JP7527019B2 - 化合物、有機光電子素子および表示装置 - Google Patents
化合物、有機光電子素子および表示装置 Download PDFInfo
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- JP7527019B2 JP7527019B2 JP2021542440A JP2021542440A JP7527019B2 JP 7527019 B2 JP7527019 B2 JP 7527019B2 JP 2021542440 A JP2021542440 A JP 2021542440A JP 2021542440 A JP2021542440 A JP 2021542440A JP 7527019 B2 JP7527019 B2 JP 7527019B2
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000012044 organic layer Substances 0.000 claims description 14
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000005576 pyrimidinylene 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
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 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
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 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
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 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
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 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
- 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
- 125000005558 triazinylene group Chemical group 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 238000002061 vacuum sublimation 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Description
前記化学式1において、Ar1は、置換もしくは非置換のC2~C60ヘテロアリール基であり、
Ar2およびAr3は、それぞれ独立して、置換もしくは非置換のC6~C60アリール基、または下記化学式3-1~3-4のいずれか1つであり、
L1~L3は、それぞれ独立して、単結合、置換もしくは非置換のC6~C60アリーレン基、または置換もしくは非置換のC2~C60ヘテロアリーレン基であり、
n1~n3は、互いに独立して、0~2の整数の1つであり、
R1~R6は、それぞれ独立して、水素、重水素、シアノ基、置換もしくは非置換のC1~C60アルキル基、または置換もしくは非置換のC6~C60アリール基である。
前記化学式1において、Ar1は、置換もしくは非置換のC2~C60ヘテロアリール基であり、Ar2およびAr3は、それぞれ独立して、置換もしくは非置換のC6~C60アリール基、または下記化学式3-1~3-4のいずれか1つであり、L1~L3は、それぞれ独立して、単結合、置換もしくは非置換のC6~C60アリーレン基、または置換もしくは非置換のC2~C60ヘテロアリーレン基であり、n1~n3は、互いに独立して、0~2の整数の1つであり、R1~R6は、それぞれ独立して、水素、重水素、シアノ基、置換もしくは非置換のC1~C60アルキル基、または置換もしくは非置換のC6~C60アリール基である。
前記化学式3-1~化学式3-4において、Xは、-O-、-S-、または-CRxRy-であり、RxおよびRyは、それぞれ独立して、水素、重水素、シアノ基、置換もしくは非置換のC1~C60アルキル基、またはC6~C60アリール基であるか、互いに融合して環を形成し、Rb~Reは、それぞれ独立して、水素、重水素、シアノ基、置換もしくは非置換のC1~C60アルキル基、またはC6~C60アリール基である。
