JP2020537826A - 有機発光素子 - Google Patents
有機発光素子 Download PDFInfo
- Publication number
- JP2020537826A JP2020537826A JP2020522029A JP2020522029A JP2020537826A JP 2020537826 A JP2020537826 A JP 2020537826A JP 2020522029 A JP2020522029 A JP 2020522029A JP 2020522029 A JP2020522029 A JP 2020522029A JP 2020537826 A JP2020537826 A JP 2020537826A
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- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- light emitting
- organic light
- Prior art date
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- Granted
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- 239000010410 layer Substances 0.000 claims description 106
- 239000000126 substance Substances 0.000 claims description 96
- 239000008199 coating composition Substances 0.000 claims description 78
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- 125000003118 aryl group Chemical group 0.000 claims description 45
- 238000002347 injection Methods 0.000 claims description 33
- 239000007924 injection Substances 0.000 claims description 33
- 239000012044 organic layer Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 17
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 13
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
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- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
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- 239000000243 solution Substances 0.000 description 10
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- 239000003999 initiator Substances 0.000 description 9
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- 125000004957 naphthylene group Chemical group 0.000 description 8
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- 239000002184 metal Substances 0.000 description 7
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- 238000002791 soaking Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
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- 239000010406 cathode material Substances 0.000 description 4
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 150000002739 metals Chemical group 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical group C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical group N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction 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
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-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
- 239000002356 single layer Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 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
- 229960002317 succinimide Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003462 sulfoxides Chemical class 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 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
- 238000010023 transfer printing Methods 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
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 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
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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Abstract
Description
第一に、有機発光素子で使用される物質は、熱的安定性に優れているものが好ましい。有機発光素子内では電荷の移動によるジュール熱(joule heat)が発生するからである。現在、正孔輸送層物質として主に使用されるNPB(n−propyl bromide)は、ガラス転移温度が100℃以下の値を有するので、高い電流を必要とする有機発光素子には使用しにくい問題がある。
第二に、低電圧駆動可能な高効率の有機発光素子を得るためには、有機発光素子内に注入された正孔または電子が円滑に発光層に伝達されると同時に、注入された正孔と電子が発光層の外に抜け出ないようにしなければならない。このために、有機発光素子に使用される物質は、適切なバンドギャップ(band gap)とHOMOまたはLUMOエネルギー準位を有しなければならない。現在、溶液塗布法によって製造される有機発光素子において、正孔輸送物質として使用されるPEDOT:PSS(Poly(3,4−ethylenedioxythiophene)doped with poly(styrenesulfonic acid))の場合、発光層物質として用いられる有機物のLUMOエネルギー準位に比べて、LUMOエネルギー準位が低いため、高効率、長寿命の有機発光素子の製造に困難がある。
Ar1およびAr2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、
R1〜R4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;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、
r1〜r3は、それぞれ1〜3であり、
r4は、1〜4であり、
前記r1〜r4がそれぞれ2以上の時、2以上のR1〜R4は、それぞれ互いに同一または異なり、
X1〜X3は、互いに同一または異なり、それぞれ独立に、下記構造式の中から選択され、
L4は、置換もしくは非置換のアルキレン基であり、
L5は、直接結合;または置換もしくは非置換のアリーレン基であり、
R5は、水素または置換もしくは非置換のアルキル基であり、
a1およびa2は、それぞれ0または1であり、
a2が0の時、前記L2は、置換もしくは非置換のアリール基であり、
a2が1の時、前記L2は、直接結合;または置換もしくは非置換のアリーレン基であり、
mは、1または2であり、mが2の場合、L1は、互いに同一または異なり、前記L1は、直接結合;または置換もしくは非置換のアリーレン基であり、
L3は、直接結合;または置換もしくは非置換のアルキレン基であり、
0≦a1+a2≦2であり、
R101〜R120のうちの少なくとも1つは、F;シアノ基;または置換もしくは非置換のフルオロアルキル基であり、
残りのR101〜R120のうちの少なくとも1つは、硬化基であり、
残りのR101〜R120は、互いに同一または異なり、それぞれ独立に、水素;重水素;ニトロ基;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ケニル基;置換もしくは非置換のアミン基;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。
L5は、直接結合;または置換もしくは非置換のアリーレン基であり;
R5は、水素または置換もしくは非置換のアルキル基である。
L1〜L3、Ar1、Ar2、R1〜R4、r1〜r4、X1〜X3、m、a1およびa2に関する定義は、前記化学式1で定義したものと同じである。
L11は、直接結合;−O−;−S−;置換もしくは非置換のアルキレン基;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、
kは、1または2であり、
前記kが2の場合、前記L11は、互いに同一または異なり、
R131は、置換もしくは非置換のアルキル基である。
R200は、水素;重水素;または置換もしくは非置換のアルキル基であり、
pは、0〜10の整数であり、
aは、1または2であり、bは、0または1であり、a+b=2であり、
X80〜X82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アルキル基;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ルキニル基;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、互いに隣接した基は、互いに結合して環を形成する。
R121〜R130は、互いに同一または異なり、それぞれ独立に、水素;重水素;ニトロ基;ハロゲン基;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ケニル基;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、硬化基である。
本明細書の一実施態様において、前記コーティング組成物またはその硬化物を含む有機物層は、発光層である。
他の実施態様において、前記コーティング組成物を用いて形成された有機物層は、印刷法によって形成される。
化合物1(3−ブロモ−9−フェニル−9H−カルバゾール)(9g、27.9mmol)と2((4−ホルミルフェニル)ボロン酸)(4.18g、27.9mmol)を無水テトラヒドロフラン(THF)(100mL)に溶かした後、Pd(PPh3)4(0.32g、0.28mmol)と2M炭酸カリウム(K2CO3/H20)水溶液70mlを入れて6時間還流させた。反応溶液を常温に冷やした後、有機層を抽出した。反応液を濃縮させ、エチルアルコール(EtOH)で再結晶して、3(8.9g、収率92%)を得た。
MS:[M+H]+=931
1H NMR:δ8.44(dd,J=14.7,1.8Hz,2H),7.78−7.10(m,42H),6.80(dd,J=17.6,10.9Hz,1H),6.69(dd,J=17.6,10.9Hz,1H),5.83(d,J=17.6Hz,1H),5.70(d,J=17.6Hz,1H),5.28(d,J=10.9Hz,1H),5.20(d,J=10.9Hz,1H).
MS:[M+H]+=959
1H NMR:δ8.44(dd,J=13.8,1.8Hz,2H),7.81−7.09(m,37H),6.95(s,2H),6.89(s,1H),6.80(dd,J=17.6,10.9Hz,1H),6.70(dd,J=17.7,10.9Hz,1H),5.83(d,J=17.6Hz,1H),5.72(d,J=17.6Hz,1H),5.28(d,J=10.9Hz,1H),5.21(d,J=10.9Hz,1H),2.16(s,3H),1.60(s,3H).
MS:[M+H]+=945
1H NMR:δ8.45(dd,J=7.7,1.8Hz,2H),7.80−7.16(m,37H),7.11(dd,J=8.2,2.0Hz,1H),6.99(d,J=7.9Hz,2H),6.80(dd,J=17.6,10.9Hz,1H),6.54(t,J=7.7Hz,3H),5.82(d,J=17.6Hz,1H),5.61(d,J=17.6Hz,1H),5.28(d,J=10.9Hz,1H),5.12(d,J=10.9Hz,1H),3.88(d,J=12.8Hz,1H),3.69(d,J=12.7Hz,1H).
MS:[M+H]+=971
1H NMR:δ8.44(dd,J=14.7,1.8Hz,2H),7.78−7.06(m,39H),6.85−6.78(m,2H),6.69(dd,J=17.6,10.9Hz,1H),5.86−5.81(m,2H),5.70(d,J=17.6Hz,1H),5.34(d,J=10.9Hz,1H),5.27(d,J=10.9Hz,1H),5.20(d,J=10.9Hz,1H).
