# US RE47,654 E1 · Organic electroluminescence device > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US RE47,654 E1 - Document ID: USRE47654E1 - Status: Granted - Kind: E1 - Application number: 14/987,861 - Filed: 2016-01-05 - Granted: 2019-10-22 - Earliest claimed: 2010-01-15 - Assignees: Idemitsu Koasn Co., Ltd. - Applicants: Idemitsu Kosan Co., Ltd. - Inventors: Yuichiro Kawamura; Masahiro Kawamura; Hitoshi Kuma; Hirokatsu Ito - Web page: https://patentgrep.com/patent/USRE47654E1 ## CPC - C09K 11/06: containing organic luminescent materials - H01L 51/0054 - H01L 51/0055 - H01L 51/0067 - H01L 51/0072 - H01L 51/5004 - H01L 51/5012 - H01L 51/5072 - H05B 33/14: 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} - C09K 2211/1007: Non-condensed systems - C09K 2211/1011: Condensed systems - C09K 2211/1029: containing one nitrogen atom as the heteroatom - C09K 2211/1044: containing two nitrogen atoms as heteroatoms - C09K 2211/1088: containing oxygen as the only heteroatom - H01L 51/0059 - H01L 51/0068 - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - H01L - H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL ## Abstract An organic electroluminescence device includes an anode, an emitting layer, an electron-transporting region, and a cathode, the anode, the emitting layer, the electron-transporting region, and the cathode being stacked in this order, the emitting layer including a host material, and a dopant material that emits fluorescence having a main peak wavelength of 550 nm or less, the electron-transporting region including a barrier layer that is adjacent to the emitting layer, and the barrier layer including a barrier material that includes an electron-transporting structural part, and a triplet barrier structural part that includes a fused polycyclic aromatic hydrocarbon compound, and satisfies the relationship “ETb>ETh” (where, ETh is the triplet energy of the host material, and ETb is the triplet energy of the barrier material). ## Claims ### Claim 1 An organic electroluminescence device comprising: an anode, an emitting layer, an electron-transporting region, and a cathode, sequentially; wherein the emitting layer comprises a host material and a dopant material that emits fluorescence having a main peak wavelength of 550 nm or less, the electron-transporting region comprises a barrier layer that is directly adjacent to the emitting layer, the barrier layer comprises a barrier material that comprises an electron-transporting structural portion and a triplet barrier structural portion that comprises a fused polycyclic aromatic hydrocarbon moiety selected from rings shown by the following formulas (6), (7) and (10): wherein Ar2, Ar3, Ar4, Ar8 and Ar9 independently represent a hydrocarbon structure having 4 to 16 ring carbon atoms, which forms a ring fused to the adjacent ring, ETh is the triplet energy level of the host material, ETb is the triplet energy level of the barrier material, and ETb and ETh satisfy the following formula (1), ETb>ETh (1) wherein the electron-transporting structural portion comprises one or more partial structures shown by the following formula, and X1 and X2 independently represent a carbon atom or a nitrogen atom. ### Claim 2 (depends on 1) The organic electroluminescence device of claim 1, wherein ETd is the triplet energy level of the dopant material, and ETd and ETh satisfy the following formula (2), ETd>ETh (2). ### Claim 3 (depends on 1) The organic electroluminescence device of claim 1, wherein an affinity of the host material is Afh, an affinity of the barrier material is Afb, and Afh and Afb satisfy the following formula (3), Afh−Afh>0 eV (3). ### Claim 4 (depends on 1) The organic electroluminescence device of claim 1, wherein an ionization potential of the host material is Iph, an ionization potential of the dopant material is Ipd, and Ipd and Iph satisfy the following formula (4), Ipd−Iph<0.2 eV (4). ### Claim 5 (depends on 1) The organic electroluminescence device of claim 1, wherein the barrier material has an electron mobility of 10−6 cm2/Vs or more. ### Claim 6 (depends on 1) The organic electroluminescence device of claim 1, wherein the barrier layer comprises a donor that reduces the barrier material. ### Claim 7 (depends on 1) The organic electroluminescence device of claim 1, wherein luminous intensity due to singlet excitons that are formed by collision between triplet excitons within the emitting layer accounts for 30% or more of total luminous intensity. ### Claim 8 (depends on 1) The organic electroluminescence device of claim 1, wherein the electron-transporting structural portion comprises one or more rings selected from rings shown by the following formulas, X11 to X15 and X21 to X26 independently represent a carbon atom or a nitrogen atom, at least one of X11 to X15 represent a nitrogen atom, and at least one of X21 to X26 represent a nitrogen atom. ### Claim 9 (depends on 1) The organic electroluminescence device of claim 1, wherein the electron-transporting structural portion comprises one or more rings selected from rings shown