KR102069310B1 - Novel hetero-cyclic compound and organic light emitting device comprising the same - Google Patents
Novel hetero-cyclic compound and organic light emitting device comprising the same Download PDFInfo
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- KR102069310B1 KR102069310B1 KR1020170081230A KR20170081230A KR102069310B1 KR 102069310 B1 KR102069310 B1 KR 102069310B1 KR 1020170081230 A KR1020170081230 A KR 1020170081230A KR 20170081230 A KR20170081230 A KR 20170081230A KR 102069310 B1 KR102069310 B1 KR 102069310B1
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- compound
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- light emitting
- unsubstituted
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 3
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- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
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- 125000003710 aryl alkyl group Chemical group 0.000 description 3
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- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
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- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
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- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 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
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-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
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 150000002964 pentacenes Chemical class 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
- 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
- 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
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 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
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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 group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 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
- 125000000168 pyrrolyl 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
- 238000007363 ring formation reaction Methods 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
- 229910052710 silicon Inorganic materials 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
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent 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
- 239000007921 spray Substances 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010345 tape casting Methods 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
- 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
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 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
- 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
- 150000003852 triazoles Chemical class 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-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
- 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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation 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
- 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-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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- C07—ORGANIC CHEMISTRY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Abstract
본 발명은 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자를 제공한다. The present invention provides a novel heterocyclic compound and an organic light emitting device using the same.
Description
본 발명은 신규한 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각, 우수한 콘트라스트, 빠른 응답 시간을 가지며, 휘도, 구동 전압 및 응답 속도 특성이 우수하여 많은 연구가 진행되고 있다. In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have been conducted.
유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. The organic layer is often formed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.
상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다.There is a continuous demand for the development of new materials for organic materials used in such organic light emitting devices.
본 발명은 신규한 헤테로고리 화합물 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to a novel heterocyclic compound compound and an organic light emitting device comprising the same.
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:The present invention provides a compound represented by Formula 1:
[화학식 1][Formula 1]
상기 화학식 1에서, In Chemical Formula 1,
X는 각각 독립적으로 N, 또는 CH이고, 단 X 중 적어도 하나는 N이고, Each X is independently N or CH, provided that at least one of X is N,
Y는 O, 또는 S이고, Y is O, or S,
L1은 결합; 페닐렌; 또는
L2은 결합; 페닐렌; 또는
Ar1은 수소; 중수소; 할로겐; 시아노; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C2-60 알케닐; 치환 또는 비치환된 C2-60 알키닐; 치환 또는 비치환된 C3-30 사이클로알킬; 치환 또는 비치환된 C6-60 아릴; 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴; 치환 또는 비치환된 트리(C1-60 알킬)실릴; 치환 또는 비치환된 트리(C6-60 아릴)실릴; 치환 또는 비치환된 디(C1-60 알킬)(C6-60 아릴)실릴; 치환 또는 비치환된 (C1-60 알킬)디(C6-60 아릴)실릴; 치환 또는 비치환된 모노- 또는 디-(C1-60 알킬)아미노; 또는 치환 또는 비치환된 모노- 또는 디-(C6-60 아릴)아미노이고, Ar 1 is hydrogen; heavy hydrogen; halogen; Cyano; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 2-60 alkynyl; Substituted or unsubstituted C 3-30 cycloalkyl; Substituted or unsubstituted C 6-60 aryl; C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Substituted or unsubstituted tri (C 1-60 alkyl) silyl; Substituted or unsubstituted tri (C 6-60 aryl) silyl; Substituted or unsubstituted di (C 1-60 alkyl) (C 6-60 aryl) silyl; Substituted or unsubstituted (C 1-60 alkyl) di (C 6-60 aryl) silyl; Substituted or unsubstituted mono- or di- (Ci- 60 alkyl) amino; Or substituted or unsubstituted mono- or di- (C 6-60 aryl) amino,
Ar2는 치환 또는 비치환된 C6-60 아릴; 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고, Ar 2 is substituted or unsubstituted C 6-60 aryl; C 2-60 heteroaryl containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S,
k는 0, 또는 1이고, k is 0, or 1,
단, L1 및 L2 중 적어도 하나는
또한, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다.In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. do.
