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CN-121990947-A - Light-emitting device including condensed-ring compound, electronic device including light-emitting device, and condensed-ring compound

CN121990947ACN 121990947 ACN121990947 ACN 121990947ACN-121990947-A

Abstract

The present invention relates to a light-emitting device including a condensed-cyclic compound, an electronic device including a light-emitting device, and a condensed-cyclic compound. The condensed-cyclic compound is represented by formula 1 described in detail in the specification. 1 (1)

Inventors

  • JIN JINGXIAN
  • LI JUNRONG
  • JIN HUILIN

Assignees

  • 三星显示有限公司

Dates

Publication Date
20260508
Application Date
20251107
Priority Date
20241107

Claims (11)

  1. 1. A light emitting device, comprising: A first electrode; A second electrode opposite to the first electrode, and An interlayer between the first electrode and the second electrode and comprising an emissive layer, Wherein the interlayer comprises a fused ring compound represented by formula 1: 1 (1) A kind of electronic device Wherein, in the formula 1, R 1 to R 8 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 60 alkyl which is unsubstituted or substituted by at least one R 10a , C 2 -C 60 alkenyl unsubstituted or substituted by at least one R 10a , C 2 -C 60 alkynyl unsubstituted or substituted by at least one R 10a , C 1 -C 60 alkoxy which is unsubstituted or substituted by at least one R 10a , C 1 -C 60 alkylthio which is unsubstituted or substituted by at least one R 10a , C 3 -C 60 carbocyclyl unsubstituted or substituted by at least one R 10a , C 1 -C 60 heterocyclyl unsubstituted or substituted by at least one R 10a , C 6 -C 60 aryloxy which is unsubstituted or substituted by at least one R 10a , C 6 -C 60 arylthio which is unsubstituted or substituted by at least one R 10a , C 7 -C 60 aralkyl 、-Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or-P (=o) (Q 1 )(Q 2 ) unsubstituted or substituted by at least one R 10a , At least one selected from R 1 to R 8 includes an electron withdrawing group, Indicating a single bond or a double bond, R 10a is: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, amidino, hydrazino, hydrazone or nitro; c 1 -C 60 alkyl, C 2 -C 60 alkenyl, C 2 -C 60 alkynyl, C 1 -C 60 alkoxy, or C 1 -C 60 alkylthio, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 carbocyclyl, C 1 -C 60 heterocyclyl, C 6 -C 60 aryloxy, C 6 -C 60 arylthio, C 7 -C 60 aralkyl, C 2 -C 60 heteroarylalkyl 、-Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ), or any combination thereof; C 3 -C 60 carbocyclyl, C 1 -C 60 heterocyclyl, C 6 -C 60 aryloxy, C 6 -C 60 arylthio, C 7 -C 60 aralkyl or C 2 -C 60 heteroaralkyl, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 alkyl, C 2 -C 60 alkenyl, C 2 -C 60 alkynyl, C 1 -C 60 alkoxy, C 1 -C 60 alkylthio, C 3 -C 60 carbocyclyl, C 1 -C 60 heterocyclyl, C 6 -C 60 aryloxy, C 6 -C 60 arylthio, C 7 -C 60 aralkyl, C 2 -C 60 heteroaralkyl 、-Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof, or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) Or-P (=O) (Q 31 )(Q 32 ), and Q 1 to Q 3 、Q 11 to Q 13 、Q 21 to Q 23 and Q 31 to Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, or C 1 -C 60 alkyl, C 2 -C 60 alkenyl, C 2 -C 60 alkynyl, C 1 -C 60 alkoxy, C 1 -C 60 alkylthio, C 3 -C 60 carbocyclyl, C 1 -C 60 heterocyclyl, C 6 -C 60 aryloxy, C 6 -C 60 arylthio, C 7 -C 60 aralkyl or C 2 -C 60 heteroaralkyl each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 alkyl, C 1 -C 60 alkoxy, phenyl, biphenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof.