by the following formulas, ### Claim 10 (depends on 1) The organic electroluminescence device of claim 1, wherein the electron-transporting structural portion comprises one or more rings selected from rings shown by the following formulas, ### Claim 11 (depends on 1) The organic electroluminescence device of claim 1, wherein the triplet barrier structural portion is selected from rings shown by the following formulas, and Ar1 to Ar9 independently represent a hydrocarbon structure having 4 to 16 ring carbon atoms, which forms a ring fused to the adjacent ring. ### Claim 12 (depends on 1) The organic electroluminescence device of claim 1, comprising at least two emitting layers between the anode and the cathode, and further comprising a carrier-generating layer between the two emitting layers. ### Claim 13 An organic electroluminescence device comprising: an anode, a plurality of emitting layers, an electron-transporting region, and a cathode, sequentially; wherein the organic electroluminescence device further comprises a carrier barrier layer between at least two emitting layers among the plurality of emitting layers, an emitting layer among the plurality of emitting layers that is adjacent to the electron-transporting region comprises a host material and a dopant material that emits fluorescence having a main peak wavelength of 550 nm or less, the electron-transporting region comprises a barrier layer that is adjacent to the emitting layer, the barrier layer comprises a barrier material that comprises an electron-transporting structural portion and a triplet barrier structural portion that comprises a fused polycyclic aromatic hydrocarbon moiety, ETh is the triplet energy level of the host material, ETb is the triplet energy level of the barrier material, and ETb and ETh satisfy the following formula (1), ETb>ETh (1). ### Claim 14 (depends on 13) The organic electroluminescence device of claim 13, wherein ETd is the triplet energy level of the dopant material, and ETd and ETh satisfy the following expression (2), ETd>ETh (2). ### Claim 15 An organic electroluminescence device comprising: an anode, an emitting layer, an electron-transporting region, and a cathode, sequentially; wherein the emitting layer comprises a host material and a dopant material that emits fluorescence having a main peak wavelength of 550 nm or less, the electron-transporting region comprises a barrier layer that is adjacent to the emitting layer, the barrier layer comprises a barrier material that comprises an electron-transporting structural portion and a triplet barrier structural portion that comprises a fused polycyclic aromatic hydrocarbon moiety, ETh is the triplet energy level of the host material, ETb is the triplet energy level of the barrier material, and ETb and ETh satisfy the following formula (1), ETb>ETh (1), wherein an affinity of the host material is Afh, an affinity of the barrier material is Afb, and Afh and Afb satisfy the following formula (3), Afh−Afb>0 eV (3). ### Claim 16 An organic electroluminescence device comprising: an anode, an emitting layer, an electron-transporting region, and a cathode, sequentially; wherein the emitting layer comprises a host material and a dopant material that emits fluorescence having a main peak wavelength of 550 nm or less, the electron-transporting region comprises a barrier layer that is adjacent to the emitting layer, the barrier layer comprises a barrier material that comprises an electron-transporting structural portion and a triplet barrier structural portion that comprises a fused polycyclic aromatic hydrocarbon moiety, ETh is the triplet energy level of the host material, ETb is the triplet energy level of the barrier material, and ETb and ETh satisfy the following formula (1), ETb>ETh (1), wherein an ionization potential of the host material is Iph, an ionization potential of the dopant material is Ipd, and Ipd and Iph satisfy the following formula (4), Ipd−Iph<0.2 eV (4). ### Claim 17 (depends on 1) The organic electroluminescence device of claim 1, wherein the triplet barrier structural portion is selected from rings shown by the following formula (6), wherein Ar2 represents a hydrocarbon structure having 4 to 16 ring carbon atoms, which forms a ring fused to the adjacent ring. ### Claim 18 (depends on 17) The organic electroluminescence device of claim 17, wherein the ring shown by formula (6) has a skeleton selected from the group consisting of the following formulas: ### Claim 19 (depends on 1) The organic electroluminescence device of claim 1, wherein the triplet barrier structural portion is selected from rings shown by the following formula (7), wherein Ar3 and Ar4 independently represent a hydrocarbon structure having 4 to 16 ring carbon atoms, which forms a ring fused to the adjacent ring. ### Claim 20 (depends on 19) The organic electroluminescence device of claim 19, wherein the ring shown by formula (7) has a skeleton selected from the group consisting of the following formulas: ### Claim 21 (depends on 1) The organic electroluminescence device of claim 