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EP-4737463-A1 - ORGANIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE COMPRISING SAME

EP4737463A1EP 4737463 A1EP4737463 A1EP 4737463A1EP-4737463-A1

Abstract

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. When employing the compound according to the present invention as a host of a light-emitting layer, 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. 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.

Inventors

  • KIM, KYEONG-HYEON
  • 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 (12)

  1. An organic compound represented by the following [Chemical Formula 1]: wherein, in [Chemical Formula 1], R 1 to R 8 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 6 -C 50 aryl group, a substituted or unsubstituted C 3 -C 50 cycloalkyl group, a substituted or unsubstituted C 2 -C 50 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, and the following [Structural Formula b] to [Structural Formula f]; at least one of R 1 to R 8 is any one selected from [Structural Formula b] to [Structural Formula f]; and at least one of R 9 to R 11 is the following [Structural Formula a], and the rest are the same as or different from each other and each independently any one selected from hydrogen and deuterium; in [Structural Formula a] to [Structural Formula f], R 12 to R 14 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 6 -C 50 aryl group, a substituted or unsubstituted C 3 -C 50 cycloalkyl group, a substituted or unsubstituted C 2 -C 50 heterocycloalkyl group, a substituted or unsubstituted C 2 -C 50 heteroaryl group, and a substituted or unsubstituted fused cyclic group of C 3 -C 30 aliphatic ring and C 5 -C 30 aromatic ring; L 1 is any one selected from O, S, a substituted or unsubstituted arylene group, and a substituted or unsubstituted heteroarylene group; m is an integer of 1 to 3, and when m is 2 or greater, a plurality of L 1 s are the same as or different from each other; * in [Structural Formula a] indicates a position bonding to any one of R 9 to R 11 , and * in [Structural Formula b] indicates a position bonding to any one of R 1 to R 8 ; Ys are the same as or different from each other and each independently CR 18 or N, and X is any one selected from NR 19 , O, S and SiR 20 R 21 ; Z is any one selected from NR 22 , O and S; however, (i) when X is NR 19 and Y is CR 18 in [Structural Formula d], L 1 in [Structural Formula a] is O or S, and (ii) when X is NR 19 , Y is CR 18 and Z is NR 22 in [Structural Formula f], L 1 in [Structural Formula a] is O or S; L 2 is any one selected from a single bond, a substituted or unsubstituted C 3 -C 30 aryl group and a substituted or unsubstituted C 3 -C 30 heteroaryl group; n is an integer of 0 to 2, and when n is 2 or greater, a plurality of L 2 s are the same as or different from each other; at least one of R 18 to R 22 is linked to R 1 to R 8 , and the rest 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 6 -C 50 aryl group, a substituted or unsubstituted C 3 -C 50 cycloalkyl group, a substituted or unsubstituted C 2 -C 50 heterocycloalkyl group, a substituted or unsubstituted C 2 -C 50 heteroaryl group, and a substituted or unsubstituted fused cyclic group of C 3 -C 30 aliphatic ring and C 5 -C 30 aromatic ring; and the 'substituted' in the 'substituted or unsubstituted' means being substituted with one or more same or different substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, a C 1 -C 24 alkyl group, a C 1 -C 24 halogenated alkyl group, a C 1 -C 24 alkenyl group, a C 1 -C 24 alkynyl group, a C 3 -C 30 cycloalkyl group, a C 1 -C 24 heteroalkyl group, a C 6 -C 24 aryl group, a C 6 -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 30 aliphatic ring and C 5 -C 30 aromatic ring, a C 1 -C 24 alkoxy group, a C 0 -C 30 amine group, a C 1 -C 30 silyl group, a C 1 -C 30 germanium group, a C 1 -C 24 aryloxy group and a C 6 -C 24 arylthionyl group, and at least one hydrogen in each of the substituents is optionally substituted with deuterium.
  2. The organic compound of claim 1, wherein [Chemical Formula 1] is any one selected from compounds represented by the following chemical formulae:
  3. The organic compound of claim 1, wherein at least one of R 1 to R 8 is any one selected from [Structural Formula b] to [Structural Formula f], and the rest of R 1 to R 8 not selected are hydrogen or deuterium.
  4. The organic compound of claim 3, wherein R 2 or R 7 is any one selected from [Structural Formula b] to [Structural Formula f].
  5. The organic compound of claim 3, wherein R 2 and R 7 are any one selected from [Structural Formula b] to [Structural Formula f].
  6. The organic compound of claim 1, wherein R 12 to R 14 are the same as or different from each other, and each independently a substituted or unsubstituted C 6 -C 50 aryl group or a substituted or unsubstituted C 2 -C 50 heteroaryl group.
  7. 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, and the host includes at least one organic compound represented by [Chemical Formula 1] of claim 1.
  8. The organic light-emitting device of claim 7, wherein the host is used by mixing or laminating one or more other compounds in addition to the at least one organic compound represented by [Chemical Formula 1].
  9. The organic light-emitting device of claim 8, wherein the organic compound represented by [Chemical Formula 1] used in the host is used in a blue phosphorescent host.
  10. The organic light-emitting device of claim 9, wherein the dopant includes at least one organometallic compound.
  11. The organic light-emitting device of claim 10, wherein, in addition to the organometallic compound, a polycyclic compound represented by the following [Chemical Formula 3] is mixed or laminated, and used: in [Chemical Formula 3], Y 1 and Y 2 are the same as or different from each other, and each independently any one selected from O, S, NR 27 , CR 28 R 29 , SiR 30 R 31 and GeR 32 R 33 ; rings 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 5 -C 24 aromatic ring; R 27 to R 33 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 50 aryl group, a substituted or unsubstituted C 3 -C 50 cycloalkyl group, a substituted or unsubstituted C 2 -C 50 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; R 27 to R 33 are optionally linked to the rings A 1 to A 3 to further form an alicyclic or aromatic monocyclic or polycyclic ring; R 28 and R 29 , R 30 and R 31 , and R 32 and R 33 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 3] 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 5 -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.
  12. The organic light-emitting device of claim 7, 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 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 significantly improved lifespan and light-emitting efficiency 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 compound represented by the following [Chemical Formula 1], and an organic light-emitting device including the same as a host in a light-emitting layer. In [Chemical Formula 1], (i) at least one of R1 to R8 is any one selected from the following [Structural Formula b] to [Structural Formula f], and(ii) at least one of R9 to R11 is the following [Structural Formula a]. Specific structures of [Chemical Formula 1], [Structural Formula a] and [Structural Formula b] to [Structural Formula f], specific compounds according to the present invention obtained therefrom, and a definition of each substituent will be described later. [Effects of the Invention] 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. When employing the compound according to the present invention as a host of a light-emitting layer, a high-efficiency and long-lifespan organic light-emitting device having low-voltage driving, and significantly improved light-emitting efficiency and lifespan can be achieved. Accordingly, the organic compound and 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. [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 a compound represented by the following [Chemical Formula 1]. In [Chemical Formula 1], R1 to R8 are the same as or different from each other, and each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted fused cyclic group of C3-C30 aliphatic ring and C5-C30 aromatic ring, and the following [Structural Formula b] to [Structural Formula f]. However, herein, at least one of R1 to R8 is any one selected from the following [Structural Formula b] to [Structural Formula f]. In addition, at least one of R9 to R11 is the following [Structural Formula a], and the rest are the same as or different from each other and each independently hydrogen or deuterium. In [Structural Formula a] to [Structural Formula f], R12 to R14 are the same as or different from each other, and each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstit