KR20170103565A - Novel compound and organic electroluminescent device comprising the same - Google Patents
Novel compound and organic electroluminescent device comprising the same Download PDFInfo
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- KR20170103565A KR20170103565A KR1020160026651A KR20160026651A KR20170103565A KR 20170103565 A KR20170103565 A KR 20170103565A KR 1020160026651 A KR1020160026651 A KR 1020160026651A KR 20160026651 A KR20160026651 A KR 20160026651A KR 20170103565 A KR20170103565 A KR 20170103565A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 50
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
- 125000002560 nitrile group Chemical group 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 125000003277 amino group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
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- 238000000034 method Methods 0.000 claims description 35
- 230000000903 blocking effect Effects 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
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- 238000006243 chemical reaction Methods 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
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- 239000011521 glass Substances 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
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- 238000004519 manufacturing process Methods 0.000 description 2
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- 239000000203 mixture Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 150000005041 phenanthrolines Chemical class 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 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 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- YMRHXVOHLPIMNN-UHFFFAOYSA-N 1-n-(3-methylphenyl)-2-n,2-n-diphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 YMRHXVOHLPIMNN-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-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
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- AXAIFPYIOUBISR-UHFFFAOYSA-N Cc1c(C)c(-c2cccc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c2)c(C)c(C)c1-c1cccc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c1 Chemical compound Cc1c(C)c(-c2cccc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c2)c(C)c(C)c1-c1cccc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c1 AXAIFPYIOUBISR-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- H01L51/0035—
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- H01L51/0067—
-
- H01L51/5012—
-
- H01L51/5072—
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- H01L51/5096—
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Spectroscopy & Molecular Physics (AREA)
Abstract
Description
본 발명은 신규 화합물 및 이를 포함하는 유기발광소자에 관한 것이다.The present invention relates to a novel compound and an organic light emitting device comprising the same.
최근, 자체 발광형으로 저전압 구동이 가능한 유기발광소자는, 평판표시소자의 주류인 액정디스플레이(LCD, liquid crystal display)에 비해, 시야각, 대조비 등이 우수하고 백라이트가 불필요하여 경량 및 박형이 가능하며 소비전력 측면에서도 유리하고 색 재현 범위가 넓어, 차세대 표시소자로서 주목을 받고 있다.In recent years, an organic light emitting device capable of being driven by a low voltage in a self-luminous mode has a better viewing angle and contrast ratio than a liquid crystal display (LCD), which is a mainstream of a flat panel display device, It has been attracting attention as a next generation display device because it is advantageous in terms of power consumption and has a wide color reproduction range.
유기발광다이오드에서 유기물 층으로 사용되는 재료는 크게 기능에 따라, 발광층 재료, 정공주입층 재료, 정공수송층 재료, 전자수송층 재료, 전자주입층 재료 등으로 분류될 수 있다. 그리고 상기 발광 재료는 분자량에 따라 고분자와 단분자로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료, 전자의 삼중항 여기상태로부터 유래되는 인광 재료와 삼중항 여기상태로부터 일중항 여기상태로 전자의 이동이 유래 되는 지연형광 재료로 분류될 수 있으며, 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도판트 계를 사용할 수 있다. 그 원리는 호스트보다 에너지 대역 간극이 작고 발광물질인 도판트를 발광층에 소량 혼합하면, 호스트에서 생성된 엑시톤이 도판트로 전이되어 빛을 내는 것이다. 이러한 원리를 이용하여 도판트와 호스트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다. Materials used as an organic material layer in an organic light emitting diode can be largely classified into a light emitting layer material, a hole injecting layer material, a hole transporting layer material, an electron transporting layer material, and an electron injection layer material according to functions. The light emitting material may be classified into a polymer and a single molecule according to molecular weight, and may be classified into a fluorescent material derived from singlet excited state of electrons according to a light emitting mechanism, a phosphorescent material derived from a triplet excited state of electrons, Emitting materials derived from the movement of electrons to the singlet excitation state, and the light-emitting material is classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary for realizing better color according to the luminescent color . Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material. The principle is that when the energy band gap is smaller than that of the host and a small amount of dopant is mixed into the light emitting layer, the excitons generated by the host are transferred to the dopant to emit light. Using this principle, light of a desired wavelength can be obtained depending on the type of the dopant and the host.
현재까지 이러한 유기발광소자에 사용되는 물질로서 다양한 화합물들이 알려져 있으나, 이제까지 알려진 물질을 이용한 유기발광소자의 경우 높은 구동전압, 낮은 효율 및 짧은 수명으로 인해 실용화하는 데에 많은 어려움이 있었다. 따라서, 우수한 특성을 갖는 물질을 이용하여 저전압 구동, 고휘도 및 장수명을 갖는 유기발광소자를 개발하려는 노력이 지속되어 왔다. Various compounds have been known as materials used in such organic light emitting devices. However, organic light emitting devices using known materials have been difficult to put to practical use due to high driving voltage, low efficiency, and short lifetime. Accordingly, efforts have been made to develop an organic light emitting device having low voltage driving, high luminance, and long life using a material having excellent characteristics.
본 발명은 분자의 강직성을 높여주어 열안정성이 높고, 장수명 특성이 우수하며, 고효율 및 고색순도를 갖는 신규 화합물 및 이를 포함하는 유기발광소자를 제공하는 것을 목적으로 한다.It is an object of the present invention to provide a novel compound having a high thermal stability and an excellent long-life property by increasing the rigidity of a molecule, a high efficiency and a high color purity, and an organic light emitting device containing the same.
또한, 전자수송층 재료 또는 정공저지층 재료로 유용한 신규 화합물을 제공하는 것을 목적으로 한다.It is also an object of the present invention to provide a novel compound useful as an electron transporting layer material or a hole blocking layer material.
상기의 목적을 달성하기 위한 수단으로서, As means for achieving the above object,
본 발명은 하기 화학식 1로 표현되는 화합물을 제공한다. The present invention provides a compound represented by the following general formula (1).
<화학식 1>≪ Formula 1 >
(상기 화학식 1에서 n은 각각 독립적으로 0 내지 2의 정수이며, (Wherein n is independently an integer of 0 to 2,
X는 각각 독립적으로 C, CR1, 또는 N 이며, 여기서 R1은 수소, 할로겐, 아미노기, 니트릴기, 또는 니트로기이거나 치환되거나 치환되지 않은 C6 ~ C50 의 아릴기 또는 치환되거나 치환되지 않은 C2 ~ C50의 헤테로아릴기이고,X is independently C, CR 1 , or N, wherein R 1 is a hydrogen, a halogen, an amino group, a nitrile group, a nitro group, a substituted or unsubstituted C 6 -C 50 aryl group or a substituted or unsubstituted A C 2 to C 50 heteroaryl group,
A 및 B는 각각 독립적으로 치환되거나 치환되지 않은 C6 ~ C50 의 아릴기 또는 치환되거나 치환되지 않은 C2 ~ C50의 헤테로아릴기이다)A and B are each independently a substituted or unsubstituted C 6 ~ C 50 aryl group or a substituted or a non-C 2 ~ C 50 heteroaryl group is optionally substituted)
본 발명은 또한, 상기 화합물을 포함하는 것을 특징으로 하는 유기발광소자를 제공한다.The present invention also provides an organic light emitting device comprising the above compound.
