KR20140077123A - Novel organic compound and electroluminescent device comprising same - Google Patents
Novel organic compound and electroluminescent device comprising same Download PDFInfo
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- KR20140077123A KR20140077123A KR1020130155243A KR20130155243A KR20140077123A KR 20140077123 A KR20140077123 A KR 20140077123A KR 1020130155243 A KR1020130155243 A KR 1020130155243A KR 20130155243 A KR20130155243 A KR 20130155243A KR 20140077123 A KR20140077123 A KR 20140077123A
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- 150000002894 organic compounds Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 238000004519 manufacturing process Methods 0.000 claims abstract description 20
- 239000000463 material Substances 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 31
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 29
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000003277 amino group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 125000002560 nitrile group Chemical group 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 0.000 claims description 19
- 229910044991 metal oxide Inorganic materials 0.000 claims description 15
- 150000004706 metal oxides Chemical class 0.000 claims description 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 6
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- YGDICLRMNDWZAK-UHFFFAOYSA-N quinolin-3-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CN=C21 YGDICLRMNDWZAK-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- HEYPEPZGVKJBFH-UHFFFAOYSA-N 4-(2-bromoethyl)pyridine Chemical compound BrCCC1=CC=NC=C1 HEYPEPZGVKJBFH-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 230000005525 hole transport Effects 0.000 description 3
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- RVPCPPWNSMAZKR-UHFFFAOYSA-N (10-phenylanthracen-9-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C2C=CC=CC2=C1C1=CC=CC=C1 RVPCPPWNSMAZKR-UHFFFAOYSA-N 0.000 description 1
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
- TVOJIBGZFYMWDT-UHFFFAOYSA-N 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CNN=C1 TVOJIBGZFYMWDT-UHFFFAOYSA-N 0.000 description 1
- JBQJVYZMTLIFQG-UHFFFAOYSA-N 9-(10-bromodecyl)-10-phenylanthracene Chemical compound C12=CC=CC=C2C(CCCCCCCCCCBr)=C2C=CC=CC2=C1C1=CC=CC=C1 JBQJVYZMTLIFQG-UHFFFAOYSA-N 0.000 description 1
- WHGGVVHVBFMGSG-UHFFFAOYSA-N 9-bromo-10-phenylanthracene Chemical compound C12=CC=CC=C2C(Br)=C2C=CC=CC2=C1C1=CC=CC=C1 WHGGVVHVBFMGSG-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- PBSIVXAPTBHFFV-UHFFFAOYSA-N [4-(1-phenylbenzimidazol-2-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=NC2=CC=CC=C2N1C1=CC=CC=C1 PBSIVXAPTBHFFV-UHFFFAOYSA-N 0.000 description 1
- YNDGEMZBYUVHTH-UHFFFAOYSA-N [4-(10-phenylanthracen-9-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YNDGEMZBYUVHTH-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 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 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- KXJJSKYICDAICD-UHFFFAOYSA-N quinolin-8-ylboronic acid Chemical compound C1=CN=C2C(B(O)O)=CC=CC2=C1 KXJJSKYICDAICD-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- 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
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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
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Abstract
본 발명은 신규한 화합물 및 이를 포함하는 발광소자에 관한 것으로, 본 발명의 화합물은 전자 전달 특성이 우수하므로, 발광소자의 발광물질로 사용되어 발광소자의 구동전압, 발광효율 및 수명 특성을 향상시킬 수 있으며, 또한 제조생산성을 현저히 향상시킬 수 있다.TECHNICAL FIELD The present invention relates to a novel compound and a light emitting device comprising the same, and the compound of the present invention has excellent electron transfer characteristics, and thus is used as a light emitting material of a light emitting device to improve a driving voltage, a light emitting efficiency, And can also significantly improve manufacturing productivity.
Description
본 발명은 신규한 화합물 및 이를 포함하는 발광소자에 관한 것이다.
The present invention relates to a novel compound and a light emitting device comprising the same.
최근, 자체 발광형으로 저전압 구동이 가능한 유기발광소자는, 평판 표시소자의 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 from the viewpoint of power consumption and has a wide color reproduction range.
일반적으로, 유기발광소자는 음극(전자주입전극)과 양극(정공주입전극), 및 상기 두 전극 사이에 유기층을 포함하는 구조를 갖는다. 이때, 유기층은 발광층(EML, light emitting layer) 이외에, 정공주입층(HIL, hole injection layer), 정공수송층(HTL, hole transport layer), 전자수송층(ETL, electron transport layer) 또는 전자주입층(EIL, electron injection layer)을 포함할 수 있으며, 발광층의 발광특성상 전자차단층(EBL, electron blocking layer) 또는 정공차단층(HBL, hole blocking layer)을 추가로 포함할 수 있다.Generally, an organic light emitting device has a structure including a cathode (electron injection electrode), an anode (hole injection electrode), and an organic layer between the two electrodes. In this case, the organic layer may include a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer (EIL) and an electron injection layer, and may further include an electron blocking layer (EBL) or a hole blocking layer (HBL) on the light emitting property of the light emitting layer.
이러한 구조의 유기발광소자에 전기장이 가해지면, 양극으로부터 정공이 주입되고, 음극으로부터 전자가 주입되어, 정공과 전자는 각각 정공수송층과 전자수송층을 거쳐 발광층에서 재조합(recombination)하게 되어 발광여기자(excitons)를 형성한다. 형성된 발광여기자는 바닥상태(ground states)로 전이하면서 빛을 방출한다. 발광상태의 효율과 안정성을 증가시키기 위하여, 발광 색소(도펀트)를 발광층(호스트)에 도핑하기도 한다.When an electric field is applied to the organic light emitting device having such a structure, holes are injected from the anode, electrons are injected from the cathode, and holes and electrons recombine in the light emitting layer through the hole transporting layer and the electron transporting layer, respectively, ). The formed luminescent excitons emit light while transitioning to ground states. In order to increase the efficiency and stability of the light emitting state, a light emitting colorant (dopant) is also doped in the light emitting layer (host).
유기발광소자의 발광층에 사용되는 물질로서 다양한 화합물들이 알려져 있으나, 이제까지 알려진 발광물질을 이용한 유기발광소자의 경우 높은 구동전압, 낮은 효율 및 짧은 수명으로 인해 실용화하는 데에 많은 어려움이 있었다. 따라서, 우수한 발광특성을 갖는 물질을 이용하여 저전압 구동, 고휘도 및 장수명을 갖는 유기발광소자를 개발하려는 노력이 지속되어 왔다.Various compounds have been known as materials used in the light emitting layer of organic light emitting devices. However, organic light emitting devices using known light emitting materials have been difficult to put to practical use due to high driving voltage, low efficiency, and short life span. Accordingly, efforts have been made to develop an organic light emitting device having low voltage driving, high brightness, and long life using a material having excellent light emission characteristics.
또한, 최근 유기발광소자와 더불어 전자주입층 또는 전자수송층을 n형 반도체 산화금속으로 구성하여 전계발광 효율 및 휘도를 개선하고자 하는 하이브리드 유무기 발광소자(HOLED)에 대한 연구가 다각적으로 시도되고 있으며, 대한민국 특허공개공보 제10-2011-0132165호에는 상기 HOLED의 n형 반도체 산화금속을 특정한 화학식의 자기조립 쌍극자 분자로 개질하여 성능을 향상시킨 HOLED에 대하여 개시하고 있으나, 아직까지 HOLED의 제조생산성 및 성능개선에 대한 요구가 절실히 요청되고 있는 실정이다.