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물 층의 재료로서 사용될 수 있으며, 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. 특히, 상술한 화학식 1로 표시되는 화합물은 정공주입, 정공수송, 정공주입 및 수송, 발광, 전자수송, 또는 전자주입 재료로 사용될 수 있다.The compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode. In particular, the compound represented by Chemical Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.FIG. 1 shows an example of an organic light emitting element composed of a
2 shows an example of an organic light emitting element consisting of a
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail to aid in understanding the present invention.
본 발명은 상기 화학식 1로 표시되는 화합물을 제공한다. The present invention provides a compound represented by Chemical Formula 1.
본 명세서에서,
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups including one or more of N, O, and S atoms, or two or more substituents connected to the substituents exemplified above. . For example, "a substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and can be interpreted as a substituent to which two phenyl groups are linked.
본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.Although carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the ester group may be substituted with oxygen of the ester group having 1 to 25 carbon atoms, a straight chain, branched chain or cyclic alkyl group or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention is not limited thereto.
본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group and the like.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 사이클로펜틸메틸,사이클로헥틸메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.
본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸, 3-메틸사이클로펜틸, 2,3-디메틸사이클로펜틸, 사이클로헥실, 3-메틸사이클로헥실, 4-메틸사이클로헥실, 2,3-디메틸사이클로헥실, 3,4,5-트리메틸사이클로헥실, 4-tert-부틸사이클로헥실, 사이클로헵틸, 사이클로옥틸 등이 있으나, 이에 한정되지 않는다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우,
본 명세서에 있어서, 헤테로고리기는 이종 원소로 O, N, Si 및 S 중 1개 이상을 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as a dissimilar element, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group (phenanthroline), thiazolyl group, Isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서, 아르알킬기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above. In the present specification, the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, except that the arylene is a divalent group, the description of the aryl group described above may be applied. In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding. In the present specification, the heterocyclic group is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding.
바람직하게는, 상기 화학식 1은 하기 화학식 1-1, 1-2, 또는 1-3으로 표시된다:Preferably,
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
바람직하게는, Ar1은 페닐, 또는 비페닐릴이다. Preferably, Ar 1 is phenyl or biphenylyl.
바람직하게는, Ar2는 페닐이다. Preferably, Ar 2 is phenyl.
상기 화학식 1로 표시되는 화합물의 대표적인 예는 다음과 같다:Representative examples of the compound represented by
한편, 상기 화학식 1로 표시되는 화합물 중 L1이 결합이 아닌 화합물은 일례로 하기 반응식 1과 같은 제조 방법으로 제조할 수 있다. Meanwhile, among the compounds represented by
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상기 단계 1-1 내지 1-4는, 아민 치환 반응 또는 스즈키 커플링 반응으로서, 각각 팔라듐 촉매와 염기 존재하에 수행하는 것이 바람직하며, 스즈키 커플링 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하다. 상기 단계 1-5는 고리화 반응으로서 포타슘카보네이트 존재 하에 반응시킬 수 있다. Steps 1-1 to 1-4 are amine substitution reactions or Suzuki coupling reactions, and are preferably carried out in the presence of a palladium catalyst and a base, respectively, and the reactor for the Suzuki coupling reaction is changed as known in the art. It is possible. Steps 1-5 may be reacted in the presence of potassium carbonate as a cyclization reaction.
또한, 상기 화학식 1로 표시되는 화합물 중 L1이 결합인 화합물은 상기 반응식 1의 단계 1-1 및 1-2를 생략하여 제조할 수 있다. In addition, among the compounds represented by
상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다.The manufacturing method may be more specific in the production examples to be described later.
또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 일례로, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다. In another aspect, the present invention provides an organic light emitting device comprising a compound represented by the formula (1). In one embodiment, the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by
본 발명의 유기 발광 소자의 유기물 층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물 층으로서 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present invention may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
또한, 상기 유기물 층은 정공주입층, 정공수송층, 또는 정공 주입과 수송을 동시에 하는 층을 포함할 수 있고, 상기 정공주입층, 정공수송층, 또는 정공 주입과 수송을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다. The organic layer may include a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes, and the hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting a hole may be represented by
또한, 상기 유기물 층은 발광층을 포함할 수 있고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함한다. In addition, the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by
또한, 상기 유기물 층은 전자수송층, 또는 전자주입층을 포함할 수 있고, 상기 전자수송층, 또는 전자주입층은 상기 화학식 1로 표시되는 화합물을 포함한다. In addition, the organic layer may include an electron transport layer, or an electron injection layer, the electron transport layer, or the electron injection layer comprises a compound represented by the formula (1).