1, wherein the triplet barrier structural portion is selected from rings shown by the following formula (10), wherein Ar8 and Ar9 independently represent a hydrocarbon structure having 4 to 16 ring carbon atoms, which forms a ring fused to the adjacent ring. ### Claim 22 (depends on 21) The organic electroluminescence device of claim 21, wherein the ring shown by formula (10) has a skeleton selected from the group consisting of the following formulas: ### Claim 23 (depends on 22) The organic electroluminescence device of claim 22, wherein the ring shown by the formula (10) has the skeleton represented by the following formula: ### Claim 24 (depends on 1) The organic electroluminescence device of claim 1, wherein the host material is selected from the group consisting of an anthracene derivative and a pyrene derivative. ### Claim 25 (depends on 24) The organic electroluminescence device of claim 24, wherein the anthracene derivative is represented by the following formula: Ar11 and Ar12 independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atom, or a substituted or unsubstituted heterocyclic group having 5 to 50 atoms that form a ring, and R101 to R108 independently represent a group selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, and a hydroxyl group; and the pyrene derivative is represented by the following formula: Ra represents a hydrogen atom or a substituent, where plural Ras may be the same or different, Ara represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, where plural Aras may be the same or different, L1 represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent aromatic hydrocarbon group having 5 to 30 ring atoms, a is an integer from 1 to 10, p is an integer from 1 to 6, and q is an integer from 0 to 10. ### Claim 26 (depends on 1) The organic electroluminescence device of claim 1, wherein the dopant material is selected from the group consisting of a diaminochrysene derivative, a diaminopyrene derivative, a styrylamine derivative, an amino-substituted fused fluorene derivative, a diaminoanthracene derivative, a boron-containing compound that is substituted with an electron-withdrawing group, a fluorene derivative that does not include an amino group, a fused fluorene derivative that does not include an amino group, a fluoranthene derivative that does not include an amino group, a benzofluoranthene derivative that does not include an amino group, and a pyrene derivative that does not include an amino group. ### Claim 27 (depends on 24) The organic electroluminescence device of claim 24, wherein the host material is the anthracene derivative, and the dopant material is selected from the group consisting of a diaminopyrene derivative, a diaminochrysene derivative, a styrylamine derivative, a boron-containing compound that is substituted with an electron-withdrawing group and a benzofluoranthene derivative that does not include an amino group. ### Claim 28 (depends on 1) The organic electroluminescence device according to claim 1, wherein the electron-transporting structural portion include a monocyclic structure or a fused polycyclic structure that includes one or more rings shown by the following formula: wherein X21 to X26 independently represent a carbon atom or a nitrogen atom, provided that at least one of X21 to X26 represent a nitrogen atom. ### Claim 29 (depends on 1) The organic electroluminescence device according to claim 1, wherein the electron-transporting structural portion includes one or more rings selected from the rings shown by the following formulae: ### Claim 30 (depends on 1) The organic electroluminescence device according to claim 1, wherein the electron-transporting structural portion includes one or more rings shown by the following formula: ### Claim 31 (depends on 1) The organic electroluminescence device according to claim 1, wherein the electron-transporting structural portion includes a ring shown by the following formula: ### Claim 32 (depends on 1) The organic electroluminescence device according to claim 1, wherein the triplet barrier structural portion is a ring shown by the following formula: the electron-transporting structural portion includes one or more rings shown by the following formula: ### Claim 33 An organic electroluminescence device comprising: an anode, an emitting layer, an electron-transporting region, and a cathode, sequentially; wherein the emitting layer comprises a host material and a dopant material that emits fluorescence having a main peak wavelength of 550 nm or less, the electron-transporting region comprises a barrier layer that is adjacent to the emitting layer, the barrier layer comprises a barrier material that comprises an electron-transporting structural portion and a triplet barrier structural portion that comprises a fused polycyclic aromatic hydrocarbon moiety selected from rings shown by the following formula (10), wherein Ar8 and Ar9 independently represent a hydrocarbon structure having 4 to 16 ring carbon atoms, which forms a ring fused to the adjacent ring, ETh is the triplet energy level of the