Recently, researches on a hybrid organic light emitting device (HOLED), which is composed of an electron injection layer or an electron transport layer together with an organic light emitting device as an n-type semiconductor oxide metal to improve the electroluminescence efficiency and brightness, Korean Patent Laid-Open Publication No. 10-2011-0132165 discloses a HOLED in which the n-type semiconductor oxide of the HOLED is modified by self-assembled dipole molecules of a specific formula to improve the performance. However, the productivity and performance There is a desperate need for improvement.
상기와 같은 문제점을 해결하기 위해, 본 발명은 전자 전달 특성이 우수하여 구동전압이 우수하고 높은 발광효율과 발광휘도를 가지며 장수명 구현이 가능할 뿐만 아니라 제조생산성을 현저히 향상시킬 수 있는 화합물 및 이를 포함하는 발광소자를 제공하는 것을 목적으로 한다.
Disclosure of the Invention In order to solve the above problems, it is an object of the present invention to provide a compound which is excellent in electron transferring property, excellent in driving voltage, has high luminous efficiency and light emission luminance, can realize long life, And to provide a light emitting element.
상기 목적을 달성하기 위해 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to accomplish the above object, the present invention provides a compound represented by the following formula 1:
[화학식 1][Chemical Formula 1]
A-(RA- (R aa )) nn -(R- (R bb )) mm -D-D pp
상기 식에서,In this formula,
A는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, 치환되거나 치환되지 않은 C1~C40의 알킬기, C2~C40의 알케닐기, C1~C40의 알콕시기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C6~C40의 아릴기 및 C3~C40의 헤테로아릴기, 및 Si로 이루어진 군으로부터 선택된 하나 이상의 기로 치환되거나 치환되지 않은 형광 또는 인광 화합물이고;A is a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a substituted or unsubstituted C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 1 ~ C 40 of the alkoxy group, C 3 ~ C 40 Substituted or unsubstituted with one or more groups selected from the group consisting of a cycloalkyl group having 1 to 20 carbon atoms, a C 3 to C 40 heterocycloalkyl group, a C 6 to C 40 aryl group and a C 3 to C 40 heteroaryl group, and Si; A phosphorescent compound;
Ra는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C1~C40의 알콕시기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C6~C40의 아릴기 및 C3~C40의 헤테로아릴기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환되거나 치환되지 않은 Si; C1~C40의 알킬기; C3~C40의 시클로알킬기; C3~C40의 알케닐기; C3~C40의 알콕시기; 아미노기; C6~C40의 아릴기; 또는 C3~C40의 헤테로아릴기이고, 여기서, 인접 고리는 서로 융합될 수 있으며; R a is a group selected from the group consisting of deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 1 to C 40 alkoxy group, a C 3 to C 40 cycloalkyl group, Si substituted or unsubstituted with at least one group selected from the group consisting of C 3 to C 40 heterocycloalkyl groups, C 6 to C 40 aryl groups and C 3 to C 40 heteroaryl groups; A C 1 to C 40 alkyl group; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 alkenyl group; A C 3 to C 40 alkoxy group; An amino group; A C 6 to C 40 aryl group; Or a C 3 to C 40 heteroaryl group, wherein adjacent rings may be fused to each other;
Rb는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C1~C40의 알콕시기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C6~C40의 아릴기 및 C3~C40의 헤테로아릴기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환되거나 치환되지 않은 Si; C1~C40의 알킬기; C3~C40의 시클로알킬기; C3~C40의 알케닐기; C3~C40의 알콕시기; 아미노기; C6~C40의 아릴기; 또는 C3~C40의 헤테로아릴기이고, 여기서, 인접 고리는 서로 융합될 수 있고;R b is selected from the group consisting of deuterium, halogen, amino, nitrile, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 1 to C 40 alkoxy, C 3 to C 40 cycloalkyl, Si substituted or unsubstituted with at least one group selected from the group consisting of C 3 to C 40 heterocycloalkyl groups, C 6 to C 40 aryl groups and C 3 to C 40 heteroaryl groups; A C 1 to C 40 alkyl group; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 alkenyl group; A C 3 to C 40 alkoxy group; An amino group; A C 6 to C 40 aryl group; Or a C 3 to C 40 heteroaryl group, wherein adjacent rings may be fused to each other;
D는 하기 화학식 Fg1 내지 Fg14로 표시되는 것 중 하나이며, 여기서 *는 연결부분이며, Fg1 내지 Fg14에 함유된 하나 이상의 수소는 각각 독립적으로 중수소; 할로겐; 아미노기; 니트릴기; 니트로기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환된 치환되거나 치환되지 않은 Si; C1~C40의 알킬기; C3~C40의 시클로알킬기; C3~C40의 알케닐기; C3~C40의 알콕시기; C6~C40의 아릴기; 또는 C3~C40의 헤테로아릴기로 치환될 수 있으며, Rf1은 각각 독립적으로 수소; 중수소; 할로겐; 아미노기; 니트릴기; 니트로기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환된 치환되거나 치환되지 않은 C1~C40의 알킬기; C3~C40의 시클로알킬기; C3~C40의 알케닐기; C3~C40의 알콕시기; C6~C40의 아릴기; 또는 C3~C40의 헤테로아릴기이며;D is one of the following formulas: Fg1 to Fg14, wherein * is a linking moiety, and at least one hydrogen contained in Fg1 to Fg14 is independently selected from the group consisting of deuterium; halogen; An amino group; A nitrile group; A nitro group; Or substituted or unsubstituted Si substituted by deuterium, halogen, amino, nitrile or nitro; A C 1 to C 40 alkyl group; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 alkenyl group; A C 3 to C 40 alkoxy group; A C 6 to C 40 aryl group; Or a C 3 to C 40 heteroaryl group, and each R f1 is independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; Or a substituted or unsubstituted C 1 to C 40 alkyl group substituted by deuterium, halogen, amino, nitrile or nitro; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 alkenyl group; A C 3 to C 40 alkoxy group; A C 6 to C 40 aryl group; Or a C 3 to C 40 heteroaryl group;
n 및 m은 각각 독립적으로 0 내지 10의 정수이고, n and m are each independently an integer of 0 to 10,
p는 1 내지 10의 정수이다:p is an integer from 1 to 10;
Fg1:
Fg1:
또한 본 발명은 상기 화학식 1로 표시되는 화합물의 제조방법을 제공한다.
The present invention also provides a process for preparing the compound represented by the above formula (1).
또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 발광소자를 제공한다.
Also, the present invention provides a light emitting device comprising the compound represented by Formula 1.
또한 본 발명은 상기 화학식 1로 표시되는 화합물을 사용하는 것을 특징으로 하는 발광소자의 제조방법을 제공한다.
The present invention also provides a method of manufacturing a light emitting device, which uses the compound represented by the above formula (1).
본 발명에 따른 화학식 1의 화합물은 금속산화물 표면에 공유결합 형성을 유도하여 금속산화물의 표면에 전자가 풍부하여 페르미 준위(fermi level)를 증가시킴으로써 발광소자 형성시 음극으로부터 주입된 전자가 금속산화물을 통해 발광층으로 이동하는데 있어서 에너지 장벽을 낮출 수 있다.The compound of formula (I) according to the present invention induces covalent bond formation on the surface of a metal oxide to enrich electrons on the surface of the metal oxide to increase the Fermi level, so that electrons injected from the cathode upon formation of a light- It is possible to lower the energy barrier in moving to the light emitting layer.
