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Researchers Submit Patent Application, "Organometallic Complexes, and Organic Electroluminescent Device and Display Using the Same", for Approval

July 3, 2014



By a News Reporter-Staff News Editor at Politics & Government Week -- From Washington, D.C., VerticalNews journalists report that a patent application by the inventors NOH, Chang Ho (Suwon-si, KR); KWON, O Hyun (Yongin-si, KR); RUPASREE, Ragini Das (Suwon-si, KR); KRAVCHUK, Dmitry (Hwaseong-si, KR); CHOI, Hyeon Ho (Seoul, KR), filed on June 19, 2013, was made available online on June 19, 2014.

No assignee for this patent application has been made.

News editors obtained the following quote from the background information supplied by the inventors: "An organometallic complex, an organic electroluminescent device, and a display device using the same are disclosed.

"An organic electroluminescent device is a display element that actively emits light when a current flows into a fluorescent or phosphorescent organic compound thin layer (hereinafter, an organic layer) in such a way that electrons and holes are combined in the organic layer. The organic electroluminescent device usually has light weight, consists of simple parts, has a simple structure for manufacturing, and secures high image quality and a wide viewing angle. In addition, the organic electroluminescent device may perfectly realize high color purity and a motion picture, and has appropriate electrical characteristics of low power consumption and low voltage driving for a portable electronic device.

"In general, the organic electroluminescent device includes an anode disposed on a substrate, and a hole transport layer ('HTL'), an emission layer, an electron transport layer ('ETL'), and a cathode sequentially formed on the anode. Herein, the hole transport layer ('HTL'), the emission layer, and the electron transport layer ('ETL') are organic layers formed of an organic compound. The organic electroluminescent device is operated as follows. When a voltage is applied between the anode and the cathode, holes injected from the anode pass through the hole transport layer ('HTL') and move toward the emission layer. On the other hand, electrons pass through the electron transport layer ('ETL') from the cathode and are injected into the emission layer, in which the carriers are recombined and produce exitons. The exitons are radioactively decayed and emit light with a wavelength corresponding to the band gap of a used material.

"The emission layer may be formed of a phosphor material using singlet exitons and a phosphorescent material using triplet exitons depending on a light emitting mechanism thereof. The phosphor material or phosphorescent material itself doped on an appropriate host material may be used to form the emission layer. When electrons are excited, singlet and triplet exitons are formed on the host material. Herein, the singlet and triplet exitons are produced in a ratio of about 1:3.

"When the phosphor material is used as an emission layer-forming material, an organic electroluminescent device wastes triplet exitons produced from a host material. However, when the phosphorescent material is used as the emission layer-forming material, both singlet and triplet exitons may be used to reach 100% internal quantum efficiency. Accordingly, the phosphorescent material may have higher luminous efficiency than the phosphor material.

"On the other hand, when a heavy metal such as Ir, Pt, Rh, and Pd is introduced into an organic molecule, the singlet and triplet exitons are spin-orbitally coupled and mixed due to heavy atom effects, and are thus transferred and effectively become phosphorescent even at room temperature.

"As mentioned above, various materials using a transition element compound including a transition element such as iridium, platinum, and the like have been reported as a phosphorescent light emitting material with high efficiency. However, a more highly-efficient phosphorescent material for a full color display element still needs to be developed."

As a supplement to the background information on this patent application, VerticalNews correspondents also obtained the inventors' summary information for this patent application: "An embodiment provides an organometallic complex that efficiently emits light.

"Another embodiment provides an organic electroluminescent device using the organometallic complex.

"Yet another embodiment provides a display device including the organic electroluminescent device.

"According to an embodiment, an organometallic complex represented by Chemical Formula 1 is provided.

