |
WO2016012075A1 (de) | 2016-01-28 |
KR102657649B1 (ko) | 2024-04-15 |
JP6893964B2 (ja) | 2021-06-23 |
TWI703140B (zh) | 2020-09-01 |
EP3172775B1 (de) | 2022-04-20 |
TW201615635A (zh) | 2016-05-01 |
TW202227400A (zh) | 2022-07-16 |
EP3172775A1 (de) | 2017-05-31 |
CN112010842A (zh) | 2020-12-01 |
JP6629291B2 (ja) | 2020-01-15 |
TWI763011B (zh) | 2022-05-01 |
EP4037000A1 (de) | 2022-08-03 |
JP2017524699A (ja) | 2017-08-31 |
KR102479149B1 (ko) | 2022-12-19 |
CN106536485A (zh) | 2017-03-22 |
US20170222157A1 (en) | 2017-08-03 |
KR20230006918A (ko) | 2023-01-11 |
JP7339982B2 (ja) | 2023-09-06 |
KR20170032414A (ko) | 2017-03-22 |
US10903430B2 (en) | 2021-01-26 |
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