US 12,410,130 B2
Light-emitting device and electronic apparatus including the same
Daewoong Lee, Yongin-si (KR); Hyomin Ko, Yongin-si (KR); and Bora Lee, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Oct. 7, 2021, as Appl. No. 17/450,175.
Claims priority of application No. 10-2021-0026473 (KR), filed on Feb. 26, 2021.
Prior Publication US 2022/0285619 A1, Sep. 8, 2022
Int. Cl. H10K 85/60 (2023.01); C07C 211/61 (2006.01); C07D 209/86 (2006.01); C09K 11/06 (2006.01); H10K 50/15 (2023.01); H10K 50/17 (2023.01); H10K 50/19 (2023.01); H10K 102/00 (2023.01)
CPC C07D 209/86 (2013.01) [C07C 211/61 (2013.01); C09K 11/06 (2013.01); H10K 85/633 (2023.02); H10K 85/636 (2023.02); C07C 2601/14 (2017.05); C07C 2603/18 (2017.05); C07C 2603/97 (2017.05); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1014 (2013.01); C09K 2211/1018 (2013.01); H10K 50/15 (2023.02); H10K 50/17 (2023.02); H10K 50/19 (2023.02); H10K 85/615 (2023.02); H10K 85/624 (2023.02); H10K 85/6572 (2023.02); H10K 2102/351 (2023.02)] 17 Claims
 
1. A light-emitting device comprising:
an anode;
a cathode;
an interlayer comprising an emission layer between the anode and the cathode; and
a hole transport region between the anode and the emission layer,
wherein the hole transport region comprises a first layer and a second layer,
the first layer is between the anode and the second layer,
the first layer comprises a first compound represented by Formula 1,
the second layer comprises a second compound, and
a charge mobility of the first compound is lower than a charge mobility of the second compound:

OG Complex Work Unit Chemistry
wherein, in Formula 1,
L11 is a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
a11 is an integer from 0 to 5,
Rx and Ry are each a group represented by Formula 2, and Rx and Ry are identical to each other,

OG Complex Work Unit Chemistry
wherein, in Formula 2,
R21 is a cyclopentyl group, a cyclohexyl group, a tert-butyl group, or a C5-C10 alkyl group, and
R10a is:
deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with -D, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13), —C(Q11)(Q12)(Q13), —B(Q11)(Q12), —N(Q11)(Q12), —P(Q11)(Q12), —C(═O)(Q11), —S(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), —P(═S)(Q11)(Q12), or any combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each unsubstituted or substituted with -D, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q21)(Q22)(Q23), —C(Q21)(Q22)(Q23), —B(Q21)(Q22), —N(Q21)(Q22), —P(Q21)(Q22), —C(═O)(Q21), —S(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22) or —P(═S)(Q21)(Q22), or any combination thereof; or
—Si(Q31)(Q32)(Q33), —C(Q31)(Q32)(Q33), —B(Q31)(Q32), —N(Q31)(Q32), —P(Q31)(Q32), —C(═O)(Q31), —S(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or —P(═S)(Q31)(Q32),
wherein Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently: hydrogen; -D; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with -D, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof,
* indicates a binding site to a neighboring atom,
wherein R11 is a group represented by one selected from Formulae 6-1 to 6-173:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein, in Formulae 6-1 to 6-173,
i-Pr is an isopropyl group;
t-Bu is a tert-butyl group;
Ph is a phenyl group;
1-Naph is an 1-naphthyl group;
2-Naph is a 2-naphthyl group; and
* indicates a binding site to a neighboring atom, and
wherein when R11 is represented by one selected from Formulae 5-10 to 5-13 and X51 is C(R53)(R54) and R53 and R54 are each independently a C1-C20 alkyl group, then R21 is a tert-butyl group, wherein b54 is an integer from 1 to 4, b55 is an integer from 1 to 3, and R51 and R52 are each independently hydrogen, -D, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkyl group substituted with at least one phenyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-fluorene-benzofluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, —Si(Q31)(Q32)(Q33), —C(Q31)(Q32)(Q33), —N(Q31)(Q32), or —B(Q31)(Q32),

OG Complex Work Unit Chemistry