본 발명에 따른 화합물은 듀렌 구조 특성상 4개의 메틸기의 입체장애 효과로 인해 광학에너지(일중항 및 삼중항 에너지)가 감소하는 것을 막아주고, 분자의 강직성을 높여주어 열안정성을 향상시켜 장수명 특성이 우수하다. 또한, 우수한 전자 끌개 효과는 전자 주입 효과 증가를 이끌 수 있으며 낮은 HOMO 에너지준위는 정공 저지 특성을 증가시켜주므로 소자에서의 고효율 및 고색순도의 특성을 가질 수 있다. 따라서, 전자수송층 재료, 또는 정공저지층 재료로 특히 유용하고, 청색, 녹색, 적색뿐만 아니라 진청색 발광소자에도 우수하게 적용 가능하다.The compound according to the present invention prevents the decrease of optical energy (singlet and triplet energy) due to the effect of steric hindrance of four methyl groups due to the duren structure structure, improves the rigidity of the molecule, improves thermal stability, Do. In addition, the excellent electron attracting effect can lead to an increase in the electron injection effect, and the low HOMO energy level increases the hole blocking property, so that the device can have high efficiency and high color purity characteristics. Therefore, it is particularly useful as an electron transporting layer material or a hole blocking layer material, and is applicable not only to blue, green, and red but also to a deep blue light emitting device.
도 1은 본 발명의 실시예에 따른 유기발광소자의 구성 개략 단면도이다. 1 is a schematic cross-sectional view of a configuration of an organic light emitting diode according to an embodiment of the present invention.
이하에서 본 발명을 상세히 설명한다. Hereinafter, the present invention will be described in detail.
본 발명에 따른 화합물은 하기 화학식 1로 표현되는 것을 특징으로 한다. The compound according to the present invention is represented by the following general formula (1).
<화학식 1>≪ Formula 1 >
여기서, n은 각각 독립적으로 0 내지 2의 정수이며, Here, n is independently an integer of 0 to 2,
X는 각각 독립적으로 C, CR1, 또는 N 이며, 여기서 R1은 수소, 할로겐, 아미노기, 니트릴기, 아릴포스핀옥사이드기, 또는 니트로기이거나 치환되거나 치환되지 않은 C6 ~ C50 의 아릴기 또는 치환되거나 치환되지 않은 C2 ~ C50의 헤테로아릴기이고,X is independently C, CR 1 , or N, wherein R 1 is a hydrogen, a halogen, an amino group, a nitrile group, an arylphosphine oxide group, or a nitro group or a substituted or unsubstituted C 6 -C 50 aryl group Or a substituted or unsubstituted C 2 to C 50 heteroaryl group,
A 및 B는 각각 독립적으로 치환되거나 치환되지 않은 C6 ~ C50 의 아릴기 또는 치환되거나 치환되지 않은 C2 ~ C50의 헤테로아릴기이다.A and B are each a substituted or unsubstituted C 6 ~ C 50 aryl group or independently a substituted or unsubstituted C 2 ~ C 50 heteroaryl group.
상기에서 치환되는 경우에 구체적인 치환기로는 할로겐, 아미노기, 니트릴기, 아릴포스핀옥사이드기, 니트로기, C1 ~ C10의 알킬기, C1 ~ C10의 알콕시기 등을 들 수 있다. Specific examples of the substituent in the above substitution include a halogen, an amino group, a nitrile group, an arylphosphine oxide group, a nitro group, a C 1 to C 10 alkyl group, and a C 1 to C 10 alkoxy group.
더 구체적으로는, 상기 A, B 중 적어도 하나 이상은 하기 화학식 2로 표현되는 것 중에 선택되는 것이 좋다.More specifically, it is preferable that at least one of A and B is selected from among those represented by the following formula (2).
<화학식 2>(2)
여기서, Y는 각각 독립적으로 CR6, 또는 N 이며, R6는 수소, 할로겐, 아미노기, 니트릴기, 아릴포스핀옥사이드기, 또는 니트로기이거나 치환되거나 치환되지 않은 C6 ~ C50 의 아릴기 또는 치환되거나 치환되지 않은 C2 ~ C50의 헤테로아릴기이고, R3 및 R4는 각각 독립적으로 수소, 아릴포스핀옥사이드기 또는 니트릴기이며, R5는 수소, 치환되거나 치환되지 않은 C6 ~ C50 의 아릴기 또는 치환되거나 치환되지 않은 C2 ~ C50의 헤테로아릴기이다. Wherein Y is independently CR 6 or N and R 6 is hydrogen, halogen, an amino group, a nitrile group, an arylphosphine oxide group, a nitro group, a substituted or unsubstituted C 6 -C 50 aryl group, or a substituted or a non-C 2 ~ heteroaryl group of C 50 unsubstituted, R 3 and R 4 are each independently hydrogen, aryl phosphine oxide group or a nitrile group, R 5 is hydrogen, substituted or unsubstituted C 6 ~ It is C 50 aryl group, or an optionally substituted a C 2 ~ C 50 heteroaryl group.
구체적으로는 Y 중 적어도 하나에는 N이 포함되는 것이 좋다. 또한 R3, R4, 및 R6 중 적어도 하나에는 니트릴기 또는 아릴포스핀옥사이드기가 포함되는 것이 좋다. 이는 전자당김 효과로 인하여 발광영역이 확대되어 소자 수명의 안정성을 제공할 수 있기 때문이다.Specifically, it is preferable that at least one of Y includes N. It is also preferred that at least one of R 3 , R 4 , and R 6 contains a nitrile group or an arylphosphine oxide group. This is because the luminescent region is enlarged due to the electron withdrawing effect to provide stability of the device lifetime.
더 나아가, 놀랍게도 후술하는 실시예에서 보듯이, A 및 B 중 적어도 하나 이상이 듀렌기와의 관계에서 파라 결합을 이루는 것보다 메타 결합을 이루는 것이 효율이 현저히 우수한 것을 확인하였다.Furthermore, it has been surprisingly found that at least one of A and B, as shown in the examples described later, is much more efficient in forming a meta bond than forming a para bond in relation to the duren group.