따라서, 본 발명의 화합물을 발광소자에 적용하면, 금속산화물 계면과 유기물층 사이에 전자이동이 용이하게 되고, 발광소자의 구동전압, 발광효율 및 수명 특성을 현저히 개선시킬 수 있으며, 발광소자에의 적용에 있어서 wet process 공정을 가능하게 하여 발광소자의 제조생산성을 향상시키는데 크게 도움을 줄 수 있다.
Therefore, when the compound of the present invention is applied to a light emitting device, electron transfer between the metal oxide interface and the organic material layer is facilitated, driving voltage, luminous efficiency and lifetime characteristics of the light emitting device can be remarkably improved, The wet process can be performed to improve the productivity of the light emitting device.
도 1은 본 발명의 일실시예에 따른 하이브리드 유·무기 발광소자(HOLED)의 모식도를 나타낸 것이다.
도 2는 본 발명의 일실시예에 따른 유·무기 발광소자(HOLED)의 전류 밀도-전압-휘도(I-V-L) 특성을 나타낸 그래프이다.
도면의 부호
10 : 기판
11 : 음극
12 : 무기나노입자층
13 : 발광층
14 : 정공전달층
15 : 정공주입층
16: 양극1 is a schematic view of a hybrid organic-inorganic light emitting device (HOLED) according to an embodiment of the present invention.
FIG. 2 is a graph showing current density-voltage-luminance (IVL) characteristics of the organic / inorganic light emitting device (HOLED) according to an embodiment of the present invention.
The sign
10: substrate
11: cathode
12: inorganic nanoparticle layer
13:
14: hole transport layer
15: Hole injection layer
16: anode
하기 화학식 1로 표시되는 본 발명의 화합물은 형광 또는 인광 화합물에 전자가 풍부한 작용기가 치환되어 쌍극자 모멘트를 형성하는 것을 특징으로 한다.The compound of the present invention represented by the following formula (1) is characterized in that a functional group rich in electrons is substituted for a fluorescent or phosphorescent compound to form a dipole moment.
[화학식 1][Chemical Formula 1]
A-(RA- (R aa )) nn -(R- (R bb )) mm -D-D pp
상기 식에서,In this formula,
A는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, 치환되거나 치환되지 않은 C1~C40의 알킬기, C2~C40의 알케닐기, C1~C40의 알콕시기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C6~C40의 아릴기, C3~C40의 헤테로아릴기, 및 Si로 이루어진 군으로부터 선택된 하나 이상의 기로 치환되거나 치환되지 않은 형광 또는 인광 화합물이고;A is a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a substituted or unsubstituted C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 1 ~ C 40 of the alkoxy group, C 3 ~ C 40 Substituted or unsubstituted with at least one group selected from the group consisting of a cycloalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 6 to C 40 aryl group, a C 3 to C 40 heteroaryl group, and Si; A phosphorescent compound;
Ra는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C1~C40의 알콕시기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C6~C40의 아릴기 및 C3~C40의 헤테로아릴기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환되거나 치환되지 않은 Si; C1~C40의 알킬기; C3~C40의 시클로알킬기; C3~C40의 알케닐기; C3~C40의 알콕시기; 아미노기; C6~C40의 아릴기; 또는 C3~C40의 헤테로아릴기이고, 여기서, 인접 고리는 서로 융합될 수 있으며; R a is a group selected from the group consisting of deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 1 to C 40 alkoxy group, a C 3 to C 40 cycloalkyl group, Si substituted or unsubstituted with at least one group selected from the group consisting of C 3 to C 40 heterocycloalkyl groups, C 6 to C 40 aryl groups and C 3 to C 40 heteroaryl groups; A C 1 to C 40 alkyl group; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 alkenyl group; A C 3 to C 40 alkoxy group; An amino group; A C 6 to C 40 aryl group; Or a C 3 to C 40 heteroaryl group, wherein adjacent rings may be fused to each other;
Rb는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C1~C40의 알콕시기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C6~C40의 아릴기 및 C3~C40의 헤테로아릴기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환되거나 치환되지 않은 Si; C1~C40의 알킬기; C3~C40의 시클로알킬기; C3~C40의 알케닐기; C3~C40의 알콕시기; 아미노기; C6~C40의 아릴기; 또는 C3~C40의 헤테로아릴기이고, 여기서, 인접 고리는 서로 융합될 수 있고;R b is selected from the group consisting of deuterium, halogen, amino, nitrile, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 1 to C 40 alkoxy, C 3 to C 40 cycloalkyl, Si substituted or unsubstituted with at least one group selected from the group consisting of C 3 to C 40 heterocycloalkyl groups, C 6 to C 40 aryl groups and C 3 to C 40 heteroaryl groups; A C 1 to C 40 alkyl group; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 alkenyl group; A C 3 to C 40 alkoxy group; An amino group; A C 6 to C 40 aryl group; Or a C 3 to C 40 heteroaryl group, wherein adjacent rings may be fused to each other;
D는 하기 화학식 Fg1 내지 Fg14로 표시되는 것 중 하나이며, 여기서 *는 연결부분이며, Fg1 내지 Fg14에 함유된 하나 이상의 수소는 각각 독립적으로 중수소; 할로겐; 아미노기; 니트릴기; 니트로기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환된 치환되거나 치환되지 않은 Si; C1~C40의 알킬기; C3~C40의 시클로알킬기; C3~C40의 알케닐기; C3~C40의 알콕시기; C6~C40의 아릴기; 또는 C3~C40의 헤테로아릴기로 치환될 수 있으며, Rf1은 각각 독립적으로 수소; 중수소; 할로겐; 아미노기; 니트릴기; 니트로기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환된 치환되거나 치환되지 않은 C1~C40의 알킬기; C3~C40의 시클로알킬기; C3~C40의 알케닐기; C3~C40의 알콕시기; C6~C40의 아릴기; 또는 C3~C40의 헤테로아릴기이며;D is one of the following formulas: Fg1 to Fg14, wherein * is a linking moiety, and at least one hydrogen contained in Fg1 to Fg14 is independently selected from the group consisting of deuterium; halogen; An amino group; A nitrile group; A nitro group; Or substituted or unsubstituted Si substituted by deuterium, halogen, amino, nitrile or nitro; A C 1 to C 40 alkyl group; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 alkenyl group; A C 3 to C 40 alkoxy group; A C 6 to C 40 aryl group; Or a C 3 to C 40 heteroaryl group, and each R f1 is independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; Or a substituted or unsubstituted C 1 to C 40 alkyl group substituted by deuterium, halogen, amino, nitrile or nitro; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 alkenyl group; A C 3 to C 40 alkoxy group; A C 6 to C 40 aryl group; Or a C 3 to C 40 heteroaryl group;
n 및 m은 각각 독립적으로 0 내지 10의 정수이고, n and m are each independently an integer of 0 to 10,
p는 1 내지 10의 정수이다:p is an integer from 1 to 10;
Fg1:
Fg1:
본 발명의 화합물에 있어서, 상기 형광 또는 인광 화합물은 기존 형광 또는 인광 화합물로 사용되는 공지의 형광 또는 인광 화합물이 사용될 수 있다.In the compound of the present invention, the fluorescent or phosphorescent compound may be a known fluorescent or phosphorescent compound used as a conventional fluorescent or phosphorescent compound.
