KR-20260068130-A - ORGANIC MOLECULES FOR OPTOELECTRONIC DEVICES

Abstract

The present invention relates particularly to organic molecules and compositions for application in optoelectronic devices.

Inventors

• 시퍼만 스테판
• 카스파렉 크리스찬
• 슈말츠 마르쿠

Assignees

• 삼성디스플레이 주식회사

Dates

Publication Date

20260513

Application Date

20201216

Priority Date

20191220

Claims (10)

1. A composition comprising the following components: (i) 0.1-10 wt% of an organic molecule having the structure of the following chemical formula I; (ii) 5-99 wt% of one or more host compounds H; (iii) 0.9-94.9 wt% of one or more additional host compounds D having a structure different from that of the organic molecule; and (iv) Optionally, 0 to 30 weight% of at least one additional emitter molecule F having a structure different from the structure of the organic molecule: Chemical Formula I Here R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , and R XI are independently selected from the group consisting of the following: Hydrogen; Deuterium; Halogen; Optionally, C1 - C12 -alkyl in which one or more hydrogen atoms are independently substituted by R5 ; and A C6 - C18 -aryl in which one or more hydrogen atoms are optionally independently substituted by R5 ; R 5 is independently selected from a group consisting of the following: Hydrogen; deuterium; and Optionally, a C1 - C12 -alkyl or C6 - C18 -aryl in which one or more hydrogen atoms are independently substituted by a C1 - C5 -alkyl substituent; One or more of R I , R II , R III , R IV , and R V , and one or more of R VI , R VII , R VIII , R IX , and R X are Optionally, C1 - C12 -alkyl in which one or more hydrogen atoms are independently substituted by R5 ; or A C6 - C18 -aryl in which one or more hydrogen atoms are optionally independently substituted by R5 ; and Optionally, the hydrogen is independently substituted with deuterium or a halogen.
2. In paragraph 1, A composition further comprising 0-94 weight% of solvent.
3. In paragraph 1, The above host compound H has a highest occupied molecular orbital HOMO (H) having an energy E HOMO (H) in the range of -5 to -6.5 eV, and The above additional host compound D has the highest occupied molecular orbital HOMO(D) with E HOMO (D) energy, A composition in which E HOMO (H) > E HOMO (D).
4. In paragraph 1, The above host compound H has a lowest unoccupied molecular orbital LUMO(H) with energy E LUMO (H), and The above additional host compound D has a lowest unoccupied molecular orbital LUMO(D) with energy E LUMO (D), and A composition in which E LUMO (H) > E LUMO (D).
5. In paragraph 1, The above host compound H has the highest occupied molecular orbital HOMO(H) with energy E HOMO (H) and the lowest unoccupied molecular orbital LUMO(H) with energy E LUMO (H), The above additional host compound D has the highest occupied molecular orbital HOMO (D) with energy E HOMO (D) and the lowest unoccupied molecular orbital LUMO (D) with energy E LUMO (D), The above organic molecule has the highest occupied molecular orbital HOMO (E) with energy E HOMO (E) and the lowest unoccupied molecular orbital LUMO (E) with energy E LUMO (E), E HOMO (H) > E HOMO (D), and the difference between the energy level of the highest occupied molecular orbital HOMO (E) of the organic molecule (E HOMO (E)) and the energy level H of the highest occupied molecular orbital HOMO (H) of the host compound H (E HOMO (H)) is -0.5 eV to 0.5 eV, and A composition in which E LUMO (H) > E LUMO (D), and the difference between the energy level of the lowest unoccupied molecular orbital LUMO (E) of the organic molecule (E LUMO (E)) and the energy level of the lowest unoccupied molecular orbital LUMO (D) of the additional host compound D (E LUMO (D)) is -0.5 eV to 0.5 eV.
6. In paragraph 1, The above host compound D or the above host compound H is a thermally activated delayed fluorescent (TADF) material, and The above TADF material is a composition having a ΔE ST value, which corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1), of less than 2500 cm⁻¹ .
7. In paragraph 1, A composition in which the emitter molecule F is a fluorescent or phosphorescent molecule.
8. A photoelectronic device comprising a composition according to any one of claims 1 to 7, The above optoelectronic device is an optoelectronic device selected from the group consisting of organic light-emitting diodes (OLEDs) and light-emitting electrochemical devices, a cell, an OLED sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser, and a down-conversion device.
9. In claim 8, the optoelectronic device comprises a substrate, an anode, a cathode, and a light-emitting layer, wherein the anode or cathode is disposed on the substrate, the light-emitting layer is arranged between the anode and the cathode, and the light-emitting layer comprises the composition.
10. A method for manufacturing a photoelectronic device using a composition according to any one of claims 1 to 7.

