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KR-20260065641-A - COMPOSITION FOR FORMING EMITTING LAYER, LIGHT EMITTING ELEMENT AND ELECTRONIC DEVICE

KR20260065641AKR 20260065641 AKR20260065641 AKR 20260065641AKR-20260065641-A

Abstract

A composition for forming a light-emitting layer is provided, comprising a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2. A light-emitting element is provided, comprising a first electrode, a second electrode, and a light-emitting layer disposed between the first electrode and the second electrode and comprising the composition for forming a light-emitting layer. Additionally, an electronic device comprising the light-emitting element is provided.

Inventors

  • 김효정

Assignees

  • 삼성디스플레이 주식회사

Dates

Publication Date
20260511
Application Date
20241031

Claims (16)

  1. A composition for forming a light-emitting layer comprising a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula 2: [Chemical Formula 1] [Chemical Formula 2] Among the above chemical formulas 1 and 2, X 21 to X 23 are each independently C(R 1b ) or N, and R1b is hydrogen, deuterium, halogen, hydroxyl group, cyano group, substituted or unsubstituted C1 - C60 alkyl group, substituted or unsubstituted C2 - C60 alkenyl group, substituted or unsubstituted C2 - C60 alkynyl group, substituted or unsubstituted C1 - C60 alkoxy group, substituted or unsubstituted C3 - C60 cycloalkyl group, substituted or unsubstituted C5 - C60 cycloalkenyl group, substituted or unsubstituted C3 - C60 heterocycloalkyl group, substituted or unsubstituted C3 - C60 heterocycloalkenyl group, substituted or unsubstituted C6 - C60 aryl group, substituted or unsubstituted C2 - C60 heteroaryl group, substituted or unsubstituted C6 - C60 aryloxy group, substituted or unsubstituted C8 -C 60 Condensed polycyclic group, -Si( Q1 )( Q2 )( Q3 ), -N( Q1 )( Q2 ), -B( Q1 )(Q2), -C(=O)( Q1 ), -S(=O) 2 ( Q1 ) or -P(=O)( Q1 )( Q2 ), and R 11 to R 14 and R 21 to R 23 are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, substituted or unsubstituted C1 - C60 alkyl group, substituted or unsubstituted C2 - C60 alkenyl group, substituted or unsubstituted C2 - C60 alkynyl group, substituted or unsubstituted C1 - C60 alkoxy group, substituted or unsubstituted C3 - C60 cycloalkyl group, substituted or unsubstituted C5 - C60 cycloalkenyl group, substituted or unsubstituted C3 - C60 heterocycloalkyl group, substituted or unsubstituted C3 - C60 heterocycloalkenyl group, substituted or unsubstituted C6 - C60 aryl group, substituted or unsubstituted C2 - C60 heteroaryl group, substituted or unsubstituted C6 - C60 An aryloxy group, -Se( Q1 ), -Si( Q1 )( Q2 )( Q3 ), -N( Q1 )( Q2 ), -B( Q1 )( Q2 ), -C(=O)( Q1 ), -S(=O) 2 ( Q1 ) or -P(=O)( Q1 )( Q2 ), or at least two adjacent groups among R11 to R14 and R21 to R23 are bonded to each other to form a substituted or unsubstituted C3 - C60 cycloalkyl ring, a substituted or unsubstituted C5 - C60 cycloalkenyl ring, a substituted or unsubstituted C3 - C60 heterocycloalkyl ring, a substituted or unsubstituted C3 - C60 heterocycloalkenyl ring, a substituted or unsubstituted C3 - C60 aryl ring, or a substituted or unsubstituted C2 -C Forms a 60- heteroaryl ring, Q1 to Q3 are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, substituted or unsubstituted C1 - C60 alkyl group, substituted or unsubstituted C2- C60 alkenyl group, substituted or unsubstituted C2 -C60 alkynyl group, substituted or unsubstituted C1 - C60 alkoxy group, substituted or unsubstituted C3 - C60 cycloalkyl group, substituted or unsubstituted C5- C60 cycloalkenyl group, substituted or unsubstituted C3 - C60 heterocycloalkyl group, substituted or unsubstituted C3 - C60 heterocycloalkenyl group, substituted or unsubstituted C6 - C60 aryl group, substituted or unsubstituted C2- C60 heteroaryl group, substituted or unsubstituted C6 - C60 aryloxy group, substituted or unsubstituted C It is a 6 - C60 arylthio group or a substituted or unsubstituted C8 - C60 condensed polycyclic group, and a 11 , a 21 , and a 22 are each independently integers from 0 to 5, and a 12 to a 14 are each independently integers from 0 to 4, and If a 11 to a 14 , a 21 and a 22 are each 2 or more, multiple R 11 to R 14 , R 21 and R 22 are each independently identical or different from each other.
  2. A composition for forming a light-emitting layer according to claim 1, wherein R11 to R14 and R21 to R23 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 - C60 alkyl group, a substituted or unsubstituted C2 - C60 heteroaryl group, -Se( Q1 ) or -Si( Q1 )( Q2 )( Q3 ), or two or more adjacent of R11 to R14 and R21 to R23 are bonded to each other to form a substituted or unsubstituted C2 - C60 heteroaryl ring.
  3. A composition for forming a light-emitting layer according to claim 1, wherein Q1 to Q3 are each independently a substituted or unsubstituted C6 - C60 aryl group or a substituted or unsubstituted C2 - C60 heteroaryl group.
  4. A composition for forming a light-emitting layer according to claim 1, wherein X 21 to X 23 are N.
  5. A composition for forming a light-emitting layer according to claim 1, wherein R 23 is represented by any one of the following chemical formulas 2A-1 to 2A-6: In chemical formulas 2A-1 to 2A-6, * indicates a bonding point.
  6. A composition for forming a light-emitting layer according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-8: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] Among chemical formulas 1-1 to 1-8, R 31 to R 36 , R 41 to R 46 , R 51 to R 56 , R 61 to R 67 , R 71 to R 77 , R 81 to R 88 , R 91 to R 98 , and R 101 to R 110 are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, -Se(Q 1 ), or -Si(Q 1 )(Q 2 )(Q 3 ), or R 31 to R 36 , R 41 to R 46 , R 51 to R 56 , R 61 to R 67 , R 71 to R 77 , R 81 to R 88 , R 91 to R 98 and R Two or more of 101 to R 110 bond together to form a substituted or unsubstituted C 2 -C 60 heteroaryl ring, and a 31 to a 36 , a 41 to a 46 , a 51 to a 56 , a 61 to a 67 , a 71 to a 77 , a 81 , a 83 , a 84 , a 86 , a 93 , a 96 to a 98 , a 102 , a 105 , a 106 , a 108 , and a 110 are each independently integers from 0 to 4, a 82 , a 95 , a 103 , and a 104 are each independently integers from 0 to 3, a 85 , a 94 , and a 107 are each independently integers from 0 to 2, a 87 , a 91 , a 92 , a 101 , and a 109 are each independently integers from 0 to 5, and a 31 to a 36 , a 41 to a 46 , In cases where a 51 to a 56 , a 61 to a 67 , a 71 to a 77 , a 81 to a 88 , a 91 to a 98 , and a 101 to a 110 are each two or more, multiple R 31 to R 36 , R 41 to R 46 , R 51 to R 56 , R 61 to R 67 , R 71 to R 77 , R 81 to R 88 , R 91 to R 98 , and R 101 to R 110 are each independently identical or different from one another.
  7. A composition for forming a light-emitting layer according to claim 1, wherein R 11 to R 14 are each independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted indolecarbazole group, or -Se(Q 1 ) or two or more adjacent R 11 to R 14 are combined with each other to form a substituted or unsubstituted carbazole group.
  8. A composition for forming a light-emitting layer according to claim 1, wherein R 21 to R 23 are each independently hydrogen, deuterium, a substituted or unsubstituted methyl group, -Si(Q 1 )(Q 2 )(Q 3 ) or a substituted or unsubstituted carbazole group, or two or more adjacent R 21 to R 23 are combined with each other to form a substituted or unsubstituted carbazole group.