구체적인 예로 상기 형광 또는 인광 화합물은 하기 FL1 내지 FL33으로 표시되는 형광화합물이거나 또는 PL1 내지 PL59로 표시되는 인광화합물일 수 있으며, FL1 내지 FL33, 또는 PL1 내지 PL59에서 *는 연결부분이며, 여기서 연결부분은 괄호안의 치환위치 중 하나 이상에 연결될 수 있으며, R1 내지 R16은 각각 독립적으로 수소; 중수소; 할로겐; 아미노기; 니트릴기; 니트로기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1~C40의 알킬기; C2~C40의 알케닐기; C1~C40의 알콕시기; C3~C40의 시클로알킬기; C3~C40의 헤테로시클로알킬기; C6~C40의 아릴기; C3~C40의 헤테로아릴기; 또는 Si이다.As a specific example, the fluorescent or phosphorescent compound may be a phosphorescent compound represented by the following FL1 to FL33 or a phosphorescent compound represented by PL1 to PL59, and * in FL1 to FL33 or PL1 to PL59 is a connecting portion, And R1 to R16 are each independently selected from the group consisting of hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro, unsubstituted or substituted with C 1 ~ C 40 alkyl group; A C 2 to C 40 alkenyl group; A C 1 to C 40 alkoxy group; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 heterocycloalkyl group; A C 6 to C 40 aryl group; A C 3 to C 40 heteroaryl group; Or Si.
FL1:
FL5:
PL1:
PL1:
또한, 본 발명의 화합물에 있어서, 상기 Ra 및 Rb는 형광 또는 인광 화합물과 D의 작용기 사이의 콘쥬게이션(conjugation)을 방지하기 위하여 결합될 수 있으며, 분자내 전자이동을 막아 양자 수득율(quantum yield)이 감소하지 않도록 함으로써 발광효율을 개선시킬 수 있으며, 용해도를 향상시키고, 벌키 그룹(bulky group)들에 의한 파이-파이(π-π) 겹침(stacking)을 줄임으로써 균일한 계면형성 및 소자효율을 향상시킬 수 있다.
In addition, in the compound of the present invention, R a and R b may be combined to prevent conjugation between the fluorescent or phosphorescent compound and the functional group of D, to prevent electron transfer in the molecule, yield can be improved by decreasing the yield, and by improving the solubility and reducing pi-pi stacking by bulky groups, uniform interface formation and device < RTI ID = 0.0 > The efficiency can be improved.
본 발명의 상기 화학식 1의 화합물에 있어서 Ra 및 Rb의 n과 m이 모두 0일 수도 있으며, n과 m은 각각 독립적으로 0 내지 10의 정수이며, 상기 Ra 또는 Rb는 구체적인 일예로 하기와 같은 화합물일 수 있다. 바람직하기로, A가 안트라센기를 포함하는 경우 Ra 또는 Rb 중 적어도 하나는 C1~C40의 알킬기 또는 C2~C40의 알케닐기인 것이 좋다.In the compound of formula (1) of the present invention, n and m in R a and R b may both be 0, and n and m are each independently an integer of 0 to 10, and R a or R b is a specific example May be the following compounds. Preferably, when A comprises an anthracene group, at least one of R a or R b is preferably a C 1 to C 40 alkyl group or a C 2 to C 40 alkenyl group.
하기 화학식에서 *는 연결부분을 나타내며, 연결부위를 제외한 하나 이상의 수소가 중수소; 할로겐; 아미노기; 니트릴기; 니트로기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1~C40의 알킬기; C2~C40의 알케닐기; C1~C40의 알콕시기; C3~C40의 시클로알킬기; C3~C40의 헤테로시클로알킬기; C6~C40의 아릴기; C3~C40의 헤테로아릴기; 및 Si로 이루어진 군으로부터 선택된 기로 하나 이상 치환될 수 있다.Wherein * represents a linking moiety and at least one hydrogen except the linking moiety is deuterium; halogen; An amino group; A nitrile group; A nitro group; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro, unsubstituted or substituted with C 1 ~ C 40 alkyl group; A C 2 to C 40 alkenyl group; A C 1 to C 40 alkoxy group; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 heterocycloalkyl group; A C 6 to C 40 aryl group; A C 3 to C 40 heteroaryl group; And Si. ≪ / RTI >
Ra or Rb =R a or R b =
Ra 또는 Rb는 헤테로 고리 화합물을 포함할 경우에는, 금속산화물의 표면의 전자를 더욱 풍부하게 하기 위하여 상기 헤테로 고리 화합물이 할로겐, -CF3, 또는 -CN 등을 포함하면 더욱 좋다.
When R a or R b includes a heterocyclic compound, it is more preferable that the heterocyclic compound includes halogen, -CF 3 , or -CN or the like in order to enrich electrons on the surface of the metal oxide.
본 발명의 화학식 1의 화합물은 A, Ra, Rb, 및 D가 n, m, 및 p의 값에 따라 임의의 조합을 통하여 결합된 화합물일 수 있으며, n과 m이 모두 0인 경우 A와 D가 직접 결합될 수도 있다. The compound of formula (I) of the present invention may be a compound in which A, R a , R b , and D are bonded through any combination depending on the values of n, m, and p, and when n and m are both 0 And D may be directly combined.
보다 구체적으로 본 발명의 화학식 1로 표시되는 화합물은 하기 화합물들 중 하나일 수 있다.More specifically, the compound represented by Formula 1 of the present invention may be one of the following compounds.
본 발명에 따른 화학식 1의 화합물은 쌍극자 모멘트를 형성하므로, 금속산화물 표면에 공유결합 형성을 유도하여 금속산화물의 표면에 전자가 풍부하게 한다. 이로 인해 페르미 준위(fermi level)를 증가시킴으로써 발광소자 형성시 음극으로부터 주입된 전자가 금속산화물을 통해 발광층으로 이동하는데 있어서 에너지 장벽을 낮출 수 있다.The compound of formula (1) according to the present invention forms a dipole moment, thereby inducing covalent bond formation on the surface of the metal oxide to enrich the surface of the metal oxide with electrons. This increases the Fermi level, thereby lowering the energy barrier when electrons injected from the cathode migrate to the light emitting layer through the metal oxide when the light emitting device is formed.
따라서, 본 발명의 화합물을 HOLED 또는 OLED 등의 발광소자에 적용하면, 금속산화물 계면과 유기물층 사이에 전자이동이 용이하게 되고, 발광소자의 구동전압 및 발광 효율 등의 특성을 향상 시킬 수 있으며, 특히 발광소자에의 적용에 있어서 wet process 공정을 가능하게 하여 발광소자의 제조생산성을 현저히 향상시킬 수 있다.
Therefore, when the compound of the present invention is applied to a light emitting device such as a HOLED or an OLED, electron transfer between the metal oxide interface and the organic layer becomes easy, and characteristics such as a driving voltage and a light emitting efficiency of the light emitting device can be improved. In the application to a light emitting device, a wet process can be performed, and the productivity of the light emitting device can be remarkably improved.
본 발명에 따른 화학식 1의 화합물은 화합물 AX, A-Ra-X, 또는 A-Ra-Rb-X에 D를 결합시켜 제조할 수 있다. 상기에서 A, Ra, Rb, 및 D, Rf1은 화학식 1에서 정의한 바와 같으며, X는 할로겐 화합물이다. The compounds of formula (I) according to the present invention can be prepared by coupling D to compounds AX, A-Ra-X, or A-Ra-Rb-X. In the above, A, R a , R b , and D, R f1 are as defined in formula (1), and X is a halogen compound.
구체적인 예로 본 발명에 따른 화학식 1의 화합물은 하기 반응식들 중 어느 하나를 통하여 제조될 수 있다.
