WO2009005272A2 - Composés complexes organométalliques pour afficheur électroluminescent organique, et afficheur électroluminescent renfermant ces composés - Google Patents

Composés complexes organométalliques pour afficheur électroluminescent organique, et afficheur électroluminescent renfermant ces composés Download PDF

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WO2009005272A2
WO2009005272A2 PCT/KR2008/003826 KR2008003826W WO2009005272A2 WO 2009005272 A2 WO2009005272 A2 WO 2009005272A2 KR 2008003826 W KR2008003826 W KR 2008003826W WO 2009005272 A2 WO2009005272 A2 WO 2009005272A2
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substituted
light emitting
carbon number
unsubstituted
display device
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WO2009005272A3 (fr
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Hyung-Sun Kim
Ho-Jae Lee
Eun-Sun Yu
Nam-Soo Kim
Young-Hoon Kim
Mi-Young Chae
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Cheil Industries Inc.
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Publication of WO2009005272A3 publication Critical patent/WO2009005272A3/fr

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    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3

Definitions

  • the present invention relates to a metallic complex compound for an organic light emitting display device, and an organic light emitting display device including the same for a light emitting dopant. More particularly, the present invention relates to a metallic complex compound that is an emission-layer-forming material for an organic light emitting display device, and an organic light emitting display device including the same for a light emitting dopant.
  • An organic light emitting display device is a self light emitting display device that can be driven at a low voltage, and has a wide viewing angle, good contrast, and fast response speed. It can also be lightweight and thin since it does not need a backlight.
  • the organic layer has a structure in which a thin film (hole transport layer (HTL)) of a diamine derivative and a thin film of tris(8-hydroxy-quinolate)aluminum (AIq 3 ) are laminated.
  • HTL hole transport layer
  • an light emitting display device is composed of an anode of a transparent electrode, an organic thin layer of a light emitting region, and a metal electrode (cathode) formed on a glass substrate, in that order.
  • the organic thin layer may include an emission layer, a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), and an electron injection layer (EIL). It may further include an electron inhibition layer or a hole inhibition layer due to the emission characteristics of the emission layer.
  • HIL hole injection layer
  • HTL hole transport layer
  • ETL electron transport layer
  • EIL electron injection layer
  • the light emitting display device is applied with an electric field, and the holes and electrons are injected from the anode and the cathode, respectively.
  • the injected holes and electrons are recombined on the emission layer though the hole transport layer (HTL) and the electron transport layer (ETL) to provide light emitting excitons.
  • the provided light emitting excitons emit light by transiting to the ground state.
  • a light emitting colorant doped to an emission layer (host) to increase light emitting efficiency and stability.
  • light emitting materials may be classified as a fluorescent material including singlet excitons and a phosphorescent material including triplet excitons according to the light emitting mechanism.
  • Such a phosphorescent material emits light by transiting electrons from a ground state to an exited state, non-radiance transiting of a singlet exciton to a triplet exciton through intersystem crossing, and transiting a triplet exciton to a ground state to emit light.
  • the electron spin is flipped and then it is transited to the ground state, so that it provides a characteristic of extending the lifetime (emission duration) to more than that of fluorescent emission.
  • the duration of fluorescent emission is extremely short at several nanoseconds, but the duration of phosphorescent emission is relatively long such as at several microseconds.
  • the percentage of the singlet exited state is 25% (the triplet is 75%) in the case of a fluorescent material, so it has limits in luminous efficiency.
  • a phosphorescent material in the case of a phosphorescent material, it can utilize 75% of the triplet exited state and 25% of the singlet exited state, so theoretically the internal quantum efficiency can reach up to 100%.
  • a phosphorescent light emitting material when used, it has advantages in an increase in luminous efficiency of around four times that of the fluorescent light emitting material.
  • a phosphorescent light emitting material has a molecule structure appropriate for intersystem crossing.
  • the molecule structure includes heavy metals such as Ir, Pt, Rh, or Pd in an organic molecule, which incurs spin-orbital coupling and thus triplets and singlets are mixed. Thereby, inhibited transition is allowed and phosphorescent light emission at room temperature can effectively occur.
  • Such an organic metallic complex for phosphorescent light emission is a low molecular material that is applicable using a general dry process such as vacuum deposition.
  • a general dry process such as vacuum deposition.
  • a polymer material it can be applied to a device using a wet process such as spin coating, InkJet printing, or casting.