  9. A composition for forming a light-emitting layer according to claim 1, wherein the chemical formula 2 is represented by any one of the following chemical formulas 2-1 to 2-3: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] Among chemical formulas 2-1 to 2-3, X 61 to X 63 , X 71 to X 73 , and X 81 to X 83 are each independently C(R 1b ) or N, and R1b is hydrogen, deuterium, halogen, hydroxyl group, cyano group, substituted or unsubstituted C1 - C60 alkyl group, substituted or unsubstituted C2 - C60 alkenyl group, substituted or unsubstituted C2 - C60 alkynyl group, substituted or unsubstituted C1 - C60 alkoxy group, substituted or unsubstituted C3 - C60 cycloalkyl group, substituted or unsubstituted C5 - C60 cycloalkenyl group, substituted or unsubstituted C3 - C60 heterocycloalkyl group, substituted or unsubstituted C3 - C60 heterocycloalkenyl group, substituted or unsubstituted C6 - C60 aryl group, substituted or unsubstituted C2 - C60 heteroaryl group, substituted or unsubstituted C6 - C60 aryloxy group, substituted or unsubstituted C8 -C 60 Condensed polycyclic group, -Si( Q1 )( Q2 )( Q3 ), -N( Q1 )( Q2 ), -B( Q1 )(Q2), -C(=O)( Q1 ), -S(=O) 2 ( Q1 ) or -P(=O)( Q1 )( Q2 ), and P 61 and P 81 are each independently C, Si, or Ge, and R61 to R67 , R71 to R75 , and R81 to R88 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 - C60 alkyl group, a substituted or unsubstituted C2 - C60 heteroaryl group, or -Si( Q1 )( Q2 )( Q3 ), or two or more adjacent of R61 to R67 , R71 to R75 , and R81 to R88 are bonded to each other to form a substituted or unsubstituted C2-C60 heteroaryl ring, and Q1 to Q3 are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, substituted or unsubstituted C1 - C60 alkyl group, substituted or unsubstituted C2- C60 alkenyl group, substituted or unsubstituted C2 -C60 alkynyl group, substituted or unsubstituted C1 - C60 alkoxy group, substituted or unsubstituted C3 - C60 cycloalkyl group, substituted or unsubstituted C5- C60 cycloalkenyl group, substituted or unsubstituted C3 - C60 heterocycloalkyl group, substituted or unsubstituted C3 - C60 heterocycloalkenyl group, substituted or unsubstituted C6 - C60 aryl group, substituted or unsubstituted C2- C60 heteroaryl group, substituted or unsubstituted C6 - C60 aryloxy group, substituted or unsubstituted C It is a 6 - C60 arylthio group or a substituted or unsubstituted C8 - C60 condensed polycyclic group, and a 61 , a 65 to a 67 , a 72 , a 81 , and a 85 to a 88 are each independently integers from 0 to 5, and a 62 to a 64 , a 71 , a 73 , a 82 , and a 84 are each independently integers from 0 to 4, and a 83 is an integer from 0 to 3, and If a 61 to a 67 , a 71 to a 73 , and a 81 to a 88 are each two or more, then multiple R 61 to R 67 , R 71 to R 75 , and R 81 to R 88 are each independently identical or different from one another.
  10. A composition for forming a light-emitting layer according to claim 9, wherein at least one of R 71 , R 73 , R 74 and R 75 is represented by any one of the following chemical formulas 2-2A-1 to 2-2A-4: In chemical formulas 2-2A-1 to 2-2A-4, * indicates a bonding point.
  11. In claim 1, A composition for forming a light-emitting layer, wherein the compound represented by Chemical Formula 1 above is any one of the following compounds: .
  12. A composition for forming a light-emitting layer according to claim 1, wherein the compound represented by Chemical Formula 2 is any one of the following compounds: .
  13. First electrode; A light-emitting device comprising: a second electrode; and a light-emitting layer disposed between the first electrode and the second electrode, and comprising a composition for forming a light-emitting layer according to claim 1.
  14. An electronic device comprising the light-emitting element of claim 13.
  15. Claim 14 further comprises a thin-film transistor, The above thin-film transistor includes a source electrode and a drain electrode, and An electronic device in which the first electrode of the light-emitting element is electrically connected to at least one of the source electrode and the drain electrode of the thin-film transistor.
  16. An electronic device according to claim 14, further comprising a functional layer disposed on the light-emitting element and comprising a sensor layer, a polarizing layer, a color conversion layer, a color filter layer, a window film, or a combination of two or more of these.