"##STR00002##

"In Chemical Formula 1,

"M is Ir, Os, Pt, Pb, Re, Ru, or Pd,

"CyN is

"a substituted or unsubstituted C2 to C60 heterocyclic group wherein nitrogen is bonded to M, or

"a substituted or unsubstituted C3 to C60 heteroaryl group wherein nitrogen is bonded to M,

"CyC is

"a substituted or unsubstituted C4 to C60 carbon cyclic group wherein carbon is bonded to M,

"a substituted or unsubstituted C3 to C60 heterocyclic group wherein carbon is bonded to M,

"a substituted or unsubstituted C3 to C60 heterocyclic group wherein nitrogen is bonded to M,

"a substituted or unsubstituted C3 to C60 aryl group wherein carbon is bonded to M,

"a substituted or unsubstituted C3 to C60 heteroaryl group wherein carbon is bonded to M,

"a substituted or unsubstituted C3 to C60 heteroaryl group wherein nitrogen is bonded to M, or

"a carboxy group wherein oxygen is bonded to M,

"CyN-CyC is a cyclometalating ligand bonded to M through nitrogen, oxygen, or carbon,

"X.sup.1 and X.sup.2 are each independently N or CR',

"R.sup.1 to R.sup.4 and R' are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkoxy group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 heteroaryloxy group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF.sub.5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group,

"wherein R.sup.3 and R.sup.4 are optionally connected to form a fused ring, and

"n is an integer ranging from 0 to 2.

"The organometallic complex may be represented by Chemical Formula 2.

"##STR00003##

"In Chemical Formula 2,

"M is Ir, Os, Pt, Pb, Re, Ru, or Pd,

"CyN is

"a substituted or unsubstituted C2 to C60 heterocyclic group wherein nitrogen is bonded to M, or

"a substituted or unsubstituted C3 to C60 heteroaryl group wherein nitrogen is bonded to M,

"CyC is

"a substituted or unsubstituted C4 to C60 carbon cyclic group wherein carbon is bonded to M,

"a substituted or unsubstituted C3 to C60 heterocyclic group wherein carbon is bonded to M,

"a substituted or unsubstituted C3 to C60 heterocyclic group wherein nitrogen is bonded to M,

"a substituted or unsubstituted C3 to C60 aryl group wherein carbon is bonded to M,

"a substituted or unsubstituted C3 to C60 heteroaryl group wherein carbon is bonded to M,

"a substituted or unsubstituted C3 to C60 heteroaryl group wherein nitrogen is bonded to M, or

"a carboxy group wherein oxygen is bonded to M.

"CyN-CyC is a cyclometalating ligand bonded to M through nitrogen, oxygen, and carbon,

"X.sup.1 and X.sup.2 are each independently N or CR',

"R.sup.1 to R.sup.4 and R' are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkoxy group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 heteroaryloxy group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF.sub.5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group, and

"n is an integer ranging from 0 to 2.

"The cyclometalating ligand may be represented by Chemical Formula S-1.

"##STR00004##

"In Chemical Formula S-1,

"X.sup.1 to X.sup.3 are each independently N or CR', provided that at least one of X.sup.1 to X.sup.3 is N,

"R.sup.1 to R.sup.3 and R' are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkoxy group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 heteroaryloxy group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF.sub.5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group,

"wherein at least two of R.sup.1 to R.sup.3 are optionally connected to form a fused ring, and

"* indicates a binding position to M of Chemical Formula 1.

"The cyclometalating ligand may be represented by Chemical Formula S-2:

"##STR00005##

"In Chemical Formula S-2,

"X.sup.1 to X.sup.3 are each independently N or CR', provided that at least one of X.sup.1 to X.sup.3 is N,

"R.sup.1 to R.sup.3 and R' are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkoxy group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 heteroaryloxy group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF.sub.5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group,

"wherein at least two of R.sup.1 to R.sup.3 are optionally connected to form a fused ring, and

"* indicates a binding position with M of Chemical Formula 1.

"The cyclometalating ligand may be represented by the following Chemical Formula S-3.

"##STR00006##

"In Chemical Formula S-3,

"X.sup.1 to X.sup.3 are independently N or CR', provided that at least one of X.sup.1 to X.sup.3 is N,

"R.sup.1 to R.sup.3 and R' are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkoxy group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 heteroaryloxy group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF.sub.5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group, and

"* indicates a binding position to M of Chemical Formula 1.

"The cyclometalating ligand may be represented by Chemical Formula S-4.

"##STR00007##

"In Chemical Formula S-4,

"R.sup.1 to R.sup.4 are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkoxy group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 heteroaryloxy group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF.sub.5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group, or two adjacent substituents of R.sup.1 to R.sup.4 are fused to form a fused ring, and

"* indicates a binding position to M of Chemical Formula 1.

"The cyclometalating ligand may be represented by Chemical Formula S-5.

"##STR00008##

"In Chemical Formula S-5,

"R.sup.1 to R.sup.7 are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkoxy group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 heteroaryloxy group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF.sub.5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group, and

"* indicates a binding position with M of the above Chemical Formula 1.

