des brevets
`
`Europaisches
`Patentamt
`European
`Patent Office
`Office européen
`
`(11)
`
`EP 2977 378 A1
`
`(12)
`
`EUROPEAN PATENT APPLICATION
`
`(43) Date of publication:
`27.01.2016 Bulletin 2016/04
`
`(21) Application number: 15177484.1
`
`(51)
`
`Int Cl.:
`CO7F 7/08 (2096.01)
`HO1L 511/50 (2996.91)
`
`CO9K 11/00 (2006.07)
`HO5B 33/14 (2006.01)
`
`(22) Dateoffiling: 20.07.2015
`
`
`(84) Designated Contracting States:
`AL AT BE BG CH CY CZ DE DK EE ES FI FR GB
`GR HR HU IE ISITLILT LU LV MC MK MT NL NO
`PL PT RO RS SE SISK SMTR
`
`Designated Extension States:
`BA ME
`
`Designated Validation States:
`MA
`
`(30) Priority: 23.07.2014 KR 20140093540
`
`(71) Applicants:
`¢ Samsung Electronics Co., Ltd
`Gyeonggi-do 443-742 (KR)
`¢ Samsung SDI Co., Ltd.
`Yongin-si, Gyeonggi-do (KR)
`
`(72)
`
`Inventors:
`
`.
`
`*
`
`.
`
`.
`
`SON, Jhunmo
`443-803 Gyeonggi-do (KR)
`KIM, Sangmo
`443-803 Gyeonggi-do (KR)
`KIM, Hyunjung
`443-803 Gyeonggi-do (KR)
`JEON, Soonok
`443-803 Gyeonggi-do (KR)
`CHUNG, Yeonsook
`443-803 Gyeonggi-do (KR)
`HUH, Dalho
`443-803 Gyeonggi-do (KR)
`
`Representative: Zijlstra, Robert Wiebo Johan
`Elkington and Fife LLP
`Prospect House
`8 Pembroke Road
`
`Sevenoaks, Kent TN13 1XR (GB)
`
`JUNG, Yongsik
`443-803 Gyeonggi-do (KR)
`
`
`(54)
`
`CONDENSED CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING
`THE SAME
`
`(57)
`Claimed are condensed cyclic compound of Formulae 1A to 1D and their use in organic electroluminescent
`light-emitting devices (OLED).
`
`Formula 1A
`
`Formula 1B
`
`(Riadaz
`
`(Ridarn
`
`(Rada
`
`AN
`—{Ry2)
`Xy
`\
`AiArs (Riadaz
`=
`f
`XX .(Ry3)a3
`
`EP2977378A1
`
`°
`ty
`|
`N
`
`Xe
`X
`Der
`ic
`%
`[
`4
`Raadat
`oA it
`4 ST vy
`F
`\
`A 3
`Ar
`(Rizdaz
`
`(Ris)as
`
`I
`tN
`
`Xgom
`
`/
`xy
`v
`Xex7
`
`Xy
`>
`X>
`/
`Xs
`
`(Radarpry _—
`/
`Ar
`(Raz)a2
`
`™(Raadas
`
`
`
`Printed by Jouve, 75001 PARIS (FR)
`
`

`

`EP 2 977 378 A1
`
`Description
`
`FIELD OF THE INVENTION
`
`[0001] The presentdisclosure relates to a condensed cyclic compound and an organic light-emitting device including
`the same.
`
`BACKGROUND OF THE INVENTION
`
`[0002] Organic light-emitting devices (OLEDs) are self-emission devices that have wide viewing angles, high contrast
`ratios, shortresponse times. OLEDsalso have excellent brightness, driving voltage, and response speed characteristics,
`and produce full-color images.
`[0003]Atypical organic light-emitting device includes an anode, a cathode, and an organic layer that is disposed
`between the anode and the cathode and includes an emission layer. A hole transport region may be disposed between
`the anode and the emission layer, and an electron transport region may be disposed between the emission layer and
`the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and
`electrons provided from the cathode may move toward the emission layer through the electron transport region. Carriers,
`such as holes and electrons, are recombined in the emission layer to produce excitons. These excitons change from
`an excited state to a ground state, thereby generating light.
`[0004] Various types of organic light emitting devices are known. However, there still remains a need in OLEDs having
`low driving voltage, high efficiency, high brightness, and long lifespan.
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`SUMMARY OF THE INVENTION
`
`Provided are a novel condensed cyclic compound and an organic light-emitting device including the same.
`[0005]
`[0006] Additional aspects will be set forth in part in the description which follows and,
`in part, will be apparent from
`the description, or may be learned by practice of the presented exemplary embodiments.
`[0007] According to an aspect of an exemplary embodiment, a condensed cyclic compound is represented by Formulae
`1Ato 1D:
`
`Formula 1A
`
`Formula 1B
`
`(R42)
`
`tela
`
`ar
`(Ravan
`Re
`an? 2
`I‘ary
`
`|
`
`
`
`~(Ri3)
`
`13/a3
`
`x
`
`/ 8==
`xs
`\
`a
`
`ne
`Ly
`|
`
`//
`
`R
`(Ra4)a1
`Ar,
`“ bars (R42)a2
`\
`—_—
`Ars
`
`_
`
`(R13)a3
`
`Formula 1C
`
`Formula 1D
`
`

`

`EP 2 977 378 A1
`
`Rg
`" 1
`4
`
`ff
`
`De
`X7
`
`"s
`L,
`
`Xs——
`X
`*
`xy
`f
`pt
`ip=
`(
`Xe— i LAY
`Ars~ \
`Av
`(Ri2)a2
`
`7 (Riadat
`
`i
`
`(Ris)ax~
`
`~—
`
`~
`
`{Ria)a2
`
`x,~.
`“xX,
`|
`Xs
`
`—
`
`Ary
`
`(Radar
`
`6 Xs
`(Ri3)a3 Ats~—oh
`ar!
`2
`
`wherein in Formulae 1A to 1 D,
`Xz is Nor C(R,),
`Xq is N or C(Ro),
`X3 is N or C(R3),
`Xq is N or C(Ra),
`Xs is N or C(Rs),
`Xz, is N or C(Rg),
`X; is N or C(R;), and
`Xg is N or C(Rg);
`L, is each independently selected from a substituted or unsubstituted C3-C,, cycloalkylene group, a substituted or
`unsubstituted C,-C,, heterocycloalkylene group, a substituted or unsubstituted C3-C49 cycloalkenylene group, a
`substituted or unsubstituted C4-C4 9 heterocycloalkenylene group, a substituted or unsubstituted C,g-Cgy arylene
`group, a substituted or unsubstituted C,-Cgg heteroarylene group, a substituted or unsubstituted divalent non-
`aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heter-
`opolycyclic group;
`Ar, to Arg are each independently a group derived from a Cg-Cg non-condensed carbocyclic group or a C,-Cz non-
`condensed heterocyclic group,
`R, to Rg and Ry, to R,3 are each independently selected from a hydrogen, a deuterium, -F, -Cl, -Br, -l, a hydroxyl
`group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a
`carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt
`thereof, a substituted or unsubstituted C,-Cg, alkyl group, a substituted or unsubstituted C,-Cgp alkenyl group, a
`substituted or unsubstituted C2-Cg, alkynyl group, a substituted or unsubstituted C,-Cg,, alkoxy group, a substituted
`or unsubstituted C3-C 4, cycloalkyl group, a substituted or unsubstituted C,-C, 9) heterocycloalkyl group, a substituted
`or unsubstituted C5-C4) cycloalkenyl group, a substituted or unsubstituted C,-C,) heterocycloalkenyl group, a sub-
`stituted or unsubstituted Cg-Cgy aryl group, a substituted or unsubstituted Cg-Cgy aryloxy group, a substituted or
`unsubstituted Cg-Cgp arylthio group, a substituted or unsubstituted C,-Cg, heteroaryl group, a substituted or unsub-
`stituted a monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-
`aromatic condensed heteropolycyclic group, and -N(Q,)(Qo);
`a1 to a3 are each independently an integer selected from 1, 2, 3, 4, 5, and 6, provided that when a1 is 2 or more,
`two or more groups R,, are identical to or different from each, when a2 is 2 or more, two or more groups Ry» are
`identical to or different from each other, and whena3 is 2 or more, two or more groups R43 are identical to or different
`from each other;
`wherein in each of Formulae 1A to 1D, groups *-Ar,-(R44)
`other;
`at least one substituent of the substituted C3-C,, cycloalkylene group, the substituted C,-C,, heterocycloalkylene
`group, the substituted C5-C49 cycloalkenylene group, the substituted C;-C,, heterocycloalkenylene group, the sub-
`stituted Cs-Cgp arylene group, the substituted C,-Cg, heteroarylene group, the substituted divalent non-aromatic
`condensedpolycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted
`C,-Cgy alkyl group, the substituted C.-C,, alkenyl group, the substituted C5-Cgg alkynyl group, the substituted C,-Cgp
`alkoxy group, the substituted C3-C,, cycloalkyl group, the substituted C,-C,, heterocycloalkyl group, the substituted
`
`at -Alo-(Ry2)a2 and *-Ar3-(R13)43 are not identical to each
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`EP 2 977 378 A1
`
`C.3-C49 cycloalkenyl group, the substituted C,-C,, heterocycloalkenyl group, the substituted Cg-Cg,y aryl group, the
`substituted C,-Cg, aryloxy group, the substituted Cg-Cg,g arylthio group, the substituted C,-Cg, heteroaryl group,
`the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic
`condensed heteropolycyclic group may be selected from
`a deuterium, -F, -Cl, -Br, -!, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a
`hydrazine group, a hydrazone group, a carboxylic acid graup or a salt thereof, a sulfonic acid group or a salt thereof,
`a phosphoric acid group or a salt thereof, a C,-Cgp alkyl group, a C5-Cgg alkenyl group, a Co-Cgp alkynyl group, and
`a C4-Cgp alkoxy group;
`a Co-Cegp alkyl group, a C2-Cgo alkenyl group, a Co-Cgp alkynyl group, and a C,-Cg, alkoxy group, each substituted
`with at least one selected from deuterium, -F, -Cl, -Br, -], a hydroxyl group, a cyano group, a nitro group, an amino
`group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic
`acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C4, cycloalkyl group, a C,-C49 hetero-
`cycloalkyl group, a C3-C,, cycloalkenyl group, a C,-C,, heterocycloalkenyl group, a Cg-Cgy aryl group, a Cg-Cey
`aryloxy group, a Cg-Ce, arylthio group, a C,-Cg, heteroaryl group, a monovalent non-aramatic condensedpolycyclic
`group, a monovalent non-aromatic condensed heteropolycyclic group, and -N(Q,4)(Q,9);
`aC,-C,, cycloalkyl group, aC ,-C,, heterocycloalkyl group, a C3-C,, cycloalkenyl group, aC,-C,, heterocycloalkeny|
`group, a Cg-Cgg aryl group, a Cg-Cg, aryloxy group, a Cg-Cgy arylthio group, aC ,-Ce, heteroaryl group, a monovalent
`non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
`aC,-C,, cycloalkyl group, a C,-C,, heterocycloalkyl group, a C3-C,, cycloalkenyl group, aC ,-C,, heterocycloalkeny|
`group, a Cg-Cgg aryl group, a Cg-Cgg aryloxy group, a Cg-Cgy arylthio group, aC ,-Cgq heteroaryl group, a monovalent
`non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each
`substituted with at least one selected from a deuterium, -F, -Cl, -Br, -1, a hydroxyl group, a cyano group, a nitro
`group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt
`thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C,-Cgy alkyl group, a
`Co-Cegg alkenyl group, a Co-Cgy alkynyl group, a Co-Cgy alkoxy group, a C3-C4) cycloalkyl group, a C,-C,, hetero-
`cycloalkyl group, a C3-C,, cycloalkenyl group, a C,-C,, heterocycloalkenyl group, a Cg-Cgy aryl group, a Cg-Ceg
`aryloxy group, a Cg-Cgg arylthio group, a Cy-Ce, heteroaryl group, a monovalent non-aromatic condensedpolycyclic
`group, a monovalent non-aromatic condensed heteropolycyclic group, and -N(Q54)(Qz9); and
`-N(Q34)(Q39);
`wherein Qy, Q5, Qy4, Qy2, Qg1, Qo2, Q3, and Qgy are each independently selected fram
`a hydrogen, a C4-Cgg alkyl group, a Co-Ceg alkenyl group, a Co-Cgg alkynyl group, a C,-C¢gp alkoxy group, a C3-C49
`cycloalkyl group, a C,-C4, heterocycloalkyl group, a C3-C 4, cycloalkeny! group, a C4-C4, heterocycloalkenyl group,
`a Ceg-Cgg aryl group, a C4-Cgg heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a
`monovalent non-aromatic condensed heteropolycyclic group; and
`aC,-C,, cycloalkyl group, a C,-C,, heterocycloalkyl group, a C3-C,, cycloalkenyl group, aC,-C,, heterocycloalkeny|
`group, a Cg-Cgp aryl group, a C,-Cg, heteroaryl group, a monovalent non-aromatic condensed polycyclic group,
`and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from
`a deuterium, -F, -Cl, -Br, -i, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a
`hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group ora salt thereof,
`a phosphoric acid group or a salt thereof, a C,-Cg, alky! group, a Cy-Cg,q alkoxy group, a C3-C,, cycloalkyl group,
`a C,-Cyg heterocycloalkyl group, a C3-C4,9 cycloalkenyl group, a C,-C,, heterocycloalkenyl group, a Cg-Cgp aryl
`group, a C4-Cgy heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-
`aromatic condensed heteropolycyclic group.
`
`[0008] Another aspect provides an organic light-emitting device including:
`
`a first electrode;
`a second electrode; and
`an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes
`an emission layer, and further includes at least one condensed cyclic compound.
`
`BRIEF DESCRIPTION OF THE DRAWINGS
`
`[0009] These and/or other aspects will become apparent and more readily appreciated from the following description
`of the exemplary embodiments, taken in conjunction with FIG. 1 which is a schematic view of an organic light-emitting
`device according to an embodiment.
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`DETAILED DESCRIPTION OF THE EMBODIMENTS
`
`EP 2 977 378 A1
`
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`[0010] Reference will now be made in detail to exemplary embodiments, examples of which areillustrated in the
`accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present
`exemplary embodiments may havedifferent forms and should not be construed as being limited to the descriptions set
`forth herein. Accordingly, the exemplary embodiments are merely described below, by referring to the figures, ta explain
`aspects. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed
`items. Expressions such as “at least one of," when preceding a list of elements, modify the entire list of elements and
`do not modify the individual elements ofthelist.
`10
`[0011]=It will be understood that when an element is referred to as being "on" another element, it can be directly in
`contact with the other element or intervening elements may be present therebetween. In contrast, when an element is
`referred to as being "directly on" another element, there are no intervening elements present.
`[0012]
`It will be understood that, although the terms first, second, third etc. may be used herein to describe various
`elements, components, regions, layers, and/or sections, these elements, components, regions, layers, and/or sections
`should not be limited by these terms. These terms are only usedto distinguish one element, component, region, layer,
`or section from another element, component, region, layer, or section. Thus, a first element, component, region, layer,
`or section discussed below could be termed a second element, component, region, layer, or section without departing
`from the teachings of the present embodiments.
`[0013] The terminology used herein is for the purpose of describing particular embodiments only and is not intended
`to be limiting. As used herein, the singular forms "a," "an," and "the" are intended to include the plural forms as well,
`unlessthe context clearly indicates otherwise.
`[0014]
`It will be further understood that the terms “comprises” and/or “comprising,” or "includes" and/or “including”
`when usedin this specification, specify the presence of stated features, regions, integers, steps, operations, elements,
`and/or components, but do not preclude the presenceor addition of one or more other features, regions, integers, steps,
`operations, elements, components, and/or groups thereof.
`"upper" and the like, may be used herein
`"above,"
`[0015]
`Spatially relative terms, such as "beneath," "below," "lower,"
`for ease of description to describe one element or feature’s relationship to another element(s) or feature(s) as illustrated
`in the figures. It will be understood that the spatially relative terms are intended to encompassdifferent orientations of
`the device in use or operation in addition to the orientation depicted in the figures. For example, if the device in the
`figures is turned over, elements described as "below" or “beneath” other elements or features would then be oriented
`"above" the other elements or features. Thus, the exemplary term "below" can encompassboth an orientation of above
`and below. The device may be otherwise oriented (rotated 90 degreesor at other orientations) and the spatially relative
`descriptors used herein interpreted accordingly.
`[0016]
`"About" or "approximately" as used herein is inclusive of the stated value and means within an acceptable
`range of deviation for the particular value as determined by one ofordinary skill in the art, considering the measurement
`in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement
`system). For example, "about" can mean within one or more standard deviations, or within + 30%, 20%, 10%, 5% of
`the stated value.
`
`30
`
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`
`[0017] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning
`as commonly understood by one of ordinary skill in the art to which this invention belongs.It will be further understood
`that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning thatis
`consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in
`an idealized or overly formal sense unless expressly so defined herein.
`[0018] Exemplary embodiments are described herein with reference to cross section illustrations that are schematic
`illustrations of idealized embodiments. As such, variations from the shapesofthe illustrations as a result, for example,
`of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be
`construed aslimited to the particular shapes of regions asillustrated herein but are to include deviations in shapes that
`result, for example, from manufacturing. For example, a region illustrated or described asflat may, typically, have rough
`and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded. Thus, the regions illustrated in
`the figures are schematic in nature and their shapes are not intendedto illustrate the precise shape of a region and are
`not intended to limit the scope of the present claims.
`[0019] An aspect provides a condensed cyclic compound represented by Formulae 1A to 1 D below:
`
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`

`EP 2 977 378 A1
`
`Formula 1A
`
`Formula 1B
`
`xy
`
`\
`
`Ar,
`
`—
`Ar.
`xx AS
`(Ri3)a3
`
`Formula 1C
`
`Formula 1D
`
`Ro
`
`|1
`
`R
`
`I"
`Ly
`|
`Pes
`x
`x pt_
`Xe—
`neh LAK 11?a1
`si
`Ar” \
`” 3
`Ar
`(Ri3)a3
`Vv
`(Ri2)a2
`
`(Ri1)
`
`x
`Po
`*X,
`X7
`a /
`5
`(Ris)as~qr,—_ fs
`/
`Aro
`
`Ary
`
`(Rai)at
`
`N
`
`(Ri2)a2
`
`In Formulae 1A to 1 D,
`X, may be N or C(R,),
`Xz may be N or C(R>),
`X3 may be N or C(R3),
`Xq4 may be N or C(Ry),
`Xs may be N or C(Rs),
`Xg may be N or C(Rg),
`Xz may be N or C(R7), and
`Xg may be N or C(Rg).
`
`ON
`
`[0020]
`
`In some embodiments, in Formulae 1A to 1 D,
`
`X4 may be C(R;),
`X_ may be C({Ro),
`X3 may be C(R3),
`Xq4 may be C(Ry),
`Xs may be C(Rs),
`Xg may be C({Rg),
`X7 may be C(R7), and
`Xg may be C(Rg).
`In some embodiments,
`one, two, or three elements selected from Xz to Xg in Formula 1A may be N;
`one, two, or three elements selected from X4 and X3 to Xg in Formula 1 B maybe N;
`one, two, or three elements selected from X4, Xz and X, to Xg in Formula 1C may be N; and
`
` (Raadat
`
`\ars (Ri2)az
`
`— R
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`EP 2 977 378 A1
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`one, two, or three elements selected from X, to X3 and Xz to Xg in Formula 1 D may be N,
`but they are notlimited thereto.
`
`[0021]
`
`For example, in Formulae 1A to 1D,
`
`X, is N, Xz is C(R,), X3 is C(R3), X4 is C(Ry), Xs is C(Rs), Xg is C(Rg), X7 is C(Rz), and Xz is C(Rg);
`X, is C(R,), Xo is N, X3 is C(R3), X4 is C(R4), Xs is C(Rzg), Xg is C(Rg), X7 is C(Rz), and Xg is C(Rg);
`Xz is C(R4), Xq is C(Ra), X3 is N, Xq is C(Ry), Xs is C(Rs), Xg is C(Rg), X7 is C(Rz), and Xg is C(Rg);
`Xz is C(R4y), Xp is C(R9), X3 is C(R3), X4 is N, Xs is C(Rs), Xg is C(Rg), X7 is C(Rz), and Xz is C(Rg);
`X_ is C(R4), Xq is C(Ro), X3 is C(R3), X4 is C(Ry), Xs is N, Xg is C(Rg), X7 is C(R7), and Xz is C(Rg);
`Xz is C(R4), Xo is CCR), X3 is C(R3), X4 is C(R4), Xs is C(Rg), Xg is N, X7 is C(R7), and Xg is C(Rg);
`Xz is C(R4), Xq is CCR), X3 is C(R3), X4 is C(Ry), Xs is C(Re), Xg is C(Rg), X7 is N, and Xg is C(Rg);
`Xz
`is C(R4), Xo is C(Ro), X3 is C(R3), X4 is C(Ry), Xs is C(Rs), Xg is C(Rg), X7 is C(Rz), and Xg is N;
`X, is C(Ry), Xo is C(Rz), X3 is C(R3), X4 is C(Ry), Xs is C(Re), Xg iS N, X7 is C(Rz), and Xg is N;
`Xz
`is C(Ry), X2 is C(R2), X3 is C(R3), X4 is C(Ry), Xs is N, Xg is C(Rg), X7 is N, and Xg is C(Rg);
`Xz is C(R4), Xq is N, X3 is C(Rg), X4 is C(Ry), Xs is C(Rs), Xg is C(Rg), X7 is N, and Xg is C(Rg);
`X, is C(R4), Xz is C(Ro), X3 is C(R3), X4 is N, X, is N, Xg is C(Rg), X7 is C(Rz), and Xg is C(Rg); or
`X,
`is C(R,), Xp is C(R»), X3 is N, Xq is C(Ry), Xs is C(Rs), Xg is N, X7 is C(R7), and Xg is C(Rg), but they are not
`limited thereto.
`
`= =
`
`in Formulae 1A and 1 D may be each independently selected from a substituted or unsubstituted C3-C49 cy-
`L,
`cloalkylene group, a substituted or unsubstituted C,-C,, heterocycloalkylene group, a substituted or unsubstituted
`C3-C49 cycloalkenylene group, a substituted or unsubstituted C,-C4) heterocycloalkenylene group, a substituted or
`unsubstituted Cg-Cg, arylene group, a substituted or unsubstituted C,-Cgy heteroarylene group, a substituted or
`unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-
`aromatic condensed heteropolycyclic group.
`
`For example, L, in Formulae 1A to 1 D may be each independently selected from a substituted or unsubstituted
`[0022]
`C_-Ca9 arylene group, a substituted or unsubstituted C ,-C, heteroarylene group, a substituted or unsubstituted divalent
`non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heter-
`opolycyclic group.
`[0023]
`In some embodiments, L,
`
`in Formulae 1A to 1 D may be selected from
`
`a phenylene group, a naphthylene group, a fluorenylene group, a phenanthrenylene group, an anthracenylene
`group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene
`group, a pyrimidinylene group, a pyridazinylene group, and a triazinylene group; and
`a phenylene group, a naphthylene group, a fluorenylene group, a phenanthrenylene group, an anthracenylene
`group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene
`group, a pyrimidinylene group, a pyridazinylene group, and a triazinylene group, each substituted with at least one
`selected from a deuterium, -F, -Cl, -Br, -l, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino
`group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a
`salt thereof, a phosphoric acid group or a salt thereof, a C,-Cy alkyl group, a C,-C5, alkoxy group, a phenyl group,
`a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl
`group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl
`group,
`but they are not limited thereto.
`
`[0024]
`
`In some embodiments, L,
`
`in Formulae 1A to 1 D may be selected from
`
`a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group; and
`a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group,
`each substituted with at least one selected from a deuterium, -F, -Cl, -Br, -l, a hydroxyl group, a cyano group, a nitro
`group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt
`thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C,-C,, alkyl group, a
`C,-C49 alkoxy group, a phenyl group, and a naphthyl group.
`Ar, to Ars in Formulae 1A to 1 D may be each independently a group derived from a C.-Cg non-condensed carbocyclic
`group or a C4-C7 non-condensed heterocyclic group.
`
`[0025]
`
`In some embodiment, Ar, and Arg in Formulae 1A to 1 D may be each independently represented by one of
`
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`15
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`20
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`25
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`30
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`35
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`40
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`45
`
`50
`
`5S
`
`

`

`Formulae 2-1 to 2-40 below:
`
`EP 2 977 378 A1
`
`xe
`‘X13
`
`JagXs
`
`Formula 2-1
`
`xteLk
`
`Xis
`
`Formula 2-7
`
`*
`
`xe
`X43
`
`x
`
`X
`
`x / ye
`
`Xe
`
`Kh
`
`X2
`
`/
`
`*
`
`X42
`
`xa
`X2
`
`wy,
`
`X3
`
`*
`
`Formula 2-2
`
`Formula 2-3
`
`Formula 2-4
`
`Formula 2-5
`
`X42
`
`X12
`
`‘8
`Xt
`is
`X14
`ow v4 A om
`X
`*
`XQ
`Formula 2-8
`Formula 2-9
`
`*
`
`1
`
`Xi2
`
`Xi we
`xX i"
`7X2 A ka
`X43
`X43
`Formula 2-10
`Formula 2-11
`
`Xx
`xq <x,
`KOSy
`* x3
`
`X12
`
`oe
`xr
`¥r
`aoXs
`
`Xa
`
`ke
`
`Formula 2-13
`
`Formula 2-14
`
`2
`4X12-X49
`7X2~Xq3
`XK
`~ X3
`Xa4
`\
`Xa
`\
`FE Fo» RR >»
`oe
`x
`Roy
`Xs
`XygoM15
`Xq7A185
`Formula 2-15
`Formula 2-16
`Formula 2-17
`
`*
`
`xeye,
`
`Formula 2-6
`
`Formula 2-12
`
`X42~/
`Xa
`
`X13
`\1
`4
`Xie*2
`Formula2-18
`
`Z 12 Xa
`Xqo~
`WA i
`11
`x
`Kya
`
`*
`
`Pen, ZX
`147%
`—
`Xo~—X.
`S
`/* N ie A
`x7
`1
`X44
`\
`1
`\
`Pak of
`—Ky3
`XeXa
`oh
`
`Pa
`
`Formula 2-20
`
`Formula 2-21.
`
`Formula 2-22
`
`Formula 2-23
`
`Xe4
`Formula2-24
`
`71K
`Xa
`
`\2
`
`Xa*8
`Formula 2-19
`
`1
`
`x
`Xx
`Xi 4
`Xai 12
`I
`Xa
`X
`sx ao Xap
`Formula 2-26
`Formula 2-27
`
`aN
`Xe
`i ye
`aKa
`Formula 2-28
`
`xx
`i
`"°
`No X14
`ZN
`Xis
`Formula 2-29
`
`*
`
`eonx7
`Formula 2-30
`
`N
`
`X>
`
`X43
`Formula 2-31
`
`x
`x ‘sx,
`N
`X12
`ae xT
`Formula 2-32
`
`X
`x7 on
`|
`ZN. aX
`x7
`Formula 2-33
`
`*
`
`2X43
`\
`Xieot
`Formula 2-34
`
`KON,
`
`14
`
`Xx
`7X3
`“
`x
`N
`Y
`RON _
`Xia Xe
`Formula 2-35
`
`4
`
`Xy2~
`71K
`1"
`\
`N _/Ma
`Sy€s
`Formula 2-37
`
`—
`
`x
`Xi
`Prk
`7S
`x7
`ut
`\
`‘
`”
`u
`N
`Ar
`xeoX Ngo
`Formula 2-38
`Formula 2-39
`
`RON
`
`xX
`P*rXs
`x7
`.
`hi
`Ms
`aa SxXs
`Formula 2-40
`
`X12~
`
`x4
`
`7
`
`\2
`“
`/
`N
`#7 ONY
`Xi 8
`Formula 2-36
`
`*
`
`*
`
`wherein in Formulae 2-1 to 2-40,
`
`X41 is O, S, N(Z44) or C(Z44a)(Z4 4p), X42 is O, S, N(Z42) or C(Z42q)(Z 42H), X13 is O, S, N(Z43) or C(Z43q)(Z4 3p), X14
`is O, S, N(Z44) or C(Z44q)(Z44p), X45 is O, S, N(Z45) of C(Z45a)(Zi5p), X46 is O, S, N(Zy9) or C(Z4¢q)(Z 16):
`X, is N or C(Z,), Xq is N or C(Z3), X3 is N or C(Z3), Xq is N or C(Z,), X5 is N or C(Zs5), and Xg is N or C(Z¢);
`241 10 216, 2444 10 Zig4, 24 4p 10 Zigp, and Z, to Z, are each independently a hydrogen, or a binding site to each of
`
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`50
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`5S
`
`

`

`EP 2 977 378 A1
`
`R41, Ry, and R,3 in Formulae 1A to 1 D; and
`*is a binding site to Si in Formulae 1A to 1 D.
`
`For example, Ar, to Ars in Formulae 1 A to 1 D may be each independently selected from groups represented
`[0026]
`by Formulae 2-5 to 2-7, 2-15, 2-22, 2-23, and 2-24, but they are notlimited thereto.
`[0027]
`!n some embodiments, Ar, to Ars in Formulae 1A to 1 D may be each independently a group derived from a
`compound selected from a benzene, a pyridine, a pyrazine, a pyrimidine, a pyridazine, a triazine, a furan, a thiophene,
`a pyrrole, an imidazole, a triazole, a cyclohexane, a tetrahydro-2H-pyran, a piperidine, a tetrahydro-2H-thiopyran, a
`(2Z,4Z,6Z)-oxepine, a (2Z,4Z2,6Z)-1H-azepine, and a (2Z,4Z,6Z)-thiepine.
`[0028] R,toRgandR,, to R,3 in Formulae 1A to 1D may be each independently selected from a hydrogen, adeuterium,
`-F, -Cl, -Br, -|, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a
`hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid
`group or a salt thereof, a substituted or unsubstituted C,-Cg, alkyl group, a substituted or unsubstituted C>-Cg, alkenyl
`group, a substituted or unsubstituted C5-Cg, alkynyl group, a substituted or unsubstituted C,-Cg, alkoxy group, a sub-
`stituted or unsubstituted C3-C,, cycloalkyl group, a substituted or unsubstituted C,-C,,) heterocycloalkyl group, a sub-
`stituted or unsubstituted C5-C,, cycloalkenyl group, a substituted or unsubstituted C,-C,, heterocycloalkenyl group, a
`substituted or unsubstituted Cg-Cgy aryl group, a substituted or unsubstituted Cg.-Cg, aryloxy group, a substituted or
`unsubstituted Cg-Cgy arylthio group, a substituted or unsubstituted C ,-C,, heteroaryl group, a substituted or unsubstituted
`a monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic con-
`densed heteropolycyclic group, and -N(Q,)(Qz).
`
`Q, and Q, maybe each independently selected from
`a hydrogen, a C,-Cgp alkyl group, a C2-Cgy alkenyl group, a C2-Cgg alkynyl group, a C;-Cgp alkoxy group, a C3-C4
`cycloalkyl group, a C,-C,, heterocycloalkyl group, a C3-C,, cycloalkeny! group, a C,-C,, heterocycloalkeny| group,
`a C.-Cgp aryl group, a C,-Cgy heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a
`monovalent non-aromatic condensed heteropolycyclic group; and
`aC,-C,, cycloalkyl group, aC,-C,, heterocycloalkyl group, a C3-C,, cycloalkenyl group, aC,-C,,) heterocycloalkeny|
`group, a Cg-Cegg aryl group, a C,-Cg, heteroaryl group, a monovalent non-aromatic condensed polycyclic group,
`and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from
`a deuterium, -F, -Cl, -Br, -l, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a
`hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group ora salt thereof,
`a phosphoric acid group or a salt thereof, a C;-Cgp alkyl group, a C4-Cgg alkoxy group, a C3-C4, cycloalkyl group,
`a C,-Cy49 heterocycloalkyl group, a C3-C49 cycloalkenyl group, a Cy-Cj) heterocycloalkenyl group, a Cg-Cgp aryl
`group, a C4-Cgg heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-
`aromatic condensed heteropolycyclic group.
`
`[0029]
`
`Insome embodiments, R, to Rg and R,, to R;3 in Formulae 1A to 1D may be each independently selected from
`
`a hydrogen, a deuterium, -F, -Cl, -Br, -], a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino
`group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a
`salt thereof, a phosphoric acid group or a salt thereof, a C,-Cy, alkyl group, and a C,-Co, alkoxy group;
`a C,-Cy, alkyl group and a C,-Cyy alkoxy group, each substituted with at least one selected from a deuterium, -F,
`-Cl, -Br, -l, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group,
`a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric
`acid group or a salt thereof, a phenyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group;
`a cyclopentyl group, a cyclohexy! group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a
`piperidinyl group, a tetrahydro-2H-pyranyl group, a tetrahydro-2H-thiopyranyl group, a phenyl group, a fluorenyl
`group, a dibenzosilolyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl
`group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a furanyl group, a thiophenyl
`group, a thiazoly| group, an isothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazalyl
`group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl
`group;
`a cyclopentyl group, a cyclohexy! group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a
`piperidinyl group, a tetrahydro-2H-pyranyl group, a tetrahydro-2H-thiopyranyl group, a phenyl group, a fluocrenyl
`group, a dibenzosilolyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl
`group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a furanyl group, a thiopheny|
`group, a thiazoly| group, an isothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl
`group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiopheny|
`
`10
`
`15
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`20
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`30
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`
`40
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`
`50
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`5S
`
`

`

`EP 2 977 378 A1
`
`group, each substituted with at least one selected from a deuterium, -F, -Cl, -Br, -l, a hydroxyl group, a cyano group,
`a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group
`or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C4-Cy9 alkyl
`group, a C4-C>9 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group,
`a cycloheptenyl group, a piperidinyl group, a tetrahydro-2H-pyranyl group, a tetrahydro-2H-thiopyranyl group, a
`phenyl group, a fluorenyl group, a dibenzosilolyl group, a pyrrolyl group, an imidazolyl group, a pyrazoly! group, a
`pyridinyl group, a pyraziny! group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a
`furanyl group, a thiopheny! group, a thiazolyl group, an isothiazolyl group, an isoxazolyl group, an oxazolyl group,
`a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl
`group, a dibenzothiophenyl group, and -N(Q3,)(Q39); and
`-N(Q,)(Qz),
`wherein Qy, Qo, Q31, and Q35 are each independently selected from
`a hydrogen, a C,-Co5y alkyl group, a C,-C5, alkoxy group, a cyc