host material, ETb is the triplet energy level of the barrier material, and ETb and ETh satisfy the following formula (1), ETb>ETh (1) wherein the electron-transporting structural portion comprises one or more partial structures shown by the following formula, and X1 and X2 independently represent a carbon atom or a nitrogen atom, provided that layers between the emitting layer and the cathode do not comprise a compound having a ring which has partial structures shown by the following formulae (6) and (7) wherein Ar2, Ar3, and Ar4 independently represent a hydrocarbon structure having 4 to 16 ring carbon atoms, which forms a ring fused to the adjacent ring. ### Claim 34 (depends on 33) The organic electroluminescence device of claim 33, wherein ETd is the triplet energy level of the dopant material, and ETd and ETh satisfy the following formula (2), ETd>ETh (2). ### Claim 35 (depends on 33) The organic electroluminescence device of claim 33, wherein an affinity of the host material is Afh, an affinity of the barrier material is Afb, and Afh and Afb satisfy the following formula (3), Afh−Afb>0 eV (3). ### Claim 36 (depends on 33) The organic electroluminescence device of claim 33, wherein an ionization potential of the host material is Iph, an ionization potential of the dopant material is Ipd, and Ipd and Iph satisfy the following formula (4), Ipd−Iph<0.2 eV (4). ### Claim 37 (depends on 33) The organic electroluminescence device of claim 33, wherein the barrier material has an electron mobility of 10−6 cm2/Vs or more. ### Claim 38 (depends on 33) The organic electroluminescence device of claim 33, wherein the barrier layer comprises a donor that reduces the barrier material. ### Claim 39 (depends on 33) The organic electroluminescence device of claim 33, wherein luminous intensity due to singlet excitons that are formed by collision between triplet excitons within the emitting layer accounts for 30% or more of total luminous intensity. ### Claim 40 (depends on 33) The organic electroluminescence device of claim 33, wherein the electron-transporting structural portion comprises one or more rings selected from rings shown by the following formulas, X11 to X15 and X21 to X26 independently represent a carbon atom or a nitrogen atom, at least one of X11 to X15 represent a nitrogen atom, and at least one of X21 to X26 represent a nitrogen atom. ### Claim 41 (depends on 33) The organic electroluminescence device of claim 33, comprising at least two emitting layers between the anode and the cathode, and further comprising a carrier-generating layer between the two emitting layers. ### Claim 42 (depends on 33) The organic electroluminescence device of claim 33, wherein the dopant material is selected from the group consisting of a diaminochrysene derivative, a diaminopyrene derivative, a styrylamine derivative, an amino-substituted fused fluorene derivative, a diaminoanthracene derivative, a boron-containing compound that is substituted with an electron-withdrawing group, a fluorene derivative that does not include an amino group, a fused fluorene derivative that does not include an amino group, a fluoranthene derivative that does not include an amino group, a benzofluoranthene derivative that does not include an amino group, and a pyrene derivative that does not include an amino group. ### Claim 43 (depends on 33) The organic electroluminescence device of claim 33, wherein the host material is the anthracene derivative, and the dopant material is selected from the group consisting of a diaminopyrene derivative, a diaminochrysene derivative, a styrylamine derivative, a boron-containing compound that is substituted with an electron-withdrawing group and a benzofluoranthene derivative that does not include an amino group. ### Claim 44 (depends on 33) The organic electroluminescence device according to claim 33, wherein the electron-transporting structural portion include a monocyclic structure or a fused polycyclic structure that includes one or more rings shown by the following formula: wherein X21 to X26 independently represent a carbon atom or a nitrogen atom, provided that at least one of X21 to X26 represent a nitrogen atom. ### Claim 45 (depends on 33) The organic electroluminescence device according to claim 33, wherein the electron-transporting structural portion includes one or more rings selected from the rings shown by the following formulae: ### Claim 46 (depends on 33) The organic electroluminescence device according to claim 33, wherein the electron-transporting structural portion includes one or more rings shown by the following formula: ### Claim 47 (depends on 33) The organic electroluminescence device according to claim 33, wherein the electron-transporting structural portion includes a ring shown by the following formula: ### Claim 48 (depends on 33) The organic electroluminescence device according to claim 33, wherein the triplet barrier structural portion is a ring shown by the following formula: the electron-transporting structural portion includes one or more rings shown by the following formula: