# US 10,319,920 B2 · Carbazole derivatives and organic light-emitting diodes by using the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,319,920 B2 - Document ID: US10319920B2 - Status: Granted - Kind: B2 - Application number: 15/413,979 - Filed: 2017-01-24 - Published: 2018-05-31 - Granted: 2019-06-11 - Earliest claimed: 2016-11-30 - Assignees: Yuan Ze University - Applicants: Yuan Ze University - Inventors: Jau-Jiun Huang; Man-Kit Leung; Tien-Lung Chiu; Jiun-Haw Lee; Lik-Ka Yun - Web page: https://patentgrep.com/patent/US10319920B2 ## CPC - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - C07D 209/86: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system - C07D 401/14: containing three or more hetero rings - C07D 413/14: containing three or more hetero rings - C09K 11/025: {non-luminescent particle coatings or suspension media} - C09K 11/06: containing organic luminescent materials - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - H10K 85/6565: {Oxadiazole compounds} - C09K 2211/1007: Non-condensed systems - C09K 2211/1029: containing one nitrogen atom as the heteroatom - C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 85/342: {comprising iridium} - H10K 2101/10: Triplet emission - H10K 2101/30: Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract A carbazole derivative is shown in General Formula (1), wherein R1 is selected from the group consisting of the structures according to the following General Formula (2), General Formula (3) and General Formula (4), wherein R2 to R41 and R80 to R89 are each independently selected from the group consisting of a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkyl group, a thioalkyl group, a silyl group and an alkenyl group. ## Claims ### Claim 1 A carbazole derivative, comprising a structure of the following General Formula (1), wherein R1 is selected from the group consisting of the structures according to the following General Formula (2), General Formula (3) and General Formula (4), wherein R2 to R41 and R80 to R89 are each independently selected from the group consisting of a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkyl group, a thioalkyl group, a silyl group and an alkenyl group. ### Claim 2 (depends on 1) The carbazole derivative of claim 1, wherein the alkyl group is selected from the group consisting of a substituted or unsubstituted straight-chain alkyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain alkyl group with the carbon number of 3 to 6, the cycloalkyl group is a substituted or unsubstituted cycloalkyl group with the carbon number of 3 to 6, the alkoxy group is selected from the group consisting of a substituted or unsubstituted straight-chain alkoxy group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain alkoxy group with the carbon number of 3 to 6, the haloalkyl group is selected from the group consisting of a substituted or unsubstituted straight-chain haloalkyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain haloalkyl group with the carbon number of 3 to 6, the thioalkyl group is selected from the group consisting of a substituted or unsubstituted straight-chain thioalkyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain thioalkyl group with the carbon number of 3 to 6, the silyl group is selected from the group consisting of a substituted or unsubstituted straight-chain silyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain silyl group with the carbon number of 3 to 6, the alkenyl group is selected from the group consisting of a substituted or unsubstituted straight-chain alkenyl group with the carbon number of 2 to 6, and a substituted or unsubstituted branched-chain alkenyl group with the carbon number of 3 to 6. ### Claim 3 A carbazole derivative, comprising a structure of the following General Formula (5), wherein R46 is selected from the group consisting of the structures according to the following General Formula (2), General Formula (3) and General Formula (4), a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkyl group, a thioalkyl group, a silyl group and an alkenyl group, wherein R28 to R41 and R47 to R89 are each independently selected from the group consisting of a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkyl group, a thioalkyl group, a silyl group and an alkenyl group. ### Claim 4 (depends on 3) The carbazole derivative of claim 3, wherein the alkyl group is selected from the group consisting of a substituted or unsubstituted straight-chain alkyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain alkyl group with the carbon number of 3 to 6, the cycloalkyl group is a substituted or unsubstituted cycloalkyl group with the carbon number of 3 to 6, the alkoxy group is selected from the group consisting of a substituted or unsubstituted straight-chain alkoxy group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain alkoxy group with the carbon number of 3 to 6, the haloalkyl group is selected from the group consisting of a substituted or unsubstituted straight-chain haloalkyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain haloalkyl group with the carbon number of 3 to 6, the thioalkyl group is selected from the group consisting of a substituted or unsubstituted straight-chain thioalkyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain thioalkyl group with the carbon number of 3 to 6, the silyl group is selected from the group consisting of a substituted or unsubstituted straight-chain silyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain silyl group with the carbon number of 3 to 6, the alkenyl group is selected from the group consisting of a substituted or unsubstituted straight-chain alkenyl group with the carbon number of 2 to 6, and a substituted or unsubstituted branched-chain alkenyl group with the carbon number of 3 to 6. ### Claim 5 An organic light-emitting diode, comprising; a first electrode layer; a second electrode layer; and an organic luminescent unit, disposed between the first electrode layer and the second electrode layer, wherein the organic luminescent unit has at least a carbazole derivative as shown in General Formula (1), wherein R1 is selected from the group consisting of the structures according to the following General Formula (2), General Formula (3) and General Formula (4), wherein R2 to R41 and R80 to R89 are each independently selected from the group consisting of a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkyl group, a thioalkyl group, a silyl group and an alkenyl group. ### Claim 6 (depends on 5) The organic light-emitting diode of claim 5, wherein the alkyl group is selected from the group consisting of a substituted or unsubstituted straight-chain alkyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain alkyl group with the carbon number of 3 to 6, the cycloalkyl group is a substituted or unsubstituted cycloalkyl group with the carbon number of 3 to 6, the alkoxy group is selected from the group consisting of a substituted or unsubstituted straight-chain alkoxy group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain alkoxy group with the carbon number of 3 to 6, the haloalkyl group is selected from the group consisting of a substituted or unsubstituted straight-chain haloalkyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain haloalkyl group with the carbon number of 3 to 6, the thioalkyl group is selected from the group consisting of a substituted or unsubstituted straight-chain thioalkyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain thioalkyl group with the carbon number of 3 to 6, the silyl group is selected from the group consisting of a substituted or unsubstituted straight-chain silyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain silyl group with the carbon number of 3 to 6, the alkenyl group is selected from the group consisting of a substituted or unsubstituted straight-chain alkenyl group with the carbon number of 2 to 6, and a substituted or unsubstituted branched-chain alkenyl group with the carbon number of 3 to 6. ### Claim 7 (depends on 5) The organic light-emitting diode of claim 5, wherein the organic luminescent unit comprises an organic luminescent layer. ### Claim 8 (depends on 7) The organic light-emitting diode of claim 7, wherein the organic luminescent unit further comprises a hole transport layer and an electron transport layer, and the organic luminescent layer is disposed between the hole transport layer and the electron transport layer. ### Claim 9 (depends on 7) The organic light-emitting diode of claim 7, wherein the organic luminescent unit further comprises a hole transport layer, an electron blocking layer, an electron transport layer and an electron injection layer, and the electron blocking layer, the organic luminescent layer and the electron transport layer are sequentially disposed between the hole transport layer and the electron injection layer. ### Claim 10 (depends on 7) The organic light-emitting diode of claim 7, wherein the organic luminescent layer comprises a host material and a guest material, and the host material is the carbazole derivative and the guest material is a phosphorescent material. ### Claim 11 (depends on 10) The organic light-emitting diode of claim 10, wherein the content of the host material in the organic luminescent layer is between 60 vol % to 95 vol %. ### Claim 12 (depends on 10) The organic light-emitting diode of claim 10, wherein the content of the guest material in the organic luminescent layer is between 5 vol % to 40 vol %. ### Claim 13 An organic light-emitting diode, comprising: a first electrode layer; a second electrode layer; and an organic luminescent unit, disposed between the first electrode layer and the second electrode layer, wherein the organic luminescent unit has at least a carbazole derivative as shown in General Formula (5), wherein R46 is selected from the group consisting of the structures according to the following General Formula (2), General Formula (3) and General Formula (4), a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkyl group, a thioalkyl group, a silyl group and an alkenyl group, whererin R28 to R41 and R47 to R89 are each independently selected from the group consisting of a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkyl group, a thioalkyl group, a silyl group and an alkenyl group. ### Claim 14 (depends on 13) The organic light-emitting diode of claim 13, wherein the alkyl group is selected from the group consisting of a substituted or unsubstituted straight-chain alkyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain alkyl group with the carbon number of 3 to 6, the cycloalkyl group is a substituted or unsubstituted cycloalkyl group with the carbon number of 3 to 6, the alkoxy group is selected from the group consisting of a substituted or unsubstituted straight-chain alkoxy group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain alkoxy group with the carbon number of 3 to 6, the haloalkyl group is selected from the group consisting of a substituted or unsubstituted straight-chain haloalkyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain haloalkyl group with the carbon number of 3 to 6, the thioalkyl group is selected from the group consisting of a substituted or unsubstituted straight-chain thioalkyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain thioalkyl group with the carbon number of 3 to 6, the silyl group is selected from the group consisting of a substituted or unsubstituted straight-chain silyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain silyl group with the carbon number of 3 to 6, the alkenyl group is selected from the group consisting of a substituted or unsubstituted straight-chain alkenyl group with the carbon number of 2 to 6, and a substituted or unsubstituted branched-chain alkenyl group with the carbon number of 3 to 6. ### Claim 15 (depends on 13) The organic light-emitting diode of claim 13, wherein the organic luminescent unit comprises an organic luminescent layer. ### Claim 16 (depends on 15) The organic light-emitting diode of claim 15, wherein the organic luminescent unit further comprises a hole transport layer and an electron transport layer, and the organic luminescent layer is disposed between the hole transport layer and the electron transport layer. ### Claim 17 (depends on 15) The organic light-emitting diode of claim 15, wherein the organic luminescent unit further comprises a hole transport layer, an electron blocking layer, an electron transport layer and an electron injection layer, and the electron blocking layer, the organic luminescent layer and the electron transport layer are sequentially disposed between the hole transport layer and the electron injection layer. ### Claim 18 (depends on 15) The organic light-emitting diode of claim 15, wherein the organic luminescent layer comprises a host material and a guest material, and the host material is the carbazole derivative and the guest material is a phosphorescent material. ### Claim 19 (depends on 18) The organic light-emitting diode of claim 18, wherein the content of the host material in the organic luminescent layer is between 60 vol % to 95 vol %. ### Claim 20 (depends on 18) The organic light-emitting diode of claim 18, wherein the content of the guest material in the organic luminescent layer is between 5 vol % to 40 vol %.