Organic Compound, Light-Emitting Element, Display Module, Lighting Module, Light-Emitting Device, Display Device, Electronic Device, and Lighting Device

• US 20150243892A1
• Filed: 02/19/2015
• Published: 08/27/2015
• Est. Priority Date: 02/21/2014
• Status: Abandoned Application

• Current Assignee: Semiconductor Energy Laboratory Co., Ltd.
• Original Assignee: Semiconductor Energy Laboratory Co., Ltd.
• Inventors: Ogita, Kaori, Suzuki, Tsunenori, Hashimoto, Naoaki, Seo, Satoshi, Hamada, Toshiki, Suzuki, Kunihiko, Hosoumi, Shunsuke
• Application Number:
  US14/625,834
• Publication Number:
  US 20150243892A1
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: C07C 211/61 with at least one of the condensed ring systems formed by three or more rings
• CPC Class Codes: C07C 2603/18 Fluorenes; Hydrogenated fluorenes
• CPC Class Codes: C07C 2603/50 Pyrenes; Hydrogenated pyrenes
• CPC Class Codes: C07D 307/91 Dibenzofurans; Hydrogenated dibenzofurans
• CPC Class Codes: H10K 2101/20 Delayed fluorescence emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/6574 comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes

Abstract

A light-emitting element with high emission efficiency. The light-emitting element includes a pair of electrodes and an EL layer between the pair of electrodes. In the light-emitting element, the EL layer contains at least a light-emitting material, the light-emitting material is a 1,6-bis(diphenylamino)pyrene derivative, and a structural change between an excited state and a ground state in the 1,6-bis(diphenylamino)pyrene derivative is smaller than that in a 1,6-bis(diphenylamino)pyrene derivative in which hydrogen is bonded to ortho positions of two phenyl groups of each of two diphenylamino groups.

Claims

1. A light-emitting element comprising:

a pair of electrodes; and

an EL layer between the pair of electrodes;

wherein the EL layer comprises at least a light-emitting material,

wherein the light-emitting material is a 1,6-bis(diphenylamino)pyrene derivative, and

wherein a structural change between an excited state and a ground state in the 1,6-bis(diphenylamino)pyrene derivative is smaller than that in a 1,6-bis(diphenylamino)pyrene derivative in which hydrogen is bonded to ortho positions of two phenyl groups of each of two diphenylamino groups.

2. The light-emitting element according to claim 1,

wherein the 1,6-bis(diphenylamino)pyrene derivative comprises two diphenylamino groups,

wherein each of the two diphenylamino groups comprises two phenyl groups,

wherein an alkyl group is bonded to each of two ortho positions of one of the two phenyl groups, and

wherein hydrogen is bonded to each of two ortho positions of the other of the two phenyl groups.

3. The light-emitting element according to claim 1, wherein a Stokes shift of the light-emitting material is less than or equal to 0.18 eV.

4. The light-emitting element according to claim 1,

wherein the EL layer further comprises a host material,

wherein the light-emitting material is dispersed in the host material, and

wherein an absorption spectrum peak of the light-emitting material on the longest wavelength side overlaps with an emission spectrum of the host material.

5. A light-emitting element comprising:

a pair of electrodes; and

an EL layer between the pair of electrodes;

wherein the EL layer comprises at least a light-emitting material,

wherein the light-emitting material is a 1,6-bis(diphenylamino)pyrene derivative,

wherein the 1,6-bis(diphenylamino)pyrene derivative comprises two diphenylamino groups,

wherein each of the two diphenylamino groups comprises two phenyl groups, and

wherein an alkyl group is bonded to each of two ortho positions of at least one of the two phenyl groups.

6. The light-emitting element according to claim 5,

wherein a structural change between an excited state and a ground state in the 1,6-bis(diphenylamino)pyrene derivative is smaller than that in a 1,6-bis(diphenylamino)pyrene derivative in which hydrogen is bonded to ortho positions of two phenyl groups of each of two diphenylamino groups.

7. A light-emitting element according to claim 5,

wherein a Stokes shift of the 1,6-bis(diphenylamino)pyrene derivative is smaller than that of a 1,6-bis(diphenylamino)pyrene derivative in which hydrogen is bonded to ortho positions of two phenyl groups of each of two diphenylamino groups.

8. A light-emitting element according to claim 5,

wherein a half width of an emission spectrum of the 1,6-bis(diphenylamino)pyrene derivative is narrower than that of a 1,6-bis(diphenylamino)pyrene derivative in which hydrogen is bonded to ortho positions of two phenyl groups of each of two diphenylamino groups.

9. The light-emitting element according to claim 5, wherein a Stokes shift of the light-emitting material is less than or equal to 0.18 eV.

10. The light-emitting element according to claim 5,

wherein the EL layer further comprises a host material,

wherein the light-emitting material is dispersed in the host material, and

wherein an absorption spectrum peak of the light-emitting material on the longest wavelength side overlaps with an emission spectrum of the host material.

11. A 1,6-bis(diphenylamino)pyrene derivative comprising two diphenylamino groups,

wherein each of the two diphenylamino groups comprises two phenyl groups,

wherein an alkyl group is bonded to each of two ortho positions of at least one of the two phenyl groups, and

wherein a structural change between an excited state and a ground state in the 1,6-bis(diphenylamino)pyrene derivative is smaller than that in a 1,6-bis(diphenylamino)pyrene derivative in which hydrogen is bonded to ortho positions of two phenyl groups of each of two diphenylamino groups.

12. The 1,6-bis(diphenylamino)pyrene derivative according to claim 11, wherein in each of the two diphenylamino groups, an alkyl group is bonded to two ortho positions of one phenyl group, and hydrogen is bonded to two ortho positions of the other phenyl group.

13. The 1,6-bis(diphenylamino)pyrene derivative according to claim 11, wherein a Stokes shift of the 1,6-bis(diphenylamino)pyrene derivative is less than or equal to 0.18 eV.

14. The 1,6-bis(diphenylamino)pyrene derivative according to claim 11, wherein a half width of an emission spectrum of the 1,6-bis(diphenylamino)pyrene derivative is less than or equal to 40 nm.

15. The 1,6-bis(diphenylamino)pyrene derivative according to claim 11, wherein an emission peak wavelength of the 1,6-bis(diphenylamino)pyrene derivative is less than or equal to 465 nm.

16. An organic compound represented by General Formula (G1-2):

17. The organic compound according to claim 16, wherein the organic compound is represented by Structural formula (2100):

18. The organic compound according to claim 16, wherein the organic compound is represented by Structural formula (2200):

19. An organic compound represented by General Formula (G1-1):

20. The organic compound according to claim 19, wherein the organic compound is represented by Structural formula (1200):