Heterocyclic compound and organic light-emitting device
A heterocyclic compound represented by Formula 1: wherein, in Formula 1, groups and variables are the same as described in the specification.
1 . A heterocyclic compound represented by Formula 1:
wherein, in Formula 1,
X 1 is N or C(R 1 ), X 2 is N or C(R 2 ), and X 3 is N or C(R 3 ), wherein i) one selected from X 1 to X 3 is N, and the others thereof are not N; or ii) each of X 1 to X 3 is not N,
R 1 to R 3 are each independently hydrogen, deuterium, a C 1 -C 20 alkyl group, a C 1 -C 20 alkyl group substituted with at least one deuterium, a C 1 -C 20 alkoxy group, a C 1 -C 20 alkoxy group substituted with at least one deuterium, or —Si(Q 101 )(Q 102 )(Q 103 ),
L 1 and L 2 are each a single bond,
L 3 to L 5 are each independently selected from:
a single bond; and
a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with at least one R 10a ,
a1 to a5 are each independently an integer from 1 to 5, and
Ar 2 is a group represented by Formula 3A, a group represented by Formula 3B, a group represented by Formula 3C, a group represented by Formula 3D, a group represented by Formula 3E, or a group represented by Formula 3F,
Ar 1 is a group represented by one selected from Formulae D′-1 to D′-7 and D007 to D279:
provided that when i) X 1 is C(R 1 ), X 2 is C(R 2 ), and X 3 is C(R 3 ) and ii) L 3 is a single bond, then a group represented by
is represented by one selected from Formulae A1 to A38,
wherein, in Formulae 3A to 3F,
ring A 31 to ring A 33 are each independently a C 5 -C 60 carbocyclic group or a π electron-rich C 1 -C 60 heterocyclic group,
X 51 is a single bond, N(Z 51a ), C(Z 51a )(Z 51b ), Si(Z 51a )(Z 51b ), O, or S,
X 54 is N(Z 54a ), C(Z 54a )(Z 54b ), Si(Z 54a )(Z 54b ), O, or S,
X 55 is N or C(Z 55 ),
X 56 is N or C(Z 56 ),
X 57 is N or C(Z 57 ),
Z 31 to Z 33 , Z 51a , Z 51b , Z 54a , Z 54b , and Z 55 to Z 57 are each independently selected from:
hydrogen, deuterium, a cyano group, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group; and
a C 5 -C 60 carbocyclic group, a pyridine group, and a π electron-rich C 1 -C 60 heterocyclic group, each unsubstituted or substituted with at least one R 10b ,
b31 to b33 are each independently an integer from 1 to 10,
* indicates a binding site to a neighboring atom,
X 11 to X 13 are each independently N or C(CN),
R 4 and R 5 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 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted C 2 -C 60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q 111 )(Q 112 )(Q 113 ),
R 10a and R 10b are each independently deuterium, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a (C 1 -C 20 alkyl)phenyl group, a di(C 1 -C 20 alkyl)phenyl group, a tri (C 1 -C 20 alkyl)phenyl group, a (C 6 -C 20 aryl)phenyl group, a di(C 6 -C 20 aryl)phenyl group, a tri (C 6 -C 20 aryl)phenyl group, a terphenyl group, a tetraphenyl group, a fluorenyl group, a (C 1 -C 20 alkyl) fluorenyl group, a di(C 1 -C 20 alkyl) fluorenyl group, a tri (C 1 -C 20 alkyl) fluorenyl group, a (C 6 -C 20 aryl) fluorenyl group, a di(C 6 -C 20 aryl) fluorenyl group, a tri (C 6 -C 20 aryl) fluorenyl group, a carbazolyl group, a (C 1 -C 20 alkyl) carbazolyl group, a di(C 1 -C 20 alkyl) carbazolyl group, a tri (C 1 -C 20 alkyl) carbazolyl group, a (C 6 -C 20 aryl) carbazolyl group, a di(C 6 -C 20 aryl) carbazolyl group, a tri (C 6 -C 20 aryl) carbazolyl group, a dibenzofuranyl group, a (C 1 -C 20 alkyl)dibenzofuranyl group, a di(C 1 -C 20 alkyl)dibenzofuranyl group, a tri (C 1 -C 20 alkyl)dibenzofuranyl group, a (C 6 -C 20 aryl)dibenzofuranyl group, a di(C 6 -C 20 aryl)dibenzofuranyl group, a tri (C 6 -C 20 aryl)dibenzofuranyl group, a dibenzothiophenyl group, a (C 1 -C 20 alkyl)dibenzothiophenyl group, a di(C 1 -C 20 alkyl)dibenzothiophenyl group, a tri (C 1 -C 20 alkyl)dibenzothiophenyl group, a (C 6 -C 20 aryl)dibenzothiophenyl group, a di(C 6 -C 20 aryl)dibenzothiophenyl group, a tri (C 6 -C 20 aryl)dibenzothiophenyl group, or —Si(Q 121 )(Q 122 )(Q 123 ),
at least one substituent of the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 7 -C 60 arylalkyl group, the substituted C 1 -C 60 heteroaryl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio group, the substituted C 2 -C 60 heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 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, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 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 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), and —P(═O)(Q 18 )(Q 19 );
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 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy 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 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), —B(Q 26 )(Q 27 ), and —P(═O)(Q 28 )(Q 29 ); and
—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), —B(Q 36 )(Q 37 ), and —P(═O)(Q 38 )(Q 39 ), and
Q 101 to Q 103 , Q 111 to Q 113 , Q 121 to Q 123 , Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 are each independently selected from hydrogen, 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 or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy 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 biphenyl group, a terphenyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group,
the heterocyclic compound has a singlet energy level in a range of about 2.5 electron volts to about 3.0 electron volts, and
the singlet energy level is evaluated by using a density functional theory method structurally optimized at a level of B3LYP/6-31G(d,p).