또한, 상기 전자수송층, 전자주입층, 또는 전자수송 및 전자주입을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다. In addition, the electron transport layer, the electron injection layer, or a layer for the electron transport and electron injection at the same time includes a compound represented by the formula (1).
또한, 상기 유기물 층은 발광층 및 전자수송층을 포함하고, 상기 전자수송층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. In addition, the organic layer may include a light emitting layer and an electron transport layer, the electron transport layer may include a compound represented by the formula (1).
또한, 본 발명에 따른 유기 발광 소자는, 기판 상에 양극, 1층 이상의 유기물 층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. 또한, 본 발명에 따른 유기 발광 소자는 기판 상에 음극, 1층 이상의 유기물 층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다. 예컨대, 본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다.In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting diode according to the present invention may be an organic light emitting diode having an inverted type structure in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 있다. FIG. 1 shows an example of an organic light emitting element composed of a
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공주입층, 정공수송층, 발광층 및 전자수송층 중 1층 이상에 포함될 수 있다. 2 shows an example of an organic light emitting element consisting of a
본 발명에 따른 유기 발광 소자는, 상기 유기물 층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. 또한, 상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by
예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시켜 제조할 수 있다. 이때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. In addition, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then a material that may be used as a cathode may be deposited thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물 층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.In addition, the compound represented by
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다(WO 2003/012890). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material (WO 2003/012890). However, the manufacturing method is not limited thereto.
일례로, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이거나, 또는 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다.In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode, the second electrode is an anode.
상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SNO2:Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. As the anode material, a material having a large work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SNO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
상기 정공주입층은 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물 층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone)계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정 되는 것은 아니다. The hole injection layer is a layer for injecting holes from the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, and perylene-based Organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer is a layer for receiving holes from the hole injection layer and transporting holes to the light emitting layer. A hole transporting material is a material capable of transporting holes from an anode or a hole injection layer and transferring them to the light emitting layer. This is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다. The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다. The light emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a hetero ring-containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서, 아릴아미노기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되지 않는다.Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted. At least one arylvinyl group is substituted with the above-described arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
상기 전자수송층은 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄 층 또는 실버층이 뒤따른다.The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transporting material, a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자 주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron injection layer is a layer for injecting electrons from an electrode, has a capability of transporting electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, etc. It is not limited to this.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.In addition, the compound represented by
상기 화학식 1로 표시되는 화합물 및 이를 포함하는 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.Preparation of the compound represented by
제조예Production Example
제조예Production Example 1: 화합물 A의 제조 1: Preparation of Compound A
단계 1) 화합물 A-1의 제조Step 1) Preparation of Compound A-1
4-클로로-3-플루오로벤조산(22 g, 126 mmol)을 티오닐 클로라이드(200 mL)에 투입한 후, 2시간 동안 환류 및 교반하였다. 상온으로 냉각 후, 증류하여 생성된 고체를 디에틸 에테르로 세척한 후 건조하여 화합물 A-1(22.1 g, 수율 91%)을 제조하였다. 4-Chloro-3-fluorobenzoic acid (22 g, 126 mmol) was added to thionyl chloride (200 mL), and then refluxed and stirred for 2 hours. After cooling to room temperature, the solid produced by distillation was washed with diethyl ether and dried to prepare Compound A-1 (22.1 g, 91% yield).
단계 2) 화합물 A-2의 제조Step 2) Preparation of Compound A-2
디메틸아민 2.0 M 용액(74.8 mL, 150 mmol) 및 트리에틸아민(37.9 mL, 272 mmol)을 디에틸에테르 500 mL에 투입한 후, 화합물 A-1(27 g, 140 mmol)을 천천히 적가한 후 30분 동안 교반하였다. 생성된 고체를 여과한 후, 여액을 증류하여 화합물 A-2(23.4 g, 수율 83%)를 제조하였다. Dimethylamine 2.0 M solution (74.8 mL, 150 mmol) and triethylamine (37.9 mL, 272 mmol) were added to 500 mL of diethyl ether, and then Compound A-1 (27 g, 140 mmol) was slowly added dropwise. Stir for 30 minutes. After the resulting solid was filtered, the filtrate was distilled to prepare compound A-2 (23.4 g, 83% yield).