As a specific example, the compounds of formula (1) according to the invention can be prepared via any of the following schemes.
더욱 구체적으로 본 발명에 따른 화학식 1은 하기에 기재된 과정을 통하여 제조될 수 있다.
More specifically, the formula (1) according to the present invention can be prepared through the process described below.
또한, 본 발명은 발광물질로서 상기 화학식 1로 표시되는 화합물을 포함하는 발광소자를 제공한다. 상기 발광소자는 HOLED 또는 OLED 발광소자일 수 있다. 바람직하기로 상기 화합물은 상기 발광소자의 발광층에 포함될 수 있으며, 이때, 본 발명의 화합물은 단독으로 사용되거나 공지의 유기발광 화합물과 함께 사용될 수 있다. 더욱 바람직하기로 본 발명의 발광소자는 HOLED 발광소자이며, 상기 발광소자는 전자주입 또는 전자수송층에 n형 산화금속을 포함할 수 있다. 상기 n형 산화금속은 Zno, TiO2, ZrO2, Ta2O3, MgO 또는 HfO2 등의 금속산화물을 사용하여 형성할 수 있다.
The present invention also provides a light emitting device comprising the compound represented by Formula 1 as a luminescent material. The light emitting device may be a HOLED or an OLED light emitting device. Preferably, the compound may be included in the light emitting layer of the light emitting device, and the compound of the present invention may be used alone or in combination with a known organic light emitting compound. More preferably, the light emitting device of the present invention is a HOLED light emitting device, and the light emitting device may include an n-type metal oxide in the electron injection or electron transport layer. The n-type metal oxide may be formed using a metal oxide such as Zno, TiO 2 , ZrO 2 , Ta 2 O 3 , MgO, or HfO 2 .
또한 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 발광소자의 제조방법을 제공한다. 본 발명의 발광소자의 제조방법에 있어서, 상기 화학식 1의 화합물을 사용하는 것을 제외하고는 공지의 발광소자의 제조방법에 사용되는 공지의 방법들이 적용될 수 있음은 물론이며, 일예로 상기 발광소자는 HOLED 또는 OLED 소자일 수 있으며, 본 발명의 화학식 1의 화합물을 발광층에 포함할 수 있다.The present invention also provides a method of manufacturing a light emitting device comprising the compound represented by Formula 1. In the method of manufacturing a light emitting device of the present invention, it is needless to say that known methods used in a known method for manufacturing a light emitting device can be applied except that the compound of Chemical Formula 1 is used. For example, HOLED or OLED element, and the compound of Formula 1 of the present invention may be included in the light emitting layer.
구체적인 예로 HOLED 발광소자는 화학식 1의 화합물을 발광화합물로 사용하는 것을 제외하고는 대한민국 특허공개 제10-2011-0132165호에 기재된 방법을 적용할 수 있으며, n형 산화금속으로 형성된 전자주입 및 전자 수송층 위에 바로 발광층을 형성할 수도 있다.As a specific example, the HOLED light-emitting device can be applied to the method described in Korean Patent Publication No. 10-2011-0132165, except that the compound of Formula 1 is used as a light-emitting compound. The electron injection and electron transport layer The light emitting layer may be immediately formed.
또한 본 발명의 발광소자는 OLED 발광소자일 수도 있으며, 화학식 1의 화합물을 발광화합물로 사용하는 것을 제외하고는 본 출원인의 선출원인 대한민국특허출원 제10-2009-30213호에 기재된 방법을 통하여 OLED 화합물을 제조할 수도 있다.Also, the light emitting device of the present invention may be an OLED light emitting device. Except that the compound of Formula 1 is used as a light emitting compound, the OLED compound . ≪ / RTI >
본 발명의 발광소자의 제조방법은 발광층의 형성에 있어서, 화학식 1의 화합물을 사용하여 wet process를 통하여 발광층을 형성이 가능하여 발광소자의 제조생산성을 현저히 향상시킬 수 있으며, 발광 효율, 휘도 및 발광소자의 수명을 향상시킬 수 있는 장점이 있다.
In the method for manufacturing a light emitting device of the present invention, it is possible to form a light emitting layer through a wet process using the compound of Chemical Formula 1 in the formation of the light emitting layer, thereby remarkably improving the productivity of the light emitting device, There is an advantage that the lifetime of the device can be improved.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시하나, 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 the following examples. However, the scope of the present invention is not limited to the following examples.
[제조예 1][Production Example 1]
둥근바닥 플라스크에 4-(2-bromoethyl)pyridine 2.5 g과 (10-phenylanthracen-9-yl)boronic acid 4.8 g을 톨루엔 100 ml에 녹이고 2 M K2CO3를 20 ml 넣은 후 질소분위기하에서 30분간 교반하였다. 상기 둥근바닥 플라스크에 팔라듐 촉매 0.5 g을 넣고 환류 교반하였다. 이후 반응이 종결된 후 증류수 및 MC로 추출한 후 감압여과하고 재결정하여 하기 화합물1 2.61 g을 얻었다. 2.5 g of 4- (2-bromoethyl) pyridine and 4.8 g of (10-phenylanthracen-9-yl) boronic acid were dissolved in 100 ml of toluene, 20 ml of 2 MK 2 CO 3 was added to the round bottom flask, Respectively. 0.5 g of palladium catalyst was added to the round bottom flask, and the mixture was refluxed and stirred. After the reaction was completed, the reaction mixture was extracted with distilled water and MC, filtered under reduced pressure, and recrystallized to obtain 2.61 g of the following compound 1.
m/z: 359.17 (100.0%), 360.17 (29.4%), 361.17 (4.2%)m / z: 359.17 (100.0%), 360.17 (29.4%), 361.17 (4.2%)
[제조예 2][Production Example 2]
둥근바닥 플라스크에 4-(2-bromoethyl)pyridine 2.7 g과 (4-(10-phenylanthracen-9-yl)phenyl)boronic acid 6.52 g 을 톨루엔 130 ml에 녹이고 2 M K2CO3를 20 ml 넣은 후 질소분위기하에서 30분간 교반하였다. 상기 둥근바닥 플라스크에 팔라듐 촉매 0.5 g을 넣고 환류 교반하였다. 이후 반응이 종결된 후 증류수 및 MC로 추출한 후 감압여과하고 재결정하여 하기 화합물2 2.84 g을 얻었다. 2.7 g of 4- (2-bromoethyl) pyridine and 6.52 g of 4- (10-phenylanthracen-9-yl) phenyl boronic acid were dissolved in 130 ml of toluene, 20 ml of 2 MK 2 CO 3 was added to the round bottom flask, And the mixture was stirred under an atmosphere for 30 minutes. 0.5 g of palladium catalyst was added to the round bottom flask, and the mixture was refluxed and stirred. After completion of the reaction, the reaction mixture was extracted with distilled water and MC, filtered under reduced pressure, and recrystallized to obtain 2.84 g of the following
m/z: 435.20 (100.0%), 436.20 (36.3%), 437.21 (6.3%)m / z: 435.20 (100.0%), 436.20 (36.3%), 437.21 (6.3%)
[제조예 3][Production Example 3]
둥근바닥 플라스크에 4-(2-bromoethyl)pyridine 2.0 g과 (6-(diphenylamino)pyren-1-yl)boronic acid 5.33 g을 톨루엔 130 ml에 녹이고 2 M K2CO3를 16 ml 넣은 후 질소분위기하에서 30분간 교반하였다. 상기 둥근바닥 플라스크에 팔라듐 촉매 0.37 g을 넣고 환류 교반하였다. 이후 반응이 종결된 후 증류수 및 MC로 추출한 후 감압여과하고 재결정하여 하기 화합물 3 2.5 g을 얻었다. 2.0 g of 4- (2-bromoethyl) pyridine and 5.33 g of 6- (diphenylamino) pyren-1-yl) boronic acid were dissolved in 130 ml of toluene, 16 ml of 2 MK 2 CO 3 was added to the round bottom flask, And stirred for 30 minutes. 0.37 g of palladium catalyst was added to the round bottom flask, and the mixture was refluxed and stirred. After completion of the reaction, the reaction mixture was extracted with distilled water and MC, filtered under reduced pressure, and recrystallized to obtain 2.5 g of the following compound 3.
