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US 12,193,322 B2Granted
Organic light-emitting devices
AssigneeSamsung Display Co., Ltd.
InventorsHwan-Hee Cho, Mi-Kyung Kim, Se-Hun Kim, Dong-Hyun Kim, Chang-Woong Chu
Life of this patent
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Abstract
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).
Claims13
An organic light-emitting device, comprising:
- a substrate comprising a first sub-pixel region, a second sub-pixel region, and a third sub-pixel region;
- a first sub-pixel electrode disposed in the first sub-pixel region of the substrate,
- a first buffer layer disposed on the first sub-pixel electrode,
- a first emission layer disposed on the first buffer layer,
- a second sub-pixel electrode disposed in the second sub-pixel region of the substrate,
- a second buffer layer disposed on the second sub-pixel electrode,
- a second emission layer disposed on the second buffer layer,
- a third sub-pixel electrode disposed in the third sub-pixel region of the substrate,
- a third emission layer disposed on the third sub-pixel electrode, and
- a second electrode disposed opposite to the first sub-pixel electrode, the second sub-pixel electrode, and the third sub-pixel electrode,
- wherein the first emission layer emits a red color light, the second emission layer emits a green color light, and the third emission layer emits a blue color light, and only one of conditions (i) and (ii) below is met:
- (i) the first emission layer comprises at least one light-emitting material represented by any one of Formulas 1 and 2, and
- the second buffer layer consists of the at least one hole-transporting material represented by Formula 2(2), or
- (ii) the second emission layer comprises at least one light-emitting material represented by any one of the Formulas 1 and 2, and
- the first buffer layer consists of the at least one hole-transporting material represented by the Formula 2(2):
- wherein, in the Formulae 1 and 2,
- A1 is CR1 or N;
- A2 is CR2 or N;
- As is CR3 or N;
- A4 is CR4 or N;
- As is CR5 or N;
- A6 is CR6 or N;
- A7 is CR7 or N;
- As is CR8 or N;
- A9 is CR9 or N;
- A10 is CR10 or N;
- An 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 the group consisting of 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 are each independently a C1-C60 alkyl group, a C6-C60 aryl group, or a C1-C60 heteroaryl group;
- or two or more of R1 to R16 are optionally connected to each other to form a C6-C20 saturated ring or a Co-C20 unsaturated ring;
- Y is O, S, or C(R31)(R32);
- L1 to L3 are each independently selected from the group consisting of 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 C1-C10 heterocycloalkylene group, a substituted or unsubstituted C1-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 the group consisting of:
- i) a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, and —Si(Q1)(Q2)(Q3) (here, Q1 to Q3 are each independently a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted C6-C30 aryl group);
- and
- ii) a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group, each substituted with at least one substituent selected from the group consisting of 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-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) (here, Q1 to Q3 are each independently 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 the group consisting of:
- 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, each substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-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, C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group;
- and
- iv) a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group, each substituted with at least one substituent selected from the group consisting of 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-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 of 0 to 3;
- wherein, in the Formula 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 the group consisting of:
- 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, each substituted with at least one substituent selected from the group consisting of 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group;
- iv) a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group, each substituted with at least one substituent selected from the group consisting of 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-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
- v) —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), and —B(Q16)(Q17) (here, Q11 and Q17 are each independently a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, or a C2-C60 heteroaryl group);
- Ar13 and Ar14 are each independently selected from the group consisting of:
- i) a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group;
- and
- ii) a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group, each substituted with at least one substituent selected from the group consisting of 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 C1-C10 heterocycloalkyl group, a Cs-C10 cycloalkenyl group, a C1-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 connected to each other to form a fluorene moiety;
- and p and q are each independently an integer from 1 to 4.
74 more elements
Dependencies are inferred from the claim text.