# US 11,114,620 B2 · Organic light-emitting diode device and compound for charge generation layer included therein > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,114,620 B2 - Document ID: US11114620B2 - Status: Granted - Kind: B2 - Application number: 16/206,969 - Filed: 2018-11-30 - Published: 2019-09-19 - Granted: 2021-09-07 - Earliest claimed: 2018-03-13 - Assignees: Samsung Display Co., Ltd. - Applicants: Samsung Display Co., Ltd. - Inventors: Yoonhyeung Cho; Hyungseok Jang; Dongchan Kim; Wonjong Kim; Jiyoung Moon; Yeongrong Park; Dongkyu Seo; Myungchul Yeo; Jihye Lee - Web page: https://patentgrep.com/patent/US11114620B2 ## CPC - C07F 5/025: {Boronic and borinic acid compounds} - H10K 85/611: {Charge transfer complexes} - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - H10K 85/658: {Organoboranes} - H10K 50/131: {with spacer layers between the electroluminescent layers} - H10K 50/19: Tandem OLEDs - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract Disclosed is an organic light-emitting diode device including: a first electrode; a second electrode disposed opposite to the first electrode; m light-emitting units (where m is an integer of 2 or more) disposed between the first electrode and the second electrode, and including at least one light-emitting layer; and m-1 charge generation layers each interposed between two adjacent light-emitting units of the m light-emitting units; wherein at least one of the m-1 charge generation layers includes a compound for a charge generation layer, which includes a boron-containing compound bonded to a metal halide by a one-electron sigma bond. ## Claims ### Claim 1 An organic light-emitting diode device comprising: a first electrode; a second electrode disposed opposite to the first electrode; m light-emitting units (where m is an integer of 2 or more) disposed between the first electrode and the second electrode, and comprising at least one light-emitting layer; and m-1 charge generation layers each interposed between two adjacent light-emitting units of the m light-emitting units; wherein at least one of the m-1 charge generation layers comprises a compound represented by Formula 1 below: Y2Y1B-M(X)a Formula 1 wherein: M is a metal selected from the group consisting of Group 1 metals, Group 2 metals, transition metals, post-transition metals, lanthanides, and actinides, which have a work function of 4.0 eV or less; X is a halogen element selected from the group consisting of F, Cl, Br, and I; a is a natural number ranging from 1 to 4; and Y1 and Y2 are the same or different, and are each independently one or more selected from the group consisting of a halogen, a hydroxyl group, a nitro group, a cyano group, an amine group, a C1-C40 alkyl group, a C6-C40 aryl group, and a 5- to 40-membered heteroaryl group, or they may be bonded to an adjacent group to form a condensed ring, provided that at least one of Y1 and Y2 is a C6-C40 aryl group or a 5- to 40-membered heteroaryl group; and wherein the alkyl group, the aryl group, and the heteroaryl group are each unsubstituted or substituted with one or more substituents selected from the group consisting of a halogen, a cyano group, a nitro group, a C1-C40 alkyl group, a C6-C40 aryl group, a 5- to 40-membered heteroaryl group, a C6-C40 aryloxy group, a C6-C40 arylphosphine oxide group, and a C6-C40 arylamine group, and the substituents may be the same or different if they are plural in number. ### Claim 2 (depends on 1) The organic light-emitting diode device of claim 1, wherein the compound represented by formula 1 is a charge-transfer (CT) complex comprising a boron-containing compound and a metal halide. ### Claim 3 (depends on 2) The organic light-emitting diode device of claim 2, wherein a content ratio between the boron-containing compound and the metal halide is 0.5-50:50-95.5 by weight. ### Claim 4 (depends on 1) The organic light-emitting diode device of claim 1, wherein the compound represented by formula 1 is bonded to adjacent compounds of formula 1 to form a cluster, and the cluster comprises at least one heterocyclic ring containing the boron and the metal (M). ### Claim 5 (depends on 1) The organic light-emitting diode device of claim 1, wherein each of the m-1 charge generation layers comprises at least one host and at least one dopant, and one of the at least one host and at least one dopant is the compound represented by formula 1. ### Claim 6 (depends on 1) The organic light-emitting diode device of claim 1, wherein the m light-emitting units are disposed alternately with the m-1 charge generation layers, and two light-emitting units of the m light-emitting units are disposed adjacent to the first electrode and the second electrode, respectively. ### Claim 