m/z: 474.21 (100.0%), 475.21 (38.6%), 476.22 (7.1%)m / z: 474.21 (100.0%), 475.21 (38.6%), 476.22 (7.1%)
[제조예 4][Production Example 4]
9-bromo-10-phenylanthracene 8 g를 anhydrous diethyl ether 300 ml에 녹였다. 여기서 0 ℃에서 n-BuLi(2 M) 18 ml를 천천히 넣었다. 0 ℃에서 1시간 유지 후 1,10-dibromodecane 21.6 ml를 넣었다. 30 분 후 2시간 환류 교반하였다. 반응이 더 이상 진행되지 않으면 상온으로 냉각 후 증류수 80 ml를 넣었다. 유기층을 모으고 물층을 에틸에테르 40 ml로 3회 추출하였다. 무수황산마그네슘으로 수분제거 후 hexane을 이동상으로 컬럼분리 하여 연두색 오일상 9-(10-bromodecyl)-10-phenylanthracene 5.7 g을 얻었다.8 g of 9-bromo-10-phenylanthracene was dissolved in 300 ml of anhydrous diethyl ether. 18 ml of n- BuLi (2 M) was slowly added at 0 ° C. After holding at 0 ° C for 1 hour, 21.6 ml of 1,10-dibromodecane was added. After 30 minutes, the mixture was refluxed and stirred for 2 hours. If the reaction did not proceed any further, 80 ml of distilled water was added after cooling to room temperature. The organic layer was collected and the aqueous layer was extracted three times with 40 ml of ethyl ether. The water was removed with anhydrous magnesium sulfate, and hexane was separated from the mobile phase to obtain 5.7 g of 10-bromodecyl-10-phenylanthracene as a green oily phase.
상기 9-(10-bromodecyl)-10-phenylanthracene 2 g, quinolin-3-ylboronic acid 0.88 g, K2CO3(2M) 6.5 ml, Pd(PPh3)4 0.15 g을 톨루엔 20 ml에 녹인 후 환류 교반하였다. 이후 반응이 종결된 후 증류수 및 MC로 추출한 후 감압여과하고 재결정하여 하기 화합물 4 1.43 g을 얻었다. 2 g of 9- (10-bromodecyl) -10-phenylanthracene, 0.88 g of quinolin-3-ylboronic acid, 6.5 ml of K 2 CO 3 (2M) and 0.15 g of Pd (PPh 3 ) 4 were dissolved in 20 ml of toluene, Lt; / RTI > After the reaction was completed, the reaction mixture was extracted with distilled water and MC, filtered under reduced pressure, and recrystallized to obtain 1.43 g of the following compound 4.
m/z: 521.31 (100.0%), 522.31 (43.0%), 523.31 (8.8%), 524.32 (1.2%)m / z: 521.31 (100.0%), 522.31 (43.0%), 523.31 (8.8%), 524.32
[제조예 5][Production Example 5]
quinolin-3-ylboronic acid를 quinolin-8-ylboronic acid로 반응한 것을 제외하고는 제조예 4와 같은 방법으로 화합물 5를 얻었다.quinolin-3-ylboronic acid was reacted with quinolin-8-ylboronic acid, Compound 5 was obtained in the same manner as in Production Example 4.
m/z: 521.31 (100.0%), 522.31 (43.0%), 523.31 (8.8%), 524.32 (1.2%)m / z: 521.31 (100.0%), 522.31 (43.0%), 523.31 (8.8%), 524.32
[제조예 6][Production Example 6]
quinolin-3-ylboronic acid를 B-[4-(1-Phenyl-1H-benzimidazol-2-yl) phenyl]boronic acid로 반응한 것을 제외하고는 제조예 4와 같은 방법으로 화합물 6을 얻었다.Compound 6 was obtained in the same manner as in Production Example 4 except that quinolin-3-ylboronic acid was reacted with B- [4- (1-Phenyl-1H-benzimidazol-2-yl) phenyl] boronic acid.
m/z: 662.37 (100.0%), 663.37 (53.5%), 664.37 (14.2%), 665.38 (2.4%)m / z: 662.37 (100.0%), 663.37 (53.5%), 664.37 (14.2%), 665.38
[제조예 7][Production Example 7]
quinolin-3-ylboronic acid를 Pyrazole-4-boronic acid pinacol ester로 반응한 것을 제외하고는 제조예 4와 같은 방법으로 화합물 7을 얻었다.quinolin-3-ylboronic acid was reacted with pyrazole-4-boronic acid pinacol ester, Compound 7 was obtained in the same manner as in Production Example 4.
m/z: 932.46 (100.0%), 934.46 (97.8%), 935.47 (72.3%), 933.47 (68.9%), 934.47 (23.4%), 936.47 (22.8%), 937.47 (5.1%)m / z: 932.46 (100.0%), 934.46 (97.8%), 935.47 (72.3%), 933.47 (68.9%), 934.47 (23.4%), 936.47 (22.8%
실시예 1 내지 3 (유·무기 발광소자(HOLED) 제조)Examples 1 to 3 (Production of organic / inorganic light emitting device (HOLED)) [
상기 제조된 제조예 1 내지 3의 화합물을 사용하여 도 1과 같은 구조를 가지는 유· 무기 발광소자(HOLED)를 제조하였다. 구체적으로 설명하면 다음과 같다. 인듐틴옥사이드(ITO)가 1500 Å 두께가 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척하고 건조시킨 후 플라즈마 세정기로 이송 시킨 다음 산소 플라즈마를 이용하여 상기 기판을 5분간 세정 한 후 ITO 기판 상부에 전자전달층으로서 산화아연나노입자(ZnO nanoparticle)를 스핀코팅하여 막두께 85 nm 제막하였다. 다음으로 상기 제조예 1 내지 18에서 합성한 화합물을 클로로벤젠에 용해하여 1 wt% 용액으로 조제하고, 스핀 코팅법에 의해 발광층으로 100 nm를 제막하였다. 다음으로 PVK를 클로로벤젠에 용해하여 1 wt% 용액으로 조제하고, 스핀 코팅법에 의해 정공전달층으로 50 nm를 제막하였다. 다음으로 진공증착장치를 이용하여 MoO3를 정공주입층으로 10 nm, 양극으로 Al을 100 nm로 제막하고, 이 소자를 글로브 박스에서 밀봉함으로써 유· 무기 발광소자(HOLED)를 제작하였다.Using the compounds of Preparation Examples 1 to 3 thus prepared, an organic / inorganic light emitting device (HOLED) having the structure shown in FIG. 1 was prepared. Specifically, it is as follows. The glass substrate coated with thin film of indium tin oxide (ITO) 1500 Å in thickness was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, and the substrate was transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then zinc oxide Nanoparticles (ZnO nanoparticle) were spin-coated to a film thickness of 85 nm. Next, the compounds synthesized in Preparation Examples 1 to 18 were dissolved in chlorobenzene to prepare a 1 wt% solution, and 100 nm was formed as a light emitting layer by spin coating. Next, PVK was dissolved in chlorobenzene to prepare a 1 wt% solution, and a film of 50 nm was formed as a hole transport layer by spin coating. Next, MoO 3 was formed into a hole injection layer of 10 nm and an anode of Al was formed of 100 nm using a vacuum evaporation apparatus, and the device was sealed in a glove box to prepare an organic light emitting device (HOLED).