상기 메타 결합이란 하기 화학식 3으로 표현되는 화합물 중 하나를 의미한다.The meta bond means one of the compounds represented by the following general formula (3).
<화학식 3>(3)
여기서, A, B, X, n의 정의는 상기 화학식 1과 동일하며, m은 0 또는 1이다.Here, A, B, X and n have the same definitions as in the above formula (1), and m is 0 or 1.
본 발명에 따른 화합물은 듀렌 구조 특성상 4개의 메틸기의 입체장애 효과로 인해 광학에너지(일중항 및 삼중항 에너지)가 감소하는 것을 막아주고, 분자의 강직성을 높여주어 열안정성도 향상될 수 있어 장수명 특성이 우수하다. 또한, 우수한 전자끌개효과 및 낮은 HOMO 레벨로 고효율 및 고색순도를 가질 수 있으며, 전자 주입 효과로 인하여 전자수송층 재료, 또는 정공저지층 재료로 특히 유용하다(전자수송층 재료 또는 정공저지층 재료로 사용하는 경우에는 상기 화학식 1의 A, B에 정공수송 특성을 갖는 카바졸기 등이 존재하는 것은 바람직하지 않다). The compound according to the present invention prevents the decrease of the optical energy (singlet and triplet energy) due to the steric hindrance effect of the four methyl groups due to the characteristics of the duren structure, increases the rigidity of the molecule and improves the thermal stability, Is excellent. In addition, it can have high efficiency and high color purity with a high electron withdrawing effect and a low HOMO level, and is particularly useful as an electron transporting layer material or a hole blocking layer material due to an electron injection effect (used as an electron transporting layer material or a hole blocking layer material It is not preferable that a carbazole group or the like having a hole transporting property exists in A and B in the above formula (1)).
아래의 화합물들은 본 발명에 따른 화합물의 구체적인 예들이다. 하기의 예들은 본 발명을 설명하기 위한 예시일 뿐이므로, 본 발명이 이에 한정되는 것은 아니다. The following compounds are specific examples of the compounds according to the present invention. The following examples are only illustrative of the present invention, and the present invention is not limited thereto.
이하에서는 본 발명에 따른 유기 발광 소자를 설명한다. Hereinafter, an organic light emitting device according to the present invention will be described.
본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기발광소자를 제공한다. 구체적으로는 상기 화학식 1로 표시되는 화합물은 전자수송층 물질 또는 정공저지층 물질로 유기발광소자에 포함된다.The present invention provides an organic electroluminescent device comprising the compound represented by the above formula (1). Specifically, the compound represented by Formula 1 is included in an organic light emitting device as an electron transporting layer material or a hole blocking layer material.
상기 유기발광소자는 애노드(anode, 10)와 캐소드(cathode, 16) 사이에 정공주입층(HIL, 11), 정공수송층(HTL, 12), 발광층(EML, 13), 전자수송층(ETL, 14), 전자주입층(EIL, 15) 등의 유기물층을 1 개 이상 포함할 수 있다. 선택적으로, 상기 발광층(EML, 13)과 전자수송층(ETL, 14) 사이에 정공저지층(HBL, 도시 생략됨)이, 정공수송층(HTL, 12)과 발광층(EML, 13) 사이에 전자저지층(EBL, 도시 생략됨)이 더 포함될 수 있다.The organic light emitting device includes a hole injection layer (HIL) 11, a hole transport layer (HTL) 12, an emission layer (EML) 13, and an electron transport layer (ETL) 14 between an
먼저, 기판 상부에 높은 일함수를 갖는 애노드 전극용 물질을 증착시켜 애노드를 형성한다. 이때, 상기 기판은 통상의 유기발광소자에서 사용되는 기판을 사용할 수 있으며, 특히 기계적 강도, 열적 안정성, 투명성, 표면평활성, 취급용이성, 및 방수성이 우수한 유리 기판 또는 투명 플라스틱 기판을 사용하는 것이 좋다. 또한, 애노드 전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등을 사용할 수 있다. 상기 애노드 전극용 물질은 통상의 애노드 형성방법에 의해 증착할 수 있으며, 구체적으로 증착법 또는 스퍼터링법에 의해 증착할 수 있다.First, an anode electrode material having a high work function is deposited on the substrate to form an anode. At this time, the substrate can be a substrate used in conventional organic light emitting devices, and it is particularly preferable to use a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity can be used. The anode electrode material can be deposited by a conventional anode formation method, and specifically, it can be deposited by a deposition method or a sputtering method.
그 다음, 상기 애노드 전극 상부에 정공주입층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB(Langmuir-Blodgett)법 등과 같은 방법에 의해 형성할 수 있지만, 균일한 막질을 얻기 쉽고, 또한 핀정공이 발생하기 어렵다는 등의 점에서 진공증착법에 의해 형성하는 것이 바람직하다. 상기 진공증착법에 의해 정공주입층을 형성하는 경우 그 증착조건은 정공주입층의 재료로서 사용하는 화합물, 목적하는 정공주입층의 구조 및 열적특성 등에 따라 다르지만, 일반적으로 50-500 ℃의 증착온도, 10-5 내지 10-3 torr의 진공도, 0.01 내지 100 Å/sec의 증착속도, 10 Å 내지 5 ㎛의 층 두께 범위에서 적절히 선택하는 것이 바람직하다.Next, a hole injection layer material may be formed on the anode electrode by a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB (Langmuir-Blodgett) method, but it is easy to obtain a uniform film quality, It is preferable to form it by a vacuum evaporation method. When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the desired hole injection layer, and the like. In general, the deposition temperature is 50-500 [ A vacuum degree of 10 -5 to 10 -3 torr, a deposition rate of 0.01 to 100 Å / sec, and a layer thickness range of 10 Å to 5 탆.
상기 정공주입층 물질은 특별히 제한되지 않으며, 미국특허 제4,356,429호에 개시된 구리 프탈로시아닌 등의 프탈로시아닌 화합물 또는 스타버스트형 아민 유도체류인 TCTA(4,4',4"-트리(N-카바졸릴)트리페닐아민), m-MTDATA(4,4',4"-트리스(3-메틸페닐아미노)트리페닐아민), m-MTDAPB(4,4',4"-트리스(3-메틸페닐아미노)페녹시벤젠), HI-406(N1,N1'-(비페닐-4,4'-디일)비스(N1-(나프탈렌-1-일)-N4,N4-디페닐벤젠-1,4-디아민) 등을 정공주입층 물질로 사용할 수 있다.The hole injection layer material is not particularly limited and may be a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a star burst type amine derivative TCTA (4,4 ', 4 "-tri (N-carbazolyl) (4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine), m-MTDAPB ), HI-406 (N1, N1'- (biphenyl-4,4'-diyl) bis (N1- (naphthalen- 1 -yl) -N4, N4-diphenylbenzene- It can be used as a hole injection layer material.
다음으로 상기 정공주입층 상부에 정공수송층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 형성할 수 있지만, 균일한 막질을 얻기 쉽고, 핀정공이 발생하기 어렵다는 점에서 진공증착법에 의해 형성하는 것이 바람직하다. 상기 진공증착법에 의해 정공수송층을 형성하는 경우 그 증착조건은 사용하는 화합물에 따라 다르지만 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다. 상기 정공수송층 물질은 정공수송층에 사용되고 있는 통상의 공지 물질 중에서 임의로 선택하여 사용할 수 있으며, 구체적으로, N-페닐카바졸, 폴리비닐카바졸 등의 카바졸 유도체, N,N'-비스(3-메틸페닐)-N,N'-디페닐-[1,1-비페닐]-4,4'-디아민(TPD), .N'-디(나프탈렌-1-일)-N,N'-디페닐 벤지딘(α-NPD) 등의 방향족 축합환을 가지는 통상의 아민 유도체 등이 사용될 수 있다.Next, a hole transporting layer material may be formed on the hole injecting layer by a method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, etc. However, since a uniform film quality can be easily obtained, It is preferably formed by a vapor deposition method. When the hole transporting layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select the conditions within the substantially same range as the formation of the hole injection layer. The hole transport layer material may be selected from among conventionally known materials used in the hole transport layer. Specifically, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3- Methylphenyl) -N, N'-diphenyl- [1,1-biphenyl] -4,4'-diamine (TPD), N'-di (naphthalen- And general amine derivatives having an aromatic condensed ring such as benzidine (? -NPD).
그 후, 상기 정공수송층 상부에 발광층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 형성할 수 있지만, 균일한 막질을 얻기 쉽고, 핀정공이 발생하기 어렵다는 점에서 진공증착법에 의해 형성하는 것이 바람직하다. 상기 진공증착법에 의해 발광층을 형성하는 경우 그 증착조건은 사용하는 화합물에 따라 다르지만 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다. 또한, 상기 발광층 재료는 공지의 호스트 및 도펀트를 사용할 수 있다. 도펀트로는 제한되지 않으나 인광 또는 형광 도펀트를 함께 사용하여 발광층을 형성할 수 있으며 일례로, 형광 도펀트로는 BD142(N6,N12-비스(3,4-디메틸페닐)-N6,N12-디메시틸크리센-6,12-디아민)를 사용할 수 있으며, 인광 도펀트로는 녹색 인광 도펀트 Ir(ppy)3(트리스(2-페닐피리딘) 이리듐), 청색 인광 도펀트인 F2Irpic(이리듐(Ⅲ) 비스[4,6-다이플루오로페닐)-피리디나토-N,C2'] 피콜린산염), UDC사의 적색 인광 도펀트 RD61 등이 공동 진공증착(도핑)될 수 있다. 도펀트의 도핑농도는 특별히 제한되지 않으나, 호스트 100 중량부 대비 도펀트가 0.01 내지15 중량부로 도핑되는 것이 바람직하다. 만약 도펀트의 함량이 0.01 중량부 미만일 경우에는 도펀트량이 충분치 못하여 발색이 제대로 이루어지지 않는다는 문제점이 있으며, 15 중량부를 초과할 경우에는 농도 소광 현상으로 인해 효율이 급격히 감소된다는 문제점이 있다.Thereafter, the light emitting layer material may be formed on the hole transporting layer by a method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, etc. However, from the viewpoint of obtaining a uniform film quality and difficulty in producing pin holes, As shown in Fig. When the light emitting layer is formed by the vacuum vapor deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select the conditions within the same range as the formation of the hole injection layer. As the light emitting layer material, well-known hosts and dopants can be used. The light emitting layer may be formed by using a phosphorescent dopant or a fluorescent dopant together. For example, the fluorescent dopant may include BD142 (N6, N12-bis (3,4-dimethylphenyl) -N6, N12- (2-phenylpyridine) iridium), a blue phosphorescent dopant such as F2Irpic (iridium (III) bis [4 , 6-difluorophenyl) -pyridinate-N, C2 '] picolinate), UDC's red phosphorescent dopant RD61 and the like can be vacuum vacuum deposited (doped). The doping concentration of the dopant is not particularly limited, but is preferably doped with 0.01 to 15 parts by weight of the dopant relative to 100 parts by weight of the host. If the content of the dopant is less than 0.01 part by weight, the amount of the dopant is not sufficient and color development is not properly performed. If the amount is more than 15 parts by weight, the efficiency is drastically reduced due to the concentration quenching phenomenon.
또한, 발광층에 인광 도펀트와 함께 사용할 경우에는 삼중항 여기자 또는 정공이 전자수송층으로 확산되는 현상을 방지하기 위하여 정공저지층 재료(HBL)를 추가로 진공증착법 또는 스핀코팅법에 의해 적층시키는 것이 바람직하다. 이때 사용할 수 있는 정공저지층 재료로는 통상의 공지 물질을 단독 또는 혼합하여 사용할 수 있다. 또한 본 발명의 화학식 1로 표현되는 화합물을 사용할 수 있으며, 이때 통상의 공지 물질을 임의로 선택하여 혼합 사용할 수도 있다. 공지 물질의 예로서, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 또는 일본특개평 11-329734(A1)에 기재되어 있는 정공저지층 재료 등을 들 수 있으며, 대표적으로 Balq(비스(8-하이드록시-2-메틸퀴놀리놀나토)-알루미늄 비페녹사이드), 페난트롤린(phenanthrolines)계 화합물(예: UDC사BCP(바쏘쿠프로인)) 등을 사용할 수 있다.When the phosphorescent dopant is used together with the phosphorescent dopant, it is preferable to further laminate the hole blocking layer material (HBL) by a vacuum evaporation method or a spin coating method in order to prevent the triplet exciton or hole from diffusing into the electron transporting layer . As the hole blocking layer material that can be used at this time, conventionally known materials may be used alone or in combination. The compound represented by the formula (1) of the present invention may be used. In this case, conventionally known substances may be arbitrarily selected and mixed. Examples of known materials include oxadiazole derivatives and triazole derivatives, phenanthroline derivatives, and hole blocking layer materials described in Japanese Patent Laid-Open Publication No. 11-329734 (A1). Representative examples include Balq (bis Phenanthrolines based compounds (e.g., UDC company BCP (Bassocouroin)), and the like can be used.
