# US 2019/0378997 A1 · Compound, light emitting material and organic light emitting element > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2019/0378997 A1 - Document ID: US20190378997A1 - Status: Published application - Kind: A1 - Application number: 16/489,385 - Filed: 2018-02-28 - Published: 2019-12-12 - Earliest claimed: 2017-02-28 - Applicants: Kyushu University, National University Corporation; King Abdullah University of Science and Technology - Inventors: Yuma ISHIKAWA; Youichi TSUCHIYA; Chihaya ADACHI; Jean-Luc BREDAS; Xiankai CHEN - Web page: https://patentgrep.com/patent/US20190378997A1 ## CPC - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - C07D 455/03: containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine - C07D 471/16: Peri-condensed systems - C09K 11/06: containing organic luminescent materials - H10K 85/621: {Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide} - H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom} - C09K 2211/1018: Heterocyclic compounds - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - H10K 2101/10: Triplet emission - H10K 2101/20: Delayed fluorescence emission - H10K 2101/30: Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values - H10K 2101/40: Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract A compound having a structure, represented by the following general formula is useful as a light emitting material. At least one of R1 to R9 is a substituent; Y1 to Y3 each are a methylene group, a carbonyl group, a thiocarbonyl group, an imino group, an oxygen atom, a sulfur atom or a sulfonyl group; Z is a nitrogen atom, a boron atom or a phosphine oxide group. ## Claims ### Claim at position 1 1-40. (canceled) ### Claim 41 A compound having a structure represented by the following general formula (1): wherein R1 to R9 each independently represent a hydrogen atom or a substituent, and at least one of R1 to R9 is a substituent; Y1 to Y3 each independently represent a substituted or unsubstituted methylene group (C(R10)(R11) where R10 and R11 each independently represent a hydrogen atom or a substituent), a carbonyl group (C═O), a thiocarbonyl group (C═S), a substituted or unsubstituted imino group (N(R12) where R12 represents a hydrogen atom or a substituent), an oxygen atom, a sulfur atom, or a sulfonyl group (SO2); Z represents a nitrogen atom, a boron atom, or a phosphine oxide group (P═O). ### Claim 42 (depends on 41) The compound according to claim 41, wherein in the general formula (1), one or two of R2, R5 and R8 each are a substituted or unsubstituted diarylamino group having 12 to 40 carbon atoms, or a substituted or unsubstituted carbazolyl group having 12 to 40 carbon atoms, and at least one of Y1 to Y3 is a carbonyl group (C═O). ### Claim 43 (depends on 41) The compound according to claim 41, wherein in the general formula (1), at least one of R1 to R9 is a substituted or unsubstituted diarylamino group having 12 to 40 carbon atoms, and at least one of Y1 to Y3 is a carbonyl group (C═O). ### Claim 44 (depends on 41) The compound according to claim 41, wherein in the general formula (1), at least one of R1 to R9 is an aryl group having 6 to 40 carbon atoms and substituted with a substituted or unsubstituted diphenylamino group, and at least one of Y1 to Y3 is a carbonyl group (C═O). ### Claim 45 (depends on 44) The compound according to claim 44, wherein the aryl group is a phenyl group. ### Claim 46 (depends on 41) The compound according to claim 41, represented by the following general formula (2): wherein R1 to R9 each independently represent a hydrogen atom or a substituent, and at least one of R1 to R9 is a substituted or unsubstituted heteroaryl group, provided that at least one ring skeleton-constituting atom adjacent to the atom that participates in bonding of the heteroaryl group is a nitrogen atom; R11 to R16 each independently represent a substituent; Z represents a nitrogen atom, a boron atom, or a phosphine oxide group (P═O). ### Claim 47 (depends on 46) The compound according to claim 46, wherein the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted diaryltriazinyl group, and R11 to R16 in the general formula (2) each are independently a substituted or unsubstituted alkyl group. ### Claim 48 (depends on 46) The compound according to claim 46, wherein in the general formula (2), R2 is a substituted or unsubstituted heteroaryl group, and at least one ring skeleton-constituting atom adjacent to the atom that participates in bonding of the group is a nitrogen atom; and at least one of R4 to R6, and R7 to R9 is a group containing a diarylamino structure, or a group containing a carbazole ring. ### Claim 49 (depends on 48) The compound according to claim 48, wherein the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted triazinyl group. ### Claim 50 (depends on 48) The compound according to claim 48, wherein the group containing a diarylamino structure is a diarylamino group substituted with a substituent. ### Claim 51 (depends on 41) The compound according to claim 41, represented by the following general formula (3): wherein R1 to R9 each independently represent a hydrogen atom or a substituent, and at least one of R1 to R9 is a substituent; Z represents a nitrogen atom, a boron atom or a phosphine oxide group (P═O). ### Claim 52 (depends on 51) The compound according to claim 51, wherein in the general formula (3), one or two of R2, R5, and R8 each are a group containing a diarylamino structure or a group containing a carbazole ring. ### Claim 53 (depends on 51) The compound according to claim 51, wherein in the general formula (3), at least one of R1 to R9 is a group containing a substituted or unsubstituted diarylamino group. ### Claim 54 (depends on 51) The compound according to claim 51, wherein in the general formula (3), at least one of R1 to R9 is a group having a structure represented by the following general formula (4): wherein R21 to R30 each independently represent a hydrogen atom or a substituent; R25 and R26 may bond to each other to form a single bond or a linking group; L represents a single bond or a substituted or unsubstituted arylene group; * represents a bonding position. ### Claim 55 (depends on 54) The compound according to claim 54, wherein R25 and R26 in the general formula (4) do not bond to each other. ### Claim 56 (depends on 54) The compound according to claim 54, wherein L in the general formula (4) is a substituted or unsubstituted arylene group. ### Claim 57 (depends on 54) The compound according to claim 54, wherein L in the general formula (4) is a substituted or unsubstituted phenylene group. ### Claim 58 (depends on 54) The compound according to claim 54, wherein at least one of R23 and R24 in the general formula (4) is a hydrogen atom. ### Claim 59 An organic light-emitting device containing a compound having a structure represented by the following general formula (1): wherein R1 to R9 each independently represent a hydrogen atom or a substituent, and at least one of R1 to R9 is a substituent; Y1 to Y3 each independently represent a substituted or unsubstituted methylene group (C(R10)(R11) where R10 and R11 each independently represent a hydrogen atom or a substituent), a carbonyl group (C═O), a thiocarbonyl group (C═S), a substituted or unsubstituted imino group (N(R12) where R12 represents a hydrogen atom or a substituent), an oxygen atom, a sulfur atom, or a sulfonyl group (SO2); Z represents a nitrogen atom, a boron atom, or a phosphine oxide group (P═O). ### Claim 60 (depends on 59) The organic light-emitting device according to claim 59, which emits delayed fluorescence.