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CN-122010982-A - Polycyclic compound, light-emitting device, electronic device, and electronic apparatus

CN122010982ACN 122010982 ACN122010982 ACN 122010982ACN-122010982-A

Abstract

The application relates to a polycyclic compound, a light-emitting device, an electronic device, and an electronic apparatus. The polycyclic compound may be represented by chemical formula 1. All variables in chemical formula 1 are described herein. The light emitting device may include a polycyclic compound, the electronic device may include a light emitting device, and the electronic apparatus may include a light emitting device. The light emitting device includes a first electrode, a second electrode, and an intermediate layer between the first electrode and the second electrode. The intermediate layer includes an emissive layer and an organic layer. At least one of the emission layer and the organic layer includes a polycyclic compound represented by chemical formula 1. [ chemical formula 1]

Inventors

  • Ren Zixian
  • Quan Zhanghe
  • JIN ZHENYONG
  • Subramanian Muruga Nansam
  • An Xizhu
  • CAI MEIRONG
  • DENG HAICHUAN
  • Shen Zhonggen
  • WU JUNHE

Assignees

  • 三星显示有限公司
  • 庆熙大学校产学协力团

Dates

Publication Date
20260512
Application Date
20251112
Priority Date
20241112

Claims (15)

  1. 1. A polycyclic compound represented by chemical formula 1: Chemical formula 1 Wherein in chemical formula 1, any one or two of Y 1 to Y 4 is C or N, and the remaining Y 1 to Y 4 are C, When Y 1 、Y 2 、Y 3 or Y 4 is N, k is 0, where k is the number of R 1 、R 2 、R 3 or R 4 bonded to Y 1 、Y 2 、Y 3 or Y 4 , When Y 1 、Y 2 、Y 3 or Y 4 is C, k is 1, R 1 to R 10 are each independently hydrogen, deuterium 、-OH、-CN、-F、-Cl、-Br、-I、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 、 amine group, substituted or unsubstituted C 1 -C 60 alkyl group, Substituted or unsubstituted C 2 -C 60 alkenyl, substituted or unsubstituted C 2 -C 60 alkynyl, substituted or unsubstituted C 1 -C 60 alkoxy, substituted or unsubstituted C 3 -C 60 cycloalkyl, Substituted or unsubstituted C 5 -C 60 cycloalkenyl, substituted or unsubstituted C 3 -C 60 heterocycloalkyl, substituted or unsubstituted C 3 -C 60 heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 aryl, Substituted or unsubstituted C 7 -C 60 aralkyl, substituted or unsubstituted C 2 -C 60 heteroaryl, substituted or unsubstituted C 3 -C 60 heteroaralkyl, substituted or unsubstituted C 6 -C 60 aryloxy, substituted or unsubstituted C 6 -C 60 arylthio, substituted or unsubstituted C 8 -C 60 fused polycyclic group or substituted or unsubstituted silyl, A plurality of n2 are each an integer selected from 0 to 2 and are the same as or different from each other, A plurality of n3 are each an integer selected from 0 to 3 and are the same as or different from each other, When n2 and n3 are integers of 1 or greater, two or more adjacent groups of R 5 to R 10 are optionally combined with each other to form a substituted or unsubstituted saturated or unsaturated ring, When any two, any three, or all four k are 1, two or more groups of any two, any three, or all four corresponding ones of R 1 to R 4 combine with each other to form at least one substituted or unsubstituted saturated or unsaturated ring, L 1 and L 2 are each independently a substituted or unsubstituted C 6 -C 60 arylene, a substituted or unsubstituted C 4 -C 60 heteroarylene, a substituted or unsubstituted C 6 -C 60 fused arylene or a substituted or unsubstituted C 4 -C 60 fused heteroarylene, and The aromatic ring groups including Y 1 to Y 4 directly bonded to L 1 and L 2 have a meta-or para-relationship with each other with the substituted or unsubstituted 1, 10-phenanthroline group directly bonded to L 1 or L 2 .
  2. 2. The polycyclic compound according to claim 1, wherein: R 1 and R 2 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or R 2 and R 3 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or R 3 and R 4 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or R 1 and R 2 are bonded to each other and R 3 and R 4 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring.