Description

Organic Molecules for Optoelectronic Devices The present invention relates to organic light-emitting molecules and their use in organic light-emitting diodes (OLEDs) and other optoelectronic devices. The present invention relates to organic light-emitting molecules and their use in organic light-emitting diodes (OLEDs) and other optoelectronic devices. The organic light-emitting molecule according to the present invention comprises or is composed of the structure of the following chemical formula I: Chemical Formula I Here Each of R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , and R XI is selected independently from the following group: Hydrogen; Halogen; C 1 - C 12 -alkyl, Optionally, C1 - C12 -alkyl in which one or more hydrogen atoms are independently substituted by R5 ; and A C6 - C18 -aryl in which one or more hydrogen atoms are optionally independently substituted by R5 . R 5 is independently selected from the group consisting of the following in each case: hydrogen; Optionally, one or more hydrogen atoms are independently substituted by C1 - C5 -alkyl substituents, C1 - C12 -alkyl or C6 - C18 -aryl. At least one of R I , R II , R III , R IV , and R V , and at least one of R VI , R VII , R VIII , R IX , or R X are selected from the following group: Optionally, one or more hydrogen atoms are independently substituted by R5 in a C1 - C12 -alkyl group; A C6 - C18 -aryl in which one or more hydrogen atoms are optionally independently substituted by R5 . In some embodiments of the organic molecule, each of R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , and R XI is independently selected from the group consisting of the following: Hydrogen; Deuterium; Halogen; Me; i Pr; t Bu; Cyclohexyl selectively substituted with one or more mutually independent substituents selected from the group consisting of Me, i Pr, t Bu, and phenyl(Ph); and Ph. which is selectively substituted with one or more mutually independent substituents selected from the group consisting of Me, i Pr, t Bu, cyclohexyl, and Ph. In some embodiments, one or more of R I , R II , R III , R IV , R V and one or more of R VI , R VII , R VIII , R IX , R X may be independently selected from the group consisting of Me, i Pr, t Bu, cyclohexyl and Ph. In a preferred embodiment, R IV and R VII are cyclohexyl. In a preferred embodiment, R II , R IV , R VII , and R IX are tBu. In some embodiments, R XI is selected from the group consisting of: Hydrogen; Deuterium; Halogen; Me; i Pr; t Bu; Cyclohexyl selectively substituted with one or more mutually independent substituents selected from the group consisting of Me, i Pr, t Bu, and phenyl(Ph); Ph. which is selectively substituted with one or more mutually independent substituents selected from the group consisting of Me, i Pr, t Bu, cyclohexyl, and Ph. In some embodiments, R XI may be selected from the group consisting of hydrogen, deuterium, Me, i Pr, t Bu, cyclohexyl and phenyl. In a preferred embodiment, R XI is hydrogen. In a preferred embodiment, R XI is Me. In a preferred embodiment, R XI is phenyl. In some embodiments, R I is identical to R X , R II is identical to R IX , R III is identical to R VIII , R IV is identical to R VII , and R V is identical to R VI , so that the organic molecule of these embodiments may comprise or be composed of the structure of Formula II: Chemical Formula II Along with the definition given above. In one embodiment, the organic molecule comprises or consists of the structure of the following formula Ia: Chemical formula Ia Here, R I , R II , R III , R IV , and R V are independent of each other. Hydrogen; Deuterium; Halogen; Me; i Pr; t Bu; Cyclohexyl selectively substituted with one or more mutually independent substituents selected from the group consisting of Me, i Pr, t Bu, and Ph; Ph. which is selectively substituted with one or more mutually independent substituents selected from the group consisting of Me, i Pr, t Bu, cyclohexyl, and Ph. In one embodiment, the organic molecule comprises or consists of the structure of formula Ia, wherein one or more of R I , R II , R III , R IV , and R V may be independently selected from the group consisting of Me, i Pr, t Bu, cyclohexyl and Ph. In one embodiment, the organic molecule comprises or consists of the structure of the following formula Ib: Chemical formula Ib Here, R I , R II , R III , R IV , and R V can be selected independently from the group consisting of the following: Hydrogen; Deuterium; Halogen; Me; i Pr; t Bu; Cyclohexyl selectively substituted with one or more mutually independent substituents selected from the group consisting of Me, i Pr, t Bu, and Ph; Ph. which is selectively substituted with one or more mutually independent substituents selected from the group consisting of Me, i Pr, t Bu, cyclohexyl, and Ph. In one embodiment, the organic molecule comprises or consists of the structure of the formula Ib, wherein at least two of R I , R II , R III , R IV , and R