상기와 같이 형성된 발광층 상부에는 전자수송층이 형성되는데, 이때 상기 전자수송층은 진공증착법, 스핀코팅법, 캐스트법 등의 방법으로 형성되며, 특히 진공증착법에 의해 형성하는 것이 바람직하다. 상기 전자수송층 재료로는 본 발명의 화학식 1로 표시되는 화합물을 사용하는 것이 좋으며, 또한 전자수송층에 사용되고 있는 통상의 공지 물질 중에서 임의로 선택하여 사용할 수 있다. 예를들어, 퀴놀린 유도체, 특히 트리스(8-퀴놀리놀라토)알루미늄(Alq3), 또는 ET4(6,6'-(3,4-디메시틸-1,1-디메틸-1H-실올-2,5-디일)디-2,2'-비피리딘)을 사용할 수 있다. An electron transport layer is formed on the light emitting layer formed as described above. The electron transport layer is formed by a vacuum deposition method, a spin coating method, a casting method, or the like, and is preferably formed by a vacuum deposition method. As the material of the electron transport layer, it is preferable to use the compound represented by the formula (1) of the present invention, and it can be arbitrarily selected from common known materials used in the electron transport layer. For example, a quinoline derivative, especially tris (8-quinolinolato) aluminum (Alq3), or ET4 (6,6 '- (3,4-demimethy1-1,1-dimethyl- , 5-diyl) di-2,2'-bipyridine) can be used.
전자수송층 상부에 캐소드로부터 전자의 주입을 용이하게 하는 기능을 가지는 물질인 전자주입층이 적층될 수 있으며, 전자주입층 물질로는 LiF, NaCl, CsF, Li2O, BaO 등의 물질을 이용할 수 있다. An electron injection layer may be stacked on the electron transport layer as a material having a function of facilitating the injection of electrons from the cathode. The electron injection layer material may be LiF, NaCl, CsF, Li2O, BaO, or the like.
상기 전자주입층은 통상의 전자주입층 물질을 진공증착법, 스핀코팅법, 캐스트법 등의 방법으로 형성되며, 특히 진공증착법에 의해 형성하는 것이 바람직하다.The electron injection layer is formed by a conventional vacuum deposition method, a spin coating method, a casting method, or the like, and is preferably formed by a vacuum deposition method.
마지막으로 전자주입층 상부에 캐소드 형성용 금속을 진공증착법이나 스퍼터링법 등의 방법에 의해 형성하고 캐소드로 사용한다. 여기서 캐소드 형성용 금속으로는 낮은 일함수를 가지는 금속, 합금, 전기전도성 화합물, 및 이들의 혼합물을 사용할 수 있다. 구체적인 예로는 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리튬(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등이 있다. 또한, 전면 발광소자를 얻기 위하여 ITO, IZO를 사용한 투과형 캐소드를 사용할 수도 있다.Finally, a metal for forming a cathode is formed on the electron injection layer by a vacuum evaporation method, a sputtering method, or the like, and used as a cathode. As the metal for cathode formation, a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof can be used. Specific examples thereof include Li, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, . Also, a transmissive cathode using ITO or IZO may be used to obtain a front light emitting element.
본 발명의 유기발광소자는 애노드, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층, 캐소드 구조의 유기발광소자 뿐만 아니라, 다양한 구조의 유기발광소자의 구조가 가능하며, 필요에 따라 1층 또는 2층의 중간층을 더 형성하는 것도 가능하다.The organic light emitting device of the present invention can have an organic light emitting device having various structures as well as an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode structure, Layer or an intermediate layer of two layers may be further formed.
상기와 같이 본 발명에 따라 형성되는 각 유기물층의 두께는 요구되는 정도에 따라 조절할 수 있으며, 바람직하게는 10 내지 1,000 ㎚이며, 더욱 바람직하게는 20 내지 150 ㎚인 것이 좋다.As described above, the thickness of each organic material layer formed according to the present invention can be controlled according to the required degree, preferably 10 to 1,000 nm, and more preferably 20 to 150 nm.
또한 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 유기물층의 두께를 분자 단위로 조절할 수 있기 때문에 표면이 균일하며, 형태안정성이 뛰어난 장점이 있다.In addition, since the organic material layer containing the compound represented by the formula (1) can control the thickness of the organic material layer in the molecular unit, the present invention has advantages of uniform surface and excellent shape stability.
이하에서는 본 발명의 일실시예에 따른 화합물의 합성예 및 유기발광소자 제조예를 통하여 본 발명을 더 상세하게 설명한다. 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to synthesis examples of compounds according to one embodiment of the present invention and production examples of organic light emitting devices. The following examples illustrate the invention and are not intended to limit the scope of the invention.
본 발명의 일실예에 따른 화합물의 합성예에 사용된 반응물은 다음과 같다. The reactants used in the synthesis examples of the compounds according to one embodiment of the present invention are as follows.
반응물(1)The reactants (1)
반응물(2)Reactants (2)
반응물(3)The reactants (3)
반응물(4)Reactants (4)
반응물(5)The reactants (5)
반응물(6)Reactants (6)
화합물 compound 1 의1 of 합성 synthesis
아르곤 또는 질소분위기하에서, 250 ml 들이 플라스크에, 1,4-다이브로모 2,3,5,6-테트라메틸벤젠 4.2 g, 반응물 (1) 6.8 g, 테트라키스(트라이페닐포스핀)팔라듐(0) 0.6 g을 다이옥산 50 ml에 녹이고 탄산나트륨 7.6 g을 물 20 ml에 용해한 시킨 것을 추가 한 후, 24시간동안 가열 교반하였다. 반응 후, 실온까지 냉각시켜 석출된 결정을 여과 분리하였다. 이를 톨루엔으로 재결정하여 2.7 g (40%)의 화합물 1을 합성하였다.4.2 g of 1,4-dibromo 2,3,5,6-tetramethylbenzene, 6.8 g of the reactant (1), and tetrakis (triphenylphosphine) palladium (0) were added to a 250 ml flask under an atmosphere of argon or nitrogen. ) Was dissolved in 50 ml of dioxane, and 7.6 g of sodium carbonate dissolved in 20 ml of water was added thereto, followed by heating and stirring for 24 hours. After the reaction, the reaction mixture was cooled to room temperature and the precipitated crystals were separated by filtration. This was recrystallized from toluene to obtain 2.7 g (40%) of Compound 1.
1H-NMR (CDCl3, 400MHz): δ 7.46-7.50 (4H, m), 7.54-7.63 (10H, m), 7.69-7.74 (6H, m), 7.86 (1H, d), 8.04 (1H, d), 8.75-8.81 (6H, m)1 H-NMR (CDCl 3 , 400MHz):? 7.46-7.50 (4H, m), 7.54-7.63 (10H, m), 7.69-7.74 ), 8.75-8.81 (6 H, m)
LC-MS Purityis 99.91 %, Rt=2.67min; MS Calcd.: 748.3; MS Found: 749[M].LC-MS Purity < / RTI > 99.91%, Rt = 2.67 min; MS Calcd.: 748.3; MS Found: 749 [M].