  3. 3. The polycyclic compound according to claim 1, wherein the group derived from the aromatic ring group including Y 1 to Y 4 is represented by any one of chemical formulas 2-1 to 2-41: Wherein in chemical formulas 2-1 to 2-41, a plurality of n1 are each 0 or 1 and are the same or different from each other, A plurality of n2 are each an integer selected from 0 to 2 and are the same as or different from each other, A plurality of n3 are each an integer selected from 0 to 3 and are the same as or different from each other, A plurality of n4 are each an integer selected from 0 to 4 and are the same as or different from each other, Each R a is independently hydrogen, deuterium 、-OH、-CN、-F、-Cl、-Br、-I、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 、 amine, substituted or unsubstituted C 1 -C 60 alkyl, substituted or unsubstituted C 2 -C 60 alkenyl, Substituted or unsubstituted C 2 -C 60 alkynyl, substituted or unsubstituted C 1 -C 60 alkoxy, substituted or unsubstituted C 3 -C 60 cycloalkyl, substituted or unsubstituted C 5 -C 60 cycloalkenyl, Substituted or unsubstituted C 3 -C 60 heterocycloalkyl, substituted or unsubstituted C 3 -C 60 heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 aryl, substituted or unsubstituted C 7 -C 60 aralkyl, Substituted or unsubstituted C 2 -C 60 heteroaryl, substituted or unsubstituted C 3 -C 60 heteroarylalkyl, substituted or unsubstituted C 6 -C 60 aryloxy, substituted or unsubstituted C 6 -C 60 arylthio, A substituted or unsubstituted C 8 -C 60 condensed polycyclic group or substituted or unsubstituted silyl group, two or more adjacent R a groups optionally being bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, and Two represent binding sites to L 1 and L 2 , respectively.
  4. 4. The polycyclic compound according to claim 3, wherein the group derived from the aromatic ring group including Y 1 to Y 4 is represented by any one of chemical formulas 2-31 to 2-41.
  5. 5. The polycyclic compound according to claim 1, wherein L 1 and L 2 are each independently represented by any one of chemical formulas 3-1 to 3-44: wherein in chemical formulas 3-1 to 3-44, a plurality of n1 are each 0 or 1 and are the same or different from each other, A plurality of n2 are each an integer selected from 0 to 2 and are the same as or different from each other, A plurality of n3 are each an integer selected from 0 to 3 and are the same as or different from each other, A plurality of n4 are each an integer selected from 0 to 4 and are the same as or different from each other, Each R b is independently hydrogen, deuterium 、-OH、-CN、-F、-Cl、-Br、-I、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 、 amine, substituted or unsubstituted C 1 -C 60 alkyl, substituted or unsubstituted C 2 -C 60 alkenyl, Substituted or unsubstituted C 2 -C 60 alkynyl, substituted or unsubstituted C 1 -C 60 alkoxy, substituted or unsubstituted C 3 -C 60 cycloalkyl, substituted or unsubstituted C 5 -C 60 cycloalkenyl, Substituted or unsubstituted C 3 -C 60 heterocycloalkyl, substituted or unsubstituted C 3 -C 60 heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 aryl, substituted or unsubstituted C 7 -C 60 aralkyl, Substituted or unsubstituted C 2 -C 60 heteroaryl, substituted or unsubstituted C 3 -C 60 heteroarylalkyl, substituted or unsubstituted C 6 -C 60 aryloxy, substituted or unsubstituted C 6 -C 60 arylthio, A substituted or unsubstituted C 8 -C 60 condensed polycyclic group or substituted or unsubstituted silyl group, two or more adjacent R b groups optionally being bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, and One of the two is a bonding site to a group derived from the aromatic ring group comprising Y 1 to Y 4 , and the other of the two is a bonding site to the substituted or unsubstituted 1, 10-phenanthroline group.
  6. 6. The polycyclic compound according to claim 1, wherein the polycyclic compound is represented by any one of chemical formulas 4-1 to 4-13: wherein in chemical formulas 4-1 to 4-13, a plurality of n2 are each an integer selected from 0 to 2 and are the same or different from each other, A plurality of n3 are each an integer selected from 0 to 3 and are the same as or different from each other, A plurality of n4 are each an integer selected from 0 to 4 and are the same as or different from each other, Each X is independently CH, CD or N, and Each R c is independently hydrogen, deuterium 、-OH、-CN、-F、-Cl、-Br、-I、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 、 amine, substituted or unsubstituted C 1 -C 60 alkyl, substituted or