단계 3) 화합물 A의 제조Step 3) Preparation of Compound A
N'-시아노벤즈이미드아미드(16.8 g, 114 mmol) 및 화합물 A-2(23 g, 114 mmol) 및 포스포러스 옥시클로라이드(12 mL, 128 mmol)을 아세토니트릴 500 mL에 투입한 후 1시간 동안 교반 및 환류하였다. 상온으로 식힌 후 생성된 고체를 여과하고, 물과 에탄올로 세척 후 건조하여 화합물 A(29.2 g, 수율 80%)를 제조하였다. N'-cyanobenzimidamide (16.8 g, 114 mmol) and Compound A-2 (23 g, 114 mmol) and phosphorus oxychloride (12 mL, 128 mmol) were added to 500 mL of acetonitrile for 1 hour. Stirred and refluxed. After cooling to room temperature, the resulting solid was filtered, washed with water and ethanol and dried to prepare Compound A (29.2 g, yield 80%).
제조예Production Example 2: 화합물 B의 제조 2: Preparation of Compound B
4-클로로-3-플루오로벤조산 대신 3-클로로-2-플루오로벤조산(25 g, 143 mmol)을 사용하는 것을 제외하고, 제조예 1과 동일한 방법으로 화합물 B(26.0 g, 3 step 수율 57%)을 제조하였다. Compound B (26.0 g, 3 step yield 57) in the same manner as in Preparation Example 1, except that 3-chloro-2-fluorobenzoic acid (25 g, 143 mmol) was used instead of 4-chloro-3-fluorobenzoic acid %) Was prepared.
제조예Production Example 3: 화합물 C의 제조 3: Preparation of Compound C
4-클로로-3-플루오로벤조산 대신 2-클로로-3-플루오로벤조산(35 g, 200 mmol)을 사용하는 것을 제외하고, 제조예 1과 동일한 방법으로 화합물 C(20.0 g, 3 step 수율 52%)을 제조하였다. Compound C (20.0 g, 3 step yield 52) in the same manner as in Production Example 1, except that 2-chloro-3-fluorobenzoic acid (35 g, 200 mmol) was used instead of 4-chloro-3-fluorobenzoic acid. %) Was prepared.
실시예Example 1 One
단계 1) 화합물 1-1의 제조Step 1) Preparation of Compound 1-1
3-브로모-5-클로로-1,1'-비페닐(20 g, 75 mmol)과 11-페닐-11,12-디하이드로인돌로[2,3-a]카바졸(26 g, 75 mmol)을 톨루엔 100 mL에 분산시키고, 나트륨 터셔리-부톡사이드(14.4 g, 150 mmol)를 투입하여 가온하였다. 환류 하에 비스(트리-터셔리-부틸포스핀)팔라듐(0.38 g, 1 mol%)을 투입하여 6시간 동안 반응시켰다. 반응 종결 후 상온으로 온도를 낮추고, 생성된 고체를 여과하였다. 여과된 고체를 클로로포름에 다시 녹이고 무수황산마그네슘을 넣고 교반한 후 여과하여 감압 증류하였다. 클로로포름과 에틸아세테이트를 이용하여 재결정하여 화합물 1-1(31.4g, 수율 81%)을 제조하였다. 3-bromo-5-chloro-1,1'-biphenyl (20 g, 75 mmol) and 11-phenyl-11,12-dihydroindolo [2,3-a] carbazole (26 g, 75 mmol) was dispersed in 100 mL of toluene, and sodium tertiary-butoxide (14.4 g, 150 mmol) was added thereto to warm. Under reflux, bis (tri-tertiary-butylphosphine) palladium (0.38 g, 1 mol%) was added thereto and reacted for 6 hours. After completion of the reaction, the temperature was lowered to room temperature, and the resulting solid was filtered. The filtered solid was dissolved in chloroform again, anhydrous magnesium sulfate was added thereto, stirred, and filtered and distilled under reduced pressure. Compound 1-1 (31.4 g, 81% yield) was prepared by recrystallization using chloroform and ethyl acetate.