7 (depends on 1) The organic light-emitting diode device of claim 1, wherein: each of the m light-emitting units comprises a hole transport region, a light-emitting layer, and an electron transport region; the hole transport region comprises at least one of a hole injection layer and a hole transport layer; and the electron transport region comprises at least one of an electron transport layer and an electron transport layer. ### Claim 8 (depends on 1) The organic light-emitting diode device of claim 1, wherein: each of the m-1 charge generation layers comprises an n-type charge generation layer and a p-type charge generation layer; the n-type charge generation layer is disposed adjacent to the electron transport region of each of the m light-emitting units; and the p-type charge generation layer is disposed adjacent to the hole transport region of each of the m light-emitting units. ### Claim 9 (depends on 8) The organic light-emitting diode device of claim 8, wherein the n-type charge generation layer comprises a metal selected from the group consisting of Group 1 metals, Group 2 metals, lanthanides, and actinides, which have a work function of 4.0 eV or less. ### Claim 10 (depends on 8) The organic light-emitting diode device of claim 8, wherein the p-type charge generation layer comprises a metal selected from the group consisting of transition metals and post-transition metals, which have a work function of 4.0 eV or less. ### Claim 11 A compound for a charge generation layer, comprising: at least one boron-containing compound; and at least one metal halide containing a metal having a work function of 4.0 eV or less; wherein the boron (B) of the boron-containing compound and the metal (M) of the metal halide are bonded to each other by a one-electron sigma bond. ### Claim 12 (depends on 11) The compound of claim 11, wherein a bonding value between the metal (M) and the boron (B), which is measured by X-ray photoelectron spectrometry (XPS), ranges from 180 to 290 eV. ### Claim 13 (depends on 11) The compound of claim 11, wherein the compound is represented by Formula 1 below: Y2Y1B-M(X)a Formula 1 wherein: M is a metal selected from the group consisting of Group 1 metals, Group 2 metals, transition metals, post-transition metals, lanthanides, and actinides, which have a work function of 4.0 eV or less; X is a halogen element selected from the group consisting of F, Cl, Br, and I; a is a natural number ranging from 1 to 4; and Y1 and Y2 are the same or different, and are each independently one or more selected from the group consisting of a halogen, a hydroxyl group, a nitro group, a cyano group, an amine group, a C1-C40 alkyl group, a C6-C40 aryl group, and a 5- to 40-membered heteroaryl group, or they may be bonded to an adjacent group to form a condensed ring, provided that at least one of Y1 and Y2 is a C6-C40 aryl group or a 5- to 40-membered heteroaryl group; and wherein the alkyl group, the aryl group, and the heteroaryl group are each unsubstituted or substituted with one or more substituents selected from the group consisting of a halogen, a cyano group, a nitro group, a C1-C40 alkyl group, a C6-C40 aryl group, a 5- to 40-membered heteroaryl group, a C6-C40 aryloxy group, a C6-C40 arylphosphine oxide group, and a C6-C40 arylamine group, and the substituents may be the same or different if they are plural in number. ### Claim 14 (depends on 11) The compound of claim 11, wherein the metal halide is a metal iodide. ### Claim 15 (depends on 11) The compound of claim 11, wherein the compound is used for an n-type charge generation layer, a p-type charge generation layer, or both. ### Claim 16 (depends on 15) The compound of claim 15, wherein the n-type charge generation layer comprises a metal selected from the group consisting of Group 1 metals, Group 2 metals, lanthanides, and actinides, which have a work function of 4.0 eV or less. ### Claim 17 (depends on 15) The compound of claim 15, wherein the p-type charge generation layer comprises a metal selected from the group consisting of transition metals and post-transition metals, which have a work function of 4.0 eV or less. ### Claim 18 (depends on 11) The compound of claim 11, wherein the compound is a charge-transfer (CT) complex comprising a boron-containing compound and a metal halide. ### Claim 19 (depends on 18) The compound of claim 18, wherein a content ratio between the boron-containing compound and the metal halide is 0.5-50:50-95.5 by weight. ### Claim 20 (depends on 13) The compound of claim 13, wherein the compound represented by formula 1 is bonded to adjacent compounds of formula 1 to form a cluster, and the cluster comprises at least one heterocyclic ring containing the boron and the metal (M).