  2. 2. The light-emitting device of claim 1, wherein The first electrode is an anode and the second electrode is an anode, The second electrode is a cathode electrode and, The interlayer further comprises a hole transport region between the first electrode and the emissive layer and an electron transport region between the emissive layer and the second electrode, The hole transport region comprises a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof, and The electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
  3. 3. The light-emitting device according to claim 2, wherein The hole transport region includes the hole injection layer, and The hole injection layer includes the condensed cyclic compound represented by formula 1.
  4. 4. A light emitting device according to claim 3 wherein The hole injection layer includes a hole transport material, and The hole transport material includes a compound represented by formula 201, a compound represented by formula 202, or any combination thereof: 201, a method for manufacturing a semiconductor device 202, Respectively A kind of electronic device Wherein, in the formulas 201 and 202, L 201 to L 204 are each independently C 3 -C 60 carbocyclyl which is unsubstituted or substituted by at least one R 10a or C 1 -C 60 heterocyclyl which is unsubstituted or substituted by at least one R 10a , L 205 is-O ', -S', -N (Q 201 ) -, C 1 -C 20 alkylene unsubstituted or substituted with at least one R 10a , C 2 -C 20 alkenylene unsubstituted or substituted with at least one R 10a C 3 -C 60 carbocyclyl which is unsubstituted or substituted by at least one R 10a or C 1 -C 60 heterocyclyl which is unsubstituted or substituted by at least one R 10a , Xa1 to xa4 are each independently an integer selected from 0 to 5, Xa5 is an integer selected from 1 to 10, R 201 to R 204 and Q 201 are each independently C 3 -C 60 carbocyclyl which is unsubstituted or substituted by at least one R 10a or C 1 -C 60 heterocyclyl which is unsubstituted or substituted by at least one R 10a , R 201 and R 202 are optionally linked to one another via a single bond, C 1 -C 5 alkylene which is unsubstituted or substituted by at least one R 10a or C 2 -C 5 alkenylene which is unsubstituted or substituted by at least one R 10a to form a C 8 -C 60 polycyclic group which is unsubstituted or substituted by at least one R 10a , R 203 and R 204 are optionally linked to one another via a single bond, C 1 -C 5 alkylene which is unsubstituted or substituted by at least one R 10a or C 2 -C 5 alkenylene which is unsubstituted or substituted by at least one R 10a to form a C 8 -C 60 polycyclic group which is unsubstituted or substituted by at least one R 10a , Na1 is an integer selected from 1 to 4, and R 10a is the same as described in formula 1.
  5. 5. An electronic device comprising the light-emitting device according to any one of claims 1 to 4.
  6. 6. The electronic device of claim 5, wherein: The electronic device is at least 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 telephone, a cellular phone, a tablet personal computer, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a micro display, a three-dimensional display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays spliced together, a theatre screen, a stadium screen, a phototherapy device, and a sign.