前記化学式2-1~化学式2-5において、X1は、-NRx-、-O-、または-S-であり、
Rh~Riは、それぞれ独立して、水素、重水素、シアノ基、置換もしくは非置換のC1~C60アルキル基、置換もしくは非置換のC6~C60アリール基、または置換もしくは非置換のC2~C60ヘテロアリール基である。
前記化学式3-1~化学式3-4において、Xは、-O-、-S-、または-CRxRy-であり、RxおよびRyは、それぞれ独立して、水素、重水素、シアノ基、置換もしくは非置換のC1~C60アルキル基、またはC6~C60アリール基であり、Rb~Reは、それぞれ独立して、水素、重水素、シアノ基、置換もしくは非置換のC1~C60アルキル基、またはC6~C60アリール基である。
[製造例A1-1]中間体A(1)の合成
カルバゾール(Carbazole)(40g、1eq)、1-ブロモ-2-ヨードベンゼン(1-bromo-2-iodobenzene)(70g、1.5eq)、CuI(6.3g、0.2eq)、K3PO4(70g、2eq)、トランス-1,2-シクロヘキサンジアミン(trans-1,2-cyclohexanediamine)(19g、1eq)、およびトルエン(toluene)(600ml)を、1口丸底フラスコ(1-1-neck-round bottom flask、1-neck-r.b.f)に入れて撹拌した。(4時間(h))
前記撹拌が終わった反応液を、メチレンクロライド(Methylene chloride、MC)だけで濾過(filter)した後、カラム分離をして、P3を約65g得た。
Step yield=96%
P3(65g、1eq)、ビス(ピナコラト)ジボロン(bis(pinacolato)diboron)(65g、1.5eq)、PdCl2(dppf)(11g、0.1eq)、KOAc(50g、3eq)、およびジオキサン(Dioxane)800mlを、1口丸底フラスコ(1-1-neck-round bottom flask、1-neck-r.b.f)に入れて撹拌した。(6時間(h))
前記撹拌が終わった反応液を、シリカ/セライト(Silica/celite)を用いて濾過(filter)をして、P2を約60g得た。
Step yield=83%
P2(60g、1eq)、4-ブロモ-4’-ヨード1,1’-ビフェニル(4-bromo-4’-iodo1,1’-biphenyl)(63g、1.3eq)、Pd(Pph3)4(7.8g、0.05eq)、K2CO3(28g、1.5eq)、トルエン(toluene)600ml、エタノール(Ethanol)100ml、およびH2O100mlを、1口丸底フラスコ(1-1-neck-round bottom flask、1-neck-r.b.f)に入れて撹拌した。(4時間(h))
前記撹拌が終わった反応液を、メチレンクロライド(Methylene chloride、MC)だけで保温濾過(hot filter)を2回実施して、P1を33g得た。
Step yield=54%
中間体A(1)-P3の合成において、カルバゾール(carbazole)の代わりに2-フェニル-カルバゾール(2-phenyl-carbazole)を用いたことを除いてすべての段階を同様にして、中間体A(2)を合成した。
中間体A(1)-P3の合成において、カルバゾール(carbazole)の代わりに3-フェニル-カルバゾール(3-phenyl-carbazole)を用いたことを除いてすべての段階を同様にして、中間体A(3)を合成した。
中間体A(1)-P3の合成において、カルバゾール(carbazole)の代わりに4-フェニル-カルバゾール(4-phenyl-carbazole)を用いたことを除いてすべての段階を同様にして、中間体A(4)を合成した。
中間体A(1)-P3の合成において、カルバゾール(carbazole)の代わりに1-フェニル-カルバゾール(1-phenyl-carbazole)を用いたことを除いてすべての段階を同様にして、中間体A(5)を合成した。
中間体A(1)-P3の合成において、カルバゾール(carbazole)の代わりに2,7-フェニル-カルバゾール(2,7-phenyl-carbazole)を用いたことを除いてすべての段階を同様にして、中間体A(6)を合成した。
中間体A(1)-P3の合成において、カルバゾール(carbazole)の代わりに3,6-フェニル-カルバゾール(3,6-phenyl-carbazole)を用いたことを除いてすべての段階を同様にして、中間体A(7)を合成した。
