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KR-20260065645-A - Compound, Light emitting device comprising same and electronic apparatus comprising same

KR20260065645AKR 20260065645 AKR20260065645 AKR 20260065645AKR-20260065645-A

Abstract

Compounds represented by Chemical Formula 1 and A light-emitting device is disclosed comprising a first electrode, a second electrode opposite to the first electrode, and an intermediate layer disposed between the first electrode and the second electrode, the intermediate layer comprising a light-emitting layer, wherein the intermediate layer comprises a compound represented by Chemical Formula 1.

Inventors

  • 김경헌
  • 이준영
  • 김회림
  • 유하영

Assignees

  • 삼성디스플레이 주식회사

Dates

Publication Date
20260511
Application Date
20241031

Claims (20)

  1. Compound represented by the following chemical formula 1: <Chemical Formula 1> Among the above chemical formula 1, A1 and A3 independently represent hydrogen, deuterium, or cyano groups, or fused with C5 carbocyclic groups, and A2 indicates that C4 - C6 carbocyclic groups are fused, and R1 to R7 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, a C1 - C60 alkyl group substituted or unsubstituted with at least one R10a , a C3 - C10 cycloalkyl group substituted or unsubstituted with at least one R10a , a C2 - C60 alkenyl group substituted or unsubstituted with at least one R10a , a C2-C60 alkynyl group substituted or unsubstituted with at least one R10a , a C1 - C60 alkoxy group substituted or unsubstituted with at least one R10a, a C1 - C60 alkylthio group substituted or unsubstituted with at least one R10a , a C6 - C60 aryl group substituted or unsubstituted with at least one R10a , and at least one R10a substituted or unsubstituted C6 - C60 aryloxy group, C6-C60 aryltio group substituted or unsubstituted with at least one R10a , C1 - C60 heteroaryl group substituted or unsubstituted with at least one R10a , C8 - C60 non-aromatic condensed polycyclic group substituted or unsubstituted with at least one R10a , C1 - C60 non-aromatic heterocondensed polycyclic group substituted or unsubstituted with at least one R10a , -C( Q1 )( Q2 )( Q3 ), -Si( Q1 )(Q2)( Q3 ), -N( Q1 )( Q2 ), -B(Q1 ) ( Q2 ), -C(=O)( Q1 ) , -S(=O) 2 (Q1 ) , or -P(=O)( Q1 )(Q 2 ) and, a1, a4, and a6 are independent integers from 0 to 3, and if a1 is 2 or greater, each R1 may be the same or different, if a4 is 2 or greater, each R4 may be the same or different, and if a6 is 2 or greater, each R6 may be the same or different, and The above R 10a is, Hydrogen, -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3 - C60 carbocyclic group, C1 - C60 heterocyclic group, C6 - C60 aryloxy group, C6 - C60 arylthio group, -Si( Q11 )( Q12 )( Q13 ), -N( Q11 )( Q12 ), -B( Q11 )(Q12), -C( = O)( Q11 ), -S(=O) 2 ( Q11 ), -P(=O)( Q11 )( Q12 ), or any combination thereof, C1 - C60 alkyl group, C2 - C60 alkenyl group, C2 - C60 alkynyl group, or C1 -C 60 alkoxygen; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1 - C60 alkyl group, C2 - C60 alkenyl group, C2 - C60 alkynyl group, C1 - C60 alkoxy group, C3 - C60 carbocyclic group, C1 - C60 heterocyclic group, C6 - C60 aryloxy group, C6 - C60 arylthio group, -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 Substituted or unsubstituted, C3 - C60 carbocyclic group, C1 - C60 heterocyclic group, C6 - C60 aryloxy group, or C6 - C60 aryltio group; or -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ), or -P(=O)(Q 31 )(Q 32 ); And, The above Q1 to Q3 , Q11 to Q13, Q21 to Q23 and Q31 to Q33 are independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C1 - C60 alkyl group; C2 - C60 alkenyl group; C2 - C60 alkynyl group; C1 - C60 alkoxy group; or A C3 - C60 carbocyclic group, C1 - C60 heterocyclic group, C7 - C60 arylalkyl group, or C2-C60 heteroarylalkyl group substituted or unsubstituted with deuterium, -F, cyano group, C1 - C60 alkyl group, C1 - C60 alkoxy group, phenyl group , biphenyl group, or any combination thereof, and Chemical formula 1 contains a cyano group.
  2. In paragraph 1, The above A1 and A3 are independently hydrogen, deuterium, or cyano groups, or A compound indicating that cyclopentene is fused.
  3. In paragraph 1, The above A 2 is a compound in which cyclobutane or bicycle[2,2,0]hex-1(4)-ene is fused.
  4. In paragraph 1, A compound having the above chemical formula 1 as a symmetrical form.