  7. 7. A fused ring compound represented by formula 1: 1 (1) , Wherein, in the formula 1, R 1 to R 8 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 60 alkyl which is unsubstituted or substituted by at least one R 10a , C 2 -C 60 alkenyl unsubstituted or substituted by at least one R 10a , C 2 -C 60 alkynyl unsubstituted or substituted by at least one R 10a , C 1 -C 60 alkoxy which is unsubstituted or substituted by at least one R 10a , C 1 -C 60 alkylthio which is unsubstituted or substituted by at least one R 10a , C 3 -C 60 carbocyclyl unsubstituted or substituted by at least one R 10a , C 1 -C 60 heterocyclyl unsubstituted or substituted by at least one R 10a , C 6 -C 60 aryloxy which is unsubstituted or substituted by at least one R 10a , C 6 -C 60 arylthio which is unsubstituted or substituted by at least one R 10a , C 7 -C 60 aralkyl 、-Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or-P (=o) (Q 1 )(Q 2 ) unsubstituted or substituted by at least one R 10a , At least one selected from R 1 to R 8 comprises an electron withdrawing group that excludes a C 1 -C 60 alkoxy group that is unsubstituted or substituted with at least one R 10a and a C 1 -C 60 alkylthio group that is unsubstituted or substituted with at least one R 10a , Indicating a single bond or a double bond, R 10a is: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, amidino, hydrazino, hydrazone or nitro; c 1 -C 60 alkyl, C 2 -C 60 alkenyl, C 2 -C 60 alkynyl, C 1 -C 60 alkoxy, or C 1 -C 60 alkylthio, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 carbocyclyl, C 1 -C 60 heterocyclyl, C 6 -C 60 aryloxy, C 6 -C 60 arylthio, C 7 -C 60 aralkyl, C 2 -C 60 heteroarylalkyl 、-Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ), or any combination thereof; C 3 -C 60 carbocyclyl, C 1 -C 60 heterocyclyl, C 6 -C 60 aryloxy, C 6 -C 60 arylthio, C 7 -C 60 aralkyl or C 2 -C 60 heteroaralkyl, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 alkyl, C 2 -C 60 alkenyl, C 2 -C 60 alkynyl, C 1 -C 60 alkoxy, C 1 -C 60 alkylthio, C 3 -C 60 carbocyclyl, C 1 -C 60 heterocyclyl, C 6 -C 60 aryloxy, C 6 -C 60 arylthio, C 7 -C 60 aralkyl, C 2 -C 60 heteroaralkyl 、-Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof, or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) Or-P (=O) (Q 31 )(Q 32 ), and Q 1 to Q 3 、Q 11 to Q 13 、Q 21 to Q 23 and Q 31 to Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, or C 1 -C 60 alkyl, C 2 -C 60 alkenyl, C 2 -C 60 alkynyl, C 1 -C 60 alkoxy, C 1 -C 60 alkylthio, C 3 -C 60 carbocyclyl, C 1 -C 60 heterocyclyl, C 6 -C 60 aryloxy, C 6 -C 60 arylthio, C 7 -C 60 aralkyl or C 2 -C 60 heteroaralkyl each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 alkyl, C 1 -C 60 alkoxy, phenyl, biphenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof.
  8. 8. The fused ring compound according to claim 7, wherein At least one selected from R 1 to R 8 includes a cyano group, and The ratio of the number of cyano groups of the condensed-cyclic compound to the molecular weight of the condensed-cyclic compound is 0.01 or more.
  9. 9. The fused ring compound according to claim 7, wherein At least one selected from R 1 to R 8 is cyano, a group represented by formula 2-1 or a group represented by formula 2-2, 2-1 2-2 A kind of electronic device Wherein, in the formula 2-1 and the formula 2-2, R 11 to R 13 are each independently hydrogen, deuterium, cyano, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 6 -C 20 aryl or C 6 -C 20 heteroaryl, * Indicating the bonding sites with adjacent atoms, At least one of R 11 and R 12 in formula 2-1 includes a cyano group, and At least one selected from R 11 to R 13 in formula 2-2 includes a cyano group.
  10. 10. The fused ring compound according to claim 7, wherein The number of electron withdrawing groups in the fused ring compound is 4 or more.
  11. 11. The fused ring compound according to claim 7, wherein The condensed-cyclic compound is any one selected from the group consisting of compounds 1 to 22: 。

