Search

EP-4737462-A1 - ORGANIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE COMPRISING SAME

EP4737462A1EP 4737462 A1EP4737462 A1EP 4737462A1EP-4737462-A1

Abstract

The present invention relates to an organic light-emitting device including a plurality of host compounds in a light-emitting layer and employing a compound having a characteristic structure as one host material, thereby enabling low-voltage driving, and achieving significantly improved light-emitting efficiency and lifespan, resulting in high efficiency and long lifespan properties. Accordingly, the organic light-emitting device may be industrially utilized not only in lighting devices, but also in various display devices such as flat-panel, flexible and wearable displays, displays for vehicles or aviation, and displays for virtual or augmented reality.

Inventors

  • KIM, KYEONG-HYEON
  • KIM, JI-YUNG
  • KIM, SI-IN
  • JANG, Hyuk-woo
  • CHOI, DO-YEONG
  • PARK, Seo-youn
  • CHOI, Yeon-jae
  • KIM, Kyeong-wan
  • LEE, SE-JIN

Assignees

  • SFC Co., Ltd.

Dates

Publication Date
20260506
Application Date
20240730

Claims (15)

  1. An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes a light-emitting layer including a host and a dopant, the host includes a first compound and a second compound, and the first compound includes at least one organic compound represented by the following [Chemical Formula 1]: in [Chemical Formula 1], X 1 to X 3 are the same as or different from each other and each independently N or CR, and at least one of X 1 to X 3 is N; Z is Si or Ge; X is any one selected from O, S, NR 5 , CR 6 R 7 , SiR 8 R 9 and GeR 10 R 11 , R 1 and R 2 are the same as or different from each other, and each independently any one selected from a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 6 -C 50 aryl group, a substituted or unsubstituted C 3 -C 50 cycloalkyl group, a substituted or unsubstituted C 2 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, and a substituted or unsubstituted fused cyclic group of C 3 -C 30 aliphatic ring and C 3 -C 30 aromatic ring; R and R 3 to R 11 are the same as or different from each other, and each independently any one selected from hydrogen, deuterium, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 3 -C 50 cycloalkyl group, a substituted or unsubstituted C 2 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted fused cyclic group of C 3 -C 30 aliphatic ring and C 3 -C 30 aromatic ring, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 1 -C 30 alkylthioxy group, a substituted or unsubstituted C 5 -C 30 arylthioxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group; L 1 and L 2 are the same as or different from each other, and each independently any one selected from a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C 2 -C 30 heteroarylene group, and a substituted or unsubstituted fused divalent cyclic group of C 3 -C 24 aliphatic ring and C 3 -C 24 aromatic ring; A and B are the same as or different from each other, and each independently any one selected from a substituted or unsubstituted C 6 -C 30 aromatic hydrocarbon ring, a substituted or unsubstituted C 3 -C 30 aliphatic hydrocarbon ring, a substituted or unsubstituted C 2 -C 30 aromatic heteroring, a substituted or unsubstituted C 2 -C 30 aliphatic heteroring, and a substituted or unsubstituted fused ring of C 3 -C 24 aliphatic ring and C 3 -C 24 aromatic ring; m 1 and m 2 are each independently an integer of 1 to 3, and when each of m 1 and m 2 is an integer of 2 or greater, the respective R 1 s and R 2 s are the same as or different from each other; m 3 and m 4 are each independently an integer of 8, and the respective R 3 s and R 4 s are the same as or different from each other; n 1 andn 2 are each independently an integer of 1 to 3, and when each of n 1 andn 2 is an integer of 2 or greater, the respective L 1 s and L 2 s are the same as or different from each other; the plurality of adjacent R 3 s and R 4 s are optionally linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring; R 6 and R 7 , R 8 and R 9 , and R 10 and R 11 are optionally linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring; and the 'substituted' in the 'substituted or unsubstituted' in [Chemical Formula 1] means being substituted with one or more substituents selected from the group consisting of deuterium, a C 1 -C 24 alkyl group, a C 1 -C 24 halogenated alkyl group, a C 2 -C 24 alkenyl group, a C 2 -C 24 alkynyl group, a C 3 -C 30 cycloalkyl group, a C 1 -C 24 heteroalkyl group, a C 6 -C 30 aryl group, a C 7 -C 30 arylalkyl group, a C 7 -C 30 alkylaryl group, a C 2 -C 30 heteroaryl group, a C 2 -C 30 heteroarylalkyl group, a fused cyclic group of C 3 -C 24 aliphatic ring and C 3 -C 24 aromatic ring, a C 1 -C 24 alkoxy group, a C 1 -C 30 amine group, a C 1 -C 30 silyl group, a C 1 -C 30 germanium group, a C 6 -C 24 aryloxy group, a C 6 -C 24 arylthionyl group, a cyano group, a halogen group, a hydroxyl group and a nitro group, and when there are two or more substituents, they are the same as or different from each other, and at least one hydrogen in each of the substituents is optionally substituted with deuterium.
  2. The organic light-emitting device of claim 1, wherein the organic compound represented by [Chemical Formula 1] is represented by the following [Chemical Formula 1-1]: in [Chemical Formula 1-1], R 12 s are the same as or different from each other, and each independently any one selected from hydrogen, deuterium, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 3 -C 50 cycloalkyl group, a substituted or unsubstituted C 2 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 2 -C 50 heteroaryl group, a substituted or unsubstituted fused cyclic group of C 3 -C 30 aliphatic ring and C 5 -C 30 aromatic ring, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 1 -C 30 alkylthioxy group, a substituted or unsubstituted C 5 -C 30 arylthioxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group; m 5 is an integer of 3, and the respective R 12 s are the same as or different from each other; the plurality of adjacent R 12 s are optionally linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring; and X, X 1 to X 3 , Z, R 1 to R 4 , L 1 , L 2 , n 1 , n 2 , m 1 to m 4 , and ring B have the same definitions as in [Chemical Formula 1] of claim 1.
  3. The organic light-emitting device of claim 1, wherein L 1 and L 2 are the same as or different from each other, and each independently a substituted or unsubstituted C 6 -C 20 arylene group.
  4. The organic light-emitting device of claim 1, wherein R 1 and R 2 are the same as or different from each other, and each independently any one selected from a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, and a substituted or unsubstituted fused cyclic group of C 3 -C 18 aliphatic ring and C 3 -C 18 aromatic ring.
  5. The organic light-emitting device of claim 2, wherein B is a substituted or unsubstituted C 6 -C 20 aromatic hydrocarbon ring.
  6. The organic light-emitting device of claim 1, wherein X 1 to X 3 are all N.
  7. The organic light-emitting device of claim 1, wherein at least one hydrogen in the organic compound represented by [Chemical Formula 1] is substituted with deuterium.
  8. The organic light-emitting device of claim 7, wherein R 3 and R 4 in [Chemical Formula 1] are all deuterium atoms.
  9. The organic light-emitting device of claim 1, wherein X in [Chemical Formula 1] is O or S.
  10. The organic light-emitting device of claim 1, wherein [Chemical Formula 1] is any one selected from compounds represented by the following chemical formulae:
  11. The organic light-emitting device of claim 1, wherein the second compound in the host is used by mixing or laminating the first compound represented by [Chemical Formula 1] with at least one other compound.
  12. The organic light-emitting device of claim 1, wherein the organic compound represented by [Chemical Formula 1] used as the first compound in the host is used in a blue phosphorescent host.
  13. The organic light-emitting device of claim 1, wherein the dopant includes at least one organometallic compound.
  14. The organic light-emitting device of claim 13, wherein, in addition to the organometallic compound, a polycyclic compound represented by the following [Chemical Formula 2] is mixed or laminated and used: in [Chemical Formula 2], Y 1 and Y 2 are the same as or different from each other, and each independently any one selected from O, S, NR 13 , CR 14 R 15 , SiR 16 R 17 and GeR 18 R 19 ; A 1 to A 3 are the same as or different from each other, and each independently any one selected from a substituted or unsubstituted C 6 -C 30 aromatic hydrocarbon ring, a substituted or unsubstituted C 3 -C 30 aliphatic hydrocarbon ring, a substituted or unsubstituted C 2 -C 30 aromatic heteroring, a substituted or unsubstituted C 2 -C 30 aliphatic heteroring, and a substituted or unsubstituted fused ring of C 3 -C 24 aliphatic ring and C 3 -C 24 aromatic ring; R 13 to R 19 are the same as or different from each other, and each independently any one selected from hydrogen, deuterium, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 3 -C 50 cycloalkyl group, a substituted or unsubstituted C 2 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted fused cyclic group of C 3 -C 30 aliphatic ring and C 3 -C 30 aromatic ring, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 1 -C 30 alkylthioxy group, a substituted or unsubstituted C 5 -C 30 arylthioxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group; R 13 to R 19 are optionally linked to the rings A 1 to A 3 to further form an alicyclic or aromatic monocyclic or polycyclic ring; R 14 and R 13 , R 16 and R 17 , and R 18 and R 19 are each optionally linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring; and the 'substituted' in the 'substituted or unsubstituted' in [Chemical Formula 2] means being substituted with one or more substituents selected from the group consisting of deuterium, a C 1 -C 24 alkyl group, a C 1 -C 24 halogenated alkyl group, a C 2 -C 24 alkenyl group, a C 2 -C 24 alkynyl group, a C 3 -C 30 cycloalkyl group, a C 1 -C 24 heteroalkyl group, a C 6 -C 30 aryl group, a C 7 -C 30 arylalkyl group, a C 7 -C 30 alkylaryl group, a C 2 -C 30 heteroaryl group, a C 2 -C 30 heteroarylalkyl group, a fused cyclic group of C 3 -C 24 aliphatic ring and C 3 -C 24 aromatic ring, a C 1 -C 24 alkoxy group, a C 1 -C 30 amine group, a C 1 -C 30 silyl group, a C 1 -C 30 germanium group, a C 6 -C 24 aryloxy group, a C 6 -C 24 arylthionyl group, a cyano group, a halogen group, a hydroxyl group and a nitro group, and when there are two or more substituents, they are the same as or different from each other, and at least one hydrogen in each of the substituents is optionally substituted with deuterium.
  15. The organic light-emitting device of claim 10, which is used in any one device selected from flat-panel display devices; flexible display devices; monochromatic or white flat-panel lighting devices; monochromatic or white flexible lighting devices; display devices for vehicles and aviation; and display devices for virtual or augmented reality.