"The cyclometalating ligand may be one of the following chemical formulae.

"##STR00009## ##STR00010## ##STR00011##

"In the chemical formulae, R.sup.11, R.sup.12, R.sup.13, R.sup.14, and R.sup.15 are each independently a monosubstituted or multisubstituted functional group, and are each independently hydrogen, a halogen, --OR, --N.sub.2, --P.sub.2, --P(O).sub.2, --P(O)(OR).sub.2, --P(OR).sub.2, --SR, --Si.sub.3, --B.sub.2, --B(OR).sub.2, --C(O)R, --C(O)OR, --C(O)N, --CN, --NO.sub.2, --S(O)R, --S(O).sub.2R, --S(O).sub.2(OR), a C1 to C20 alkyl group, or a C6 to C20 aryl group,

"wherein R is hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C6 to C40 aryl group, a substituted or unsubstituted C7 to C40 arylalkyl group, a substituted or unsubstituted C7 to C40 alkylaryl group, a substituted or unsubstituted C2 to C40 heteroaryl group, or a substituted or unsubstituted C3 to C40 heteroarylalkyl group,

"Z is S, O, or NR.sup.0 (wherein R.sup.0 is hydrogen or a C1 to C20 alkyl group), and

"* indicates a binding position with M of Chemical Formula 1.

"The cyclometalating ligand may be one of chemical formulae.

"##STR00012## ##STR00013## ##STR00014##

"In the chemical formulae,

"R.sub.21, R.sub.22, and R.sub.23 are each independently a monosubstituted or multisubstituted functional group, and are each independently hydrogen, a halogen atom, --OR, --N.sub.2, --P.sub.2, --P(O).sub.2, --P(O)(OR).sub.2, --P(OR).sub.2, --SR, --Si.sub.3, --B.sub.2, --B(OR).sub.2, --C(O)R, --C(O)OR, --C(O)N, --CN, --NO.sub.2, --S(O)R, --S(O).sub.2R, --S(O).sub.2(OR), a C1 to C20 alkyl group, or a C6 to C20 aryl group,

"wherein R is hydrogen, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C6 to C40 aryl group, a substituted or unsubstituted C7 to C40 arylalkyl group, a substituted or unsubstituted C7 to C40 alkylaryl group, a substituted or unsubstituted C2 to C40 heteroaryl group, or a substituted or unsubstituted C3 to C40 heteroarylalkyl group,

"X is oxygen or sulfur, and

"* indicates a binding position to M of Chemical Formula 1.

"M may be Ir or Pt.

"The organometallic complex represented by the above Chemical Formula 1 may be represented by one of Chemical Formulae A-1 to A-29:

"##STR00015## ##STR00016## ##STR00017## ##STR00018## ##STR00019## ##STR00020## ##STR00021##

"According to another embodiment, an organic electroluminescent device including a first electrode, a second electrode, and an organic layer disposed between the first and second electrodes, wherein the organic layer includes the organometallic complex according to an embodiment, is provided.

"The organic layer may be an emission layer.

"The organometallic complex may be included in an amount of about 1 to about 30 parts by weight based on 100 parts by weight of an emission layer-forming material.

"According to yet another embodiment, a display device including the organic electroluminescent device is provided.

BRIEF DESCRIPTION OF THE DRAWINGS

"These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings in which:

"FIGS. 1A to 1F schematically show the lamination structure of an organic electroluminescent device according to an embodiment;

"FIG. 2 shows an organic electroluminescent device according to an embodiment."

For additional information on this patent application, see: NOH, Chang Ho; KWON, O Hyun; RUPASREE, Ragini Das; KRAVCHUK, Dmitry; CHOI, Hyeon Ho. Organometallic Complexes, and Organic Electroluminescent Device and Display Using the Same. Filed June 19, 2013 and posted June 19, 2014. Patent URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO2&Sect2=HITOFF&u=%2Fnetahtml%2FPTO%2Fsearch-adv.html&r=6252&p=126&f=G&l=50&d=PG01&S1=20140612.PD.&OS=PD/20140612&RS=PD/20140612

Keywords for this news article include: Patents, Isotopes, Nitrogen, Deuterium, Chalcogens, Nanotechnology, Emerging Technologies, Organometallic Organosol.

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