KR102350367B1 - Electroluminescent materials based on carbazole and pyridine structural units - Google Patents
Electroluminescent materials based on carbazole and pyridine structural units Download PDFInfo
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- KR102350367B1 KR102350367B1 KR1020207011728A KR20207011728A KR102350367B1 KR 102350367 B1 KR102350367 B1 KR 102350367B1 KR 1020207011728 A KR1020207011728 A KR 1020207011728A KR 20207011728 A KR20207011728 A KR 20207011728A KR 102350367 B1 KR102350367 B1 KR 102350367B1
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- hydrogen
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- carbazole
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- phenyl
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- 239000000463 material Substances 0.000 title claims abstract description 30
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title claims abstract description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- 239000000470 constituent Substances 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- -1 tert-butyl (tert-butyl) Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000005215 recombination Methods 0.000 description 6
- 230000006798 recombination Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- MITGKKFYIJJQGL-UHFFFAOYSA-N 9-(4-chlorobenzoyl)-6-methylsulfonyl-2,3-dihydro-1H-carbazol-4-one Chemical compound ClC1=CC=C(C(=O)N2C3=CC=C(C=C3C=3C(CCCC2=3)=O)S(=O)(=O)C)C=C1 MITGKKFYIJJQGL-UHFFFAOYSA-N 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007666 vacuum forming Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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Abstract
본 발명은 카르바졸(carbazole) 및 피리딘(pyridine) 구성 유닛에 기초한 전계 발광 물질을 제공하며, 식 (I)의 구조를 가진다. 실험 결과는 상기 전계 발광 물질을 OLED에 사용하면 발광 효율이 우수하여 유기 전계 발광 소자의 분야에 활용될 가능성이 있음을 보여준다.
The present invention provides an electroluminescent material based on carbazole and pyridine structural units, and has the structure of formula (I). Experimental results show that when the electroluminescent material is used in an OLED, the luminous efficiency is excellent, and thus it is likely to be used in the field of organic electroluminescent devices.
Description
본 발명은 신규한 유기 발광 다이오드 전계 발광 물질에 관한 것으로, 더욱 상세하게는 카르바졸(carbazole) 및 피리딘(pyridine) 구성 유닛에 기초한 전계 발광 물질에 관한 것이고, 진공 증착으로 박막을 형성하며 유기 발광 다이오드 소자에 발광층 물질로 사용된다.The present invention relates to a novel organic light emitting diode electroluminescent material, and more particularly, to an electroluminescent material based on carbazole and pyridine constituent units, forming a thin film by vacuum deposition, and forming an organic light emitting diode It is used as a material for the light emitting layer in the device.
최근 활용 전망이 우수한 조명 및 디스플레이 기술로서 유기 발광 다이오드(OLED)가 학계와 산업계에서 널리 주목을 받고 있다. OLED 소자는 자체 발광, 광시야각, 짧은 반응시간 및 플렉시블 소자 제조 가능성 등의 특성을 가지고 있어 차세대 디스플레이 및 조명 기술 분야의 강력한 경쟁자이다. 그러나 현재 OLED는 여전히 낮은 효율 및 짧은 수명 등과 같은 문제점이 있으므로 이에 대한 추가적인 연구가 필요하다.Recently, as a lighting and display technology with excellent prospects for application, organic light emitting diodes (OLEDs) are receiving widespread attention in academia and industry. OLED devices have characteristics such as self-luminescence, wide viewing angles, short reaction times, and the possibility of manufacturing flexible devices, making them a strong competitor in the field of next-generation display and lighting technologies. However, current OLED still has problems such as low efficiency and short lifespan, so additional research is needed.