unsubstituted C 2 -C 60 alkenyl, Substituted or unsubstituted C 2 -C 60 alkynyl, substituted or unsubstituted C 1 -C 60 alkoxy, substituted or unsubstituted C 3 -C 60 cycloalkyl, substituted or unsubstituted C 5 -C 60 cycloalkenyl, Substituted or unsubstituted C 3 -C 60 heterocycloalkyl, substituted or unsubstituted C 3 -C 60 heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 aryl, substituted or unsubstituted C 7 -C 60 aralkyl, Substituted or unsubstituted C 2 -C 60 heteroaryl, substituted or unsubstituted C 3 -C 60 heteroarylalkyl, substituted or unsubstituted C 6 -C 60 aryloxy, substituted or unsubstituted C 6 -C 60 arylthio, a substituted or unsubstituted C 8 -C 60 fused polycyclic group or substituted or unsubstituted silyl group, and two or more adjacent R c are optionally combined with each other to form a substituted or unsubstituted saturated or unsaturated ring.
  7. 7. The polycyclic compound according to claim 6, wherein the polycyclic compound is represented by any one of chemical formulas 4-1 to 4-6.
  8. 8. A light emitting device, comprising: A first electrode; A second electrode, and An intermediate layer between the first electrode and the second electrode, the intermediate layer comprising an emissive layer and an organic layer, Wherein at least one of the emissive layer and the organic layer comprises the polycyclic compound according to any one of claims 1 to 7.
  9. 9. The light-emitting device according to claim 8, wherein the intermediate layer comprises a light-emitting structure comprising: a hole transfer region including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer; An emissive layer, and An electron transfer region including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer, Wherein at least one of the hole transfer region, the emission layer, and the electron transfer region includes the polycyclic compound.
  10. 10. The light-emitting device according to claim 9, wherein the intermediate layer includes a plurality of light-emitting structures, and the intermediate layer includes a charge generation layer between adjacent light-emitting structures, and At least one of the emission layer and the charge generation layer includes the polycyclic compound.
  11. 11. The light-emitting device according to claim 9, wherein the emission layer comprises a first emission layer and a second emission layer, and the organic layer comprises a first hole injection layer, a first hole transport layer, a first electron transport layer, an n-type charge generation layer, a p-type charge generation layer, a second hole transport layer, a second electron transport layer, and a second electron injection layer, Wherein the first hole injection layer, the first hole transport layer, the first emission layer, the first electron transport layer, the n-type charge generation layer, the p-type charge generation layer, the second hole transport layer, the second emission layer, the second electron transport layer, and the second electron injection layer are stacked in this order in a direction from the first electrode to the second electrode.
  12. 12. The light-emitting device of claim 11, wherein at least one of the first electron transport layer, the first emission layer, the n-type charge generation layer, the second emission layer, and the second electron transport layer comprises the polycyclic compound.
  13. 13. The light-emitting device of claim 12, wherein at least two of the first electron transport layer, the n-type charge generation layer, and the second electron transport layer comprise the polycyclic compound.
  14. 14. An electronic device comprising the light-emitting device according to any one of claims 8 to 13.
  15. 15. An electronic device comprising the light emitting apparatus of any one of claims 8 to 13, wherein the electronic device is one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a heads-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a phone, a mobile phone, a tablet computer, a personal information terminal, a wearable apparatus, a laptop computer, a digital camera, a video camera, a viewfinder, a micro display, a 3D display, a virtual reality display, an augmented reality display, a vehicle, a video wall comprising a plurality of displays stitched together, a theatre screen, a stadium screen, a phototherapy apparatus, and a logo.