단계 2) 화합물 1-2의 제조Step 2) Preparation of Compound 1-2
화합물 1-1(20 g, 39 mmol), 비스(피나콜라토)디보론(비스(피나콜라토)디보론)(13.2 g, 46.3 mmol), 포타슘아세테이트(7.6 g, 77 mmol)를 1,4-다이옥산 150 mL에 투입하고, 환류 및 교반 상태에서 디벤질리덴아세톤팔라듐(0.7 g, 3 mol%)과 트리시클로헥실포스핀(0.7 g, 6 mol%)을 첨가하고 12시간 동안 환류 및 교반시켰다. 반응이 종결되면 혼합물을 실온으로 냉각하고, 셀라이트를 통해 여과하였다. 여액을 감압 하에 농축한 후 잔류물에 클로로포름을 넣고 녹인 후 물로 세척하여 유기층을 분리한 후 무수황산 마그네슘으로 건조하였다. 이를 감압 증류하고, 에틸아세테이트와 에탄올로 교반하여 화합물 1-2(16.5 g, 수율 70 %)를 제조하였다.Compound 1-1 (20 g, 39 mmol), bis (pinacolato) diboron (bis (pinacolato) diboron) (13.2 g, 46.3 mmol), potassium acetate (7.6 g, 77 mmol) was added 1, To 150 mL of 4-dioxane, dibenzylideneacetone palladium (0.7 g, 3 mol%) and tricyclohexylphosphine (0.7 g, 6 mol%) were added under reflux and stirring, followed by reflux and stirring for 12 hours. I was. At the end of the reaction the mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated under reduced pressure, chloroform was added to the residue, dissolved, washed with water to separate the organic layer, and dried over anhydrous magnesium sulfate. This was distilled under reduced pressure, and stirred with ethyl acetate and ethanol to prepare compound 1-2 (16.5 g, yield 70%).
단계 3) 화합물 1-3의 제조Step 3) Preparation of Compound 1-3
화합물 1-2(20 g, 33 mmol)와 화합물 A(10.5 g, 33 mmol)을 테트라히드로퓨란 110 mL에 분산시키고, 탄산 칼륨(9.0 g, 66 mmol)을 물 30 mL에 녹여서 혼합물에 투입하였다. 질소 충전 후, 테트라키스(트리페닐포스핀)팔라듐(0.4 g, 1 mol%)을 상기 현탁액에 가하였다. 질소 하에서, 혼합물을 환류에서 6시간 동안 교반하였다. 실온으로 냉각 후 생성된 고체를 여과하였다. 여과된 고체를 클로로포름에 녹인 후 물로 2회 세척하고 유기층을 분리하여 무수황산마그네슘으로 건조하고, 감압 농축하여 얻은 화합물에 에틸아세테이트를 투입하여 슬러리하는 방법으로 정제하여 화합물 1-3(20.3 g, 수율 81 %)를 제조하였다. Compound 1-2 (20 g, 33 mmol) and Compound A (10.5 g, 33 mmol) were dispersed in 110 mL of tetrahydrofuran, and potassium carbonate (9.0 g, 66 mmol) was dissolved in 30 mL of water and added to the mixture. . After nitrogen filling, tetrakis (triphenylphosphine) palladium (0.4 g, 1 mol%) was added to the suspension. Under nitrogen, the mixture was stirred at reflux for 6 hours. After cooling to room temperature the resulting solid was filtered. The filtered solid was dissolved in chloroform, washed twice with water, the organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure, ethyl acetate was added to the resulting compound, which was purified by slurry. Compound 1-3 (20.3 g, yield) 81%) was prepared.
단계 4) 화합물 1-4의 제조Step 4) Preparation of Compound 1-4
화합물 1-3(20 g, 26 mmol)와 (2-하이드록시페닐)보로닉 애시드(4.0 g, 29 mmol)를 1,4-다이옥산(90 mL)에 분산시키고, 포타슘포스페이트(11.0 g, 52 mmol)와 물(30 mL)을 추가로 투입하였다. 환류 및 교반 상태에서 디벤질리덴아세톤팔라듐(0.5 g, 3 mol%)과 트리시클로헥실포스핀(0.5 g, 6 mol%)을 첨가하고 12시간 동안 환류 및 교반시켰다. 반응이 종결되면 혼합물을 실온으로 냉각하여 물층을 분리하고, 감압 하에 농축한 후 잔류물에 클로로포름을 넣고 녹인 후 물로 세척하여 유기층을 분리한다. 분리한 유기층에 무수황산마그네슘으로 건조하여 여과하였다. 감압 농축하여 얻은 화합물에 에탄올과 에틸아세테이트를 투입하여 슬러리하고 고체를 여과하여 화합물 1-4(16.1 g, 수율 75 %)를 제조하였다.Compound 1-3 (20 g, 26 mmol) and (2-hydroxyphenyl) boronic acid (4.0 g, 29 mmol) were dispersed in 1,4-dioxane (90 mL) and potassium phosphate (11.0 g, 52 mmol) and water (30 mL) were further added. Dibenzylideneacetone palladium (0.5 g, 3 mol%) and tricyclohexylphosphine (0.5 g, 6 mol%) were added under reflux and stirring, and the mixture was refluxed and stirred for 12 hours. After the reaction is completed, the mixture is cooled to room temperature, the water layer is separated, concentrated under reduced pressure, chloroform is added to the residue, dissolved and washed with water to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and filtered. Ethanol and ethyl acetate were added to the obtained compound, which was concentrated under reduced pressure, and the slurry was filtered. Solids were filtered to prepare compound 1-4 (16.1 g, yield 75%).
