# US 9,437,833 B2 · Organic electroluminescence element > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,437,833 B2 - Document ID: US9437833B2 - Status: Granted - Kind: B2 - Application number: 14/239,723 - Filed: 2012-08-10 - Published: 2014-07-10 - Granted: 2016-09-06 - Earliest claimed: 2011-08-30 - Assignees: Konica Minolta, Inc. - Applicants: Satoru Inoue; Hiroto Ito - Inventors: Satoru Inoue; Hiroto Ito - Web page: https://patentgrep.com/patent/US9437833B2 ## CPC - H10K 50/121: {for assisting energy transfer, e.g. sensitization} - C07F 15/0033: {Iridium compounds} - C09B 57/00: Other synthetic dyes of known constitution - C09B 57/10: Metal complexes of organic compounds not being dyes in uncomplexed form - C09B 69/008: {Dyes containing a substituent, which contains a silicium atom} - C09K 11/06: containing organic luminescent materials - H10K 50/11: characterised by the electroluminescent [EL] layers - C09K 2211/1007: Non-condensed systems - C09K 2211/1029: containing one nitrogen atom as the heteroatom - C09K 2211/1044: containing two nitrogen atoms as heteroatoms - C09K 2211/1074: containing more than three nitrogen atoms as heteroatoms - C09K 2211/1088: containing oxygen as the only heteroatom - C09K 2211/1092: containing sulfur as the only heteroatom - H10K 85/342: {comprising iridium} - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes} - H10K 2101/10: Triplet emission - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract An organic electroluminescent element includes a light-emitting layer between an anode and a cathode. The light-emitting layer contains a phosphorescent light-emitting organic metal complex and at least one host compound. The difference in relative dielectric constant between the host compound and the phosphorescent light-emitting organic metal complex is 0 to −0.5, and the difference in dipole moment between the host compound and the phosphorescent light-emitting organic metal complex is 0 to −5.5 debye. ## Claims ### Claim 1 An organic electroluminescent element comprising a light-emitting layer between an anode and a cathode, wherein the light-emitting layer comprises a phosphorescent light-emitting organic metal complex and at least one host compound; the host compound and the phosphorescent light-emitting organic metal complex have a difference of 0 to −0.5 in relative dielectric constant and have a difference of 0 to −5.5 debye in dipole moment; and the phosphorescent light-emitting organic metal complex is coordinated with a ligand having a partial structure represented by a general formula (1): where R1 represents a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, amino, silyl, arylalkyl, aryl, heteroaryl, alicyclic, or heteroalicyclic group; ring A represents a 5- or 6-membered aromatic hydrocarbon ring or aromatic heterocycle; Ra and Rb each independently represent a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, amino, silyl, arylalkyl, aryl, heteroaryl, alicyclic, or heteroalicyclic group; na represents 1 or 2; and nb represents an integer of 1 to 4. ### Claim 2 (depends on 1) The organic electroluminescent element according to claim 1, wherein the host compound and the phosphorescent light-emitting organic metal complex have a difference of 0 to −4 debye in dipole moment. ### Claim 3 (depends on 1) The organic electroluminescent element according to claim 1, wherein the phosphorescent light-emitting organic metal complex has an emission wavelength of 480 nm or less. ### Claim 4 (depends on 1) The organic electroluminescent element according to claim 1, wherein the phosphorescent light-emitting organic metal complex is coordinated with a ligand having a partial structure represented by a general formula (2): where rings A and B each independently represent a 5- or 6-membered aromatic hydrocarbon ring or aromatic heterocycle; Ar represents a 5- or 6-membered aromatic hydrocarbon ring, aromatic heterocyclic ring, alicyclic ring, or heteroalicyclic ring; R2 and R3 each independently represent a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, amino, silyl, arylalkyl, aryl, heteroaryl, alicyclic, or heteroalicyclic group; Ra, Rb, and Rc each independently represent a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, amino, silyl, arylalkyl, aryl, heteroaryl, alicyclic, or heteroalicyclic group; na and nc each independently represent 1 or 2; and nb represents an integer of 1 to 4. ### Claim 5 (depends on 4) The organic electroluminescent element according to claim 4, wherein R2 and/or R3 represents an alkyl group. ### Claim 6 (depends on 5) The organic electroluminescent element according to claim 5, wherein R2 and/or R3 represents an alkyl group having two or more carbon atoms. ### Claim 7 (depends on 4) The organic electroluminescent element according to claim 4, wherein R2 and R3 represent alkyl groups. ### Claim 8 (depends on 7) The organic electroluminescent element according to claim 7, wherein R2 and R3 represent alkyl groups having two or more carbon atoms. ### Claim 9 (depends on 4) The organic electroluminescent element according to claim 4, wherein ring A is a benzene ring. ### Claim 10 (depends on 4) The organic electroluminescent element according to claim 4, wherein Ar is a benzene ring. ### Claim 11 (depends on 1) The organic electroluminescent element according to claim 1, wherein