  5. In paragraph 1, Compound represented by the above Chemical Formula 1 as the following Chemical Formula 1-1: <Chemical Formula 1-1> In the above chemical formula 1-1, The definitions for R1 to R5 and R7 , a1 and a4 are the same as in Chemical Formula 1, and Chemical formula 1-1 contains a cyano group.
  6. In paragraph 1, Compounds represented by the above Chemical Formula 1 as the following Chemical Formula 1-2: <Chemical Formula 1-2> In the above chemical formula 1-2, The definitions for R1 to R5 and R7 , a1 and a4 are the same as in Chemical Formula 1, and Chemical formula 1-2 contains a cyano group.
  7. In paragraph 1, Compounds represented by the above Chemical Formula 1 as the following Chemical Formula 1-3: <Chemical Formula 1-3> In the above chemical formula 1-3, R 2-1 to R 2-4 are independently hydrogen, deuterium, or cyano groups, and The definitions for R2 , R3 , R5 , and R7 are the same as in Chemical Formula 1, and Chemical formula 1-3 contains a cyano group.
  8. In paragraph 1, Compounds represented by the above Chemical Formula 1 as the following Chemical Formula 1-4: <Chemical Formula 1-4> In the above chemical formula 1-4, The definitions for R1 to R5 and R7 , a1 and a4 are the same as in Chemical Formula 1, and Chemical formula 1-4 contains a cyano group.
  9. In paragraph 1, Compounds represented by the above Chemical Formula 1 as the following Chemical Formula 1-5: <Chemical Formula 1-5> In the above chemical formula 1-5, The definitions for R1 to R5 and R7 , a1 and a4 are the same as in Chemical Formula 1, and Chemical formula 1-5 contains a cyano group.
  10. In paragraph 1, A compound represented by the above chemical formula 1 that comprises any one of the following compounds: .
  11. First electrode; A second electrode facing the first electrode; and A light-emitting element comprising an intermediate layer including a light-emitting layer disposed between the first electrode and the second electrode, wherein A light-emitting device in which the above intermediate layer comprises a compound represented by the chemical formula 1 of claim 1.
  12. In Paragraph 11, The first electrode is an anode, and The above second electrode is a cathode, and The above intermediate layer is disposed between the first electrode and the light-emitting layer and comprises a hole injection layer; a hole transport region including a hole transport layer, an electron blocking layer, a light-emitting auxiliary layer, or any combination thereof, and/or A light-emitting device comprising a second electrode disposed between the light-emitting layer and further comprising an electron transport region including a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
  13. In Paragraph 12, A light-emitting device in which the hole transport region comprises a compound represented by Chemical Formula 1.
  14. In Paragraph 11, The above-mentioned light-emitting layer includes a first host, a second host, and a dopant, and The above dopant is a compound comprising a ligand containing a metal and an imidazole moiety, Light-emitting element.
  15. In Paragraph 14, The above first host is a hole-transporting host, and The above second host is a light-emitting element that is an electron transportable host.
  16. In Paragraph 11, The light-emitting element comprises a red light-emitting layer, a blue light-emitting layer, and a green light-emitting layer.
  17. In Paragraph 11, The above-mentioned light-emitting layer includes m light-emitting layers, and The above intermediate layer further includes m-1 charge generation layers interposed between two adjacent light-emitting layers among the m light-emitting layers, and The above m is an integer greater than or equal to 2, and The charge generating layer comprises a compound represented by Chemical Formula 1, Light-emitting element.
  18. An electronic device including the light-emitting element of paragraph 11.
  19. An electronic device including the light-emitting element of paragraph 11.
  20. In Paragraph 19, An electronic device that is one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a light for indoor or outdoor lighting and/or signaling, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal information terminal (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a light therapy device, and a signboard.