단계 5) 화합물 1의 제조Step 5) Preparation of
화합물 1-4(23 g, 28 mmol)을 다이메틸로픔아마이드 100 mL에 넣고 교반하였다. 이후 포타슘카보네이트(7.6 g, 55 mmol)를 투입한 후 환류하였다. 2시간 후 상온으로 온도를 낮추고 여과하였다. 여과액을 과량의 물에 투입하여 고체를 석출시키고, 이를 여과하였다. 여과된 고체를 다시 클로로포름에 녹인 후 물로 2회 세척하고 분리하였다. 모아진 유기층을 황산마그네슘을 이용해 건조하였다. 환류 하에 클로로포름을 제거하면서 에틸아세테이트를 투입하여 재결정하는 방법으로 화합물 1(16.1 g, 수율 72 %)을 제조하였다.Compound 1-4 (23 g, 28 mmol) was added to 100 mL of dimethyllotamide and stirred. Then potassium carbonate (7.6 g, 55 mmol) was added and refluxed. After 2 hours, the temperature was lowered to room temperature and filtered. The filtrate was poured into excess water to precipitate a solid, which was filtered off. The filtered solid was dissolved in chloroform again, washed twice with water and separated. The combined organic layers were dried over magnesium sulfate. Compound 1 (16.1 g, yield 72%) was prepared by recrystallization by adding ethyl acetate while removing chloroform under reflux.
MS:[M+H]+=806MS: [M + H] + = 806
실시예Example 2 2
단계 1) 화합물 2-1의 제조Step 1) Preparation of Compound 2-1
11-페닐-11,12-디하이드로인돌로[2,3-a]카바졸(20 g, 60 mmol)과 1-브로모-3-클로로벤젠(11.5 g, 60 mmol)을 사용하여, 실시예 1의 단계 1과 동일한 방법으로 화합물 2-1(19.5 g, 수율 73%)을 제조하였다. 11-phenyl-11,12-dihydroindolo [2,3-a] carbazole (20 g, 60 mmol) and 1-bromo-3-chlorobenzene (11.5 g, 60 mmol) Compound 2-1 (19.5 g, yield 73%) was prepared in the same manner as
단계 2) 화합물 2-2의 제조Step 2) Preparation of Compound 2-2
화합물 2-1(19 g, 43 mmol)을 사용하여, 실시예 1의 단계 2와 동일한 방법으로 화합물 2-2(17.4 g, 수율 76%)를 제조하였다. Using Compound 2-1 (19 g, 43 mmol), Compound 2-2 (17.4 g, yield 76%) was prepared in the same manner as
단계 3) 화합물 2-3의 제조Step 3) Preparation of Compound 2-3
화합물 B(20 g, 62.5 mmol)와 화합물 2-2(35 g, 66 mmol)를 사용하여, 실시예 1의 단계 3과 동일한 방법으로 화합물 2-3(35.0 g, 수율 81%)을 제조하였다. Using Compound B (20 g, 62.5 mmol) and Compound 2-2 (35 g, 66 mmol), Compound 2-3 (35.0 g, 81% yield) was prepared in the same manner as
단계 4) 화합물 2-4의 제조Step 4) Preparation of Compound 2-4
화합물 2-3(20 g, 29 mmol)과 3-(4,4,5,5-테트라메틸-1,3,2-디옥사보롤란-2-일)비페닐-4-올(9.6 g, 32.3 mmol)를 사용하여, 실시예 1의 단계 4와 동일한 방법으로 화합물 2-4(18.6 g, 수율 77%)를 제조하였다. Compound 2-3 (20 g, 29 mmol) and 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) biphenyl-4-ol (9.6 g , 32.3 mmol) was used to prepare Compound 2-4 (18.6 g, yield 77%) in the same manner as in
단계 5) 화합물 2의 제조Step 5) Preparation of
화합물 2-4(20 g, 24 mmol)를 사용하여, 실시예 1의 단계 5와 동일한 방법으로 화합물 2(13.2 g, 수율 68 %)를 제조하였다.Using Compound 2-4 (20 g, 24 mmol), Compound 2 (13.2 g, yield 68%) was prepared in the same manner as
MS:[M+H]+=806MS: [M + H] + = 806
실시예Example 3 3
단계 1) 화합물 3-2의 제조Step 1) Preparation of Compound 3-2
11-페닐-11,12-디하이드로인돌로[2,3-a]카바졸(20 g, 60 mmol)과 화합물 3-1(19.3 g, 60 mmol)을 사용하여, 실시예 1의 단계 1과 동일한 방법으로 화합물 3-2(30.4 g, 수율 82%)를 제조하였다.