유기 발광 다이오드는 전자 발광 소자이며, 전압 구동 하에서 전자와 정공이 각각 전자수송층과 정공수송층을 통해 발광층으로 유입되어 재결합되며 엑시톤(exciton)을 형성한다. 그 후, 엑시톤은 발광 특성을 갖는 유기 분자로 에너지를 전달하여 여기시키고, 여기 상태 분자가 기저 상태로 돌아올 때 방사 전이가 일어나면서 발광한다. 1998년 Forrest 등이 전계 발광 인광 소자(PHOLED)를 보고한 이래, PHOLED는 삼중항 및 일중항 엑시톤 발광을 고효율로 사용하면서 많은 주목을 받았다. 고효율 PHOLED 소자는 통상적으로 다층 구조이며, 캐리어 주입, 전송 및 재결합 등의 과정을 편리하게 조절할 수 있는 이점이 있다. 발광층에서 게스트 물질의 도핑 농도가 높을 경우 농도 소광 및 T1-T1 소멸이 발생하여 발광 효율이 떨어질 수 있다. 이러한 문제를 해결하기 위하여, 통상적으로 게스트 물질을 호스트 물질에 도핑시켜 게스트 물질의 농도를 "희석"시킨다. 호스트에 형성된 엑시톤은 및 덱스터(Dexter) 에너지 전달 방식을 통해 게스트로 전달되며, 여기된 게스트 방사 발광은 기저 상태로 돌아온다. 따라서 고효율 PHOLED 소자를 얻기 위해서는 신규한 고성능의 호스트 물질을 개발하는 것이 중요하다.The organic light emitting diode is an electroluminescent device, and under voltage driving, electrons and holes flow into the light emitting layer through the electron transport layer and the hole transport layer, respectively, and recombine to form excitons. After that, excitons are excited by transferring energy to organic molecules having light-emitting properties, and when the excited-state molecules return to the ground state, radiative transition occurs and emits light. Since Forrest et al. reported electroluminescent phosphorescent devices (PHOLEDs) in 1998, PHOLEDs have attracted much attention due to their high efficiency use of triplet and singlet exciton emission. A high-efficiency PHOLED device typically has a multilayer structure, and has the advantage of conveniently controlling processes such as carrier injection, transport, and recombination. When the doping concentration of the guest material in the light emitting layer is high, concentration quenching and T 1 -T 1 annihilation may occur, so that luminous efficiency may decrease. To solve this problem, a guest material is typically doped into the host material to "dilute" the concentration of the guest material. Excitons formed on the host and Dexter energy transfer method to the guest, and the excited guest radiation emission returns to the ground state. Therefore, in order to obtain a high-efficiency PHOLED device, it is important to develop a novel high-performance host material.
호스트 물질은 정공형, 전자형 및 양극형의 세 가지 유형으로 나눌 수 있다. 정공형 호스트 물질을 사용하면 정공, 전자 재결합이 통상적으로 발광층과 전자수송층 계면에서 발생하고, 전자형 호스트 물질을 사용하면 정공, 전자 재결합이 통상적으로 발광층과 정공수송층 계면에서 발생한다. 여기에서 단극성 호스트 물질은 캐리어 재결합 영역을 좁게 만드는 경향이 있음을 알 수 있다. 좁은 재결합 영역은 국부적으로 엑시톤 밀도가 높아져 T1-T1 소멸을 가속화시키므로 소자 성능의 개선에 유익하지 않다. 반면 양극형 호스트 물질은 상기 문제를 효과적으로 해결할 수 있다. 양극형 호스트 물질을 사용하면 소자 내에서 정공과 전자의 균형을 맞추고, 캐리어 재결합 영역을 넓힐 뿐만 아니라 소자 구조를 단순화할 수 있기 때문에, 이 분야의 연구원들로부터 큰 관심을 받고 있다.Host materials can be divided into three types: hole type, electron type and bipolar type. When a hole-type host material is used, hole and electron recombination typically occurs at the interface between the light emitting layer and the electron transport layer, and when an electron type host material is used, hole and electron recombination typically occurs at the interface between the light emitting layer and the hole transport layer. Here, it can be seen that the unipolar host material tends to narrow the carrier recombination region. The narrow recombination region is not beneficial to the improvement of device performance because the local exciton density increases and accelerates T 1 -T 1 annihilation. On the other hand, the bipolar host material can effectively solve the above problem. The use of a bipolar host material is of great interest from researchers in this field because it can balance holes and electrons in the device, widen the carrier recombination region, and simplify the device structure.
본 발명의 목적은 피리딘(pyridine) 및 카르바졸(carbazole) 구성 유닛에 기초한 신규한 양극형 호스트 물질을 제공하는 것이며, 상기 물질은 유기 발광 다이오드 소자에 사용되어 우수한 발광 효율을 수득하였다.An object of the present invention is to provide a novel anode-type host material based on pyridine and carbazole constituent units, which is used in an organic light emitting diode device to obtain excellent luminous efficiency.
카르바졸 및 피리딘 구성 유닛에 기초한 전계 발광 물질은 화학식 (I)의 구조를 갖는다.An electroluminescent material based on carbazole and pyridine structural units has the structure of formula (I).
Ar은 하기 그룹 중의 하나이다.Ar is one of the following groups.
여기에서, R1 및 R2는 독립적으로 수소, C1-C4 치환 또는 미치환된 알킬(alkyl), C2-C4 치환 또는 미치환된 알케닐(alkenyl), C2-C4 치환 또는 미치환된 알키닐(alkynyl), C6-C10의 하나 이상의 치환기를 함유하는 치환 또는 미치환된 아릴(aryl), 방향족 탄화수소기, C3-C8의 하나 이상의 치환기를 함유하는 치환 또는 미치환된 하나 이상의 헤테로 원자를 함유하는 헤테로아릴(heteroaryl)로부터 선택되고; 상기 치환은 할로겐 원소, C1-C4의 알킬로 치환된다.Here, R 1 and R 2 are independently hydrogen, C1-C4 substituted or unsubstituted alkyl, C2-C4 substituted or unsubstituted alkenyl, C2-C4 substituted or unsubstituted alkynyl (alkynyl), a substituted or unsubstituted aryl containing one or more substituents of C6-C10, an aromatic hydrocarbon group, a substituted or unsubstituted heteroatom containing one or more substituents of C3-C8 containing one or more heteroatoms heteroaryl; The substitution is substituted with a halogen atom, C1-C4 alkyl.
바람직하게는, R1 및 R2는 독립적으로 수소, C1-C4 알킬, C6-C10의 하나 이상의 치환 또는 미치환된 아릴, 방향족 탄화수소기로부터 선택되고;Preferably, R 1 and R 2 are independently selected from hydrogen, C1-C4 alkyl, one or more substituted or unsubstituted C6-C10 aryl, aromatic hydrocarbon groups;
더욱 바람직하게는, R1 및 R2는 독립적으로 수소, 메틸(methyl), tert-부틸(tert-butyl), 페닐(phenyl), 톨릴(tolyl), 나프틸(naphthyl)로부터 선택되고;more preferably, R 1 and R 2 are independently selected from hydrogen, methyl, tert-butyl, phenyl, tolyl, naphthyl;
보다 바람직하게는, R1 및 R2는 수소, tert-부틸, 페닐 및 메틸로부터 선택된 동일한 치환기이고,More preferably, R 1 and R 2 are the same substituents selected from hydrogen, tert-butyl, phenyl and methyl,
특히 바람직하게는, 여기에서 Ar은 하기 그룹이고,Particularly preferably, wherein Ar is a group,
R1 및 R2는 수소, tert-부틸, 페닐로부터 선택된 동일한 치환기이다. R 1 and R 2 are identical substituents selected from hydrogen, tert-butyl, phenyl.
보다 바람직하게는, 여기에서 Ar은 하기 그룹 중 하나이다.More preferably, wherein Ar is one of the following groups.
특히 바람직하게는, R1은 수소이고, R2는 tert-부틸, 페닐, 톨릴, 나프틸이다.Particularly preferably, R 1 is hydrogen and R 2 is tert-butyl, phenyl, tolyl, naphthyl.
유기 전계 발광 다이오드 소자는 음극, 양극 및 유기층을 포함하고, 상기 유기층은 정공수송층, 발광층, 정공차단층 및 전자수송층 중 하나 이상이며, 이러한 유기층은 각층이 반드시 존재할 필요는 없다.The organic light emitting diode device includes a cathode, an anode and an organic layer, wherein the organic layer is at least one of a hole transport layer, a light emitting layer, a hole blocking layer and an electron transport layer, and each of these organic layers does not necessarily exist.
