IP Library Granted Patent US 12,652,952
Granted Patent B2
US 12,652,952 · App. 17/412,450 · Granted Jun 9, 2026

Light-emitting device, light-emitting apparatus, electronic apparatus, and lighting device

Inventors: Nobuharu Ohsawa (Zama, JP); Satoshi Seo (Sagamihara, JP); Takeyoshi Watabe (Atsugi, JP); Airi Ueda (Sagamihara, JP); Tomohiro Kubota (Atsugi, JP); Takashi Hirahara (Atsugi, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
H10K85/633C07C211/61C07C2601/14C07C2603/18H10K50/15H10K50/17H10K59/12H10K59/874H10K59/876H10K85/615
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,652,952
App. No.
17/412,450
Granted
Jun 9, 2026
Kind
B2
Abstract

A light-emitting device with high emission efficiency and low driving voltage is provided. A light-emitting apparatus, an electronic device, and a lighting device with low power consumption are provided. The following organic compound is provided: the organic compound has an arylamine structure; and when the organic compound is deposited to be a film, the ordinary refractive index of the deposited film with respect to light with a wavelength of 458 nm is greater than or equal to 1.50 and less than or equal to 1.75, the birefringence Δn of the deposited film with respect to light with a wavelength of 458 nm is greater than or equal to 0 and less than or equal to 0.008, or the alignment order parameter of the deposited film with respect to light with a wavelength corresponding to the longest wavelength where an absorption peak appears in the absorption spectrum is greater than or equal to −0.07 and less than or equal to 0.00.

Claims (146)

1 . 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 light-emitting layer and a hole-transport region,

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

wherein the hole-transport region comprises an organic compound,

wherein the organic compound comprises an arylamine structure, and

wherein when the organic compound is formed into a deposited film, an ordinary refractive index of the deposited film with respect to light with a wavelength of 458 nm is greater than or equal to 1.50 and less than or equal to 1.75, and a birefringence Δn of the deposited film with respect to light with a wavelength of 458 nm is greater than or equal to 0 and less than or equal to 0.008.

2 . 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 light-emitting layer and a hole-transport region,

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

wherein the hole-transport region comprises an organic compound,

wherein the organic compound comprises an arylamine structure, and

wherein when the organic compound is formed into a deposited film, an ordinary refractive index of the deposited film with respect to light with a wavelength of 458 nm is greater than or equal to 1.50 and less than or equal to 1.75, and an alignment order parameter of the deposited film with respect to light with a wavelength corresponding to a longest wavelength where an absorption peak appears in an absorption spectrum is greater than or equal to −0.07 and less than or equal to 0.00.

3 . The light-emitting device according to claim 1 ,

wherein a group comprising a para-biphenyl structure is bonded to at least one of nitrogen atoms of amine of the arylamine structure in the organic compound.

4 . The light-emitting device according to claim 2 ,

wherein a group comprising a para-biphenyl structure is bonded to at least one of nitrogen atoms of amine of the arylamine structure in the organic compound.

5 . 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 light-emitting layer and a hole-transport region,

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

wherein the hole-transport region comprises an organic compound,

wherein the organic compound comprises an arylamine structure,

wherein when the organic compound is formed into a deposited film, an ordinary refractive index of the deposited film with respect to light with a wavelength of 458 nm is greater than or equal to 1.50 and less than or equal to 1.75, and a birefringence Δn of the deposited film with respect to light with a wavelength of 458 nm is greater than or equal to 0 and less than or equal to 0.04, and

wherein a 1,1′-biphenyl-4-yl group is bonded to a nitrogen atom of amine in the organic compound.

6 . 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 light-emitting layer and a hole-transport region,

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

wherein the hole-transport region comprises an organic compound,

wherein the organic compound comprises an arylamine structure,

wherein when the organic compound is formed into a deposited film, an ordinary refractive index of the deposited film with respect to light with a wavelength of 458 nm is greater than or equal to 1.50 and less than or equal to 1.75, and an alignment order parameter of the deposited film with respect to light with a wavelength corresponding to a longest wavelength where an absorption peak appears in an absorption spectrum is greater than or equal to −0.10 and less than or equal to 0.00, and

wherein a 1,1′-biphenyl-4-yl group is bonded to a nitrogen atom of amine in the organic compound.

7 . The light-emitting device according to claim 5 ,

wherein the organic compound comprises at least one of an alkyl group having 3 to 8 carbon atoms and a cycloalkyl group having 6 to 12 carbon atoms in at least one of 2′-, 3′-, 4′-, and 5′-positions in the 1,1′-biphenyl-4-yl group.

8 . The light-emitting device according to claim 6 ,

wherein the organic compound comprises at least one of an alkyl group having 3 to 8 carbon atoms and a cycloalkyl group having 6 to 12 carbon atoms in at least one of 2′-, 3′-, 4′-, and 5′-positions in the 1,1′-biphenyl-4-yl group.

9 . The light-emitting device according to claim 7 ,

wherein the organic compound comprises a tert-butyl group in the 3′- and 5′-positions in the 1,1′-biphenyl-4-yl group.

10 . The light-emitting device according to claim 8 ,

wherein the organic compound comprises a tert-butyl group in the 3′- and 5′-positions in the 1,1′-biphenyl-4-yl group.

11 . The light-emitting device according to claim 5 ,

wherein benzene rings in one or a plurality of aniline structures included in the arylamine structure each independently comprise a substituent in a para-position in the organic compound.

12 . The light-emitting device according to claim 6 ,

wherein benzene rings in one or a plurality of aniline structures included in the arylamine structure each independently comprise a substituent in a para-position in the organic compound.

13 . The light-emitting device according to claim 3 ,

wherein one of benzene rings in a plurality of aniline structures included in the arylamine structure comprises a cyclohexyl group in a para-position in the organic compound.

14 . The light-emitting device according to claim 4 ,

wherein one of benzene rings in a plurality of aniline structures included in the arylamine structure comprises a cyclohexyl group in a para-position in the organic compound.

15 . The light-emitting device according to claim 11 ,

wherein one of the benzene rings in the plurality of aniline structures included in the arylamine structure comprises a cyclohexyl group in a para-position in the organic compound.

16 . The light-emitting device according to claim 12 ,

wherein one of the benzene rings in the plurality of aniline structures included in the arylamine structure comprises a cyclohexyl group in a para-position in the organic compound.

17 . The light-emitting device according to claim 3 ,

wherein one of benzene rings in a plurality of aniline structures included in the arylamine structure comprises a phenyl group in an ortho-position in the organic compound.

18 . The light-emitting device according to claim 4 ,

wherein one of benzene rings in a plurality of aniline structures included in the arylamine structure comprises a phenyl group in an ortho-position in the organic compound.

19 . The light-emitting device according to claim 11 ,

wherein one of the benzene rings in the plurality of aniline structures included in the arylamine structure comprises a phenyl group in an ortho-position in the organic compound.

20 . The light-emitting device according to claim 12 ,

wherein one of the benzene rings in the plurality of aniline structures included in the arylamine structure comprises a phenyl group in an ortho-position in the organic compound.

21 . The light-emitting device according to claim 1 ,

wherein a fluorenyl group is bonded to a nitrogen atom of amine of the arylamine structure in the organic compound.

22 . The light-emitting device according to claim 2 ,

wherein a fluorenyl group is bonded to a nitrogen atom of amine of the arylamine structure in the organic compound.

23 . The light-emitting device according to claim 5 ,

wherein a fluorenyl group is bonded to a nitrogen atom of amine of the arylamine structure in the organic compound.

24 . The light-emitting device according to claim 6 ,

wherein a fluorenyl group is bonded to a nitrogen atom of amine of the arylamine structure in the organic compound.

25 . The light-emitting device according to claim 1 ,

wherein the organic compound is a monoamine compound.

26 . The light-emitting device according to claim 2 ,

wherein the organic compound is a monoamine compound.

27 . The light-emitting device according to claim 5 ,

wherein the organic compound is a monoamine compound.

28 . The light-emitting device according to claim 6 ,

wherein the organic compound is a monoamine compound.

29 . The light-emitting device according to claim 1 ,

wherein the hole-transport region comprises a hole-injection layer and a hole-transport layer,

wherein the hole-injection layer is between the anode and the hole-transport layer, and

wherein the organic compound is included in at least one of the hole-injection layer and the hole-transport layer.

30 . The light-emitting device according to claim 2 ,

wherein the hole-transport region comprises a hole-injection layer and a hole-transport layer,

wherein the hole-injection layer is between the anode and the hole-transport layer, and

wherein the organic compound is included in at least one of the hole-injection layer and the hole-transport layer.

31 . The light-emitting device according to claim 5 ,

wherein the hole-transport region comprises a hole-injection layer and a hole-transport layer,

wherein the hole-injection layer is between the anode and the hole-transport layer, and

wherein the organic compound is included in at least one of the hole-injection layer and the hole-transport layer.

32 . The light-emitting device according to claim 6 ,

wherein the hole-transport region comprises a hole-injection layer and a hole-transport layer,

wherein the hole-injection layer is between the anode and the hole-transport layer, and

wherein the organic compound is included in at least one of the hole-injection layer and the hole-transport layer.

33 . The light-emitting device according to claim 29 ,

wherein a substance exhibiting an acceptor property is included in the hole-injection layer.

34 . The light-emitting device according to claim 30 ,

wherein a substance exhibiting an acceptor property is included in the hole-injection layer.

35 . The light-emitting device according to claim 31 ,

wherein a substance exhibiting an acceptor property is included in the hole-injection layer.

36 . The light-emitting device according to claim 32 ,

wherein a substance exhibiting an acceptor property is included in the hole-injection layer.

37 . An electronic apparatus comprising:

the light-emitting device according to claim 1 ; and

a sensor, an operation button, speaker, or a microphone.

