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

Patent metadata

Field	Value
Publication number	US-2025160198-A1
Application number	US-202519019922-A
Country	US
Kind code	A1
Filing date	Jan 14, 2025
Priority date	Mar 31, 2021
Publication date	May 15, 2025
Grant date	—

Abstract

An organic compound having a hole-transport property and a low refractive index is provided. An organic compound represented by General Formula (G1) shown below is provided. In General Formula (G1), Ar 1 represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms in a ring, n represents an integer of 0 or 1, and Ar 2 represents an aryl group having 6 to 10 carbon atoms in a ring and includes at least one branched-chain or cyclic alkyl group having 3 to 12 carbon atoms. The total number of carbon atoms of the branched-chain or cyclic alkyl group in Ar 2 is more than or equal to 6. R 1 to R 4 each independently represent an alkyl group having 1 to 6 carbon atoms. R 11 to R 14 and R 21 to R 24 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Any one of R 15 to R 18 and any one of R 25 to R 28 each represent a bond directly bonded to a nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

First claim

What is claimed is:

1 . A light-emitting device comprising:
an anode; a first layer; a light-emitting layer; and a cathode, wherein the first layer is between the anode and the light-emitting layer, wherein the light-emitting layer is between the first layer and the cathode, wherein the first layer comprises a triarylamine compound, wherein a first fluorenyl group, a second fluorenyl group, and a biphenyl group are directly bonded to a nitrogen atom of amine in the triarylamine compound, wherein the triarylamine compound comprises at least two branched-chain alkyl groups, and wherein an ordinary refractive index of the triarylamine compound with respect to light with a wavelength of 465 nm is higher than or equal to 1.45 and lower than or equal to 1.80.

2 . A light-emitting device comprising:
an anode; a first layer; a light-emitting layer; and a cathode, wherein the first layer is between the anode and the light-emitting layer, wherein the light-emitting layer is between the first layer and the cathode, wherein the first layer comprises a triarylamine compound, wherein a first fluorenyl group, a second fluorenyl group, and a biphenyl group are directly bonded to a nitrogen atom of amine in the triarylamine compound, wherein the triarylamine compound comprises at least two branched-chain alkyl groups, and wherein an ordinary refractive index of the triarylamine compound with respect to light with a wavelength of 520 nm is higher than or equal to 1.45 and lower than or equal to 1.75.

3 . A light-emitting device comprising:
an anode; a first layer; a light-emitting layer; and a cathode, wherein the first layer is between the anode and the light-emitting layer, wherein the light-emitting layer is between the first layer and the cathode, wherein the first layer comprises a triarylamine compound, wherein a first fluorenyl group, a second fluorenyl group, and a biphenyl group are directly bonded to a nitrogen atom of amine in the triarylamine compound, wherein the triarylamine compound comprises at least two branched-chain alkyl groups, and wherein an ordinary refractive index of the triarylamine compound with respect to light with a wavelength of 633 nm is higher than or equal to 1.40 and lower than or equal to 1.75.

4 . The light-emitting device according to claim 1 , wherein the first layer is in contact with the light-emitting layer.

5 . The light-emitting device according to claim 1 , wherein the first layer is a hole-injection layer or a hole-transport layer.

6 . The light-emitting device according to claim 1 ,
wherein the first fluorenyl group comprises a 9,9-dimethyl-9H-fluorenyl group, and wherein the second fluorenyl group comprises a 9,9-dimethyl-9H-fluorenyl group.

7 . The light-emitting device according to claim 1 ,
wherein the ordinary refractive index of the triarylamine compound with respect to light with a wavelength of 465 nm is higher than or equal to 1.50 and lower than or equal to 1.75.

8 . The light-emitting device according to claim 1 , wherein the triarylamine compound is represented by General Formula (G2):

wherein R 1 to R 4 each independently represent an alkyl group having 1 to 6 carbon atoms,
wherein R 11 to R 14 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
wherein any one of R 15 to R 18 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
wherein R 21 to R 24 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
wherein any one of R 25 to R 28 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
wherein R 31 to R 35 each independently represent a hydrogen atom or a branched-chain alkyl group having 3 to 12 carbon atoms, and
wherein n represents an integer of 1.

9 . The light-emitting device according to claim 2 , wherein the first layer is in contact with the light-emitting layer.

10 . The light-emitting device according to claim 2 , wherein the first layer is a hole-injection layer or a hole-transport layer.

11 . The light-emitting device according to claim 2 ,
wherein the first fluorenyl group comprises a 9,9-dimethyl-9H-fluorenyl group, and wherein the second fluorenyl group comprises a 9,9-dimethyl-9H-fluorenyl group.

12 . The light-emitting device according to claim 2 ,
wherein the ordinary refractive index of the triarylamine compound with respect to light with a wavelength of 520 nm is higher than or equal to 1.50 and lower than or equal to 1.70.

13 . The light-emitting device according to claim 2 , wherein the triarylamine compound is represented by General Formula (G2):

wherein R 1 to R 4 each independently represent an alkyl group having 1 to 6 carbon atoms,
wherein R 11 to R 14 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
wherein any one of R 15 to R 18 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
wherein R 21 to R 24 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
wherein any one of R 25 to R 28 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
wherein R 31 to R 35 each independently represent a hydrogen atom or a branched-chain alkyl group having 3 to 12 carbon atoms, and
wherein n represents an integer of 1.

14 . The light-emitting device according to claim 3 , wherein the first layer is in contact with the light-emitting layer.

15 . The light-emitting device according to claim 3 , wherein the first layer is a hole-injection layer or a hole-transport layer.

16 . The light-emitting device according to claim 3 ,
wherein the first fluorenyl group comprises a 9,9-dimethyl-9H-fluorenyl group, and wherein the second fluorenyl group comprises a 9,9-dimethyl-9H-fluorenyl group.

17 . The light-emitting device according to claim 3 ,
wherein the ordinary refractive index of the triarylamine compound with respect to light with a wavelength of 633 nm is higher than or equal to 1.45 and lower than or equal to 1.70.

18 . The light-emitting device according to claim 3 , wherein the triarylamine compound is represented by General Formula (G2):

wherein R 1 to R 4 each independently represent an alkyl group having 1 to 6 carbon atoms,
wherein R 11 to R 14 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
wherein any one of R 15 to R 18 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
wherein R 21 to R 24 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carb

Assignees

• Semiconductor Energy Lab

Inventors

• Kubota Tomohiro
• Tosu Takao
• Watabe Takeyoshi
• Ueda Airi
• Kawano Yuta
• Ohsawa Nobuharu
• Seo Satoshi

Classifications

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title

• H10K85/626

  containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene · CPC title

• H10K59/12

  Active-matrix OLED [AMOLED] displays · CPC title

• H10K50/17

  Carrier injection layers · CPC title

• H10K50/15

  Hole transporting layers · CPC title