IP Library › Granted Patent US 12,419,155
Granted Patent B2
US 12,419,155 · App. 17/739,260 · Granted Sep 16, 2025

Hole-transport layer material, electron-blocking layer material, electron-transport layer material, hole-blocking layer material, light-emitting device, light-emitting apparatus, electronic device, and lighting device

Inventors: Takeyoshi Watabe (Kanagawa, JP); Hiromi Seo (Kanagawa, JP); Airi Ueda (Kanagawa, JP); Yuta Kawano (Kanagawa, JP); Tomohiro Kubota (Kanagawa, JP); Yasushi Kitano (Kanagawa, JP); Takao Tosu (Kanagawa, JP); Nobuharu Ohsawa (Kanagawa, JP); Satoshi Seo (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
H10K50/15C07C211/45H10K30/353H10K50/18H10K50/181H10K39/30H10K2101/00
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Quick Facts
Patent No.
US 12,419,155
App. No.
17/739,260
Granted
Sep 16, 2025
Kind
B2
Abstract

An organic semiconductor device with low driving voltage is provided. The light-emitting device includes an anode, a cathode, and an EL layer between the anode and the cathode. The EL layer includes a hole-transport layer and alight-emitting layer. The hole-transport layer is positioned between the anode and the light-emitting layer. The hole-transport layer is not in contact with the anode. The hole-transport layer includes a transport layer material for a light-emitting device and the GSP_slope that is a potential gradient of a surface potential of an evaporated film of the material is higher than or equal to 20 (mV/nm).

Claims (59)

1. A hole transport layer material for a light-emitting device,

wherein a GSP_slope that is a potential gradient of a surface potential of an evaporated film of the hole transport layer material is higher than or equal to 20 mV/nm.

2. The hole transport layer material for a light-emitting device, according to claim 1 ,

wherein the GSP_slope is lower than or equal to 100 mV/nm.

3. The hole transport layer material for a light-emitting device, according to claim 1 ,

wherein an ordinary ray refractive index of the hole transport layer material with respect to light with a wavelength of 450 nm is higher than or equal to 1.50 and lower than or equal to 1.75.

4. The hole transport layer material for a light-emitting device, according to claim 1 ,

wherein an ordinary ray refractive index of the hole transport layer material 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.

5. The hole transport layer material for a light-emitting device, according to claim 1 ,

wherein a glass transition temperature (Tg) of the hole transport layer material is higher than or equal to 100° C.

6. The hole transport layer material for a light-emitting device, according to claim 1 , wherein the hole transport layer material comprises at least three substituents selected from a chain alkyl group having 2 to 5 carbon atoms and a cycloalkyl group having 6 to 12 carbon atoms.

7. The hole transport layer material for a light-emitting device, according to claim 6 ,

wherein the chain alkyl group is a chain alkyl group having a branch formed of 3 to 5 carbon atoms.

8. The hole transport layer material for a light-emitting device, according to claim 6 ,

wherein the chain alkyl group is a t-butyl group.

9. The hole transport layer material for a light-emitting device, according to claim 1 ,

wherein a percentage of carbon atoms forming bonds by sp 3 hybrid orbitals in a total number of carbon atoms in a molecule is higher than or equal to 23% and lower than or equal to 55%.

10. The hole transport layer material for a light-emitting device, according to claim 1 ,

wherein an integral value of signals lower than 4 ppm exceeds an integral value of signals at 4 ppm or higher in a 1H-NMR measurement of the hole transport layer material.

11. The hole transport layer material for a light-emitting device, according to claim 1 ,

wherein the hole transport layer material has a hole-transport property.

12. The hole transport layer material for a light-emitting device, according to claim 11 ,

wherein the hole transport layer material is arylamine.

13. The hole transport layer material for a light-emitting device, according to claim 11 ,

wherein, when the hole transport layer material comprises a condensed aromatic hydrocarbon ring, the condensed aromatic hydrocarbon ring is a bicyclic condensed aromatic ring or a tricyclic condensed aromatic ring and a total number of condensed aromatic hydrocarbon rings in a molecule of the hole transport layer material is one or two.

14. The hole transport layer material for a light-emitting device, according to claim 11 ,

wherein the hole transport layer material comprises two or less fluorene skeletons in a molecule.

15. An electron blocking layer material comprising the hole transport layer material according to claim 11 .

16. A light-emitting device comprising:

an anode;

a cathode; and

an EL layer between the anode and the cathode,

wherein the EL layer comprises a hole-transport layer and a light-emitting layer,

wherein the hole-transport layer is positioned between the anode and the light-emitting layer,

wherein the hole-transport layer is not in contact with the anode,

wherein the hole-transport layer comprises a hole transport layer material, and

wherein a GSP_slope that is a potential gradient of a surface potential of an evaporated film of the hole transport layer material is higher than or equal to 20 mV/nm.

17. The light-emitting device according to claim 16 ,

wherein the hole-transport layer is in contact with the light-emitting layer.

18. An electronic device comprising:

the light-emitting device according to claim 16 ; and

at least one of a sensor, an operation button, a speaker, and a microphone.

19. A light-emitting apparatus comprising:

the light-emitting device according to claim 16 ; and

at least one of a transistor and a substrate.

20. A lighting device comprising:

the light-emitting device according to claim 16 ; and

a housing.

21. A light-emitting device comprising:

an anode;

a cathode; and

an EL layer between the anode and the cathode,

wherein the EL layer comprises a hole-injection layer, a hole-transport layer, an electron-blocking layer, and a light-emitting layer,

wherein the hole-injection layer, the hole-transport layer, and the electron-blocking layer are positioned between the anode and the light-emitting layer,

wherein the electron-blocking layer is in contact with the light-emitting layer,

wherein the hole-injection layer is in contact with the anode,

wherein the hole-transport layer comprises a hole transport layer material,

wherein the electron-blocking layer comprises an electron blocking layer material, and

wherein a GSP_slope of an evaporated film of the hole transport layer material is lower than a GSP slope of an evaporated film of the electron blocking layer material.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 22, 2022
From: WATABE, TAKEYOSHI; SEO, HIROMI; UEDA, AIRI; KAWANO, YUTA; KUBOTA, TOMOHIRO; KITANO, YASUSHI; TOSU, TAKAO; OHSAWA, NOBUHARU; SEO, SATOSHI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 060279/0426 →
Priority Claims (1)
JP 2021-081940 · May 13, 2021 · national
Continuity (1)
Related Publication 20230029353A1 · Jan 26, 2023
References Cited (23)
US 9412962B2 · Hamada. et al. · 2016 [cited by applicant]
US 10950805B2 · Watabe et al. · 2021 [cited by applicant]
US 20070207346A1 · Saitoh et al. · 2007 [cited by applicant]
US 20090066227A1 · Okinaka et al. · 2009 [cited by applicant]
US 20090302758A1 · Saitoh et al. · 2009 [cited by applicant]
US 20100171417A1 · Kitamura. et al. · 2010 [cited by applicant]
US 20130207046A1 · Pflumm et al. · 2013 [cited by applicant]
US 20190016666A1 · Jeong et al. · 2019 [cited by applicant]
US 20200308129A1 · Montenegro et al. · 2020 [cited by applicant]
US 20210005814A1 · Watabe et al. · 2021 [cited by applicant]
US 20210143352A1 · Yamazaki et al. · 2021 [cited by applicant]
US 20210257562A1 · Watabe et al. · 2021 [cited by applicant]
US 20210317069A1 · Seo et al. · 2021 [cited by applicant]
US 20210336151A1 · Tosu et al. · 2021 [cited by applicant]
US 20210336176A1 · Kawano. et al. · 2021 [cited by applicant]
US 20220278292A1 · Watabe et al. · 2022 [cited by applicant]
WO WO2019115577 · 2019 [cited by applicant]
Dalasinski et al.; “Study of optical properties of TRIS (8-hydroxyquinoline) aluminum (III)”; Journal of Applied Physics 111, 114508 (2012) (Year: 2012). [cited by examiner]
Osada et al.; “Observation of spontaneous orientation polarization in evaporated films of organic light-emitting diode materials”; Organic Electronics 58 (2018) 313-317. (Year: 2018). [cited by examiner]
Noguchi.Y et al., “Spontaneous Orientation Polarization of Polar Molecules and Interface Properties of Organic Electronic Devices”, Journal of the Vacuum Society of Japan, Mar. 27, 2015, vol. 58, No. 3, pp. 109-116. [cited by applicant]
Noguch.Y et al., “Spontaneous orientation polarization in organic light-emitting diodes”, Jpn. J. Appl. Phys. (Japanese Journal of Applied Physics) , May 24, 2019, vol. 58, pp. SF0801-1-SF0801-10. [cited by applicant]
Noguchi.Y et al., “Charge accumulation at organic semiconductor interfaces due to a permanent dipole moment and its orientational order in bilayer devices”, J. Appl. Phys. (Journal of Applied Physics) , Jun. 5, 2012, vo… [cited by applicant]
Friederich.P et al., “Built-In Potentials Induced by Molecular Order in Amorphous Organic Thin Films”, ACS Applied Materials & Interfaces, Jan. 5, 2018, vol. 10, No. 2, pp. 1881-1887. [cited by applicant]