コーティング組成物1は、化合物A 16mgと下記D1 4mgを8:2の重量比でトルエン(toluene)980mgに溶かして作った。
前記製造例1において、化合物Aの代わりに前記化合物Bを用いたことを除けば、同様にコーティング組成物を製造した。
前記製造例1において、化合物Aの代わりに前記化合物Cを用いたことを除けば、同様にコーティング組成物を製造した。
前記製造例1において、化合物Aの代わりに前記化合物Dを用いたことを除けば、同様にコーティング組成物を製造した。
前記製造例1において、化合物Aの代わりに下記の化合物Eを用いたことを除けば、同様にコーティング組成物を製造した。
前記製造例1において、化合物D1の代わりに下記の化合物D2を用いたことを除けば、同様にコーティング組成物を製造した。
前記製造例1において、化合物D1の代わりに下記の化合物D3を用いたことを除けば、同様にコーティング組成物を製造した。
前記製造例1において、化合物Aの代わりに下記の化合物Fを用いたことを除けば、同様にコーティング組成物を製造した。
前記製造例1において、化合物Aの代わりに下記の化合物Gを用いたことを除けば、同様にコーティング組成物を製造した。
前記製造例1において、化合物Aの代わりに下記のVNPBを用いたことを除けば、同様にコーティング組成物を製造した。
前記製造例10において、化合物D1の代わりに前記化合物D3を用いたことを除けば、同様にコーティング組成物を製造した。
実施例1.有機発光素子1の製造
ITO(indium tin oxide)が1500Åの厚さに薄膜蒸着されたガラス基板を、洗剤を溶かした蒸留水に入れて超音波洗浄した。ITOを30分間洗浄した後、蒸留水で2回繰り返し超音波洗浄を10分間進行させた。蒸留水洗浄が終わった後、イソプロピルアルコール、アセトンの溶剤で超音波洗浄をそれぞれ30分ずつ乾燥させた後、前記基板をグローブボックスに輸送した。
コーティング組成物1の代わりにコーティング組成物2を用いたことを除けば、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物3を用いたことを除けば、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物4を用いたことを除けば、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物5を用いたことを除けば、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物6を用いたことを除けば、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物7を用いたことを除けば、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物8を用いたことを除けば、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物9を用いたことを除けば、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物10を用いたことを除けば、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物11を用いたことを除けば、実施例1と同様の方法で有機発光素子を製造した。
201:アノード
301:正孔注入層
401:正孔輸送層
501:発光層
601:電子輸送層
701:カソード
Claims (12)
- 第1電極と、
前記第1電極に対向して備えられた第2電極と、
前記第1電極と前記第2電極との間に備えられた1層以上の有機物層とを含み、
前記有機物層のうちの1層以上は、下記化学式1で表される化合物;および化学式11で表される陰イオン基を含むイオン性化合物を含むコーティング組成物またはその硬化物を含むものである有機発光素子:
Ar1およびAr2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、
R1〜R4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;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、
r1〜r3は、それぞれ1〜3であり、
r4は、1〜4であり、
前記r1〜r4がそれぞれ2以上の時、2以上のR1〜R4は、それぞれ互いに同一または異なり、
X1〜X3は、互いに同一または異なり、それぞれ独立に、下記構造式の中から選択され、
L4は、置換もしくは非置換のアルキレン基であり、
L5は、直接結合;または置換もしくは非置換のアリーレン基であり、
R5は、水素または置換もしくは非置換のアルキル基であり、
a1およびa2は、それぞれ0または1であり、
a2が0の時、前記L2は、置換もしくは非置換のアリール基であり、
a2が1の時、前記L2は、直接結合;または置換もしくは非置換のアリーレン基であり、
mは、1または2であり、mが2の場合、L1は、互いに同一または異なり、前記L1は、直接結合;または置換もしくは非置換のアリーレン基であり、
L3は、直接結合;または置換もしくは非置換のアルキレン基であり、
0≦a1+a2≦2であり、
R101〜R120のうちの少なくとも1つは、F;シアノ基;または置換もしくは非置換のフルオロアルキル基であり、
残りのR101〜R120のうちの少なくとも1つは、硬化基であり、
残りのR101〜R120は、互いに同一または異なり、それぞれ独立に、水素;重水素;ニトロ基;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ケニル基;置換もしくは非置換のアミン基;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。 - 前記L1は、置換もしくは非置換のフェニレン基である、請求項1又は2に記載の有機発光素子。
- 前記Ar1およびAr2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フェニル基、または置換もしくは非置換のビフェニル基である、請求項1〜3のいずれか一項に記載の有機発光素子。
- 前記R103、R108、R113およびR118のうちの少なくとも1つは、硬化基である、請求項1〜5のいずれか一項に記載の有機発光素子。
- 前記イオン性化合物は、下記構造式の中から選択される陽イオン基を含むものである、請求項1〜8のいずれか一項に記載の有機発光素子:
R200は、水素;重水素;または置換もしくは非置換のアルキル基であり、
pは、0〜10の整数であり、
aは、1または2であり、bは、0または1であり、a+b=2であり、
X80〜X82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アルキル基;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ルキニル基;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、互いに隣接した基は、互いに結合して環を形成する。 - 前記コーティング組成物の硬化物は、前記コーティング組成物を熱処理または光処理によって硬化した状態である、請求項1〜9のいずれか一項に記載の有機発光素子。
- 前記コーティング組成物の硬化物を含む有機物層は、正孔輸送層、正孔注入層、または正孔輸送および正孔注入を同時に行う層である、請求項1〜10のいずれか一項に記載の有機発光素子。
- 前記コーティング組成物またはその硬化物を含む有機物層は、発光層である、請求項1〜10のいずれか一項に記載の有機発光素子。
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