Description

Polycyclic compound, light-emitting device, electronic device, and electronic apparatus Cross Reference to Related Applications The present application claims priority from korean patent application No. 10-2024-0160532 filed in the Korean Intellectual Property Office (KIPO) on day 11 and 12 of 2024, the entire disclosure of which is incorporated herein by reference. Technical Field Aspects of the present disclosure relate to polycyclic compounds, light emitting devices, electronic devices, and electronic apparatuses. Background The organic light emitting device has self-luminescence characteristics and can provide improved viewing angle and contrast characteristics. In addition, a high response speed and high brightness can be provided. The organic light emitting device may include an intermediate layer including an emission layer disposed between the first electrode and the second electrode. The intermediate layer may further comprise an organic layer. Holes moving from the first electrode and electrons moving from the second electrode may recombine in the emissive layer to generate excitons. When the exciton is shifted from the excited state to the ground state, light emission characteristics are achieved. The heterocyclic compound containing a heteroatom may have different characteristics according to chemical structures, and may be applied to various layers as a material for an organic light emitting device. Disclosure of Invention According to aspects of the present disclosure, polycyclic compounds having improved electron transfer properties and lifetime properties are provided. According to aspects of the present disclosure, a light emitting device having improved light emission characteristics (e.g., light emission efficiency) and lifetime characteristics is provided. According to aspects of the present disclosure, an electronic device including a light emitting device is provided. According to aspects of the present disclosure, an electronic apparatus including a light emitting device is provided. A polycyclic compound represented by chemical formula 1 is provided. [ Chemical formula 1] In chemical formula 1, any one or two of Y 1 to Y 4 is C or N, and the remaining Y 1 to Y 4 are C. When Y 1、Y2、Y3 or Y 4 is N, k, which is the number of R 1、R2、R3 or R 4 bonded to Y 1、Y2、Y3 or Y 4, is 0. When Y 1、Y2、Y3 or Y 4 is C, k, which is the number of R 1、R2、R3 or R 4 bonded to Y 1、Y2、Y3 or Y 4, is 1. R 1 to R 10 are each independently hydrogen, deuterium 、-OH、-CN、-F、-Cl、-Br、-I、-CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2、 amine group, substituted or unsubstituted C 1-C60 alkyl group, Substituted or unsubstituted C 2-C60 alkenyl, substituted or unsubstituted C 2-C60 alkynyl, substituted or unsubstituted C 1-C60 alkoxy, substituted or unsubstituted C 3-C60 cycloalkyl, Substituted or unsubstituted C 5-C60 cycloalkenyl, substituted or unsubstituted C 3-C60 heterocycloalkyl, substituted or unsubstituted C 3-C60 heterocycloalkenyl, substituted or unsubstituted C 6-C60 aryl, Substituted or unsubstituted C 7-C60 aralkyl, substituted or unsubstituted C 2-C60 heteroaryl, substituted or unsubstituted C 3-C60 heteroaralkyl, substituted or unsubstituted C 6-C60 aryloxy, A substituted or unsubstituted C 6-C60 arylthio group, a substituted or unsubstituted C 8-C60 fused polycyclic group, or a substituted or unsubstituted silyl group. The plurality of n2 are each an integer selected from 0 to 2 and are the same or different from each other, and the plurality of n3 are each an integer selected from 0 to 3 and are the same or different from each other. When n2 and n3 are integers of 1 or greater, two or more adjacent groups of R 5 to R 10 are optionally combined with each other to form a substituted or unsubstituted saturated or unsaturated ring. When any two, any three, or all four k are 1, two or more groups of any two, any three, or all four corresponding in R 1 to R 4 combine with each other to form at least one substituted or unsubstituted saturated or unsaturated ring. L 1 and L 2 are each independently substituted or unsubstituted C 6-C60 arylene, substituted or unsubstituted C 4-C60 heteroarylene, substituted or unsubstituted C 6-C60 fused arylene, or substituted or unsubstituted C 4-C60 fused heteroarylene. The aromatic ring groups including Y 1 to Y 4 directly bonded to L 1 and L 2 and the substituted or unsubstituted 1, 10-phenanthroline groups directly bonded to L 1 or L 2 each satisfy a meta-relationship or a para-relationship independently of each other. In some aspects, R 1 and R 2 may combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, R 2 and R 3 may combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, R 3 and R 4 may combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or R 1 and R 2 may combine with each other and R 3 and R 4 may combine with each other to form a substituted or unsubstitut