또한 상기 제작된 유기발광소자의 소자 특성을 측정하였다. 일예로 실시예 1 내지 3의 화합물을 사용하여 제조한 유기발광소자는 Keithley- 236 소스-측정 유닛으로 측정시 도 2와 같은 전류 밀도-전압-휘도(I-V-L) 특성, 효율을 나타내었으며, 용액공정을 통한 단분자 재료의 발광을 확인할 수 있었다.The device characteristics of the fabricated organic light emitting device were measured. For example, the organic light-emitting device manufactured using the compounds of Examples 1 to 3 exhibited current density-voltage-luminance (IVL) characteristics and efficiency as measured by a Keithley-236 source-measuring unit, The light emission of monomolecular material could be confirmed.
Claims (22)
[화학식 1]
A-(R a ) n -(R b ) m -D p
상기 식에서,
A는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, 치환되거나 치환되지 않은 C1~C40의 알킬기, C2~C40의 알케닐기, C1~C40의 알콕시기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C6~C40의 아릴기, C3~C40의 헤테로아릴기, 및 Si로 이루어진 군으로부터 선택된 하나 이상의 기로 치환되거나 치환되지 않은 형광 또는 인광 화합물이고;
Ra는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C1~C40의 알콕시기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C6~C40의 아릴기 및 C3~C40의 헤테로아릴기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환되거나 치환되지 않은 Si; C1~C40의 알킬기; C3~C40의 시클로알킬기; C3~C40의 알케닐기; C3~C40의 알콕시기; 아미노기; C6~C40의 아릴기; 또는 C3~C40의 헤테로아릴기이고, 여기서, 인접 고리는 서로 융합될 수 있으며;
Rb는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C1~C40의 알콕시기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C6~C40의 아릴기 및 C3~C40의 헤테로아릴기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환되거나 치환되지 않은 Si; C1~C40의 알킬기; C3~C40의 시클로알킬기; C3~C40의 알케닐기; C3~C40의 알콕시기; 아미노기; C6~C40의 아릴기; 또는 C3~C40의 헤테로아릴기이고, 여기서, 인접 고리는 서로 융합될 수 있고;
D는 하기 화학식 Fg1 내지 Fg14로 표시되는 것 중 하나이며, 여기서 *는 연결부분이며, Fg1 내지 Fg14에 함유된 하나 이상의 수소는 각각 독립적으로 중수소; 할로겐; 아미노기; 니트릴기; 니트로기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환된 치환되거나 치환되지 않은 Si; C1~C40의 알킬기; C3~C40의 시클로알킬기; C3~C40의 알케닐기; C3~C40의 알콕시기; C6~C40의 아릴기; 또는 C3~C40의 헤테로아릴기로 치환될 수 있으며, Rf1은 각각 독립적으로 수소; 중수소; 할로겐; 아미노기; 니트릴기; 니트로기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환된 치환되거나 치환되지 않은 C1~C40의 알킬기; C3~C40의 시클로알킬기; C3~C40의 알케닐기; C3~C40의 알콕시기; C6~C40의 아릴기; 또는 C3~C40의 헤테로아릴기이며;
n 및 m은 각각 독립적으로 0 내지 10의 정수이고,
p는 1 내지 10의 정수이다:
Fg1:
A compound represented by the following formula (1):
[Chemical Formula 1]
A- (R a ) n - (R b ) m -D p
In this formula,
A is a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a substituted or unsubstituted C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 1 ~ C 40 of the alkoxy group, C 3 ~ C 40 Substituted or unsubstituted with at least one group selected from the group consisting of a cycloalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 6 to C 40 aryl group, a C 3 to C 40 heteroaryl group, and Si; A phosphorescent compound;
R a is a group selected from the group consisting of deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 1 to C 40 alkoxy group, a C 3 to C 40 cycloalkyl group, Si substituted or unsubstituted with at least one group selected from the group consisting of C 3 to C 40 heterocycloalkyl groups, C 6 to C 40 aryl groups and C 3 to C 40 heteroaryl groups; A C 1 to C 40 alkyl group; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 alkenyl group; A C 3 to C 40 alkoxy group; An amino group; A C 6 to C 40 aryl group; Or a C 3 to C 40 heteroaryl group, wherein adjacent rings may be fused to each other;
R b is selected from the group consisting of deuterium, halogen, amino, nitrile, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 1 to C 40 alkoxy, C 3 to C 40 cycloalkyl, Si substituted or unsubstituted with at least one group selected from the group consisting of C 3 to C 40 heterocycloalkyl groups, C 6 to C 40 aryl groups and C 3 to C 40 heteroaryl groups; A C 1 to C 40 alkyl group; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 alkenyl group; A C 3 to C 40 alkoxy group; An amino group; A C 6 to C 40 aryl group; Or a C 3 to C 40 heteroaryl group, wherein adjacent rings may be fused to each other;
D is one of the following formulas: Fg1 to Fg14, wherein * is a linking moiety, and at least one hydrogen contained in Fg1 to Fg14 is independently selected from the group consisting of deuterium; halogen; An amino group; A nitrile group; A nitro group; Or substituted or unsubstituted Si substituted by deuterium, halogen, amino, nitrile or nitro; A C 1 to C 40 alkyl group; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 alkenyl group; A C 3 to C 40 alkoxy group; A C 6 to C 40 aryl group; Or a C 3 to C 40 heteroaryl group, and each R f1 is independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; Or a substituted or unsubstituted C 1 to C 40 alkyl group substituted by deuterium, halogen, amino, nitrile or nitro; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 alkenyl group; A C 3 to C 40 alkoxy group; A C 6 to C 40 aryl group; Or a C 3 to C 40 heteroaryl group;
n and m are each independently an integer of 0 to 10,
p is an integer from 1 to 10;
Fg1:
A가 하기 FL1 내지 FL33으로 표시되는 화합물 중 하나인 것을 특징으로 하는 화합물:
FL1:
FL5:
상기 FL1 내지 FL33에서 *는 연결부분이며, R1 내지 R16은 각각 독립적으로 수소; 중수소; 할로겐; 아미노기; 니트릴기; 니트로기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1~C40의 알킬기; C2~C40의 알케닐기; C1~C40의 알콕시기; C3~C40의 시클로알킬기; C3~C40의 헤테로시클로알킬기; C6~C40의 아릴기; C3~C40의 헤테로아릴기; 또는 Si이다.The method according to claim 1,
A is one of the compounds represented by the following formulas FL1 to FL33:
FL1:
FL5:
In the above-mentioned FL1 to FL33, * is a connecting part, and R1 to R16 are each independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro, unsubstituted or substituted with C 1 ~ C 40 alkyl group; A C 2 to C 40 alkenyl group; A C 1 to C 40 alkoxy group; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 heterocycloalkyl group; A C 6 to C 40 aryl group; A C 3 to C 40 heteroaryl group; Or Si.