中間体A(1)-P3の合成において、カルバゾール(carbazole)の代わりに2-(ナフタレン-1-イル)-9H-カルバゾール(2-(naphthalen-1-yl)-9H-carbazole)を用いたことを除いてすべての段階を同様にして、中間体A(8)を合成した。
中間体A(1)-P3の合成において、カルバゾール(carbazole)の代わりに2-(ジベンゾ[b,d]フラン-4-イル)-9H-カルバゾール(2-(dibenzo[b,d]furan-4-yl)-9H-carbazole)を用いたことを除いてすべての段階を同様にして、中間体A(9)を合成した。
中間体A(1)-P3の合成において、カルバゾール(carbazole)の代わりに2-(ジベンゾ[b,d]チオフェン-4-イル)-9H-カルバゾール(2-(dibenzo[b,d]thiophen-4-yl)-9H-carbazole)を用いたことを除いてすべての段階を同様にして、中間体A(10)を合成した。
4-ブロモ-ベンゼンアミン(4-bromo-benzenamine)(30g、1eq)、フェニルボロン酸(Phenyl boronicacid)(25.52g、1.5eq)、Pd(Pph3)4(10g、0.05eq)、K2CO3(36g、1.5eq)、トルエン(toluene)600ml、EtOH100ml、およびH2O100mlを、1口丸底フラスコ(1-1-neck-round bottom flask、1-neck-r.b.f)に入れて撹拌した。(3時間(h))
前記撹拌が終わった反応液を、メチレンクロライド(Methylene chloride、MC)およびヘキサン(Hexane、Hx)の比をMC:Hx=1:5としてシリカ濾過(silica filter)して、ビフェニルアミン(Biphenylamine)を19g得た。
Step yield=64%
ビフェニルアミン(Biphenylamine)(15g、1eq)、3-ブロモビフェニル(3-bromobiphenyl)(25g、1.2eq)、Pd2(dba)3(2.4g、0.03eq)、t-BuONa(12.5g、1.5eq)、t-Bu3P(1.05g、0.06eq)、およびトルエン(toluene)400mlを、1口丸底フラスコ(1-1-neck-round bottom flask、1-neck-r.b.f)に入れて撹拌した。(4時間(h))
前記撹拌が終わった反応液を、メチレンクロライド(Methylene chloride、MC)およびヘキサン(Hexane、Hx)の比をMC:Hx=1:5としてカラム分離して、N-[1,1’-ビフェニル]-3-イル[1,1’-ビフェニル]-4-アミン(N-[1,1’-Biphenyl]-3-yl[1,1’-biphenyl]-4-amine)を18g得た。(step yield=71%)
ビフェニルアミン(Biphenylamine)(19g、1.3eq)、4-(4-ブロモフェニル)-ジベンゾフラン(4-(4-bromophenyl)-Dibenzofuran)(28g、1eq)、Pd2(dba)3(2.4g、0.03eq)、t-BuONa(12.5g、1.5eq)、t-Bu3P(1.05g、0.06eq)、およびトルエン(toluene)400mlを、1口丸底フラスコ(1-1-neck-round bottom flask、1-neck-r.b.f)に入れて撹拌した。(4時間(h))
前記撹拌が終わった反応液を、濾過して固体を得た。(28g)前記固体をトルエン(toluene)を用いた保温濾過(hot filter)をして、N-[4-(4-ジベンゾフラニル)フェニル]-[1,1’-ビフェニル]-4-アミン(N-[4-(4-dibenzofuranyl)phenyl]-[1,1’-Biphenyl]-4-amine)を18g得た。(step yield=51%)
前記製造例1-cの合成法において、4-(4-ブロモフェニル)-ジベンゾフラン(4-(4-bromophenyl)-Dibenzofuran)を3-(4-ブロモフェニル)-ジベンゾフラン(3-(4-bromophenyl)-Dibenzofuran)に変更したことを除いてすべてを同様にして、N-[4-(3-ジベンゾフラニル)フェニル]-[1,1’-ビフェニル]-4-アミン(N-[4-(3-dibenzofuranyl)phenyl]-[1,1’-Biphenyl]-4-amine)を合成した。