상기 정공수송층, 정공차단층, 발광층 및/또는 전자수송층은 식 (I)의 화합물을 포함한다.The hole transport layer, the hole blocking layer, the light emitting layer and / or the electron transport layer contains the compound of formula (I).
상기 식 (I)의 화합물은 발광층에 사용되는 호스트 물질이다.The compound of formula (I) is a host material used in the light emitting layer.
본 발명의 소자 유기층의 총 두께는 1 내지 1000nm이며, 바람직하게는 1 내지 500nm, 더욱 바람직하게는 5 내지 300nm이다.The total thickness of the device organic layer of the present invention is 1 to 1000 nm, preferably 1 to 500 nm, more preferably 5 to 300 nm.
상기 유기층은 증착 또는 용액법에 의해 박막을 형성할 수 있다.The organic layer may be formed into a thin film by vapor deposition or a solution method.
상기에서 언급한 바와 같이, 본 발명의 식 (I)의 화합물은 하기와 같지만 하기에 나열된 구조에 한정되지 않는다.As mentioned above, the compounds of formula (I) of the present invention are as follows, but are not limited to the structures listed below.
또한 바람직하게는 식 (I)로 표시되는 화합물의 구조는 하기와 같다.Preferably, the structure of the compound represented by the formula (I) is as follows.
상기 화합물은 유기 전계 발광 소자, 전계 발광 소자, 유기 전계 효과 트랜지스터, 유기 태양 전지 및 화학 센서에 사용된다.The compounds are used in organic electroluminescent devices, electroluminescent devices, organic field effect transistors, organic solar cells and chemical sensors.
실험 결과는 본 발명의 유기 호스트 물질을 OLED에 사용하면 발광 효율이 우수하여 유기 전계 발광 소자 분야에 활용될 가능성이 있음을 보여준다.Experimental results show that when the organic host material of the present invention is used for OLED, the luminous efficiency is excellent, and thus it is likely to be utilized in the field of organic electroluminescent devices.
도 1은 본 발명에 따른 유기 전계 발광 소자의 구조도이다.1 is a structural diagram of an organic electroluminescent device according to the present invention.
본 발명을 보다 상세하게 설명하기 위해, 이하의 예시를 특별히 나열하였으나 이에 한정되지 않는다.In order to explain the present invention in more detail, the following examples are specifically listed, but the present invention is not limited thereto.
실시예 1Example 1
화합물 1의 합성 경로Synthetic route of compound 1
화합물 1의 합성Synthesis of compound 1
질소 보호 하에서, 화합물 a(3.2g, 9.5mmol)(참고문헌: J. Heterocycl. Chem., 2016, 53, 615-619 합성), 화합물 1a(3.0g, 10.5mmol)(참고문헌: J. Mater. Chem. C, 2015, 3, 12529-12538), Pd(PPh3)4(208mg, 0.2mmol), 디옥산(dioxane)(40mL) 및 탄산칼륨 수용액(2M, 5mL)을 Schlenk관에 순차적으로 첨가한다. 80℃까지 가열하고 12시간 동안 반응시킨다. 실온으로 냉각시킨 후 상기 반응액을 물에 넣고, 디클로로메탄(dichloromethane)으로 3회 추출하여 유기상을 합친다. 유기층은 무수 황산나트륨으로 건조한 후, 용매를 제거하고, 잔여물은 칼럼 크로마토그래피로 분리하여 담황색 고체를 수득하였고(5.4g, 수율 85%), 승화 후 순도는 99.8%였다. MS(EI):m/z: 662.5(M+).Under nitrogen protection, compound a (3.2 g, 9.5 mmol) (reference: J. Heterocycl. Chem. , 2016, 53, 615-619 synthesis), compound la (3.0 g, 10.5 mmol) (reference: J. Mater) Chem. C, 2015, 3, 12529-12538), Pd(PPh 3 ) 4 (208mg, 0.2mmol), dioxane (40mL) and potassium carbonate aqueous solution (2M, 5mL) were sequentially placed in a Schlenk tube. add Heat to 80° C. and react for 12 hours. After cooling to room temperature, the reaction solution is added to water, extracted three times with dichloromethane, and the organic phases are combined. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed, and the residue was separated by column chromatography to obtain a pale yellow solid (5.4 g, yield 85%), and the purity was 99.8% after sublimation. MS (EI): m/z : 662.5 (M + ).