  • a metallic complex compound for an organic light emitting display device that has improved solubility due to bulky substituents, and is therefore applied using a wet process such as spin coating, InkJet printing, or casting during manufacture of a device.
  • an organic light emitting display device including the metallic complex compound.
  • the metallic complex compound for an organic light emitting display device includes a symmetric fluorene derivative ligand represented by the following Formula 1:
  • n is an integer ranging from 1 to 3, and a and b are independently 0 or 1;
  • the above cycle of Formula 1 may be a cycle including a double bond or a single bond
  • M is a metal to form an octahedral complex
  • L is a didentate ligand of a monovalent anion bound to M through a coordinate covalent bond with an sp 2 carbon and a heteroatom, or a didentate ligand of a monovalent anion bound to M through a coordinate covalent bond with a heteroatom and an unshared electron pair of a heteroatom;
  • Y 1 is a monodentate ligand bound to M through a coordinate covalent bond with an unshared electron pair of heteroatom
  • Y 2 is a monodentate ligand bound to M through a coordinate covalent bond with an sp 2 carbon and nitrogen atom of a monovalent anion
  • X 1 to X 8 are carbon atoms or heteroatoms, and when one of X 1 to X 8 is a carbon atom, R 1 to R 8 bound to X 1 to X 8 are substituents bound to the carbon atom, or
  • R 1 to R 8 are independently selected from the group consisting of hydrogen, a substituted or unsubstituted aryl having a carbon number of 6 or more, a substituted or un- substituted heteroaryl having a carbon number of 2 or more, a substituted or unsubstituted alkyl having a carbon number of 1 or more, a substituted or unsubstituted amino having a carbon number of 2 or more, a substituted or unsubstituted alkoxy having a carbon number of 1 or more, a halogen, a nitro, a substituted or unsubstituted arylene having a carbon number of 6 or more, a substituted or unsubstituted het- eroarylene having a carbon number of 2 or more, and a substituted or unsubstituted alkylene having a carbon number of 1 or more.
  • the compound of the above Formula 1 is an aromatic cyclic compound.
  • the metal (M) to form an octahedral complex is iridium.
  • R 1 to R 8 may have a fluorene structure selected from the group consisting of the following Formulae 2 and 3:
  • R 9 is independently one selected from the group consisting of hydrogen, a halogen, R", OR 4 , N(R 11 K P(R 11 K P(OR 11 K POR 11 , PO 2 R 11 , PO 3 R 11 , SR 11 , Si(R 11 K Si(CHs) 2 R 11 , Si(Ph) 2 R 11 , B(R 11 K B(OR 11 K C(O)R 11 , C(O)OR 11 , C(O)N(R 11 K CN, NO 2 , SO 2 , SOR 11 , SO 2 R 11 , and SO 3 R 11 ;
  • R 11 is selected from the group consisting of hydrogen, a linear or branched Cl to C30 alkyl, a linear or branched C2 to C30 alkenyl, a linear or branched C2 to C30 alkynyl, a linear or branched Cl to C30 heteroalkyl, a C6 to C40 aryl, and a C3 to C40 heteroaryl, wherein R 11 is substituted with at least one substituent, Z;
  • Z is selected from the group consisting of R 12 , OR 12 , N(R 12 K P(R 12 K P(OR 12 K POR i2, PO 2 R 12 , PO 3 R 12 , SR 12 , Si(R 12 K Si(CH 3 ) 2 R 12 , Si(Ph) 2 R 12 , B(R 12 K B(OR 12 K C(O)R 12 , C(O)OR 12 , C(O)N(R 12 K CN, NO 2 , SO 2 , SOR 12 , SO 2 R 12 , and SO 3 R 12 ;
  • R 12 is selected from the group consisting of hydrogen, a linear or branched Cl to C30 alkyl, a linear or branched C2 to C30 alkenyl, a linear or branched C2 to C30 alkynyl, a linear or branched Cl to C30 heteroalkyl, a C6 to C40 aryl, and a C3 to C40 heteroaryl; and
  • R 10 is selected from the group consisting of a substituted or unsubstituted aryl having a carbon number of 6 or more, a substituted or unsubstituted heteroaryl having a carbon number of 2 or more, a substituted or unsubstituted alkyl having a carbon number of 1 or more, a substituted or unsubstituted amino having a carbon number of 2 or more, a substituted or unsubstituted alkoxy having a carbon number of 1 or more, a halogen, a nitro, a substituted or unsubstituted arylene having a carbon number of 6 or more, a substituted or unsubstituted heteroarylene having a carbon number of 2 or more, and a substituted or unsubstituted alkylene having a carbon number of 1 or more.