Description

Composition for Forming Emitting Layer, Light Emitting Element and Electronic Device The embodiments of the present application relate to a composition for forming a light-emitting layer, a light-emitting element, and an electronic device. Organic light-emitting diodes (OLEDs) are receiving significant attention as self-emissive display devices due to their advantages, including a wide viewing angle, excellent color contrast, and fast response time. OLEDs can be classified into inorganic OLEDs, which use inorganic compounds in the emissive layer, and organic OLEDs, which use organic compounds. Much research is being conducted on OLEDs because they offer superior characteristics in brightness, driving voltage, and response speed compared to inorganic OLEDs, as well as the potential for multi-colorization. An organic light-emitting device generally has a stacked structure of an anode, a light-emitting layer, and a cathode, and by additionally stacking a hole injection layer, a hole transport layer, and an electron injection layer between the anode and the light-emitting layer or between the light-emitting layer and the cathode, it has a structure of an anode, a hole transport layer, a light-emitting layer, and a cathode, or an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode. In the context of organic light-emitting diodes, applications for full-color displays or lighting are actively underway, and to this end, there is an increasing need for blue light-emitting materials with high brightness, high efficiency, and high color purity. FIGS. 1 to 6 are schematic cross-sectional views showing light-emitting elements according to exemplary embodiments. FIG. 7 is a schematic cross-sectional view showing a display device according to exemplary embodiments. FIG. 8 is a schematic cross-sectional view showing a display device according to exemplary embodiments. FIG. 9 is a schematic cross-sectional view showing a stacked form of a light-emitting structure in a display device according to exemplary embodiments. FIG. 10 is a schematic cross-sectional view showing a display device according to exemplary embodiments. FIG. 11 is a schematic cross-sectional view showing a display device according to exemplary embodiments. FIG. 12 is a schematic diagram showing an electronic device according to exemplary embodiments. FIG. 13 is a schematic diagram showing an electronic device according to exemplary embodiments. Definition of Terms In this specification, "number of carbon atoms a to b", "Ca - Cb", and "Ca to Cb" may refer to substituents comprising a to b carbon atoms. In this specification, "substituted or unsubstituted" refers, for example, a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, an ester group, a boron, a phosphine oxide group, a phosphine sulfide group, an alkyl group (e.g., C1-C60 , C1 - C10 alkyl group), an alkenyl group (e.g., C2 - C60 , C2 - C10 alkenyl group), an alkynyl group (e.g., C2 -C60, C2- C10 alkynyl group), an alkoxy group (e.g., C1 - C60 , C1 - C10 alkoxy group), a hydrocarbon ring group, an aryl group (e.g., C6 - C60 aryl group), a heterocyclic group (e.g., C1 It may refer to one that is substituted or unsubstituted with one or more substituents selected from the group consisting of (-C 60 heterocyclic groups). For example, "substituted alkyl group" may refer to one in which at least one of the hydrogen atoms of the alkyl group is substituted with the substituent described above, thereby further bonding a substituent to a carbon atom of the alkyl group. The above substituent may include a combination selected from the groups described above. For example, at least one of the hydrogen atoms, such as alkyl groups and aryl groups included as substituents, may be substituted with a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, an ester group, a boron, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, a hydrocarbon ring group, an aryl group, or a heterocyclic group. Among the above substituents, multivalent substituents such as amino groups, phosphine sulfide groups, phosphine oxide groups, sulfinyl groups, sulfonyl groups, sulfanyl groups, oxy groups, carbonyl groups, and ester groups may be substituted with C1 - C10 alkyl groups, C1 - C10 alkenyl groups, C1 - C10 alkynyl groups, or aryl groups having 6 to 10 carbon atoms. In the term "substituted or unsubstituted Y group having carbon a to b" as used in this specification, carbon a to b refers to the number of carbons in the unsubstituted Y group and does not include the number of carbons in the substituent. An alkyl group refers to a monovalent hydrocarbon group from which one hydrogen atom has bee