Organic compound, EL device, light-emitting apparatus, electronic appliance, lighting device, and electronic device

Patent metadata

Field	Value
Publication number	US-12344602-B2
Application number	US-201917292742-A
Country	US
Kind code	B2
Filing date	Nov 12, 2019
Priority date	Nov 16, 2018
Publication date	Jul 1, 2025
Grant date	Jul 1, 2025

Abstract

An object is to provide an organic compound with a low refractive index. Alternatively, a novel organic compound with a low refractive index and an electron-donating property is provided. Alternatively, an EL device with high emission efficiency is provided. An organic compound having an arylamine skeleton including a fluorine atom or an acridine skeleton including a fluorine atom and an EL device using the organic compound are provided. The EL device preferably includes a hole-injection layer containing the organic compound having an arylamine skeleton including a fluorine atom or an acridine skeleton including a fluorine atom and a substance showing an electron-accepting property with respect to the organic compound.

First claim

The invention claimed is:

1. A compound represented by Formula (G1),

wherein each of R 1 to R 4 and R 7 to R 10 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and an alkyl fluoride group having 1 to 6 carbon atoms,
wherein each of R 5 and R 6 represents an unsubstituted phenyl group,
wherein R 13 represents a group represented by Formula (g1),

wherein each of R 21 to R 24 and R 27 to R 30 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and an alkyl fluoride group having 1 to 6 carbon atoms, and
wherein each of R 25 and R 26 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkyl fluoride group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group, and
wherein a proportion of fluorine included in the compound is higher than or equal to 7 atomic % and lower than or equal to 40 atomic %.

2. A compound represented by Formula (G2),

wherein each of R 1 to R 4 and R 7 to R 10 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and an alkyl fluoride group having 1 to 6 carbon atoms,
wherein each of R 5 and R 6 represents an unsubstituted phenyl group,
wherein R 33 represents a group represented by Formula (g1),

wherein each of R 21 to R 24 and R 27 to R 30 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and an alkyl fluoride group having 1 to 6 carbon atoms, and
wherein each of R 25 and R 26 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkyl fluoride group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group, and
wherein a proportion of fluorine included in the compound is higher than or equal to 7 atomic % and lower than or equal to 40 atomic %.

3. The compound according to claim 2 , wherein the compound is represented by Formula (200):

4. A light-emitting device comprising the compound according to claim 1 .

5. A light-emitting device comprising:
a first electrode;
a first hole-injection layer over the first electrode, the first hole-injection layer comprising a compound; and
a second electrode over the first hole-injection layer,
wherein the compound comprises:
an acridine skeleton;
a first phenyl group bonded to a nitrogen atom in the acridine skeleton;
a first substituent bonded to the acridine skeleton; and
a second substituent bonded to the acridine skeleton,

wherein the first phenyl group is substituted by a fluorine atom,
wherein each of the first substituent and the second substituent independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cyclohexyl group, an alkyl fluoride group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group, and
wherein a proportion of fluorine included in the compound is higher than or equal to 7 atomic % and lower than or equal to 40 atomic %.

6. The light-emitting device according to claim 5 , wherein the first hole-injection layer further comprises a substance exhibiting an electron-accepting property with respect to the compound.

7. The light-emitting device according to claim 6 ,
wherein the substance exhibiting an electron-accepting property is an organic compound or any one of molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide and manganese oxide,
wherein the organic compound comprises a fused aromatic ring having a plurality of heteroatoms, and
wherein the fused aromatic ring is substituted with at least one of a cyano group and a halogen group.

8. The light-emitting device according to claim 5 , wherein the first hole-injection layer is in contact with the first electrode.

9. The light-emitting device according to claim 6 , further comprising a second hole-injection layer over the first hole-injection layer,
wherein the second hole-injection layer comprises the substance exhibiting an electron-accepting property.

10. The light-emitting device according to claim 5 , wherein the first hole-injection layer has a refractive index less than or equal to 1.8.

11. A light-emitting device comprising the compound according to claim 2 .

Assignees

• Semiconductor Energy Lab

Inventors

• Watabe Takeyoshi
• Kubota Tomohiro
• Seo Satoshi

Classifications

• H10K59/875

  Arrangements for extracting light from the devices · CPC title

• H10K50/17

  Carrier injection layers · CPC title

• H10K85/6572 Primary

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

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K50/16

  Electron transporting layers · CPC title