  • L is a ligand selected from the group consisting of the following lignads (1) to (9):
  • the metallic complex compound of the above Formula 1 for an organic light emitting display device may be a compound selected from the group consisting of the following Formulae Ia to Ig, but is not limited thereto.
  • the organic light emitting display device includes a first electrode disposed on a substrate, an organic thin layer including the metallic complex compound disposed on the first electrode, and a second electrode disposed on the organic thin layer.
  • the organic thin layer includes at least one of a first buffer layer for hole injection or transport, disposed on the first electrode layer, an emission layer disposed on the first buffer layer, and a second buffer layer for electron injection or transport, disposed on the emission layer.
  • the first electrode is formed of a transparent conductive metal oxide selected from the group consisting of ITO (indium tin oxide), IZO (indium zinc oxide), tin oxide, zinc oxide, and combinations thereof.
  • the substrate may be a glass substrate or a flexible substrate.
  • the emission layer may be formed using at least one of spin coating, InkJet printing, and casting.
  • the metallic complex compound for an organic light emitting display device inhibits molecular mutual interaction by introducing bulky substituents as a ligand, resulting in improvement of solubility.
  • FIG. 1 is a view of an organic light emitting display device according to one embodiment of the present invention. Best Mode for Carrying Out the Invention
  • aryl or "arylene refers to a C6 to C40 aryl or arylene
  • heteroaryl or “heteroarylene” refers to a C2 to C40 heteroaryl or heteroarylene
  • alkyl refers to a Cl to C30 alkyl, alkylene, or alkoxy
  • heteroalkyl refers to a Cl to C30 heteroalkyl.
  • substituted refers to one substituted with at least a substituent selected from the group consisting of an aryl, a heteroaryl, an alkyl, an amino, an alkoxy, a halogen (F, Cl, Br, or I), and a nitro.
  • hetero refers to one including 1 to 10 heteroatoms selected from the group consisting of N, O, S, and Si.
  • the metallic complex compound for an organic light emitting display device includes an asymmetric fluorene derivative ligand represented by the following Formula 1:
  • n is an integer ranging from 1 to 3, and a and b are independently 0 or 1; [79] the above cycle of Formula 1 may be a cycle including a double bond or a single bond; [80] M is a metal to form an octahedral complex;
  • L is a didentate ligand of a monovalent anion bound to M through a coordinate covalent bond with an sp 2 carbon and a heteroatom, or a didentate ligand of a monovalent anion bound to M through a coordinate covalent bond with a heteroatom and an unshared electron pair of a heteroatom;
  • Y 1 is a monodentate ligand bound to M through a coordinate covalent bond with an unshared electron pair of a heteroatom
  • Y 2 is a monodentate ligand bound to M through a coordinate covalent bond with an sp 2 carbon and nitrogen atom of a monovalent anion
  • X 1 to X 8 are a carbon atom or a heteroatom, and when one of X 1 to X 8 is a carbon atom, R 1 to R 8 bound to X 1 to X 8 are substituents bound to the carbon atom, or
  • R 1 to R 8 are independently selected from the group consisting of hydrogen, a substituted or unsubstituted aryl having a carbon number of 6 or more, a substituted or un- substituted heteroaryl having a carbon number of 2 or more, a substituted or unsubstituted alkyl having a carbon number of 1 or more, a substituted or unsubstituted amino having a carbon number of 2 or more, a substituted or unsubstituted alkoxy having a carbon number of 1 or more, a halogen, a nitro, a substituted or unsubstituted arylene having a carbon number of 6 or more, a substituted or unsubstituted het- eroarylene having a carbon number of 2 or more, and a substituted or unsubstituted alkylene having a carbon number of 1 or more.
  • the compound of the above Formula 1 is an aromatic cyclic compound.
  • the metal (M) to form an octahedral complex is iridium.