前記製造例1-cの合成法において、4-(4-ブロモフェニル)-ジベンゾフラン(4-(4-bromophenyl)-Dibenzofuran)を2-(4-ブロモフェニル)-ジベンゾフラン(2-(4-bromophenyl)-Dibenzofuran)に変更したことを除いてすべてを同様にして、N-[4-(2-ジベンゾフラニル)フェニル]-[1,1’-ビフェニル]-4-アミン(N-[4-(2-dibenzofuranyl)phenyl]-[1,1’-Biphenyl]-4-amine)を合成した。
ジベンゾ[b,d]フラン-4-アミン(dibenzo[b,d]furan-4-amine)(13g、1eq)、3-ブロモビフェニル(3-bromobiphenyl)(25g、1.2eq)、Pd2(dba)3(2.4g、0.03eq)、t-BuONa(12.5g、1.5eq)、t-Bu3P(1.05g、0.06eq)、およびトルエン(toluene)400mlを、1口丸底フラスコ(1-1-neck-round bottom flask、1-neck-r.b.f)に入れて撹拌した。(3時間(h))
前記撹拌が終わった反応液を、メチレンクロライド(Methylene chloride、MC)およびヘキサン(Hexane、Hx)の比をMC:Hx=1:5としてカラム分離して、N-([1,1’-ビフェニル]-3-イル)ジベンゾ[b,d]フラン-4-アミン(N-([1,1’-biphenyl]-3-yl)dibenzo[b,d]furan-4-amine)を16g得た。(step yield=73%)
9,9-ジメチル-9H-フルオレン-2-アミン(9,9-dimethyl-9H-fluoren-2-amine)(10g、1eq)、4-(4-ブロモフェニル)ジベンゾ[b,d]フラン(4-(4-bromophenyl)dibenzo[b,d]furan(28g、1.2eq)、Pd2(dba)3(2.4g、0.03eq)、t-BuONa(12.5g、1.5eq)、t-Bu3P(1.05g、0.06eq)、およびトルエン(toluene)400mlを、1口丸底フラスコ(1-1-neck-round bottom flask、1-neck-r.b.f)に入れて撹拌した。(4時間(h))
9,9-ジメチル-9H-フルオレン-2-アミン(9,9-dimethyl-9H-fluoren-2-amine)(10g、1eq)、4-(4-ブロモフェニル)ジベンゾ[b,d]フラン(4-(4-bromophenyl)dibenzo[b,d]furan(28g、1.2eq)、Pd2(dba)3(2.4g、0.03eq)、t-BuONa(12.5g、1.5eq)、t-Bu3P(1.05g、0.06eq)、およびトルエン(toluene)400mlを、1口丸底フラスコ(1-1-neck-round bottom flask、1-neck-r.b.f)に入れて撹拌した。(4時間(h))
2-ブロモ-9H-カルバゾール(2-bromo-9H-carbazole)(7.5g、1eq)、ナフタレン-1-イルボロン酸(naphthalen-1-ylboronic acid)(8.2g、1.65eq)、Pd(Pph3)4(2g、0.05eq)、K2CO3(13g、3eq)、トルエン(toluene)150ml、EtOH50ml、およびH2O50mlを、1口丸底フラスコ(1-1-neck-round bottom flask、1-neck-r.b.f)に入れて撹拌した。(5時間(h))
前記撹拌が終わった反応液を、濾過して固体を得た。前記固体をMeOHで洗った後、2-(ナフタレン-1-イル)-9H-カルバゾール(2-(naphthalen-1-yl)-9H-carbazole)を8g得た。(step yield=89%)
前記製造例1-hの合成法において、ナフタレン-1-イルボロン酸(naphthalen-1-ylboronic acid)をジベンゾ[b,d]フラン-4-イルボロン酸(dibenzo[b,d]furan-4-ylboronic acid)に変更したことを除いてすべてを同様にして、2-(ジベンゾ[b,d]フラン-4-イル)-9H-カルバゾール(2-(dibenzo[b,d]furan-4-yl)-9H-carbazole)を合成した。(step yield=95%)
前記製造例1-hの合成法において、ナフタレン-1-イルボロン酸(naphthalen-1-ylboronic acid)をジベンゾ[b,d]チオフェン-4-イルボロン酸(dibenzo[b,d]thiophen-4-ylboronic acid)に変更したことを除いてすべてを同様にして、2-(ジベンゾ[b,d]チオフェン-4-イル)-9H-カルバゾール(2-(dibenzo[b,d]thiophen-4-yl)-9H-carbazole)を合成した。(step yield=85%)