실시예 2Example 2
화합물 2의 합성 경로Synthetic route of compound 2
화합물 2의 합성Synthesis of compound 2
질소 보호 하에서, 화합물 a(2.2g, 6.5mmol), 화합물 2a(2.3g, 8.0mmol)(참고문헌: J. Mater. Chem. C, 2015, 3, 12529-12538 합성), Pd(PPh3)4(208mg, 0.2mmol), 디옥산(40mL) 및 탄산칼륨 수용액(2M, 5mL)을 Schlenk관에 순차적으로 첨가한다. 80℃까지 가열하고 12시간 동안 반응시킨다. 실온으로 냉각시킨 후 상기 반응액을 물에 넣고, 디클로로메탄으로 3회 추출하여 유기상을 합친다. 유기층은 무수 황산나트륨으로 건조한 후, 용매를 제거하고, 잔여물은 칼럼 크로마토그래피로 분리하여 담황색 고체를 수득하였고(3.1g, 수율 72%), 승화 후 순도는 99.8%였다. MS(EI):m/z: 662.5(M+).Under nitrogen protection, compound a (2.2 g, 6.5 mmol), compound 2a (2.3 g, 8.0 mmol) (reference: J. Mater. Chem. C, 2015, 3, 12529-12538 synthesis), Pd (PPh 3 ) 4 (208mg, 0.2mmol), dioxane (40mL) and potassium carbonate aqueous solution (2M, 5mL) are sequentially added to the Schlenk tube. Heat to 80° C. and react for 12 hours. After cooling to room temperature, the reaction solution is added to water, extracted three times with dichloromethane, and the organic phases are combined. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed, and the residue was separated by column chromatography to obtain a pale yellow solid (3.1 g, yield 72%), and the purity was 99.8% after sublimation. MS (EI): m/z : 662.5 (M + ).
실시예 3Example 3
화합물 3의 합성 경로Synthetic route of compound 3
화합물 3의 합성Synthesis of compound 3
질소 보호 하에서, 화합물 a(3.2g, 9.5mmol), 화합물 3a(3.0g, 10.5mmol)(참고문헌: J. Mater. Chem. C, 2015, 3, 12529-12538 합성), Pd(PPh3)4(208mg, 0.2mmol), 디옥산(40mL) 및 탄산칼륨 수용액(2M, 5mL)을 Schlenk관에 순차적으로 첨가한다. 80℃까지 가열하고 12시간 동안 반응시킨다. 실온으로 냉각시킨 후 상기 반응액을 물에 넣고, 디클로로메탄으로 3회 추출하여 유기상을 합친다. 유기층은 무수 황산나트륨으로 건조한 후, 용매를 제거하고, 잔여물은 칼럼 크로마토그래피로 분리하여 담황색 고체를 수득하였고(3.4g, 수율 54%), 승화 후 순도는 99.8%였다. MS(EI):m/z: 662.2(M+).Under nitrogen protection, compound a (3.2 g, 9.5 mmol), compound 3a (3.0 g, 10.5 mmol) (reference: J. Mater. Chem. C , 2015, 3, 12529-12538 synthesis), Pd (PPh 3 ) 4 (208mg, 0.2mmol), dioxane (40mL) and potassium carbonate aqueous solution (2M, 5mL) are sequentially added to the Schlenk tube. Heat to 80° C. and react for 12 hours. After cooling to room temperature, the reaction solution was added to water, extracted three times with dichloromethane, and the organic phases were combined. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed, and the residue was separated by column chromatography to obtain a pale yellow solid (3.4 g, yield 54%), and the purity was 99.8% after sublimation. MS (EI): m/z : 662.2 (M + ).