  • R 1 to R 8 may have a fluorene structure selected from the group consisting of the following Formulae 2 and 3:
  • R 9 isindependently one selected from the group consisting of hydrogen, a halogen, R", OR 4 , N(R 11 K P(R 11 K P(OR 11 K POR 11 , PO 2 R 11 , PO 3 R 11 , SR 11 , Si(R 11 K Si(CHs) 2 R 11 , Si(Ph) 2 R 11 , B(R 11 K B(OR 11 K C(O)R 11 , C(O)OR 11 , C(O)N(R 11 ),, CN, NO 2 , SO 2 , SOR 11 , SO 2 R 11 , and SO 3 R 11 ;
  • R 11 is selected from the group consisting of hydrogen, a linear or branched Cl to C30 alkyl, a linear or branched C2 to C30 alkenyl, a linear or branched C2 to C30 alkynyl, a linear or branched Cl to C30 heteroalkyl, a C6 to C40 aryl, and a C6 to C40 heteroaryl, wherein R 11 is substituted with at least one substituent, Z;
  • Z is selected from the group consisting of R 12 , OR 12 , N(R 12 ) 2 , P(R 12 ) 2 , P(OR 12 ) 2 , POR i2, PO 2 R 12 , PO 3 R 12 , SR 12 , Si(R 12 ) 3 , Si(CH 3 ) 2 R 12 , Si(Ph) 2 R 12 , B(R 12 ) 2 , B(OR 12 K C(O)R 12 , C(O)OR 12 , C(O)N(R 12 K CN, NO 2 , SO 2 , SOR 12 , SO 2 R 12 , and SO 3 R 12 ;
  • R 12 is selected from the group consisting of hydrogen, a linear or branched Cl to C30 alkyl, a linear or branched C2 to C30 alkenyl, a linear or branched C2 to C30 alkynyl, a linear or branched Cl to C30 heteroalkyl, a C6 to C40 aryl, and a C3 to C40 heteroaryl; and
  • R 10 is selected from the group consisting of a substituted or unsubstituted aryl having a carbon number of 6 or more, a substituted or unsubstituted heteroaryl having a carbon number of 2 or more, a substituted or unsubstituted alkyl having a carbon number of 1 or more, a substituted or unsubstituted amino having a carbon number of 2 or more, a substituted or unsubstituted alkoxy having a carbon number of 1 or more, a halogen, a nitro, a substituted or unsubstituted arylene having a carbon number of 6 or more, a substituted or unsubstituted heteroarylene having a carbon number of 2 or more, and a substituted or unsubstituted alkylene having a carbon number of 1 or more.
  • L is a ligand selected from the group consisting of the following lignads (1) to (9):
  • the metallic complex compound of the above Formula 1 for an organic light emitting display device may be a compound selected from the group consisting of the following Formulae Ia to Ig, but is not limited thereto.
  • R and R' are a linear or branched Cl to C30 alkyl and M is a metal to form an octahedral complex.
  • the above metallic complex compound can be applied as a light emitting dopant of an organic light emitting display device.
  • FIG. 1 is a view of organic light emitting display device according to one embodiment of the present invention.
  • the organic light emitting display device 1 includes a first electrode (anode, 20) disposed on a substrate 10, an organic thin layer 100 including the metallic complex compound disposed on the first electrode, and a second electrode (cathode, 30) disposed on the organic thin layer 100.
  • the organic thin layer 100 includes at least one of a first buffer layer 110 for hole injection or transport, disposed on the first electrode 20, an emission layer 120 disposed on the first buffer layer 110, and a second buffer layer 130 for electron injection or transport, disposed on the emission layer 120. At least one layer of the organic thin layer 100 includes the metallic complex compound according to one embodiment of the present invention.
  • the first buffer layer 110 may include at least one selected from the group consisting of a hole injection layer (HIL) and a hole transport layer (HTL), and may further include an electron inhibition layer to improve light emitting characteristics of the emission layer 120.
  • HIL hole injection layer
  • HTL hole transport layer
  • the second buffer layer 130 may include at least one selected from the group consisting of an electron injection layer (EIL) and an electron transport layer (ETL), and may further include a hole inhibition layer to improve light emitting characteristics of the emission layer 120.
  • EIL electron injection layer
  • ETL electron transport layer
  • a third buffer layer (not shown) may be disposed between the first electrode 20 and the first buffer layer 120 to complement an anode surface and help hole injection and flow.
  • the third buffer layer may include a polymer such as doped poly aniline (PANI) or doped polyethylene dioxythiophene (PEDOT), or a low molecular material such as alpha-CuPc.