Description

Light-emitting device including condensed-ring compound, electronic device including light-emitting device, and condensed-ring compound Cross Reference to Related Applications The present application claims priority and equity from korean patent application No. 10-2024-0156882 filed at korean intellectual property office on day 11 and 7 of 2024, the entire disclosure of which is incorporated herein by reference. Technical Field One or more embodiments of the present disclosure relate to a light emitting device including a condensed ring compound, an electronic device including the light emitting device, and a condensed ring compound. Background The organic light emitting device is a self-emission device, has a relatively wide viewing angle, high contrast, short response time, and excellent or appropriate characteristics in terms of brightness, driving voltage, and response speed, as compared with other light emitting devices of the related art, and produces a full color image. The organic light emitting device may have a structure in which a first electrode is disposed on a substrate, and then a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially disposed. Holes supplied from the first electrode move toward the emission layer through the hole transport region, while electrons supplied from the second electrode move toward the emission layer through the electron transport region. These carriers (i.e., holes and electrons) recombine in the emissive layer to generate excitons. Light is emitted when the excitons transition and decay from an excited state to a ground state. Disclosure of Invention One or more aspects of embodiments of the present disclosure relate to a light-emitting device including a condensed-cyclic compound, an electronic device including the light-emitting device, and a condensed-cyclic compound. Additional aspects will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the presently disclosed embodiments. According to one or more embodiments of the present disclosure, a light emitting device includes: A first electrode; a second electrode opposite (e.g., facing) the first electrode, and An interlayer located between the first electrode and the second electrode and comprising an emissive layer, wherein The interlayer includes a fused ring compound represented by formula 1: 1 (1) , Wherein, in the formula 1, R 1 to R 8 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1-C60 alkyl which is unsubstituted or substituted by at least one R 10a, C 2-C60 alkenyl unsubstituted or substituted by at least one R 10a, C 2-C60 alkynyl unsubstituted or substituted by at least one R 10a, C 1-C60 alkoxy which is unsubstituted or substituted by at least one R 10a, C 1-C60 alkylthio which is unsubstituted or substituted by at least one R 10a, C 3-C60 carbocyclyl unsubstituted or substituted by at least one R 10a, C 1-C60 heterocyclyl unsubstituted or substituted by at least one R 10a, C 6-C60 aryloxy which is unsubstituted or substituted by at least one R 10a, C 6-C60 arylthio which is unsubstituted or substituted by at least one R 10a, C 7-C60 aralkyl 、-Si(Q1)(Q2)(Q3)、-Ge(Q1)(Q2)(Q3)、-N(Q1)(Q2)、-B(Q1)(Q2)、-C(=O)(Q1)、-S(=O)2(Q1) or-P (=o) (Q 1)(Q2) unsubstituted or substituted by at least one R 10a, At least one selected from R 1 to R 8 may comprise an electron withdrawing group Indicating a single bond or a double bond, R 10a may be: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, amidino, hydrazino, hydrazone or nitro; C 1-C60 alkyl, C 2-C60 alkenyl, C 2-C60 alkynyl, C 1-C60 alkoxy, or C 1-C60 alkylthio, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3-C60 carbocyclyl, C 1-C60 heterocyclyl, C 6-C60 aryloxy, C 6-C60 arylthio, C 7-C60 aralkyl, C 2-C60 heteroarylalkyl 、-Si(Q11)(Q12)(Q13)、-N(Q11)(Q12)、-B(Q11)(Q12)、-C(=O)(Q11)、-S(=O)2(Q11)、-P(=O)(Q11)(Q12), or a combination thereof (e.g., any suitable combination), C 3-C60 carbocyclyl, C 1-C60 heterocyclyl, C 6-C60 aryloxy, C 6-C60 arylthio, C 7-C60 aralkyl or C 2-C60 heteroaralkyl, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1-C60 alkyl, C 2-C60 alkenyl, C 2-C60 alkynyl, C 1-C60 alkoxy, C 1-C60 alkylthio, C 3-C60 carbocyclyl, C 1-C60 heterocyclyl, C 6-C60 aryloxy, C 6-C60 arylthio, C 7-C60 aralkyl, C 2-C60 heteroaralkyl 、-Si(Q21)(Q22)(Q23)、-N(Q21)(Q22)、-B(Q21)(Q22)、-C(=O)(Q21)、-S(=O)2(Q21)、-P(=O)(Q21)(Q22) or any combination thereof, or -Si(Q31)(Q32)(Q33)、-N(Q31)(Q32)、-B(Q31)(Q32)、-P(Q31)(Q32)、-C(=O)(Q31)、-S(=O)2(Q31) Or-P (=O) (Q 31)(Q32), and Q 1 to Q 3、Q11 to Q 13、Q21 to Q 23 and Q 31 to Q 33 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, or C 1-C60 alkyl, C 2-C60 alkenyl, C 2-C60 alkynyl, C 1-C60 alkoxy, C 1-C60 alkylthio, C 3-C60 carbocycly