Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-10164195-B2
Application number	US-201615284371-A
Country	US
Kind code	B2
Filing date	Oct 3, 2016
Priority date	Dec 22, 2015
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

An organic light-emitting device including: a first electrode; a second electrode facing the first electrode; an emission layer between the first electrode and the second electrode; a hole transport region between the first electrode and the emission layer; and an electron transport region between the emission layer and the second electrode, wherein the emission layer includes a first compound represented by Formula 1A or 1B, and at least one selected from the hole transport region and the electron transport region includes a second compound represented by Formula 2A or 2B:

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
an emission layer between the first electrode and the second electrode;
a hole transport region between the first electrode and the emission layer; and
an electron transport region between the emission layer and the second electrode,
wherein the emission layer comprises a first compound,
at least one selected from the hole transport region and the electron transport region comprises a second compound,
the first compound is represented by Formula 1A or 1B, and
the second compound is represented by Formula 2A or 2B:

wherein, in Formulae 1A, 1B, 2A, and 2B,
rings A 1 and A 2 are each independently a C 5 -C 60 carbocyclic group,
rings A 21 , A 22 , and A 23 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group, each substituted with at least one *-[(L 22 ) a22 -(R 22 ) b22 ],
each T 11 and each T 12 is independently carbon or nitrogen, any two or more of the three T 11 (s) Formula 2A are identical to or different from each other, T 13 is N or C(R 27 ), T 14 is N or C(R 28 ), any two or more of the three T 12 (s) Formula 2A are identical to or different from each other, the two T 11 (s) in Formula 2B are identical to or different from each other, the two T 12 (s) in Formula 2B are identical to or different from each other, and each bond between T 11 and T 12 is a single bond or a double bond; wherein the three T 11 (s) and the three T 12 (s) Formula 2A are not all nitrogen, and the two T 11 (s), the two T 12 (S), T 13 , and T 14 in Formula 2B are not all nitrogen,
rings A 21 , A 22 , and A 23 are each condensed to a central 7-membered ring in Formulae 2A and 2B, such that they each share a T 11 and a T 12 with the central 7-membered ring, and i) the case that rings A 21 A 22 , and A 23 in Formula 2A are all a benzene group substituted with at least one *-[(L 22 ) a22 -(R 22 ) b22 ] and ii) the case that rings A 21 and A 22 in Formula 2B are all a benzene group substituted with at least one *-[(L 22 ) a22 -(R 22 ) b22 ] are excluded;
X 21 is selected from O, S, Se, C(R 23 )(R 24 ), Si(R 23 )(R 24 ), and N-[(L 21 ) a21 -(R 21 ) b21 ],
L 1 , L 2 , L 21 , and L 22 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
a1, a2, a21, and a22 are each independently an integer selected from 0 to 5,
Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
b1 and b2 are each independently an integer selected from 1 to 5,
R 1 to R 4 , R 21 to R 24 , R 27 , and R 28 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ), and
c1, c2, b21, and b22 are each independently an integer selected from 0 to 4,
wherein a compound represented by Formula 1A, in which i) rings A 1 and A 2 are each a benzene group, ii) a1, a2, c1, and c2 are 0, iii) b1 and b2 are 1, and iv) Ar 1 and Ar 2 are each a naphthyl group, is excluded from being the first compound, and
at least one substituent of the substituted C 3 -C 10 cycloalkylene group, substituted C 1 -C 10 heterocycloalkylene group, substituted C 3 -C 10 cycloalkenylene group, substituted C 1 -C 10 heterocycloalkenylene group, substituted C 6 -C 60 arylene group, substituted C 1 -C 60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 alkyl group, substituted C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted C 1 -C 60 alkoxy group, substituted C 3 -C 10 cycloalkyl group, substituted C 1 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 1 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted C 6 -C 60 arylthio group, substituted C 1 -C 60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from the group consisting of:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condens

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Seulong
• Ito Naoyuki
• Kim Younsun
• Shin Dongwoo
• Lee Jungsub
• Lim Jino
• Jeong Hyein

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• H01L51/0052

  Electricity · mapped topic

• C09K11/06

  containing organic luminescent materials · CPC title

• H01L51/0067

  Electricity · mapped topic

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title