  • PANI doped poly aniline
  • PEDOT doped polyethylene dioxythiophene
  • alpha-CuPc low molecular material
  • the first electrode 20 is formed of a transparent conductive metal oxide selected from the group consisting of ITO (indium tin oxide), IZO (indium zinc oxide), tin oxide, zinc oxide, and combinations thereof.
  • the substrate 10 may be a glass substrate or a flexible substrate.
  • the emission layer 120 is formed of a host and a dopant using a wet process such as spin coating, InkJet printing, or casting.
  • the host may be TMM038 (Merck, low molecule), PVK (polyvinyl carbazole), or PVK/CBP (4,4'-N,N'-dicarbazolebiphenyl) (45:55 or 1:1 weight ratio), and the dopant is the metallic complex compound according to one embodiment of the present invention.
  • the metallic complex compound may be included in an amount of 1 to 30 wt% based on the total weight of emission layer materials. In one embodiment, the metallic complex compound may be included in an amount of 3 to 10 wt% based on the total weight of emission layer materials. Within the above range, preferable device characteristics can be obtained.
  • the holes and electrons are injected from the first electrode 20 and the second electrode 30, respectively.
  • the injected holes and electrons are recombined on the emission layer though the hole transport layer (HTL) and the electron transport layer (ETL) to provide light emitting excitons.
  • HTL hole transport layer
  • ETL electron transport layer
  • ligand a was synthesized using a Suzuki coupling reaction. 2g (leq, 4 mmol) of the intermediate 3 and 0.59g (0.9 eq, 3.6 mmol) of 1-chloroisoquinoline were dissolved in 10ml of a 2M potassium carbonate aqueous solution and 20ml of THF. Then, O.lg (2 mol%) tetrakis(triphenylphosphine)palladiumwith an oxidation number of 0 was added thereto under a nitrogen flow and refluxed for 12 hours.
  • Example 2 Synthesis of Chemical Formula 1 b'
  • the intermediate 3 in Example 1 was reacted with l-(4'-bromophenyl)isoquinoline to synthesize the corresponding ligand b using a Suzuki coupling reaction.
  • the compound of the following formula Ib' was obtained using the ligand according to the same method as in Example 1.
  • Example 3 Synthesis of Chemical Formula 1 c' [150] The intermediate 3 in Example 1 was reacted with l-(3'-bromophenyl)isoquinoline to synthesize the corresponding ligand c using a Suzuki coupling reaction. The compound of the following formula Ic' was obtained using the ligand according to the same method as in Example 1.
  • Example 4 Synthesis of Chemical Formula 1 d' [154] The intermediate 4 having the following formula was reacted with l-(4'-bromophenyl)isoquinoline to synthesize the corresponding ligand d using a Suzuki coupling reaction. The compound of the following formula Id' was obtained using the ligand according to the same method as in Example 1.
  • Example 5 Synthesis of Chemical Formula 1 e' [160] The intermediate 3 in Example 1 was reacted with 4-bromophenylpyridine to synthesize the corresponding ligand e using a Suzuki coupling reaction. The compound of the following formula Ie' was obtained using the ligand according to the same method as in Example 1.
  • Ligand f was prepared according to a similar process to Example 1. 0.3 g (2 eq, 0.66 mmol) of the ligand f and 0.2g (0.33 mmol) of Ir(ppy) 2 (acac) were dissolved in glycerol. The resulting product was heated to 200 0 C for 24 hours under a nitrogen flow, and then agitated.
  • Ligand g was prepared according to a similar process to Example 1. 0.65g (2 eq, 0.66 mmol) of the ligand g and 0.2g (0.33 mmol) of Ir(ppy) 2 (acac) were dissolved in glycerol. The resulting product was heated to 200 0 C for 24 hours under a nitrogen flow, and then agitated.
  • a first electrode 20 was fabricated to have a size of 20mm x 20mm x 0.7mm on a 15 ⁇ /cm 2 1200A substrate 10 (Corning Inc.).
  • the first electrode 20 included ITO (indium tin oxide) as a transparent conductive metal oxide.
  • the substrate 10 including the first electrode 20 was ultrasonic wave cleaned in isopropyl alcohol and pure water for 5 minutes, and then UV ozone cleaned for 30 minutes.
  • the first electrode 20 was coated on the top thereof to form an organic thin layer 100 by spin-coating PEDOT (poly (e thy lenedioxy)thiophene).
  • an emission layer was spin-coated to be 500A thick on the PEDOT (poly(ethylenedioxy)thiophene) by using TMM038 (Merck, low molecular) as a host and the metallic complex compounds Ia' to Id' according to Examples 1 to 4 as a dopant (7wt% based on the total amount of the host and dopant).
  • PEDOT poly(ethylenedioxy)thiophene
  • TMM038 Merck, low molecular
  • BAIq was vacuum-deposited to form a 50A-thick hole inhibition layer on the emission layer 120.
  • Alq3 was vacuum-deposited to form a 200A-thick electron transport layer (ETL) on the hole inhibition layer.
  • ETL electron transport layer
  • LiF at 1OA for an electron injection layer (EIL) and Al at 1000 A (cathode) were sequentially vacuum-deposited on the electron transport layer (ETL) to form the second electrode 30 with a LiF/Al metal, fabricating an organic light emitting display device 1.
  • An organic light emitting display device 1 shown in FIG. 1 was fabricated according to the same method as in Example 8, except that an emission layer was spin-coated to be 500 A thick on the PEDOT (poly(ethylenedioxy)thiophene) by using PVK/CBP (4,4'-N,N'-dicarbazolebiphenyl) (1:1 weight ratio) as a host and the metallic complex compounds Ie' to Ig' according to Examples 5 to 7 as a dopant (7wt% based on the total amount of the host and dopant).
  • PEDOT poly(ethylenedioxy)thiophene
  • PVK/CBP 4,4'-N,N'-dicarbazolebiphenyl
  • the organic light emitting display devices 1 according to Examples 8 and 9 were evaluated by measuring initial driving voltage (turn-on voltage), driving voltage (V) at each of maximum luminance (cd/m 2 ) and luminance of 1000 cd/m 2 , current efficiency (cd/A), and electric power efficiency (ImAV). The results of Example 8 are shown in Table 1.
  • the metallic complex compound according to one embodiment of the present invention included in the organic thin layer 100 was fabricated into an organic light emitting display device 1 not by vacuum deposition but by spin coating, which is a wet process.
  • the device can be easily fabricated in a wet process by using the metallic complex compound with excellent solubility due to decreased van der Waals' force among molecules in an organic solvent such as toluene, chloroform, chlorobenzene, and the like, unlike Ir(piq) 3 or Ir(piq) 2 (acac) that are known to have excellent effects among metallic complex compounds emitting red phosphorescent light.
  • the metallic complex compound when a bulky substituent is introduced into a metallic complex compound of the present invention, the metallic complex compound can improve solubility since molecules therein become apart from one another, decreasing crys- tallinity. The molecules have suppressed interaction, resulting in improving luminous efficiency and electrical characteristics.
  • the metallic complex compound of the present invention can be usefully applied as a phosphorescent light emitting material of an organic light emitting display device.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Un composé complexe métallique pour un afficheur électroluminescent organique comprend un ligand dérivé d'un fluorène asymétrique. Le composé complexe métallique pour afficheur électroluminescent organique présente une solubilité améliorée, due aux substituants volumineux, et forme en conséquence une couche mince au moyen d'un processus par voie humide, tel que dépôt à la tournette, impression par jet d'encre, ou coulée durant la fabrication d'un dispositif. En outre, le composé complexe métallique permet de réduire de coût de fabrication d'un afficheur électroluminescent organique et d'améliorer le rendement lumineux, du fait que les substituants volumineux inhibent l'interaction mutuelle moléculaire.
PCT/KR2008/003826 2007-06-29 2008-06-30 Composés complexes organométalliques pour afficheur électroluminescent organique, et afficheur électroluminescent renfermant ces composés WO2009005272A2 (fr)

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WO2013045402A1 (fr) * 2011-09-28 2013-04-04 Solvay Sa Matériau photoémetteur
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JP2018048181A (ja) * 2009-05-29 2018-03-29 株式会社半導体エネルギー研究所 化合物

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US9882149B2 (en) 2012-07-04 2018-01-30 Samsung Sdi Co., Ltd. Compound for organic optoelectric device, organic optoelectronic device comprsing same, and display apparatus comprising organic optoelectric device

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EP1591511A2 (fr) * 2004-04-28 2005-11-02 JSR Corporation Polymère phosphorescent et son procédéde de production, dispositif electroluminescent organique, et composé contenant un complexe métallique et son procédé de production
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JP2018048181A (ja) * 2009-05-29 2018-03-29 株式会社半導体エネルギー研究所 化合物
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KR100907564B1 (ko) 2009-07-14

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