the phosphorescent light-emitting organic metal complex is an organic metal complex represented by a general formula (3): where rings A and B each independently represent a 5- or 6-membered aromatic hydrocarbon ring or aromatic heterocycle; Ar represents a 5- or 6-membered aromatic hydrocarbon ring, aromatic heterocyclic ring, alicyclic ring, or heteroalicyclic ring; R2 and R3 each independently represent a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, amino, silyl, arylalkyl, aryl, heteroaryl, alicyclic, or heteroalicyclic group; Ra, Rb, and Rc each independently represent a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, amino, silyl, arylalkyl, aryl, heteroaryl, alicyclic, or heteroalicyclic group; na and nc each independently represent 1 or 2; nb represents an integer of 1 to 4; L represents one or more of monoanionic bidentate ligands coordinated to M; M represents a transition metal atom having an atomic number of 40 or more and belonging to any one of Groups 8 to 10 of the periodic table; m represents an integer of 1 to 3; n represents 1 or more; and m+n is 2 or 3. ### Claim 12 (depends on 11) The organic electroluminescent element according to claim 11, wherein the general formula (3) is represented by a general formula (3-1): where Ar, R2, R3, Ra, Rb, Rc, na, nb, nc, M, L, m, and n are synonymous with Ar, R2, R3, Ra, Rb, Rc, na, nb, nc, M, L, m, and n in the general formula (3). ### Claim 13 (depends on 12) The organic electroluminescent element according to claim 12, wherein M is Ir. ### Claim 14 (depends on 1) The organic electroluminescent element according to claim 1, wherein the host compound has a partial structure represented by a general formula (4): where A represents an O or S atom or an NR1 group; A11 to A18 each independently represent a N atom or CR2; and R1 and R2 each independently represent a bonding hand, a hydrogen atom, or a substituent; and if there are a plurality of CR2, they may be the same or different. ### Claim 15 An organic electroluminescent element comprising a light-emitting layer between an anode and a cathode, wherein the light-emitting layer comprises a phosphorescent light-emitting organic metal complex and at least one host compound; the host compound and the phosphorescent light-emitting organic metal complex have a difference of 0 to −0.5 in relative dielectric constant and have a difference of 0 to −5.5 debye in dipole moment; and the host compound has a partial structure represented by a general formula (4): Where A represents an O or S atom or an NR1 group; A11 to A18 each independently represent a N atom or CR2; and R1 and R2 each independently represent a bonding hand, a hydrogen atom, or a substituent; and if there are a plurality of CR2, they may be the same or different. ### Claim 16 (depends on 15) The organic electroluminescent element according to claim 15, wherein the host compound and the phosphorescent light-emitting organic metal complex have a difference of 0 to −4 debye in dipole moment. ### Claim 17 (depends on 15) The organic electroluminescent element according to claim 15, wherein the phosphorescent light-emitting organic metal complex has an emission wavelength of 480 nm or less. ### Claim 18 (depends on 15) The organic electroluminescent element according to claim 15, wherein the phosphorescent light-emitting organic metal complex is coordinated with a ligand having a partial structure represented by a general formula (2): Where rings A and B each independently represent a 5- or 6-membered aromatic hydrocarbon ring or aromatic heterocycle; Ar represents a 5- or 6-membered aromatic hydrocarbon ring, aromatic heterocyclic ring, alicyclic ring, or heteroalicyclic ring; R2 and R3 each independently represent a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, amino, silyl, arylalkyl, aryl, heteroaryl, alicyclic, or heteroalicyclic group; Ra, Rb, and Rc each independently represent a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, amino, silyl, arylalkyl, aryl, heteroaryl, alicyclic, or heteroalicyclic group; na and nc each independently represent 1 or 2; and nb represents an integer of 1 to 4. ### Claim 19 (depends on 15) The organic electroluminescent element according to claim 15, wherein the phosphorescent light-emitting organic metal complex is an organic metal complex represented by a general formula (3): Where rings A and B each independently represent a 5- or 6-membered aromatic hydrocarbon ring or aromatic heterocycle; Ar represents a 5- or 6-membered aromatic hydrocarbon ring, aromatic heterocyclic ring, alicyclic ring, or heteroalicyclic ring; R2 and R3 each independently represent a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, amino, silyl, arylalkyl, aryl, heteroaryl, alicyclic, or heteroalicyclic group; Ra, Rb, and Rc each independently represent a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, amino, silyl, arylalkyl, aryl, heteroaryl, alicyclic, or heteroalicyclic group; na and nc each independently represent 1 or 2; nb represents an integer of 1 to 4; L represents one or more of monoanionic bidentate ligands coordinated to M; M represents a transition metal atom having an atomic number of 40 or more and belonging to any one of Groups 8 to 10 of the periodic table; m represents an integer of 1 to 3; n represents 1 or more; and m+n is 2 or 3.