실시예4Example 4
화합물 12의 합성 경로Synthetic route of compound 12
화합물 12의 합성Synthesis of compound 12
질소 보호 하에서, 화합물 a(1.2g, 3.6mmol), 화합물 12a(1.1g, 3.83mmol)(참고문헌: CN105601613A 합성), Pd(PPh3)4(50mg, 0.04mmol), 디옥산(20mL) 및 탄산칼륨 수용액(2M, 5mL)을 Schlenk관에 순차적으로 첨가한다. 80℃까지 가열하고 12시간 동안 반응시킨다. 실온으로 냉각시킨 후 상기 반응액을 물에 넣고, 디클로로메탄으로 3회 추출하여 유기상을 합친다. 유기층은 무수 황산나트륨으로 건조한 후, 용매를 제거하고, 잔여물은 칼럼 크로마토그래피로 분리하여 담황색 고체를 수득하였고(2.4g, 수율 83%), 승화 후 순도는 99.7%였다. MS(EI):m /z: 814.5(M+).Under nitrogen protection, compound a (1.2 g, 3.6 mmol), compound 12a (1.1 g, 3.83 mmol) (reference: CN105601613A synthesis), Pd(PPh 3 ) 4 (50 mg, 0.04 mmol), dioxane (20 mL) and Aqueous potassium carbonate solution (2M, 5mL) is sequentially added to the Schlenk tube. Heat to 80° C. and react for 12 hours. After cooling to room temperature, the reaction solution was added to water, extracted three times with dichloromethane, and the organic phases were combined. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed, and the residue was separated by column chromatography to obtain a pale yellow solid (2.4 g, yield 83%), and the purity was 99.7% after sublimation. MS(EI): m /z : 814.5 (M + ).
실시예 5Example 5
유기 전계 발광 소자(1)의 제조Fabrication of the organic electroluminescent device (1)
본 발명의 유기 호스트 물질을 사용하여 OLED를 제조하며 도 1과 같다.An OLED is manufactured using the organic host material of the present invention, as shown in FIG. 1 .
먼저, 투명 전도성 ITO 유리 기판(10)(상표면에 양극(20)이 있음)을 순차적으로 세정제 용액, 탈이온수, 에탄올, 아세톤, 탈이온수로 세정한 후 다시 산소 플라즈마로 30초간 처리한다.First, the transparent conductive ITO glass substrate 10 (the
그 후, ITO 상에 10nm 두께의 HATCN을 정공주입층(30)으로 증착한다.Thereafter, HATCN having a thickness of 10 nm is deposited on the ITO as the
그 후, 화합물 TAPC를 증착시켜 40nm 두께의 정공수송층(40)을 형성한다.Thereafter, the compound TAPC is deposited to form the
그 후, 정공수송층 상에 30nm 두께의 AG-Pt-1(10%), TCTA(60%) 및 화합물 1(30%)을 발광층(50)으로 증착한다.Thereafter, AG-Pt-1 (10%), TCTA (60%) and Compound 1 (30%) having a thickness of 30 nm are deposited on the hole transport layer as the
그 후, 발광층 상에 50nm 두께의 TmPyPb를 정공차단층(60)으로 증착한다.Thereafter, TmPyPb having a thickness of 50 nm is deposited on the emission layer as the
마지막으로, 1nm LiF를 전자주입층(70)으로, 100nm Al을 소자 음극(80)으로 증착한다.Finally, 1 nm LiF is deposited as the
소자 중 상기 구조식Structural formula of the element
제조된 소자는 20mA/cm2의 작동 전류 밀도 하에서 9060cd/m2의 밝기, 45.3cd/A의 전류 효율로 녹색광을 방출한다. 본 발명의 유기 물질로 제조된 소자는 전계 발광 성능이 우수하여 고성능 OLED 소자의 호스트 물질의 요건을 충족시킨다. The fabricated device emits green light with a brightness of 9060 cd/m 2 and a current efficiency of 45.3 cd/A under an operating current density of 20 mA/cm 2 . The device made of the organic material of the present invention has excellent electroluminescence performance to satisfy the requirements of a host material for a high-performance OLED device.
10: 유리 기판
20: 양극
30: 정공주입층
40: 정공수송층
50: 발광층
60: 정공차단층
70: 전자주입층
80: 음극10: glass substrate
20: positive electrode
30: hole injection layer
40: hole transport layer
50: light emitting layer
60: hole blocking layer
70: electron injection layer
80: cathode
Claims (10)
화학식 (I)의 구조를 갖고,
Ar은 하기 그룹 중의 하나이고,
여기에서, R1 및 R2는 독립적으로 수소, C1-C4 치환 또는 미치환된 알킬(alkyl), C6-C10의 하나 이상의 치환기를 함유하는 치환 또는 미치환된 아릴(aryl)로부터 선택되고; 상기 치환은 할로겐 원소 또는 C1-C4의 알킬로 치환되는 것을 특징으로 하는 카르바졸 및 피리딘 구성 유닛에 기초한 전계 발광 물질.An electroluminescent material based on carbazole and pyridine structural units, comprising:
has the structure of formula (I),
Ar is one of the following groups,
wherein R 1 and R 2 are independently selected from hydrogen, C1-C4 substituted or unsubstituted alkyl, C6-C10 substituted or unsubstituted aryl containing one or more substituents; An electroluminescent material based on carbazole and pyridine constituent units, characterized in that the substitution is substituted with a halogen element or C1-C4 alkyl.
여기에서, R1 및 R2는 독립적으로 수소, C1-C4 알킬, C6-C10의 하나 이상의 치환 또는 미치환된 아릴로부터 선택되고; 상기 치환은 할로겐 원소 또는 C1-C4의 알킬로 치환되는 것을 특징으로 하는 전계 발광 물질.According to claim 1,
wherein R 1 and R 2 are independently selected from hydrogen, C1-C4 alkyl, one or more substituted or unsubstituted C6-C10 aryl; The substitution is an electroluminescent material, characterized in that substituted with a halogen element or C1-C4 alkyl.
여기에서, R1 및 R2는 독립적으로 수소, 메틸(methyl), tert-부틸(tert-butyl), 페닐(phenyl), 톨릴(tolyl), 나프틸(naphthyl)로부터 선택되는 것을 특징으로 하는 전계 발광 물질.3. The method of claim 2,
Here, R 1 and R 2 are independently selected from hydrogen, methyl (methyl), tert-butyl (tert-butyl), phenyl (phenyl), tolyl (tolyl), naphthyl (naphthyl) luminescent material.
여기에서, R1 및 R2는 수소, tert-부틸, 페닐 및 메틸로부터 선택된 동일한 치환기인 것을 특징으로 하는 전계 발광 물질.4. The method of claim 3,
wherein R 1 and R 2 are the same substituent selected from hydrogen, tert-butyl, phenyl and methyl.
여기에서, Ar은 하기 그룹이고
,
여기에서, R1 및 R2는 수소, tert-부틸, 페닐로부터 선택된 동일한 치환기인 것을 특징으로 하는 전계 발광 물질.5. The method of claim 4,
Here, Ar is the group
,
wherein R 1 and R 2 are the same substituents selected from hydrogen, tert-butyl, and phenyl.
여기에서 Ar은 하기 그룹 중 하나인 것을 특징으로 하는 전계 발광 물질.
3. The method of claim 2,
wherein Ar is one of the following groups.
R1은 수소이고, R2는 페닐, 톨릴, 나프틸인 것을 특징으로 하는 전계 발광 물질.7. The method of claim 6,
R 1 is hydrogen, and R 2 is phenyl, tolyl, or naphthyl.
상기 식 (I)의 구조는 하기 화합물 중의 하나인 것을 특징으로 하는 전계 발광 물질.
3. The method of claim 2,
The structure of formula (I) is an electroluminescent material, characterized in that one of the following compounds.
상기 식 (I)의 구조가 하기 화합물인 것을 특징으로 하는 전계 발광 물질.
9. The method of claim 8,
An electroluminescent material, characterized in that the structure of the formula (I) is the following compound.
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