단계 2) 화합물 3-3의 제조Step 2) Preparation of Compound 3-3
화합물 3-2(20 g, 33 mmol)와 3-(4,4,5,5-테트라메틸-1,3,2-디옥사보롤란-2-일)비페닐-4-올 (10.6 g, 36 mmol)를 사용하여, 실시예 1의 단계 4와 동일한 방법으로 화합물 3-3(17.4 g, 수율76%)을 제조하였다.Compound 3-2 (20 g, 33 mmol) and 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) biphenyl-4-ol (10.6 g , 36 mmol) was used to prepare Compound 3-3 (17.4 g, yield 76%) in the same manner as in
단계 3) 화합물 3의 제조Step 3) Preparation of
화합물 3-3(20 g, 27 mmol)을 사용하여, 실시예 1의 단계 5와 동일한 방법으로 화합물 3(12.7 g, 수율 65 %)을 제조하였다.Using compound 3-3 (20 g, 27 mmol), compound 3 (12.7 g, yield 65%) was prepared in the same manner as in
MS:[M+H]+=730MS: [M + H] + = 730
실험예Experimental Example 1 One
ITO(indium tin oxide)가 1,300 Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀리포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,300
상기와 같이 준비된 ITO 투명 전극 위에 하기 화학식 HI-1 화합물을 50Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 상에 하기 화학식 NPB 화합물을 650Å의 두께로 열 진공 증착하여 정공수송층을 형성하고, 상기 정공수송층 상에 하기 화학식 HT-2 화합물을 150Å 두께로 진공 증착하여 전자저지층을 형성하였다. 이어서, 상기 전자저지층 상에 실시예 1의 화합물 및 하기 화학식 YGD 화합물을 90:10의 중량비로 250Å 두께로 공증착하여 발광층을 형성하였다. 상기 발광층 상에 하기 화학식 ET-1 호합물을 450Å의 두께로 진공 증착하여 전자수송층을 형성하고, 상기 전자수송층 상에 LiF를 15Å 증착하여 전자주입층을 형성하였다. 상기 전자주입층 상에 1000Å 두께로 알루미늄을 증착하여 음극을 형성하였다. On the ITO transparent electrode prepared as above, the chemical formula HI-1 was vacuum deposited to a thickness of 50 kPa to form a hole injection layer. The hole injection layer was thermally vacuum deposited to a thickness of 650 kPa on the hole injection layer to form a hole transport layer, and the electron HT layer was formed by vacuum evaporation of the following chemical formula HT-2 compound on the hole transport layer to 150 kW thick. Subsequently, the light emitting layer was formed by co-depositing the compound of Example 1 and the following chemical formula YGD compound in a weight ratio of 90:10 on the electronic blocking layer to a thickness of 250 Pa. An electron transport layer was formed by vacuum depositing a compound of formula ET-1 on the light emitting layer to a thickness of 450 Å, and depositing 15 Å of LiF on the electron transport layer to form an electron injection layer. Aluminum was deposited to a thickness of 1000 Å on the electron injection layer to form a cathode.
상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.7 Å/sec를 유지하였고, 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 1×10-7 ~ 5×10-8 torr를 유지하였다.In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å / sec, the aluminum was maintained at the deposition rate of 2 Å / sec, the vacuum during deposition was maintained at 1 × 10 -7 ~ 5 × 10 -8 torr It was.
실험예Experimental Example 2 및 3 2 and 3
실시예 1의 화합물 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고, 실험예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound shown in Table 1 instead of the compound of Example 1.