Description

[Technical Field] The present invention relates to an organic compound employed in a light-emitting layer in an organic light-emitting device, and an organic light-emitting device including the same. [Background Art] Organic light-emitting devices are self-luminous devices in which electrons injected from an electron injecting electrode (cathode) combine with holes injected from a hole injecting electrode (anode) in a light-emitting layer to form excitons, which emit light while releasing energy. Such organic light-emitting devices have advantages of low driving voltage, high luminance, wide viewing angle and short response time, and being applicable to full-color light-emitting flat-panel displays. Due to these advantages, organic light-emitting devices have received attention as next-generation light sources. The above characteristics of organic light-emitting devices are achieved by structural optimization of organic layers of the devices and are supported by stable and efficient materials for the organic layers, such as hole injecting materials, hole transport materials, hole blocking materials, light-emitting materials, electron transport materials, electron injecting materials, and electron blocking materials. However, more research still needs to be done to develop structurally optimized structures of organic layers for organic light-emitting devices and stable and efficient materials for organic layers of organic light-emitting devices. Particularly, to obtain maximum efficiency in a light-emitting layer, an appropriate combination of energy band gaps of a host and a dopant is required so that holes and electrons each migrate to the dopant through stable electrochemical paths to form excitons. [Detailed Description of the Invention] [Problems to be Solved by the Invention] Accordingly, the present invention is directed to providing a light-emitting layer host material having a characteristic structure, and a high-efficiency and long-lifespan organic light-emitting device having low-voltage driving, and significantly improved light-emitting efficiency and lifespan by including the host material. [Means for Solving the Problems] In order to resolve the above-described problems, one aspect of the present invention provides an organic light-emitting device including: a first electrode; a second electrode provided opposite to the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes a light-emitting layer including a host and a dopant, the host includes a first compound and a second compound, and the first compound includes at least one organic compound represented by the following [Chemical Formula 1]. Specific structures of [Chemical Formula 1], specific compounds according to the present invention obtained therefrom, and a definition of each substituent will be described later. [Effects of the Invention] An organic light-emitting device according to the present invention includes a plurality of host compounds in a light-emitting layer and employs a compound having a characteristic structure as one host material, thereby achieving properties of high efficiency and long lifespan having low-voltage driving, and significantly improved light-emitting efficiency and lifespan. Accordingly, the organic light-emitting device can be effectively utilized not only in lighting devices, but also in various display devices such as flat-panel, flexible and wearable displays, displays for vehicles or aviation, and displays for virtual or augmented reality. [Best Mode for Carrying out the Invention] Hereinafter, the present invention will be described in more detail. One aspect of the present invention relates to an organic light-emitting device including: a first electrode; a second electrode provided opposite to the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes a light-emitting layer including a host and a dopant, the host includes a first compound and a second compound, and the first compound includes at least one organic compound represented by the following [Chemical Formula 1]. Herein, the first compound represented by [Chemical Formula 1] is an organic compound having a structure in which a benzene derivative skeleton including nitrogen is substituted with two carbazole groups and a silyl group substituted with a characteristic substituent. Due to such characteristics, a high-efficiency and long-lifespan organic light-emitting device having low-voltage driving, and significantly improved light-emitting efficiency and lifespan may be achieved by including a plurality of host compounds in a light-emitting layer and employing the compound of the following [Chemical Formula 1] having a characteristic structure as one host material. In [Chemical Formula 1], X1 to X3 are the same as or different from each other and each independently N or CR, at