2 . The heterocyclic compound of claim 1 , wherein
L 3 to L 5 are each independently selected from:
a single bond; and
a benzene group, a fluorene group, a pyridine group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, an acridine group, and a dihydroacridine group, each unsubstituted or substituted with at least one R 10a .
3 . The heterocyclic compound of claim 1 , wherein
L 3 is selected from a single bond and groups represented by Formulae 2-1 to 2-4:
wherein, in Formulae 2-1 to 2-4,
R 11 to R 13 are each independently hydrogen, deuterium, or a C 1 -C 10 alkyl group,
* indicates a binding site to a 6-membered ring on the left side in Formula 1, and
*′ indicates a binding site to a 6-membered ring on the right side in Formula 1.
4 . The heterocyclic compound of claim 1 , wherein
ring A 31 to ring A 33 are each independently a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a chrysene group, an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, an acridine group, or a dihydroacridine group.
5 . The heterocyclic compound of claim 1 , wherein
a ring represented by
in Formula 3A is selected from groups represented by Formulae 3A-1 to 3A-49,
a ring represented by
in Formula 3B is selected from groups represented by Formulae 3B-1 to 3B-40, and
a ring represented by
in Formula 3C is a group represented by Formula 3C-1:
wherein, in Formulae 3A-1 to 3A-49, 3B-1 to 3B-40 and 3C-1, X 51 and * are each independently the same as described in claim 1 , X 52 is N(Z 52a ), C(Z 52a )(Z 52b ), Si(Z 52a )(Z 52b ), O, or S, X 53 is N(Z 53a ), C(Z 53a )(Z 53b ), Si(Z 53a )(Z 53b ), O, or S, and Z 52a , Z 52b , Z 53a , and Z 53b are each independently the same as described in connection with Z 51a in claim 1 .
6 . The heterocyclic compound of claim 1 , wherein
X 11 to X 13 are each N.
7 . The heterocyclic compound of claim 1 , wherein
R 4 and R 5 are each independently selected from a phenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, a fluorenyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a dibenzosilolyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, an acridinyl group, and a dihydroacridinyl group, each unsubstituted or substituted with at least one R 10c , and
R 10c is the same as described in connection with R 10a in claim 1 .
8 . The heterocyclic compound of claim 1 , wherein,
in Formula 1,
a group represented by *-(L 3 ) a3 -*′ is a single bond or a group represented by one selected from Formulae L-1 to L-5,
a group represented by
is a group represented by one selected from Formulae A1 to A38,
* in a group represented by
indicates a binding site to a neighboring atom, and
in a group represented by *-(L 3 ) a3 -*′, * indicates a binding site to a 6-membered ring on the left side in Formula 1, and *′ indicates a binding site to a 6-membered ring on the right side in Formula 1:
wherein, in the formulae above, * and *′ each indicate a binding site to a neighboring atom.
9 . The heterocyclic compound of claim 1 , wherein
a difference between a singlet energy level of the heterocyclic compound and a triplet energy level of the heterocyclic compound is in a range of about 0 electron volts to about 0.5 electron volts, and
the singlet energy level and the triplet energy level are evaluated by using a density functional theory method structurally optimized at a level of B3LYP/6-31G(d,p).
10 . An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode,
wherein the organic layer comprises an emission layer, the emission layer comprises a host and a dopant,
the dopant comprises the heterocyclic compound represented by Formula 1, and
an amount of the host is larger than an amount of the dopant.
11 . The organic light-emitting device of claim 10 , wherein
the first electrode is an anode,
the second electrode is a cathode,
the organic layer comprises a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode,
wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and
wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
12 . The organic light-emitting device of claim 10 , wherein
the emission layer emits blue light.
13 . The organic light-emitting device of claim 10 , wherein
a ratio of a delayed fluorescence component emitted from the heterocyclic compound of the emission layer to a total emission component emitted from the emission layer is 90% or more.
14 . The organic light-emitting device of claim 10 , wherein
the host comprises at least one selected from a first material and a second material,
the first material comprises at least one π electron-rich cyclic group and does not comprise an electron transport moiety,
the second material comprises at least one π electron-rich cyclic group and at least one electron transport moiety, and
the electron transport moiety is selected from a cyano group, a π electron-depleted nitrogen-containing cyclic group, and a group represented by one selected from the following formulae:
wherein *, *′, and *″ in the formulae each indicate a binding site to a neighboring atom.
15 . The organic light-emitting device of claim 14 , wherein
the first material comprises a cyano group-free benzene group and a cyano group-free carbazole group, and
the second material comprises at least one selected from a cyano group-containing benzene group and a cyano group-containing carbazole group.