中間体A(1)-P1(10g、1eq)、ビス(ビフェニル)アミン(bis(biphenyl)amine)(8g、1.1eq)、Pd(OAc)2(0.21g、0.05eq)、t-BuONa(2.62g、1.5eq)、t-Bu3P(0.37g、0.1eq)、およびtoluene200mlを、1口丸底フラスコ(1-1-neck-round bottom flask、1-neck-r.b.f)に入れて撹拌した。(1.5時間(h))
前記撹拌が終わった反応液を、濾過(filter)して固体を得た。(約11g、step yield=75%)前記固体をトルエン(toluene)を用いた保温濾過(hot filter)をして、HPLC99.96%の物質が6g得られた。
1,500Åの厚さにITOが薄膜コーティングされたガラス基板を、蒸留水超音波洗浄した。蒸留水洗浄が終わると、アセトン、メタノール、イソプロピルアルコールなどの溶剤で超音波洗浄をし乾燥させた後、UV洗浄機でUVを用いて5分間UVO処理した。以後、基板をプラズマ洗浄機(PT)に搬送させた後、真空状態でITOの仕事関数および残膜除去のためにプラズマ処理をして、有機蒸着用熱蒸着装置に搬送した。
前記実施例および比較例による有機発光素子の駆動電圧および寿命特性を評価した。具体的な測定方法は下記の通りであり、その結果は次の通りである。
製造された有機発光素子に対して、電圧を0Vから10Vまで上昇させながら、電流-電圧計(Keithley2400)を用いて単位素子に流れる電流値を測定し、測定された電流値を面積で割って結果を得た。
製造された有機発光素子に対して、電圧を0Vから10Vまで上昇させながら、輝度計(Minolta Cs-1000A)を用いて、その時の輝度を測定して結果を得た。
前記(1)および(2)から測定された輝度と電流密度および電圧を用いて同一の電流密度(10mA/cm2)の電流効率(cd/A)を計算した。
製造された有機発光素子に対して、ポラロニクス寿命測定システムを用いて、下記表11の実施例および比較例の素子を、初期輝度(cd/m2)を24000cd/m2で発光させ、時間経過による輝度の減少を測定して、初期輝度対比90%に輝度が減少した時点をT90寿命として測定した。
電流-電圧計(Keithley2400)を用いて、15mA/cm2における各素子の駆動電圧を測定して結果を得た。
前記表5を参照すれば、本発明に係る化合物は、比較例の化合物に比べて、駆動電圧が低下し、寿命および発光効率が向上したことを確認することができる。特に、カルバゾール基が2個以上置換されると、TSおよび蒸着温度が増加して寿命が減少し、高い駆動電圧および低い効率を有する。
200:陽極
300:有機物層
301:正孔注入層
302:正孔輸送層
303:発光層
304:正孔阻止層
305:電子輸送層
306:電子注入層
400:陰極
Claims (6)
- 下記化学式1で表される化合物:
前記化学式1において、
Ar1は、下記化学式2-5であり、
前記化学式2-5において、
R f ~R i は、それぞれ独立して、水素、非置換のC6~C60アリール基、または非置換のC2~C60ヘテロアリール基であり、
Ar2およびAr3は、それぞれ独立して、非置換のC6~C60アリール基、または下記化学式3-1~3-4のいずれか1つであり、
L1~L3は、それぞれ独立して、単結合、非置換のフェニレン基、または非置換のジメチルフルオレニレン基であり、
n1~n3は、互いに独立して、0~2の整数の1つであり、
R1~R6は、それぞれ独立して、水素であり、
前記化学式3-1~化学式3-4において、
Xは、-O-、-S-、または-CRxRy-であり、
RxおよびRyは、それぞれ独立して、水素、重水素、シアノ基、非置換のC1~C60アルキル基、またはC6~C60アリール基であるか、互いに融合して環を形成し、
Rb~Reは、それぞれ独立して、水素である。 - 陽極および陰極と、
前記陽極と前記陰極との間に位置する少なくとも1層の有機層とを含み、
前記有機層は、請求項1~3のいずれか1項に記載の化合物を含む有機光電子素子。 - 前記有機層は、正孔輸送層を含み、
前記正孔輸送層は、前記化合物を含む、請求項4に記載の有機光電子素子。 - 請求項4に記載の有機光電子素子を含む表示装置。
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