38 . An electronic apparatus comprising:

the light-emitting device according to claim 2 ; and

a sensor, an operation button, speaker, or a microphone.

39 . An electronic apparatus comprising:

the light-emitting device according to claim 5 ; and

a sensor, an operation button, speaker, or a microphone.

40 . An electronic apparatus comprising:

the light-emitting device according to claim 6 ; and

a sensor, an operation button, speaker, or a microphone.

41 . A light-emitting apparatus comprising:

the light-emitting device according to claim 1 ; and

a transistor or a substrate.

42 . A light-emitting apparatus comprising:

the light-emitting device according to claim 2 ; and

a transistor or a substrate.

43 . A light-emitting apparatus comprising:

the light-emitting device according to claim 5 ; and

a transistor or a substrate.

44 . A light-emitting apparatus comprising:

the light-emitting device according to claim 6 ; and

a transistor or a substrate.

45 . A lighting device comprising:

the light-emitting device according to claim 1 ; and

a housing.

46 . A lighting device comprising:

the light-emitting device according to claim 2 ; and

a housing.

47 . A lighting device comprising:

the light-emitting device according to claim 5 ; and

a housing.

48 . A lighting device comprising:

the light-emitting device according to claim 6 ; and

a housing.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 28, 2021
From: OHSAWA, NOBUHARU; SEO, SATOSHI; WATABE, TAKEYOSHI; UEDA, AIRI; KUBOTA, TOMOHIRO; HIRAHARA, TAKASHI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 057621/0538 →
Priority Claims (2)
JP 2020-149062 · Sep 4, 2020 · national
JP 2021-011706 · Jan 28, 2021 · national
Continuity (1)
Related Publication 20220077391A1 · Mar 10, 2022
References Cited (46)
US 8642190B2 · Ogita et al. · 2014 [cited by applicant]
US 9051239B2 · Osaka et al. · 2015 [cited by applicant]
US 9496503B2 · Takeda et al. · 2016 [cited by applicant]
US 9634263B2 · Ogita et al. · 2017 [cited by applicant]
US 9818984B2 · Mizuno · 2017 [cited by applicant]
US 10556864B2 · Nomura et al. · 2020 [cited by applicant]
US 10941108B2 · Jeong et al. · 2021 [cited by applicant]
US 11964928B2 · Kubota et al. · 2024 [cited by applicant]
US 12139446B2 · Seo et al. · 2024 [cited by applicant]
US 12460130B2 · Kubota et al. · 2025 [cited by applicant]
US 20090160323A1 · Nomura et al. · 2009 [cited by applicant]
US 20100104969A1 · Mochizuki et al. · 2010 [cited by applicant]
US 20150207075A1 · Mujica-fernaud. et al. · 2015 [cited by applicant]
US 20160111653A1 · Itoi · 2016 [cited by applicant]
US 20180009751A1 · Nomura et al. · 2018 [cited by applicant]
US 20190016666A1 · Jeong et al. · 2019 [cited by applicant]
US 20200176692A1 · Watabe et al. · 2020 [cited by applicant]
US 20200235297A1 · Miyake et al. · 2020 [cited by applicant]
US 20210005814A1 · Watabe et al. · 2021 [cited by applicant]
US 20210202843A1 · Qian et al. · 2021 [cited by applicant]
US 20220158095A1 · Huang et al. · 2022 [cited by applicant]
CN 102437290A · 2012 [cited by applicant]
CN 110240546A · 2019 [cited by applicant]
CN 110373183A · 2019 [cited by applicant]
CN 110950762A · 2020 [cited by applicant]
CN 111233764A · 2020 [cited by applicant]
CN 111533716A · 2020 [cited by applicant]
CN 111548278A · 2020 [cited by applicant]
JP 11162649A · 1999 [cited by applicant]
JP 11282181A · 1999 [cited by applicant]
JP 2005120030A · 2005 [cited by applicant]
JP 2009091304A · 2009 [cited by applicant]
JP 2014207356A · 2014 [cited by applicant]
JP 2018181916A · 2018 [cited by applicant]
JP 2019505566 · 2019 [cited by applicant]
KR 20160127429A · 2016 [cited by applicant]
KR 20170080432A · 2017 [cited by applicant]
KR 20180137315A · 2018 [cited by applicant]
KR 20200092211A · 2020 [cited by applicant]
WO WO2017116167 · 2017 [cited by applicant]
WO WO2017116168 · 2017 [cited by applicant]
WO WO2019220276 · 2019 [cited by applicant]
WO WO2020259078 · 2020 [cited by applicant]
Machine English translation of Shimamura et al. (JP 11-162649 A). Feb. 2, 2026. [cited by examiner]
Taiwanese Office Action (Application No. 110131649) dated Dec. 31, 2024. [cited by applicant]
Lee.J et al., “Synergetic electrode architecture for efficient graphene-based flexible organic light-emitting diodes”, Nature Communications, Jun. 2, 2016, vol. 7, pp. 11791-1-11791-9. [cited by applicant]