Organic light-emitting devices

摘要

An organic light-emitting device includes: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode. The organic layer includes an emission layer, and the emission layer includes at least one light-emitting material represented by one of Formulas 1 and 2. The organic layer further includes at least one hole-transporting material represented by one of Formulas 2(1) and 2(2).;;;;

主权项

1. An organic light-emitting device comprising:
a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, and comprising an emission layer, wherein the emission layer comprises at least one light-emitting material represented by Formula 1 or Formula 2, and wherein the organic layer further comprises at least one hole-transporting material represented by Formula 2(1) or Formula 2(2), wherein, in Formulas 1 and 2, A1 is CR1 or N; A2 is CR2 or N; A3 is CR3 or N; A4 is CR4 or N; A5 is CR5 or N; A6 is CR6 or N; is CR7 or N; A8 is CR8 or N; A9 is CR9 or N; A10 is CR10 or N; A11 is CR11 or N; A12 is CR12 or N; A13 is CR13 or N; A14 is CR14 or N; A15 is CR15 or N; and A16 is CR16 or N; R1 to R16 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a C1-C60 alkyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, and —N(Q1)(Q2)(Q3), Q1 to Q3 each independently being a C1-C60 alkyl group, a C6-C60 aryl group, or a C1-C60 heteroaryl group; two or more of R1 to R16 optionally combine to form a C6-C20 saturated ring or a C6-C20 unsaturated ring; Y is O, S, or C(R31)(R32); L1 to L3 are each independently selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C10 heterocycloalkylene group, a substituted or unsubstituted C2-C10 heterocycloalkenylene group, and a substituted or unsubstituted C1-C60 heteroarylene group; n1 to n3 are each independently an integer of 0 to 3; Ar1 to Ar3 are each independently selected from:
i) a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, and —Si(Q1)(Q2)(Q3), Q1 to Q3 each independently being a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted C6-C30 aryl group; andii) a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group substituted with at least one substituent selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and —Si(Q1)(Q2)(Q3), Q1 to Q3 each independently being a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted C6-C30 aryl group; Z1 to Z4, R31, and R32 are each independently selected from:
i) a hydrogen atom, a deuterium atom, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;ii) a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group substituted with at least one substituent selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group;iii) a C3-C10 cycloalkyl group, C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group; andiv) a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group substituted with at least one substituent selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group; o1 to o4 are each independently an integer from 0 to 3; wherein, in Formulas 2(1) and 2(2), X11 is CR11 or N; X12 is CR12 or N; X13 is CR13 or N; X14 is CR14 or N; X15 is CR15 or N; X16 is CR16 or N; X17 is CR17 or N; X18 is CR18 or N; X19 is CR19 or N; X20 is CR20 or N; X21 is CR21 or N; X22 is CR22 or N; X23 is CR23 or N; and X24 is CR24 or N; Z5, Z6, and R11 to R24 are each independently selected from:
i) a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;ii) a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group substituted with at least one substituent selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group;iii) a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group;iv) a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group substituted with at least one substituent selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group; andv) —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), and —B(Q16)(Q17), Q11 to Q17 each independently being a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, or a C1-C60 heteroaryl group; Ar13 and Ar14 are each independently selected from:
i) a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group; andii) a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group substituted with at least one substituent selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group; Z11 and Z12 are each independently selected from:
i) a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;ii) a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group substituted with at least one substituent selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group;iii) a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group; andiv) a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group substituted with at least one substituent selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group; and p and q are each independently an integer from 1 to 4.