비교 compare 실험예Experimental Example 1 및 2 1 and 2
실시예 1의 화합물 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고, 실험예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서, 화합물 a 및 b는 각각 하기와 같다. An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound shown in Table 1 instead of the compound of Example 1. In Table 1 below, compounds a and b are as follows, respectively.
상기 실험예 및 비교 실험예에서 제조한 유기 발광 소자에 전류를 인가하여, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 1 에 나타내었다. 이때, T95은 전류 밀도 20 mA/cm2에서의 초기 휘도를 100%로 하였을 때 휘도가 95%로 감소되는데 소요되는 시간을 의미한다.By applying a current to the organic light emitting device manufactured in the Experimental Example and Comparative Experimental Example, the voltage, efficiency, color coordinates and lifetime were measured and the results are shown in Table 1 below. In this case, T95 means the time required for the luminance to decrease to 95% when the initial luminance at the current density of 20 mA / cm 2 is 100%.
(@10 mA/cm2)Voltage (V)
(@ 10 mA / cm 2 )
(@10 mA/cm2)Efficiency (Cd / A)
(@ 10 mA / cm 2 )
(x,y)Color coordinates
(x, y)
(@20 mA/cm2)Life (T95, hr)
(@ 20 mA / cm 2 )
1: 기판 2: 양극
3: 발광층 4: 음극
5: 정공주입층 6: 정공수송층
7: 발광층 8: 전자수송층1: substrate 2: anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: light emitting layer 8: electron transport layer
Claims (6)
[화학식 1]
상기 화학식 1에서,
X는 모두 N이고,
Y는 O, 또는 S이고,
L1은 결합; 페닐렌; 또는
L2은 결합; 페닐렌; 또는
Ar1은 수소; 중수소; 할로겐; 시아노; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C2-60 알케닐; 치환 또는 비치환된 C2-60 알키닐; 치환 또는 비치환된 C3-30 사이클로알킬; 치환 또는 비치환된 C6-60 아릴; 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴; 치환 또는 비치환된 트리(C1-60 알킬)실릴; 치환 또는 비치환된 트리(C6-60 아릴)실릴; 치환 또는 비치환된 디(C1-60 알킬)(C6-60 아릴)실릴; 치환 또는 비치환된 (C1-60 알킬)디(C6-60 아릴)실릴; 치환 또는 비치환된 모노- 또는 디-(C1-60 알킬)아미노; 또는 치환 또는 비치환된 모노- 또는 디-(C6-60 아릴)아미노이고,
Ar2는 치환 또는 비치환된 C6-60 아릴; 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고,
k는 0, 또는 1이고,
단, L1 및 L2 중 적어도 하나는
Compound represented by the following formula (1):
[Formula 1]
In Chemical Formula 1,
X is all N,
Y is O, or S,
L 1 is a bond; Phenylene; or
L 2 is a bond; Phenylene; or
Ar 1 is hydrogen; heavy hydrogen; halogen; Cyano; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 2-60 alkynyl; Substituted or unsubstituted C 3-30 cycloalkyl; Substituted or unsubstituted C 6-60 aryl; C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Substituted or unsubstituted tri (C 1-60 alkyl) silyl; Substituted or unsubstituted tri (C 6-60 aryl) silyl; Substituted or unsubstituted di (C 1-60 alkyl) (C 6-60 aryl) silyl; Substituted or unsubstituted (C 1-60 alkyl) di (C 6-60 aryl) silyl; Substituted or unsubstituted mono- or di- (Ci- 60 alkyl) amino; Or substituted or unsubstituted mono- or di- (C 6-60 aryl) amino,
Ar 2 is substituted or unsubstituted C 6-60 aryl; C 2-60 heteroaryl containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S,
k is 0, or 1,
Provided that at least one of L 1 and L 2
상기 화학식 1은, 하기 화학식 1-1, 1-2, 또는 1-3으로 표시되는,
화합물:
[화학식 1-1]
[화학식 1-2]
[화학식 1-3]
The method of claim 1,
Formula 1 is represented by the following formula 1-1, 1-2, or 1-3,
compound:
[Formula 1-1]
[Formula 1-2]
[Formula 1-3]
Ar1은 페닐, 또는 비페닐릴인,
화합물.
The method of claim 1,
Ar 1 is phenyl, or biphenylyl,
compound.
Ar2는 페닐인,
화합물.
The method of claim 1,
Ar 2 is phenyl
compound.
화합물:
The compound represented by Formula 1 is any one selected from the group consisting of
compound:
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