Organic light-emitting composite and method for patterning organic light-emitting thin film comprising same, organic light-emitting composition comprising same, and organic light-emitting device comprising same

Patent metadata

Field	Value
Publication number	US-2025204141-A1
Application number	US-202318843922-A
Country	US
Kind code	A1
Filing date	Mar 3, 2023
Priority date	Mar 4, 2022
Publication date	Jun 19, 2025
Grant date	—

Abstract

Disclosed are an organic light-emitting composite, a high-resolution patterning method for an organic light-emitting thin film including the same, an organic light emitting composition including the organic light-emitting composite, and an organic light-emitting device including the organic light emitting composition. More particularly, the organic light-emitting composite includes a curable phosphorescent host; a curable phosphorescent dopant; and an organic silica precursor forming a silicone (—Si—O—Si—) network together with the curable phosphorescent host and the curable phosphorescent dopant, wherein the curable phosphorescent host and the curable phosphorescent dopant include a cross-linking functional group.

First claim

1 . An organic light-emitting composite, comprising:
a curable phosphorescent host; a curable phosphorescent dopant; and an organic silica precursor forming a silicone (—Si—O—Si—) network together with the curable phosphorescent host and the curable phosphorescent dopant, wherein the curable phosphorescent host and the curable phosphorescent dopant comprise a cross-linking functional group.

2 . The organic light-emitting composite according to claim 1 , wherein the silicone (—Si—O—Si—) network is a silicone (—Si—O—Si—)-integrated Single Phase Network (SPN), and
the silicone (—Si—O—Si—)-integrated SPN is formed by a simultaneous crosslinking reaction among the curable phosphorescent host, the curable phosphorescent dopant and the organic silica precursor.

3 . The organic light-emitting composite according to claim 1 , wherein the silicone (—Si—O—Si—) network is a silicone (—Si—O—Si—)-integrated Interpenetrating Polymer Network (IPN), and
the silicone (—Si—O—Si—)-integrated IPN is formed by a simultaneous crosslinking reaction between the curable phosphorescent host and the curable phosphorescent dopant and a selective crosslinking reaction between the organic silica precursor.

4 . The organic light-emitting composite according to claim 1 , wherein the cross-linking functional group comprises at least one of a vinyl group, a vinyl group derivative, an oxetane group, a boronic acid group, trifluoro vinyl ether, benzocyclobutene and epoxide.

5 . The organic light-emitting composite according to claim 4 , wherein the cross-linking functional group comprises a functional group represented by one of Formulas 4 to 9 below:

wherein, in Formulas 4 to 9, R 1 each independently comprises one of a hydrogen, a heavy hydrogen, a cyano group, a halogen group, an amino group, a thiol group, a hydroxy group, a nitro group, a carbonyl group, an ether group, a silane group, a siloxane group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkenyloxyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms alkenylaryl group, a substituted or unsubstituted arylalkoxy group having 7 to 30 carbon atoms, a substituted or unsubstituted arylalkenyl group having 8 to 30 carbon atoms and a substituted or unsubstituted alkoxycarbonyl group having 2 to 20 carbon atoms.

6 . The organic light-emitting composite according to claim 1 , wherein the curable phosphorescent dopant is a metal complex compound to which the cross-linking functional group has been bonded, and
the metal complex compound comprises at least one metal of iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), euroform (Eu), terbium (Tb), palladium (Pd) and thallium (Tm).

7 . The organic light-emitting composite according to claim 6 , wherein the curable phosphorescent dopant comprises a compound represented by one of Formulas 10 and 11 below:

wherein, in Formulas 10 and 11, n is 2 or 3, Ar 1 and Ar 2 are each at least one of a negatively charged and neutrally independently substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted fluorenyl group and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, L-X is a negatively charged di-coordinate ligand, R is a cross-linking functional group, and A each independently comprises at least one of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted fluorenyl group and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

8 . The organic light-emitting composite according to claim 7 , wherein luminescence intensity and charge lifespan of the organic light-emitting composite are controlled depending upon a content of the curable phosphorescent dopant.

9 . The organic light-emitting composite according to claim 8 , wherein a content of the curable phosphorescent dopant is 0.5% by weight to 20% by weight based on the organic light-emitting composite.

10 . The organic light-emitting composite according to claim 1 , wherein the curable phosphorescent host is a host compound to which the cross-linking functional group has been bonded, and
the host compound comprises at least one of a carbazole-based compound, an anthracene-based compound, a fluorene-based compound, a triarylamine-based compound, a dibenzofuran-based compound, a dibenzothiophene-based compound, a dibenzosilole-based compound, a triazine-based compound, a triazole-based compound, an imidazole-based compound, an oxazine-based compound, an arylamine-based compound, a hydrazone-based compound, a stilbene-based compound, a starburst-based compound, an oxadiazole-based compound, a phosphine oxide-based compound, a bipyrimidine-based compound, a silane-based compound and a carboline-based compound.

11 . The organic light-emitting composite according to claim 10 , wherein the curable phosphorescent host comprises a compound represented by one of Formulas 1 to 3 below:

wherein, in Formulas 1 to 3, R is a cross-linking functional group.

12 . The organic light-emitting composite according to claim 1 , wherein the organic silica precursor comprises a compound represented by one of Formulas 12 to 22 below:

wherein, in Formula 12, R′ comprises one to three halogen elements or one to three alkoxy (—O—(CH 2 ) x —CH 3 , where X is an integer of 0 to 8.), and m is an integer of 0 to 20

wherein, in Formula 16, R′ comprises one to three halogen elements or one to three alkoxy (—O—(CH 2 ) x —CH 3 , where X is an integer of 0 to 8

13 . A patterning method for an organic light-emitting thin film, the patterning method comprising:
forming an organic light-emitting thin film comprising an organic light-emitting composite on a substrate; forming a photoresist on the organic light-emitting thin film; patterning the photoresist to form a photoresist pattern; dry-etching the organic light-emitting thin film using the photoresist pattern as an etching mask to form an organic light-emitting pattern; and removing the photoresist pattern.

14

Assignees

• Iucf Hyu

Inventors

• Kim Do Hwan
• You Youngmin
• Kim Bong Soo
• Kweon Hyuk Min
• Park Sang Jun
• Jeong Uk Jin
• Choi Seok Ran
• Ha Bo Ri Na
• Chun Yu Sung
• Song Da Yoon
• Shahid Ameen
• Heo Yu Chan

Classifications

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K85/658

  Organoboranes · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K71/233

  by photolithographic etching · CPC title