A가 하기 PL1 내지 PL59 중 하나로 표시되는 것을 특징으로 하는 화합물:
PL1:
상기 PL1 내지 PL59에서 *는 연결부분이며, R1 내지 R16은 각각 독립적으로 수소; 중수소; 할로겐; 아미노기; 니트릴기; 니트로기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1~C40의 알킬기; C2~C40의 알케닐기; C1~C40의 알콕시기; C3~C40의 시클로알킬기; C3~C40의 헤테로시클로알킬기; C6~C40의 아릴기; C3~C40의 헤테로아릴기; 또는 Si이다.The method according to claim 1,
A is represented by one of the following PL1 to PL59:
PL1:
In the above PL1 to PL59, * is a linking moiety, and R1 to R16 each independently represent hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro, unsubstituted or substituted with C 1 ~ C 40 alkyl group; A C 2 to C 40 alkenyl group; A C 1 to C 40 alkoxy group; A C 3 to C 40 cycloalkyl group; A C 3 to C 40 heterocycloalkyl group; A C 6 to C 40 aryl group; A C 3 to C 40 heteroaryl group; Or Si.
A가 안트라센기를 포함하며, Ra 또는 Rb 중 적어도 하나는 C1~C40의 알킬기 또는 C2~C40의 알케닐기인 것을 특징으로 하는 화합물.The method according to claim 1,
Wherein A comprises an anthracene group and at least one of R a or R b is a C 1 to C 40 alkyl group or a C 2 to C 40 alkenyl group.
Ra 또는 Rb가 할로겐, -CF3, 또는 -CN를 포함하는 헤테로 고리 화합물인 것을 특징으로 하는 화합물.The method according to claim 1,
Wherein R a or R b is a heterocyclic compound comprising halogen, -CF 3 , or -CN.
상기 화학식 1의 화합물이 하기 구조식들로 이루어진 군으로부터 선택되는 것을 특징으로 하는 화합물:
Wherein the compound of formula 1 is selected from the group consisting of:
상기 화합물은 발광물질인 것을 특징으로 하는 화합물.The method according to claim 1,
Wherein said compound is a luminescent material.
상기에서 A, Ra, Rb, D는 청구항 1에서 정의한 바와 같으며, X는 할로겐 화합물이다.A process for producing a compound represented by the formula (1), wherein D is bonded to the compound AX, A-Ra-X or A-Ra-Rb-
Wherein A, Ra, Rb and D are as defined in claim 1, and X is a halogen compound.
상기 화합물의 제조방법은 하기 반응식들 중 하나로 표시되는 것을 특징으로 하는 화합물의 제조방법:
상기에서 반응식들에서, A, Ra, Rb, D, Rf1은 청구항 1에서 정의한 바와 같다.9. The method of claim 8,
Wherein the method for preparing the compound is represented by one of the following reaction schemes:
In the above formulas, A, Ra, Rb, D and Rf1 are as defined in claim 1.
상기 발광소자는 HOLED 또는 OLED 소자인 것을 특징으로 하는 발광소자.11. The method of claim 10,
Wherein the light emitting element is a HOLED or an OLED element.
상기 발광소자는 제1항 기재의 화합물을 발광층에 포함하는 것을 특징으로 하는 발광소자.11. The method of claim 10,
Wherein the light emitting element comprises a compound according to any one of claims 1 to 3 in a light emitting layer.
상기 발광소자는 HOLED 소자인 것을 특징으로 하는 발광소자.11. The method of claim 10,
Wherein the light emitting element is a HOLED element.
상기 발광소자는 전극과 발광층 사이에 Zno, TiO2, ZrO2, Ta2O3, MgO 또는 HfO2의 금속산화물로 형성된 전자주입 및 전자수송층을 가지는 것을 특징으로 하는 발광소자.14. The method of claim 13,
Wherein the light emitting element has an electron injecting and electron transporting layer formed between the electrode and the light emitting layer and formed of a metal oxide of Zno, TiO2, ZrO2, Ta2O3, MgO, or HfO2.
상기 발광소자는 전극과 발광층 사이에 P형 금속산화물 또는 유기물층으로 구성된 정공전달 및 정공수송층 가지는 것을 특징으로 하는 발광소자.14. The method of claim 13,
Wherein the light emitting element has a hole transporting and hole transporting layer composed of a P-type metal oxide or an organic material layer between the electrode and the light emitting layer.
상기 유기물층이 제1항 기재의 화합물을 포함하는 것을 특징으로 하는 발광소자의 제조방법.A method of manufacturing a light emitting device for forming an organic material layer including a light emitting layer between an anode and a cathode,
Wherein the organic compound layer comprises a compound according to any one of claims 1 to 5. A method for manufacturing a light-
상기 발광소자는 HOLED 또는 OLED 소자인 것을 특징으로 하는 발광소자의 제조방법.17. The method of claim 16,
Wherein the light emitting device is a HOLED or an OLED device.
상기 발광소자는 제1항 기재의 화합물을 발광층에 포함하는 것을 특징으로 하는 발광소자의 제조방법.17. The method of claim 16,
Wherein the light emitting element comprises the compound of claim 1 in a light emitting layer.
상기 발광소자는 HOLED 소자인 것을 특징으로 하는 발광소자의 제조방법.17. The method of claim 16,
Wherein the light emitting device is a HOLED device.
상기 발광소자는 전극과 발광층 사이에 ZnO, TiO2, ZrO2, Ta2O3, MgO 또는 HfO2의 금속산화물로 형성된 전자주입 및 전자수송층을 가지는 것을 특징으로 하는 발광소자의 제조방법.20. The method of claim 19,
Wherein the light emitting element has an electron injecting and electron transporting layer formed between the electrode and the light emitting layer and formed of a metal oxide of ZnO, TiO 2 , ZrO 2 , Ta 2 O 3 , MgO, or HfO 2 .
상기 제1항 기재의 화학식은 wet process 공정을 통하여 발광소자에 형성되는 것을 특징으로 하는 발광소자의 제조방법.17. The method of claim 16,
The method of claim 1, wherein the chemical formula is formed on the light emitting device through a wet process.
상기 발광소자는 전극과 발광층 사이에 P형 금속산화물 또는 유기물층으로 구성된 정공전달 및 정공수송층 가지는 것을 특징으로 하는 발광소자의 제조방법.17. The method of claim 16,
Wherein the light emitting device has a hole transporting and hole transporting layer composed of a P-type metal oxide or an organic material layer between the electrode and the light emitting layer.
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| US9902687B2 (en) | 2014-09-19 | 2018-02-27 | Idemitsu Kosan Co., Ltd. | Compound |
| CN113072547A (en) * | 2021-03-31 | 2021-07-06 | 广东工业大学 | Compound and triplet-triplet annihilation up-conversion system |
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| US9902687B2 (en) | 2014-09-19 | 2018-02-27 | Idemitsu Kosan Co., Ltd. | Compound |
| US10118889B2 (en) | 2014-09-19 | 2018-11-06 | Idemitsu Kosan Co., Ltd. | Compound |
| US10435350B2 (en) | 2014-09-19 | 2019-10-08 | Idemitsu Kosan Co., Ltd. | Organic electroluminecence device |
| CN113072547A (en) * | 2021-03-31 | 2021-07-06 | 广东工业大学 | Compound and triplet-triplet annihilation up-conversion system |
| CN113072547B (en) * | 2021-03-31 | 2022-10-21 | 广东工业大学 | A compound and triplet-triplet annihilation upconversion system |
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