Description

Compound, light-emitting device comprising the same, and electronic apparatus comprising the same The invention relates to a compound, a light-emitting element containing the same, and an electronic device containing the same. Among light-emitting devices, self-emissive devices not only have a wide viewing angle and excellent contrast, but also fast response time and excellent characteristics in brightness, driving voltage, and response speed. The light-emitting device may have a structure in which a first electrode is disposed on a substrate, and a hole transport region, a light-emitting layer, an electron transport region, and a second electrode are sequentially disposed on the first electrode. Holes injected from the first electrode move to the light-emitting layer via the hole transport region, and electrons injected from the second electrode move to the light-emitting layer via the electron transport region. Carriers such as holes and electrons recombine in the light-emitting layer region to generate excitons. Light is generated as the excitons change from an excited state to a ground state. Figures 1 and 2 are schematic diagrams showing the structure of a light-emitting element according to one embodiment, respectively. FIG. 3 is a cross-sectional view of an electronic device according to one embodiment of the present invention. FIG. 4 is a cross-sectional view of an electronic device according to another embodiment of the present invention. FIG. 5 is a perspective view schematically illustrating an electronic device including a light-emitting element according to one embodiment. FIG. 6 is a schematic diagram illustrating the exterior of a vehicle as an electronic device including a light-emitting element according to one embodiment of the present invention. FIGS. 7a to 7c are schematic drawings illustrating the interior of a vehicle according to various embodiments of the present invention. The efficiency, driving, and lifespan characteristics of light-emitting devices require continuous improvement, and to this end, hole injection layer materials used in the hole transport region are being steadily developed. The performance of light-emitting devices and the like has been improved by newly developing p-dopant materials for use in the hole injection layer. A compound according to one aspect is represented by the following chemical formula 1: <Chemical Formula 1> Among the above chemical formula 1, A1 and A3 independently represent hydrogen, deuterium, or cyano groups, or fused with C5 carbocyclic groups, and A2 indicates that C4 - C6 carbocyclic groups are fused, and R1 to R7 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, a C1 - C60 alkyl group substituted or unsubstituted with at least one R10a , a C3 - C10 cycloalkyl group substituted or unsubstituted with at least one R10a , a C2 - C60 alkenyl group substituted or unsubstituted with at least one R10a , a C2-C60 alkynyl group substituted or unsubstituted with at least one R10a , a C1 - C60 alkoxy group substituted or unsubstituted with at least one R10a, a C1 - C60 alkylthio group substituted or unsubstituted with at least one R10a , a C6 - C60 aryl group substituted or unsubstituted with at least one R10a , and at least one R10a substituted or unsubstituted C6 - C60 aryloxy group, C6-C60 aryltio group substituted or unsubstituted with at least one R10a , C1 - C60 heteroaryl group substituted or unsubstituted with at least one R10a , C8 - C60 non-aromatic condensed polycyclic group substituted or unsubstituted with at least one R10a , C1 - C60 non-aromatic heterocondensed polycyclic group substituted or unsubstituted with at least one R10a , -C( Q1 )( Q2 )( Q3 ), -Si( Q1 )(Q2)( Q3 ), -N( Q1 )( Q2 ), -B(Q1 ) ( Q2 ), -C(=O)( Q1 ) , -S(=O) 2 (Q1 ) , or -P(=O)( Q1 )(Q 2 ) and, a1, a4, and a6 are independent integers from 0 to 3, and if a1 is 2 or greater, each R1 may be the same or different, if a4 is 2 or greater, each R4 may be the same or different, and if a6 is 2 or greater, each R6 may be the same or different, and The above R 10a is, Hydrogen, -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3 - C60 carbocyclic group, C1 - C60 heterocyclic group, C6 - C60 aryloxy group, C6 - C60 arylthio group, -Si( Q11 )( Q12 )( Q13 ), -N( Q11 )( Q12 ), -B( Q11 )(Q12), -C( = O)( Q11 ), -S(=O) 2 ( Q11 ), -P(=O)( Q11 )( Q12 ), or any combination thereof, C1 - C60 alkyl group, C2 - C60 alkenyl group, C2 - C60 alkynyl group, or C1 -C 60 alkoxygen; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1 - C60 alkyl group, C2 - C60 alkenyl group, C2 - C60 alkynyl group, C1 - C60 alkoxy group, C3 - C60 carbocyclic group, C1 - C60 heterocyclic group, C6 - C60 aryloxy group, C6 - C60 arylthio group, -Si( Q21 )( Q22 )( Q23 ), -N( Q21 )( Q22 ), -B( Q21)(Q22 ) , -C(=O)( Q21 ), -S(=O) 2 ( Q21 ), -P(=O)( Q21 )( Q22 ), or a