화합물 compound 2 의2 of 합성 synthesis
화합물 1과 같은 방법으로 반응물(1) 대신 반응물(2)를 대신 사용하여 화합물 2를 합성하였다.Compound 2 was synthesized by using the reaction product (2) instead of the reactant (1) in the same manner as the compound (1).
MS Calcd.: 748.3; MS Found: 749[M].MS Calcd.: 748.3; MS Found: 749 [M].
화합물 compound 3 의3 of 합성 synthesis
화합물 1과 같은 방법으로 반응물(1) 대신 반응물(3)을 대신 사용하여 화합물 3을 합성하였다.Compound 3 was synthesized by using the reaction product (3) instead of the reactant (1) in the same manner as the compound (1).
MS Calcd.: 640.3; MS Found: 640[M].MS Calcd .: 640.3; MS Found: 640 [M].
화합물 compound 4 의4 of 합성 synthesis
화합물 1와 같은 방법으로 반응물(1) 대신 반응물(4)를 대신 사용하여 화합물 4를 합성하였다.Compound 4 was synthesized by using the reaction product (4) instead of the reactant (1) in the same manner as the compound (1).
MS Calcd.: 640.3; MS Found: 640[M].MS Calcd .: 640.3; MS Found: 640 [M].
화합물 compound 5 의5 of 합성 synthesis
화합물 1와 같은 방법으로 반응물(1) 대신 반응물(2)와 반응물(3)을 대신 사용하여 화합물 5를 합성하였다.Compound 5 was synthesized by using the reactant (2) and the reactant (3) instead of the reactant (1) in the same manner as the compound (1).
MS Calcd.: 694.3; MS Found: 695[M].MS Calcd.: 694.3; MS Found: 695 [M].
화합물 compound 6 의6 of 합성 synthesis
화합물 1과 같은 방법으로 반응물(1)과 반응물(3)을 사용하여 화합물 6을 합성하였다.Compound 6 was synthesized by using reactant (1) and reactant (3) in the same manner as compound 1.
MS Calcd.: 694.3; MS Found: 695[M].MS Calcd.: 694.3; MS Found: 695 [M].
화합물 compound 7 의7's 합성 synthesis
화합물 1와 같은 방법으로 반응물(1) 대신 반응물(2)와 반응물 (4)를 대신 사용하여 화합물 7을 합성하였다.Compound 7 was synthesized by using the reactant (2) and the reactant (4) instead of the reactant (1) in the same manner as the compound (1).
MS Calcd.: 694.3; MS Found: 695[M].MS Calcd.: 694.3; MS Found: 695 [M].
화합물 compound 8 의8 of 합성 synthesis
화합물 1과 같은 방법으로 반응물(1) 대신 반응물(3)과 반응물 (4)를 대신 사용하여 화합물 8을 합성하였다.Compound 8 was synthesized by using the reactant (3) and the reactant (4) instead of the reactant (1) in the same manner as the compound (1).
MS Calcd.: 694.3; MS Found: 695[M].MS Calcd.: 694.3; MS Found: 695 [M].
화합물 compound 9 의9 of 합성 synthesis
화합물 1과 같은 방법으로 반응물(1) 대신 반응물(5)를 대신 사용하여 화합물 9를 합성하였다.Compound 9 was synthesized by using the reaction product (5) instead of the reactant (1) in the same manner as the compound (1).
MS Calcd.: 690.3; MS Found: 690[M].MS Calcd .: 690.3; MS Found: 690 [M].
화합물 10(a)의 합성Synthesis of Compound 10 (a)
화합물 1과 같은 방법으로 반응물(1) 대신 반응물(6)을 대신 사용하여 화합물 10(a)를 합성하였다.Compound 10 (a) was synthesized by using the reaction product (6) instead of the reactant (1) in the same manner as the compound (1).
화합물 10의 합성Synthesis of
아르곤 또는 질소 분위기 하에서 500 mL 들이 플라스크에 화합물 10(a), 27.3 g, 다이페닐포스핀옥사이드 38 g, 무수인산칼륨 81 g, 다이클로로(1,3-(비스다이페닐포스피노)프로펜)니켈(II) 6.3 g 및 다이옥산 500 mL를 넣고, 환류하면서 24시간 가열 교반하였다. 반응이 더 이상 진행되지 않으면 실온까지 냉각시켜 증류수 200 mL를 넣고, MC 30 mL로 3회 추출하였다. 무수황산나트륨으로 수분제거 후 헥산:에틸 아세테이트(1:1)를 이동상으로 컬럼분리하여 흰색 고체 화합물 10 (16 g, 30%)를 얻었다.(A), 27.3 g, diphenylphosphine oxide, 38 g, anhydrous potassium phosphate, 81 g, dichloro (1,3- (bisdiphenylphosphino) propene) in a 500 mL flask under argon or nitrogen atmosphere, 6.3 g of nickel (II) and 500 mL of dioxane were placed, and the mixture was heated and stirred under reflux for 24 hours. If the reaction is no longer proceeding, cool to room temperature, add 200 mL of distilled water, and extract three times with 30 mL of MC. After removal of water with anhydrous sodium sulfate, hexane: ethyl acetate (1: 1) was subjected to column separation using a mobile phase to obtain a white solid compound 10 (16 g, 30%).
유기발광소자의 제조Manufacture of organic light emitting device
도 1에 기재된 구조에 따라 유기발광소자를 제조하였다. 유기발광소자는 아래로부터 애노드(11) / 정공주입층(12) / 정공수송층(13) / 발광층(14)/ 전자수송층(15) / 캐소드(16) 순으로 적층하였다.An organic light emitting device was prepared according to the structure shown in FIG. The organic light emitting device was stacked in this order from the bottom in the order of the
실시예 및 비교예의 정공주입층(12), 정공전달층(13), 발광층(14), 전자수송층(15)은 아래와 같은 물질을 사용하였다.The following materials were used for the
실시예Example 1 One
인듐틴옥사이드(ITO)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척 이후에 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송시킨 다음 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 ITO 기판 상부에 열 진공 증착기(thermal evaporator)를 이용하여 정공주입층으로 HI01 600Å, 정공수송층으로 Ref.4, 250 Å를 제막하였다. 다음, 상기 발광층으로 BH01:BD01 5%로 도핑하여 250 Å 제막하였다. 다음으로 전자수송층으로 화합물 1과 Liq을 1:1비율로 하여 300 Å 제막한 후 LiF 10 Å, 알루미늄(Al) 1000 Å 제막하고, 이 소자를 글로브 박스에서 밀봉(Encapsulation)함으로써 유기발광소자를 제작하였다.A glass substrate coated with a thin film of indium tin oxide (ITO) at a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing with distilled water, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, and methanol, dried and transferred to a plasma cleaner, and then the substrate was cleaned using oxygen plasma for 5 minutes. Then, a thermal vacuum evaporator evaporator) to form HI01 600 Å as a hole injection layer and Ref.4 and 250 Å as a hole transport layer. Next, the light emitting layer was doped with BH01: BD01 5% to form a 250 Å layer. Next, a 300 Å film was formed by using Compound 1 and Liq as a electron transport layer in a ratio of 1: 1,
실시예Example 2 내지 2 to 실시예Example 9 9
실시예 1과 같은 방법으로 전자수송층을 화합물 1 대신 각각 화합물 2 내지 화합물 10을 사용하여 제막한 유기발광소자를 제작하였다.An organic luminescent device in which an electron transport layer was formed by using Compound 2 to Compound 10 instead of Compound 1 was prepared in the same manner as in Example 1.
비교예Comparative Example 1 One
상기 실시예의 전자수송층을 화합물1대신 ET-01을 사용한 것을 제외하고는 동일한 방법으로 소자를 제작하였다.The device was fabricated in the same manner except that ET-01 was used instead of Compound 1 in the electron transport layer of the above example.
비교예Comparative Example 2 2
상기 실시예의 전자수송층을 화합물1대신 ET-02을 사용한 것을 제외하고는 동일한 방법으로 소자를 제작하였다.The device was fabricated in the same manner except that ET-02 was used instead of Compound 1 in the electron transport layer of the above example.
유기발광소자의 성능평가Evaluation of performance of organic light emitting device
키슬리 2400 소스 메져먼트 유닛(Kiethley 2400 source measurement unit) 으로 전압을 인가하여 전자 및 정공을 주입하고 코니카 미놀타(Konica Minolta) 분광복사계(CS-2000)를 이용하여 빛이 방출될 때의 휘도를 측정함으로써, 실시예 및 비교예의 유기발광소자의 성능을 인가전압에 대한 전류 밀도 및 휘도를 대기압 조건하에 측정하여 평가하였으며, 그 결과를 표 1에 나타내었다.A voltage was applied to the Keithley 2400 source measurement unit to inject electrons and holes and the luminance was measured using a Konica Minolta spectroscope (CS-2000). The performance of the organic light emitting devices of the examples and comparative examples was evaluated by measuring the current density and the luminance with respect to the applied voltage under the atmospheric pressure condition, and the results are shown in Table 1.
상기 표 1에 나타나는 바와 같이, 비교예에 비하여 효율 및 수명이 현저히 우수한 것을 알 수 있다. 또한, 화학식 1의 A, 또는 B가 파라(para) 결합을 이루는 것보다 메타(meta) 결합을 이루는 것이 소자 제작시에 전류 발광 효율이 우수한 것을 확인하였다(파라 결합된 실시예 1의 발광 효율이 5.86 Cd/A인 반면, 메타 결합된 실시예 2의 발광 효율이 5.98 Cd/A로 우수하며, 파라 결합된 실시예 6의 발광 효율이 5.81 Cd/A인 반면, 메타 결합된 실시예 5의 발광 효율이 5.84 Cd/A로 우수하며, 파라 결합된 실시예 8의 발광 효율이 5.80 Cd/A인 반면, 메타 결합된 실시예 7의 발광 효율이 5.90 Cd/A로 우수하게 나타났다). As shown in Table 1, it can be seen that the efficiency and the life are remarkably superior to those of the comparative example. Further, it was confirmed that the meta (meta) bond is more preferable than the case where A or B in formula (1) forms a para bond, 5.86 Cd / A, while the luminous efficiency of the meta-coupled Example 2 is excellent at 5.98 Cd / A and the luminous efficiency of the para-coupled Example 6 is 5.81 Cd / A, while the meta- The efficiency was 5.84 Cd / A, and the luminous efficiency of the para-coupled Example 8 was 5.80 Cd / A, while the luminous efficiency of the meta coupled Example 7 was excellent as 5.90 Cd / A.
10: 애노드(anode)
11: 정공주입층(HIL)
12: 정공수송층(HTL)
13: 발광층(EML)
14: 전자수송층(ETL)
15: 전자주입층(EIL)
16: 캐소드(cathode)10: anode
11: Hole injection layer (HIL)
12: hole transport layer (HTL)
13: Light emitting layer (EML)
14: electron transport layer (ETL)
15: electron injection layer (EIL)
16: cathode
Claims (8)
<화학식 1>
(상기 화학식 1에서 n은 각각 독립적으로 0 내지 2의 정수이며,
X는 각각 독립적으로 C, CR1, 또는 N 이며, 여기서 R1은 수소, 할로겐, 아미노기, 니트릴기, 아릴포스핀옥사이드기, 또는 니트로기이거나 치환되거나 치환되지 않은 C6 ~ C50 의 아릴기 또는 치환되거나 치환되지 않은 C2 ~ C50의 헤테로아릴기이고,
A 및 B는 각각 독립적으로 치환되거나 치환되지 않은 C6 ~ C50 의 아릴기 또는 치환되거나 치환되지 않은 C2 ~ C50의 헤테로아릴기이다)
A compound represented by the following formula (1).
≪ Formula 1 >
(Wherein n is independently an integer of 0 to 2,
X is independently C, CR 1 , or N, wherein R 1 is a hydrogen, a halogen, an amino group, a nitrile group, an arylphosphine oxide group, or a nitro group or a substituted or unsubstituted C 6 -C 50 aryl group Or a substituted or unsubstituted C 2 to C 50 heteroaryl group,
A and B are each independently a substituted or unsubstituted C 6 ~ C 50 aryl group or a substituted or a non-C 2 ~ C 50 heteroaryl group is optionally substituted)
상기 화학식 1의 A, B 중 적어도 하나 이상은 하기 화학식 2로 표현되는 화합물.
<화학식 2>
(상기 화학식 2에서, Y는 각각 독립적으로 CR6, 또는 N 이며, R6는 수소, 할로겐, 아미노기, 니트릴기, 아릴포스핀옥사이드기, 또는 니트로기이거나 치환되거나 치환되지 않은 C6 ~ C50 의 아릴기 또는 치환되거나 치환되지 않은 C2 ~ C50의 헤테로아릴기이고, R3 및 R4는 각각 독립적으로 수소, 아릴포스핀옥사이드기 또는 니트릴기이며, R5는 수소, 치환되거나 치환되지 않은 C6 ~ C50 의 아릴기 또는 치환되거나 치환되지 않은 C2 ~ C50의 헤테로아릴기이다.)
The method according to claim 1,
Wherein at least one of A and B in the formula (1) is represented by the following formula (2).
(2)
Wherein Y is independently CR 6 or N and R 6 is a hydrogen, a halogen, an amino group, a nitrile group, an arylphosphine oxide group, or a nitro group or a substituted or unsubstituted C 6 -C 50 Or a substituted or unsubstituted C 2 to C 50 heteroaryl group, R 3 and R 4 are each independently a hydrogen, an arylphosphine oxide group or a nitrile group, R 5 is hydrogen, a substituted or unsubstituted An unsubstituted C 6 to C 50 aryl group or a substituted or unsubstituted C 2 to C 50 heteroaryl group.)
상기 화학식 1은 하기의 화학식 3으로 표현되는 화합물 중 하나인 화합물.
<화학식 3>
(화학식 3에서, A, B, X, n의 정의는 상기 화학식 1과 동일하며, m은 0 또는 1이다)
The method according to claim 1,
(1) is one of the compounds represented by the following formula (3).
(3)
(Wherein A, B, X and n are the same as in the above formula (1), and m is 0 or 1)
상기 화학식 2의 Y 중 적어도 하나에는 N이 포함되는 화합물.
3. The method of claim 2,
Wherein at least one of Ys in Formula 2 contains N. [
상기 화학식 2의 R3, R4, 및 R6 중 적어도 하나에는 니트릴기 또는 아릴포스핀옥사이드기가 포함되는 화합물.
3. The method of claim 2,
Wherein at least one of R 3 , R 4 , and R 6 in Formula 2 includes a nitrile group or an arylphosphine oxide group.
상기 화합물이 하기 화학식으로 표현되는 화합물 중 하나인 화합물.
The method according to claim 1,
Wherein said compound is one of the compounds represented by the formula:
An organic light-emitting device comprising the compound of any one of claims 1 to 6 between an anode and a cathode.
상기 화합물이 전자수송층 및 정공저지층 중 적어도 하나 이상에 포함되는 것을 특징으로 하는 유기발광소자.8. The method of claim 7,
Wherein the compound is contained in at least one of an electron transport layer and a hole blocking layer.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020160026651A KR102659372B1 (en) | 2016-03-04 | 2016-03-04 | Novel compound and organic electroluminescent device comprising the same |
| CN201780015249.1A CN108779080B (en) | 2016-03-04 | 2017-03-03 | Novel compound and organic light-emitting element comprising same |
| PCT/KR2017/002308 WO2017150930A1 (en) | 2016-03-04 | 2017-03-03 | Novel compound and organic light-emitting device including same |
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| KR1020160026651A KR102659372B1 (en) | 2016-03-04 | 2016-03-04 | Novel compound and organic electroluminescent device comprising the same |
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| KR20170103565A true KR20170103565A (en) | 2017-09-13 |
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| KR (1) | KR102659372B1 (en) |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190038110A (en) * | 2017-09-29 | 2019-04-08 | 삼성에스디아이 주식회사 | Organic compound and composition and organic optoelectronic device and display device |
| WO2020022771A1 (en) * | 2018-07-24 | 2020-01-30 | 주식회사 엘지화학 | Organic light-emitting device |
| WO2023113561A1 (en) * | 2021-12-16 | 2023-06-22 | 주식회사 엘지화학 | Compound and organic light-emitting device comprising same |
| WO2024167187A1 (en) * | 2023-02-06 | 2024-08-15 | 주식회사 엘지화학 | Compound and organic light-emitting element including same |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20210045541A (en) | 2019-10-16 | 2021-04-27 | 삼성디스플레이 주식회사 | Organic electroluminescence device and polycyclic compound for organic electroluminescence device |
| JP7494511B2 (en) | 2020-03-26 | 2024-06-04 | 東ソー株式会社 | Cyclic azine compound, material for organic electroluminescent device, electron transport material for organic electroluminescent device, and organic electroluminescent device |
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| JP2003142267A (en) * | 2001-08-24 | 2003-05-16 | Konica Corp | Material for organic electroluminescent element, electroluminescent element using the same, and display device |
| KR20110033823A (en) * | 2008-06-23 | 2011-03-31 | 스미또모 가가꾸 가부시키가이샤 | Phosphorescence-emitting composition, and light-emitting element utilizing the composition |
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| JP4103492B2 (en) * | 2002-08-09 | 2008-06-18 | コニカミノルタホールディングス株式会社 | Organic electroluminescence element and display device |
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| CN102790184B (en) * | 2012-07-31 | 2016-12-21 | 昆山维信诺显示技术有限公司 | A kind of Amber organic electroluminescent device |
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2016
- 2016-03-04 KR KR1020160026651A patent/KR102659372B1/en active IP Right Grant
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- 2017-03-03 WO PCT/KR2017/002308 patent/WO2017150930A1/en active Application Filing
- 2017-03-03 CN CN201780015249.1A patent/CN108779080B/en active Active
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| JP2003142267A (en) * | 2001-08-24 | 2003-05-16 | Konica Corp | Material for organic electroluminescent element, electroluminescent element using the same, and display device |
| KR20110033823A (en) * | 2008-06-23 | 2011-03-31 | 스미또모 가가꾸 가부시키가이샤 | Phosphorescence-emitting composition, and light-emitting element utilizing the composition |
| WO2015121239A1 (en) * | 2014-02-14 | 2015-08-20 | Hartmut Yersin | Organic molecule having small triplet-singlet energy spacings for effective delayed fluorescence for application in optoelectronic devices |
| WO2015175678A1 (en) * | 2014-05-14 | 2015-11-19 | President And Fellows Of Harvard College | Organic light-emitting diode materials |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20190038110A (en) * | 2017-09-29 | 2019-04-08 | 삼성에스디아이 주식회사 | Organic compound and composition and organic optoelectronic device and display device |
| WO2020022771A1 (en) * | 2018-07-24 | 2020-01-30 | 주식회사 엘지화학 | Organic light-emitting device |
| WO2023113561A1 (en) * | 2021-12-16 | 2023-06-22 | 주식회사 엘지화학 | Compound and organic light-emitting device comprising same |
| WO2024167187A1 (en) * | 2023-02-06 | 2024-08-15 | 주식회사 엘지화학 | Compound and organic light-emitting element including same |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108779080A (en) | 2018-11-09 |
| WO2017150930A1 (en) | 2017-09-08 |
| CN108779080B (en) | 2022-07-26 |
| KR102659372B1 (en) | 2024-04-22 |
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